(en)Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed.

1.ApplicationNumber: US-201514878836-A
1.PublishNumber: US-2016184281-A1
2.Date Publish: 20160630
3.Inventor: CLARK RICHARD F.
SORENSEN Bryan
OSUMA AUGUSTINE T.
FREY ROBIN
LONGENECKER KENTON
DOHERTY GEORGE
CURTIN MICHAEL L.
MICHAELIDES Michael
SWEIS RAMZI
PLIUSHCHEV MARINA
JUDD ANDREW
HANSEN TODD
HEYMAN HOWARD R.

4.Inventor Harmonized: CLARK RICHARD F(US)
SORENSEN Bryan(US)
OSUMA AUGUSTINE T(US)
FREY ROBIN(US)
LONGENECKER KENTON(US)
DOHERTY GEORGE(US)
CURTIN MICHAEL L(US)
MICHAELIDES Michael(US)
SWEIS RAMZI(US)
PLIUSHCHEV MARINA(US)
JUDD ANDREW(US)
HANSEN TODD(US)
HEYMAN HOWARD R(US)

5.Country: US
6.Claims:
(en)Disclosed are compounds which inhibit the activity of NAMPT, compositions containing the compounds and methods of treating diseases during which NAMPT is expressed.

7.Description:
(en)This application claims priority to U.S. Provisional Application Ser. No. 61/645,679, filed May 11, 2012, U.S. Provisional Application Ser. No. 61/718,998, filed Oct. 26, 2012, and U.S. Provisional Application Ser. No. 61/779,626, filed Mar. 13, 2013, which are incorporated by reference in their entirety.


FIELD OF THE INVENTION
This invention pertains to compounds which inhibit the activity of NAMPT, compositions containing the compounds, and methods of treating diseases during which NAMPT is expressed.
BACKGROUND OF THE INVENTION
NAD+ (nicotinamide adenine dinucleotide) is a coenzyme that plays a critical role in many physiologically essential processes (Ziegkel, M. Eur. J. Biochem. 267, 1550-1564, 2000). NAD is necessary for several signaling pathways including among others poly ADP-ribosylation in DNA repair, mono-ADP-ribosylation in both the immune system and G-protein-coupled signaling, and NAD is also required by sirtuins for their deacetylase activity (Garten, A. et al Trends in Endocrinology and Metabolism, 20, 130-138, 2008).
NAMPT (also known as pre-B-cell-colony-enhancing factor (PBEF) and visfatin) is an enzyme that catalyzes the phosphoribosylation of nicotinamide and is the rate-limiting enzyme in one of two pathways that salvage NAD.









Increasing evidence suggests that NAMPT inhibitors have potential as anticancer agents. Cancer cells have a higher basal turnover of NAD and also display higher energy requirements compared with normal cells. Additionally, increased NAMPT expression has been reported in colorectal cancer (Van Beijnum, J. R. et al Int. J. Cancer 101, 118-127, 2002) and NAMPT is involved in angiogenesis (Kim, S. R. et al. Biochem. Biophys. Res. Commun. 357, 150-156, 2007). Small-molecule inhibitors of NAMPT have been shown to cause depletion of intracellular NAD+ levels and ultimately induce tumor cell death (Hansen, C M et al. Anticancer Res. 20, 42111-4220, 2000) as well as inhibit tumor growth in xenograft models (Olese, U. H. et al. Mol Cancer Ther. 9, 1609-1617, 2010).
NAMPT inhibitors also have potential as therapeutic agents in inflammatory and metabolic disorders (Galli, M. et al Cancer Res. 70, 8-11, 2010). For example, NAMPT is the predominant enzyme in T and B lymphocytes. Selective inhibition of NAMPT leads to NAD+ depletion in lymphocytes blocking the expansion that accompanies autoimmune disease progression whereas cell types expressing the other NAD+ generating pathways might be spared. A small molecule NAMPT inhibitor (FK866) has been shown to selectively block proliferation and induce apoptosis of activated T cells and was efficacious in animal models of arthritis (collagen induced arthritis) (Busso, N. et al. Plos One 3, e2267, 2008). FK866 ameliorated the manifestations of experimental autoimmune encephalomyelitis (EAE), a model of T-cell mediated autoimmune disorders. (Bruzzone, S et al. Plos One 4, e7897, 2009). NaMPT activity increases NF-kB transcriptional activity in human vascular endothelial cell, resulting in MMP-2 and MMP-9 activation, suggesting a role for NAMPT inhibitors in the prevention of inflammatory mediated complications of obesity and type 2 diabetes (Adya, R. et. Al. Diabetes Care, 31, 758-760, 2008).
SUMMARY OF THE INVENTION
One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)









or a therapeutically acceptable salt thereof, wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
Z is CH, C—F, C—Cl, C—Br, C—I or N; or
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is hydrogen, F, Cl, Br, or I;
Z is CR 2 ; and
R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
m is 4, 5, or 6; and
n is 1 or 2;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent;
when X is CY 1 and Y 1 is hydrogen; R 1 is NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is R 3 phenyl; the phenyl is not substituted at the para position with SO 2 R 4 or SO 2 NHR 4 .
In another embodiment of Formula (IA), R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (IA), R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (IA), R 1 is hydrogen; and R 2 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (IA), R 1 is hydrogen; and R 2 is CH 2 NHC(O)R 3 . In one embodiment of Formula (IA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IA), R 1 is NHC(O)NHR 3 ; R 2 is hydrogen; and R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IA), R 1 is CH 2 NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IA), R 1 is hydrogen; R 2 is CH 2 NHC(O)NHR 3 ; and R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In one embodiment of Formula (IA), R 1 is hydrogen; R 2 is CH 2 NHC(O)R 3 ; and R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IA), R 1 is NHC(O)NHR 3 ; R 2 is hydrogen; and R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IA), R 1 is CH 2 NHC(O)R 3 ; R 2 is hydrogen; and R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IA), R 1 is hydrogen; R 2 is CH 2 NHC(O)NHR 3 ; and R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IA), R 1 is hydrogen; R 2 is CH 2 NHC(O)R 3 ; and R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
Still another embodiment pertains to compounds, which are
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; 4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide; N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide; N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(moipholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(moipholin-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate; 4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]butyl}urea; 1-{4-[1-(cyclopentylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]piperidin-4-yl}butyl)urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]butyl}urea; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(molpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-6-ylurea; 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl)[3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide; 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide; 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-7-ylurea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate; tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate; tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide; 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate; tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide; 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide; 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide; 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate; tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea; 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide; 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea; 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea; tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate; 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide; 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide; tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide; 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide; 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide; 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide; propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide; 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; tert-butyl 4-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide; 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide; 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea; 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide; 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide; 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate; 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide; 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}acetamide; tert-butyl 4-{4-[(imidazo[1,2-b]pyridazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide; 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; 2-(imidazo[1,2-a]pyridin-6-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide; N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide; 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide; 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide; 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-[(3-chloroimidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(cyclopentylacetyl)amino]benzamide; N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; 2-(imidazo[1,2-a]pyridin-7-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide; 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide; N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide; 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide; 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide; 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide; 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide; 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-[(cyclopentylacetyl)amino]-N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide; N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide; 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; and pharmaceutically acceptable salts thereof

Still another embodiment pertains to compounds of Formula (IA), selected from the group consisting of
4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide; 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.

Another embodiment pertains to a composition for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic upus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said composition comprising an excipient and a therapeutically effective amount of a compound of Formula (IA), or pharmaceutically acceptable salts thereof
Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said method comprising administering to the patient a therapeutically effective amount of a compound of Formula (IA), or pharmaceutically acceptable salts thereof
Another embodiment pertains to a method of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia or spleen cancer in a patient, said method comprising administering to the patient therapeutically effective amount of the compound of Formula (IA), or pharmaceutically acceptable salts thereof; and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.


DETAILED DESCRIPTION OF THE INVENTION
This detailed description is intended only to acquaint others skilled in the art with Applicants' invention, its principles, and its practical application so that others skilled in the art may adapt and apply the invention in its numerous forms, as they may be best suited to the requirements of a particular use. This description and its specific examples are intended for purposes of illustration only. This invention, therefore, is not limited to the embodiments described in this patent application, and may be variously modified.
ABBREVIATIONS AND DEFINITIONS
Unless otherwise defined herein, scientific and technical terms used in connection with the present invention shall have the meanings that are commonly understood by those of ordinary skill in the art. The meaning and scope of the terms should be clear, however, in the event of any latent ambiguity, definitions provided herein take precedent over any dictionary or extrinsic definition. In this application, the use of “or” means “and/or” unless stated otherwise. Furthermore, the use of the term “including”, as well as other forms, such as “includes” and “included”, is not limiting. With reference to the use of the words “comprise” or “comprises” or “comprising” in this patent application (including the claims), Applicants note that unless the context requires otherwise, those words are used on the basis and clear understanding that they are to be interpreted inclusively, rather than exclusively, and that Applicants intend each of those words to be so interpreted in construing this patent application, including the claims below. For a variable that occurs more than one time in any substituent or in the compound of the invention or any other formulae herein, its definition on each occurrence is independent of its definition at every other occurrence. Combinations of substituents are permissible only if such combinations result in stable compounds. Stable compounds are compounds which can be isolated in a useful degree of purity from a reaction mixture.
It is meant to be understood that proper valences are maintained for all combinations herein, that monovalent moieties having more than one atom are attached through their left ends, and that divalent moieties are drawn from left to right.
As used in the specification and the appended claims, unless specified to the contrary, the following terms have the meaning indicated:
The term “alkyl” (alone or in combination with another term(s)) means a straight- or branched-chain saturated hydrocarbyl substituent typically containing from 1 to about 10 carbon atoms; or in another embodiment, from 1 to about 8 carbon atoms; in another embodiment, from 1 to about 6 carbon atoms; and in another embodiment, from 1 to about 4 carbon atoms. Examples of such substituents include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, and hexyl and the like.
The term “alkenyl” (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more double bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms. Examples of such substituents include ethenyl (vinyl), 2-propenyl, 3-propenyl, 1,4-pentadienyl, 1,4-butadienyl, 1-butenyl, 2-butenyl, and 3-butenyl and the like.
The term “alkynyl” (alone or in combination with another term(s)) means a straight- or branched-chain hydrocarbyl substituent containing one or more triple bonds and typically from 2 to about 10 carbon atoms; or in another embodiment, from 2 to about 8 carbon atoms; in another embodiment, from 2 to about 6 carbon atoms; and in another embodiment, from 2 to about 4 carbon atoms. Examples of such substituents include ethynyl, 2-propynyl, 3-propynyl, 2-butynyl, and 3-butynyl and the like.
The term “carbocyclyl” (alone or in combination with another term(s)) means a saturated cyclic (i.e., “cycloalkyl”), partially saturated cyclic (i.e., “cycloalkenyl”), or completely unsaturated (i.e., “aryl”) hydrocarbyl substituent containing from 3 to 14 carbon ring atoms (“ring atoms” are the atoms bound together to form the ring or rings of a cyclic substituent). A carbocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
A carbocyclyl may be a single ring structure, which typically contains from 3 to 8 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms. Examples of such single-ring carbocyclyls include cyclopropyl (cyclopropanyl), cyclobutyl (cyclobutanyl), cyclopentyl (cyclopentanyl), cyclopentenyl, cyclopentadienyl, cyclohexyl (cyclohexanyl), cyclohexenyl, cyclohexadienyl, and phenyl. A carbocyclyl may alternatively be polycyclic (i.e., may contain more than one ring). Examples of polycyclic carbocyclyls include bridged, fused, and spirocyclic carbocyclyls. In a spirocyclic carbocyclyl, one atom is common to two different rings. An example of a spirocyclic carbocyclyl is spiropentanyl. In a bridged carbocyclyl, the rings share at least two common non-adjacent atoms. Examples of bridged carbocyclyls include bicyclo[2.2.1]heptanyl, bicyclo[2.2.1]hept-2-enyl, and adamantanyl. In a fused-ring carbocyclyl system, two or more rings may be fused together, such that two rings share one common bond. Examples of two- or three-fused ring carbocyclyls include naphthalenyl, tetrahydronaphthalenyl (tetralinyl), indenyl, indanyl (dihydroindenyl), anthracenyl, phenanthrenyl, and decalinyl.
The term “cycloalkyl” (alone or in combination with another term(s)) means a saturated cyclic hydrocarbyl substituent containing from 3 to 14 carbon ring atoms. A cycloalkyl may be a single carbon ring, which typically contains from 3 to 8 carbon ring atoms and more typically from 3 to 6 ring atoms. Examples of single-ring cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. A cycloalkyl may alternatively be polycyclic or contain more than one ring. Examples of polycyclic cycloalkyls include bridged, fused, and spirocyclic carbocyclyls.
The term “aryl” (alone or in combination with another term(s)) means an aromatic carbocyclyl containing from 6 to 14 carbon ring atoms. An aryl may be monocyclic or polycyclic (i.e., may contain more than one ring). In the case of polycyclic aromatic rings, only one ring the polycyclic system is required to be unsaturated while the remaining ring(s) may be saturated, partially saturated or unsaturated. Examples of aryls include phenyl, naphthalenyl, indenyl, indanyl, and tetrahydronapthyl.
In some instances, the number of carbon atoms in a hydrocarbyl substituent (e.g., alkyl, alkenyl, alkynyl, or cycloalkyl) is indicated by the prefix “C x -C y -”, wherein x is the minimum and y is the maximum number of carbon atoms in the substituent. Thus, for example, “C 1 -C 6 -alkyl” refers to an alkyl substituent containing from 1 to 6 carbon atoms. Illustrating further, C 3 -C 8 -cycloalkyl means a saturated hydrocarbyl ring containing from 3 to 8 carbon ring atoms.
The term “hydrogen” (alone or in combination with another term(s)) means a hydrogen radical, and may be depicted as —H.
The term “hydroxy” (alone or in combination with another term(s)) means —OH.
The term “carboxy” (alone or in combination with another term(s)) means —C(O)—OH.
The term “amino” (alone or in combination with another term(s)) means —NH 2 .
The term “halogen” or “halo” (alone or in combination with another term(s)) means a fluorine radical (which may be depicted as —F), chlorine radical (which may be depicted as —Cl), bromine radical (which may be depicted as —Br), or iodine radical (which may be depicted as —I).
If a substituent is described as being “substituted”, a non-hydrogen radical is in the place of hydrogen radical on a carbon or nitrogen of the substituent. Thus, for example, a substituted alkyl substituent is an alkyl substituent in which at least one non-hydrogen radical is in the place of a hydrogen radical on the alkyl substituent. To illustrate, monofluoroalkyl is alkyl substituted with a fluoro radical, and difluoroalkyl is alkyl substituted with two fluoro radicals. It should be recognized that if there are more than one substitution on a substituent, each non-hydrogen radical may be identical or different (unless otherwise stated).
If a substituent is described as being “optionally substituted”, the substituent may be either (1) not substituted or (2) substituted. If a substituent is described as being optionally substituted with up to a particular number of non-hydrogen radicals, that substituent may be either (1) not substituted; or (2) substituted by up to that particular number of non-hydrogen radicals or by up to the maximum number of substitutable positions on the substituent, whichever is less. Thus, for example, if a substituent is described as a heteroaryl optionally substituted with up to 3 non-hydrogen radicals, then any heteroaryl with less than 3 substitutable positions would be optionally substituted by up to only as many non-hydrogen radicals as the heteroaryl has substitutable positions. To illustrate, tetrazolyl (which has only one substitutable position) would be optionally substituted with up to one non-hydrogen radical. To illustrate further, if an amino nitrogen is described as being optionally substituted with up to 2 non-hydrogen radicals, then a primary amino nitrogen will be optionally substituted with up to 2 non-hydrogen radicals, whereas a secondary amino nitrogen will be optionally substituted with up to only 1 non-hydrogen radical.
This patent application uses the terms “substituent” and “radical” interchangeably.
The prefix “halo” indicates that the substituent to which the prefix is attached is substituted with one or more independently selected halogen radicals. For example, haloalkyl means an alkyl substituent in which at least one hydrogen radical is replaced with a halogen radical. Examples of haloalkyls include chloromethyl, 1-bromoethyl, fluoromethyl, difluoromethyl, trifluoromethyl, and 1,1,1-trifluoroethyl. It should be recognized that if a substituent is substituted by more than one halogen radical, those halogen radicals may be identical or different (unless otherwise stated).
The prefix “perhalo” indicates that every hydrogen radical on the substituent to which the prefix is attached is replaced with independently selected halogen radicals, i.e., each hydrogen radical on the substituent is replaced with a halogen radical. If all the halogen radicals are identical, the prefix typically will identify the halogen radical. Thus, for example, the term “perfluoro” means that every hydrogen radical on the substituent to which the prefix is attached is substituted with a fluorine radical. To illustrate, the term “perfluoroalkyl” means an alkyl substituent wherein a fluorine radical is in the place of each hydrogen radical.
The term “carbonyl” (alone or in combination with another term(s)) means —C(O)—.
The term “aminocarbonyl” (alone or in combination with another term(s)) means —C(O)—NH 2 .
The term “oxo” (alone or in combination with another term(s)) means (═O).
The term “oxy” (alone or in combination with another term(s)) means an ether substituent, and may be depicted as —O—.
The term “alkylhydroxy” (alone or in combination with another term(s)) means alkyl-OH.
The term “alkylamino” (alone or in combination with another term(s)) means alkyl-NH 2 .
The term “alkyloxy” (alone or in combination with another term(s)) means an alkylether substituent, i.e., —O-alkyl. Examples of such a substituent include methoxy (—O—CH 3 ), ethoxy, n-propoxy, isopropoxy, n-butoxy, iso-butoxy, sec-butoxy, and tert-butoxy.
The term “alkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl.
The term “aminoalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-NH 2 .
The term “alkyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-alkyl.
The term “carbocyclylcarbonyl” (alone or in combination with another term(s)) means —C(O)-carbocyclyl.
Similarly, the term “heterocyclylcarbonyl” (alone or in combination with another term(s)) means —C(O)-heterocyclyl.
The term “carbocyclylalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-carbocyclyl.
Similarly, the term “heterocyclylalkylcarbonyl” (alone or in combination with another term(s)) means —C(O)-alkyl-heterocyclyl.
The term “carbocyclyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-carbocyclyl.
The term “carbocyclylalkyloxycarbonyl” (alone or in combination with another term(s)) means —C(O)—O-alkyl-carbocyclyl.
The term “thio” or “thia” (alone or in combination with another term(s)) means a thiaether substituent, i.e., an ether substituent wherein a divalent sulfur atom is in the place of the ether oxygen atom. Such a substituent may be depicted as —S—. This, for example, “alkyl-thio-alkyl” means alkyl-S-alkyl (alkyl-sulfanyl-alkyl).
The term “thiol” or “sulfhydryl” (alone or in combination with another term(s)) means a sulfhydryl substituent, and may be depicted as —SH.
The term “(thiocarbonyl)” (alone or in combination with another term(s)) means a carbonyl wherein the oxygen atom has been replaced with a sulfur. Such a substituent may be depicted as —C(S)—.
The term “sulfonyl” (alone or in combination with another term(s)) means —S(O) 2 —.
The term “aminosulfonyl” (alone or in combination with another term(s)) means —S(O) 2 —NH 2 .
The term “sulfinyl” or “sulfoxido” (alone or in combination with another term(s)) means —S(O)—.
The term “heterocyclyl” (alone or in combination with another term(s)) means a saturated (i.e., “heterocycloalkyl”), partially saturated (i.e., “heterocycloalkenyl”), or completely unsaturated (i.e., “heteroaryl”) ring structure containing a total of 3 to 14 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur. A heterocyclyl may be a single-ring (monocyclic) or polycyclic ring structure.
A heterocyclyl may be a single ring, which typically contains from 3 to 7 ring atoms, more typically from 3 to 6 ring atoms, and even more typically 5 to 6 ring atoms. Examples of single-ring heterocyclyls include 1,2,3,6-tetrahydropyridine, thiomorpholinyl, tetrahydropyranyl, furanyl, dihydrofuranyl, tetrahydrofuranyl, thiophenyl (thiofuranyl), dihydrothiophenyl, tetrahydrothiophenyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, tetrazolyl, oxazolyl, oxazolidinyl, isoxazolidinyl, isoxazolyl, thiazolyl, isothiazolyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, thiodiazolyl, oxadiazolyl (including 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl(furazanyl), or 1,3,4-oxadiazolyl), oxatriazolyl (including 1,2,3,4-oxatriazolyl or 1,2,3,5-oxatriazolyl), dioxazolyl (including 1,2,3-dioxazolyl, 1,2,4-dioxazolyl, 1,3,2-dioxazolyl, or 1,3,4-dioxazolyl), oxathiazolyl, oxathiolyl, oxathiolanyl, pyranyl, dihydropyranyl, thiopyranyl, tetrahydrothiopyranyl, pyridinyl (azinyl), piperidinyl, diazinyl (including pyridazinyl (1,2-diazinyl), pyrimidinyl (1,3-diazinyl), or pyrazinyl (1,4-diazinyl)), piperazinyl, pyrrolidin-2-only, triazinyl (including 1,3,5-triazinyl, 1,2,4-triazinyl, and 1,2,3-triazinyl)), oxazinyl (including 1,2-oxazinyl, 1,3-oxazinyl, or 1,4-oxazinyl)), oxathiazinyl (including 1,2,3-oxathiazinyl, 1,2,4-oxathiazinyl, 1,2,5-oxathiazinyl, or 1,2,6-oxathiazinyl)), oxadiazinyl (including 1,2,3-oxadiazinyl, 1,2,4-oxadiazinyl, 1,4,2-oxadiazinyl, or 1,3,5-oxadiazinyl)), morpholinyl, azepinyl, oxepinyl, thiepinyl, and diazepinyl.
A heterocyclyl may alternatively be polycyclic (i.e., may contain more than one ring). Examples of polycyclic heterocyclyls include bridged, fused, and spirocyclic heterocyclyls. In a spirocyclic heterocyclyl, one atom is common to two different rings. In a bridged heterocyclyl, the rings share at least two common non-adjacent atoms. In a fused-ring heterocyclyl, two or more rings may be fused together, such that two rings share one common bond. Examples of fused-ring heterocyclyls include hexahydro-furo[3,4-c]pyrrole, hexahydro-furo[3,4-b]pyrrole, octahydro-pyrrolo[3,4-b]pyridine, octahydro-pyrrolo[3,4-c]pyridine, (3aR,6aR)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrole, (3aR,6aR)-octahydro-pyrrolo[3,4-b]pyrrole, 6-methyl-2,6-diaza-bicyclo[3.2.0]heptane, (3aS,6aR)-2-methyl-octahydro-pyrrolo[3,4-c]pyrrole, decahydro-[1,5]naphthyridine, 2,3-dihydrobenzofuranyl, 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indolyl, thieno[3,2-c]pyridinyl, furo[3,2-c]pyridinyl, phthalazin-1(2H)-onyl, isoquinolinyl, isoquinolin-1(2H)-onyl, 5,6,7,8-tetrahydrophthalazin-1(2H)-onyl, fluorophthalazin-1(2H)-onyl, (Z)-3H-benzo[d][1,2]diazepin-4(5H)-onyl, (trifluoromethyl)phthalazin-1(2H)-onyl, pyrrolo[1,2-d][1,2,4]triazin-1(2H)-onyl, 1,2,3,4-tetrahydroisoquinolinyl, 2,3-dihydrobenzo[b][1,4]dioxinyl, 5,6,7,8-tetrahydrophthalazin-1(2H)-onyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazinyl, 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazinyl, thieno[3,2-c]pyridinyl, furo[3,2-c]pyridinyl, indolizinyl, pyranopyrrolyl, 4H-quinolizinyl, purinyl, naphthyridinyl, pyridopyridinyl (including pyrido[3,4-b]-pyridinyl, pyrido[3,2-b]-pyridinyl, or pyrido[4,3-b]-pyridinyl), and pteridinyl. Other examples of fused-ring heterocyclyls include benzo-fused heterocyclyls, such as benzimidazolyl, benzo[d][1,3]dioxolyl, indolyl, isoindolyl (isobenzazolyl, pseudoisoindolyl), indoleninyl (pseudoindolyl), isoindazolyl (benzpyrazolyl), benzazinyl (including quinolinyl (1-benzazinyl) or isoquinolinyl (2-benzazinyl)), phthalazinyl, quinoxalinyl, quinazolinyl, benzodiazinyl (including cinnolinyl (1,2-benzodiazinyl) or quinazolinyl (1,3-benzodiazinyl)), benzopyranyl (including chromanyl or isochromanyl), benzoxazinyl (including 1,3,2-benzoxazinyl, 1,4,2-benzoxazinyl, 2,3,1-benzoxazinyl, or 3,1,4-benzoxazinyl), and benzisoxazinyl (including 1,2-benzisoxazinyl or 1,4-benzisoxazinyl). Examples of spirocyclic heterocyclyls include 1,4-dioxa-8-azaspiro[4.5]decanyl.
The term “5-6 membered heteroaryl” (alone or in combination with another term(s)) means aromatic heterocyclyl containing a total of 5 to 6 ring atoms. At least one of the ring atoms is a heteroatom (i.e., oxygen, nitrogen, or sulfur), with the remaining ring atoms being independently selected from the group consisting of carbon, oxygen, nitrogen, and sulfur.
The term “heterocycloalkyl” (alone or in combination with another term(s)) means a saturated heterocyclyl.
The term “heteroaryl” (alone or in combination with another term(s)) means an aromatic heterocyclyl containing from 5 to 14 ring atoms. A heteroaryl may be a single ring or 2 or 3 fused rings. Examples of heteroaryl substituents include 6-membered ring substituents such as pyridyl, pyrazyl, pyrimidinyl, pyridazinyl, and 1,3,5-, 1,2,4- or 1,2,3-triazinyl; 5-membered ring substituents such as imidazyl, furanyl, thiophenyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, 1,2,3-, 1,2,4-, 1,2,5-, or 1,3,4-oxadiazolyl and isothiazolyl; 6/5-membered fused ring substituents such as benzothiofuranyl, benzisoxazolyl, benzoxazolyl, and purinyl; and 6/6-membered fused rings such as benzopyranyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, and benzoxazinyl.
A prefix attached to a multi-component substituent only applies to the first component. To illustrate, the term “alkylcycloalkyl” contains two components: alkyl and cycloalkyl. Thus, the C 1 -C 6 -prefix on C 1 -C 6 -alkylcycloalkyl means that the alkyl component of the alkylcycloalkyl contains from 1 to 6 carbon atoms; the C 1 -C 6 -prefix does not describe the cycloalkyl component. To illustrate further, the prefix “halo” on haloalkyloxyalkyl indicates that only the alkyloxy component of the alkyloxyalkyl substituent is substituted with one or more halogen radicals. If halogen substitution may alternatively or additionally occur on the alkyl component, the substituent would instead be described as “halogen-substituted alkyloxyalkyl” rather than “haloalkyloxyalkyl.” And finally, if the halogen substitution may only occur on the alkyl component, the substituent would instead be described as “alkyloxyhaloalkyl.”
The terms “treat”, “treating” and “treatment” refer to a method of alleviating or abrogating a disease and/or its attendant symptoms.
The terms “prevent”, “preventing” and “prevention” refer to a method of preventing the onset of a disease and/or its attendant symptoms or barring a subject from acquiring a disease. As used herein, “prevent”, “preventing” and “prevention” also include delaying the onset of a disease and/or its attendant symptoms and reducing a subject's risk of acquiring a disease.
The term “therapeutically effective amount” refers to that amount of the compound being administered sufficient to prevent development of or alleviate to some extent one or more of the symptoms of the condition or disorder being treated.
The term “modulate” refers to the ability of a compound to increase or decrease the function, or activity, of a kinase. “Modulation”, as used herein in its various forms, is intended to encompass antagonism, agonism, partial antagonism and/or partial agonism of the activity associated with kinase. Kinase inhibitors are compounds that, e.g., bind to, partially or totally block stimulation, decrease, prevent, delay activation, inactivate, desensitize, or down regulate signal transduction. Kinase activators are compounds that, e.g., bind to, stimulate, increase, open, activate, facilitate, enhance activation, sensitize or up regulate signal transduction.
The term “composition” as used herein is intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combination of the specified ingredients in the specified amounts. By “pharmaceutically acceptable” it is meant the carrier, diluent or excipient must be compatible with the other ingredients of the formulation and not deleterious to the recipient thereof
The “subject” is defined herein to include animals such as mammals, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like. In preferred embodiments, the subject is a human.
Isotope Enriched or Labeled Compounds
Compounds of the invention can exist in isotope-labeled or -enriched form containing one or more atoms having an atomic mass or mass number different from the atomic mass or mass number most abundantly found in nature. Isotopes can be radioactive or non-radioactive isotopes. Isotopes of atoms such as hydrogen, carbon, phosphorous, sulfur, fluorine, chlorine, and iodine include, but are not limited to, 2 H, 3 H, 13 C, 14 C, 15 N, 18 O, 32 P, 35 S, 18 F, 36 Cl, and 125 I. Compounds that contain other isotopes of these and/or other atoms are within the scope of this invention.
In another embodiment, the isotope-labeled compounds contain deuterium ( 2 H), tritium ( 3 H) or 14 C isotopes. Isotope-labeled compounds of this invention can be prepared by the general methods well known to persons having ordinary skill in the art. Such isotope-labeled compounds can be conveniently prepared by carrying out the procedures disclosed in the Examples disclosed herein and Schemes by substituting a readily available isotope-labeled reagent for a non-labeled reagent. In some instances, compounds may be treated with isotope-labeled reagents to exchange a normal atom with its isotope, for example, hydrogen for deuterium can be exchanged by the action of a deuteric acid such as D 2 SO 4 /D 2 O. In addition to the above, relevant procedures and intermediates are disclosed, for instance, in Lizondo, J et al., Drugs Fut, 21(11), 1116 (1996); Brickner, S J et al., J Med Chem, 39(3), 673 (1996); Mallesham, B et al., Org Lett, 5(7), 963 (2003); PCT publications WO1997010223, WO2005099353, WO1995007271, WO2006008754; U.S. Pat. Nos. 7,538,189; 7,534,814; 7,531,685; 7,528,131; 7,521,421; 7,514,068; 7,511,013; and US Patent Application Publication Nos. 20090137457; 20090131485; 20090131363; 20090118238; 20090111840; 20090105338; 20090105307; 20090105147; 20090093422; 20090088416; and 20090082471, the methods are hereby incorporated by reference.
The isotope-labeled compounds of the invention may be used as standards to determine the effectiveness in binding assays. Isotope containing compounds have been used in pharmaceutical research to investigate the in vivo metabolic fate of the compounds by evaluation of the mechanism of action and metabolic pathway of the nonisotope-labeled parent compound (Blake et al. J. Pharm. Sci. 64, 3, 367-391 (1975)). Such metabolic studies are important in the design of safe, effective therapeutic drugs, either because the in vivo active compound administered to the patient or because the metabolites produced from the parent compound prove to be toxic or carcinogenic (Foster et al., Advances in Drug Research Vol. 14, pp. 2-36, Academic press, London, 1985; Kato et al., J. Labelled Comp. Radiopharmaceut., 36(10):927-932 (1995); Kushner et al., Can. J. Physiol. Pharmacol., 77, 79-88 (1999).
In addition, non-radio active isotope containing drugs, such as deuterated drugs called “heavy drugs,” can be used for the treatment of diseases and conditions related to NAMPT activity. Increasing the amount of an isotope present in a compound above its natural abundance is called enrichment. Examples of the amount of enrichment include from about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 16, 21, 25, 29, 33, 37, 42, 46, 50, 54, 58, 63, 67, 71, 75, 79, 84, 88, 92, 96, to about 100 mol %. Replacement of up to about 15% of normal atom with a heavy isotope has been effected and maintained for a period of days to weeks in mammals, including rodents and dogs, with minimal observed adverse effects (Czajka D M and Finkel A J, Ann. N.Y. Acad. Sci. 1960 84: 770; Thomson J F, Ann. New York Acad. Sci 1960 84: 736; Czakja D M et al., Am. J. Physiol. 1961 201: 357). Acute replacement of as high as 15%-23% in human fluids with deuterium was found not to cause toxicity (Blagojevic N et al. in “Dosimetry & Treatment Planning for Neutron Capture Therapy”, Zamenhof R, Solares G and Harling O Eds. 1994. Advanced Medical Publishing, Madison Wis. pp. 125-134; Diabetes Metab. 23: 251 (1997)).
Stable isotope labeling of a drug can alter its physico-chemical properties such as pKa and lipid solubility. These effects and alterations can affect the pharmacodynamic response of the drug molecule if the isotopic substitution affects a region involved in a ligand-receptor interaction. While some of the physical properties of a stable isotope-labeled molecule are different from those of the unlabeled one, the chemical and biological properties are the same, with one important exception: because of the increased mass of the heavy isotope, any bond involving the heavy isotope and another atom will be stronger than the same bond between the light isotope and that atom. Accordingly, the incorporation of an isotope at a site of metabolism or enzymatic transformation will slow said reactions potentially altering the pharmacokinetic profile or efficacy relative to the non-isotopic compound.
Compounds
Suitable groups for X, R 1 , and Z in compounds of Formula (I) are independently selected. The described embodiments of the present invention may be combined. Such combination is contemplated and within the scope of the present invention. For example, it is contemplated that embodiments for any of X, R 1 , and Z can be combined with embodiments defined for any other of X, R 1 , and Z.
Embodiments of Formula (I)
One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
Z is CH or N; or
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is hydrogen;
Z is CR 2 ; and
R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
m is 4, 5, or 6; and
n is 1 or 2;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent;
when X is CY 1 and Y 1 is hydrogen; R 1 is NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is R 3 phenyl; the phenyl is not substituted at the para position with SO 2 R 4 or SO 2 NHR 4 .
In one embodiment of Formula (I), X is N or CY 1 . In another embodiment of Formula (I), X is N. In another embodiment of Formula (I), X is CY 1 .
In one embodiment of Formula (I), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (I), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (I), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (I), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (I), Z is CH or N; R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH or N; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
In one embodiment of Formula (I), Z is CH; R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is CH; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
In one embodiment of Formula (I), Z is N; R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 NHC(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is C(O)NH(CH 2 ) n R 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is NHC(O)(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is C(O)NH(CH 2 ) m R 3x ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 C(O)NHR 3 ; and R 2 is hydrogen. In another embodiment of Formula (I), Z is N; R 1 is CH 2 NHC(O)R 3 ; and R 2 is hydrogen.
In one embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NHR 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)R 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) n R 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) n R 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) m R 3x . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 C(O)NHR 3 . In another embodiment of Formula (I), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)R 3 .
In one embodiment of Formula (I), m is 4, 5, or 6. In another embodiment of Formula (I), m is 4. In another embodiment of Formula (I), m is 5. In another embodiment of Formula (I), m is 6.
In one embodiment of Formula (I), n is 1 or 2. In another embodiment of Formula (I), n is 1. In another embodiment of Formula (I), n is 2.
In one embodiment of Formula (I), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (I), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (I), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (I), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (I), R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 3x is heterocyclyl; wherein each R 3x heterocycyl is substituted with C(O)R 4 , or CO(O)R 4 .
In one embodiment of Formula (I), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (I), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (I), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (I), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (I), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (I), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (I), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (I), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (I), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (I), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (I)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and Z is CH or N; or
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen F, Cl, Br, and I;
R 1 is hydrogen;
Z is CR 2 ; and
R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , CH 2 C(O)NHR 3 ; and CH 2 NHC(O)R 3 ; and
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 3x is independently heterocyclyl; wherein each R 3x heterocyclyl is substituted with one substituents independently selected from the group consisting of C(O)R 4 , CO(O)R 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 2 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 2 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl;
R 11 at each occurrence, is alkyl;
m is 4, or 5; and
n is 1;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent;
when X is CY 1 and Y 1 is hydrogen; R 1 is NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is R 3 phenyl; the phenyl is not substituted at the para position with SO 2 R 4 or SO 2 NHR 4 .
Still another embodiment pertains to compounds having Formula (I), which includes Examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 436, 437, 438, 439, 440, 441, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 462, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 486, 487, 488, 489, 490, 491, 492, 493, 494, 495, 496, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 564, 565, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 621, 622, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 673, 674, 675, 676, 677, 678, 679, 680, 681, 682, 683, 684, 685, 686, 687, 688, 689, 690, 691, 692, 693, 694, 695, 696, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 709, 710, 711, 712, 713, 714, 715, 716, 717, 718, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, 731, 732, 733, 734, 735, 736, 737, 738, 739, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 754, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 810, 811, 812, 813, 814, 815, 816, 817, 818, 819, 820, 821, 822, 823, 824, 825, 826, 827, 828, 829, 830, 831, 832, 833, 834, 835, 836, 837, 838, 839, 840, 841, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, 854, 855, 856, and pharmaceutically acceptable salts thereof
Embodiments of Formula (II)
In another aspect, the present invention provides compounds of Formula (II)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (II) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (II), X is N or CY 1 . In another embodiment of Formula (II), X is N. In another embodiment of Formula (II), X is CY 1 .
In one embodiment of Formula (II), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (II), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (II), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (II), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (II), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (II), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (II), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (II), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (II), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (II), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (II), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (II), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (II), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (II), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (II), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (II), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (II), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (II), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (II)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (II), which includes Example 2; and pharmaceutically acceptable salts thereof.
Embodiments of Formula (III)
In another aspect, the present invention provides compounds of Formula (III)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described in Formula (I) herein.
One embodiment pertains to compounds of Formula (III) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (III), X is N or CY 1 . In another embodiment of Formula (III), X is N. In another embodiment of Formula (III), X is CY 1 .
In one embodiment of Formula (III), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (III), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (III), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (III), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (III), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (III), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (III), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (III), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (III), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (III), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (III), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (III), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (III), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (III), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (III), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (III), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (III), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (III), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (III)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (III), which includes Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 89, 106, 109, 110, 111, 112, 113, 396, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (IV)
In another aspect, the present invention provides compounds of Formula (IV)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (IV) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (IV), X is N or CY 1 . In another embodiment of Formula (IV), X is N. In another embodiment of Formula (IV), X is CY 1 .
In one embodiment of Formula (IV), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IV), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IV), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IV), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IV), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IV), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IV), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IV), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IV), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (IV), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IV), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IV), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IV), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (IV), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , (C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IV), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IV), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (IV), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IV), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IV)









X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (IV), which includes Examples 118, 216, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 243, 280, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 302, 303, 306, 307, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 364, 366, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 404, 407, 424, 425, 426, 427, 428, 429, 430, 431, 432, 433, 434, 435, 438, 439, 442, 443, 444, 445, 446, 447, 448, 449, 450, 451, 452, 453, 454, 455, 456, 457, 458, 459, 460, 461, 486, 487, 496, 564, 565, 673, 674, 675, 689, 690, 691, 692, 693, 694, 695, 696, 709, 710, 711, 712, 713, 714, 715, 716, 719, 720, 721, 722, 723, 724, 725, 726, 727, 728, 729, 730, and pharmaceutically acceptable salts thereof
Embodiments of Formula (V)
In another aspect, the present invention provides compounds of Formula (V)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (V) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl;
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (V), X is N or CY 1 . In another embodiment of Formula (V), X is N. In another embodiment of Formula (V), X is CY 1 .
In one embodiment of Formula (V), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (V), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (V), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (V), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (V), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (V), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (V), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (V), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (V), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (V), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (V), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (V), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (V), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (V), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (V), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (V), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (V), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (V), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (V)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (V), which include Examples 59, 60, 274, 275, 276, 277, 278, 279, 360, 362, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (VI)
In another aspect, the present invention provides compounds of Formula (VI)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (VI) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR B , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VI), X is N or CY 1 . In another embodiment of Formula (VI), X is N. In another embodiment of Formula (VI), X is CY 1 .
In one embodiment of Formula (VI), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VI), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VI), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VI), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VI), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VI), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VI), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VI), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VI), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (VI), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VI), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VI), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VI), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (VI), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VI), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VI), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (VI), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VI), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VI)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VI), which includes Examples 57, 117, 121, 138, 174, 181, 182, 185, 187, 188, 192, 193, 194, 195, 196, 197, 198, 199, 202, 203, 204, 205, 207, 208, 209, 210, 211, 212, 213, 214, 217, 218, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 241, 242, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 271, 272, 273, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 304, 305, 308, 309, 310, 311, 312, 313, 315, 316, 317, 318, 319, 320, 321, 324, 325, 326, 327, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 361, 363, 365, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 393, 394, 395, 397, 399, 400, 401, 402, 403, 405, 406, 408, 409, 410, 411, 412, 413, 414, 415, 416, 417, 418, 419, 420, 421, 422, 423, 436, 437, 440, 441, 463, 464, 465, 466, 467, 468, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, 480, 481, 482, 483, 484, 485, 488, 489, 490, 492, 493, 494, 495, 497, 498, 499, 500, 501, 502, 503, 504, 505, 506, 507, 508, 509, 510, 511, 512, 513, 514, 515, 516, 517, 518, 519, 520, 521, 522, 523, 524, 525, 526, 527, 528, 529, 530, 531, 532, 533, 534, 535, 536, 537, 538, 539, 540, 541, 542, 543, 544, 545, 546, 547, 548, 549, 550, 551, 552, 553, 554, 555, 556, 557, 558, 559, 560, 561, 562, 563, 566, 567, 568, 569, 570, 571, 572, 573, 574, 575, 576, 577, 578, 579, 580, 581, 582, 583, 584, 585, 586, 587, 588, 589, 590, 591, 592, 593, 594, 595, 596, 597, 598, 599, 600, 601, 602, 603, 604, 605, 606, 607, 608, 609, 610, 611, 612, 613, 614, 615, 616, 617, 618, 619, 620, 623, 624, 625, 626, 627, 628, 629, 630, 631, 632, 633, 634, 635, 636, 637, 638, 639, 640, 641, 642, 643, 644, 645, 646, 647, 648, 649, 650, 651, 652, 653, 654, 655, 656, 657, 658, 659, 660, 661, 662, 663, 664, 665, 666, 667, 668, 669, 670, 671, 672, 677, 682, 683, 684, 685, 686, 687, 688, 697, 698, 699, 700, 701, 702, 703, 704, 705, 706, 707, 708, 717, 718, 731, 732, 733, 734, 735, 736, 737, 738, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 755, 756, 757, 758, 759, 760, 761, 762, 763, 764, 765, 766, 767, 768, 769, 770, 771, 772, 773, 774, 775, 776, 777, 778, 779, 780, 781, 782, 783, 784, 785, 786, 787, 788, 789, 790, 791, 792, 793, 794, 795, 796, 797, 798, 799, 800, 801, 802, 803, 804, 805, 806, 807, 808, 809, 818, 821, 823, 824, 825, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (VII)
In another aspect, the present invention provides compounds of Formula (VII)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (VII) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VII), X is N or CY 1 . In another embodiment of Formula (VII), X is N. In another embodiment of Formula (VII), X is CY 1 .
In one embodiment of Formula (VII), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VII), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VII), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VII), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VII), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VII), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VII), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VII), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VII), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (VII), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VII), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VII), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VII), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (VII), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VII), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VII), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (VII), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VII), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VII)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VII), which includes Examples 52, 55, 56, 61, 75, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 108, 114, 115, 116, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 175, 176, 177, 178, 179, 180, 183, 184, 186, 189, 190, 191, 200, 201, 206, 215, 219, 240, 358, 359, 398, 462, 621, 622, 676, 810, 820, 822, 831, 832, 833, 834, 835, 836, 842, 843, 844, 845, 846, 847, 848, 849, 850, 851, 852, 853, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (VIII)
In another aspect, the present invention provides compounds of Formula (VIII)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (VIII) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , Se, S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 16 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VIII), X is N or CY 1 . In another embodiment of Formula (VIII), X is N. In another embodiment of Formula (VIII), X is CY 1 .
In one embodiment of Formula (VIII), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIII), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIII), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VIII), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VIII), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIII), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIII), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIII), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (VIII), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIII), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 16 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIII), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VIII), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (VIII), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIII), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VIII), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (VIII), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIII), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIII)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VIII), which includes Example 322, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (IX)
In another aspect, the present invention provides compounds of Formula (IX)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (IX) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; and
R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent; and
when X is CY 1 and Y 1 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl.
In one embodiment of Formula (IX), X is N or CY 1 . In another embodiment of Formula (IX), X is N. In another embodiment of Formula (IX), X is CY 1 .
In one embodiment of Formula (IX), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IX), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IX), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IX), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IX), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IX), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IX), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IX), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IX), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , and OH.
In another embodiment of Formula (IX), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IX), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , Se, S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 16 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IX), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IX), R 8 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 8 at each occurrence, is independently alkyl.
In one embodiment of Formula (IX), R 9 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IX), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IX), R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 10 at each occurrence, is independently haloalkyl or alkyl.
In one embodiment of Formula (IX), R 11 at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IX), R 11 at each occurrence, is independently alkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IX)









X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, substituent independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, or two substituents independently selected from the group consisting of R 8 , OR 8 , CNF, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 6 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, substituent independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, or three substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of haloalkyl, and alkyl; and
R 11 at each occurrence, is alkyl;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent; and
when X is CY 1 and Y 1 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl.
Still another embodiment pertains to compounds having Formula (IX), which includes Examples 53, 54, 76, 314, 323, 491, and pharmaceutically acceptable salts thereof.
Embodiments of Formula (IA)
One embodiment, therefore, pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 38 , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
Z is CH, C—F, C—Cl, C—Br, C—I or N; or
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 1 is hydrogen, F, Cl, Br, or I;
Z is CR 2 ; and
R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I;
R 11 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
m is 4, 5, or 6; and
n is 1 or 2;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent;
when X is CY 1 and Y 1 is hydrogen; R 1 is NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is R 3 phenyl; the phenyl is not substituted at the para position with SO 2 R 4 or SO 2 NHR 4 .
In one embodiment of Formula (IA), X is N or CY 1 . In another embodiment of Formula (IA), X is N. In another embodiment of Formula (IA), X is CY 1 .
In one embodiment of Formula (IA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IA), Z is CH, C—F, C—Cl, C—Br, C—I or N; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is NHC(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH or N; and R 1 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is NHC(O)R 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is NHC(O)(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is C(O)NH(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is NHC(O)(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH or N; and R 1 is C(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH or N; and R 1 is CH 2 C(O)NHR 3 . In another embodiment of Formula (IA), Z is CH or N; and R 1 is CH 2 NHC(O)R 3 .
In one embodiment of Formula (IA), Z is CH; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is NHC(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH; and R 1 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is NHC(O)R 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is NHC(O)(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is C(O)NH(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is NHC(O)(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH; and R 1 is C(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is CH; and R 1 is CH 2 C(O)NHR 3 . In another embodiment of Formula (IA), Z is CH; and R 1 is CH 2 NHC(O)R 3 .
In one embodiment of Formula (IA), Z is N; and R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 . In another embodiment of Formula (IA), Z is N; and R 1 is NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is N; and R 1 is NHC(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is N; and R 1 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (IA), Z is N; and R 1 is NHC(O)R 3 . In another embodiment of Formula (IA), Z is N; and R 1 is NHC(O)(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is N; and R 1 is C(O)NH(CH 2 ) n R 3 . In another embodiment of Formula (IA), Z is N; and R 1 is NHC(O)(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is N; and R 1 is C(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), Z is N; and R 1 is CH 2 C(O)NHR 3 . In another embodiment of Formula (IA), Z is N; and R 1 is CH 2 NHC(O)R 3 .
In one embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NHR 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)NHR 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)R 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) n R 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) n R 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is NHC(O)(CH 2 ) m R 3x . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is C(O)NH(CH 2 ) m R 3x . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 C(O)NHR 3 . In another embodiment of Formula (IA), R 1 is hydrogen; Z is CR 2 ; and R 2 is CH 2 NHC(O)R 3 .
In one embodiment of Formula (IA), m is 4, 5, or 6. In another embodiment of Formula (IA), m is 4. In another embodiment of Formula (IA), m is 5. In another embodiment of Formula (IA), m is 6.
In one embodiment of Formula (IA), n is 1 or 2. In another embodiment of Formula (IA), n is 1. In another embodiment of Formula (IA), n is 2.
In one embodiment of Formula (IA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , SO 2 R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , SO 2 R 4 , OR 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IA), R 3x is independently selected from the group consisting of phenyl and heterocyclyl; wherein each R 3x phenyl and heterocycyl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 3x is heterocyclyl; wherein each R 3x heterocycyl is substituted with C(O)R 4 , or CO(O)R 4 .
In one embodiment of Formula (IA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (IA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (IA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, and Cl.
In one embodiment of Formula (IA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IA), R 10 at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (IA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IA), R 11 , at each occurrence, is independently alkyl.
In another embodiment of Formula (IA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 1 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , NHC(O)(CH 2 ) n R 3 , C(O)NH(CH 2 ) n R 3 , NHC(O)(CH 2 ) m R 3x , C(O)NH(CH 2 ) m R 3x , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
Z is CH, C—F, or N; or
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, and Cl;
R 1 is hydrogen;
Z is CR 2 ; and
R 2 is independently selected from the group consisting of NHC(O)NHR 3 , NHC(O)NH(CH 2 ) m R 3x , CH 2 NHC(O)NHR 3 , NHC(O)R 3 , CH 2 C(O)NHR 3 , and CH 2 NHC(O)R 3 ; and
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 3x is heterocyclyl; wherein the R 3x heterocyclyl is substituted with one, two, three or four substituents independently selected from the group consisting of C(O)R 4 , CO(O)R 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F;
R 11 at each occurrence, is independently cycloalkyl or alkyl;
m is 4, or 5; and
n is 1;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent;
when X is CY 1 and Y 1 is hydrogen; R 1 is NHC(O)R 3 ; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenylmethoxy or 3-fluorophenoxy;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is furanyl; the R 3 furanyl is not substituted with benzyl, or 3-fluorophenyl methyl;
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is thienyl; the R 3 thienyl is not substituted with phenoxy, 3-fluorophenoxy, or 3-chlorophenoxy; and
when X is CY 1 and Y 1 is hydrogen; R 1 is C(O)NH(CH 2 ) n R 3 ; n is 1; R 2 is hydrogen; and R 3 is R 3 phenyl; the phenyl is not substituted at the para position with SO 2 R 4 or SO 2 NHR 4 .
Still another embodiment pertains to compounds having Formula (IA), which includes
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; 4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide; N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide; N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(moipholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(moipholin-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate; 4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]butyl}urea; 1-{4-[1-(cyclopentylcarbonyl)piperidin-4-yl]butyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]piperidin-4-yl}butyl)urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(morpholin-4-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]butyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]butyl}urea; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(morpholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-6-ylurea; 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl)[3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(moipholin-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide; 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide; 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-[4-(1-benzoylpiperidin-4-yl)butyl]-3-imidazo[1,2-a]pyridin-7-ylurea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate; tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate; tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide; 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate; tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide; 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide; 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide; 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate; tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea; 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide; 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea; 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea; tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate; 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide; 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide; tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide; 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide; 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide; 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide; propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide; 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; tert-butyl 4-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide; 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide; 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea; 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide; 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide; 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate; 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide; 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}acetamide; tert-butyl 4-{4-[(imidazo[1,2-b]pyridazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide; 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; 2-(imidazo[1,2-a]pyridin-6-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide; N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide; 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide; 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide; 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide; N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-[(3-chloroimidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(cyclopentylacetyl)amino]benzamide; N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; 2-(imidazo[1,2-a]pyridin-7-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide; 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide; N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide; N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide; 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide; 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide; 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide; 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide; 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 4-[(cyclopentylacetyl)amino]-N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide; N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide; 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide; 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; and pharmaceutically acceptable salts thereof. Still another embodiment pertains to compounds of Formula (IA) selected from the group consisting of 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide; 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (HA)
In another aspect, the present invention provides compounds of Formula (IIA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (IA).
One embodiment pertains to compounds of Formula (IIA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (IIA), X is N or CY 1 . In another embodiment of Formula (IIA), X is N. In another embodiment of Formula (IIA), X is CY 1 .
In one embodiment of Formula (IIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IIA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IIA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (IIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R, C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IIA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IIA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (IIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IIA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (IIA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IIA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (IIA), which include
4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; and pharmaceutically acceptable salts thereof

Embodiments of Formula (IIIA)
In another aspect, the present invention provides compounds of Formula (IIIA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described in Formula (IA) herein.
One embodiment pertains to compounds of Formula (IIIA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (IIIA), X is N or CY 1 . In another embodiment of Formula (IIIA), X is N. In another embodiment of Formula (IIIA), X is CY 1 .
In one embodiment of Formula (IIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IIIA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IIIA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IIIA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IIIA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (IIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IIIA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IIIA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (IIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IIIA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IIIA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (IIIA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IIIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IIIA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IIIA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (IIIA), which include
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(morpholin-4-yl)ethyl]benzamide; N-(1-hydroxy-2-methylpropan-2-yl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-benzyl-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-(cyclopentylmethyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(piperidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenoxyethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(pyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(propan-2-yloxy)ethyl]benzamide; N-(2-hydroxy-2-methylpropyl)-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[2-(2-oxopyrrolidin-1-yl)ethyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydrofuran-2-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-propylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(morpholin-4-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-phenylbenzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-methylbutyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-[3-(2-oxopyrrolidin-1-yl)propyl]benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-4-ylmethyl)benzamide; 4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; N-[(1,1-dioxidotetrahydrothiophen-3-yl)methyl]-4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydrofuran-3-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(moipholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(ethoxyacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(1-methylpiperidin-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)urea; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}phenyl)-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea; 2-ethoxy-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(moipholin-4-yl)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-2-(2-methoxyethoxy)acetamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3-methoxy-2-methylpropanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; 4,4,4-trifluoro-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}butanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-pyran-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-4-methylpentanamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1-methylpiperidine-4-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide; N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-1,4-dioxane-2-carboxamide; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea; 1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (IVA)
In another aspect, the present invention provides compounds of Formula (IVA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (IA).
One embodiment pertains to compounds of Formula (IVA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (IVA), X is N or CY 1 . In another embodiment of Formula (IVA), X is N. In another embodiment of Formula (IVA), X is CY 1 .
In one embodiment of Formula (IVA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (WA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (WA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (WA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IVA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (WA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IVA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (WA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (WA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IVA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (WA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (WA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (WA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IVA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , Se, S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (WA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IVA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (WA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IVA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (WA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (IVA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , (CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IVA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IVA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IVA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (IVA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (WA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IVA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IVA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (IVA), which include
2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(moipholin-4-ylacetyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; 1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate; tert-butyl (3R)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate; N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide; 1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}phenyl)urea; tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate; tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate; 1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]phenyl}urea; 1-{4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-4-ylacetyl)pyrrolidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea; 2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide; 1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[(1-benzoylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]azetidin-3-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]oxy}phenyl)urea; 1-(4-{[1-(1,4-dioxan-2-ylcarbonyl)azetidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]oxy}phenyl)urea; 1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4[(1-benzoylpiperidin-4-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)phenyl]urea; 1-(4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylazetidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(propan-2-yloxy)acetyl]azetidin-3-yl}phenyl)urea; 1-{4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]azetidin-3-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea; 2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide; tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea; 1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}oxy)phenyl]urea; 1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(phenylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3-fluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(2,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,4-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{[1-(3,5-difluorobenzoyl)piperidin-4-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea; tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate; 1-(4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-oxo-2,3-dihydro-1H-inden-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-3-ylacetyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea; 1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}phenyl)urea; 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)phenyl]urea; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (VA)
In another aspect, the present invention provides compounds of Formula (VA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (IA).
One embodiment pertains to compounds of Formula (VA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VA), X is N or CY 1 . In another embodiment of Formula (VA), X is N. In another embodiment of Formula (VA), X is CY 1 .
In one embodiment of Formula (VA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 ,
In one embodiment of Formula (VA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (VA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR K C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (VA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (VA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VA), which include
4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide; 2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide; 3-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)propanamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(propan-2-yloxy)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydrofuran-2-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide; N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-3-phenylpropanamide; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea; 1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (VIA)
In another aspect, the present invention provides compounds of Formula (VIA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (IA).
One embodiment pertains to compounds of Formula (VIA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VIA), X is N or CY 1 . In another embodiment of Formula (VIA), X is N. In another embodiment of Formula (VIA), X is CY 1 .
In one embodiment of Formula (VIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VIA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (VIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VIA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (VIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VIA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (VIA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VIA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VIA), which include
2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4S)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 2-{(4R)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(1,2-oxazol-3-ylacetyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(5-methyl-1,2-oxazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](1,3-thiazol-4-ylacetyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; 2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide; tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-(tetrahydrofuran-2-yl)propanoyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-methylpentanoyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 2-{5-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide; 2-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[(4R)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; 5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide; 2-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5S)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{(5R)-2-oxo-5-[(propan-2-yloxy)methyl]-1,3-oxazolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide; 5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-5-ethyl-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methoxy-3,3-dimethylcyclohexyl)methyl]-5-methyl-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-(1-ethyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(1,1-dioxidotetrahydrothiophen-3-yl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate; 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide; 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide; 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate; tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide; tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate; 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide; 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide; 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide; 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide; 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide; propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide; 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide; 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; 5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methyl-2-phenylpropanoyl)pyrrolidin-3-yl]benzamide; 4-{1-[difluoro(phenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide; 4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate; 5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-propanoylpyrrolidin-3-yl)thiophene-2-carboxamide; 5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-carboxamide; 5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-methoxyphenyl)acetyl]amino}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(phenylacetyl)amino]benzamide; 4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; 2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}benzamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-3-methoxybenzamide; 4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-methyl-2-(piperazin-1-yl)propanoyl]piperidin-4-yl}thiophene-2-carboxamide; N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-2-methoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide; 5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1 H-pyrazol-4-yl]thiophene-2-carboxamide; 5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-oxatricyclo[3.3.1.1˜3,7˜]dec-1-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-phenylpropanoyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide; 5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide; 4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbut-2-enoyl)piperidin-4-yl]benzamide; 4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(methoxymethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-methylpropyl)sulfonyl]acetyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-phenoxypropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)piperidin-4-yl]benzamide; 4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxyphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylphenyl)acetyl]piperidin-4-yl}benzamide; 4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxycyclohexyl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-4-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-7-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(quinoxalin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(isoquinolin-8-ylcarbonyl)piperidin-4-yl]benzamide; 4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-yl)benzamide; 4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxy-6-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-methyl-5-(propan-2-yl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide; 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide; 5-{1-[2,2-dimethyl-3-(piperazin-1-yl)propyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-amino-2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxythiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-4-yl)benzamide; 4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)benzamide; 4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-yl)benzamide; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (VII)
In another aspect, the present invention provides compounds of Formula (VIIA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (IA).
One embodiment pertains to compounds of Formula (VIIA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VIIA), X is N or CY 1 . In another embodiment of Formula (VIIA), X is N. In another embodiment of Formula (VIIA), X is CY 1 .
In one embodiment of Formula (VIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VIIA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIIA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (VIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIIA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VIIA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (VIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VIIA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (VIIA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VIIA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VIIA), which include
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide; 4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide; 2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(moipholin-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[3-(tetrahydrofuran-2-yl)propanoyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-[1-(cyclopentylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{1-[(2-methoxyethoxy)acetyl]-1,2,3,6-tetrahydropyridin-4-yl}benzamide; 4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]-1,2,3,6-tetrahydropyridin-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(2-oxo-5-phenyl-1,3-oxazolidin-3-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methyl-1,3-thiazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(3-methyl-1,2-oxazol-5-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[3-(3-chloro-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(3-methoxy-1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(3,5-dimethyl-1,2-oxazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; 2-{[3-(3,5-dimethyl-1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(4-methyl-1,3-thiazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1H-tetrazol-5-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-5-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(1,2-oxazol-3-ylacetyl)(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1,2-oxazol-4-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-2-ylmethyl)[3-(1,3-thiazol-2-yl)propanoyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylmethyl)(tetrahydro-2H-pyran-4-ylcarbonyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydrofuran-3-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methoxypropanoyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-3-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydro-2H-pyran-4-ylcarbonyl)(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl) [(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2R)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(3-methoxypropanoyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{(tetrahydrofuran-3-ylcarbonyl)[(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2S)-tetrahydrofuran-2-ylmethyl](tetrahydro-2H-pyran-4-ylcarbonyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl](tetrahydro-2H-pyran-4-ylmethyl)amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2R)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2R)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(2-methoxyethyl)carbamoyl][(2S)-tetrahydrofuran-2-ylmethyl]amino}-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-({[2-(propan-2-yloxy)ethyl]carbamoyl}[(2S)-tetrahydrofuran-2-ylmethyl]amino)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-3-ylmethyl)amino]-1,3-thiazole-5-carboxamide; 2-[5-(4-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 4-{[1-(cyclopropylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-[(1-butanoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3-methoxy-2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropanoyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(cyclohexylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2R)-2-hydroxybutyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[(1-methyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,3-dimethyl-1H-pyrazol-4-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-{[3-(1-methyl-1H-pyrrol-2-yl)propanoyl](tetrahydrofuran-2-ylmethyl)amino}-1,3-thiazole-5-carboxamide; 2-{[(1,5-dimethyl-1H-pyrazol-3-yl)acetyl](tetrahydrofuran-2-ylmethyl)amino}-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(tetrahydrofuran-2-ylmethyl)(1,3-thiazol-4-ylacetyl)amino]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; 5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; 5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 5-[1-(phenylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide; 4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide; and

pharmaceutically acceptable salts thereof


Embodiments of Formula (VIIIA)
In another aspect, the present invention provides compounds of Formula (VIII)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (VIIIA) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , x NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
In one embodiment of Formula (VIIIA), X is N or CY 1 . In another embodiment of Formula (VIIIA), X is N. In another embodiment of Formula (VIIIA), X is CY 1 .
In one embodiment of Formula (VIIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (VIIIA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (VIIIA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (VIIIA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (VIIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIIIA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (VIIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (VIIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (VIIIA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (VIIIA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIIA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (VIIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (VIIIA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (VIIIA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (VIIIA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (VIIIA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (VIIIA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (VIIIA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the proviso that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent.
Still another embodiment pertains to compounds having Formula (VIIIA), which include
tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate; and pharmaceutically acceptable salts thereof

Embodiments of Formula (IXA)
In another aspect, the present invention provides compounds of Formula (IXA)









and pharmaceutically acceptable salts thereof; wherein X and R 3 are as described herein for Formula (I).
One embodiment pertains to compounds of Formula (IX) or pharmaceutically acceptable salts thereof;
wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent; and
when X is CY 1 and Y 1 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl.
In one embodiment of Formula (IXA), X is N or CY 1 . In another embodiment of Formula (IXA), X is N. In another embodiment of Formula (IXA), X is CY 1 .
In one embodiment of Formula (IXA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, alkyl, alkoxy, haloalkyl, hydroxyalkyl, OH, CN, F, Cl, Br, and I. In another embodiment of Formula (IXA), X is CY 1 ; and Y 1 is independently selected from the group consisting of hydrogen, Cl, Br, and I. In another embodiment of Formula (IXA), X is CY 1 ; and Y 1 is Cl. In another embodiment of Formula (IXA), X is CY 1 ; and Y 1 is hydrogen.
In one embodiment of Formula (IXA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of alkyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, C(O)H, C(O)OH, C(N)NH 2 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , OR 4 , SR 4 , S(O)R 4 , SO 2 R 4 , C(O)R 4 , CO(O)R 4 , OC(O)R 4 , OC(O)OR 4 , NH 2 , NHR 4 , N(R 4 ) 2 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NR 4 S(O) 2 R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , NHC(O)NH 2 , NHC(O)NHR 4 , NHC(O)N(R 4 ) 2 , NR 4 C(O)NHR 4 , NR 4 C(O)N(R 4 ) 2 , C(O)NH 2 , C(O)NHR 4 , C(O)N(R 4 ) 2 , C(O)NHOH, C(O)NHOR 4 , C(O)NHSO 2 R 4 , C(O)NR 4 SO 2 R 4 , SO 2 NH 2 , SO 2 NHR 4 , SO 2 N(R 4 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 4 , C(N)N(R 4 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IXA), R 3 is phenyl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , and C(O)NHR 4 ; and wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I. In another embodiment of Formula (IXA), R 3 is 5-6 membered heteroaryl; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 3 is thienyl; wherein each R 3 thienyl is substituted with one, two, or three substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)NHR 4 , C(O)NHR 4 , F, Cl, Br and I.
In one embodiment of Formula (IXA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (IXA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (IXA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (IXA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (IXA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IXA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (IXA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (IXA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (IXA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (IXA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (IXA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (IXA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (IXA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (IXA)









wherein
X is N or CY 1 ;
Y 1 is independently selected from the group consisting of hydrogen, F, Cl, Br, and I;
R 3 is independently selected from the group consisting of phenyl and 5-6 membered heteroaryl; wherein each R 3 phenyl is substituted at the para position with one substituent independently selected from the group consisting of R 4 , OR 4 , SO 2 R 4 , C(O)R 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHS(O) 2 R 4 , NHC(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I; wherein each R 3 phenyl is optionally additionally substituted with one substituent independently selected from the group consisting of F, Cl, Br and I; wherein each R 3 5-6 membered heteroaryl is substituted with one, two, three or four substituents independently selected from the group consisting of R 4 , C(O)R 4 , NHR 4 , NHC(O)R 4 , NR 4 C(O)R 4 , NHC(O)OR 4 , NR 4 C(O)OR 4 , C(O)NHR 4 , F, Cl, Br and I;
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl;
with the provisos that
when X is CY 1 and Y 1 is hydrogen; and R 3 is thiazolyl; the R 3 thiazolyl is substituted with one substituent; and
when X is CY 1 and Y 1 is hydrogen; and R 3 is phenyl; the R 3 phenyl is not substituted at the para position with phenyl.
Still another embodiment pertains to compounds having Formula (IXA), which include
2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide; tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate; tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate; tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate; and pharmaceutically acceptable salts thereof.

Embodiments of Formula (XA)
In another aspect, the present invention provides compounds of Formula (XA)









and pharmaceutically acceptable salts thereof wherein R 4 is as described herein for Formula (IA)
One embodiment pertains to compounds of Formula (XA) or pharmaceutically acceptable salts thereof;
wherein
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I;
R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I; and
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I; and
R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl.
In one embodiment of Formula (XA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , SR 5 , S(O)R 5 , SO 2 R 5 , C(O)R 5 , CO(O)R 5 , OC(O)R 5 , OC(O)OR 5 , NH 2 , NHR 5 , N(R 5 ) 2 , NHC(O)R 5 , NR 5 C(O)R 5 , NHS(O) 2 R 5 , NR 5 S(O) 2 R 5 , NHC(O)OR 5 , NR 5 C(O)OR 5 , NHC(O)NH 2 , NHC(O)NHR 5 , NHC(O)N(R 5 ) 2 , NR 5 C(O)NHR 5 , NR 5 C(O)N(R 5 ) 2 , C(O)NH 2 , C(O)NHR 5 , C(O)N(R 5 ) 2 , C(O)NHOH, C(O)NHOR 5 , C(O)NHSO 2 R 5 , C(O)NR 5 SO 2 R 5 , SO 2 NH 2 , SO 2 NHR 5 , SO 2 N(R 5 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 5 , C(N)N(R 5 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, cycloalkenyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SR 6 , S(O)R 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , OC(O)R 6 , OC(O)OR 6 , NH 2 , NHR 6 , N(R 6 ) 2 , NHC(O)R 6 , NR 6 C(O)R 6 , NHS(O) 2 R 6 , NR 6 S(O) 2 R 6 , NHC(O)OR 6 , NR 6 C(O)OR 6 , NHC(O)NH 2 , NHC(O)NHR 6 , NHC(O)N(R 6 ) 2 , NR 6 C(O)NHR 6 , NR 6 C(O)N(R 6 ) 2 , C(O)NH 2 , C(O)NHR 6 , C(O)N(R 6 ) 2 , C(O)NHOH, C(O)NHOR 6 , C(O)NHSO 2 R 6 , C(O)NR 6 SO 2 R 6 , SO 2 NH 2 , SO 2 NHR 6 , SO 2 N(R 6 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 6 , C(N)N(R 6 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (XA), R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , C(O)N(R 6 ) 2 , OH, and F.
In another embodiment of Formula (XA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 5 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , SR 7 , S(O)R 7 , SO 2 R 7 , C(O)R 7 , CO(O)R 7 , OC(O)R 7 , OC(O)OR 7 , NH 2 , NHR 7 , N(R 7 ) 2 , NHC(O)R 7 , NR 7 C(O)R 7 , NHS(O) 2 R 7 , NR 7 S(O) 2 R 7 , NHC(O)OR 7 , NR 7 C(O)OR 7 , NHC(O)NH 2 , NHC(O)NHR 7 , NHC(O)N(R 7 ) 2 , NR 7 C(O)NHR 7 , NR 7 C(O)N(R 7 ) 2 , C(O)NH 2 , C(O)NHR 7 , C(O)N(R 7 ) 2 , C(O)NHOH, C(O)NHOR 7 , C(O)NHSO 2 R 7 , C(O)NR 7 SO 2 R 7 , SO 2 NH 2 , SO 2 NHR 7 , SO 2 N(R 7 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 7 , C(N)N(R 7 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 5 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , SR 8 , S(O)R 8 , SO 2 R 8 , C(O)R 8 , CO(O)R 8 , OC(O)R 8 , OC(O)OR 8 , NH 2 , NHR 8 , N(R 8 ) 2 , NHC(O)R 8 , NR 8 C(O)R 8 , NHS(O) 2 R 8 , NR 8 S(O) 2 R 8 , NHC(O)OR 8 , NR 8 C(O)OR 8 , NHC(O)NH 2 , NHC(O)NHR 8 , NHC(O)N(R 8 ) 2 , NR 8 C(O)NHR 8 , NR 8 C(O)N(R 8 ) 2 , C(O)NH 2 , C(O)NHR 8 , C(O)N(R 8 ) 2 , C(O)NHOH, C(O)NHOR 8 , C(O)NHSO 2 R 8 , C(O)NR 8 SO 2 R 8 , SO 2 NH 2 , SO 2 NHR 8 , SO 2 N(R 8 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 8 , C(N)N(R 8 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (XA), R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , and OH; wherein each R 5 aryl and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I.
In one embodiment of Formula (XA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SR 9 , S(O)R 9 , SO 2 R 9 , C(O)R 9 , CO(O)R 9 , OC(O)R 9 , OC(O)OR 9 , NH 2 , NHR 9 , N(R 9 ) 2 , NHC(O)R 9 , NR 9 C(O)R 9 , NHS(O) 2 R 9 , NR 9 S(O) 2 R 9 , NHC(O)OR 9 , NR 9 C(O)OR 9 , NHC(O)NH 2 , NHC(O)NHR 9 , NHC(O)N(R 9 ) 2 , NR 9 C(O)NHR 9 , NR 9 C(O)N(R 9 ) 2 , C(O)NH 2 , C(O)NHR 9 , C(O)N(R 9 ) 2 , C(O)NHOH, C(O)NHOR 9 , C(O)NHSO 2 R 9 , C(O)NR 9 SO 2 R 9 , SO 2 NH 2 , SO 2 NHR 9 , SO 2 N(R 9 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 9 , C(N)N(R 9 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , SR 10 , S(O)R 10 , SO 2 R 10 , C(O)R 10 , CO(O)R 10 , OC(O)R 10 , OC(O)OR 10 , NH 2 , NHR 10 , N(R 10 ) 2 , NHC(O)R 10 , NR 10 C(O)R 10 , NHS(O) 2 R 10 , NR 10 S(O) 2 R 10 , NHC(O)OR 10 , NR 10 C(O)OR 10 , NHC(O)NH 2 , NHC(O)NHR 10 , NHC(O)N(R 10 ) 2 , NR 10 C(O)NHR 10 , NR 10 C(O)N(R 10 ) 2 , C(O)NH 2 , C(O)NHR 10 , C(O)N(R 10 ) 2 , C(O)NHOH, C(O)NHOR 10 , C(O)NHSO 2 R 10 , C(O)NR 10 SO 2 R 10 , SO 2 NH 2 , SO 2 NHR 10 , SO 2 N(R 10 ) 2 , C(O)H, C(O)OH, C(N)NH 2 , C(N)NHR 10 , C(N)N(R 10 ) 2 , CNOH, CNOCH 3 , OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (XA), R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , CN, F, Cl, Br and I.
In one embodiment of Formula (XA), R 7 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 7 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, N 3 , NO 2 , F, Cl, Br and I; wherein each R 7 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of OH, CN, N 3 , NO 2 , F, Cl, Br and I. In another embodiment of Formula (XA), R 7 , at each occurrence, is alkyl or heterocyclyl.
In one embodiment of Formula (XA), R 8 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, and alkynyl. In another embodiment of Formula (XA), R 8 , at each occurrence, is independently alkyl.
In one embodiment of Formula (XA), R 9 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 9 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, OH, CN, NO 2 , F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , C(O)R 11 , CO(O)R 11 , OC(O)R 11 , NH 2 , NHR 11 , N(R 11 ) 2 , NHC(O)R 11 , NR 11 C(O)R 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C(O)H, C(O)OH, COH, CN, NO 2 , F, Cl, Br and I. In another embodiment of Formula (XA), R 9 at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, and alkoxy; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , and F.
In one embodiment of Formula (XA), R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl; wherein each R 10 alkyl, alkenyl, and alkynyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, F, Cl, Br and I. In another embodiment of Formula (XA), R 10 , at each occurrence, is independently heterocyclyl, cycloalkyl, alkyl, or alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F.
In one embodiment of Formula (XA), R 11 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl, alkenyl, and alkynyl. In another embodiment of Formula (XA), R 11 , at each occurrence, is independently alkyl. In another embodiment of Formula (XA), R 11 , at each occurrence, is independently cycloalkyl.
One embodiment pertains to compounds or pharmaceutically acceptable salts thereof, which are useful as inhibitors of NAMPT, the compounds having Formula (XA)









wherein
R 4 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, cycloalkyl, and 3-12 membered heterocyclyl; wherein each R 4 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 5 , OR 5 , C(O)R 5 , NHC(O)R 5 , OH, F, Cl, Br and I; wherein each R 4 aryl, cycloalkyl, and 3-12 membered heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 6 , OR 6 , SO 2 R 6 , C(O)R 6 , CO(O)R 6 , C(O)C(O)R 6 , NHC(O)R 6 , NHC(O)NHR 6 , C(O)N(R 6 ) 2 , OH, F, Cl, Br and I;
R 5 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 5 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 7 , OR 7 , OH, F, Cl, Br and I; wherein each R 5 aryl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 8 , OR 8 , CN, F, Cl, Br and I;
R 6 , at each occurrence, is independently selected from the group consisting of alkyl, alkenyl, aryl, heterocyclyl, cycloalkyl, and cycloalkenyl; wherein each R 6 alkyl and alkenyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 9 , OR 9 , SO 2 R 9 , NH 2 , N(R 9 ) 2 , OH, F, Cl, Br and I; wherein each R 6 aryl, cycloalkyl, cycloalkenyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 10 , OR 10 , C(O)R 10 , CN, F, and Cl;
R 7 , at each occurrence, is independently selected from the group consisting of alkyl, and heterocyclyl;
R 8 , at each occurrence, is independently alkyl;
R 9 , at each occurrence, is independently selected from the group consisting of alkyl, aryl, heterocyclyl, and cycloalkyl; wherein each R 9 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of aryl, alkoxy, F, Cl, Br and I; wherein each R 9 aryl, cycloalkyl, and heterocyclyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of R 11 , OR 11 , CO(O)R 11 , CN, F, Cl, Br and I;
R 10 , at each occurrence, is independently selected from the group consisting of aryl, heterocyclyl, cycloalkyl, alkyl, and alkenyl; wherein each R 10 alkyl is optionally substituted with one, two, three or four substituents independently selected from the group consisting of alkoxy, and F; and
R 11 , at each occurrence, is independently cycloalkyl or alkyl.
Still another embodiment pertains to compounds having Formula (XA), which include
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; 4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; 4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(methylsulfonyl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate; 5-{1-[(2R)-2-hydroxypropyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}benzamide; 4-[1-(cyclopropylacetyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide; 5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide; 5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]oxy}benzamide; 5-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; 4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-methoxy-2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide; tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(propan-2-yloxy)acetyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(1,4-dioxan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate; tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(2S)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-[(1-acetylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylpiperidin-4-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(propan-2-yloxy)acetyl]piperidin-4-yl}oxy)benzamide; 4-{[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]oxy}benzamide; 4-{[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(morpholin-4-ylacetyl)piperidin-4-yl]oxy}benzamide; tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate; 4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methyltetrahydro-2H-pyran-2-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide; 5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide; N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide; tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydrofuran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-3-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]furan-2-carboxamide; 5-[1-(cyclobutylmethyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methyloxetan-3-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide; 5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide; 4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide; 4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide; 5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide; 4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}benzamide; 4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-oxobutanoyl)piperidin-4-yl]benzamide; 4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]piperidin-4-yl}benzamide; 4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)piperidin-4-yl]benzamide; 4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-propanoylpiperidin-4-yl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide; 4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide; 5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide; 4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-methylbutanoyl]azetidin-3-yl}benzamide; 4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-ylcarbonyl)azetidin-3-yl]benzamide; 5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide; 4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide; 4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide; propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; 2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide; N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; 5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide; 4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)pyrrolidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)pyrrolidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]pyrrolidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]pyrrolidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide; 4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylpentanoyl)azetidin-3-yl]benzamide; 4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylbenzoyl)azetidin-3-yl]benzamide; 4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbutanoyl)azetidin-3-yl]benzamide; 4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-methoxybenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-2-ylcarbonyl)azetidin-3-yl]benzamide; 4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrimidin-4-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide; 4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-methylbenzoyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-ylcarbonyl)azetidin-3-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide; 5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide; 4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide; 5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide; 5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide; 4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; 4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethoxy)benzoyl]piperidin-4-yl}benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylacetyl)piperidin-4-yl]benzamide; N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-(trifluoromethyl)benzoyl]piperidin-4-yl}benzamide; and pharmaceutically acceptable salts thereof.

Pharmaceutical Compositions, Combination Therapies, Methods of Treatment, and Administration
Another embodiment comprises pharmaceutical compositions comprising a compound having Formula (I) and an excipient.
Still another embodiment comprises methods of treating cancer in a mammal comprising administering thereto a therapeutically acceptable amount of a compound having Formula (I).
Still another embodiment pertains to compositions for treating diseases during which NAMPT is expressed, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I).
Still another embodiment pertains to methods of treating disease in a patient during which NAMPT is expressed, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I).
Still another embodiment pertains to compositions for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I).
Still another embodiment pertains to methods of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I).
Still another embodiment pertains to compositions for treating diseases during which NAMPT is expressed, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
Still another embodiment pertains to methods of treating disease in a patient during which NAMPT is expressed, said methods comprising administering to the patient a therapeutically effective amount of a compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
Still another embodiment pertains to compositions for treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia, said compositions comprising an excipient and a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
Still another embodiment pertains to methods of treating inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia in a patient, said methods comprising administering to the patient a therapeutically effective amount of the compound having Formula (I) and a therapeutically effective amount of one additional therapeutic agent or more than one additional therapeutic agent.
Metabolites of compounds having Formula (I), produced by in vitro or in vivo metabolic processes, may also have utility for treating diseases associated with NAMPT.
Certain precursor compounds which may be metabolized in vitro or in vivo to form compounds having Formula (I) may also have utility for treating diseases associated with NAMPT.
Compounds having Formula (I) may exist as acid addition salts, basic addition salts or zwitterions. Salts of the compounds are prepared during isolation or following purification of the compounds. Acid addition salts of the compounds are those derived from the reaction of the compounds with an acid. For example, the acetate, adipate, alginate, bicarbonate, citrate, aspartate, benzoate, benzenesulfonate, bisulfate, butyrate, camphorate, camphorsufonate, digluconate, formate, fumarate, glycerophosphate, glutamate, hemisulfate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, lactobionate, lactate, maleate, mesitylenesulfonate, methanesulfonate, naphthylenesulfonate, nicotinate, oxalate, pamoate, pectinate, persulfate, phosphate, picrate, propionate, succinate, tartrate, thiocyanate, trichloroacetic, trifluoroacetic, para-toluenesulfonate, and undecanoate salts of the compounds are contemplated as being embraced by this invention. Basic addition salts of the compounds are those derived from the reaction of the compounds with the hydroxide, carbonate or bicarbonate of cations such as lithium, sodium, potassium, calcium, and magnesium.
The compounds having Formula (I) may be administered, for example, bucally, ophthalmically, orally, osmotically, parenterally (intramuscularly, intraperitoneally intrasternally, intravenously, subcutaneously), rectally, topically, transdermally or vaginally.
Therapeutically effective amounts of compounds having Formula (I) depend on the recipient of the treatment, the disorder being treated and the severity thereof, the composition containing the compound, the time of administration, the route of administration, the duration of treatment, the compound potency, its rate of clearance and whether or not another drug is co-administered. The amount of a compound of this invention having Formula (I) used to make a composition to be administered daily to a patient in a single dose or in divided doses is from about 0.03 to about 200 mg/kg body weight. Single dose compositions contain these amounts or a combination of submultiples thereof
Compounds having Formula (I) may be administered with or without an excipient. Excipients include, for example, encapsulating materials or additives such as absorption accelerators, antioxidants, binders, buffers, coating agents, coloring agents, diluents, disintegrating agents, emulsifiers, extenders, fillers, flavoring agents, humectants, lubricants, perfumes, preservatives, propellants, releasing agents, sterilizing agents, sweeteners, solubilizers, wetting agents and mixtures thereof
Excipients for preparation of compositions comprising a compound having Formula (I) to be administered orally in solid dosage form include, for example, agar, alginic acid, aluminum hydroxide, benzyl alcohol, benzyl benzoate, 1,3-butylene glycol, carbomers, castor oil, cellulose, cellulose acetate, cocoa butter, corn starch, corn oil, cottonseed oil, cross-povidone, diglycerides, ethanol, ethyl cellulose, ethyl laureate, ethyl oleate, fatty acid esters, gelatin, germ oil, glucose, glycerol, groundnut oil, hydroxypropylmethyl cellulose, isopropanol, isotonic saline, lactose, magnesium hydroxide, magnesium stearate, malt, mannitol, monoglycerides, olive oil, peanut oil, potassium phosphate salts, potato starch, povidone, propylene glycol, Ringer's solution, safflower oil, sesame oil, sodium carboxymethyl cellulose, sodium phosphate salts, sodium lauryl sulfate, sodium sorbitol, soybean oil, stearic acids, stearyl fumarate, sucrose, surfactants, talc, tragacanth, tetrahydrofurfuryl alcohol, triglycerides, water, and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered ophthalmically or orally in liquid dosage forms include, for example, 1,3-butylene glycol, castor oil, corn oil, cottonseed oil, ethanol, fatty acid esters of sorbitan, germ oil, groundnut oil, glycerol, isopropanol, olive oil, polyethylene glycols, propylene glycol, sesame oil, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered osmotically include, for example, chlorofluorohydrocarbons, ethanol, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered parenterally include, for example, 1,3-butanediol, castor oil, corn oil, cottonseed oil, dextrose, germ oil, groundnut oil, liposomes, oleic acid, olive oil, peanut oil, Ringer's solution, safflower oil, sesame oil, soybean oil, U.S.P. or isotonic sodium chloride solution, water and mixtures thereof. Excipients for preparation of compositions comprising a compound of this invention having Formula (I) to be administered rectally or vaginally include, for example, cocoa butter, polyethylene glycol, wax and mixtures thereof.
Compounds having Formula (I) are expected to be useful when used with alkylating agents, angiogenesis inhibitors, antibodies, antimetabolites, antimitotics, antiproliferatives, antivirals, aurora kinase inhibitors, apoptosis promoters (for example, Bcl-xL, Bcl-w and Bfl-1) inhibitors, activators of death receptor pathway, Bcr-Abl kinase inhibitors, BiTE (Bi-Specific T cell Engager) antibodies, antibody drug conjugates, biologic response modifiers, cyclin-dependent kinase inhibitors, cell cycle inhibitors, cyclooxygenase-2 inhibitors, DVDs, leukemia viral oncogene homolog (ErbB2) receptor inhibitors, growth factor inhibitors, heat shock protein (HSP)-90 inhibitors, histone deacetylase (HDAC) inhibitors, hormonal therapies, immunologicals, inhibitors of inhibitors of apoptosis proteins (IAPs), intercalating antibiotics, kinase inhibitors, kinesin inhibitors, Jak2 inhibitors, mammalian target of rapamycin inhibitors, microRNA's, mitogen-activated extracellular signal-regulated kinase inhibitors, multivalent binding proteins, non-steroidal anti-inflammatory drugs (NSAIDs), poly ADP (adenosine diphosphate)-ribose polymerase (PARP) inhibitors, platinum chemotherapeutics, polo-like kinase (Plk) inhibitors, phosphoinositide-3 kinase (PI3K) inhibitors, proteosome inhibitors, purine analogs, pyrimidine analogs, receptor tyrosine kinase inhibitors, retinoids/deltoids plant alkaloids, small inhibitory ribonucleic acids (siRNAs), topoisomerase inhibitors, ubiquitin ligase inhibitors, and the like, and in combination with one or more of these agents.
BiTE antibodies are bi-specific antibodies that direct T-cells to attack cancer cells by simultaneously binding the two cells. The T-cell then attacks the target cancer cell. Examples of BiTE antibodies include adecatumumab (Micromet MT201), blinatumomab (Micromet MT103) and the like. Without being limited by theory, one of the mechanisms by which T-cells elicit apoptosis of the target cancer cell is by exocytosis of cytolytic granule components, which include perforin and granzyme B.
SiRNAs are molecules having endogenous RNA bases or chemically modified nucleotides. The modifications do not abolish cellular activity, but rather impart increased stability and/or increased cellular potency. Examples of chemical modifications include phosphorothioate groups, 2′-deoxynucleotide, 2′-OCH 3 -containing ribonucleotides, 2′-F-ribonucleotides, 2′-methoxyethyl ribonucleotides, combinations thereof and the like. The siRNA can have varying lengths (e.g., 10-200 bps) and structures (e.g., hairpins, single/double strands, bulges, nicks/gaps, mismatches) and are processed in cells to provide active gene silencing. A double-stranded siRNA (dsRNA) can have the same number of nucleotides on each strand (blunt ends) or asymmetric ends (overhangs). The overhang of 1-2 nucleotides can be present on the sense and/or the antisense strand, as well as present on the 5′- and/or the 3′-ends of a given strand.
Multivalent binding proteins are binding proteins comprising two or more antigen binding sites. Multivalent binding proteins are engineered to have the three or more antigen binding sites and are generally not naturally occurring antibodies. The term “multispecific binding protein” means a binding protein capable of binding two or more related or unrelated targets. Dual variable domain (DVD) binding proteins are tetravalent or multivalent binding proteins binding proteins comprising two or more antigen binding sites. Such DVDs may be monospecific (i.e., capable of binding one antigen) or multispecific (i.e., capable of binding two or more antigens). DVD binding proteins comprising two heavy chain DVD polypeptides and two light chain DVD polypeptides are referred to as DVD Ig's. Each half of a DVD Ig comprises a heavy chain DVD polypeptide, a light chain DVD polypeptide, and two antigen binding sites. Each binding site comprises a heavy chain variable domain and a light chain variable domain with a total of 6 CDRs involved in antigen binding per antigen binding site.
Alkylating agents include altretamine, AMD-473, AP-5280, apaziquone, bendamustine, brostallicin, busulfan, carboquone, carmustine (BCNU), chlorambucil, CLORETAZINE® (laromustine, VNP 40101M), cyclophosphamide, decarbazine, estramustine, fotemustine, glufosfamide, ifosfamide, KW-2170, lomustine (CCNU), mafosfamide, melphalan, mitobronitol, mitolactol, nimustine, nitrogen mustard N-oxide, ranimustine, temozolomide, thiotepa, TREANDA® (bendamustine), treosulfan, trofosfamide and the like.
Angiogenesis inhibitors include endothelial-specific receptor tyrosine kinase (Tie-2) inhibitors, epidermal growth factor receptor (EGFR) inhibitors, insulin growth factor-2 receptor (IGFR-2) inhibitors, matrix metalloproteinase-2 (MMP-2) inhibitors, matrix metalloproteinase-9 (MMP-9) inhibitors, platelet-derived growth factor receptor (PDGFR) inhibitors, thrombospondin analogs, vascular endothelial growth factor receptor tyrosine kinase (VEGFR) inhibitors and the like.
Antimetabolites include ALIMTA® (pemetrexed disodium, LY231514, MTA), 5-azacitidine, XELODA® (capecitabine), carmofur, LEUSTAT® (cladribine), clofarabine, cytarabine, cytarabine ocfosfate, cytosine arabinoside, decitabine, deferoxamine, doxifluridine, eflornithine, EICAR (5-ethynyl-1-(3-D-ribofuranosylimidazole-4-carboxamide), enocitabine, ethnylcytidine, fludarabine, 5-fluorouracil alone or in combination with leucovorin, GEMZAR® (gemcitabine), hydroxyurea, ALKERAN®(melphalan), mercaptopurine, 6-mercaptopurine riboside, methotrexate, mycophenolic acid, nelarabine, nolatrexed, ocfosfate, pelitrexol, pentostatin, raltitrexed, Ribavirin, triapine, trimetrexate, S-1, tiazofurin, tegafur, TS-1, vidarabine, UFT and the like.
Antivirals include ritonavir, hydroxychloroquine and the like.
Aurora kinase inhibitors include ABT-348, AZD-1152, MLN-8054, VX-680, Aurora A-specific kinase inhibitors, Aurora B-specific kinase inhibitors and pan-Aurora kinase inhibitors and the like.
Bcl-2 protein inhibitors include AT-101 ((−)gossypol), GENASENSE® (G3139 or oblimersen (Bcl-2-targeting antisense oligonucleotide)), IPI-194, IPI-565, N-(4-(4-((4′-chloro(1,1′-biphenyl)-2-yl)methyl)piperazin-1-yl)benzoyl)-44(1R)-3-(dimethylamino)-1-((phenylsulfanyl)methyl)propyl)amino)-3-nitrobenzenesulfonamide) (ABT-737), N-(4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoyl)-4-(((1R)-3-(morpholin-4-yl)-1-((phenylsulfanyl)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)benzenesulfonamide (ABT-263), GX-070 (obatoclax) and the like.
Bcr-Abl kinase inhibitors include DASATINIB® (BMS-354825), GLEEVEC® (imatinib) and the like.
CDK inhibitors include AZD-5438, BMI-1040, BMS-032, BMS-387, CVT-2584, flavopyridol, GPC-286199, MCS-5A, PD0332991, PHA-690509, seliciclib (CYC-202, R-roscovitine), ZK-304709 and the like.
COX-2 inhibitors include ABT-963, ARCOXIA® (etoricoxib), BEXTRA® (valdecoxib), BMS347070, CELEBREX® (celecoxib), COX-189 (lumiracoxib), CT-3, DERAMAXX® (deracoxib), JTE-522, 4-methyl-2-(3,4-dimethylphenyl)-1-(4-sulfamoylphenyl-1H-pyrrole), MK-663 (etoricoxib), NS-398, parecoxib, RS-57067, SC-58125, SD-8381, SVT-2016, S-2474, T-614, VIOXX® (rofecoxib) and the like.
EGFR inhibitors include ABX-EGF, anti-EGFR immunoliposomes, EGF-vaccine, EMD-7200, ERBITUX® (cetuximab), HR3, IgA antibodies, IRESSA® (gefitinib), TARCEVA® (erlotinib or OSI-774), TP-38, EGFR fusion protein, TYKERB® (lapatinib) and the like.
ErbB2 receptor inhibitors include CP-724-714, CI-1033 (canertinib), HERCEPTIN® (trastuzumab), TYKERB® (lapatinib), OMNITARG® (2C4, petuzumab), TAK-165, GW-572016 (ionafarnib), GW-282974, EKB-569, PI-166, dHER2 (HER2 vaccine), APC-8024 (HER-2 vaccine), anti-HER/2neu bispecific antibody, B7.her2IgG3, AS HER2 trifunctional bispecfic antibodies, mAB AR-209, mAB 2B-1 and the like.
Histone deacetylase inhibitors include depsipeptide, LAQ-824, MS-275, trapoxin, suberoylanilide hydroxamic acid (SAHA), TSA, valproic acid and the like.
HSP-90 inhibitors include 17-AAG-nab, 17-AAG, CNF-101, CNF-1010, CNF-2024, 17-DMAG, geldanamycin, IPI-504, KOS-953, MYCOGRAB® (human recombinant antibody to HSP-90), NCS-683664, PU24FC1, PU-3, radicicol, SNX-2112, STA-9090 VER49009 and the like.
Inhibitors of inhibitors of apoptosis proteins include HGS1029, GDC-0145, GDC-0152, LCL-161, LBW-242 and the like.
Antibody drug conjugates include anti-CD22-MC-MMAF, anti-CD22-MC-MMAE, anti-CD22-MCC-DM1, CR-011-vcMMAE, PSMA-ADC, MEDI-547, SGN-19Am SGN-35, SGN-75 and the like
Activators of death receptor pathway include TRAIL, antibodies or other agents that target TRAIL or death receptors (e.g., DR4 and DR5) such as Apomab, conatumumab, ETR2-ST01, GDC0145 (lexatumumab), HGS-1029, LBY-135, PRO-1762 and trastuzumab.
Kinesin inhibitors include Eg5 inhibitors such as AZD4877, ARRY-520; CENPE inhibitors such as GSK923295A and the like.
JAK-2 inhibitors include CEP-701 (lesaurtinib), XL019 and INCB018424 and the like.
MEK inhibitors include ARRY-142886, ARRY-438162 PD-325901, PD-98059 and the like.
mTOR inhibitors include AP-23573, CCI-779, everolimus, RAD-001, rapamycin, temsirolimus, ATP-competitive TORC1/TORC2 inhibitors, including PI-103, PP242, PP30, Torin 1 and the like.
Non-steroidal anti-inflammatory drugs include AMIGESIC® (salsalate), DOLOBID® (diflunisal), MOTRIN® (ibuprofen), ORUDIS® (ketoprofen), RELAFEN® (nabumetone), FELDENE® (piroxicam), ibuprofen cream, ALEVE® (naproxen) and NAPROSYN® (naproxen), VOLTAREN® (diclofenac), INDOCIN® (indomethacin), CLINORIL® (sulindac), TOLECTIN® (tolmetin), LODINE® (etodolac), TORADOL® (ketorolac), DAYPRO® (oxaprozin) and the like.
PDGFR inhibitors include C-451, CP-673, CP-868596 and the like.
Platinum chemotherapeutics include cisplatin, ELOXATIN® (oxaliplatin) eptaplatin, lobaplatin, nedaplatin, PARAPLATIN® (carboplatin), satraplatin, picoplatin and the like.
Polo-like kinase inhibitors include BI-2536 and the like.
Phosphoinositide-3 kinase (PI3K) inhibitors include wortmannin, LY294002, XL-147, CAL-120, ONC-21, AEZS-127, ETP-45658, PX-866, GDC-0941, BGT226, BEZ235, XL765 and the like.
Thrombospondin analogs include ABT-510, ABT-567, ABT-898, TSP-1 and the like.
VEGFR inhibitors include AVASTIN® (bevacizumab), ABT-869, AEE-788, ANGIOZYME™ (a ribozyme that inhibits angiogenesis (Ribozyme Pharmaceuticals (Boulder, Colo.) and Chiron, (Emeryville, Calif.)), axitinib (AG-13736), AZD-2171, CP-547,632, IM-862, MACUGEN (pegaptamib), NEXAVAR® (sorafenib, BAY43-9006), pazopanib (GW-786034), vatalanib (PTK-787, ZK-222584), SUTENT® (sunitinib, SU-11248), VEGF trap, ZACTIMA™ (vandetanib, ZD-6474) and the like.
Antibiotics include intercalating antibiotics aclarubicin, actinomycin D, amrubicin, annamycin, adriamycin, BLENOXANE® (bleomycin), daunorubicin, CAELYX® or MYOCET® (liposomal doxorubicin), elsamitrucin, epirbucin, glarbuicin, ZAVEDOS® (idarubicin), mitomycin C, nemorubicin, neocarzinostatin, peplomycin, pirarubicin, rebeccamycin, stimalamer, streptozocin, VALSTAR® (valrubicin), zinostatin and the like.
Topoisomerase inhibitors include aclarubicin, 9-aminocamptothecin, amonafide, amsacrine, becatecarin, belotecan, BN-80915, CAMPTOSAR® (irinotecan hydrochloride), camptothecin, CARDIOXANE® (dexrazoxine), diflomotecan, edotecarin, ELLENCE® or PHARMORUBICIN® (epirubicin), etoposide, exatecan, 10-hydroxycamptothecin, gimatecan, lurtotecan, mitoxantrone, orathecin, pirarbucin, pixantrone, rubitecan, sobuzoxane, SN-38, tafluposide, topotecan and the like.
Antibodies include AVASTIN® (bevacizumab), CD40-specific antibodies, chTNT-1/B, denosumab, ERBITUX® (cetuximab), HUMAX-CD4® (zanolimumab), IGF1R-specific antibodies, lintuzumab, PANOREX® (edrecolomab), RENCAREX® (WX G250), RITUXAN® (rituximab), ticilimumab, trastuzimab, CD20 antibodies types I and II and the like.
Hormonal therapies include ARIMIDEX® (anastrozole), AROMASIN® (exemestane), arzoxifene, CASODEX® (bicalutamide), CETROTIDE® (cetrorelix), degarelix, deslorelin, DESOPAN® (trilostane), dexamethasone, DROGENIL® (flutamide), EVISTA® (raloxifene), AFEMA™ (fadrozole), FARESTON® (toremifene), FASLODEX® (fulvestrant), FEMARA® (letrozole), formestane, glucocorticoids, HECTOROL® (doxercalciferol), RENAGEL® (sevelamer carbonate), lasofoxifene, leuprolide acetate, MEGACE® (megesterol), MIFEPREX® (mifepristone), NILANDRON™ (nilutamide), NOLVADEX® (tamoxifen citrate), PLENAXIS™ (abarelix), prednisone, PROPECIA® (finasteride), rilostane, SUPREFACT® (buserelin), TRELSTAR® (luteinizing hormone releasing hormone (LHRH)), VANTAS® (Histrelin implant), VETORYL® (trilostane or modrastane), ZOLADEX® (fosrelin, goserelin) and the like.
Deltoids and retinoids include seocalcitol (EB1089, CB1093), lexacalcitrol (KH1060), fenretinide, PANRETIN® (aliretinoin), ATRAGEN® (liposomal tretinoin), TARGRETIN® (bexarotene), LGD-1550 and the like.
PARP inhibitors include ABT-888 (veliparib), olaparib, KU-59436, AZD-2281, AG-014699, BSI-201, BGP-15, INO-1001, ONO-2231 and the like.
Plant alkaloids include, but are not limited to, vincristine, vinblastine, vindesine, vinorelbine and the like.
Proteasome inhibitors include VELCADE® (bortezomib), MG132, NPI-0052, PR-171 and the like.
Examples of immunologicals include interferons and other immune-enhancing agents. Interferons include interferon alpha, interferon alpha-2a, interferon alpha-2b, interferon beta, interferon gamma-1a, ACTIMMUNE® (interferon gamma-1b) or interferon gamma-n1, combinations thereof and the like. Other agents include ALFAFERONE®, (IFN-α), BAM-002 (oxidized glutathione), BEROMUN® (tasonermin), BEXXAR® (tositumomab), CAMPATH® (alemtuzumab), CTLA4 (cytotoxic lymphocyte antigen 4), decarbazine, denileukin, epratuzumab, GRANOCYTE® (lenograstim), lentinan, leukocyte alpha interferon, imiquimod, MDX-010 (anti-CTLA-4), melanoma vaccine, mitumomab, molgramostim, MYLOTARG™ (gemtuzumab ozogamicin), NEUPOGEN® (filgrastim), OncoVAC-CL, OVAREX® (oregovomab), pemtumomab (Y-muHMFG1), PROVENGE® (sipuleucel-T), sargaramostim, sizofilan, teceleukin, THERACYS® (Bacillus Calmette-Guerin), ubenimex, VIRULIZIN® (immunotherapeutic, Lorus Pharmaceuticals), Z-100 (Specific Substance of Maruyama (SSM)), WF-10 (Tetrachlorodecaoxide (TCDO)), PROLEUKIN® (aldesleukin), ZADAXIN® (thymalfasin), ZENAPAX® (daclizumab), ZEVALIN® (90Y-Ibritumomab tiuxetan) and the like.
Biological response modifiers are agents that modify defense mechanisms of living organisms or biological responses, such as survival, growth or differentiation of tissue cells to direct them to have anti-tumor activity and include krestin, lentinan, sizofiran, picibanil PF-3512676 (CpG-8954), ubenimex and the like.
Pyrimidine analogs include cytarabine (ara C or Arabinoside C), cytosine arabinoside, doxifluridine, FLUDARA® (fludarabine), 5-FU (5-fluorouracil), floxuridine, GEMZAR® (gemcitabine), TOMUDEX® (ratitrexed), TROXATYL™ (triacetyluridine troxacitabine) and the like.
Purine analogs include LANVIS® (thioguanine) and PURI-NETHOL® (mercaptopurine).
Antimitotic agents include batabulin, epothilone D (KOS-862), N-(2-((4-hydroxyphenyl)amino)pyridin-3-yl)-4-methoxybenzenesulfonamide, ixabepilone (BMS 247550), paclitaxel, TAXOTERE® (docetaxel), PNU100940 (109881), patupilone, XRP-9881 (larotaxel), vinflunine, ZK-EPO (synthetic epothilone) and the like.
Ubiquitin ligase inhibitors include MDM2 inhibitors, such as nutlins, NEDD8 inhibitors such as MLN4924 and the like.
Compounds of this invention can also be used as radiosensitizers that enhance the efficacy of radiotherapy. Examples of radiotherapy include external beam radiotherapy, teletherapy, brachytherapy and sealed, unsealed source radiotherapy and the like.
Additionally, compounds having Formula (I) may be combined with other chemotherapeutic agents such as ABRAXANE™ (ABI-007), ABT-100 (farnesyl transferase inhibitor), ADVEXIN® (Ad5CMV-p53 vaccine), ALTOCOR® or MEVACOR® (lovastatin), AMPLIGEN® (poly I:poly C12U, a synthetic RNA), APTOSYN® (exisulind), AREDIA® (pamidronic acid), arglabin, L-asparaginase, atamestane (1-methyl-3,17-dione-androsta-1,4-diene), AVAGE® (tazarotene), AVE-8062 (combreastatin derivative) BEC2 (mitumomab), cachectin or cachexin (tumor necrosis factor), canvaxin (vaccine), CEAVAC® (cancer vaccine), CELEUK® (celmoleukin), CEPLENE® (histamine dihydrochloride), CERVARIX® (human papillomavirus vaccine), CHOP® (C: CYTOXAN® (cyclophosphamide); H: ADRIAMYCIN® (hydroxydoxorubicin); O: Vincristine (ONCOVIN®); P: prednisone), CYPAT™ (cyproterone acetate), combrestatin A4P, DAB(389)EGF (catalytic and translocation domains of diphtheria toxin fused via a His-Ala linker to human epidermal growth factor) or TransMID-107R™ (diphtheria toxins), dacarbazine, dactinomycin, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), eniluracil, EVIZON™ (squalamine lactate), DIMERICINE® (T4N5 liposome lotion), discodermolide, DX-8951f (exatecan mesylate), enzastaurin, EP0906 (epithilone B), GARDASIL® (quadrivalent human papillomavirus (Types 6, 11, 16, 18) recombinant vaccine), GASTRIMMUNE®, GENASENSE®, GMK (ganglioside conjugate vaccine), GVAX® (prostate cancer vaccine), halofuginone, histerelin, hydroxycarbamide, ibandronic acid, IGN-101, IL-13-PE38, IL-13-PE38QQR (cintredekin besudotox), IL-13-pseudomonas exotoxin, interferon-α, interferon-γ, JUNOVAN™ or MEPACT™ (mifamurtide), lonafarnib, 5,10-methylenetetrahydrofolate, miltefosine (hexadecylphosphocholine), NEOVASTATAAE-941), NEUTREXIN® (trimetrexate glucuronate), NIPENT® (pentostatin), ONCONASE® (a ribonuclease enzyme), ONCOPHAGE® (melanoma vaccine treatment), ONCOVAX® (IL-2 Vaccine), ORATHECIN™ (rubitecan), OSIDEM® (antibody-based cell drug), OVAREX® MAb (murine monoclonal antibody), paclitaxel, PANDIMEX™ (aglycone saponins from ginseng comprising 20(S)protopanaxadiol (aPPD) and 20(S)protopanaxatriol (aPPT)), panitumumab, PANVAC®-VF (investigational cancer vaccine), pegaspargase, PEG Interferon A, phenoxodiol, procarbazine, rebimastat, REMOVAB® (catumaxomab), REVLIMID® (lenalidomide), RSR13 (efaproxiral), SOMATULINE® LA (lanreotide), SORIATANE® (acitretin), staurosporine (Streptomyces staurospores), talabostat (PT100), TARGRETIN® (bexarotene), TAXOPREXIN® (DHA-paclitaxel), TELCYTA® (canfosfamide, TLK286), temilifene, TEMODAR® (temozolomide), tesmilifene, thalidomide, THERATOPE® (STn-KLH), thymitaq (2-amino-3,4-dihydro-6-methyl-4-oxo-5-(4-pyridylthio)quinazoline dihydrochloride), TNFERADE™ (adenovector: DNA carrier containing the gene for tumor necrosis factor-α), TRACLEER® or ZAVESCA® (bosentan), tretinoin (Retin-A), tetrandrine, TRISENOX® (arsenic trioxide), VIRULIZIN®, ukrain (derivative of alkaloids from the greater celandine plant), vitaxin (anti-alphavbeta3 antibody), XCYTRIN® (motexafin gadolinium), XINLAY™ (atrasentan), XYOTAX™ (paclitaxel poliglumex), YONDELIS® (trabectedin), ZD-6126, ZINECARD® (dexrazoxane), ZOMETA® (zolendronic acid), zorubicin and the like.
Data
Determination of the utility of compounds having Formula (I) as binders to and inhibitors of NAMPT was performed using Time-Resolved Fluorescence Resonance Energy Transfer (TR-FRET) binding assays.
Time-Resolved Fluorescence Resonance Energy Transfer (TR-FRET) Binding Assay of NAMPT
Test compounds were serially diluted (typically 11 half log dilutions) in neat DMSO to 50× final concentrations prior to dilution with assay buffer (50 mM HEPES (NaOH), pH 7.5, 100 mM NaCl, 10 mM MgCl 2 , 1 mM DTT, 1% Glycerol) to 3× and 6% DMSO. Six L were transferred to 384-well low-volume plates (Owens Corning #3673). To this, 12 L of a 1.5× solution containing enzyme, probe and antibody were added. Final concentrations in the 18 L reactions were 1× assay buffer, 2% DMSO, 6.8 nM NAMPT (human, recombinant, C-terminally His-tagged), 200 nM probe (a potent nicotinamide-competitive inhibitor conjugated to Oregon Green 488) and 1 nM Tb-anti-His antibody (Invitrogen # PV5895). Reactions were equilibrated at room temperature for 3 hours prior to reading on an Envision multi-label plate reader (Perkin Elmer; Ex=337 nm, Em=520 and 495 nm). Time-resolved FRET ratios (Em 520 /Em 495 ) were normalized to controls, plotted as a function of compound concentration and fit with the four-parameter logistic equation to determine IC50s.
Time-Resolved Fluorescence Resonance Energy Transfer (TR-FRET) Binding Assay of NAMPT with PRPP
Compound handling and data processing were identical to the assay in the absence of substrates (above). Final concentrations were 1× assay buffer, 2% DMSO, 2 nM NAMPT, 2 nM probe, 1 nM Tb-anti-His antibody (Invitrogen # PV5895), 200 M PRPP and 2.5 mM ATP. Reactions were equilibrated for 16 hours prior to measurement to allow for potential enzymatic modification of test compounds.
Table 1 shows the utility of compounds having Formula I to functionally inhibit NAMPT.







TABLE 1





TR-FRET


TR-FRET
Binding-IC50


Binding-IC50
(with PRPP)

Example
(μM)
(μM)









1
0.0921
0.00072

2
0.854
0.0398

3
0.0316
0.000282

4
0.413
0.000516

5
2.5
0.000684

6
2.91
0.000964

7
0.183
0.000516

8
0.114
0.000702

9
1.72
0.000459

10
0.197
0.000457

11
7.6
0.000271

12
0.486
0.000292

13
0.653
0.000663

14
0.741
0.00122

15
1.76
0.000841

16
0.409
0.000396

17
2.96
0.000401

18
2.73
0.000418

19
2.68
0.000921

20
0.404
0.000169

21
0.433
0.000887

22
0.399
0.000277

23
0.281
0.000409

24
0.167
0.000363

25
0.508
0.000714

26
0.211
0.0011

27
0.756
0.000658

28
0.152
0.00019

29
0.168
0.000236

30
1.18
0.000785

31
0.739
0.000311

32
0.906
0.000169

33
0.369
0.000553

34
0.208
0.000377

35
0.387
0.000801

36
0.356
0.000444

37
0.129
0.000309

38
0.243
0.000266

39
0.814
0.00026

40
0.0409
0.000217

41
0.294
0.00115

42
0.697
0.000381

43
4.35
0.000169

44
0.396
0.000496

45
0.879
0.00119

46
0.773
0.000318

47
0.0575
0.00062

48
>10
0.000169

49
0.442
0.000317

50
1.64
0.000817

51
0.264
0.000524

52
0.0186
0.00579

53
4.45
0.0144

54
0.363
0.00255

55
0.364
0.00137

56
0.158
0.00107

57
0.0058


58
0.523
0.00143

59
0.222
0.000695

60
0.00861
0.00149

61
0.0782
0.000549

62
0.25
0.000456

63
0.636
0.000283

64
0.518
0.000495

65
0.773
0.000685

66
0.558
0.000326

67
0.53
0.000326

68
0.386
0.000476

69
0.676
0.000268

70
0.71
0.000616

71
0.754
0.000348

72
0.851
0.000536

73
0.605
0.000426

74
0.356
0.000222

75
0.0122
0.000445

76
0.993
0.000739

77
0.0561
0.00288

78
0.0565
0.0024

79
0.121
0.00697

80
0.228
0.00571

81
0.0155
0.00268

82
0.357
0.00642

83
0.899
0.0023

84
1.67
0.0109

85
4.07
0.00141

86
2.04
0.0119

87
2.05
0.00135

88
2.85
0.00855

89
0.667
0.000383

90
0.204
0.00063

91
0.174
0.00126

92
0.183
0.000881

93
0.389
0.00139

94
0.29
0.000593

95
0.201
0.000991

96
0.192
0.00156

97
0.109
0.000333

98
0.12
0.000367

99
0.119
0.000411

100
0.102
0.000169

101
0.332
0.00173

102
0.385
0.00121

103
0.84
0.00144

104
0.135
0.002

105
0.106
0.000476

106
0.247
0.000201

107
0.0451
0.000492

108
1.77
0.00105

109
0.34
0.000209

110
0.423
0.000174

111
0.263
0.000209

112
0.0465
0.000169

113
0.356
0.000169

114
0.818
0.00111

115
0.243
0.000676

116
0.863
0.00069

117
0.392
0.000436

118
0.0352
0.000234

119
0.942
0.000783

120
0.0739
0.000367

121
0.486
0.000234

122
0.255
0.00476

123
0.133
0.00257

124
1.1
0.00212

125
0.547
0.00209

126
0.102
0.000963

127
0.0522
0.000522

128
0.0307
0.000873

129
0.0116
0.000634

130
0.0532
0.000981

131
0.0152
0.00167

132
0.155
0.0133

133
0.067
0.000709

134
0.303
0.00149

135
0.0738
0.00127

136
0.0727
0.000512

137
0.315
0.00721

138
0.0807
0.000424

139
0.582
0.000173

140
1.34
0.000927

141
2.11
0.000757

142
1.43
0.00305

143
8.71
0.00203

144
9.49
0.00292

145
0.191
0.00108

146
0.261
0.000403

147
0.251
0.00063

148
6.23
0.00135

149
>10
0.00486

150
6.11
0.00349

151
7.15
0.00554

152
3.6
0.00691

153
0.118
0.00188

154
0.194
0.0026

155
3.37
0.0023

156
3.27
0.00318

157
4.14
0.0011

158
0.341
0.00639

159
2.49
0.00216

160
3.22
0.00126

161
1.31
0.00289

162
2.57
0.00209

163
2.1
0.00629

164
2.46
0.00346

165
1.53
0.00161

166
1.43
0.00181

167
1.73
0.00252

168
1.11
0.000951

169
0.375
0.00425

170
3.36
0.00225

171
2.17
0.00251

172
2.21
0.00355

173
1.51
0.00124

174
0.0283
0.000169

175
0.697
0.0009

176
0.0606
0.000414

177
0.0201
0.000169

178
0.0143
0.000169

179
0.0581
0.000445

180
0.584
0.000266

181
0.349
0.000283

182
0.139
0.0004

183
1.05
0.0018

184
4.34
0.00254

185
>10
0.00186

186
0.0657
0.000347

187
0.549
0.000172

188
>10
0.00509

189
0.192
0.0111

190
0.4
0.00457

191
0.821
0.00609

192
0.238
0.000242

193
0.516
0.000266

194
0.0323
0.00024

195
0.0247
0.000251

196
0.358
0.000169

197
1.57
0.000505

198
0.0325
0.000225

199
0.00976
0.000311

200
0.063
0.000482

201
0.0466
0.000281

202
0.216
0.000355

203
0.0137
0.00021

204
4.83
0.000773

205
1.06
0.000358

206
0.0257
0.000263

207
1.51
0.000282

208
0.404
0.000169

209
0.811
0.000988

210
0.469
0.000363

211
1.66
0.000453

212
0.0448
0.00021

213
0.116
0.000271

214
0.641
0.00128

215
2.01
0.00304

216
0.118
0.00019

217
0.22
0.0002

218
0.123
0.000169

219
0.0794
0.000903

220
0.0742
0.000278

221
0.12
0.000352

222
0.112
0.000192

223
0.109
0.000354

224
0.233
0.000555

225
0.155
0.000673

226
0.113
0.000608

227
0.0162
0.000273

228
0.0494
0.000238

229
0.0136
0.000398

230
0.294
0.000169

231
0.817
0.000546

232
0.396
0.000277

233
0.495
0.000401

234
0.904
0.000736

235
0.494
0.000369

236
0.604
0.000243

237
0.451
0.000285

238
0.123
0.000187

239
0.308
0.000771

240
7.35
0.00875

241
0.0674
0.000169

242
0.0571
0.000169

243
0.169
0.000169

244
>10
0.00169

245
2.89
0.000502

246
0.0732
0.00022

247
0.0627
0.000275

248
0.0658
0.000169

249
0.817
0.00072

250
0.0205
0.00023

251
2.2
0.00063

252
0.0374
0.000274

253
0.0144
0.000229

254
0.0313
0.000306

255
8.19
0.00222

256
0.126
0.000266

257
0.101
0.000344

258
0.113
0.000558

259
0.0266
0.000169

260
0.0465
0.000351

261
0.0627
0.000231

262
0.00367
0.000221

263
0.0486
0.000247

264
0.0404
0.000412

265
0.0331
0.000266

266
0.12
0.000333

267
0.0543
0.000291

268
0.755
0.000169

269
0.0412
0.000169

270
0.0609
0.000991

271
0.0517
0.000169

272
0.0272
0.000417

273
0.0493
0.000555

274
0.0178
0.000196

275
0.0123
0.00043

276
0.107
0.000468

277
0.103
0.000667

278
0.102
0.000621

279
0.0688
0.000437

280
0.0113
0.000213

281
0.0055
0.000214

282
0.0765
0.000297

283
0.0632
0.000264

284
0.00796
0.000169

285
0.0826
0.000593

286
0.12
0.000412

287
0.0673
0.000351

288
0.0495
0.000568

289
0.155
0.000286

290
0.415
0.00096

291
0.159
0.000449

292
1.54
0.00115

293
0.0273
0.000169

294
0.0447
0.000169

295
0.0561
0.000292

296
0.067
0.000226

297
0.177
0.000286

298
3.41
0.000557

299
0.172
0.000283

300
0.0614
0.000169

301
0.288
0.000301

302
0.16
0.000435

303
0.00999
0.000169

304
0.0662
0.000169

305
0.494
0.000449

306
0.144
0.000169

307
0.0508
0.000169

308
0.306
0.000169

309
0.117
0.000169

310
0.564
0.000217

311
0.289
0.000274

312
0.165
0.000243

313
0.531
0.00036

314
1.98
0.000581

315
0.231
0.00032

316
0.0421
0.000169

317
0.317
0.000282

318
0.0416
0.000228

319
0.466
0.000192

320
0.0963
0.000208

321
3.16
0.000792

322
6.04
0.0341

323
1.4
0.000232

324
0.981
0.000752

325
0.18
0.000278

326
2.35
0.0013

327
1.32
0.000558

328
0.068
0.000169

329
0.0308
0.000169

330
0.32
0.000432

331
0.383
0.000416

332
0.18
0.000297

333
0.583
0.000346

334
0.0809
0.000345

335
0.632
0.000354

336
0.334
0.000264

337
0.497
0.000205

338
0.609
0.000394

339
>10
0.000797

340
>10
0.000817

341
>10
0.000719

342
>10
0.000454

343
>10
0.000456

344
0.036
0.000169

345
0.201
0.00027

346
3.11
0.000548

347
4.73
0.000667

348
>10
0.00152

349
4.11
0.000736

350
>10
0.000795

351
8.39
0.000792

352
>10
0.00106

353
3.17
0.00047

354
>10
0.000526

355
0.831
0.000169

356
>10
0.000169

357
>10
0.000291

358
1.84
0.00219

359
>10
0.0025

360
0.291
0.000717

361
5.03
0.00194

362
0.143
0.000256

363
0.588
0.000305

364
0.135
0.000172

365
1.34
0.000171

366
0.146
0.000435

367
0.65
0.00018

368
0.602
0.000317

369
0.429
0.000337

370
0.0476
0.000175

371
1.44
0.000298

372
2.44
0.00046

373
3.04
0.00036

374
1.67
0.000292

375
0.986
0.000241

376
1.05
0.000305

377
1.67
0.000275

378
0.897
0.000169

379
0.279
0.00029

380
0.179
0.000251

381
0.0841
0.000259

382
0.119
0.000204

383
0.0495
0.000225

384
0.406
0.000375

385
0.491
0.000539

386
0.283
0.000254

387
0.419
0.000467

388
0.388
0.000506

389
0.584
0.000617

390
0.133
0.000445

391
0.171
0.000227

392
0.814
0.000465

393
>10
0.00437

394
>10
0.00308

395
0.0125
0.000193

396
0.0226
0.00036

397
0.0177
0.000169

398
0.21
0.000792

399
9.5
0.00154

400
0.0812
0.000298

401
0.0126
0.000292

402
0.0548
0.000327

403
1.55
0.000847

404
2.55
0.00088

405
0.0784
0.000214

406
1.14
0.000505

407
0.22
0.000659

408
0.276
0.000725

409
>10
0.48

410
0.0207
0.000169

411
1.87
0.000556

412
1.25
0.000424

413
0.805
0.000279

414
2.63
0.000307

415
1.62
0.000246

416
2.5
0.000318

417
6.84
0.000264

418
4.75
0.000233

419
2.43
0.000197

420
2.71
0.000226

421
2.45
0.000271

422
1.72
0.000212

423
8.26
0.000338

424
0.988
0.000494

425
0.153
0.000227

426
0.0256
0.000169

427
0.15
0.00027

428
0.0871
0.000258

429
0.129
0.000396

430
0.292
0.000264

431
0.301
0.000276

432
0.304
0.00033

433
0.2
0.000248

434
0.102
0.000169

435
0.163
0.000191

436
1.59
0.000416

437
0.0291
0.000169

438
0.145
0.000427

439
0.453
0.000641

440
0.295
0.00049

441
0.338
0.000324

442
0.301
0.0002

443
0.138
0.000274

444
0.156
0.000244

445
0.11
0.000212

446
0.388
0.000253

447
0.261
0.000232

448
0.175
0.000176

449
0.256
0.000169

450
0.422
0.000244

451
0.4
0.000373

452
0.293
0.000285

453
0.152
0.000258

454
0.405
0.00034

455
0.0167
0.000194

456
0.389
0.000169

457
1.14
0.000487

458
0.94
0.000382

459
0.381
0.00041

460
0.569
0.000307

461
0.459
0.000169

462
0.0591
0.000266

463
0.314
0.000529

464
0.0634
0.000169

465
0.0138
0.000169

466
0.0749
0.000287

467
0.0911
0.000278

468
>10
0.000985

469
10
0.000432

470
5.58
0.000456

471
3.44
0.000471

472
2.86
0.000334

473
10
0.00101

474
1.98
0.000362

475
0.00976
0.000169

476
0.0708
0.000194

477
0.0729
0.000235

478
0.192
0.00024

479
0.063
0.000243

480
0.181
0.000342

481
0.0572
0.000176

482
0.0763
0.000259

483
0.13
0.000575

484
0.0795
0.00019

485
0.0956
0.000205

486
0.0917
0.000232

487
0.143
0.000334

488
0.138
0.000544

489
1.22
0.000263

490
0.753
0.000267

491
10
0.0019

492
10
0.000863

493
1.29
0.000455

494
7.56
0.000712

495
1.47
0.000399

496
0.199
0.00114

497
0.0242
0.00286

498
0.309
0.000169

499
0.113
0.00038

500
0.181
0.000169

501
0.104
0.000483

502
0.169
0.000385

503
0.0532
0.000277

504
0.185
0.000361

505
0.253
0.000355

506
0.245
0.000407

507
0.121
0.000359

508
0.257
0.000481

509
0.163
0.000384

510
0.142
0.000284

511
0.0653
0.000286

512
0.631
0.000209

513
0.0239
0.000188

514
0.368
0.000249

515
0.18
0.000268

516
0.117
0.000266

517
0.33
0.000264

518
0.234
0.000169

519
0.218
0.000338

520
0.565
0.000301

521
0.413
0.000292

522
0.0581
0.000199

523
0.343
0.000422

524
0.0247
0.000169

525
0.0864
0.000213

526
0.126
0.000275

527
0.141
0.000265

528
0.126
0.000276

529
0.248
0.000283

530
0.378
0.000791

531
0.333
0.000253

532
0.338
0.000178

533
0.101
0.000169

534
0.145
0.000251

535
0.297
0.000325

536
0.0776
0.000202

537
0.461
0.00023

538
0.275
0.000514

539
0.0985
0.00031

540
0.266
0.000305

541
0.175
0.000448

542
0.0351
0.000337

543
1.48
0.000383

544
0.871
0.000437

545
0.109
0.000403

546
0.237
0.0232

547
0.498
0.000423

548
0.397
0.000471

549
0.0812
0.000224

550
0.762
0.000427

551
0.713
0.000392

552
0.184
0.000543

553
0.478
0.000592

554
0.451
0.000837

555
0.427
0.000749

556
0.00543
0.000407

557
0.167
0.000359

558
1.41
0.000352

559
0.681
0.000223

560
0.969
0.000312

561
0.869
0.000335

562
0.218
0.000607

563
0.322
0.00419

564
0.0238
0.00343

565
0.215
0.00538

566
>10
0.216

567
0.403
0.00111

568
0.375
0.000723

569
0.217
0.000669

570
0.0704
0.000751

571
0.0417
0.000494

572
0.0516
0.000403

573
0.0242
0.000403

574
0.0975
0.000505

575
3.25
0.0108

576
0.016
0.000783

577
0.0189
0.000361

578
0.682
0.000775

579
0.488
0.000634

580
1.47
0.000798

581
0.945
0.00109

582
0.711
0.000911

583
1.12
0.000799

584
0.811
0.000756

585
0.641
0.000648

586
0.842
0.00109

587
0.236
0.000917

588
0.684
0.000623

589
0.0161
0.000887

590
0.666
0.000734

591
0.138
0.000761

592
0.0388
0.000603

593
0.767
0.000544

594
0.0227
0.000682

595
0.133
0.000746

596
0.691
0.000909

597
0.232
0.000862

598
0.457
0.000804

599
0.527
0.000786

600
0.51
0.000169

601
0.712
0.000682

602
0.786
0.000887

603
1.03
0.00101

604
0.151
0.000843

605
0.559
0.000886

606
0.281
0.000169

607
0.478
0.000796

608
0.481
0.00051

609
0.598
0.00062

610
0.751
0.000762

611
0.288
0.000621

612
0.706
0.000919

613
0.347
0.000916

614
0.216
0.00067

615
0.544
0.00079

616
0.174
0.00049

617
0.164
0.000645

618
0.5
0.000751

619
0.0793
0.000616

620
0.71
0.001

621
0.114
0.00542

622
0.0294
0.00236

623
1.01
0.0016

624
0.261
0.000627

625
0.795
0.00076

626
0.645
0.000793

627
0.211
0.00071

628
0.706
0.000978

629
0.23
0.000643

630
0.266
0.000563

631
0.616
0.00126

632
0.27
0.000698

633
0.335
0.000707

634
0.353
0.000648

635
0.462
0.000975

636
0.238
0.000915

637
0.36
0.000421

638
0.0166
0.000545

639
0.215
0.000713

640
0.17
0.000817

641
0.0748
0.000684

642
0.454
0.000532

643
0.028
0.000552

644
0.0817
0.00069

645
0.091
0.000474

646
0.195
0.00051

647
0.173
0.000672

648
0.661
0.00106

649
0.203
0.000749

650
0.153
0.00111

651
0.276
0.000715

652
0.535
0.00116

653
0.831
0.000893

654
0.213
0.000945

655
0.23
0.000998

656
0.218
0.000738

657
0.232
0.000589

658
0.137
0.00076

659
0.646
0.00071

660
0.282
0.000693

661
0.462
0.000641

662
0.318
0.000671

663
0.653
0.00107

664
0.214
0.000733

665
0.123
0.000357

666
0.193
0.000855

667
0.226
0.000798

668
0.263
0.0011

669
0.407
0.000807

670
0.062
0.000545

671
0.611
0.00106

672
0.313
0.000504

673
0.452
0.000697

674
0.297
0.000535

675
0.376
0.00207

676
0.126
0.00698

677
0.00177
0.000796

678
0.0412
0.00023

679
0.0228
0.00174

680
0.0371
0.00238

681
0.0276
0.002

682
0.607
0.00158

683
0.154
0.00119

684
0.481
0.00134

685
1.25
0.00136

686
0.959
0.0013

687
0.0973
0.00116

688
1.11
0.00266

689
0.016
0.00132

690
0.0643
0.00122

691
0.169
0.00067

692
0.0839
0.00119

693
0.781
0.00142

694
0.163
0.00112

695
0.0137
0.000621

696
0.272
0.000725

697
0.735
0.000802

698
0.0364
0.000629

699
0.0411
0.000721

700
0.0684
0.00103

701
0.367
0.000856

702
0.568
0.00129

703
0.559
0.000824

704
0.503
0.000777

705
0.876
0.00163

706
0.0841
0.000937

707
0.277
0.000624

708
0.06
0.0009

709
0.0194
0.000473

710
0.0491
0.00125

711
0.0885
0.00111

712
0.0911
0.000907

713
0.0443
0.000689

714
0.168
0.000991

715
0.0659
0.000771

716
0.0502
0.000607

717
0.186
0.000428

718
0.0236
0.000755

719
0.00632
0.000835

720
0.0367
0.000181

721
0.125
0.00121

722
0.0394
0.00101

723
0.154
0.000932

724
0.161
0.000992

725
0.0196
0.000747

726
0.251
0.000534

727
0.166
0.000783

728
0.14
0.000496

729
0.428
0.000765

730
0.489
0.000847

731
0.223
0.000391

732
0.0213
0.000471

733
0.119
0.000712

734
0.0142
0.000605

735
0.646
0.000864

736
3.09
0.00073

737
0.0704
0.000612

738
0.364
0.000705

739
0.0377
0.000672

740
0.0701
0.000403

741
0.068
0.000647

742
0.241
0.000526

743
0.0633
0.000691

744
1.08
0.000806

745
0.994
0.000783

746
0.795
0.000839

747
0.435
0.00175

748
0.558
0.000648

749
0.392
0.00079

750
1.53
0.00154

751
1.24
0.001

752
5.19
0.00077

753
0.403
0.000783

754
0.00492
0.00051

755
0.013
0.00057

756
0.123
0.000609

757
0.0156
0.000705

758
0.132
0.00061

759
0.0285
0.000799

760
0.0289
0.00071

761
0.0944
0.000394

762
0.0301
0.000506

763
0.0485
0.000478

764
0.135
0.000465

765
0.0365
0.000782

766
0.0615
0.000581

767
0.265
0.00064

768
0.0281
0.000672

769
0.0984
0.000705

770
0.0388
0.000735

771
0.0708
0.000573

772
0.0615
0.000828

773
0.0726
0.000773

774
0.103
0.00046

775
0.0519
0.000538

776
0.0215
0.000169

777
0.0394
0.00092

778
0.0276
0.000414

779
0.0142
0.000603

780
0.25
0.000382

781
0.0875
0.000839

782
0.134
0.000466

783
0.0644
0.000907

784
0.0226
0.000455

785
0.0236
0.000638

786
0.0444
0.000484

787
0.055
0.000474

788
0.082
0.000674

789
0.0217
0.000434

790
0.0795
0.000586

791
0.0471
0.00115

792
0.116
0.0005

793
0.0231
0.000398

794
0.029
0.000465

795
0.0896
0.000764

796
0.0917
0.00049

797
0.0972
0.000671

798
0.0957
0.00047

799
0.102
0.000406

800
0.0821
0.000925

801
0.866
0.001

802
0.0359
0.000533

803
0.314
0.00101

804
0.289
0.000445

805
3.92
0.00112

806
2.74
0.000543

807
0.628
0.000509

808
0.0944
0.000568

809
0.0953
0.00063

810
0.481
0.0126

811
0.0998
0.00286

812
0.08
0.00257

813
0.0112
0.00153

814
0.0687
0.00163

815
0.053
0.00193

816
0.0461
0.00158

817
0.0658
0.0016

818
1.52
0.000644

819
0.0199
0.000624

820
0.499
0.00928

821
0.663
0.000284

822
0.104
0.00346

823
0.189
0.000356

824
0.118
0.000566

825
0.0261
0.000538

826
0.00779
0.000897

















































































































































































































































































































































































































































































































































































































































































































































































































































































NAMPT Cell Proliferation Assay
PC3 cells were seeded in 96-well black plates (Corning #3904) at 500 cells/well in 90 l of RPMI media containing 10% heat-inactivated FBS and incubated overnight at 37° C. and 5% CO 2 to allow cells to attach to wells. The following day, test compounds were serially diluted in neat DMSO to 1000× final concentrations prior to dilution with RPMI media to 10× and 1% DMSO. Ten L of the 10× compounds were then transferred to wells containing cells to produce a dose response of 10-fold dilutions from 10 M to 1×10 −5 M. Cells were incubated for 5 days at 37° C. and 5% CO 2 , then cell viability was measured using Cell Titer Glo reagent (Promega #G7571). Percent inhibition values were calculated and fitted to a sigmoidal dose response curves using Assay Explorer software to determine IC50s. To assess whether inhibition of cell viability was due to NAMPT inhibition, the proliferation assay was also performed in the presence of 0.3 mM nicotinamide mononucleotide.
Table 2 shows the results of the cell proliferation assay.








TABLE 2






Cell Titer-



Glo -


Example
IC50 (M)











1
0.0609


2
>10


3
0.0367


4
0.935


5
0.74


6
6.65


7
0.527


8
0.0702


9
0.649


10
0.331


11
4.53


12
0.213


13
1.17


14
0.644


15
3.97


16
0.325


17
4.96


18
0.36


19
6.63


20
0.102


21
0.899


22
0.142


23
0.0415


24
0.691


25
0.146


26
0.261


27
7.54


28
0.0142


29
0.0439


30
0.0384


31
0.107


32
0.284


33
0.0673


34
0.0383


35
0.0586


36
0.0514


37
0.0347


38
0.0659


39
7.28


40
0.0708


41
0.138


42
1.59


43
7.45


44
1.58


45
2.07


46
6.28


47
0.0648


48
5.32


49
7.04


50
6.14


51
0.083


52
0.00407


53
3.3


54
0.303


55
0.0146


56
0.00886


57
0.00576


58
0.0526


59
0.143


60
0.00958


61
0.00601


62
0.0165


63
0.0168


64
0.0198


65
0.0656


66
0.0115


67
0.0119


68
0.0538


69
0.0166


70
0.0278


71
0.0667


72
0.0659


73
0.0595


74
0.014


75
0.00149


76
0.185


77
0.0142


78
0.0407


79
0.00745


80
0.0194


81
0.0071


82
0.0679


83
0.0243


84
0.762


85
2.61


86
5.72


87
6.58


88
8.11


89
0.113


90
0.0187


91
0.0139


92
0.00948


93
0.00713


94
0.0142


95
0.0106


96
0.00965


97
0.00455


98
0.0194


99
0.0264


100
0.0162


101
0.00244


102
0.013


103
0.0621


104
0.00846


105
0.00661


106
0.0787


107
0.0108


108
7.66


109
0.0522


110
0.202


111
0.0755


112
0.00696


113
0.0933


114
0.142


115
0.00638


116
0.0613


117
0.0639


118
0.0182


119
0.146


120
0.0908


121
0.00391


122
0.172


123
0.00743


124
0.0208


125
0.023


126
0.00396


127
0.00234


128
0.00221


129
0.00274


130
0.00655


131
0.00217


132
0.523


133
0.00216


134
0.00654


135
0.00636


136
0.00305


137
0.225


138
0.00383


139
0.0122


140
0.0655


141
0.0778


142
0.0182


143
0.0808


144
0.187


145
0.00601


146
0.00769


147
0.00669


148
0.0415


149
0.0266


150
0.0362


151
0.0761


152
0.0283


153
0.00373


154
0.00667


155
0.0176


156
0.028


157
0.0292


158
0.191


159
0.233


160
0.915


161
0.635


162
0.0436


163
0.0964


164
0.101


165
0.137


166
0.0971


167
0.104


168
0.208


169
0.0269


170
0.604


171
0.0447


172
0.223


173
0.0501


174
0.00112


175
0.313


176
0.00181


177
0.00169


178
0.00185


179
0.00218


180
0.00912


181
0.00775


182
0.00137


183
0.063


184
0.0651


185
5.05


186
0.00236


187
0.0341


188
6.29


189
0.0293


190
0.0149


191
0.0143


192
0.00185


193
0.0199


194
0.000773


195
0.000966


196
0.00675


197
0.0254


198
0.00184


199
0.000539


200
0.00572


201
0.00189


202
0.00488


203
0.00239


204
1.62


205
0.483


206
0.00131


207
0.739


208
0.0849


209
0.693


210
0.398


211
0.95


212
0.0341


213
0.0397


214
0.289


215
0.686


216
0.00659


217
0.00342


218
0.0711


219
0.00559


220
0.00573


221
0.00782


222
0.00408


223
0.00708


224
0.023


225
0.00927


226
0.00726


227
0.00628


228
0.00856


229
0.00106


230
0.0072


231
0.0351


232
0.00927


233
0.00937


234
0.105


235
0.0555


236
0.0138


237
0.0372


238
0.00257


239
0.0177


240
0.651


241
0.00848


242
0.00756


243
0.028


244
7.04


245
5.5


246
0.00243


247
0.00134


248
0.00242


249
0.0665


250
0.000675


251
1.84


252
0.00191


253
0.000702


254
0.000938


255
4.29


256
0.00984


257
0.0152


258
0.0325


259
0.00254


260
0.00806


261
0.0051


262
0.00187


263
0.00243


264
0.00669


265
0.00159


266
0.606


267
0.665


268
5.54


269
0.0151


270
0.973


271
0.00271


272
0.0156


273
0.00235


274
0.0104


275
0.0239


276
0.0381


277
0.0832


278
0.0517


279
0.869


280
0.013


281
0.0248


282
0.0447


283
0.145


284
0.107


285
0.301


286
0.0194


287
0.0241


288
0.00811


289
0.00933


290
0.0722


291
0.0261


292
7.22


293
0.00774


294
0.00188


295
0.0242


296
0.0115


297
0.0358


298
2.37


299
8.64


300
0.0287


301
0.0258


302
0.0193


303
0.00179


304
0.0188


305
1.17


306
0.0219


307
0.0136


308
0.0295


309
0.0548


310
0.0244


311
0.0191


312
0.065


313
0.82


314
0.395


315
0.72


316
0.00634


317
0.542


318
0.0421


319
0.0293


320
0.171


321
1.13


322
>10


323
0.175


324
0.0547


325
0.0329


326
0.457


327
0.638


328
0.0089


329
0.0124


330
0.0229


331
0.227


332
0.0643


333
0.116


334
0.0219


335
0.0976


336
0.139


337
0.533


338
0.081


339
9.18


340
>10


341
8.3


342
6.73


343
6.53


344
0.00746


345
0.281


346
7.02


347
8.08


348
>10


349
5.51


350
8.17


351
8.11


352
9.8


353
7.51


354
7.49


355
1.94


356
1.02


357
6.74


358
2.26


359
8.77


360
0.663


361
>10


362
0.106


363
7.66


364
0.031


365
0.332


366
0.0215


367
0.601


368
0.0484


369
0.738


370
0.00993


371
0.82


372
0.868


373
0.585


374
0.792


375
>10


376
>10


377
>10


378
>10


379
0.37


380
0.04


381
0.0173


382
0.0838


383
0.0133


384
0.0517


385
0.11


386
0.0424


387
0.0581


388
0.122


389
0.0783


390
0.0803


391
0.0784


392
0.666


393
>10


394
>10


395
0.00634


396
0.0324


397
0.00712


398
0.0736


399
7.68


400
0.712


401
0.0559


402
0.00671


403
0.0545


404
9.41


405
0.0221


406
0.347


407
1.31


408
0.0192


409
10


410
nd


411
4.72


412
0.978


413
0.19


414
0.853


415
0.234


416
0.659


417
0.867


418
0.866


419
0.365


420
0.147


421
0.317


422
0.109


423
0.187


424
0.521


425
0.069


426
0.0064


427
0.0622


428
0.0675


429
0.0186


430
0.0886


431
0.0719


432
0.0363


433
0.0644


434
0.00559


435
0.0204


436
0.762


437
0.00702


438
0.0425


439
0.0375


440


441
0.0072


442
0.0707


443
0.00896


444
0.0699


445
0.0229


446
0.0612


447
0.0125


448
0.0678


449
0.0236


450
0.0701


451
0.0173


452
0.0592


453
0.00921


454
0.0422


455
0.0035


456
0.0496


457
0.194


458
0.183


459
0.0777


460
0.0509


461
0.0314


462
0.00743


463
0.234


464
0.00679


465
0.000319


466
0.00431


467
0.00402


468
2.93


469
3.38


470
0.936


471
6.51


472
0.963


473
7.85


474
0.879


475
0.00692


476
0.00942


477
0.00321


478
0.0312


479
0.00808


480
0.00743


481
0.00579


482
0.00222


483
0.0124


484
0.00959


485
0.0345


486
0.0233


487
0.0833


488
0.0983


489
>10


490
0.0899


491
7.83


492
1.27


493
0.486


494
1.22


495
0.127


496
7.14


497
0.742


498
0.0179


499
0.00219


500
0.0217


501
0.00596


502
0.0165


503
0.00421


504
0.0154


505
0.0305


506
0.0180018


507
0.0032


508
0.0285902


509
0.00747


510
0.0121


511
0.00278


512
0.0179


513
0.0011805


514
0.0308


515
0.0158


516
0.021279


517
0.0722


518
0.0348


519
0.0609


520
0.101


521
0.0935


522
0.00673


523
0.0171


524
0.00246


525
0.00677


526
0.0603


527
0.0598


528
0.024


529
0.227


530
0.0821


531
0.0529


532
0.0927


533
0.0174


534
0.00508


535
0.0285


536
0.00304


537
0.0431


538
0.00333


539
0.00347


540
0.074


541
0.0645


542
0.00289


543
0.386


544
0.647


545
0.0287


546
2.45


547
0.0255558


548
0.0744613


549
0.009417


550
0.1741494


551
0.0550545


552
0.0425577


553
0.103


554
0.177


555
0.0332


556
0.00655


557
0.0374


558
1.17


559
0.0943


560
0.844


561
0.24


562
0.0709


563
5.14


564
0.211


565
0.891


566
>10


567
0.237


568
0.18


569
0.226


570
0.00735


571
0.0229


572
0.00666


573
0.00372


574
0.005201


575
>10


576
.000569


577
0.00215


578
4.6


579
0.758


580
0.212


581
0.0812


582
0.0332


583
0.189


584
0.0587


585
0.0346


586
0.301


587
0.00754


588
0.181


589
0.00131


590
0.189


591
0.0193


592
0.00375


593
0.677


594
0.00111


595
0.00693


596
0.257


597
0.0335


598
0.0166


599
0.0523


600
0.11


601
0.0567


602
0.0486107


603
0.695


604
0.0101


605
0.0661


606
0.0348


607
0.0744


608
0.148


609
0.142


610
0.0744


611
0.0709


612
0.695


613
0.14


614
0.00572


615
0.0188


616
0.0326


617
0.0826


618
0.125


619
0.0033


620
0.131


621
0.0253


622
0.00706


623
0.446


624
0.329


625
0.226


626
0.0807


627
0.0175


628
0.0436


629
0.0652


630
0.0404


631
0.0772


632
0.0323


633
0.012


634
0.0835


635
0.05


636
0.0184


637
0.0811


638
0.00261


639
0.0581


640
0.05


641
0.00999


642
0.0949


643
0.0069


644
0.00408


645
0.034


646
0.13


647
0.00699


648
0.203


649
0.0706


650
0.0583


651
0.0648


652
0.0346


653
0.715


654
0.0679


655
0.0688


656
0.0385


657
0.036


658
0.0608


659
0.223


660
0.0709


661
0.0672


662
0.0934


663
0.09


664
0.0715


665
0.00728


666
0.00518


667
0.0458


668
0.0803


669
0.686


670
0.00992


671
0.684


672
0.08


673
0.122


674
0.0324


675
0.0698


676
0.0787


677
6.13E−04


678
0.0151


679
0.0109


680
0.629


681
0.145


682
0.771


683
0.0361


684
0.32


685
0.074


686
0.0772


687
0.00219


688
5.48


689
0.00721


690
0.0138


691
0.0777


692
0.0198


693
0.652


694
0.0247


695
0.00582


696
0.667


697
0.633


698
0.000670


699
0.00527


700
0.00325


701
0.0761902


702
0.088


703
0.0903


704
0.0915


705
0.0958


706
0.00654


707
0.0741


708
0.00597


709
0.00336


710
0.00276


711
0.00325


712
0.0058


713
0.00286


714
0.0174


715
0.00349


716
0.021


717
0.0724


718
0.00125


719
0.00237


720
0.00582


721
0.0307


722
0.00388


723
0.0716


724
0.0632


725
0.006


726
0.0719


727
0.0582


728
0.021


729
0.0459


730
0.0295


731
0.05


732
0.0059


733
0.0202


734
0.000553


735
0.688


736
8.36


737
0.00405


738
0.0859


739
0.0676


740
0.00813


741
0.0749


742
0.0105


743
0.00681


744
0.505


745
0.632


746
0.116


747
0.942


748
0.0507


749
0.077


750
0.794


751
0.755


752
6.66


753
0.0746


754
0.00125


755
0.00249


756
0.0189


757
0.000435


758
0.0232


759
0.00165


760
0.00119


761
0.0277


762
0.00112


763
0.00231


764
0.0687


765
0.00291


766
0.00636


767
0.0672


768
0.000905


769
0.00526


770
0.006


771
0.00347


772
0.0024


773
0.00953


774
0.00707


775
0.0609


776
0.0021


111
0.00126


778
0.000896


779
0.000499


780
0.0817


781
0.00727


782
0.0247


783
0.0098


784
0.00238


785
0.000839


786
0.00751


787
0.00675


788
0.00544


789
0.0694


790
0.0026


791
0.000898


792
0.00957


793
0.00102


794
0.000883


795
0.0062


796
0.00465


797
0.00698


798
0.00963


799
0.00696


800
0.00621


801
0.0573


802
0.00583


803
0.0176


804
0.0497


805
7.82


806
1.4


807
0.1


808
0.0011


809
0.0332


810
0.327


811
0.0114


812
0.0388


813
0.00221


814
0.0045


815
0.00589


816
0.00482


817
0.00927


818
0.716


819
0.013


820
0.802


821
0.192


822
0.0711


823
0.00462


824
0.0124


825
0.00106


826
0.00679


827
0.000625


828
0.00644


829
0.00177


830
0.000269


831
0.000886


832
0.0101


833
0.07


834
0.0127


835
0.00395


836
0.0683


837
0.00277


838
0.0027


839
0.000607


840
0.00275


841
0.00613


842
0.0714


843
0.0172


844
0.0148172


845
0.00389


846
0.0744


847
0.0936


848
0.0292


849
0.0636


850
0.054


851
0.133


852
0.00832


853
0.00996


854
0.000414


855
0.111


856
0.657


857
0.00155


858
0.00059


859
0.0104


860
0.00824


861
0.000574


862
0.000780


863
0.000642


864
0.0672


865
0.000861


866
0.000525


867
0.0687


868
0.0869


869
6.87


870
0.994


871
7.3


872
>10


873
3.87


874
6.65


875
1.14


876
0.0477


877
>10


878
>10


879
0.0633


880
0.75


881
8.49


882
>10


883
0.000220


884
0.000968


885
0.005333


886
0.000194


887
0.000214


888
0.000494


889
0.651


890
0.0318


891
0.0872


892
0.00676


893
0.000662


894
0.202


895
0.73


896
1.58


897
0.716


898
0.223


899
0.181


900
0.0174


901
0.865


902
0.0108


903
0.0352


904
0.282


905
0.000994


906
0.00417


907
0.00709


908
0.0112


909
7.21


910
>10


911
0.0425


912
0.008725


913
0.0144


914
0.0772


915
0.174


916
0.00673


917
0.00679


918
0.233


919
0.101


920
0.00794


921
0.157


922
0.00995


923
0.00458


924
0.018


925
0.00206


926
0.00969


927
0.00713


928
0.106


929
0.0247


930
0.00209


931
0.00677


932
0.0303


933
0.0717


934
0.00638


935
0.0103


936
0.0325


937
0.0809


938
0.00627


939
>10


940
0.000691


941
0.000519


942
0.00102


943
0.0244


944
0.00336


945
0.00238


946
0.00594


947
0.00328


948
0.00539


949
0.0254


950
0.634


951
0.0639


952
0.0103


953
0.00235


954
0.00276


955
0.00256


956
0.00883


957
0.00351


958
0.0214


959
0.00976


960
0.00613


961
0.00894


962
0.0161


963
0.0195


964
0.00622


965
0.00831


966
0.00209


967
0.00396


968
0.00177


969
0.00636


970
0.0109


971
0.0226


972
0.0289


973
0.0218


974
0.0287


975
0.0503


976
0.0349


977
0.00265


978
0.00202


979
0.0757


980
0.0294


981
0.00654


982
0.1


983
0.724


984
0.0554


985
0.0283


986
0.0214


987
0.543


988
0.0601


989
0.0682


990
0.0179


991
0.0669


992
0.584


993
0.074


994
0.0121


995
0.0108


996
0.062


997
0.0194


998
0.123


999
0.684


1000
0.0818


1001
0.0953


1002
0.154


1003
0.00496


1004
0.0567


1005
0.0747


1006
0.0737


1007
0.0373


1008
0.00294


1009
0.0012


1010
0.0058


1011
0.00197


1012
0.00836


1013
0.00232


1014
0.00207


1015
0.00168


1016
0.00219


1017
0.00229


1018
0.00164


1019
0.00198


1020
0.000901


1021
0.00111


1022
0.00293


1023
0.00687


1024
0.00352


1025
0.000808


1026
0.00156


1027
0.00228


1028
0.00736


1029
0.000272


1030
0.002040


1031
0.00773


1032
0.00888


1033
0.00197


1034
0.00629


1035
0.00304


1036
0.016


1037
0.00776


1038
0.00784


1039
0.00687


1040
0.0134


1041
0.00241


1042
0.00359


1043
0.0104


1044
0.000892


1045
0.00669


1046
0.00461


1047
0.000205


1048
0.00827


1049
0.00239


1050
0.0234


1051
0.000313


1052
0.0271


1053
0.00341


1054
0.026


1055
0.00438


1056
0.0013


1057
0.0258


1058
0.00249


1059
0.0164


1060
0.00229


1061
0.00784


1062
0.017


1063
0.00189


1064
0.00412


1065
0.00143


1066
0.0057


1067
0.37


1068
0.00577


1069
0.00123


1070
0.000857


1071
0.000473


1072
0.00624


1073
0.00388


1074
0.0144


1075
0.00762


1076
0.0057


1077
0.0691


1078
0.00761


1079
0.0182


1080
0.00341


1081
0.195


1082
0.00218


1083
0.000920


1084
0.0148


1085
0.0256


1086
0.00993


1087
0.00168


1088
0.0344


1089
0.00827


1090
0.00542


1091
0.00419


1092
0.0177


1093
0.565


1094
0.0688


1095
0.00445


1096
0.00207


1097
0.0647


1098
0.00955


1099
0.0156


1100
0.0087


1101
0.00206


1102
0.00177


1103
0.00424


1104
0.00696


1105
0.0026


1106
0.0275


1107
0.00226


1108
0.0201


1109
0.00921


1110
0.111


1111
0.062


1112
0.0164


1113
0.0231


1114
0.0218


1115
0.0212


1116
0.00619


1117
0.0657


1118
0.00418


1119
0.00667


1120
0.00237


1121
0.00842


1122
0.00996


1123
0.00711


1124
0.000344


1125
0.00477


1126
0.00236


1127
0.00299


1128
0.00605


1129
0.00805


1130
0.00296


1131
0.0344


1132
0.00896


1133
0.001


1134
0.00551


1135
0.00423


1136
0.00302


1137
0.000277


1138
0.00385


1139
0.00141


1140
0.00584


1141
0.0022


1142
0.0029


1143
0.0174


1144
0.0096


1145
0.00704


1146
0.00188


1147
0.00283


1148
0.00272


1149
0.00262


1150
0.0641


1151
0.00778


1152
0.00308


1153
0.00172
























































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































Compounds which inhibit NAMPT are useful for treating diseases in which activation of NF-KB is implicated. Such methods are useful in the treatment of a variety of diseases including inflammatory and tissue repair disorders; particularly rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis and fibrotic diseases; dermatosis, including psoriasis, atopic dermatitis and ultra-violet induced skin damage; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, athersclerosis, restenosis, diabetes, glomerulonephritis, cancer, particularly wherein the cancer is selected from breast, prostate, lung, colon, cervix, ovary, skin, CNS, bladder, pancreas, leukaemia, lymphoma or Hodgkin's disease, cachexia, inflammation associated with infection and certain viral infections, including Acquired Immune Deficiency Syndrome (AIDS), adult respiratory distress syndrome, and ataxia telengiectasia.
Involvement of NAMPT in the treatment of cancer is described in WO 97/48696. Involvement of NAMPT in immuno-supression is described in WO 97/48397. Involvement of NAMPT for the treatment of diseases involving angiogenesis is described in WO 2003/80054. Involvement of NAMPT for the treatment of rheumatoid arthritis and septic shock is described in WO 2008/025857. Involvement of NAMPT for the prophlaxis and treatment of ischaemia is described in WO 2009/109610.
Cancers include, but are not limited to, hematologic and solid tumor types such as acoustic neuroma, acute leukemia, acute lymphoblastic leukemia, acute myelogenous leukemia (monocytic, myeloblastic, adenocarcinoma, angiosarcoma, astrocytoma, myelomonocytic and promyelocytic), acute t-cell leukemia, basal cell carcinoma, bile duct carcinoma, bladder cancer, brain cancer, breast cancer (including estrogen-receptor positive breast cancer), bronchogenic carcinoma, Burkitt's lymphoma, cervical cancer, chondrosarcoma, chordoma, choriocarcinoma, chronic leukemia, chronic lymphocytic leukemia, chronic myelocytic (granulocytic) leukemia, chronic myelogenous leukemia, colon cancer, colorectal cancer, craniopharyngioma, cystadenocarcinoma, dysproliferative changes (dysplasias and metaplasias), embryonal carcinoma, endometrial cancer, endotheliosarcoma, ependymoma, epithelial carcinoma, erythroleukemia, esophageal cancer, estrogen-receptor positive breast cancer, essential thrombocythemia, Ewing's tumor, fibrosarcoma, gastric carcinoma, germ cell testicular cancer, gestational trophobalstic disease, glioblastoma, head and neck cancer, heavy chain disease, hemangioblastoma, hepatoma, hepatocellular cancer, hormone insensitive prostate cancer, leiomyosarcoma, liposarcoma, lung cancer (including small cell lung cancer and non-small cell lung cancer), lymphangioendothelio-sarcoma, lymphangiosarcoma, lymphoblastic leukemia, lymphoma (lymphoma, including diffuse large B-cell lymphoma, follicular lymphoma, Hodgkin's lymphoma and non-Hodgkin's lymphoma), malignancies and hyperproliferative disorders of the bladder, breast, colon, lung, ovaries, pancreas, prostate, skin and uterus, lymphoid malignancies of T-cell or B-cell origin, leukemia, medullary carcinoma, medulloblastoma, melanoma, meningioma, mesothelioma, multiple myeloma, myelogenous leukemia, myeloma, myxosarcoma, neuroblastoma, oligodendroglioma, oral cancer, osteogenic sarcoma, ovarian cancer, pancreatic cancer, papillary adenocarcinomas, papillary carcinoma, peripheral T-cell lymphoma, pinealoma, polycythemia vera, prostate cancer (including hormone-insensitive (refractory) prostate cancer), rectal cancer, renal cell carcinoma, retinoblastoma, rhabdomyosarcoma, sarcoma, sebaceous gland carcinoma, seminoma, skin cancer, small cell lung carcinoma, solid tumors (carcinomas and sarcomas), stomach cancer, squamous cell carcinoma, synovioma, sweat gland carcinoma, testicular cancer (including germ cell testicular cancer), thyroid cancer, Waldenström's macroglobulinemia, testicular tumors, uterine cancer, Wilms' tumor and the like.
Schemes and Experimentals
The following abbreviations have the meanings indicated. ADDP means 1,1′-(azodicarbonyl)dipiperidine; AD-mix-13 means a mixture of (DHQD) 2 PHAL, K 3 Fe(CN) 6 , K 2 CO 3 , and K 2 SO 4 ; 9-BBN means 9-borabicyclo(3.3.1)nonane; Boc means tert-butoxycarbonyl; (DHQD) 2 PHAL means hydroquinidine 1,4-phthalazinediyl diethyl ether; DBU means 1,8-diazabicyclo[5.4.0]undec-7-ene; DIBAL means diisobutylaluminum hydride; DIEA means diisopropylethylamine; DMAP means N,N-dimethylaminopyridine; DMF means N,N-dimethylformamide; dmpe means 1,2-bis(dimethylphosphino)ethane; DMSO means dimethylsulfoxide; dppb means 1,4-bis(diphenylphosphino)-butane; dppe means 1,2-bis(diphenylphosphino)ethane; dppf means 1,1′-bis(diphenylphosphino)ferrocene; dppm means 1,1-bis(diphenylphosphino)methane; EDAC.HCl means 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Fmoc means fluorenylmethoxycarbonyl; HATU means 0-(7-azabenzotriazol-1-yl)-N,N′N′N′-tetramethyluronium hexafluorophosphate; HMPA means hexamethylphosphoramide; IPA means isopropyl alcohol; MP-BH 3 means macroporous triethylammonium methylpolystyrene cyanoborohydride; TEA means triethylamine; TFA means trifluoroacetic acid; THF means tetrahydrofuran; NCS means N-chlorosuccinimide; NMM means N-methylmorpholine; NMP means N-methylpyrrolidine; PPh 3 means triphenylphosphine.
The following schemes are presented to provide what is believed to be the most useful and readily understood description of procedures and conceptual aspects of this invention. Compounds of this invention may be made by synthetic chemical processes, examples of which are shown herein. It is meant to be understood that the order of the steps in the processes may be varied, that reagents, solvents and reaction conditions may be substituted for those specifically mentioned, and that vulnerable moieties may be protected and deprotected, as necessary.
Schemes









As shown in Scheme 1, compounds of formula (1), wherein R 4 is as described herein, can be reacted with 4-nitrobenzoic acid in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, to provide compounds of formula (2). The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide. Compounds of formula (3) can be prepared by reacting compounds of formula (2) with hydrogen in the presence of palladium on carbon. The reaction is typically performed at ambient temperature in a solvent such as but not limited to methanol. Compounds of formula (3) can be reacted with compounds of formula (4) wherein X and Z are as described herein, to provide compounds of formula (5). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
Alternatively, Compounds of formula (3) can be reacted with compounds of formula (6) wherein X is as described herein, to provide compounds of formula (7). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.









Compounds of formula (8), wherein R x is as described herein for substituents on the R 3 phenyl, can be reacted with compounds of formula (9), wherein X and Z are as described herein, to provide compounds of formula (10). The reaction is typically performed in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide.
Similarly, compounds of formula (8), wherein Rx is as described herein for substituents on the R 3 phenyl, can be reacted with compounds of formula (11), wherein X is as described herein, to provide compounds of formula (12). The reaction is typically performed in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide.









As shown in Scheme 3, compounds of formula (13), wherein R 3 is as described herein, can be reacted with compounds of formula (11), wherein X is as described herein, in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine to provide compounds of formula (14). The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.
Alternatively, compounds of formula (13), wherein R 3 is as described herein, can be reacted with compounds of formula (9), wherein X and Z are as described herein, in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine to provide compounds of formula (14). The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.









2-Bromo-5-thiazolecarboxylic acid can be reacted with compounds of formula (9), wherein X and Z are as described herein, in the presence of a base such as but not limited to N-methylmorpholine, an ester activating agent such as but not limited to 1-hydroxybenzotriazole hydrate, and a carboxyl activating agent such as but not limited to N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, to provide compounds of formula (16). The reaction is typically performed at ambient temperature in a solvent such as but not limited to dimethylformamide. Compounds of formula (16) can be reacted with amines of formula (1) wherein R 4 is as described herein, to provide compounds of formula (17). The reaction is typically performed at an elevated temperature in a solvent such as but not limited to acetonitrile and may be performed in a microwave oven. Compounds of formula (19), which are representative of the compounds of this invention, can be prepared by reacting compounds of formula (17) with compounds of formula (18), wherein R 4 is as described herein, in the presence of a base such as but not limited to diisopropylethylamine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to tetrahydrofuran. Alternatively, compounds of formula (17) can be reacted with amines of formula (4), wherein R 4 is as described herein, to provide compounds of formula (20), which are representative of the compounds of Formula (I). The reaction is typically performed in the presence of bis(2,5-dioxopyrrolidin-1-yl) carbonate and a base such as but not limited to pyridine. The reaction is typically performed at ambient temperature in a solvent such as but not limited to N-methyl-2-pyrrolidinone.









As shown in Scheme 5, compounds of formula (16), which can be prepared as described in Scheme 4 and wherein X and Z are as described herein, can be reacted with suitable boronic acids (or the equivalent boronic ester) of formula (21) wherein R 4 is as described herein, under Suzuki coupling conditions known to those skilled in the art and widely available in the literature, to provide compounds of formula (22), which are representative of the compounds of Formula (I).
EXAMPLES
The following examples are presented to provide what is believed to be the most useful and readily understood description of procedures and conceptual aspects of this invention. Each exemplified compound and intermediate was named using ACD/ChemSketch Version 12.5 (20 Apr. 2011), Advanced Chemistry Development Inc., Toronto, Ontario), or ChemDraw® Ver. 9.0.7 (CambridgeSoft, Cambridge, Mass.). Experimentals
Example 1
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide
Example 1A
N-isopentyl-4-nitrobenzamide
4-Nitrobenzoic acid (0.8 g, 4.79 mmol) and 1-hydroxybenzotriazole hydrate (1.1 g, 7.18 mmol) in dimethylformamide (20 mL) was treated with N-methylmorpholine (1.8 mL, 16.75 mmol) and 3-methylbutan-1-amine (0.724 mL, 6.22 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.38 g, 7.18 mmol). The reaction mixture was stirred at room temperature for 17 hours. Water was added and the resulting suspension was stirred for 2 hours. The suspension was filtered and the solid collected was washed with water and dried to provide the title compound.
Example 1B
4-amino-N-isopentylbenzamide
N-Isopentyl-4-nitrobenzamide (1 g, 4.23 mmol) and methanol (40 ml) were added to palladium on carbon (0.200 g, 1.879 mmol) in a 250 mL SS pressure bottle and the mixture was stirred for 6 hours with hydrogen at 30 psi and room temperature. The mixture was filtered through a nylon membrane and concentrated to provide the title compound.
Example 1C
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide
A solution of 4-amino-N-isopentylbenzamide (0.05 g, 0.242 mmol), bis(2,5-dioxopyrrolidin-1-yl) carbonate (0.078 g, 0.303 mmol) and pyridine (0.020 ml, 0.242 mmol) in N-methyl-2-pyrrolidinone (0.6 mL) was stirred at room temperature for 1 hour. Diisopropylethylamine (0.127 ml, 0.727 mmol) was added followed by addition of a solution of imidazo[1,2-a]pyridin-6-amine (0.041 g, 0.279 mmol) in N-methyl-2-pyrrolidinone (0.6 mL) dropwise by syringe over 5 minutes. The reaction mixture was stirred for 16 hours at room temperature and the mixture was treated with water. The resulting suspension was stirred for 5 minutes and filtered with water washes. Vacuum drying and reverse phase chromatography provided the title compound. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04-8.93 (m, 2H), 8.76 (bs, 1H), 8.24 (t, J=5.5 Hz, 1H), 7.96 (s, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.58-7.45 (m, 4H), 7.09 (dd, J=9.6, 2.0 Hz, 1H), 3.33-3.20 (m, 2H), 1.68-1.52 (m, 1H), 1.46-1.35 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 366 (M+H) + .
Example 2
4-[(imidazo[1,2-a]pyridin-7-ylcarbamoyl)amino]-N-(3-methylbutyl)benzamide
The title compound was prepared as described in Example 1C, substituting imidazo[1,2-a]pyridin-7-amine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04 (m, 2H), 8.42 (dd, J=7.5, 0.6 Hz, 1H), 8.25 (t, J=5.5 Hz, 1H), 7.78 (m, 4H), 7.53 (d, J=8.7 Hz, 2H), 7.42 (d, J=1.2 Hz, 1H), 6.90 (dd, J=7.3, 2.1 Hz, 1H), 3.30-3.21 (m, 2H), 1.69-1.54 (m, 1H), 1.47-2.36 (m, 2H), 0.91 (d, J=6.5 Hz, 6H); MS (ESI(+)) m/e 366 (M+H) + .
Example 3
2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide
Example 3A
1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-nitrophenyl)urea
A 0° C. solution of imidazo[1,2-a]pyridin-6-amine (1 g, 7.21 mmol), N-ethyl-N-isopropylpropan-2-amine (2.51 ml, 14.42 mmol) and dimethylformamide (21.85 ml) was treated with a solution of 1-isocyanato-4-nitrobenzene (1.313 g, 8.00 mmol) in tetrahydrofuran (10.92 ml) which was added dropwise via syringe over 5 minutes. The reaction mixture was allowed to stir at room temperature for 6 hours, and water was added. The suspension was filtered with water washes to give the title compound after vacuum drying.
Example 3B
1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-yl)urea
The title compound was prepared as described in Example 1B, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-nitrophenyl)urea for N-isopentyl-4-nitrobenzamide.
Example 3C
2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}acetamide
The title compound was prepared as described in Example 1A, substituting 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-yl)urea for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 9.73 (bs, 1H), 8.96 (m, 1H), 8.66 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H), 7.57-7.44 (m, 4H), 7.37 (d, J=8.9 Hz, 2H), 7.07 (dd, J=9.6, 2.0 Hz, 1H), 2.29-2.15 (m, 3H), 1.82-1.68 (m, 2H), 1.68-1.45 (m, 4H), 1.29-1.07 (m, 2H); MS (ESI(+)) m/e 378 (M+H) + .





TABLE 1



The following Examples were prepared essentially as described in Example 3,

substituting the appropriate carboxylic acid in Example 1C. Some products were purified by

flash chromatography while others were purified by reverse-phase HPLC. Accordingly,

some Examples were isolated as trifluoroacetic acid salts.






Ex
Name
1 H NMR
MS



26
N-{4-[(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.49 (bs, 1H),
m/e 380


ylcarbamoyl)amino]phen
8.84 (m, 1H), 8.44 (m, 2H), 7.85
(M + H) +


yl}-2-(tetrahydrofuran-3-
(s, 1H), 7.52-7.44 (m, 4H), 7.39-



yl)acetamide
7.29 (m, 2H), 7.09 (dd, J = 9.6,




2.1 Hz, 1H), 3.83-3.72 (m, 2H),




3.68-3.62 (m, 1H), 3.38-3.33




(m, 1H), 2.57 (m, 1H), 2.40-2.33




(m, 2H), 2.08-1.95 (m, 1H), 1.62-




1.52 (m, 1H)


27
N-{4-[(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ
(ESI(+))


a]pyridin-6-
ppm δ 9.81 (s, 1H), 8.98-8.93
m/e 310


ylcarbamoyl)amino]phen
(m, 1H), 8.70-8.62 (m, 2H), 7.96-
(M + H) +


yl}acetamide
7.93 (m, 1H), 7.53-7.45 (m,




4H), 7.41-7.33 (m, 2H), 7.07 (dd,




J = 9.5, 2.0 Hz, 1H), 2.01 (s, 3H)


39
2-ethoxy-N-{4-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


[(imidazo[1,2-a]pyridin-
Temp = 90° C.) δ ppm 9.57 (s, 1H),
m/e 354


6-
8.96 (m, 1H), 8.69 (s, 1H), 8.64 (s,
(M + H) +


ylcarbamoyl)amino]phen
1H), 7.95 (s, 1H), 7.60-7.48 (m,



yl}acetamide
4H), 7.42-7.37 (m, 2H), 7.07 (dd,




J = 9.6, 2.0 Hz, 1H), 4.00 (s, 2H),




3.56 (q, J = 7.0 Hz, 2H), 1.19 (t, J =




7.0 Hz, 3H)


40
N-{4-[(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,) δ
(ESI(+))


a]pyridin-6-
ppm 9.79 (s, 1H), 8.98-8.93 (m,
m/e 394


ylcarbamoyl)amino]phen
1H), 8.67 (s, 1H), 8.63 (s, 1H),
(M + H) +


yl}-2-(tetrahydro-2H-
7.97-7.93 (m, 1H), 7.54-7.46



pyran-4-yl)acetamide
(m, 4H), 7.40-7.34 (m, 2H), 7.07




(dd, J = 9.5, 2.0 Hz, 1H), 3.87-




3.79 (m, 2H), 3.34-3.26 (m, 2H),




2.25-2.19 (m, 2H), 2.07-1.91




(m, 1H), 1.63-1.54 (m, 2H), 1.31-




1.17 (m, 2H)


41
N-{4-[(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.35 (bs, 1H),
m/e 395


ylcarbamoyl)amino]phen
8.85 (m, 1H), 8.50-8.30 (M, 2H),
(M + H) +


yl}-2-(morpholin-4-
7.86 (s, 1H), 7.55-7.43 (m, 4H),



yl)acetamide
7.41-7.34 (m, 2H), 7.09 (dd, J =




9.5, 2.0 Hz, 1H), 3.68-3.60 (m,




4H), 3.09 (s, 2H), 2.56-2.51 (m,




4H)


42
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 384


ylcarbamoyl)amino]phen

(M + H) +


yl}-2-(2-




methoxyethoxy)acetamide



43
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 368


ylcarbamoyl)amino]phen

(M + H) +


yl}-3-methoxy-2-




methylpropanamide



44
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 338


ylcarbamoyl)amino]phen

(M + H) +


yl}butanamide



45
4,4,4-trifluoro-N-{4-

(ESI(+))


[(imidazo[1,2-a]pyridin-

m/e 392


6-

(M + H) +


ylcarbamoyl)amino]phen




yl}butanamide



46
-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 380


ylcarbamoyl)amino]phen

(M + H) +


yl}tetrahydro-2H-pyran-




4-carboxamide



47
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 366


ylcarbamoyl)amino]phen

(M + H) +


yl}-4-methylpentanamide



48
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 393


ylcarbamoyl)amino]phen

(M + H) +


yl}-1-methylpiperidine-4-




carboxamide



49
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 428


ylcarbamoyl)amino]phen

(M + H) +


yl}tetrahydro-2H-




thiopyran-4-carboxamide




1,1-dioxide



50
N-{4-[(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 382


ylcarbamoyl)amino]phen

(M + H) +


yl}-1,4-dioxane-2-




carboxamide













































































































Example 4
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide
Example 4A
methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate
The title compound was prepared as described in Example 3A, substituting methyl 4-isocyanatobenzoate for 1-isocyanato-4-nitrobenzene.
Example 4B
4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoic acid
A solution of methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate (2.1 g, 6.77 mmol) in tetrahydrofuran (18.05 ml) and methanol (9.02 ml) was treated with 2N lithium hydroxide (13.53 ml, 27.1 mmol) and the reaction was allowed to stir at room temperature for 16 hours. The mixture was concentrated, redissolved in 225 mL water and acidified to pH 4 with 3N hydrochloric acid. The suspension was filtered with water washes to give the title compound after vacuum drying.
Example 4C
4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]-N-(2-phenylethyl)benzamide
The title compound was prepared as described in Example 1A, substituting 2-phenylethanamine for 3-methylbutan-1-amine and 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 /D 2 O, Temp=90° C.) δ ppm 9.33 (dd, J=1.9, 0.8 Hz, 1H), 8.32 (d, J=1.8 Hz, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.90 (d, J=9.7 Hz, 1H), 7.85-7.74 (m, 3H), 7.61-7.51 (m, 2H), 7.35-7.20 (m, 5H), 3.49 (dd, J=8.1, 6.9 Hz, 2H), 2.94-2.79 (m, 2H); MS (ESI(+)) m/e 400 (M+H) + .





TABLE 2



The following Examples were prepared essentially as described in Example 4,

substituting the appropriate amine in Example 4C. Some products were purified by flash

chromatography while others were purified by reverse-phase HPLC. Accordingly, some

Examples were isolated as trifluoroacetic acid salts.






Ex
Name
1 H NMR
MS








5
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.37 (dd, J = 2.0, 0.9
m/e 409


ylcarbamoyl)
Hz, 1H), 8.36 (d, J = 2.1 Hz, 1H), 8.10 (d, J =
(M + H) +


amino]-N-[2-
2.1 Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 7.88-



(morpholin-4-
7.78 (m, 3H), 7.71-7.57 (m, 2H), 4.02



yl)ethyl]benzamide
(d, J = 11.3 Hz, 2H), 3.66 (dd, J = 16.1,




10.0 Hz, 4H), 3.56 (d, J = 11.3 Hz, 2H),




3.33 (t, J = 6.1 Hz, 2H), 3.17 (d, J = 13.5




Hz, 2H), 2.70 (s, 2H)


6
N-(1-hydroxy-2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


methylpropan-2-
Temp = 90° C.) δ ppm 9.36 (t, J = 6.6 Hz, 1H),
m/e 368


yl)-4-
8.34 (d, J = 1.9 Hz, 1H), 8.09 (dd, J = 10.9,
(M + H) +


[(imidazo[1,2-
5.4 Hz, 1H), 7.90 (t, J = 10.7 Hz, 1H), 7.85-



a]pyridin-6-
7.73 (m, 3H), 7.56 (dd, J = 12.5, 5.6 Hz,



ylcarbamoyl)
2H), 3.51 (s, 2H), 1.49-1.23 (m, 6H)



amino]benzamide



7
N-benzyl-4-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


[(imidazo[1,2-
Temp = 90° C.) δ ppm 9.38-9.29 (m, 1H),
m/e 386


a]pyridin-6-
8.33 (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz,
(M + H) +


ylcarbamoyl)
1H), 7.96-7.85 (m, 3H), 7.77 (td, J = 9.4,



amino]benzamide
1.5 Hz, 1H), 7.66-7.51 (m, 2H), 7.38-




7.31 (m, 4H), 7.32-7.19 (m, 1H), 4.48 (s,




2H)


8
N-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


(cyclopentyl-
Temp = 90° C.) δ ppm 9.41-9.31 (m, 1H),
m/e 378


methyl)-4-
8.34 (d, J = 2.0 Hz, 1H), 8.07 (d, J = 2.0 Hz,
(M + H) +


[(imidazo[1,2-
1H), 7.91 (d, J = 8.9 Hz, 1H), 7.86-7.73



a]pyridin-6-
(m, 3H), 7.63-7.51 (m, 2H), 3.19 (d, J =



ylcarbamoyl)
7.4 Hz, 2H), 2.24-2.01 (m, 1H), 1.68 (dt, J =



amino]benzamide
11.6, 7.2 Hz, 2H), 1.64-1.57 (m, 2H),




1.57-1.42 (m, 2H), 1.37-1.14 (m, 2H)


9
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.36 (d, J = 1.4 Hz,
m/e 421


ylcarbamoyl)
1H), 8.35 (d, J = 2.0 Hz, 1H), 8.10 (d, J =
(M + H) +


amino]-N-[3-
2.1 Hz, 1H), 7.94 (d, J = 9.7 Hz, 1H), 7.88-



(piperidin-1-
7.80 (m, 3H), 7.66-7.53 (m, 2H), 3.44 (d,



yl)propyl]
J = 12.2 Hz, 2H), 3.34 (t, J = 6.6 Hz, 2H),



benzamide
3.12-3.02 (m, 2H), 2.97-2.85 (m, 2H),




2.02-1.81 (m, 4H), 1.81-1.58 (m, 4H),




1.51-1.31 (m, 1H)


10
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.36 (dd, J = 6.3, 5.4
m/e 411


ylcarbamoyl)
Hz, 1H), 8.35 (d, J = 2.1 Hz, 1H), 8.09 (d, J =
(M + H) +


amino]-N-(2-
2.0 Hz, 1H), 7.92 (d, J = 9.8 Hz, 1H), 7.89-



phenoxyethyl)
7.80 (m, 3H), 7.63-7.55 (m, 2H), 7.30



benzamide
(dd, J = 8.4, 7.4 Hz, 2H), 6.95 (dd, J = 11.9,




7.8 Hz, 3H), 4.12 (t, J = 5.8 Hz, 2H), 3.64




(t, J = 5.8 Hz, 2H)


11
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.34 (s, 1H), 8.34 (d, J =
m/e 393


ylcarbamoyl)
2.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 7.92
(M + H) +


amino]-N-[2-
(d, J = 9.1 Hz, 1H), 7.88-7.78 (m, 3H),



(pyrrolidin-1-
7.59 (dd, J = 16.4, 8.7 Hz, 2H), 3.59 (dd, J =



yl)ethyl]
15.8, 9.8 Hz, 4H), 3.33 (t, J = 6.0 Hz,



benzamide
2H), 3.07 (d, J = 11.0 Hz, 2H), 2.05 (s, 2H),




1.97-1.74 (m, 2H)


12
-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.35 (d, J = 1.3 Hz,
m/e 382


ylcarbamoyl)
1H), 8.34 (d, J = 2.0 Hz, 1H), 8.08 (d, J =
(M + H) +


amino]-N-[2-
2.0 Hz, 1H), 7.92 (d, J = 9.7 Hz, 1H), 7.88-



(propan-2-
7.77 (m, 3H), 7.63-7.52 (m, 2H), 3.64-



yloxy)ethyl]
3.55 (m, 1H), 3.51 (dd, J = 20.1, 13.7 Hz,



benzamide
2H), 3.39 (t, J = 6.2 Hz, 2H), 1.09 (d, J =




6.1 Hz, 6H)


13
N-(2-hydroxy-2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


methylpropyl)-
Temp = 90° C.) δ ppm 9.37-9.31 (m, 1H),
m/e 368


4-[(imidazo[1,2-
8.33 (d, J = 1.9 Hz, 1H), 8.06 (d, J = 2.0 Hz,
(M + H) +


a]pyridin-6-
1H), 7.96-7.88 (m, 1H), 7.88-7.81 (m,



ylcarbamoyl)
2H), 7.76 (dd, J = 9.6, 1.9 Hz, 1H), 7.65-



amino]benzamide
7.53 (m, 2H), 3.27 (s, 2H), 1.15 (d, J = 27.1




Hz, 6H)


14
N-[2-hydroxy-1-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


(4-
Temp = 90° C.) δ ppm 9.40-9.32 (m, 1H),
m/e 446


methoxyphenyl)
8.34 (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.1 Hz,
(M + H) +


ethyl]-4-
1H), 7.95-7.86 (m, 3H), 7.81-7.75 (m,



[(imidazo[1,2-
1H), 7.61-7.55 (m, 2H), 7.39-7.26 (m,



a]pyridin-6-
2H), 6.92-6.86 (m, 2H), 5.09-4.96 (m,



ylcarbamoyl)
1H), 3.72-3.67 (m, 5H), 3.66-3.60 (m,



amino]benzamide
1H)


15
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.41-9.33 (m, 1H),
m/e 407


ylcarbamoyl)
8.35 (d, J = 2.0 Hz, 1H), 8.09 (d, J = 2.1 Hz,
(M + H) +


amino]-N-[2-(2-
1H), 7.92 (d, J = 9.7 Hz, 1H), 7.82-7.72



oxopyrrolidin-1-
(m, 3H), 7.63-7.51 (m, 2H), 3.50-3.30



yl)ethyl]
(m, 6H), 2.20 (t, J = 8.1 Hz, 2H), 1.96-



benzamide
1.86 (m, 2H)


16
4-[(imidazo[1,2-
NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.39-9.29 (m, 1H),
m/e 380


ylcarbamoyl)
8.34 (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.0 Hz,
(M + H) +


amino]-N-
1H), 7.92 (d, J = 9.5 Hz, 1H), 7.86-7.77



(tetrahydrofuran-
(m, 3H), 7.63-7.53 (m, 2H), 3.99 (p, J =



2-
6.3 Hz, 1H), 3.64 (dd, J = 14.3, 7.5 Hz, 2H),



ylmethyl)
3.42-3.24 (m, 2H), 2.03-1.87 (m, 1H),



benzamide
1.89-1.75 (m, 2H), 1.66-1.52 (m, 1H)


17
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.34 (d, J = 1.3 Hz,
m/e 338


ylcarbamoyl)
1H), 8.34 (d, J = 2.0 Hz, 1H), 8.07 (d, J =
(M + H) +


amino]-N-
2.0 Hz, 1H), 7.91 (d, J = 9.6 Hz, 1H), 7.87-



propylbenzamide
7.73 (m, 3H), 7.64-7.50 (m, 2H), 3.22 (t, J =




7.1 Hz, 2H), 1.61-1.45 (m, 2H), 0.89 (t,




J = 7.4 Hz, 3H)


18
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.35 (d, J = 1.2 Hz,
m/e 423


ylcarbamoyl)
1H), 8.35 (d, J = 2.1 Hz, 1H), 8.10 (d, J =
(M + H) +


amino]-N-[3-
2.1 Hz, 1H), 7.93 (d, J = 9.7 Hz, 1H), 7.85-



(morpholin-4-
7.78 (m, 3H), 7.65-7.56 (m, 2H), 4.07-



yl)propyl]
3.96 (m, 2H), 3.66 (t, J = 12.1 Hz, 2H), 3.44



benzamide
(d, J = 12.4 Hz, 2H), 3.35 (t, J = 6.6 Hz,




2H), 3.21-3.12 (m, 2H), 3.07 (d, J = 9.4




Hz, 2H), 2.03-1.83 (m, 2H)


19
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.30 (s, 1H), 8.29 (d, J =
m/e 372


ylcarbamoyl)
1.6 Hz, 1H), 8.02-7.92 (m, 3H), 7.87 (d,
(M + H) +


amino]-N-
J = 9.6 Hz, 1H), 7.79-7.66 (m, 3H), 7.65-



phenylbenzamide
7.58 (m, 2H), 7.42-7.33 (m, 2H), 7.20-




7.05 (m, 1H)


20
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.39-9.29 (m, 1H),
m/e 366


ylcarbamoyl)
8.43-8.29 (m, 1H), 8.09-8.03 (m, 1H),
(M + H) +


amino]-N-(2-
7.96-7.89 (m, 1H), 7.87-7.75 (m, 3H),



methylbutyl)
7.66-7.50 (m, 2H), 3.25-3.16 (m, 1H),



benzamide
3.14-3.03 (m, 1H), 1.70-1.58 (m, 1H),




1.48-1.36 (m, 1H), 1.23-1.05 (m, 1H),




0.97-0.79 (m, 6H)


21
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.44-9.30 (m, 1H),
m/e 421


ylcarbamoyl)
8.34 (t, J = 5.8 Hz, 1H), 8.13-8.05 (m,
(M + H) +


amino]-N-[3-(2-
1H), 7.92 (d, J = 9.7 Hz, 1H), 7.87-7.76



oxopyrrolidin-1-
(m, 3H), 7.68-7.51 (m, 2H), 3.45-3.32



yl)propyl]
(m, 2H), 3.31-3.14 (m, 4H), 2.33-2.19



benzamide
(m, 2H), 2.02-1.87 (m, 2H), 1.80-1.63




(m, 2H)


22
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.34 (d, J = 1.2 Hz,
m/e 394


ylcarbamoyl)
1H), 8.33 (d, J = 2.0 Hz, 1H), 8.07 (d, J =
(M + H) +


amino]-N-
2.0 Hz, 1H), 7.91 (d, J = 9.6 Hz, 1H), 7.85-



(tetrahydro-2H-
7.75 (m, 3H), 7.62-7.53 (m, 2H), 3.85 (dd,



pyran-4-
J = 11.4, 2.5 Hz, 2H), 3.27 (td, J = 11.7, 1.9



ylmethyl)
Hz, 2H), 3.16 (d, J = 6.9 Hz, 2H), 1.80 (tt, J =



benzamide
11.3, 3.9 Hz, 1H), 1.59 (d, J = 11.0 Hz,




2H), 1.20 (qd, J = 12.0, 4.5 Hz, 2H)


23
4-[(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-
Temp = 90° C.) δ ppm 9.43-9.28 (m, 1H),
m/e 394


ylcarbamoyl)
8.34 (d, J = 2.0 Hz, 1H), 8.08 (d, J = 2.0 Hz,
(M + H) +


amino]-N-
1H), 7.92 (d, J = 9.7 Hz, 1H), 7.87-7.74



(tetrahydro-2H-
(m, 3H), 7.65-7.51 (m, 2H), 3.87 (dd, J =



pyran-2-
10.6, 2.6 Hz, 1H), 3.48-3.41 (m, 1H), 3.33



ylmethyl)
(td, J = 11.1, 3.3 Hz, 1H), 3.29-3.21 (m,



benzamide
2H), 1.78 (d, J = 5.1 Hz, 1H), 1.61 (d, J =




12.8 Hz, 1H), 1.54-1.38 (m, 3H), 1.18 (qd,




J = 12.1, 3.7 Hz, 1H)


24
N-[(1,1-

(ESI(+))


dioxidotetra-

m/e 428


hydrothiophen-3-

(M + H) +


yl)methyl]-4-




[(imidazo[1,2-




a]pyridin-6-




ylcarbamoyl)




amino]benzamide

























































































































































































Example 25
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate for 4-amino-N-isopentylbenzamide. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.96 (m, 1H), 8.82-8.75 (m, 1H), 8.65 (m, 1H), 7.96 (s, 1H), 7.52-7.36 (m, 6H), 7.12-7.04 (m, 1H), 6.12-6.05 (m, 1H), 4.07-3.92 (m, 2H), 3.59-3.49 (m, 2H), 2.44 (m, 2H), 1.43 (s, 9H); MS (ESI(+)) m/e 434 (M+H) + .
Example 28
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea
Example 28A
1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)urea
A solution of tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.57 g, 1.315 mmol) in dichloromethane (5 ml) was treated with trifluoroacetic acid (0.608 ml, 7.88 mmol) and the reaction mixture was stirred at room temperature for 4 hours. Concentration provided the title compound.
Example 28B
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}urea
The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)urea for 3-methylbutan-1-amine and 2-(tetrahydrofuran-3-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.96 (m, 1H), 8.82 (bs, 1H), 8.70 (bs, 1H), 7.96 (s, 1H), 7.55-7.35 (m, 6H), 7.08 (dd, J=9.6, 2.0 Hz, 1H), 6.11 (m, 1H), 4.18-4.05 (m, 2H), 3.90-3.79 (m, 1H), 3.76-3.57 (m, 4H), 3.35-3.23 (m, 2H), 2.55-2.39 (m, 4H), 2.05-1.95 (m, 1H), 1.60-1.42 (m, 1H); MS (ESI(+)) m/e 446 (M+H) + .





TABLE 3



The following Examples were prepared essentially as described in Example 28,

substituting the appropriate carboxylic acid in Example 28B. Some products were purified

by flash chromatography while others were purified by reverse-phase HPLC. Accordingly,

some Examples were isolated as trifluoroacetic acid salts.






Ex
Name
1 H NMR
MS



29
1-{4-[1-(2-
1 H NMR (300 MHz, DMSO-d 6 ,) δ ppm
(ESI(+))


hydroxy-2-
9.01-8.93 (m, 1H), 8.84 (bs, 1H), 8.71
m/e 420


methylpropanoyl)-
(bs, 1H), 7.95 (s, 1H), 7.53-7.35 (m,
(M + H) +


1,2,3,6-
6H), 7.12-7.04 (m, 1H), 6.13 (m, 1H),



tetrahydropyridin-
5.43 (bs, 1H), 4.20-3.95 (m, 2H), 3.31



4-yl]phenyl}-3-
(m, 2H), 2.58-2.45 (m, 2H), 1.34 (s, 6H)



imidazo[1,2-




a]pyridin-6-ylurea



30
1-imidazo[1,2-
1 H NMR (300 MHz, methanol-d4) δ ppm
(ESI(+))


a]pyridin-6-yl-3-
9.01-8.81 (m, 1H), 7.82 (bs, 1H), 7.54-
m/e 461


{4-[1-(morpholin-
7.49 (m, 2H), 7.48-7.32 (m, 4H), 7.18
(M + H) +


4-ylacetyl)-
(dd, J = 9.6, 2.0 Hz, 1H), 6.09 (m, 1H),



1,2,3,6-
4.31 (d, J = 2.8 Hz, 1H), 4.18 (d, J = 2.9



tetrahydropyridin-
Hz, 1H), 3.89-3.76 (m, 2H), 3.71 (m,



4-yl]phenyl}urea
4H), 3.38-3.25 (m, 2H), 2.65 (m, 1H),




2.61-2.49 (m, 5H)


31
1-{4-[1-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


(ethoxyacetyl)-
8.85 (d, J = 1.9 Hz, 1H), 8.56 (s, 1H), 8.43
m/e 420


1,2,3,6-
(s, 1H), 7.87 (s, 1H), 7.50-7.40 (m, 4H),
(M + H) +


tetrahydropyridin-
7.38-7.32 (m, 2H), 7.10 (dd, J = 9.4, 2.0



4-yl]phenyl}-3-
Hz, 1H), 6.09-6.04 (m, 1H), 4.13 (s,



imidazo[1,2-
2H), 4.13-4.08 (m, 2H), 3.66 (t, J = 5.7



a]pyridin-6-ylurea
Hz, 2H), 3.51 (q, J = 6.9 Hz, 2H), 2.50-




2.45 (m, 2H),1.14 (t, J = 6.9 Hz, 3H)


32
1-imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-6-yl-3-
8.96 (d, J = 1.9 Hz, 1H), 8.83 (s, 1H), 8.70
m/e 450


(4-{1-[(2-
(s, 1H), 7.96 (s, 1H), 7.55-7.42 (m, 4H),
(M + H) +


methoxyethoxy)
7.42-7.34 (m, 2H), 7.08 (dd, J = 9.6, 2.0



acetyl]-1,2,3,6-
Hz, 1H), 6.15-6.05 (m, 1H), 4.24-4.17



tetrahydropyridin-
(m, 2H), 4.12-4.05 (m, 2H), 3.70-3.54



4-yl}phenyl)urea
(m, 4H), 3.51-3.43 (m, 2H), 3.25 (s,




3H), 2.57-2.41 (m, 2H)


33
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 8.89-8.84 (m, 1H),
m/e 432


{4-[1-
8.59 (s, 1H), 8.47 (s, 1H), 7.86 (s, 1H),
(M + H) +


(tetrahydrofuran-
7.51-7.40 (m, 4H), 7.39-7.31 (m, 2H),



2-ylcarbonyl)-
7.12-7.08 (m, 1H), 6.10-6.04 (m, 1H),



1,2,3,6-
4.71-4.64 (m, 1H), 4.15 (m, 2H), 3.84-



tetrahydropyridin-
3.68 (m, 4H), 2.54-2.44 (m, 2H), 2.15-



4-yl]phenyl}urea
1.96 (m, 2H), 1.92-1.81 (m, 2H)


34
1-imidazo[1,2-
1 H NMR (300 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-yl-3-
8.93 (dd, J = 2.0, 1.0 Hz, 1H), 7.82 (s,
m/e 446


{4-[1-(tetrahydro-
1H), 7.56-7.47 (m, 2H), 7.47-7.35 (m,
(M + H) +


2H-pyran-4-
4H), 7.22-7.14 (m, 1H), 6.13-6.07 (m,



ylcarbonyl)-
1H), 4.32-4.16 (m, 2H), 4.03-3.92 (m,



1,2,3,6-
2H), 3.86-3.77 (m, 2H), 3.61-3.46 (m,



tetrahydropyridin-
2H), 3.12-2.92 (m, 1H), 2.66-2.49 (m,



4-yl]phenyl}urea
2H), 1.92-1.71 (m, 2H), 1.72-1.59 (m,




2H)


35
1-{4-[1-(1,4-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


dioxan-2-
Temp = 90° C.) δ ppm 8.86 (d, J = 1.2 Hz,
m/e 448


ylcarbonyl)-
1H), 8.61 (bs, 1H), 8.49 (bs, 1H), 7.87 (s,
(M + H) +


1,2,3,6-
1H), 7.52-7.40 (m, 4H), 7.38-7.32 (m,



tetrahydropyridin-
2H), 7.11 (dd, J = 9.6, 2.0 Hz, 1H), 6.10-



4-yl]phenyl}-3-
6.04 (m, 1H), 4.37 (dd, J = 9.2, 2.9 Hz,



imidazo[1,2-
1H), 4.15 (m, 2H), 3.81-3.63 (m, 7H),



a]pyridin-6-ylurea
3.58-3.45 (m, 1H), 2.56-2.47 (m, 2H)


36
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 8.91-8.87 (m 1H),
m/e 459


(4-{1-[(1-
8.68 (s, 1H), 8.56 (s, 1H), 7.90 (s, 1H),
(M + H) +


methylpiperidin-4-
7.53-7.44 (m, 4H), 7.41-7.35 (m, 2H),



yl)carbonyl]-
7.14 (dd, J = 9.6, 2.1 Hz, 1H), 6.14-6.08



1,2,3,6-
(m, 1H), 4.19-4.13 (m, 2H), 3.72 (t, J =



tetrahydropyridin-
5.7 Hz, 2H), 3.17 (m, 1H), 2.85-2.77 (m,



4-yl}phenyl)urea
2H), 2.64-2.48 (m, 2H), 2.20 (s, 3H),




2.06-1.94 (m, 2H), 1.76-1.60 (m, 4H)


37
1-(4-{1-[(1,1-
1 H NMR (300 MHz, DMSO-d 6 ) δ 8.98-
(ESI(+))


dioxidotetrahydro-
8.94 (m, 1H), 8.83 (bs, 1H), 8.70 (s, 1H),
m/e 494


2H-thiopyran-4-
7.97-7.94 (m, 1H), 7.55-7.35 (m, 6H),
(M + H) +


yl)carbonyl]-
7.09 (dd, J = 9.6, 2.0 Hz, 1H), 6.15-6.09



1,2,3,6-
(m, 1H), 4.27-4.20 (m, 1H), 4.13-4.06



tetrahydropyridin-
(m, 1H), 3.79-3.62 (m, 2H), 3.28-3.02



4-yl}phenyl)-3-
(m, 5H), 2.40-2.60 (m, 2H), 2.08-1.94



imidazo[1,2-
(m, 4H)



a]pyridin-6-ylurea



38
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 8.88-8.83 (m, 1H),
m/e 404


{4-[1-(2-
8.59 (bs, 1H), 8.47 (bs, 1H), 7.87 (s, 1H),
(M + H) +


methylpropanoyl)-
7.50-7.41 (m, 4H), 7.39-7.33 (m, 2H),



1,2,3,6-
7.11 (dd, J = 9.5, 2.0 Hz, 1H), 6.12-6.06



tetrahydropyridin-
(m, 1H), 4.17-4.11 (m, 2H), 3.69 (t, J =



4-yl]phenyl}urea
5.7 Hz, 2H), 2.95-2.86 (m, 1H), 2.50 (m,




2H), 1.05 (d, J = 6.7 Hz, 6H)










































































































Example 51
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
Example 51A
4-(1-isobutyl-1H-pyrazol-4-yl)aniline
A suspension of 4-bromoaniline (406 mg, 2.362 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (650 mg, 2.60 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/water/methanol (12 ml) in a microwave vial was subjected to three vacuum/nitrogen purge cycles. The vial was sealed and heated in an oil bath at 85° C. overnight. The mixture was dissolved in a mixture of ethyl acetate (45 ml) and water (20 ml), and the separated aqueous layer was extracted with ethyl acetate (20 ml). The combined organic layers were washed with brine (20 ml), dried with magnesium sulfate, filtered and concentrated. Normal phase chromatography provided the title compound.
Example 51B
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 1C, substituting 4-(1-isobutyl-1H-pyrazol-4-yl)aniline for 4-amino-N-isopentylbenzamide. 1 H NMR (400 MHz, CDCl 3 ) δ 9.18 (s, 2H), 8.49 (s, 1H), 7.73 (s, 1H), 7.64 (d, J=10.3 Hz, 2H), 7.56 (s, 1H), 7.42-7.31 (m, 4H), 7.36 (d, J=9.5 Hz, 1H), 6.62 (dd, J=9.6, 1.7 Hz, 1H), 3.92 (d, J=7.3 Hz, 2H), 2.23 (hept, J=6.8 Hz, 1H), 0.93 (d, J=6.7 Hz, 6H). MS (ESI)(+)) m/e 375 (M+H) + .
Example 52
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
Example 52A
methyl 4-(2-cyclopentylacetamido)benzoate
A solution of methyl 4-aminobenzoate (0.25 g, 1.654 mmol) in tetrahydrofuran (8.27 ml) was treated with diisopropylethylamine (0.433 ml, 2.481 mmol) and 2-cyclopentylacetyl chloride (0.279 g, 1.902 mmol) and the reaction mixture was stirred at ambient temperature for 2 hours. Concentration and normal phase chromatography provided the title compound.
Example 52B
4-(2-cyclopentylacetamido)benzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-(2-cyclopentylacetamido)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 52C
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.08 (s, 1H), 8.93 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.96 (s, 1H), 7.87-7.81 (m, 2H), 7.70-7.64 (m, 2H), 7.57-7.50 (m, 2H), 7.24 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.36-2.30 (m, 2H), 2.29-2.15 (m, 1H), 1.81-1.65 (m, 2H), 1.67-1.38 (m, 4H), 1.39-0.95 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 53
2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide
Example 53A
2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-A]pyridin-6-amine (0.768 g, 5.77 mmol) for 3-methylbutan-1-amine and 2-bromo-5-thiazolecarboxylic acid (1 g, 4.81 mmol) for 4-nitrobenzoic acid.
Example 53B
2-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide
To a solution of 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide (165 mg, 0.511 mmol) in acetonitrile (2553 μl) was added 4-cyanobenzylamine (67.5 mg, 0.511 mmol). The mixture was heated in a microwave (Biotage Initiator) at 180° C. for 30 minutes. The heating was repeated again after another equivalent of 4-cyanobenzylamine was added. The reaction mixture was purified by normal phase chromatography to provide the title compound.
Example 53C
2-[(4-cyanobenzyl)(3-methylbutanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and 2-(4-cyanobenzylamino)-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ 10.75 (s, 1H), 9.62 (s, 1H), 8.43 (d, J=1.6 Hz, 1H), 8.32 (s, 1H), 8.11 (s, 1H), 7.99-7.89 (m, 2H), 7.82 (dd, J=18.8, 8.3 Hz, 2H), 7.38 (d, J=8.3 Hz, 2H), 5.63 (s, 2H), 2.14 (dt, J=13.4, 6.7 Hz, 1H), 0.88 (d, J=6.7 Hz, 6H); (APCI(+)) m/e 459 (M+H) + .





TABLE 4



The following Examples were prepared essentially as described in Example 53,

substituting the appropriate amine in Example 53A, the appropriate amine in 53B and the

appropriate acid chloride in Example 53C. Some products were purified by flash

chromatography while others were purified by reverse-phase HPLC. Accordingly, some

Examples were isolated as trifluoroacetic acid salts.






Ex
Name
1 H NMR
MS








54
2-[(4-
1 H NMR (400 MHz, DMSO-d 6 ) δ 10.75
(APCI(+))


cyanobenzyl)(3-
(s, 1H), 9.61 (s, 1H), 8.42 (s, 1H), 8.33
m/e 461


methoxypropanoyl)
(s, 1H), 8.10 (s, 1H), 7.94 (s, 2H), 7.84
(M + H) +


amino]-N-
(d, J = 8.3 Hz, 3H), 7.40 (d, J = 8.3 Hz,



(imidazo[1,2-
2H), 5.64 (s, 2H), 3.64 (t, J = 6.0 Hz,



a]pyridin-6-yl)-
2H), 3.20 (s, 3H), 2.89 (t, J = 6.1 Hz,



1,3-thiazole-5-
2H).



carboxamide



55
2-[(4-
1 H NMR (400 MHz, CDCl 3 ) δ 8.57 (s,
(APCI(+))


cyanobenzyl)(3-
1H), 8.16 (d, J = 9.5 Hz, 1H), 7.96 (s,
m/e 473


methylbutanoyl)
1H), 7.86 (d, J = 1.8 Hz, 1H), 7.81 (d, J =
(M + H) +


amino]-N-
9.6 Hz, 1H), 7.75 (s, 1H), 7.63 (d, J =



(imidazo[1,2-
8.3 Hz, 2H), 7.24 (d, J = 8.3 Hz, 2H),



a]pyridin-6-
5.54 (s, 2H), 4.69 (d, J = 6.1 Hz, 2H),



ylmethyl)-1,3-
2.39 (d, J = 6.7 Hz, 2H), 2.30-2.24 (m,



thiazole-5-
1H), 0.94 (d, J = 6.6 Hz, 6H)



carboxamide



56
2-[(4-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


cyanobenzyl)(3-
8.78 (s, 1H), 8.20 (d, J = 2.1 Hz, 1H),
m/e 475


methoxypropanoyl)
8.02 (d, J = 2.1 Hz, 1H), 8.01 (s, 1H),
(M + H) +


amino]-N-
8.00-7.96 (m, 1H), 7.90 (d, J = 9.3 Hz,



(imidazo[1,2-
1H), 7.70 (d, J = 8.2 Hz, 2H), 7.38 (d, J =



a]pyridin-6-
8.2 Hz, 2H), 5.65 (s, 2H), 4.66 (s, 2H),



ylmethyl)-1,3-
3.73 (t, J = 5.9 Hz, 2H), 2.87 (t, J = 5.9



thiazole-5-
Hz, 2H)



carboxamide



57
2-[(4-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


cyanobenzyl)(3-
9.22 (td, J = 6.4, 1.2 Hz, 1H), 8.75 (d, J =
m/e 475


methoxypropanoyl)
7.0 Hz, 1H), 8.18 (d, J = 2.0 Hz, 1H),
(M + H) +


amino]-N-
8.08-7.95 (m, 2H), 7.80 (s, 1H), 7.77-



(imidazo[1,2-
7.66 (m, 2H), 7.47 (dd, J = 7.1, 1.1 Hz,



a]pyridin-7-
1H), 7.39 (d, J = 8.2 Hz, 2H), 5.66 (s,



ylmethyl)-1,3-
2H), 4.73 (d, J = 4.5 Hz, 2H), 3.74 (t, J =



thiazole-5-
5.9 Hz, 2H), 2.88 (t, J = 5.8 Hz, 2H)



carboxamide



61
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H),
m/e 430


ylmethyl)-2-[(3-
8.08 (s, 1H), 8.05-7.96 (m, 2H), 7.90
(M + H) +


methoxypropanoyl)
(d, J = 9.3 Hz, 1H), 4.67 (d, J = 3.8 Hz,



(3-
2H), 4.27 (dd, J = 9.3, 7.0 Hz, 2H), 3.79



methylbutyl)
(t, J = 5.9 Hz, 2H), 3.36 (s, 3H), 2.98 (t,



amino]-1,3-thiazole-
J = 5.9 Hz, 2H), 1.80-1.67 (m, 1H),



5-carboxamide
1.67-1.57 (m, 2H), 1.01 (d, J = 6.5 Hz,




6H)


121
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) δ 9.11
(APCI(+))


a]pyridin-7-
(t, J = 5.9 Hz, 1H), 8.50 (d, J = 7.0 Hz,
m/e 444


ylmethyl)-2-[(3-
1H), 8.17 (s, 1H), 7.90 (s, 1H), 7.53 (s,
(M + H) +


methoxypropanoyl)
1H), 7.41 (s, 1H), 6.85 (dd, J = 7.1, 1.5



(tetrahydrofuran-
Hz, 1H), 4.48 (d, J = 5.8 Hz, 2H), 4.39



2-
(d, J = 12.5 Hz, 1H), 4.25-4.08 (m,



ylmethyl)amino]-
2H), 3.78 (dd, J = 14.8, 6.8 Hz, 1H),



1,3-thiazole-5-
3.66 (t, J = 6.4 Hz, 2H), 3.65-3.55 (m,



carboxamide
1H), 3.26 (s, 3H), 3.06 (ddd, J = 17.2,




13.9, 6.4 Hz, 2H), 1.99 (dd, J = 12.7, 7.4




Hz, 1H), 1.94-1.86 (m, 1H), 1.86-




1.74 (m, 1H), 1.66-1.53 (m, 1H)


123
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O)
(ESI(+))


a]pyridin-6-
ppm 8.76 (s, 1 H) 8.24 (d, J = 2.14 Hz, 1
m/e 496


ylmethyl)-2-{[(2-
H) 8.10 (s, 1 H) 8.02 (d, J = 2.14 Hz, 1
(M + H) +


methyl-1,3-
H) 7.89 (d, J = 1.22 Hz, 2 H) 7.45 (s, 1



thiazol-5-
H) 4.57 (s, 2 H) 4.50 (d, J = 12.21 Hz, 1



yl)acetyl](tetrahy-
H) 4.42 (d, J = 5.80 Hz, 1 H) 4.19-4.31



drofuran-2-
(m, 2 H) 3.78-3.85 (m, 1 H) 3.63-3.69



ylmethyl)amino}-
(m, 1 H) 3.28-3.29 (m, 2 H) 2.62 (s, 3



1,3-thiazole-5-
H) 2.01 (s, 1 H) 1.81-1.95 (m, 2 H)



carboxamide
1.60-1.68 (m, 1 H)


124
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O)
(ESI(+))


a]pyridin-6-
ppm 8.78 (s, 1 H) 8.26 (d, J = 1.83 Hz, 1
m/e 496


ylmethyl)-2-{[(2-
H) 8.10 (s, 1 H) 8.05 (d, J = 2.14 Hz, 1
(M + H) +


methyl-1,3-
H) 7.90-7.96 (m, 2 H) 7.24 (s, 1 H)



thiazol-4-
4.58 (s, 2 H) 4.47 (dd, 1 H) 4.18-4.37



yl)acetyl](tetrahy-
(m, 4 H) 3.79-3.86 (m, 1 H) 3.62-3.69



drofuran-2-
(m, 1 H) 2.62 (s, 3 H) 1.97-2.06 (m, 1



ylmethyl)amino}-
H) 1.80-1.94 (m, 2 H) 1.56-1.69 (m, 1



1,3-thiazole-5-
H)



carboxamide



125
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O)
(ESI(+))


a]pyridin-6-
ppm 8.70 (s, 1 H) 8.17 (d, J = 1.83 Hz, 1
m/e 480


ylmethyl)-2-{[(3-
H) 8.10 (s, 1 H) 7.92 (d, J = 1.83 Hz, 1
(M + H) +


methyl-1,2-
H) 7.79-7.84 (m, 1 H) 7.73-7.85 (m, 1



oxazol-5-
H) 6.27 (s, 1 H) 4.55 (s, 2 H) 4.35-4.52



yl)acetyl](tetrahy-
(m, 3 H) 4.19-4.27 (m, 2 H) 3.77-3.85



drofuran-2-
(m, 1 H) 3.62-3.69 (m, 1 H) 2.23 (s, 3



ylmethyl)amino}-
H) 2.01 (d, J = 2.75 Hz, 1 H) 1.80-1.95



1,3-thiazole-5-
(m, 2 H) 1.56-1.67 (m, 1 H)



carboxamide



126
2-{[3-(3-chloro-

(ESI(+))


1,2-oxazol-5-

m/e 515


yl)propanoyl]

(M + H) +


(tetrahydrofuran-2-




ylmethyl)amino}-




N-(imidazo[1,2-




a]pyridin-6-




ylmethyl)-1,3-




thiazole-5-




carboxamide



127
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 510


ylmethyl)-2-{[3-

(M + H) +


(3-methoxy-1,2-




oxazol-5-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



128
2-{[(3,5-dimethyl-

(ESI(+))


1,2-oxazol-4-

m/e 495


yl)acetyl](tetra-

(M + H) +


hydrofuran-2-




ylmethyl)amino}-




N-(imidazo[1,2-




a]pyridin-6-




ylmethyl)-1,3-




thiazole-5-




carboxamide



129
2-{[3-(3,5-

(ESI(+))


dimethyl-1,2-

m/e 509


oxazol-4-

(M + H) +


yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




N-(imidazo[1,2-




a]pyridin-6-




ylmethyl)-1,3-




thiazole-5-




carboxamide



130
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 494


ylmethyl)-2-{[3-

(M + H) +


(1-methyl-1H-




pyrazol-4-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



131
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 511


ylmethyl)-2-{[3-

(M + H) +


(4-methyl-1,3-




thiazol-5-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



132
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 468


ylmethyl)-2-

(M + H) +


[(tetrahydrofuran-




2-ylmethyl)(1H-




tetrazol-5-




ylacetyl)amino]-




1,3-thiazole-5-




carboxamide



133
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 481


ylmethyl)-2-{[3-

(M + H) +


(1,2-oxazol-5-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



134
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 467


ylmethyl)-2-[(1,2-

(M + H) +


oxazol-3-




ylacetyl)(tetra-




hydrofuran-2-




ylmethyl)amino]-




1,3-thiazole-5-




carboxamide



135
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 481


ylmethyl)-2-{[3-

(M + H) +


(1,2-oxazol-4-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



136
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 497


ylmethyl)-2-

(M + H) +


{(tetrahydrofuran-




2-ylmethyl)[3-




(1,3-thiazol-2-




yl)propanoyl]




amino}-1,3-thiazole-




5-carboxamide



139
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H),
m/e 444


ylmethyl)-2-[(3-
8.08 (s, 1H), 8.03 (d, J = 2.2 Hz, 1H),
(M + H) +


methoxypropanoyl)
7.98 (d, J = 1.4 Hz, 1H), 7.91 (d, J = 9.3



(tetrahydrofuran-
Hz, 1H), 4.66 (s, 2H), 4.31 (qd, J = 14.8,



3-
7.7 Hz, 2H), 3.96 (td, J = 8.2, 5.7 Hz,



ylmethyl)amino]-
1H), 3.87-3.71 (m, 3H), 3.65 (qd, J =



1,3-thiazole-5-
8.9, 5.6 Hz, 2H), 3.36 (s, 3H), 3.02 (dd,



carboxamide
J = 10.4, 5.6 Hz, 2H), 2.94-2.81 (m,




1H), 2.05 (dtd, J = 13.5, 8.0, 5.7 Hz,




1H), 1.75 (ddd, J = 12.6, 7.9, 6.5 Hz,




1H)


140
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 1.9 Hz, 1H),
m/e 470


ylmethyl)-2-
8.09 (s, 1H), 8.03 (d, J = 2.0 Hz, 1H),
(M + H) +


[(tetrahydrofuran-
8.00 (d, J = 9.3 Hz, 1H), 7.91 (d, J = 9.2



3-
Hz, 1H), 4.66 (s, 2H), 4.40 (dd, J = 14.8,



ylmethyl)(tetra-
7.0 Hz, 1H), 4.28 (dd, J = 14.7, 8.5 Hz,



hydro-2H-pyran-4-
1H), 4.06-3.94 (m, 3H), 3.77 (dd, J =



ylcarbonyl)amino]-
15.0, 8.1 Hz, 1H), 3.68 (dd, J = 8.9, 6.3



1,3-thiazole-5-
Hz, 1H), 3.60 (dd, J = 8.9, 4.7 Hz, 1H),



carboxamide
3.55 (t, J = 11.7 Hz, 2H), 3.24 (tt, J =




11.1, 3.7 Hz, 1H), 2.85 (dt, J = 12.1, 3.5




Hz, 1H), 2.11-2.01 (m, 1H), 1.93 (ddd,




J = 16.1, 12.7, 4.3 Hz, 1H), 1.89-1.82




(m, 1H), 1.75 (dt, J = 13.0, 9.9 Hz, 3H)


142
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H),
m/e 458


ylmethyl)-2-[(3-
8.08 (s, 1H), 8.03 (d, J = 2.1 Hz, 1H),
(M + H) +


methoxypropanoyl)
8.00 (dd, J = 9.4, 1.4 Hz, 1H), 7.91 (d, J =



(tetrahydro-2H-
9.4 Hz, 1H), 4.66 (s, 2H), 4.23 (d, J =



pyran-4-
7.3 Hz, 2H), 4.00-3.85 (m, 2H), 3.79



ylmethyl)amino]-
(t, J = 5.9 Hz, 2H), 3.36 (s, 3H), 3.02 (t,



1,3-thiazole-5-
J = 5.9 Hz, 2H), 2.26-2.13 (m, 1H),



carboxamide
1.58-1.50 (m, 2H), 1.49-1.36 (m, 2H)


143
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 2.1 Hz, 1H),
m/e 470


ylmethyl)-2-
8.09 (s, 1H), 8.03 (d, J = 2.0 Hz, 1H),
(M + H) +


[(tetrahydrofuran-
8.00 (d, J = 9.3 Hz, 1H), 7.91 (d, J = 9.3



3-
Hz, 1H), 4.67 (s, 2H), 4.32-4.23 (m,



ylcarbonyl)(tetra-
2H), 4.08 (t, J = 8.1 Hz, 1H), 3.94 (qd, J =



hydro-2H-pyran-4-
9.9, 3.8 Hz, 4H), 3.87 (dd, J = 14.8,



ylmethyl)amino]-
7.3 Hz, 1H), 3.83-3.74 (m, 1H), 3.35



1,3-thiazole-5-
(dd, J = 11.7, 1.9 Hz, 2H), 2.31 (dt, J =



carboxamide
15.4, 7.1 Hz, 1H), 2.18 (td, J = 12.9, 6.6




Hz, 2H), 1.53 (t, J = 10.9 Hz, 2H), 1.50-




1.41 (m, 2H)


144
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 2.0 Hz, 1H),
m/e 484


ylmethyl)-2-
8.09 (s, 1H), 8.03 (d, J = 2.1 Hz, 1H),
(M + H) +


[(tetrahydro-2H-
8.00 (dd, J = 9.3, 1.4 Hz, 1H), 7.91 (d, J =



pyran-4-
9.3 Hz, 1H), 4.66 (s, 2H), 4.27 (d, J =



ylcarbonyl)(tetra-
7.3 Hz, 2H), 4.03-3.97 (m, 2H), 3.93



hydro-2H-pyran-4-
(dd, J = 11.4, 2.7 Hz, 2H), 3.62-3.52



ylmethyl)amino]-
(m, 2H), 3.35 (dd, J = 11.6, 2.2 Hz, 2H),



1,3-thiazole-5-
3.26 (dd, J = 9.3, 5.6 Hz, 1H), 2.21-



carboxamide
2.10 (m, 1H), 1.89 (ddd, J = 16.0, 12.6,




4.4 Hz, 2H), 1.76 (dd, J = 13.0, 1.5 Hz,




2H), 1.54 (dt, J = 7.1, 3.0 Hz, 2H), 1.51-




1.42 (m, 2H)


145
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.78 (s, 1H), 8.21 (s, 1H), 8.07 (s, 1H),
m/e 444


ylmethyl)-2-{(3-
8.02 (s, 1H), 8.00 (d, J = 9.4 Hz, 1H),
(M + H) +


methoxypropanoyl)
7.91 (d, J = 9.4 Hz, 1H), 4.66 (s, 2H),



[(2R)-
4.52 (d, J = 14.9 Hz, 1H), 4.29 (d, J =



tetrahydrofuran-2-
6.8 Hz, 1H), 4.17 (dd, J = 14.9, 8.9 Hz,



ylmethyl]amino}-
1H), 3.88 (dd, J = 14.5, 7.2 Hz, 1H),



1,3-thiazole-5-
3.76 (dd, J = 14.0, 7.9 Hz, 2H), 3.74-



carboxamide
3.69 (m, 1H), 3.36 (s, 3H), 3.13 (q, J =




6.1 Hz, 2H), 2.10 (td, J = 12.4, 7.4 Hz,




1H), 2.04-1.94 (m, 1H), 1.94-1.85




(m, 1H), 1.67 (dq, J = 15.3, 7.8 Hz, 1H)


146
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (s, 1H), 8.08 (s, 1H),
m/e 456


ylmethyl)-2-
8.02 (d, J = 1.8 Hz, 1H), 8.00 (d, J = 9.4
(M + H) +


{(tetrahydrofuran-
Hz, 1H), 7.91 (d, J = 9.3 Hz, 1H), 4.66



3-
(s, 2H), 4.61 (t, J = 13.7 Hz, 1H), 4.30-



ylcarbonyl)[(2R)-
4.17 (m, 2H), 4.06 (ddd, J = 15.8, 14.9,



tetrahydrofuran-2-
7.9 Hz, 1H), 3.99-3.91 (m, 2H), 3.90-



ylmethyl]amino}-
3.79 (m, 3H), 3.76-3.68 (m, 1H), 2.32



1,3-thiazole-5-
(qd, J = 12.8, 6.7 Hz, 1H), 2.25-2.04



carboxamide
(m, 2H), 2.03-1.86 (m, 2H), 1.72-




1.61 (m, 1H)


147
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 2.1 Hz, 1H),
m/e 470


ylmethyl)-2-
8.07 (s, 1H), 8.02 (d, J = 2.1 Hz, 1H),
(M + H) +


{[(2R)-
8.00 (dd, J = 9.3, 1.2 Hz, 1H), 7.91 (d, J =



tetrahydrofuran-2-
9.3 Hz, 1H), 4.66 (s, 2H), 4.61 (d, J =



ylmethyl](tetra-
12.8 Hz, 1H), 4.29-4.19 (m, 2H), 4.06-



hydro-2H-pyran-4-
3.96 (m, 2H), 3.85 (dd, J = 14.9, 6.9



ylcarbonyl)amino}-
Hz, 1H), 3.73 (dd, J = 13.9, 7.7 Hz, 1H),



1,3-thiazole-5-
3.57-3.47 (m, 2H), 3.43 (ddd, J = 14.8,



carboxamide
8.4, 3.9 Hz, 1H), 2.11 (dt, J = 12.1, 5.4




Hz, 1H), 2.05-1.87 (m, 3H), 1.83-




1.73 (m, 3H), 1.73-1.64 (m, 1H)


148
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.78 (s, 1H), 8.21 (d, J = 1.8 Hz, 1H),
m/e 444


ylmethyl)-2-{(3-
8.06 (s, 1H), 8.02 (d, J = 2.2 Hz, 1H),
(M + H) +


methoxypropanoyl)
8.00 (dd, J = 9.4, 1.5 Hz, 1H), 7.90 (d, J =



[(2S)-
9.3 Hz, 1H), 4.66 (s, 2H), 4.52 (dd, J =



tetrahydrofuran-2-
14.9, 2.5 Hz, 1H), 4.32-4.25 (m,



ylmethyl]amino}-
1H), 4.17 (dd, J = 14.8, 8.9 Hz, 1H),



1,3-thiazole-5-
3.92-3.83 (m, 1H), 3.81-3.74 (m,



carboxamide
2H), 3.71 (td, J = 7.7, 6.3 Hz, 1H), 3.36




(s, 3H), 3.21-3.05 (m, 2H), 2.15-2.05




(m, 1H), 2.04-1.95 (m, 1H), 1.91 (ddt,




J = 7.5, 5.0, 1.9 Hz, 1H), 1.73-1.60 (m,




1H)


149
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 2.2 Hz, 1H),
m/e 456


ylmethyl)-2-
8.08 (d, J = 0.7 Hz, 1H), 8.02 (d, J = 2.1
(M + H) +


{(tetrahydrofuran-
Hz, 1H), 8.00 (dd, J = 9.3, 1.3 Hz, 1H),



3-
7.91 (d, J = 9.3 Hz, 1H), 4.66 (s, 2H),



ylcarbonyl)[(2S)-
4.61 (t, J = 13.2 Hz, 1H), 4.31-4.17



tetrahydrofuran-2-
(m, 2H), 4.06 (ddd, J = 14.8, 14.3, 7.3



ylmethyl]amino}-
Hz, 1H), 4.00-3.92 (m, 2H), 3.90-



1,3-thiazole-5-
3.79 (m, 3H), 3.71 (ddd, J = 10.8, 8.3,



carboxamide
3.1 Hz, 1H), 2.39-2.27 (m, 1H), 2.25-




2.04 (m, 2H), 2.03-1.87 (m, 2H), 1.73-




1.60 (m, 1H)


150
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
8.79 (s, 1H), 8.21 (d, J = 1.9 Hz, 1H),
m/e 470


ylmethyl)-2-
8.07 (d, J = 3.1 Hz, 1H), 8.02 (d, J = 2.2
(M + H) +


{[(2S)-
Hz, 1H), 8.00 (dd, J = 9.4, 1.5 Hz, 1H),



tetrahydrofuran-2-
7.91 (d, J = 9.3 Hz, 1H), 4.66 (s, 2H),



ylmethyl](tetra-
4.61 (d, J = 12.7 Hz, 1H), 4.31-4.19



hydro-2H-pyran-4-
(m, 2H), 4.07-3.95 (m, 2H), 3.89-



ylcarbonyl)amino}-
3.81 (m, 1H), 3.73 (td, J = 7.8, 6.1 Hz,



1,3-thiazole-5-
1H), 3.58-3.47 (m, 2H), 3.47-3.39



carboxamide
(m, 1H), 2.16-2.05 (m, 1H), 2.05-




1.86 (m, 3H), 1.77 (ddd, J = 14.6, 6.0,




2.5 Hz, 3H), 1.73-1.65 (m, 1H)


183
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 480


ylmethyl)-2-{[(1-

(M + H) +


methyl-1H-




pyrazol-4-




yl)acetyl](tetra-




hydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



184
2-{[(1,3-dimethyl-

(ESI(+))


1H-pyrazol-4-

m/e 494


yl)acetyl](tetra-

(M + H) +


hydrofuran-2-




ylmethyl)amino}-




N-(imidazo[1,2-




a]pyridin-6-




ylmethyl)-1,3-




thiazole-5-




carboxamide



189
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 493


ylmethyl)-2-{[3-

(M + H) +


(1-methyl-1H-




pyrrol-2-




yl)propanoyl]




(tetrahydrofuran-2-




ylmethyl)amino}-




1,3-thiazole-5-




carboxamide



190
2-{[(1,5-dimethyl-

(ESI(+))


1H-pyrazol-3-

m/e 494


yl)acetyl](tetra-

(M + H) +


hydrofuran-2-




ylmethyl)amino}-




N-(imidazo[1,2-




a]pyridin-6-




ylmethyl)-1,3-




thiazole-5-




carboxamide



191
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 483


ylmethyl)-2-

(M + H) +


[(tetrahydrofuran-




2-ylmethyl)(1,3-




thiazol-4-




ylacetyl)amino]-




1,3-thiazole-5-




carboxamide



192
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.73 (d, J = 7.0 Hz, 1H), 8.64 (d, J = 1.5
m/e 467


ylmethyl)-2-{[1,2-
Hz, 1H), 8.16 (d, J = 2.1 Hz, 1H), 8.12
(M + H) +


oxazol-3-
(s, 1H), 7.98 (d, J = 2.2 Hz, 1H), 7.80 (s,



ylacetyl)[(2R)-
1H), 7.46 (dd, J = 7.0, 1.4 Hz, 1H), 6.52



tetrahydrofuran-2-
(d, J = 1.6 Hz, 1H), 4.72 (s, 2H), 4.65



ylmethyl]amino}-
(dd, J = 14.9, 1.9 Hz, 1H), 4.42 (d, J =



1,3-thiazole-5-
1.4 Hz, 2H), 4.32 (dd, J = 11.6, 4.4 Hz,



carboxamide
1H), 4.23 (dd, J = 14.8, 9.0 Hz, 1H),




3.94 (dd, J = 14.9, 6.8 Hz, 1H), 3.76




(dd, J = 14.2, 7.7 Hz, 1H), 2.21-2.07




(m, 1H), 2.08-1.87 (m, 2H), 1.69 (ddd,




J = 15.8, 12.3, 7.6 Hz, 1H)


193
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.74 (d, J = 7.0 Hz, 1H), 8.17 (d, J = 1.9
m/e 481


ylmethyl)-2-{[(5-
Hz, 1H), 8.11 (s, 1H), 7.99 (d, J = 2.1
(M + H) +


methyl-1,2-
Hz, 1H), 7.79 (s, 1H), 7.47 (d, J = 6.8



oxazol-3-
Hz, 1H), 6.16 (s, 1H), 4.72 (s, 2H), 4.63



yl)acetyl][(2R)-
(d, J = 12.8 Hz, 1H), 4.36-4.27 (m,



tetrahydrofuran-2-
3H), 4.21 (dd, J = 14.6, 9.4 Hz, 1H),



ylmethyl]amino}-
3.94 (dd, J = 15.1, 6.8 Hz, 1H), 3.75



1,3-thiazole-5-
(dd, J = 14.3, 7.5 Hz, 1H), 2.43 (s, 3H),



carboxamide
2.13 (d, J = 8.1 Hz, 1H), 2.05-1.89 (m,




2H), 1.75-1.62 (m, 1H)


194
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.74 (d, J = 7.0 Hz, 1H), 8.27 (d, J = 1.6
m/e 481


ylmethyl)-2-{[3-
Hz, 1H), 8.17 (d, J = 2.1 Hz, 1H), 8.10
(M + H) +


(1,2-oxazol-5-
(s, 1H), 7.99 (d, J = 2.1 Hz, 1H), 7.79 (s,



yl)propanoyl][(2R)-
1H), 7.47 (d, J = 6.8 Hz, 1H), 6.23 (s,



tetrahydrofuran-
1H), 4.72 (s, 2H), 4.55 (d, J = 12.6 Hz,



2-
1H), 4.35-4.23 (m, 1H), 4.15 (dd, J =



ylmethyl]amino}-
14.8, 9.0 Hz, 1H), 3.87 (dd, J = 14.8, 6.9



1,3-thiazole-5-
Hz, 1H), 3.72 (dd, J = 14.0, 7.8 Hz, 1H),



carboxamide
3.46 (dd, J = 12.2, 6.1 Hz, 1H), 3.28-




3.18 (m, 3H), 2.10 (dd, J = 12.6, 7.2 Hz,




1H), 1.94 (dd, J = 15.7, 8.4 Hz, 2H),




1.74-1.60 (m, 1H)


195
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.71 (d, J = 7.0 Hz, 1H), 8.51 (s, 1H),
m/e 481


ylmethyl)-2-{[3-
8.36 (s, 1H), 8.11 (d, J = 17.0 Hz, 2H),
(M + H) +


(1,2-oxazol-4-
7.94 (d, J = 2.0 Hz, 1H), 7.76 (s, 1H),



yl)propanoyl][(2R)-
7.42 (d, J = 6.8 Hz, 1H), 4.71 (s, 2H),



tetrahydrofuran-
4.53 (d, J = 12.5 Hz, 1H), 4.27 (t, J =



2-
6.7 Hz, 1H), 4.14 (dd, J = 14.9, 9.1 Hz,



ylmethyl]amino}-
1H), 3.83 (dd, J = 14.9, 6.8 Hz, 1H),



1,3-thiazole-5-
3.69 (dd, J = 13.8, 7.5 Hz, 1H), 3.26 (d,



carboxamide
J = 7.1 Hz, 1H), 3.09 (dd, J = 17.6, 6.4




Hz, 1H), 2.91 (dd, J = 12.3, 6.4 Hz, 2H),




2.10 (dt, J = 12.3, 5.9 Hz, 1H), 2.03-




1.84 (m, 2H), 1.74-1.58 (m, 1H)


196
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
9.00 (s, 1H), 8.74 (d, J = 7.0 Hz, 1H),
m/e 483


ylmethyl)-2-
8.17 (d, J = 1.9 Hz, 1H), 8.11 (s, 1H),
(M + H) +


{[(2R)-
7.98 (d, J = 2.2 Hz, 1H), 7.79 (s, 1H),



tetrahydrofuran-2-
7.51 (s, 1H), 7.47 (d, J = 7.0 Hz, 1H),



ylmethyl](1,3-
4.72 (s, 2H), 4.63 (d, J = 12.8 Hz, 1H),



thiazol-4-
4.49 (q, J = 16.9 Hz, 2H), 4.38-4.25



ylacetyl)amino}-
(m, 2H), 3.96 (dd, J = 14.9, 6.7 Hz, 1H),



1,3-thiazole-5-
3.76 (dd, J = 14.2, 7.6 Hz, 1H), 2.19-



carboxamide
2.08 (m, 1H), 2.06-1.98 (m, 1H), 1.98-




1.89 (m, 1H), 1.70 (td, J = 15.6, 7.6




Hz, 1H)


197
2-{[(1,5-dimethyl-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


1H-pyrazol-3-
8.74 (d, J = 7.0 Hz, 1H), 8.17 (d, J = 2.1
m/e 494


yl)acetyl][(2R)-
Hz, 1H), 8.10 (s, 1H), 7.99 (d, J = 2.1
(M + H) +


tetrahydrofuran-2-
Hz, 1H), 7.79 (s, 1H), 7.47 (d, J = 7.0



ylmethyl]amino}-
Hz, 1H), 6.01 (s, 1H), 4.72 (s, 2H), 4.55



N-(imidazo[1,2-
(d, J = 12.9 Hz, 1H), 4.30 (t, J = 7.9 Hz,



a]pyridin-7-
1H), 4.27-4.18 (m, 2H), 4.10 (t, J =



ylmethyl)-1,3-
15.1 Hz, 1H), 3.94 (dd, J = 14.8, 6.8 Hz,



thiazole-5-
1H), 3.82-3.68 (m, 4H), 2.27 (s, 3H),



carboxamide
2.20-2.06 (m, 1H), 2.00 (dd, J = 13.5,




5.8 Hz, 1H), 1.97-1.87 (m, 1H), 1.76-




1.58 (m, 1H)


198
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.75 (d, J = 7.0 Hz, 1H), 8.17 (d, J = 2.1
m/e 494


ylmethyl)-2-{[3-
Hz, 1H), 8.09 (s, 1H), 7.99 (d, J = 2.1
(M + H) +


(1-methyl-1H-
Hz, 1H), 7.80 (s, 1H), 7.47 (d, J = 8.2



pyrazol-4-
Hz, 1H), 7.45 (s, 1H), 7.36 (s, 1H), 4.72



yl)propanoyl][(2R)-
(s, 2H), 4.50 (dd, J = 14.9, 2.3 Hz, 1H),



tetrahydrofuran-
4.27 (t, J = 6.9 Hz, 1H), 4.13 (dd, J =



2-
14.9, 9.0 Hz, 1H), 3.89-3.76 (m, 4H),



ylmethyl]amino}-
3.70 (dd, J = 14.1, 7.6 Hz, 1H), 3.21 (dt,



1,3-thiazole-5-
J = 17.0, 7.2 Hz, 1H), 3.05 (dt, J = 16.9,



carboxamide
6.9 Hz, 1H), 2.88 (t, J = 7.1 Hz, 2H),




2.09 (dt, J = 12.1, 7.6 Hz, 1H), 1.92




(ddd, J = 19.6, 13.4, 7.1 Hz, 2H), 1.65




(dt, J = 19.6, 7.6 Hz, 1H)


199
2-{[(3,5-dimethyl-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


1,2-oxazol-4-
8.74 (d, J = 7.0 Hz, 1H), 8.17 (d, J = 2.0
m/e 495


yl)acetyl][(2R)-
Hz, 1H), 8.11 (s, 1H), 7.99 (d, J = 2.2
(M + H) +


tetrahydrofuran-2-
Hz, 1H), 7.79 (s, 1H), 7.47 (d, J = 7.1



ylmethyl]amino}-
Hz, 1H), 4.72 (s, 2H), 4.68 (d, J = 13.1



N-(imidazo[1,2-
Hz, 1H), 4.39-4.19 (m, 3H), 4.03-



a]pyridin-7-
3.88 (m, 2H), 3.77 (dd, J = 13.8, 7.6 Hz,



ylmethyl)-1,3-
1H), 2.32 (s, 3H), 2.23-2.11 (m, 4H),



thiazole-5-
2.09-1.91 (m, 2H), 1.77-1.63 (m, 1H)



carboxamide



202
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
9.20 (s, 1H), 8.74 (d, J = 7.2 Hz, 1H),
m/e 480


ylmethyl)-2-{[(1-
8.17 (d, J = 2.0 Hz, 1H), 8.10 (s, 1H),
(M + H) +


methyl-1H-
7.99 (d, J = 2.1 Hz, 1H), 7.79 (s, 1H),



pyrazol-4-
7.57 (s, 1H), 7.47 (d, J = 5.9 Hz, 1H),



yl)acetyl][(2R)-
7.42 (s, 1H), 4.72 (s, 2H), 4.59 (d, J =



tetrahydrofuran-2-
13.1 Hz, 1H), 4.31 (t, J = 7.1 Hz, 1H),



ylmethyl]amino}-
4.22 (dd, J = 14.7, 9.1 Hz, 1H), 4.11 (s,



1,3-thiazole-5-
2H), 3.92 (dd, J = 14.9, 6.9 Hz, 1H),



carboxamide
3.87 (s, 3H), 3.76 (dd, J = 14.2, 7.7 Hz,




1H), 2.19-2.06 (m, 1H), 2.00 (d, J =




7.3 Hz, 1H), 1.94 (dd, J = 13.4, 6.2 Hz,




1H), 1.69 (dt, J = 15.5, 7.5 Hz, 1H)


203
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-
8.74 (d, J = 7.0 Hz, 1H), 8.17 (d, J = 2.0
m/e 493


ylmethyl)-2-{[3-
Hz, 1H), 8.10 (s, 1H), 7.99 (d, J = 2.1
(M + H) +


(1-methyl-1H-
Hz, 1H), 7.80 (s, 1H), 7.47 (d, J = 7.0



pyrrol-2-
Hz, 1H), 6.54 (d, J = 2.5 Hz, 1H), 5.91



yl)propanoyl][(2R)-
(t, J = 3.1 Hz, 1H), 5.83 (s, 1H), 4.72 (s,



tetrahydrofuran-
2H), 4.50 (dd, J = 14.9, 2.3 Hz, 1H),



2-
4.28 (t, J = 6.8 Hz, 1H), 4.12 (dd, J =



ylmethyl]amino}-
14.8, 8.9 Hz, 1H), 3.85 (dd, J = 14.9, 6.8



1,3-thiazole-5-
Hz, 1H), 3.77-3.65 (m, 1H), 3.58 (s,



carboxamide
3H), 3.25 (t, J = 8.4 Hz, 1H), 3.16-




3.02 (m, 1H), 2.96 (t, J = 7.4 Hz, 2H),




2.10 (dt, J = 12.0, 7.3 Hz, 1H), 2.04-




1.81 (m, 2H), 1.66 (dt, J = 15.7, 7.4 Hz,




1H)















































































































































































































































































































































































































































































































































Example 58
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminobutyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide. 1 H NMR (500 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 8.79-8.76 (m, 1H), 8.10 (bs, 1H), 7.81-7.78 (m, 1H), 7.45-7.37 (m, 2H), 7.02 (dd, J=9.5, 2.1 Hz, 1H), 6.04-5.96 (m, 1H), 3.93-3.85 (m, 2H), 3.14-3.06 (m, 2H), 2.75-2.63 (m, 2H), 1.67-1.57 (m, 2H), 1.50-1.19 (m, 16H), 1.07-0.91 (m, 2H); MS (ESI(+)) m/e 416 (M+H) + .
Example 59
4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)benzamide
The title compound was prepared as described in Example 1, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine in Example 1C. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.87 (s, 1H), 8.46-8.41 (m, 1H), 8.23-8.15 (m, 1H), 7.97-7.93 (m, 1H), 7.76-7.70 (m, 2H), 7.57-7.51 (m, 2H), 7.49-7.43 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.77 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 3.29-3.19 (m, 2H), 1.67-1.53 (m, 1H), 1.45-1.35 (m, 2H), 0.93-0.87 (m, 6H); MS (ESI(+)) m/e 380 (M+H) + .
Example 60
2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide
The title compound was prepared as described in Example 3, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine in Example 3A. 1 H NMR (400 MHz, DMSO-d 6 , Temp=90° C.) δ 9.34 (bs, 1H), 8.71 (s, 1H), 8.38-8.33 (m, 1H), 8.23 (d, J=1.9 Hz, 1H), 7.97 (d, J=1.9 Hz, 1H), 7.86-7.75 (m, 2H), 7.44-7.38 (m, 2H), 7.32-7.26 (m, 2H), 6.69-6.62 (m, 1H), 4.43-4.38 (m, 2H), 2.29-2.18 (m, 3H), 1.81-1.68 (m, 2H), 1.67-1.45 (m, 4H), 1.29-1.15 (m, 2H); MS (ESI(+)) m/e 392 (M+H) + .
Example 62
1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea
Example 62A
4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 62B
1-imidazo[1,2-a]pyridin-6-yl-3-(4-{1-[(propan-2-yloxy)acetyl]piperidin-4-yl}butyl)urea
The title compound was prepared as described in Example 1A, substituting 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]butyl}piperidine for 3-methylbutan-1-amine and 2-isopropoxyacetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 /D 2 O) 6 ppm 9.18 (dd, J=1.9, 0.8 Hz, 1H), 8.30-8.19 (m, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.84 (d, J=9.7 Hz, 1H), 7.76-7.72 (m, 1H), 4.03 (s, 4H), 3.72-3.52 (m, 1H), 3.14 (t, J=6.9 Hz, 2H), 2.77 (s, 2H), 1.69 (dd, J=12.9, 2.3 Hz, 2H), 1.58-1.40 (m, 4H), 1.41-1.31 (m, 2H), 1.31-1.21 (m, 2H), 1.11 (t, J=5.2 Hz, 6H), 1.03 (d, J=10.2 Hz, 2H); MS (ESI(+)) m/e 416 (M+H) + .





TABLE 5



The following Examples were prepared essentially as described in Example 62,

substituting the appropriate carboxylic acid in Example 62B. Some products were purified

by flash chromatography while others were purified by reverse-phase HPLC. Accordingly,

some Examples were isolated as trifluoroacetic acid salts.






Ex
Name
1 H NMR
MS








63
1-{4-[1-(1,4-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


dioxan-2-
Temp = 90° C.) δ ppm 9.17 (dd, J = 2.0, 0.8 Hz,
m/e 430


ylcarbonyl)piperidin-
1H), 8.23 (d, J = 1.7 Hz, 1H), 7.97 (d, J = 2.1 Hz,
(M + H) +


4-yl]butyl}-
1H), 7.83 (d, J = 9.7 Hz, 1H),


3-imidazo[1,2-
7.74 (dd, J = 9.7, 1.9 Hz, 1H), 4.27 (dt, J = 16.5,


a]pyridin-6-
8.3 Hz, 1H), 3.80-3.70 (m, 2H),


ylurea
3.70-3.58 (m, 3H), 3.58-3.43 (m, 1H),



3.13 (q, J = 7.1 Hz, 2H), 1.69 (d, J = 11.6 Hz,



2H), 1.56-1.43 (m, 4H),



1.42-1.21 (m, 6H), 1.03 (s, 2H)

64
1-{4-[1-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


(cyclopropylacetyl)piperidin-
Temp = 90° C.) δ ppm 9.25-9.11 (m, 1H),
m/e 398


4-
8.24 (d, J = 1.8 Hz, 1H), 7.98 (d, J = 2.0 Hz,
(M + H) +


yl]butyl}-3-
1H), 7.84 (d, J = 9.7 Hz, 1H),


imidazo[1,2-
7.81-7.71 (m, 1H), 3.98 (s, 1H), 3.24-3.06 (m,


a]pyridin-6-
3H), 2.23 (d, J = 6.7 Hz, 2H), 1.68 (d, J = 12.9 Hz,


ylurea
2H), 1.61-1.41 (m, 4H),



1.39-1.20 (m, 4H), 1.09-0.85 (m, 4H),



0.49-0.35 (m, 2H), 0.22-0.05 (m, 2H)

65
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.24-9.11 (m, 1H),
m/e 440


{4-[1-(4,4,4-
8.23 (d, J = 2.1 Hz, 1H), 7.97 (d, J = 2.0 Hz,
(M + H) +


trifluorobutanoyl)piperidin-
1H), 7.83 (d, J = 9.7 Hz, 1H),


4-
7.77-7.69 (m, 1H), 3.14 (t, J = 6.9 Hz, 2H),


yl]butyl}urea
2.56 (dd, J = 10.8, 4.4 Hz, 3H), 2.51-2.40 (m,



2H), 1.69 (d, J = 12.0 Hz, 2H),



1.63-1.43 (m, 4H), 1.41-1.22 (m, 4H), 0.98 (dd, J = 36.1,



8.5 Hz, 2H)

66
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz,
m/e 402


{4-[1-
1H); 8.23 (d, J = 2.0 Hz, 1H), 7.97 (d, J = 2.1 Hz,
(M + H) +


(tetrahydro-2H-
1H), 7.82 (d, J = 9.3 Hz, 1H),


pyran-4-
7.73 (dd, J = 9.7, 1.9 Hz, 1H), 7.55 (dd, J = 8.4,


ylacetyl)piperidin-
4.5 Hz, 2H), 4.46 (d, J = 12.6 Hz, 2H),


4-yl]butyl}urea
3.16 (dd, J = 18.1, 11.2 Hz, 2H), 2.78 (t, J = 12.3 Hz,



3H), 1.68 (d, J = 9.8 Hz, 2H),



1.54-1.42 (m, 4H), 1.33 (s, 8H), 1.26 (t, J = 7.0 Hz,



3H), 1.11-0.99 (m, 2H)

67
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz,
m/e 442


{4-[1-
1H), 8.30-8.19 (m, 1H), 7.98 (d, J = 2.1 Hz,
(M + H) +


(tetrahydrofuran-
1H), 7.83 (d, J = 9.6 Hz, 1H),


2-
7.75 (dd, J = 9.6, 1.9 Hz, 1H), 3.88-3.71 (m,


ylacetyl)piperidin-
2H), 3.14 (t, J = 6.9 Hz, 2H), 2.23 (t, J = 6.9 Hz,


4-yl]butyl}urea
2H), 1.91 (ttd, J = 10.7, 6.9, 3.5 Hz,



1H), 1.68 (d, J = 12.1 Hz, 2H), 1.56 (t, J = 12.5 Hz,



2H), 1.53-1.42 (m, 4H),



1.42-1.28 (m, 2H), 1.22 (m, 4H), 0.99 (d, J = 10.1 Hz,



2H)

68
1-{4-[1-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


(cyclopentylcarbonyl)piperidin-
Temp = 90° C.) δ ppm 9.23-9.13 (m, 1H),
m/e 412


4-
8.23 (d, J = 2.1 Hz, 1H), 7.97 (d, J = 2.0 Hz,
(M + H) +


yl]butyl}-3-
1H), 7.83 (d, J = 9.7 Hz, 1H),


imidazo[1,2-
7.82-7.71 (m, 1H), 4.12 (s, 2H), 3.98 (s, 1H),


a]pyridin-6-
3.14 (t, J = 6.9 Hz, 2H), 3.04-2.89 (m,


ylurea
2H), 2.77 (s, 2H), 1.87-1.59 (m, 8H),



1.51-1.33 (m, 6H), 1.40-1.10 (m, 4H),



1.08-0.91 (m, 2H)

69
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ 9 ppm.23-9.14 (m, 1H),
m/e 428


{4-[1-
8.24 (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.1 Hz,
(M + H) +


(tetrahydro-2H-
1H), 7.84 (d, J = 9.7 Hz, 1H),


pyran-4-
7.79-7.68 (m, 1H), 4.11 (s, 2H), 3.88-3.77 (m,


ylcarbonyl)piperidin-
2H), 3.51-3.36 (m, 2H), 3.21-3.09 (m,


4-
2H), 2.92-2.73 (m, 2H), 1.76-1.56 (m,


yl]butyl}urea
4H), 1.56-1.42 (m, 6H), 1.45-1.18 (m,



4H), 1.04-0.87 (m, 2H)

70
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.17 (dd, J = 1.9, 0.8 Hz,
m/e 432


(4-{1-[(2-
1H), 8.24 (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.1 Hz,
(M + H) +


methoxyethoxy)acetyl]piperidin-
1H), 7.84 (d, J = 9.7 Hz, 1H),


4-
7.75 (dd, J = 9.7, 1.9 Hz, 1H), 4.09 (d, J = 7.6 Hz,


yl}butyl)urea
2H), 3.56 (dd, J = 6.0, 3.8 Hz, 2H),



3.47 (dd, J = 5.7, 3.7 Hz, 2H), 3.26 (s, 2H),



3.19-3.07 (m, 2H), 1.68 (dd, J = 13.0, 2.2 Hz,



2H), 1.48 (dt, J = 14.1, 7.0 Hz, 4H),



1.40-1.22 (m, 6H), 1.04 (d, J = 9.3 Hz,



2H)

71
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.26-9.11 (m, 1H),
m/e 443


{4-[1-
8.23 (d, J = 1.8 Hz, 1H), 7.98 (d, J = 2.1 Hz,
(M + H) +


(morpholin-4-
1H), 7.83 (t, J = 8.1 Hz, 1H),


ylacetyl)piperidin-
7.80-7.71 (m, 1H), 4.22 (s, 2H), 3.98 (s, 1H),


4-yl]butyl}urea
3.93-3.84 (m, 4H), 3.62 (s, 1H),



3.18-3.07 (m, 2H), 2.71 (s, 2H), 1.80-1.67 (m,



2H), 1.51 (dq, J = 21.7, 7.0 Hz, 4H),



1.42-1.20 (m, 6H), 1.07 (s, 2H)

72
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.25-9.14 (m, 1H),
m/e 414


{4-[1-
8.24 (d, J = 1.9 Hz, 1H), 7.98 (d, J = 2.0 Hz,
(M + H) +


(tetrahydrofuran-
1H), 7.84 (d, J = 9.7 Hz, 1H),


3-
7.79-7.69 (m, 1H), 3.85 (t, J = 8.1 Hz, 2H),


ylcarbonyl)piperidin-
3.70 (h, J = 7.8 Hz, 4H), 3.20-3.08 (m, 2H),


4-
2.09-1.91 (m, 2H), 1.70 (d, J = 12.1 Hz,


yl]butyl}urea
2H), 1.61-1.43 (m, 4H), 1.37-1.24 (m,



4H), 1.08-0.88 (m, 2H)

73
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.22-9.12 (m, 1H),
m/e 428


{4-[1-
8.24 (d, J = 2.1 Hz, 1H), 7.98 (d, J = 2.0 Hz,
(M + H) +


(tetrahydrofuran-
1H), 7.84 (d, J = 9.7 Hz, 1H),


3-
7.79-7.69 (m, 1H), 3.98 (s, 1H), 3.86-3.76 (m,


ylacetyl)piperidin-
1H), 3.75-3.68 (m, 1H), 3.68-3.57 (m,


4-yl]butyl}urea
1H), 3.28-3.23 (m, 1H), 3.14 (t, J = 6.9 Hz,



2H), 2.50-2.43 (m, 1H),



2.43-2.30 (m, 2H), 2.09-1.92 (m, 1H), 1.68 (d, J = 13.3 Hz,



2H), 1.56-1.41 (m, 6H),



1.38-1.29 (m, 2H), 1.25 (dd, J = 14.2, 6.0 Hz,



2H), 1.00 (d, J = 10.2 Hz, 2H)

74
1-imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 /D 2 O,
(ESI(+))


a]pyridin-6-yl-3-
Temp = 90° C.) δ ppm 9.18 (d, J = 1.1 Hz,
m/e 414


{4-[1-
1H), 8.24 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 2.0 Hz,
(M + H) +


(tetrahydrofuran-
1H), 7.84 (d, J = 9.6 Hz, 1H),


2-
7.79-7.65 (m, 1H), 4.59 (t, J = 6.7 Hz, 1H),


ylcarbonyl)piperidin-
4.12 (s, 2H), 3.88-3.62 (m, 2H), 3.16 (dd,


4-
J = 18.1, 11.3 Hz, 2H), 2.02-1.93 (m,


yl]butyl}urea
2H), 1.93-1.72 (m, 2H), 1.69 (d, J = 12.7 Hz,



2H), 1.58-1.43 (m, 4H),



1.42-1.19 (m, 5H), 1.17-0.87 (m, 2H)

107
1-[4-(1-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


benzoylpiperidin-
8.82-8.77 (m, 1H), 7.76 (s, 1H), 7.50 (s,
m/e 420


4-yl)butyl]-3-
1H), 7.48-7.40 (m, 4H), 7.42-7.33 (m,
(M + H) +


imidazo[1,2-
2H), 7.09 (dd, J = 9.5, 2.0 Hz, 1H),


a]pyridin-6-
4.65-4.57 (m, 1H), 3.74-3.65 (m, 1H), 3.21 (t,


ylurea
J = 6.9 Hz, 2H), 3.13-3.03 (m, 1H),



2.88-2.78 (m, 1H), 1.90-1.82 (m, 1H),



1.74-1.46 (m, 4H), 1.48-1.26 (m, 4H),



1.28-1.04 (m, 2H)

270
1-[4-(1-

(ESI(+))


benzoylpiperidin-

m/e 420


4-yl)butyl]-3-

(M + H) +


imidazo[1,2-


a]pyridin-7-


ylurea































































































































































Example 75
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
Example 75A
5-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 75B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 5-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.99 (t, J=5.8 Hz, 1H), 8.46 (s, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.79 (s, 1H), 7.69 (d, J=3.9 Hz, 1H), 7.49-7.58 (m, 2H), 7.20 (d, J=4.0 Hz, 2H), 4.43 (d, J=5.7 Hz, 2H), 3.91 (d, J=7.2 Hz, 2H), 2.11 (dq, J=13.6, 6.8 Hz, 1H), 0.84 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 380 (M+H)+.





TABLE 6



The following Examples were prepared essentially as described in Example 75,

substituting the appropriate carboxylic acid and amine in Example 75A and the appropriate

boronate in Example 75B. Some boronates were Boc-protected and required deprotection as

in Example 28A.






Ex
Name
1 H NMR
MS








120
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm
(ESI(+))


a]pyridin-6-
8.87 (t, J = 6.0 Hz, 1 H), 8.46 (s, 1 H),
m/e 364


ylmethyl)-5-[1-
8.14 (s, 1 H), 7.96 (s, 1 H), 7.87 (s, 1 H),
(M + H) +


(2-methylpropyl)-
7.53 (d, J = 6.8 Hz, 2 H), 7.21 (dd, J = 9.3, 1.4 Hz,


1H-pyrazol-4-
1 H), 7.14 (d, J = 3.6 Hz, 1 H), 6.64 (d,


yl]furan-2-
J = 3.5 Hz, 1 H), 4.44 (d, J = 6.0 Hz, 2 H),


carboxamide
3.94 (d, J = 7.2 Hz, 2 H), 2.11 (dq, J = 13.6,



6.8 Hz, 1 H), 0.83 (d, J = 6.7 Hz, 6 H)

174
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm
(ESI(+))


a]pyridin-7-
9.04 (t, J = 6.0 Hz, 1 H), 8.48 (d, J = 7.0 Hz,
m/e 380


ylmethyl)-5-[1-
1 H), 8.14 (s, 1 H), 7.88 (s, 1 H), 7.80 (s, 1
(M + H) +


(2-methylpropyl)-
H), 7.73 (d, J = 3.8 Hz, 1 H), 7.51 (s, 1 H),


1H-pyrazol-4-
7.38 (s, 1 H), 7.21 (d, J = 3.9 Hz, 1 H),


yl]thiophene-2-
6.84 (dd, J = 7.0, 1.5 Hz, 1 H), 4.46 (d, J = 5.9 Hz,


carboxamide
2 H), 3.91 (d, J = 7.3 Hz, 2 H),



2.11 (dq, J = 13.6, 6.7, 6.6 Hz, 1 H), 0.84 (d,



J = 6.7 Hz, 6 H)

175
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
9.09 (t, J = 5.9 Hz, 1 H), 8.81 (s, 1 H),


ylmethyl)-5-[1-
8.47 (s, 1 H), 8.31 (s, 1 H), 7.95 (s, 1 H),


(2-
7.76 (d, J = 3.9 Hz, 1 H), 7.54 (t, J = 4.6 Hz, 2 H),


methylpropanoyl)-
7.50 (d, J = 3.9 Hz, 1 H), 7.20 (dd, J = 9.2,


1H-pyrazol-4-
1.5 Hz, 1 H), 4.44 (d, J = 5.9 Hz, 2 H),


yl]thiophene-2-
3.77 (dq, J = 6.9 Hz, 1 H), 1.21 (d, J = 6.9 Hz, 6


carboxamide
H)

176
5-[1-(2-hydroxy-
1 H NMR (400 MHz, DMSO-d 6 ) ppm
(ESI(+))


2-methylpropyl)-
9.00 (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H),
m/e 396


1H-pyrazol-4-yl]-
8.03 (s, 1 H), 7.95 (s, 1 H), 7.78 (s, 1 H),
(M + H) +


N-(imidazo[1,2-
7.69 (d, J = 3.8 Hz, 1 H), 7.49-7.58 (m, 2 H),


a]pyridin-6-
7.16-7.25 (m, 2 H), 4.76 (s, 1 H),


ylmethyl)thiophene-
4.42 (d, J = 5.7 Hz, 2 H), 4.01 (s, 2 H), 1.06 (s, 6


2-carboxamide
H)

177
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
9.00 (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H),


ylmethyl)-5-{1-
8.19 (s, 1 H), 7.95 (s, 1 H), 7.83 (s, 1 H),


[(3-methyloxetan-
7.70 (d, J = 3.9 Hz, 1 H), 7.48-7.58 (m, 2 H),


3-yl)methyl]-1H-
7.15-7.24 (m, 2 H), 4.59 (d, J = 6.0 Hz, 2


pyrazol-4-
H), 4.42 (d, J = 5.9 Hz, 2 H), 4.33 (s, 2 H),


yl}thiophene-2-
4.22 (d, J = 6.0 Hz, 2 H), 1.13 (s, 3 H)


carboxamide

178
5-[1-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


(cyclobutylmethyl)-
8.99 (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H),


1H-pyrazol-4-
8.13 (s, 1 H), 7.95 (s, 1 H), 7.77 (s, 1 H),


yl]-N-
7.69 (d, J = 3.9 Hz, 1 H), 7.48-7.57 (m, 2 H),


(imidazo[1,2-
7.16-7.23 (m, 2 H), 4.42 (d, J = 5.7 Hz, 2


a]pyridin-6-
H), 4.12 (d, J = 7.3 Hz, 2 H), 2.74 (dq,


ylmethyl)thiophene-
J = 7.5, 7.4 Hz, 1 H), 1.90-2.02 (m, 2 H),


2-carboxamide
1.67-1.90 (m, 4 H)

179
5-[1-
1 H NMR (400 MHz, DMSO-d 6 ) ppm
(ESI(+))


(cyclohexylmethyl)-
8.99 (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H),
m/e 420


1H-pyrazol-4-
8.12 (s, 1 H), 7.95 (s, 1 H), 7.78 (s, 1 H),
(M + H) +


yl]-N-
7.69 (d, J = 3.9 Hz, 1 H), 7.48-7.57 (m, 2 H),


(imidazo[1,2-
7.14-7.26 (m, 2 H), 4.42 (d, J = 5.9 Hz, 2


a]pyridin-6-
H), 3.93 (d, J = 7.2 Hz, 2 H),


ylmethyl)thiophene-
1.72-1.88 (m, 1 H), 1.54-1.70 (m, 3 H), 1.50 (d,


2-carboxamide
J = 12.1 Hz, 2 H), 1.03-1.28 (m, 3 H),



0.85-1.01 (m, 2 H)

180
5-{1-[(2R)-2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


hydroxybutyl]-
8.99 (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H),


1H-pyrazol-4-yl}-
8.08 (s, 1 H), 7.95 (s, 1 H), 7.78 (s, 1 H),


N-(imidazo[1,2-
7.69 (d, J = 3.9 Hz, 1 H), 7.50-7.58 (m, 2 H),


a]pyridin-6-
7.17-7.23 (m, 2 H), 4.92 (d, J = 5.4 Hz, 1


ylmethyl)thiophene-
H), 4.42 (d, J = 5.7 Hz, 2 H),


2-carboxamide
4.03-4.12 (m, 1 H), 3.93-4.02 (m, 1 H),



3.66-3.76 (m, 1 H), 1.20-1.44 (m, 2 H), 0.88 (t,



J = 7.4 Hz, 3 H)

182
5-[1-(2-hydroxy-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


2-methylpropyl)-
9.04 (t, J = 5.9 Hz, 1 H), 8.48 (d, J = 7.0 Hz,


1H-pyrazol-4-yl]-
1 H), 8.04 (s, 1 H), 7.88 (s, 1 H), 7.79 (s, 1


N-(imidazo[1,2-
H), 7.73 (d, J = 3.8 Hz, 1 H), 7.51 (s, 1 H),


a]pyridin-7-
7.38 (s, 1 H), 7.23 (d, J = 3.8 Hz, 1 H),


ylmethyl)thiophene-
6.84 (dd, J = 7.0, 1.3 Hz, 1 H), 4.75 (s, 1 H),


2-carboxamide
4.46 (d, J = 5.9 Hz, 2 H), 4.01 (s, 2 H),



1.07 (s, 6 H)

186
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm
(ESI(+))


a]pyridin-6-
9.00 (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H),
m/e 422


ylmethyl)-5-[1-
8.07 (s, 1 H), 7.95 (s, 1 H), 7.78 (s, 1 H),
(M + H) +


(tetrahydro-2H-
7.69 (d, J = 3.8 Hz, 1 H), 7.48-7.57 (m, 2 H),


pyran-2-
7.14-7.27 (m, 2 H), 4.42 (d, J = 5.9 Hz, 2


ylmethyl)-1H-
H), 4.05-4.15 (m, 2 H), 3.83 (d, J = 11.1 Hz,


pyrazol-4-
1 H), 3.55-3.71 (m, 1 H),


yl]thiophene-2-
3.19-3.37 (m, 2 H), 1.68-1.85 (m, 1 H),


carboxamide
1.48-1.63 (m, 1 H), 1.32-1.50 (m, 2 H),



1.06-1.29 (m, 1 H)

200
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
9.00 (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H),


ylmethyl)-5-[1-
8.20 (s, 1 H), 7.95 (s, 1 H), 7.81 (s, 1 H),


(tetrahydrofuran-
7.69 (d, J = 3.9 Hz, 1 H), 7.49-7.57 (m, 2 H),


3-ylmethyl)-1H-
7.15-7.24 (m, 2 H), 4.42 (d, J = 5.7 Hz, 2


pyrazol-4-
H), 4.10 (d, J = 7.5 Hz, 2 H),


yl]thiophene-2-
3.69-3.79 (m, 1 H), 3.56-3.70 (m, 2 H), 3.46 (dd,


carboxamide
J = 8.7, 5.4 Hz, 2 H), 1.81-1.98 (m, 1 H),



1.52-1.65 (m, 1 H)

201
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
8.99 (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H),


ylmethyl)-5-[1-
8.14 (s, 1 H), 7.95 (s, 1 H), 7.80 (s, 1 H),


(tetrahydro-2H-
7.69 (d, J = 3.9 Hz, 1 H), 7.48-7.58 (m, 2 H),


pyran-4-
7.12-7.25 (m, 2 H), 4.43 (d, J = 5.7 Hz, 2


ylmethyl)-1H-
H), 4.00 (d, J = 7.2 Hz, 2 H), 3.81 (dd,


pyrazol-4-
J = 11.3, 2.9 Hz, 2 H), 3.24 (td, J = 11.6, 1.7 Hz,


yl]thiophene-2-
2 H), 1.91-2.18 (m, 1 H), 1.39 (dd,


carboxamide
J = 12.7, 1.4 Hz, 2 H), 1.14-1.30 (m, 2 H)

206
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
8.99 (t, J = 5.8 Hz, 1 H), 8.46 (s, 1 H),


ylmethyl)-5-[1-
8.15 (s, 1 H), 7.95 (s, 1 H), 7.80 (s, 1 H),


(tetrahydro-2H-
7.69 (d, J = 3.9 Hz, 1 H), 7.53 (t, J = 4.6 Hz, 2 H),


pyran-3-
7.15-7.26 (m, 2 H), 4.43 (d, J = 5.9 Hz, 2


ylmethyl)-1H-
H), 4.02 (dd, J = 7.2, 3.2 Hz, 2 H),


pyrazol-4-
3.64-3.72 (m, 1 H), 3.61 (dd, J = 11.1, 3.3 Hz, 1


yl]thiophene-2-
H), 3.15 (dd, J = 11.2, 8.8 Hz, 1 H),


carboxamide
1.96-2.18 (m, 1 H), 1.52-1.70 (m, 2 H),



1.34-1.51 (m, 1 H), 1.10-1.31 (m, 2 H)

219
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) ppm


a]pyridin-6-
8.99 (t, J = 5.9 Hz, 1 H), 8.46 (s, 1 H),


ylmethyl)-5-[1-
8.10 (s, 1 H), 7.95 (s, 1 H), 7.79 (s, 1 H),


(tetrahydrofuran-
7.70 (d, J = 3.9 Hz, 1 H), 7.46-7.60 (m, 2 H),


2-ylmethyl)-1H-
7.11-7.26 (m, 2 H), 4.43 (d, J = 5.9 Hz, 2


pyrazol-4-
H), 4.04-4.25 (m, 3 H), 3.69-3.80 (m, 1


yl]thiophene-2-
H), 3.62 (q, J = 7.4 Hz, 1 H),


carboxamide
1.86-2.01 (m, 1 H), 1.68-1.84 (m, 2 H),



1.52-1.67 (m, 1 H)

247
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 422


ylmethyl)-5-[1-

(M + H) +


(tetrahydro-2H-


pyran-2-


ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

248
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 408


ylmethyl)-5-[1-

(M + H) +


(tetrahydrofuran-


2-ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

252
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 408


ylmethyl)-5-[1-

(M + H) +


(tetrahydrofuran-


3-ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

253
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.04 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.2,
m/e 422


ylmethyl)-5-[1-
1.1 Hz, 1H), 8.16 (s, 1H), 7.89 (t, J = 1.0 Hz,
(M + H) +


(tetrahydro-2H-
1H), 7.82 (s, 1H), 7.74 (d, J = 3.9 Hz,


pyran-3-
1H), 7.52 (d, J = 1.4 Hz, 1H), 7.40 (s, 1H),


ylmethyl)-1H-
7.22 (d, J = 3.8 Hz, 1H), 6.85 (dd, J = 7.0,


pyrazol-4-
1.7 Hz, 1H), 4.48 (d, J = 5.7 Hz, 2H),


yl]thiophene-2-
4.03 (dd, J = 7.3, 2.1 Hz, 2H), 3.76-3.57 (m,


carboxamide
2H), 3.42-3.32 (m, 1H), 3.17 (dd, J = 11.2,



8.7 Hz, 1H), 2.15-1.98 (m, 1H),



1.77-1.54 (m, 2H), 1.54-1.35 (m, 1H),



1.32-1.14 (m, 1H)

254
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 408


ylmethyl)-5-{1-

(M + H) +


[(3-methyloxetan-


3-yl)methyl]-1H-


pyrazol-4-


yl}thiophene-2-


carboxamide

265
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 422


ylmethyl)-5-[1-

(M + H) +


(tetrahydro-2H-


pyran-4-


ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

269
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 5.9 Hz, 1H), 8.53-8.45 (m,
m/e 382


ylmethyl)-5-[1-
1H), 8.13 (s, 1H), 7.89 (s, 1H), 7.81 (s,
(M + H) +


(2-methoxyethyl)-
1H), 7.74 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.1 Hz,


1H-pyrazol-4-
1H), 7.40 (s, 1H), 7.22 (d, J = 3.8 Hz,


yl]thiophene-2-
1H), 6.85 (dd, J = 7.0, 1.6 Hz, 1H),


carboxamide
4.48 (d, J = 5.9 Hz, 2H), 4.27 (t, J = 5.3 Hz,



2H), 3.70 (t, J = 5.3 Hz, 2H), 3.24 (s,



3H)

272
5-[1-
1 H NMR (300 MHz, DMSO-d 6 ) ppm
(ESI(+))


(cyclohexylmethyl)-
9.04 (t, J = 6.1 Hz, 1H), 8.49 (d, J = 7.8 Hz,
m/e 448


5-ethyl-1H-
1H), 7.89 (s, 1H), 7.78 (d, J = 4.1 Hz,
(M + H) +


pyrazol-4-yl]-N-
1H), 7.72 (s, 1H), 7.52 (d, J = 1.0 Hz,


(imidazo[1,2-
1H), 7.40 (s, 1H), 7.17 (d, J = 4.1 Hz,


a]pyridin-7-
1H), 6.85 (dd, J = 7.1, 1.7 Hz, 1H),


ylmethyl)thiophene-
4.48 (d, J = 5.8 Hz, 2H), 3.90 (d, J = 7.5 Hz,


2-carboxamide
2H), 2.87 (q, J = 7.2 Hz, 2H),



1.79-1.95 (m, 1H), 1.59-1.73 (m, J = 3.4 Hz, 3H),



1.54 (d, J = 12.5 Hz, 2H), 1.09-1.25 (m,



6H), 0.93-1.08 (m, J = 11.9 Hz, 2H)

273
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.1 Hz,
m/e 492


ylmethyl)-5-{1-
1H), 7.89 (s, 1H), 7.79 (d, J = 3.7 Hz,
(M + H) +


[(1-methoxy-3,3-
1H), 7.74 (s, 1H), 7.52 (d, J = 1.0 Hz,


dimethylcyclohexyl)methyl]-
1H), 7.40 (s, 1H), 7.18 (d, J = 4.1 Hz,


5-
1H), 6.85 (dd, J = 7.1, 1.7 Hz, 1H),


methyl-1H-
4.48 (d, J = 5.8 Hz, 2H), 3.97-4.16 (m, 2H),


pyrazol-4-
3.20 (s, 3H), 2.45 (s, 3H), 1.64-1.78 (m,


yl}thiophene-2-
1H), 1.27-1.59 (m, 4H), 0.99-1.24 (m,


carboxamide
3H), 0.96 (s, 3H), 0.85 (s, 3H)

293
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (s, 1H), 8.47 (t, J = 9.6 Hz, 1H),
m/e 366


ylmethyl)-5-(1-
8.17 (s, 1H), 7.89 (s, 1H), 7.80 (s, 1H), 7.74 (d,
(M + H) +


propyl-1H-
J = 3.9 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H),


pyrazol-4-
7.40 (s, 1H), 7.22 (d, J = 3.8 Hz, 1H),


yl)thiophene-2-
6.83 (dt, J = 14.9, 7.4 Hz, 1H), 4.48 (d, J = 5.9 Hz,


carboxamide
2H), 4.07 (t, J = 7.0 Hz, 2H), 1.81 (dd,



J = 14.4, 7.2 Hz, 2H), 0.84 (t, J = 7.4 Hz,



3H)

294
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.0 Hz,
m/e 437


ylmethyl)-5-{1-
1H), 8.17 (s, 1H), 7.89 (s, 1H),
(M + H) +


[2-(morpholin-4-
7.80 (s, 1H), 7.74 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz,


yl)ethyl]-1H-
1H), 7.40 (s, 1H), 7.22 (d, J = 3.8 Hz,


pyrazol-4-
1H), 6.85 (dd, J = 7.0, 1.5 Hz,


yl}thiophene-2-
1H), 4.48 (d, J = 5.9 Hz, 2H), 4.24 (t, J = 6.5 Hz,


carboxamide
2H), 3.59-3.49 (m, 4H), 2.72 (t, J = 6.5 Hz,



2H), 2.45-2.35 (m, 4H)

295
5-(1-ethyl-1H-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


pyrazol-4-yl)-N-
9.02 (t, J = 5.9 Hz, 1H), 8.49 (d, J = 7.0 Hz,
m/e 352


(imidazo[1,2-
1H), 8.17 (s, 1H), 7.89 (s, 1H),
(M + H) +


a]pyridin-7-
7.79 (s, 1H), 7.74 (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.2 Hz,


ylmethyl)thiophene-
1H), 7.40 (s, 1H), 7.21 (d, J = 3.8 Hz,


2-carboxamide
1H), 6.85 (dd, J = 7.0, 1.6 Hz,



1H), 4.48 (d, J = 5.9 Hz, 2H), 4.15 (q, J = 7.3 Hz,



2H), 1.39 (t, J = 7.3 Hz, 3H)

296
5-[1-(1,1-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


dioxidotetrahydro
9.05 (t, J = 6.0 Hz, 1H), 8.49 (d, J = 6.9 Hz,
m/e 442


thiophen-3-yl)-
1H), 8.32 (s, 1H), 7.94 (s, 1H),
(M + H) +


1H-pyrazol-4-yl]-
7.89 (s, 1H), 7.76 (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.1 Hz,


N-(imidazo[1,2-
1H), 7.40 (s, 1H), 7.26 (d, J = 3.8 Hz,


a]pyridin-7-
1H), 6.85 (dd, J = 7.0, 1.6 Hz,


ylmethyl)thiophene-
1H), 5.35-5.18 (m, 1H), 4.48 (d, J = 5.9 Hz,


2-carboxamide
2H), 3.75 (dd, J = 13.6, 8.2 Hz, 1H),



3.48 (m, 2H), 3.35-3.20 (m, 1H),



2.78-2.53 (m, 2H)

300
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.04 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0,
m/e 430


ylmethyl)-5-{1-
0.8 Hz, 1H), 8.25 (s, 1H), 7.89 (d, J = 1.4 Hz,
(M + H) +


[2-
2H), 7.75 (d, J = 3.9 Hz, 1H), 7.52 (d,


(methylsulfonyl)ethyl]-
J = 1.2 Hz, 1H), 7.40 (s, 1H), 7.24 (d, J = 3.8 Hz,


1H-pyrazol-
1H), 6.85 (dd, J = 7.0, 1.7 Hz,


4-yl}thiophene-2-
1H), 4.57 (t, J = 6.9 Hz, 2H), 4.48 (d, J = 5.9 Hz,


carboxamide
2H), 3.73 (t, J = 6.9 Hz, 2H),



2.93 (s, 3H)

304
5-{1-[(2R)-2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


hydroxypropyl]-
9.02 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0,
m/e 382


1H-pyrazol-4-yl}-
0.7 Hz, 1H), 8.09 (s, 1H), 7.89 (s, 1H),
(M + H) +


N-(imidazo[1,2-
7.80 (d, J = 0.5 Hz, 1H), 7.74 (d, J = 3.9 Hz,


a]pyridin-7-
1H), 7.52 (d, J = 1.2 Hz, 1H), 7.40 (s,


ylmethyl)thiophene-
1H), 7.22 (d, J = 3.8 Hz, 1H), 6.85 (dd, J = 7.0,


2-carboxamide
1.6 Hz, 1H), 4.93 (d, J = 4.7 Hz, 1H),



4.48 (d, J = 5.9 Hz, 2H), 4.11-3.93 (m,



3H), 1.12-0.98 (m, 3H)

316
5-[1-(1,4-dioxan-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


2-ylmethyl)-1H-
9.03 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0,
m/e 424


pyrazol-4-yl]-N-
0.7 Hz, 1H), 8.12 (s, 1H), 7.89 (s, 1H),
(M + H) +


(imidazo[1,2-
7.82 (s, 1H), 7.74 (d, J = 3.8 Hz, 1H),


a]pyridin-7-
7.52 (d, J = 1.2 Hz, 1H), 7.40 (s, 1H), 7.23 (d, J = 3.8 Hz,


ylmethyl)thiophene-
1H), 6.85 (dd, J = 7.0, 1.6 Hz,


2-carboxamide
1H), 4.48 (d, J = 5.9 Hz, 2H),



4.20-4.14 (m, 2H), 3.96-3.83 (m, 1H),



3.79-3.70 (m, 2H), 3.68-3.39 (m, 3H),



3.29-3.21 (m, 1H)

317
5-[1-(2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


hydroxyethyl)-
9.02 (t, J = 5.9 Hz, 1H), 8.49 (dd, J = 7.0,
m/e 368


1H-pyrazol-4-yl]-
0.7 Hz, 1H), 8.12 (s, 1H), 7.89 (d, J = 0.8 Hz,
(M + H) +


N-(imidazo[1,2-
1H), 7.80 (d, J = 0.6 Hz, 1H), 7.74 (d,


a]pyridin-7-
J = 3.8 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H),


ylmethyl)thiophene-
7.40 (s, 1H), 7.22 (d, J = 3.9 Hz, 1H),


2-carboxamide
6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.92 (t, J = 5.3 Hz,



1H), 4.48 (d, J = 5.9 Hz, 2H), 4.15 (t,



J = 5.6 Hz, 2H), 3.75 (q, J = 5.5 Hz, 2H)

344
5-{1-[(1,1-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


dioxidotetrahydro-
9.04 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.0,
m/e 470


2H-thiopyran-3-
0.8 Hz, 1H), 8.19 (d, J = 0.4 Hz, 1H),
(M + H) +


yl)methyl]-1H-
7.89 (d, J = 0.8 Hz, 1H), 7.86 (d, J = 0.5 Hz,


pyrazol-4-yl}-N-
1H), 7.75 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz,


(imidazo[1,2-
1H), 7.40 (s, 1H), 7.24 (d, J = 3.9 Hz,


a]pyridin-7-
1H), 6.85 (dd, J = 7.0, 1.7 Hz, 1H),


ylmethyl)thiophene-
4.48 (d, J = 5.8 Hz, 2H), 4.13 (d, J = 6.6 Hz,


2-carboxamide
2H), 3.09-2.83 (m, 4H),



2.47-2.40 (m, 1H), 2.14-1.96 (m, 1H),



1.88-1.69 (m, 1H), 1.69-1.54 (m, 1H),



1.37-1.14 (m, 1H)

345
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 6.0 Hz, 1H), 8.49 (d, J = 7.0 Hz,
m/e 338


ylmethyl)-5-(1-
1H), 8.12 (s, 1H), 7.89 (s, 1H),
(M + H) +


methyl-1H-
7.79 (s, 1H), 7.74 (d, J = 3.8 Hz, 1H), 7.52 (d, J = 1.1 Hz,


pyrazol-4-
1H), 7.40 (s, 1H), 7.21 (d, J = 3.8 Hz,


yl)thiophene-2-
1H), 6.84 (dd, J = 7.0, 1.6 Hz,


carboxamide
1H), 4.48 (d, J = 5.9 Hz, 2H), 3.86 (s, 3H)

363
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.22 (t, J = 5.9 Hz, 1H), 8.50 (dd, J = 6.9,
m/e 338


ylmethyl)-5-(1-
0.8 Hz, 1H), 7.92-7.86 (m, 2H), 7.53 (d,
(M + H) +


methyl-1H-
J = 1.2 Hz, 1H), 7.48 (d, J = 2.0 Hz, 1H),


pyrazol-5-
7.45 (d, J = 3.9 Hz, 1H), 7.41 (s, 1H),


yl)thiophene-2-
6.86 (dd, J = 7.0, 1.7 Hz, 1H), 6.59 (d, J = 1.9 Hz,


carboxamide
1H), 4.51 (d, J = 5.9 Hz, 2H), 3.98 (s,



3H)

395
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 6.9,
m/e 408


ylmethyl)-5-{1-
1.0 Hz, 1H), 8.12 (s, 1H), 7.89 (t, J = 1.0 Hz,
(M + H) +


[(2R)-
1H), 7.81 (s, 1H), 7.74 (d, J = 4.0 Hz,


tetrahydrofuran-
1H), 7.52 (d, J = 1.5 Hz, 1H), 7.40 (s, 1H),


2-ylmethyl]-1H-
7.23 (d, J = 4.0 Hz, 1H), 6.85 (dd, J = 7.0,


pyrazol-4-
1.7 Hz, 1H), 4.48 (d, J = 5.9 Hz, 2H),


yl}thiophene-2-
4.26-4.04 (m, 3H), 3.82-3.69 (m, 1H),


carboxamide
3.69-3.57 (m, 1H), 2.00-1.85 (m, 1H),



1.85-1.70 (m, 2H), 1.70-1.52 (m, 1H)

397
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.02 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 6.9,
m/e 408


ylmethyl)-5-{1-
1.0 Hz, 1H), 8.11 (d, J = 0.9 Hz, 1H),
(M + H) +


[(2S)-
7.89 (d, J = 0.9 Hz, 1H), 7.80 (d, J = 0.9 Hz,


tetrahydrofuran-
1H), 7.74 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.2 Hz,


2-ylmethyl]-1H-
1H), 7.43-7.37 (m, 1H), 7.23 (d,


pyrazol-4-
J = 3.9 Hz, 1H), 6.85 (dd, J = 7.1, 1.7 Hz,


yl}thiophene-2-
1H), 4.48 (d, J = 5.7 Hz, 2H),


carboxamide
4.27-4.06 (m, 3H), 3.82-3.69 (m, 1H),



3.69-3.58 (m, 1H), 2.01-1.86 (m, 1H),



1.86-1.69 (m, 2H), 1.69-1.52 (m, 1H)

410
N-(imidazo[1,2-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.03 (t, J = 6.0 Hz, 1H), 8.49 (d, J = 6.7 Hz,
m/e 408


ylmethyl)-5-[1-
1H), 8.24 (s, 1H), 7.89 (s, 1H),
(M + H) +


(tetrahydro-2H-
7.82 (s, 1H), 7.75 (d, J = 3.9 Hz, 1H), 7.52 (d, J = 1.1 Hz,


pyran-4-yl)-1H-
1H), 7.40 (s, 1H), 7.23 (d, J = 3.9 Hz,


pyrazol-4-
1H), 6.85 (dd, J = 7.0, 1.7 Hz,


yl]thiophene-2-
1H), 4.54-4.34 (m, 3H), 4.04-3.88 (m,


carboxamide
2H), 3.47 (td, J = 11.3, 3.9 Hz, 2H),



2.06-1.86 (m, 4H)

465
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.05 (t, J = 6.0 Hz, 1H), 8.50 (d, J = 7.0 Hz,
m/e 436


ylmethyl)-5-{1-
1H), 8.03 (s, 1H), 7.90 (s, 1H),
(M + H) +


[(2-
7.80 (s, 1H), 7.75 (d, J = 3.8 Hz, 1H), 7.54 (d, J = 1.1 Hz,


methyltetrahydro-
1H), 7.41 (s, 1H), 7.25 (d, J = 3.9 Hz,


2H-pyran-2-
1H), 6.86 (dd, J = 7.0, 1.6 Hz,


yl)methyl]-1H-
1H), 4.49 (d, J = 5.9 Hz, 2H), 4.24 (d, J = 14.1 Hz,


pyrazol-4-
1H), 4.10 (d, J = 14.0 Hz, 1H),


yl}thiophene-2-
3.81-3.67 (m, 1H), 3.65-3.52 (m, 1H),


carboxamide
1.71-1.55 (m, 2H), 1.52-1.31 (m, 4H),



1.07 (s, 3H)

466
tert-butyl 4-[(4-
1 H NMR (300 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


{5-[(imidazo[1,2-
9.02 (t, J = 6.0 Hz, 1H), 8.49 (dd, J = 7.1,
m/e 521


a]pyridin-7-
1.0 Hz, 1H), 8.14 (d, J = 0.8 Hz, 1H),
(M + H) +


ylmethyl)carbamoyl]thiophen-
7.89 (s, 1H), 7.81 (d, J = 0.9 Hz, 1H), 7.74 (d, J = 3.8 Hz,


2-
1H), 7.52 (d, J = 1.3 Hz, 1H),


yl}-1H-pyrazol-1-
7.40 (s, 1H), 7.22 (d, J = 3.9 Hz, 1H),


yl)methyl]piperidine-
6.84 (dd, J = 7.1, 1.7 Hz, 1H), 4.48 (d, J = 5.7 Hz,


1-carboxylate
2H), 4.02 (d, J = 7.0 Hz, 2H), 3.92 (d,



J = 13.2 Hz, 2H), 2.81-2.57 (m, 2H),



2.16-1.90 (m, 1H), 1.56-1.42 (m, 2H),



1.38 (s, 9H), 1.22-0.94 (m, 2H)

475
5-[1-

(ESI(+))


(cyclobutylmethyl)-

m/e 392


1H-pyrazol-4-

(M + H) +


yl]-N-


(imidazo[1,2-


a]pyridin-7-


ylmethyl)thiophene-


2-carboxamide

476
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 392


ylmethyl)-5-[1-

(M + H) +


(tetrahydrofuran-


2-ylmethyl)-1H-


pyrazol-4-


yl]furan-2-


carboxamide

477
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 406


ylmethyl)-5-[1-

(M + H) +


(tetrahydro-2H-


pyran-2-


ylmethyl)-1H-


pyrazol-4-


yl]furan-2-


carboxamide

478
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 392


ylmethyl)-5-[1-

(M + H) +


(tetrahydrofuran-


3-ylmethyl)-1H-


pyrazol-4-


yl]furan-2-


carboxamide

479
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 406


ylmethyl)-5-[1-

(M + H) +


(tetrahydro-2H-


pyran-3-


ylmethyl)-1H-


pyrazol-4-


yl]furan-2-


carboxamide

480
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 406


ylmethyl)-5-[1-

(M + H) +


(tetrahydro-2H-


pyran-4-


ylmethyl)-1H-


pyrazol-4-


yl]furan-2-


carboxamide

481
5-[1-

(ESI(+))


(cyclobutylmethyl)-

m/e 376


1H-pyrazol-4-

(M + H) +


yl]-N-


(imidazo[1,2-


a]pyridin-7-


ylmethyl)furan-2-


carboxamide

482
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 392


ylmethyl)-5-{1-

(M + H) +


[(3-methyloxetan-


3-yl)methyl]-1H-


pyrazol-4-


yl}furan-2-


carboxamide

483
5-[1-(2-hydroxy-

(ESI(+))


2-methylpropyl)-

m/e 380


1H-pyrazol-4-yl]-

(M + H) +


N-(imidazo[1,2-


a]pyridin-7-


ylmethyl)furan-2-


carboxamide

883
5-[1-(2,2-

(ESI(+))


dimethylpropyl)-

m/e 394


1H-pyrazol-4-yl]-

(M + H) +


N-(imidazo[1,2-


a]pyridin-7-


ylmethyl)thiophene-


2-carboxamide

884
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 472


ylmethyl)-5-[1-

(M + H) +


(tricyclo[3.3.1.1~3,


7~]dec-1-


ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

885
5-(1-benzyl-1H-

(ESI(+))


pyrazol-4-yl)-N-

m/e 414


(imidazo[1,2-

(M + H) +


a]pyridin-7-


ylmethyl)thiophene-


2-carboxamide

886
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 474


ylmethyl)-5-[1-

(M + H) +


(2-


oxatricyclo[3.3.1.1~3,


7~]dec-1-


ylmethyl)-1H-


pyrazol-4-


yl]thiophene-2-


carboxamide

1082
5-{1-[2,2-

(ESI(+))


dimethyl-3-

m/e 478


(piperazin-1-

(M + H) +


yl)propyl]-1H-


pyrazol-4-yl}-N-


(imidazo[1,2-


a]pyridin-7-


ylmethyl)thiophene-


2-carboxamide

1083
5-[1-(3-amino-

(ESI(+))


2,2-

m/e 409


dimethylpropyl)-

(M + H) +


1H-pyrazol-4-yl]-


N-(imidazo[1,2-


a]pyridin-7-


ylmethyl)thiophene-


2-carboxamide


























































































































































































































































































































































































































































































































Example 76
2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide
Example 76A
N-(imidazo[1,2-a]pyridin-6-yl)-2-(4-nitrophenyl)acetamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 2-(4-nitrophenyl)acetic acid for 4-nitrobenzoic acid.
Example 76B
2-(4-aminophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide
The title compound was prepared as described in Example 1B, substituting N-(imidazo[1,2-a]pyridin-6-yl)-2-(4-nitrophenyl)acetamide for N-isopentyl-4-nitrobenzamide.
Example 76C
2-cyclopentyl-N-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}acetamide
The title compound was prepared as described in Example 52A, substituting 2-(4-aminophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.71 (s, 1H), 9.83 (s, 1H), 9.55 (m, 1H), 8.38 (d, J=2.0 Hz, 1H), 8.08 (d, J=2.0 Hz, 1H), 7.96-7.88 (m, 1H), 7.80-7.73 (m, 1H), 7.58-7.51 (m, 2H), 7.29-7.23 (m, 2H), 3.67 (bs, 2H), 2.34-2.15 (m, 3H), 1.82-1.65 (m, 2H), 1.67-1.41 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 77
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide
Example 77A
tert-butyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenylcarbamate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid.
Example 77B
4-amino-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 77C
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-2-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 1A, substituting 4-amino-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-(tetrahydrofuran-2-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.14 (s, 1H), 8.93 (t, J=5.8 Hz, 1H), 8.48-8.45 (m, 1H), 7.95 (s, 1H), 7.88-7.82 (m, 2H), 7.71-7.64 (m, 2H), 7.53 (m, 7.55-7.48, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 4.23-4.12 (m, 1H), 3.82-3.72 (m, 1H), 3.66-3.56 (m, 1H), 2.59-2.44 (m, 2H), 2.07-1.95 (m, 1H), 1.92-1.77 (m, 2H), 1.60-1.47 (m, 1H); MS (ESI(+)) m/e 379 (M+H) + .
Example 78
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 77, substituting 2-(tetrahydrofuran-3-yl)acetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1 H NMR (500 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 9.87 (bs, 1H), 8.65-8.59 (m, 1H), 8.42 (s, 1H), 7.87 (s, 1H), 7.84-7.79 (m, 2H), 7.66-7.61 (m, 2H), 7.52-7.45 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.85-3.78 (m, 1H), 3.77-3.69 (m, 1H), 3.68-3.60 (m, 1H), 3.38-3.31 (m, 1H), 2.64-2.54 (m, 1H), 2.45-2.40 (m, 2H), 2.09-1.98 (m, 1H), 1.63-1.51 (m, 1H); MS (ESI(+)) m/e 379 (M+H) + .
Example 79
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 77, substituting 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1 H NMR (500 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 9.84 (bs, 1H), 8.67-8.60 (m, 1H), 8.42 (s, 1H), 7.87 (s, 1H), 7.85-7.79 (m, 2H), 7.67-7.61 (m, 2H), 7.52-7.45 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.85-3.77 (m, 2H), 3.35-3.26 (m, 2H), 2.28 (d, J=7.0 Hz, 2H), 2.07-1.96 (m, 1H), 1.65-1.57 (m, 2H), 1.31-1.22 (m, 2H); MS (ESI(+)) m/e 393 (M+H) + .
Example 80
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[(morpholin-4-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 77, substituting 2-morpholinoacetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1 H NMR (500 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 9.70 (bs, 1H), 8.69-8.63 (m, 1H), 8.42 (s, 1H), 7.90-7.81 (m, 3H), 7.70-7.65 (m, 2H), 7.53-7.45 (m, 2H), 7.21 (dd, J=9.3, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.67-3.61 (m, 4H), 3.14 (s, 2H), 2.56-2.52 (m, 4H); MS (ESI(+)) m/e 394 (M+H) + .
Example 81
4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 77, substituting 4-cyclopentylbutanoic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.10 (s, 1H), 8.92 (t, J=5.8 Hz, 1H), 8.46 (dd, J=1.9, 0.9 Hz, 1H), 7.95 (dd, J=1.2, 0.6 Hz, 1H), 7.87-7.81 (m, 2H), 7.70-7.64 (m, 2H), 7.55-7.49 (m, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.37-2.30 (m, 2H), 1.81-1.68 (m, 3H), 1.64-1.41 (m, 6H), 1.19-1.02 (m, 2H); MS (ESI(+)) m/e 391 (M+H) + .
Example 82
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[(propan-2-yloxy)acetyl]amino}benzamide
The title compound was prepared as described in Example 77, substituting 2-isopropoxyacetic acid for 2-(tetrahydrofuran-2-yl)acetic acid in Example 77C. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.78 (s, 1H), 8.95 (t, J=5.8 Hz, 1H), 8.49-8.44 (m, 1H), 7.97-7.93 (m, 1H), 7.89-7.83 (m, 2H), 7.78-7.72 (m, 2H), 7.56-7.50 (m, 2H), 7.22 (dd, J=9.2, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 4.04 (s, 2H), 3.75-3.64 (m, 1H), 1.17 (d, J=6.1 Hz, 6H); MS (ESI(+)) m/e 367 391 (M+H) + .
Example 83
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
Example 83A
4-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-bromobenzoic acid for 4-nitrobenzoic acid.
Example 83B
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.49-8.45 (m, 1H), 7.97-7.93 (m, 1H), 7.91-7.84 (m, 2H), 7.61-7.48 (m, 4H), 7.22 (dd, J=9.3, 1.7 Hz, 1H), 6.32-6.25 (m, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.05-3.99 (m, 2H), 3.58-3.50 (m, 2H), 2.55-2.44 (m, 2H), 1.43 (s, 9H); MS (ESI(+)) m/e 433 (M+H) + .
Example 84
N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide
Example 84A
N-(4-nitrobenzyl)imidazo[1,2-a]pyridine-6-carboxamide
The title compound was prepared as described in Example 1A, substituting (4-nitrophenyl)methanamine for 3-methylbutan-1-amine and imidazo[1,2-a]pyridine-6-carboxylic acid for 4-nitrobenzoic acid.
Example 84B
N-(4-aminobenzyl)imidazo[1,2-a]pyridine-6-carboxamide
The title compound was prepared as described in Example 1B, substituting N-(4-nitrobenzyl)imidazo[1,2-a]pyridine-6-carboxamide for N-isopentyl-4-nitrobenzamide.
Example 84C
N-{4-[(cyclopentylacetyl)amino]benzyl}imidazo[1,2-a]pyridine-6-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(4-aminobenzyl)imidazo[1,2-a]pyridine-6-carboxamide for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.80 (s, 1H), 9.16-9.11 (m, 1H), 9.04 (t, J=5.9 Hz, 1H), 8.08-8.03 (m, 1H), 7.76-7.57 (m, 3H), 7.58-7.50 (m, 2H), 7.29-7.22 (m, 2H), 4.44 (d, J=5.8 Hz, 2H), 2.33-2.14 (m, 3H), 1.81-1.67 (m, 2H), 1.66-1.42 (m, 4H), 1.27-1.09 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 85
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide
Example 85A
2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxamide for 4-nitrobenzoic acid.
Example 85B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting 2,3,4,5-tetrahydro-1H-benzo[d]azepine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.78 (t, J=5.8 Hz, 1H), 8.44 (s, 1H), 7.95 (s, 1H), 7.86 (s, 1H), 7.48-7.56 (m, 2H), 7.08-7.22 (m, 5H), 4.38 (d, J=5.9 Hz, 2H), 3.67-3.78 (m, 4H), 2.89-3.01 (m, 4H); MS (ESI(+)) m/e 402 (M+H) + .
Example 86
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-(3-phenylpyrrolidin-1-yl)-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 85, substituting 3-phenylpyrrolidine for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.75 (dd, J=5.8, 5.6 Hz, 1H), 8.44 (s, 1H), 7.95 (s, 1H), 7.86 (s, 1H), 7.56-7.50 (m, 2H), 7.35-7.31 (m, 2H), 7.29-7.21 (m, 2H), 7.18 (dd, J=8.4, 4.7 Hz, 1H), 4.45 (s, 1H), 4.38 (d, J=5.8 Hz, 2H), 3.92-3.83 (m, 2H), 3.62-3.45 (m, 2H), 2.68-2.62 (m, 1H), 2.42-2.30 (m, 1H), 2.20-2.07 (m, 1H). MS (ESI)(+)) m/e 404 (M+H) + .
Example 87
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutyl)amino]-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 85, substituting 3-methylbutan-1-amine for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.67 (t, J=5.9 Hz, 1H), 8.42 (s, 1H), 8.08 (t, J=5.4 Hz, 1H), 7.94 (s, 1H), 7.71 (s, 1H), 7.49-7.55 (m, 2H), 7.16 (dd, J=9.3, 1.6 Hz, 1H), 4.36 (d, J=5.9 Hz, 2H), 3.17-3.26 (m, 2H), 1.61 (dq, J=6.7 Hz, 1H), 1.41 (q, J=7.0 Hz, 2H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 344 (M+H) + .
Example 88
2-(1,3-dihydro-2H-isoindol-2-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 85, substituting isoindoline for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.81 (t, J=5.9 Hz, 1H), 8.45 (s, 1H), 7.89-7.99 (m, 2H), 7.49-7.56 (m, 2H), 7.37-7.45 (m, 2H), 7.30-7.37 (m, 2H), 7.19 (dd, J=9.3, 1.5 Hz, 1H), 4.76 (s, 4H), 4.40 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 376 (M+H) + .
Example 89
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylcarbamoyl)amino]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.98-8.94 (m, 1H), 8.67 (s, 1H), 8.64 (s, 1H), 7.97-7.93 (m, 1H), 7.54-7.48 (m, 2H), 7.42-7.36 (m, 2H), 7.19-7.12 (m, 2H), 7.08 (dd, J=9.5, 2.1 Hz, 1H), 4.14-3.99 (m, 2H), 2.89-2.56 (m, 3H), 1.77-1.69 (m, 2H), 1.52-1.36 (m, 11H); MS (ESI(+)) m/e 436 (M+H) + .
Example 90
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide
Example 90A
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 90B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 8.75-8.67 (m, 1H), 8.43 (s, 1H), 7.89-7.83 (m, 3H), 7.54-7.43 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.29-6.23 (m, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.19-4.13 (m, 2H), 3.70 (t, J=5.7 Hz, 2H), 2.95-2.84 (m, 1H), 2.57-2.49 (m, 2H), 1.04 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 403 (M+H) + .





TABLE 7



The following Examples were prepared essentially as described in Example 90,

substituting the appropriate carboxylic acid for isobutyric acid in Example 90B.






Ex
Name
1 H NMR
MS








91
4-[1-(2-hydroxy-

(ESI(+))


2-

m/e 419


methylpropanoyl)-

(M + H) +


1,2,3,6-


tetrahydropyridin-


4-yl]-N-


(imidazo[1,2-


a]pyridin-6-


ylmethyl)benzamide

92
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 460


ylmethyl)-4-[1-

(M + H) +


(morpholin-4-


ylacetyl)-1,2,3,6-


tetrahydropyridin-


4-yl]benzamide

93
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 459


ylmethyl)-4-[1-

(M + H) +


(tetrahydro-2H-


pyran-4-ylacetyl)-


1,2,3,6-


tetrahydropyridin-


4-yl]benzamide

94
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 445


ylmethyl)-4-[1-

(M + H) +


(tetrahydrofuran-


3-ylacetyl)-


1,2,3,6-


tetrahydropyridin-


4-yl]benzamide

95
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 445


ylmethyl)-4-[1-

(M + H) +


(tetrahydrofuran-


2-ylacetyl)-


1,2,3,6-


tetrahydropyridin-


4-yl]benzamide

96
N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-

m/e 459


ylmethyl)-4-{1-[3-

(M + H) +


(tetrahydrofuran-


2-yl)propanoyl]-


1,2,3,6-


tetrahydropyridin-


4-yl}benzamide

97
4-[1-
1 H NMR (300 MHz, methanol-d 4 ) δ ppm
(ESI(+))


(cyclopentylacetyl)-
8.81-8.76 (m, 1H), 8.21 (m, 1H),
m/e 443


1,2,3,6-
8.05-7.98 (m, 2H), 7.97-7.79 (m, 3H),
(M + H) +


tetrahydropyridin-
7.59-7.53 (m, 2H), 6.31-6.23 (m, 1H),


4-yl]-N-
4.74-4.65 (m, 2H), 4.29-4.19 (m, 2H),


(imidazo[1,2-
3.85-3.75 (m, 2H), 2.71-2.41 (m, 4H),


a]pyridin-6-
2.33-2.14 (m, 1H), 1.92-1.74 (m, 2H),


ylmethyl)benzamide
1.76-1.49 (m, 4H), 1.32-1.13 (m, 2H)

98
N-(imidazo[1,2-
1 H NMR (300 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-
8.81-8.76 (m, 1H), 8.21 (m, 1H),
m/e 443


ylmethyl)-4-{1-
8.05-7.98 (m, 2H), 7.95-7.83 (m, 3H),
(M + H) +


[(propan-2-
7.61-7.51 (m, 2H), 6.31-6.22 (m, 1H),


yloxy)acetyl]-
4.74-4.68 (m, 2H), 4.32-4.17 (m, 4H),


1,2,3,6-
3.90-3.64 (m, 3H), 2.73-2.53 (m, 2H),


tetrahydropyridin-
1.25-1.16 (m, 6H)


4-yl}benzamide

99
N-(imidazo[1,2-
1 H NMR (300 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-
8.81-8.77 (m, 1H), 8.22-8.20 (m, 1H),
m/e 431


ylmethyl)-4-[1-
8.02-7.99 (m, 2H), 7.97-7.82 (m, 3H),
(M + H) +


(tetrahydrofuran-
7.59-7.53 (m, 2H), 6.31-6.23 (m, 1H),


2-ylcarbonyl)-
4.82-4.74 (m, 1H), 4.70 (s, 2H),


1,2,3,6-
4.40-4.11 (m, 2H), 4.01-3.71 (m, 4H),


tetrahydropyridin-
2.74-2.52 (m, 2H), 2.30-2.17 (m, 1H),


4-yl]benzamide
2.17-1.84 (m, 3H)

100
N-(imidazo[1,2-
1 H NMR (300 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-
8.81-8.77 (m, 1H), 8.24-8.17 (m, 1H),
m/e 431


ylmethyl)-4-[1-
8.05-7.97 (m, 2H), 7.97-7.82 (m, 3H),
(M + H) +


(tetrahydrofuran-
7.59-7.53 (m, 2H), 6.31-6.25 (m, 1H),


3-ylcarbonyl)-
4.72 (s, 2H), 4.35-4.21 (m, 2H),


1,2,3,6-
4.06-3.93 (m, 1H), 3.95-3.76 (m, 5H),


tetrahydropyridin-
3.60-3.42 (m, 1H), 2.71-2.52 (m, 2H),


4-yl]benzamide
2.27-2.02 (m, 2H)

101
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-
8.81-8.78 (m, 1H), 8.23-8.19 (m, 1H),
m/e 828


ylmethyl)-4-[1-
8.05-7.98 (m, 2H), 7.93-7.84 (m, 3H),
(M + H) +


(tetrahydro-2H-
7.59-7.53 (m, 2H), 6.31-6.25 (m, 1H),


pyran-4-
4.70 (s, 2H), 4.36-4.30 (m, 1H),


ylcarbonyl)-
4.25-4.19 (m, 1H), 4.02-3.93 (m, 2H),


1,2,3,6-
3.87-3.78 (m, 2H), 3.59-3.46 (m, 2H),


tetrahydropyridin-
3.10-2.92 (m, 1H), 2.70-2.53 (m, 2H),


4-yl]benzamide
1.91-1.72 (m, 2H), 1.73-1.57 (m, 2H)

102
4-[1-(1,4-dioxan-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


2-ylcarbonyl)-
8.79 (s, 1H), 8.23-8.20 (m, 1H),
m/e 447


1,2,3,6-
8.04-7.99 (m, 2H), 7.93-7.84 (m, 3H),
(M + H) +


tetrahydropyridin-
7.59-7.53 (m, 2H), 6.29-6.23 (m, 1H),


4-yl]-N-
4.73-4.67 (m, 2H), 4.53-4.06 (m, 3H),


(imidazo[1,2-
3.96-3.59 (m, 8H), 2.76-2.53 (m, 2H)


a]pyridin-6-


ylmethyl)benzamide

103
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


a]pyridin-6-
8.79 (s, 1H), 8.24-8.19 (m, 1H), 8.01 (m,
m/e 449


ylmethyl)-4-{1-
2H), 7.97-7.82 (m, 3H), 7.59-7.53 (m,
(M + H) +


[(2-
2H), 6.31-6.23 (m, 1H), 4.76-4.69 (m,


methoxyethoxy)acetyl]-
2H), 4.35-4.26 (m, 2H), 4.25-4.19 (m,


1,2,3,6-
2H), 3.86-3.62 (m, 4H), 3.61-3.54 (m,


tetrahydropyridin-
2H), 3.35 (s, 3H), 2.72-2.54 (m, 2H)


4-yl}benzamide

104
4-(1-benzoyl-
1 H NMR (400 MHz, DMSO-d 6 , Temp = 90° C.)
(ESI(+))


1,2,3,6-
δ ppm 8.89-8.82 (m, 1H), 8.73 (s,
m/e 437


tetrahydropyridin-
1H), 8.22 (d, J = 1.9 Hz, 1H), 7.96 (d, J = 1.9 Hz,
(M + H) +


4-yl)-N-
1H), 7.90-7.75 (m, 4H),


(imidazo[1,2-
7.56-7.49 (m, 2H), 7.49-7.37 (m, 5H),


a]pyridin-6-
6.27 (bs, 1H), 4.58 (d, J = 5.8 Hz, 2H),


ylmethyl)benzamide
4.23-4.17 (m, 2H), 3.72-3.65 (m, 2H),



2.61-2.53 (m, 2H)

105
4-{1-[(4,4-
1 H NMR (400 MHz, DMSO-d 6 , Temp = 90° C.)
(ESI(+))


difluorocyclohexyl)carbonyl]-
δ ppm 8.90-8.83 (m, 1H), 8.74 (s,
m/e 479


1,2,3,6-
1H), 8.22 (d, J = 1.9 Hz, 1H), 7.97 (d, J = 1.9 Hz,
(M + H) +


tetrahydropyridin-
1H), 7.90-7.75 (m, 4H),


4-yl}-N-
7.54-7.48 (m, 2H), 6.30-6.24 (m, 1H),


(imidazo[1,2-
4.58 (d, J = 5.8 Hz, 2H), 4.21-4.15 (m, 2H),


a]pyridin-6-
3.77-3.69 (m, 2H), 2.91-2.79 (m, 1H),


ylmethyl)benzamide
2.58-2.51 (m, 2H), 2.12-2.00 (m, 2H),



2.00-1.59 (m, 6H)


















































































































































Example 106
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea
Example 106A
1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(piperidin-4-yl)phenyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 106B
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-6-yl)-3-(4-(piperidin-4-yl)phenyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 8.86-8.81 (m, 1H), 8.41 (s, 1H), 8.38 (s, 1H), 7.86 (s, 1H), 7.50-7.42 (m, 2H), 7.40-7.34 (m, 2H), 7.18-7.12 (m, 2H), 7.12-7.06 (m, 1H), 4.41-4.18 (m, 2H), 2.95-2.64 (m, 4H), 1.87-1.78 (m, 2H), 1.56-1.38 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 406 (M+H) + .
Example 108
2-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(imidazo[1,2-a]pyridin-6-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 85, substituting 1,2,3,4-tetrahydroisoquinoline for 2,3,4,5-tetrahydro-1H-benzo[d]azepine in Example 85B. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.81 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.98 (s, 1H), 7.89 (s, 1 H), 7.48-7.63 (m, 2H), 7.13-7.32 (m, 5H), 4.65 (s, 2H), 4.39 (d, J=5.9 Hz, 2H), 3.73 (t, J=6.0 Hz, 2H), 2.94 (t, J=6.0 Hz, 2H); MS (ESI(+)) m/e 390 (M+H) + .
Example 109
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 106, substituting tetrahydro-2H-pyran-4-carboxylic acid for isobutyric acid in Example 106B. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.37-9.33 (m, 1H), 8.22-8.17 (m, 1H), 7.97 (d, J=2.1 Hz, 1H), 7.89-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.24-7.18 (m, 2H), 4.73-4.64 (m, 1H), 4.25-4.15 (m, 1H), 4.01-3.93 (m, 2H), 3.57-3.46 (m, 2H), 3.27-3.17 (m, 1H), 3.06-2.95 (m, 1H), 2.87-2.66 (m, 2H), 2.00-1.70 (m, 4H), 1.70-1.48 (m, 4H); MS (ESI(+)) m/e 448 (M+H) + .
Example 110
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-3-ylacetyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 106, substituting 2-(tetrahydrofuran-3-yl)acetic acid for isobutyric acid in Example 106B. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.37-9.32 (m, 1H), 8.21-8.17 (m, 1H), 7.97 (d, J=2.1 Hz, 1H), 7.88-7.76 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.18 (m, 2H), 4.71-4.62 (m, 1H), 4.14-4.05 (m, 1H), 3.95-3.82 (m, 2H), 3.81-3.70 (m, 1H), 3.47-3.35 (m, 1H), 3.25-3.12 (m, 1H), 2.86-2.48 (m, 5H), 2.22-2.07 (m, 1H), 1.95-1.83 (m, 2H), 1.74-1.46 (m, 3H); MS (ESI(+) m/e 448 (M+H) + .
Example 111
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 106, substituting 2-(tetrahydrofuran-2-yl)acetic acid for isobutyric acid in Example 106B. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.37-9.32 (m, 1H), 8.21-8.17 (m, 1H), 7.99-7.95 (m, 1H), 7.88-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.17 (m, 2H), 4.73-4.63 (m, 1H), 4.33-4.20 (m, 1H), 4.19-4.10 (m, 1H), 3.92-3.83 (m, 1H), 3.79-3.69 (m, 1H), 3.26-3.14 (m, 1H), 2.87-2.65 (m, 3H), 2.63-2.47 (m, 1H), 2.19-2.06 (m, 1H), 2.01-1.81 (m, 4H), 1.77-1.50 (m, 3H); MS (ESI(+)) m/e 448 (M+H) + .
Example 112
1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-imidazo[1,2-a]pyridin-6-ylurea
The title compound was prepared as described in Example 106, substituting benzoic acid for isobutyric acid in Example 106B. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.87-8.81 (m, 1H), 8.38 (bs, 1H), 8.38 (bs, 1H), 7.86 (s, 1H), 7.51-7.34 (m, 9H), 7.21-7.14 (m, 2H), 7.09 (dd, J=9.5, 2.0 Hz, 1H), 4.34-3.97 (m, 2H), 3.08-2.95 (m, 2H), 2.83-2.71 (m, 1H), 1.85-1.77 (m, 2H), 1.66-1.50 (m, 2H); MS (ESI(+)) m/e 440 (M+H) + .
Example 113
1-imidazo[1,2-a]pyridin-6-yl-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 106, substituting tetrahydrofuran-2-carboxylic acid for isobutyric acid in Example 106B. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.38-9.33 (m, 1H), 8.21-8.16 (m, 1H), 8.00-7.95 (m, 1H), 7.88-7.77 (m, 2H), 7.44-7.38 (m, 2H), 7.23-7.17 (m, 2H), 4.83-4.73 (m, 1H), 4.69-4.60 (m, 1H), 4.22-4.11 (m, 1H), 4.01-3.90 (m, 1H), 3.91-3.82 (m, 1H), 3.26-3.12 (m, 1H), 2.87-2.68 (m, 2H), 2.31-2.14 (m, 1H), 2.12-1.75 (m, 5H), 1.77-1.50 (m, 2H); MS (ESI(+)) m/e 434 (M+H) + .
Example 114
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.40 (s, 1H), 7.86-7.79 (m, 3H), 7.52 (t, J=5.4 Hz, 2H), 7.34 (dd, J=9.3, 1.7 Hz, 1H), 7.06-6.99 (m, 2H), 4.72-4.60 (m, 1H), 4.56 (s, 2H), 3.77-3.65 (m, 2H), 3.41-3.30 (m, 2H), 2.03-1.90 (m, 2H), 1.76-1.59 (m, 2H), 1.46 (s, 9H); MS (ESI(+)) m/e 451 (M+H) + .
Example 115
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide
Example 115A
2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
Example 115B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-((tetrahydrofuran-2-yl)methylamino)thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting (tetrahydrofuran-2-yl)methanamine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide.
Example 115C
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[{[2-(propan-2-yloxy)ethyl]carbamoyl}(tetrahydrofuran-2-ylmethyl)amino]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1C, substituting 2-isopropoxyethanamine for 4-amino-N-isopentylbenzamide and N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-((tetrahydrofuran-2-yl)methylamino)thiazole-5-carboxamide for imidazo[1,2-a]pyridin-6-amine 1 H NMR (400 MHz, CDCl 3 ) δ ppm 8.52 (s, 1H), 8.21 (d, J=9.0 Hz, 1H), 7.96 (s, 1H), 7.89 (d, J=1.5 Hz, 1H), 7.86-7.80 (m, 1H), 7.78 (d, J=9.5 Hz, 1H), 7.73 (s, 1H), 6.96-6.86 (m, 1H), 4.74-4.60 (m, 2H), 4.50-4.38 (m, 1H), 4.26 (ddd, J=4.4, 2.2, 0.6 Hz, 1H), 4.07-3.90 (m, 2H), 3.85-3.74 (m, 1H), 3.63 (dd, J=12.2, 6.1 Hz, 1H), 3.60-3.53 (m, 2H), 3.53-3.41 (m, 2H), 1.95 (dd, J=7.8, 6.9 Hz, 3H), 1.63-1.56 (m, 1H), 1.18 (dd, J=6.1, 1.2 Hz, 6H); (APCI(+)) m/e 487 (M+H) + .





TABLE 8



The following Examples were prepared essentially as described in Example

115, substituting the appropriate amine in Example 115B and the appropriate

amine for 2-isopropoxyethanamine in Example 115C.






Ex
Name
1 H NMR
MS



138
N-(imidazo[1,2-
1 H NMR (400 MHz, CDCl 3 ) δ ppm 8.09
(APCI(+))


a]pyridin-7-
(d, J = 7.0 Hz, 1H), 7.86 (d, J = 14.0 Hz,
m/e 459


ylmethyl)-2-{[(2-
2H), 7.62 (d, J = 0.8 Hz, 1H), 7.54 (d, J =
(M + H)+


methoxyethyl)
9.1 Hz, 2H), 6.84 (dd, J = 7.0, 1.4 Hz,



carbamoyl]
1H), 6.27 (t, J = 5.8 Hz, 1H), 4.63 (d, J =



(tetrahydrofuran-2-
6.0 Hz, 2H), 4.44 (d, J = 14.3 Hz, 1H),



ylmethyl)amino}-
4.29 (q, J = 7.3 Hz, 1H), 4.05 (dd, J =



1,3-thiazole-5-
15.4, 7.2 Hz, 1H), 3.92 (dd, J = 15.2, 7.2



carboxamide
Hz, 1H), 3.86-3.72 (m, 1H), 3.58-




3.51 (m, 2H), 3.48 (dd, J = 9.2, 3.8 Hz,




3H), 3.39 (s, 3H), 2.14 (dt, J = 12.4, 6.3




Hz, 1H), 2.05-1.86 (m, 2H)


141
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz,
m/e 459


ylmethyl)-2-{[(2-
1H), 8.03 (d, J = 2.1 Hz, 1H), 7.99 (d, J =
(M + H) +


methoxyethyl)
9.8 Hz, 2H), 7.91 (d, J = 9.3 Hz, 1H),



carbamoyl]
4.65 (s, 2H), 4.24 (dd, J = 15.2, 7.6 Hz,



(tetrahydrofuran-3-
1H), 4.12 (dd, J = 15.2, 7.9 Hz, 1H),



ylmethyl)amino}-
3.93 (td, J = 8.1, 5.8 Hz, 1H), 3.79-



1,3-thiazole-5-
3.67 (m, 2H), 3.60 (dd, J = 8.7, 5.2 Hz,



carboxamide
1H), 3.55-3.45 (m, 4H), 3.36 (s, 3H),




2.85-2.75 (m, 1H), 2.00 (td, J = 13.4,




7.8 Hz, 1H), 1.72 (dt, J = 20.1, 6.3 Hz,




1H)


151
N-(imidazo[1,2-
1 H NMR (500 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.77 (s, 1H), 8.21 (d, J = 2.0 Hz,
m/e 473


ylmethyl)-2-{[(2-
1H), 8.02 (d, J = 2.1 Hz, 1H), 7.99 (dd,
(M + H) +


methoxyethyl)
J = 9.3, 1.4 Hz, 1H), 7.97 (s, 1H), 7.90



carbamoyl]
(d, J = 9.3 Hz, 1H), 4.65 (s, 2H), 4.07



(tetrahydro-
(d, J = 7.6 Hz, 2H), 3.92 (dd, J = 11.5,



2H-pyran-4-
3.0 Hz, 2H), 3.52 (dd, J = 8.3, 3.1 Hz,



ylmethyl)amino}-
2H), 3.47 (dd, J = 8.1, 3.0 Hz, 2H), 3.36



1,3-thiazole-5-
(s, 3H), 3.36-3.32 (m, 2H), 2.14 (ddd,



carboxamide
J = 15.4, 7.7, 3.8 Hz, 1H), 1.54 (d, J =




11.2 Hz, 2H), 1.42 (qd, J = 12.1, 4.4 Hz,




2H)


152
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz,
m/e 501


ylmethyl)-2-[{[2-
1H), 8.03 (d, J = 2.1 Hz, 1H), 8.01-
(M + H) +


(propan-2-
7.97 (m, 2H), 7.91 (d, J = 9.3 Hz, 1H),



yloxy)ethyl]
4.65 (s, 2H), 4.06 (d, J = 7.6 Hz, 2H),



carbamoyl}(tetra-
3.92 (dd, J = 11.4, 3.0 Hz, 2H), 3.63 (dt,



hydro-2H-pyran-4-
J = 12.2, 6.1 Hz, 1H), 3.57 (dd, J = 10.1,



ylmethyl)amino]-
4.5 Hz, 2H), 3.45 (t, J = 5.5 Hz, 2H),



1,3-thiazole-5-
3.35 (dd, J = 11.6, 1.7 Hz, 2H), 2.16



carboxamide
(ddd, J = 11.4, 7.6, 3.8 Hz, 1H), 1.55




(dd, J = 12.6, 1.5 Hz, 2H), 1.42 (qd, J =




12.1, 4.4 Hz, 2H), 1.16 (d, J = 6.1 Hz,




6H)


153
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.70 (s, 1H), 8.14 (d, J = 2.1 Hz,
m/e 459


ylmethyl)-2-{[(2-
1H), 7.95 (d, J = 2.2 Hz, 1H), 7.91 (dd,
(M + H) +


methoxyethyl)
J = 9.4, 1.5 Hz, 1H), 7.88 (s, 1H), 7.82



carbamoyl][(2R)-
(d, J = 9.3 Hz, 1H), 4.57 (s, 2H), 4.33



tetrahydrofuran-2-
(dd, J = 15.4, 1.8 Hz, 1H), 4.17 (dd, J =



ylmethyl]amino}-
11.3, 4.9 Hz, 1H), 4.00 (dd, J = 15.4, 7.7



1,3-thiazole-5-
Hz, 1H), 3.86 (dd, J = 15.2, 7.0 Hz, 1H),



carboxamide
3.71 (td, J = 7.8, 5.8 Hz, 1H), 3.52-




3.39 (m, 2H), 3.38-3.32 (m, 2H), 3.30




(s, 3H), 2.11-1.95 (m, 1H), 1.95-1.77




(m, 2H), 1.66-1.48 (m, 1H), 0.99-




0.87 (m, 1H)


154
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.77 (s, 1H), 8.21 (d, J = 2.1 Hz,
m/e 487


ylmethyl)-2-({[2-
1H), 8.02 (d, J = 2.1 Hz, 1H), 7.98 (dd,
(M + H) +


(propan-2-
J = 9.4, 1.2 Hz, 1H), 7.96 (s, 1H), 7.90



yloxy)ethyl]
(d, J = 9.3 Hz, 1H), 4.64 (s, 2H), 4.41



carbamoyl}[(2R)-
(dd, J = 15.4, 1.6 Hz, 1H), 4.29-4.21



tetrahydrofuran-2-
(m, 1H), 4.07 (dd, J = 15.4, 7.6 Hz, 1H),



ylmethyl]amino)-
3.96 (dd, J = 15.0, 7.1 Hz, 1H), 3.77



1,3-thiazole-5-
(dd, J = 14.0, 7.7 Hz, 1H), 3.64 (dt, J =



carboxamide
12.2, 6.1 Hz, 1H), 3.57 (t, J = 5.0 Hz,




2H), 3.41 (t, J = 5.3 Hz, 2H), 2.15-




2.03 (m, 1H), 2.00-1.87 (m, 2H), 1.64




(dq, J = 12.4, 8.2 Hz, 1H), 1.16 (d, J =




6.1 Hz, 6H)


155
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.78 (s, 1H), 8.21 (d, J = 2.1 Hz,
m/e 459


ylmethyl)-2-{[(2-
1H), 8.03 (d, J = 2.1 Hz, 1H), 8.01-
(M + H) +


methoxyethyl)
7.97 (m, 1H), 7.96 (s, 1H), 7.90 (d, J =



carbamoyl][(2S)-
9.3 Hz, 1H), 4.64 (s, 2H), 4.41 (d, J =



tetrahydrofuran-2-
15.4 Hz, 1H), 4.26 (q, J = 6.4 Hz, 1H),



ylmethyl]amino}-
4.08 (dd, J = 15.4, 7.7 Hz, 1H), 3.94



1,3-thiazole-5-
(dd, J = 15.1, 7.1 Hz, 1H), 3.79 (dd, J =



carboxamide
13.7, 7.7 Hz, 1H), 3.53 (dt, J = 7.4, 4.5




Hz, 2H), 3.43 (t, J = 5.2 Hz, 2H), 3.38




(s, 3H), 2.11 (td, J = 12.3, 7.2 Hz, 1H),




2.01-1.85 (m, 2H), 1.65 (dq, J = 12.2,




8.2 Hz, 1H)


156
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.78 (s, 1H), 8.22 (d, J = 2.1 Hz,
m/e 487


ylmethyl)-2-({[2-
1H), 8.03 (d, J = 2.1 Hz, 1H), 7.99 (dd,
(M + H) +


(propan-2-
J = 9.3, 1.4 Hz, 1H), 7.96 (s, 1H), 7.91



yloxy)ethyl]
(d, J = 9.3 Hz, 1H), 4.65 (s, 2H), 4.41



carbamoyl}[(2S)-
(dd, J = 15.4, 1.8 Hz, 1H), 4.31-4.22



tetrahydrofuran-2-
(m, 1H), 4.08 (dd, J = 15.4, 7.6 Hz, 1H),



ylmethyl]amino)-
3.96 (dd, J = 15.1, 7.0 Hz, 1H), 3.78



1,3-thiazole-5-
(dd, J = 14.0, 7.7 Hz, 1H), 3.65 (dt, J =



carboxamide
12.1, 6.1 Hz, 1H), 3.57 (t, J = 4.9 Hz,




2H), 3.41 (t, J = 5.3 Hz, 2H), 2.11 (td, J =




12.2, 7.1 Hz, 1H), 2.01-1.85 (m,




2H), 1.65 (dq, J = 12.3, 8.2 Hz, 1H),




1.17 (d, J = 6.1 Hz, 6H)


157
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-6-
ppm 8.78 (s, 1H), 8.21 (d, J = 2.0 Hz,
m/e 487


ylmethyl)-2-[{[2-
1H), 8.03 (d, J = 2.1 Hz, 1H), 7.99 (d, J =
(M + H) +


(propan-2-
11.6 Hz, 2H), 7.90 (d, J = 9.4 Hz, 1H),



yloxy)ethyl]
4.65 (d, J = 3.9 Hz, 2H), 4.24 (dd, J =



carbamoyl}
15.2, 7.6 Hz, 1H), 4.12 (dd, J = 15.1, 8.0



(tetrahydrofuran-3-
Hz, 1H), 3.94 (td, J = 8.1, 5.7 Hz, 1H),



ylmethyl)amino]-
3.79-3.67 (m, 2H), 3.63 (dt, J = 8.2,



1,3-thiazole-5-
4.7 Hz, 2H), 3.57 (t, J = 5.8 Hz, 2H),



carboxamide
3.51-3.41 (m, 2H), 2.89-2.76 (m,




1H), 2.00 (td, J = 13.3, 7.9 Hz, 1H),




1.73 (dt, J = 20.3, 6.4 Hz, 1H), 1.15 (d,




J = 6.1 Hz, 6H)










































































































































Example 116
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide
Example 116A
2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
Example 116B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[2-oxo-4-(tetrahydrofuran-3-yl)-1,3-oxazolidin-3-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting 4-(tetrahydrofuran-3-yl)oxazolidin-2-one for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1 H NMR (400 MHz, methanol-d 4 ) δ 8.79 (s, 1H), 8.22 (d, J=1.9 Hz, 1H), 8.03 (s, 2H), 8.01-7.97 (m, 1H), 7.91 (d, J=9.5 Hz, 1H), 4.98-4.92 (m, 1H), 4.64 (dt, J=8.6, 4.5 Hz, 3H), 4.57-4.49 (m, 1H), 3.97 (td, J=8.5, 3.9 Hz, 1H), 3.81-3.71 (m, 1H), 3.71-3.59 (m, 2H), 2.26-2.02 (m, 1H), 1.96-1.85 (m, 1H), 1.78-1.65 (m, 1H); (APCI(+)) m/e 414 (M+H) + .





TABLE 9



The following Examples were prepared essentially as described in

Example 116, substituting the appropriate amine in Example 116A

and the appropriate amine in Example 116B.






Ex
Name
1H NMR
MS








12
2N-(imidazo[1,2-

(ESI(+))


a]pyridin-6-ylmethyl)-

m/e 420


2-(2-oxo-5-phenyl-

(M + H) +


1,3-oxazolidin-3-yl)-




1,3-thiazole-5-




carboxamide



158
2-[5-(4-

(ESI(+))


chlorophenyl)-2-oxo-

m/e 454


1,3-oxazolidin-3-yl]-

(M + H) +


N-(imidazo[1,2-




a]pyridin-6-ylmethyl)-




1,3-thiazole-5-




carboxamide



181
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
ppm 8.39 (d, J = 7.0 Hz, 1H), 8.04
m/e 386


2-[(4R)-2-oxo-4-
(s, 1H), 7.80 (s, 1H), 7.53 (s, 1H),
(M + H) +


(propan-2-yl)-1,3-
7.45 (s, 1H), 6.97-6.87 (m, 1H),



oxazolidin-3-yl]-1,3-
4.75 (dt, J = 7.7, 3.8 Hz, 1H), 4.52



thiazole-5-
(dd, J = 9.5, 6.3 Hz, 2H), 2.85-2.65



carboxamide
(m, 1H), 0.99 (d, J = 7.1 Hz, 3H),




0.84 (d, J = 6.9 Hz, 3H)


185
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
ppm 9.26 (t, J = 5.5 Hz, 1H), 8.75
m/e 386


2-[(4S)-2-oxo-4-
(d, J = 7.0 Hz, 1H), 8.18 (d, J = 2.1
(M + H) +


(propan-2-yl)-1,3-
Hz, 1H), 8.07 (s, 1H), 8.00 (d, J =



oxazolidin-3-yl]-1,3-
2.1 Hz, 1H), 7.81 (s, 1H), 7.48 (d,



thiazole-5-
J = 7.0 Hz, 1H), 4.77 (dd, J = 7.7,



carboxamide
3.9 Hz, 1H), 4.55 (dd, J = 10.7, 6.3




Hz, 2H), 2.76 (qd, J = 10.6, 7.1 Hz,




1H), 1.00 (d, J = 7.1 Hz, 3H), 0.84




(d, J = 6.9 Hz, 3H)


187
2-{(4R)-4-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


[(benzyloxy)methyl]-
ppm 8.40 (d, J = 7.0 Hz, 1H), 7.91
m/e 464


2-oxo-1,3-oxazolidin-
(s, 1H), 7.80 (s, 1H), 7.53 (s, 1H),
(M + H) +


3-yl}-N-(imidazo[1,2-
7.46 (s, 1H), 7.20 (ddd, J = 15.4,



a]pyridin-7-ylmethyl)-
11.1, 5.1 Hz, 5H), 6.93 (dd, J = 7.0,



1,3-thiazole-5-
1.3 Hz, 1H), 4.85 (dd, J = 6.1, 2.6



carboxamide
Hz, 1H), 4.67-4.52 (m, 5H), 4.41




(d, J = 12.2 Hz, 1H), 4.12 (dd, J =




10.2, 3.2 Hz, 1H), 3.63 (dd, J = 10.2,




1.6 Hz, 1H)


188
2-{(4S)-4-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


[(benzyloxy)methyl]-
ppm 8.35 (d, J = 7.0 Hz, 1H), 7.87
m/e 464


2-oxo-1,3-oxazolidin-
(s, 1H), 7.75 (s, 1H), 7.48 (s, 1H),
(M + H) +


3-yl}-N-(imidazo[1,2-
7.42 (s, 1H), 7.16 (ddd, J = 19.3,



a]pyridin-7-ylmethyl)-
11.3, 5.0 Hz, 5H), 6.88 (dd, J = 7.0,



1,3-thiazole-5-
1.3 Hz, 1H), 4.83-4.75 (m, 1H),



carboxamide
4.62-4.47 (m, 5H), 4.36 (d, J =




12.2 Hz, 1H), 4.07 (dd, J = 10.2, 3.2




Hz, 1H), 3.59 (dd, J = 10.2, 1.6 Hz,




1H)


218
2-{5-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


[(benzyloxy)methyl]-
ppm 8.39 (d, J = 7.0 Hz, 1H), 8.03
m/e 464


2-oxo-1,3-oxazolidin-
(s, 1H), 7.79 (s, 1H), 7.53 (s, 1H),
(M + H) +


3-yl}-N-(imidazo[1,2-
7.45 (s, 1H), 7.36-7.18 (m, 5H),



a]pyridin-7-ylmethyl)-
6.92 (d, J = 5.6 Hz, 1H), 5.02-4.99



1,3-thiazole-5-
(m, 2H), 4.59 (d, J = 2.3 Hz, 6H),



carboxamide
3.76 (ddd, J = 14.8, 11.2, 3.2 Hz,




1H)


244
2-[(2S)-2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


(hydroxymethyl)-5-
ppm 9.25 (t, J = 5.7 Hz, 1H), 8.75
m/e 372


oxopyrrolidin-1-yl]-
(d, J = 7.0 Hz, 1H), 8.18 (d, J = 1.9
(M + H) +


N-(imidazo[1,2-
Hz, 1H), 8.10 (s, 1H), 8.00 (d, J =



a]pyridin-7-ylmethyl)-
2.1 Hz, 1H), 7.81 (s, 1H), 7.48 (dd,



1,3-thiazole-5-
J = 7.1, 1.3 Hz, 1H), 4.75-4.69 (m,



carboxamide
3H), 4.17 (dd, J = 11.7, 3.4 Hz, 1H),




3.75 (dd, J = 11.7, 2.2 Hz, 1H), 2.88




(dt, J = 17.8, 10.1 Hz, 1H), 2.57




(ddd, J = 17.7, 10.1, 2.3 Hz, 1H),




2.48-2.33 (m, 1H), 2.33-2.18 (m,




1H)


245
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
ppm 8.75 (d, J = 7.0 Hz, 1H), 8.18
m/e 358


2-[(4R)-4-methyl-2-
(d, J = 2.0 Hz, 1H), 8.07 (s, 1H),
(M + H) +


oxo-1,3-oxazolidin-3-
8.00 (t, J = 2.4 Hz, 1H), 7.81 (s,



yl]-1,3-thiazole-5-
1H), 7.48 (dd, J = 7.0, 1.4 Hz, 1H),



carboxamide
4.87-4.78 (m, 1H), 4.73 (s, 2H),




4.69 (t, J = 8.5 Hz, 1H), 4.25 (dd,




J = 8.7, 3.9 Hz, 1H), 1.57 (d, J = 6.3




Hz, 3H)


249
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
ppm 9.26 (t, J = 5.9 Hz, 1H), 8.75
m/e 416


2-{2-oxo-5-[(propan-
(d, J = 7.0 Hz, 1H), 8.18 (d, J = 2.0
(M + H) +


2-yloxy)methyl]-1,3-
Hz, 1H), 8.06 (s, 1H), 8.00 (d, J =



oxazolidin-3-yl}-1,3-
2.1 Hz, 1H), 7.81 (s, 1H), 7.48 (d,



thiazole-5-
J = 7.0 Hz, 1H), 4.98 (ddd, J = 9.1,



carboxamide
5.8, 2.9 Hz, 1H), 4.73 (s, 2H), 4.31




(t, J = 9.5 Hz, 1H), 4.14 (dd, J = 9.9,




5.6 Hz, 1H), 3.78 (dd, J = 11.2, 2.9




Hz, 1H), 3.73-3.60 (m, 2H), 1.13




(d, J = 6.1 Hz, 6H)


251
2-[5-
1 H NMR (400 MHz, DMSO-d 6 ) 6
(APCI(+))


(hydroxymethyl)-2-
ppm 9.17 (t, J = 6.2 Hz, 1H), 8.50
m/e 374


oxo-1,3-oxazolidin-3-
(d, J = 6.9 Hz, 1H), 8.14 (s, 1H),
(M + H) +


yl]-N-(imidazo[1,2-
7.90 (s, 1H), 7.53 (s, 1H), 7.41 (s,



a]pyridin-7-ylmethyl)-
1H), 6.85 (d, J = 6.9 Hz, 1H), 5.29



1,3-thiazole-5-
(t, J = 5.6 Hz, 1H), 4.93-4.84 (m,



carboxamide
1H), 4.47 (d, J = 5.8 Hz, 2H), 4.24




(t, J = 9.4 Hz, 1H), 4.00 (dd, J = 9.8,




5.8 Hz, 1H), 3.76-3.66 (m, 1H),




3.66-3.56 (m, 1H)


255
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
8.40 (d, J = 7.0 Hz, 1H), 8.04 (s,
m/e 416


2-{(5S)-2-oxo-5-
1H), 7.80 (s, 1H), 7.53 (s, 1H), 7.45
(M + H) +


[(propan-2-
(s, 1H), 6.92 (d, J = 6.3 Hz, 1H),



yloxy)methyl]-1,3-
5.01-4.94 (m, 1H), 4.59 (s, 2H),



oxazolidin-3-yl}-1,3-
4.31 (t, J = 9.5 Hz, 1H), 4.13 (dd, J =



thiazole-5-
9.9, 5.6 Hz, 1H), 3.77 (dd, J=



carboxamide
11.2, 3.0 Hz, 1H), 3.72-3.58 (m,




2H), 1.13 (d, J = 6.1 Hz, 6H)


256
N-(imidazo[1,2-
1 H NMR (400 MHz, methanol-d 4 ) δ
(APCI(+))


a]pyridin-7-ylmethyl)-
ppm 8.40 (d, J = 7.0 Hz, 1H), 8.04
m/e 416


2-{(5R)-2-oxo-5-
(s, 1H), 7.80 (s, 1H), 7.53 (s, 1H),
(M + H)+


[(propan-2-
7.45 (s, 1H), 6.92 (d, J = 7.0 Hz,



yloxy)methyl]-1,3-
1H), 5.03-4.95 (m, 1H), 4.59 (s,



oxazolidin-3-yl}-1,3-
2H), 4.31 (t, J = 9.5 Hz, 1H), 4.13



thiazole-5-
(dd, J = 9.9, 5.7 Hz, 1H), 3.77 (dd,



carboxamide
J = 11.2, 3.0 Hz, 1H), 3.71-3.58 (m,




2H), 1.13 (d, J = 6.1 Hz, 6H)
















































































































































Example 117
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.09 (s, 1H), 9.00-8.93 (m, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.82 (m, 3H), 7.71-7.65 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.40-7.35 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 2.37-2.31 (m, 2H), 2.31-2.16 (m, 1H), 1.81-1.68 (m, 2H), 1.67-1.44 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 118
2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide
Example 118A
2-cyclopentyl-N-(4-nitrophenyl)acetamide
The title compound was prepared as described in Example 1A, substituting 4-nitroaniline for 3-methylbutan-1-amine and 2-cyclopentylacetic acid for 4-nitrobenzoic acid.
Example 118B
N-(4-aminophenyl)-2-cyclopentylacetamide
The title compound was prepared as described in Example 1B, substituting 2-cyclopentyl-N-(4-nitrophenyl)acetamide for N-isopentyl-4-nitrobenzamide.
Example 118C
2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide
The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.76-8.69 (m, 1H), 8.16 (dd, J=2.2, 0.8 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.81-7.77 (m, 1H), 7.49-7.41 (m, 3H), 7.36-7.30 (m, 2H), 4.59 (s, 2H), 2.37-2.24 (m, 3H), 1.90-1.77 (m, 2H), 1.75-1.52 (m, 4H), 1.32-1.18 (m, 2H); MS (ESI(+)) m/e 392 (M+H) + .
Example 119
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide
The title compound was prepared as described in Example 51A, substituting 4-bromo-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.18 (t, J=5.7 Hz, 1H), 8.75 (s, 1H), 8.28 (s, 2H), 8.02 (d, J=1.5 Hz, 1H), 7.97 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.83-7.88 (m, 1H), 7.74-7.80 (m, 1H), 7.69 (d, J=8.3 Hz, 2H), 4.56 (d, J=5.7 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.13 (dq, J=13.6, 6.8 Hz, 1H), 0.85 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 374 (M+H) + .
Example 137
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide
Example 137A
2-(3-methylbutanamido)thiazole-5-carboxylic acid
The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and methyl 2-aminothiazole-5-carboxylate for methyl 4-aminobenzoate.
Example 137B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-2-[(3-methylbutanoyl)amino]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 2-(3-methylbutanamido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 12.31 (s, 1H), 9.05 (t, J=5.7 Hz, 1H), 8.54 (s, 1H), 7.97-8.11 (m, 2H), 7.56-7.71 (m, 2H), 7.34 (d, J=9.2 Hz, 1H), 4.44 (d, J=5.7 Hz, 2H), 2.33 (d, J=7.2 Hz, 2H), 2.07 (dq, J=13.6, 6.7, 6.6 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 358 (M+H) + .
Example 159
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide
Example 159A
tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenoxy)piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid.
Example 159B
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(piperidin-4-yloxy)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)phenoxy)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 159C
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(piperidin-4-yloxy)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.79-8.74 (m, 1H), 8.23-8.19 (m, 1H), 8.04-7.97 (m, 2H), 7.94-7.81 (m, 3H), 7.09-7.03 (m, 2H), 4.81-4.72 (m, 1H), 4.69 (s, 2H), 3.91-3.77 (m, 2H), 3.62-3.48 (m, 2H), 3.04-2.92 (m, 1H), 2.12-1.86 (m, 2H), 1.87-1.61 (m, 2H), 1.11 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 421 (M+H) + .





TABLE 10



The following Examples were prepared essentially as described in

Example 159, substituting the appropriate amine in Example 159A and

the appropriate carboxylic acid in Example 159C.






Ex
Name
1 H NMR
MS



160
4-[(1-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


acetyl-
8.80-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 393


piperidin-
Hz, 1H), 8.04-7.97 (m, 2H), 7.94-7.79
(M + H) +


4-yl)oxy]-N-
(m, 3H), 7.09-7.03 (m, 2H), 4.78-4.70



(imidazo[1,2-
(m, 1H), 4.69 (s, 2H), 3.88-3.69 (m, 2H),



a]pyridin-6-
3.59-3.45 (m, 2H), 2.12 (s, 3H), 2.09-



ylmethyl)
1.91 (m, 2H), 1.86-1.63 (m, 2H)



benzamide



161
4-{[1-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


(cyclopropyl
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 419


carbonyl)
Hz, 1H), 8.04-7.97 (m, 2H), 7.93-7.82
(M + H) +


piperidin-4-
(m, 3H), 7.10-7.04 (m, 2H), 4.81-4.73



yl]oxy}-N-
(m, 1H), 4.69 (s, 2H), 4.07-3.97 (m, 1H),



(imidazo[1,2-
3.92-3.81 (m, 1H), 3.78-3.67 (m, 1H),



a]pyridin-6-
3.57-3.48 (m, 1H), 2.13-1.92 (m, 3H),



ylmethyl)
1.88-1.65 (m, 2H), 0.91-0.78 (m, 4H)



benzamide



162
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.77 (m, 1H), 8.23-8.19 (m, 1H), 8.04-
m/e 463


pyridin-6-
7.97 (m, 2H), 7.94-7.82 (m, 3H), 7.09-
(M + H) +


ylmethyl)-4-
7.03 (m, 2H), 4.75 (m, 1H), 4.69 (s, 2H),



{[1-(tetra-
4.00-3.88 (m, 2H), 3.89-3.80 (m, 2H),



hydro-2H-
3.63-3.45 (m, 4H), 3.04-2.93 (m, 1H),



pyran-4-
2.11-1.92 (m, 2H), 1.86-1.65 (m, 4H),



ylcarbonyl)
1.66-1.58 (m, 2H)



piperidin-4-




yl]oxy}




benzamide



163
4-{[1-(1,4-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


dioxan-2-
8.79-8.75 (m, 1H), 8.23-8.19 (m, 1H),
m/e 465


ylcarbonyl)
8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H),
(M + H) +


piperidin-4-
7.09-7.02 (m, 2H), 4.79-4.71 (m, 1H),



yl]oxy}-N-
4.69 (s, 2H), 4.47-4.39 (m, 1H), 3.99-



(imidazo[1,2-
3.57 (m, 9H), 3.56-3.37 (m, 1H), 2.11-



a]pyridin-6-
1.88 (m, 2H), 1.90-1.62 (m, 2H)



ylmethyl)




benzamide



164
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.79-8.76 (m, 1H), 8.23-8.19 (m, 1H),
m/e 449


pyridin-
8.04-7.97 (m, 2H), 7.94-7.82 (m, 3H),
(M + H) +


6-ylmethyl)-
7.09-7.03 (m, 2H), 4.79-4.71 (m, 2H),



4-({1-[(2S)-
4.69 (s, 2H), 3.98-3.72 (m, 4H), 3.66-



tetrahydro-
3.43 (m, 2H), 2.26-2.13 (m, 1H), 2.13-



furan-2-
1.86 (m, 5H), 1.88-1.65 (m, 2H)



ylcarbonyl]




piperidin-4-




yl}oxy)




benzamide



165
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.79-8.75 (m, 1H), 8.23-8.19 (m, 1H),
m/e 449


pyridin-
8.04-7.97 (m, 2H), 7.93-7.82 (m, 3H),
(M + H) +


6-ylmethyl)-
7.09-7.03 (m, 2H), 4.79-4.71 (m, 1H),



4-({1-[(2R)-
4.69 (s, 1H), 4.00-3.71 (m, 4H), 3.67-



tetrahydro-
3.43 (m, 1H), 2.26-2.13 (m, 1H), 2.13-



furan-2-
1.86 (m, 5H), 1.88-1.65 (m, 2H)



ylcarbonyl]




piperidin-4-




ylloxy)




benzamide



166
4-{[1-(2-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


hydroxy-2-
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 437


methyl-
Hz, 1H), 8.04-7.97 (m, 2H), 7.93-7.81
(M + H) +


propanoyl)
(m, 3H), 7.08-7.02 (m, 2H), 4.78-4.70



piperidin-4-
(m, 1H), 4.69 (s, 2H), 4.41-3.50 (m, 4H),



yl]oxy}-N-
2.10-1.95 (m, 2H), 1.82-1.69 (m, 2H),



(imidazo[1,2-
1.44 (s, 6H)



a]pyridin-6-




ylmethyl)




benzamide



167
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 451


pyridin-6-
Hz, 1H), 8.04-7.97 (m, 2H), 7.93-7.82
(M + H) +


ylmethyl)-4-
(m, 3H), 7.09-7.03 (m, 2H), 4.80-4.72



({1-[(propan-
(m, 1H), 4.69 (s, 2H), 4.19 (s, 2H), 3.87-



2-yloxy)
3.73 (m, 2H), 3.73-3.62 (m, 1H), 3.59-



acetyl]
3.45 (m, 2H), 2.11-1.93 (m, 2H), 1.87-



piperidin-4-
1.68 (m, 2H), 1.19 (d, J = 6.1 Hz, 6H)



ylloxy)




benzamide



168
4-[(1-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


butanoyl-
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 421


piperidin-
Hz, 1H), 8.04-7.97 (m, 2H), 7.96-7.81
(M + H) +


4-yl)oxy]-N-
(m, 3H), 7.08-7.02 (m, 2H), 4.78-4.70



(imidazo[1,
(m, 1H), 4.69 (s, 2H), 3.90-3.73 (m, 2H),



2-a]pyridin-
3.59-3.46 (m, 2H), 2.40 (t, J = 7.5 Hz,



6-ylmethyl)
2H), 2.10-1.90 (m, 2H), 1.84-1.57 (m,



benzamide
4H), 0.98 (t, J = 7.4 Hz, 3H)


169
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.80-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 451


pyridin-
Hz, 1H), 8.04-7.97 (m, 2H), 7.94-7.82
(M + H) +


6-ylmethyl)-
(m, 3H), 7.09-7.03 (m, 2H), 4.80-4.71



4-{(3-
(m, 1H), 4.69 (s, 2H), 4.01-3.71 (m, 2H),



methoxy-
3.71-3.41 (m, 3H), 3.38-3.31 (m, 1H),



2-methyl-
3.30 (s, 3H), 3.26-3.16 (m, 1H), 2.12-



propanoyl)
1.88 (m, 2H), 1.87-1.61 (m, 2H), 1.06 (d,



piperidin-4-
J = 6.8 Hz, 3H)



yl]oxy}




benzamide



170
N-(imidazo
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


[1,2-a]
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 461


pyridin-6-
Hz, 1H), 8.04-7.97 (m, 2H), 7.94-7.81
(M + H) +


ylmethyl)-4-
(m, 3H), 7.09-7.03 (m, 2H), 4.80-4.73



{[1-(3,3,3-
(m, 1H), 4.69 (s, 2H), 3.90-3.72 (m, 2H),



trifluoro-
3.66-3.47 (m, 4H), 2.11-1.90 (m, 2H),



propanoyl)
1.91-1.68 (m, 2H)



piperidin-




4-yl]oxy}




benzamide



171
N-(imidazo[1,
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


2-a]pyridin-
8.79-8.76 (m, 1H), 8.21 (dd, J = 2.1, 0.7
m/e 477


6-ylmethyl)-
Hz, 1H), 8.04-7.97 (m, 2H), 7.93-7.82
(M + H) +


4-{[1-
(m, 3H), 7.09-7.03 (m, 2H), 4.78-4.71



(tetrahydro-
(m, 1H), 4.68 (s, 2H), 3.97-3.74 (m, 4H),



2H-pyran-4-
3.59-3.48 (m, 2H), 3.48-3.38 (m, 2H),



ylacetyl)
2.37 (d, J = 7.0 Hz, 2H), 2.10-1.90 (m,



piperidin-4-
3H), 1.85-1.60 (m, 4H), 1.41-1.26 (m,



yl]oxy}
2H)



benzamide



172
4-{[1-(cyclo-
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


propylacet
8.79-8.75 (m, 1H), 8.21 (dd, J = 2.2, 0.7
m/e 433


yl)piperidin-
Hz, 1H), 8.04-7.97 (m, 2H), 7.93-7.82
(M + H) +


4-yl]oxy}-N-
(m, 3H), 7.09-7.03 (m, 2H), 4.79-4.71



(imidazo[1,2-
(m, 1H), 4.69 (s, 2H), 3.92-3.73 (m, 2H),



a]pyridin-6-
3.60-3.47 (m, 2H), 2.36 (d, J = 6.8 Hz,



ylmethyl)
2H), 2.10-1.91 (m, 2H), 1.86-1.65 (m,



benzamide
2H), 1.08-0.94 (m, 1H), 0.58-0.47 (m,




2H), 0.23-0.16 (m, 2H)


173
N-(imidazo[1,
1 H NMR (400 MHz, methanol-d 4 ) δ ppm
(ESI(+))


2-a]pyridin-
8.80-8.75 (m, 1H), 8.22-8.19 (m, 1H),
m/e 463


6-ylmethyl)-
8.04-7.97 (m, 2H), 7.92-7.81 (m, 3H),
(M + H) +


4-{[1-
7.09-7.03 (m, 2H), 4.79-4.70 (m, 1H),



(tetrahydro-
4.69 (s, 2H), 4.29-4.18 (m, 1H), 3.94 -



furan-2-
3.66 (m, 4H), 3.65-3.45 (m, 2H), 2.76 (dd,



ylacetyl)
J = 14.8, 7.6 Hz, 1H), 2.52 (dd, J = 14.8,



piperidin-4-
5.2 Hz, 1H), 2.18-1.67 (m, 7H), 1.69-1.53



yl]oxy}
(m, 1H)



benzamide



411
4-[(1-acetyl-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


piperidin-
8.96 (t, J = 5.9 Hz, 1H), 8.48 (d, J = 7.0
m/e 393


4-yl)oxy]-N-
Hz, 1H), 7.88 (m, 3H), 7.51 (s, 1H), 7.37
(M + H) +


(imidazo[1,2-
(s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 6.9,



a]pyridin-7-
1.6 Hz, 1H), 4.72 (m, 1H), 4.49 (d, J = 5.9



ylmethyl)
Hz, 2H), 3.85 (m, 1H), 3.68 (m, 1H), 3.50-



benzamide
315 (m, 2H), 2.02 (s, 3H), 2.03-1.85




(m 2H), 1.62 (m, 1H), 1.51 (m, 1H)


412
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


2-a]pyridin-
8.96 (t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9,
m/e 421


7-ylmethyl)-
0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J = 1.2
(M + H) +


4-{[1-(2-
Hz, 1H), 7.37 (s, 1H), 7.07 (m, 2H), 6.85



methyl-
(dd, J = 6.9, 1.7 Hz, 1H), 4.73 (m, 1H),



propanoyl)
4.49 (d, J = 5.9 Hz, 2H), 3.96-3.70 (m, 2H),



piperidin-4-
3.45-3.20 (m, 2H), 2.89 (m, 1H), 1.93 (m,



yl]oxy}
2H), 1.58 (m, 2H), 1.00 (d, J = 6.7 Hz, 6H)



benzamide



413
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 435


7-ylmethyl)-
1H), 7.88 (m, 3H), 7.51 (s, 1H), 7.37 (s,
(M + H) +


4-({1-[(2S)-
1H), 7.07 (m, 2H), 6.85 (dd, J = 6.9, 1.6 Hz,



2-methyl-
1H), 4.74 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H),



butanoyl]
4.00-3.74 (m, 2H), 3.50-3.15 (m, 2H),



piperidin-4-
2.72 (m, 1H), 1.95 (m, 2H), 1.54 (m, 3H),



yl}oxy)
1.27 (m, 1H), 0.98 (d, J = 6.7 Hz, 3H), 0.81



benzamide
(t, J = 7.4 Hz, 3H)


414
4-{[1-(cyclo-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.95
(ESI(+))


propylacet
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 433


yl)piperidin-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


4-yl]oxy}-N-
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0,



(imidazo[1,2-
1.7 Hz, 1H), 4.73 (m, 1H), 4.49 (d, J = 5.9



a]pyridin-7-
Hz, 2H), 3.89 (m, 1H), 3.69 (m, 1H), 3.40-



ylmethyl)
3.15 (m, 2H), 2.28 (d, J = 6.7 Hz, 2H), 1.93



benzamide
(m, 2H), 1.85-1.41 (m, 2H), 0.95 (m, 1H),




0.45 (m, 2H), 0.12 (m, 2H)


415
4-[(1-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


benzoyl-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 455


piperidin-
1H), 7.90 (m, 3H), 7.51 (m, 1H), 7.47-
(M + H) +


4-yl)oxy]-N-
7.37 (m, 5H), 7.36 (m, 1H), 7.07 (m, 2H),



(imidazo[1,2-
6.84 (dd, J = 7.0, 1.7 Hz, 1H), 4.78 (m, 1H),



a]pyridin-7-
4.49 (d, J = 5.9 Hz, 2H), 4.00 (m, 1H), 3.55



ylmethyl)
(m, 1H), 3.45-3.15 (m, 2H), 2.00 (m, 2H),



benzamide
164 (m, 2H)


416
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 451


7-ylmethyl)-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


4-({1-
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0,



[(propan-2-
1.7 Hz, 1H), 4.74 (m, 1H), 4.49 (d, J = 5.9



yloxy)acetyl]
Hz, 2H), 4.10 (d, J = 1.1 Hz, 2H), 3.85 (m,



piperidin-4-
1H), 3.70 (m, 1H), 3.60 (m, 1H), 3.40-



yl}oxy)
3.15 (m, 2H), 1.97 (m, 2H), 1.69-1.45 (m,



benzamide
2H), 1.11 (d, J = 6.1 Hz, 6H)


417
4-{[1-(2-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


hydroxy-2-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 437


methyl-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


propanoyl)
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0,



piperidin-4-
1.7 Hz, 1H), 5.42 (m, 1H), 4.73 (m, 1H),



yl]oxy}-N-
4.49 (d, J = 5.9 Hz, 2H), 4.42-3.78 (m,



(imidazo[1,2-
2H), 3.70-3.20 (m, 2H), 1.95 (m, 2H),



a]pyridin-7-
1.57 (m, 2H), 1.32 (s, 6H)



ylmethyl)




benzamide



418
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 449


7-ylmethyl)-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


4-({1-[(2R)-
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0,



tetrahydro-
1.7 Hz, 1H), 4.79-4.64 (m, 2H), 4.49 (d, J =



furan-2-
5.9 Hz, 2H), 3.95-3.70 (m, 4H), 3.50-



ylcarbonyl]
3.15 (m, 2H), 2.10-1.90 (m, 4H), 1.90-



piperidin-4-
1.75 (m, 2H), 1.70-1.43 (m, 2H)



yl}oxy)




benzamide



419
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 449


7-ylmethyl)-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


4-({1-[(2S)-
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 6.9,



tetrahydro-
1.7 Hz, 1H), 4.79-4.64 (m, 2H), 4.49 (d, J =



furan-2-
5.9 Hz, 2H), 3.94-3.67 (m, 4H), 3.50-



ylcarbonyl]
3.15 (m, 2H), 2.10-1.90 (m, 4H), 1.90-



piperidin-4-
1.75 (m, 2H), 1.70-1.43 (m, 2H)



yl}oxy)




benzamide



420
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 463


7-ylmethyl)-
1H), 7.88 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


4-{[1-
7.37 (s, 1H), 7.07 (m, 2H), 6.85 (dd, J = 7.0,



(tetrahydro-
1.7 Hz, 1H), 4.73 (m, 1H), 4.49 (d, J = 5.9



2H-pyran-4-
Hz, 2H), 3.84 (m, 4H), 3.45-3.15 (m, 4H),



ylcarbonyl)
2.90 (m, 1H), 1.96 (m, 2H), 1.65-1.45 (m,



piperidin-4-
6H)



yl]oxy}




benzamide



421
4-{[1-(1,4-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


dioxan-2-
(t, J = 6.0 Hz, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 465


ylcarbonyl)
1H), 7.89 (m, 3H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


piperidin-4-
7.37 (d, J = 1.5 Hz, 1H), 7.07 (m, 2H), 6.85



yl]oxy}-N-
(dd, J = 7.0, 1.7 Hz, 1H), 4.74 (m, 1H), 4.49



(imidazo[1,2-
(d, J = 5.9 Hz, 2H), 4.35 (dd, J = 9.4, 2.8



a]pyridin-7-
Hz, 1H), 3.90-3.55 (m, 7H), 3.55-3.15



ylmethyl)
(m, 3H), 1.98 (m, 2H), 1.75-1.40 (m, 2H)



benzamide



422
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.95
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 477


7-ylmethyl)-
7.89 (m, 3H), 7.51 (s, 1H), 7.37 (bs, 1H),
(M + H) +


4-{[1-
7.07 (m, 2H), 6.85 (dd, J = 6.9, 1.7 Hz, 1H),



(tetrahydro-
4.72 (m, 1H), 4.49 (d, J = 5.9 Hz, 2H), 3.95



2H-pyran-4-
3.67 (m, 4H), 3.45-3.15 (m, 5H), 2.28-



ylacetyl)
(m, 2H), 1.93 (m, 2H), 1.67-1.42 (m, 4H),



piperidin-4-
1.26-1.12 (m, 2H)



yl]oxy}




benzamide



423
N-(imidazo[1,
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.96
(ESI(+))


2-a]pyridin-
(t, J = 5.9 Hz, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 478


7-ylmethyl)-
7.89 (m, 3H), 7.51 (s, 1H), 7.37 (s, 1H),
(M + H) +


4-{[1-
7.07 (m, 2H), 6.85 (dd, J = 7.0, 1.6 Hz, 1H),



(morpholin-
4.73 (m, 1H), 4.49 (d, J = 5.8 Hz, 2H), 3.86



4-ylacetyl)
(m, 2H), 3.57 (m, 4H), 3.50-3.20 (m, 2H),



piperidin-
3.20-3.05 (m, 2H), 2.40 (m, 4H), 2.08-



4-yl]oxy}
1.89 (m, 2H), 1.70-1.41 (m, 2H)



benzamide























































































































































































































































































Example 204
2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
Example 204A
2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
Example 204B
2-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 51A, substituting 2-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrol-1-yl)propan-2-ol for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, methanol-d 4 ) ppm 8.41 (d, J=7.05 Hz, 1H) 8.27 (d, J=7.92 Hz, 2H) 8.00 (s, 1H) 7.80 (s, 1H) 7.53 (s, 1H) 7.47 (s, 1H) 6.93 (dd, J=6.99, 1.36 Hz, 1H) 4.61 (s, 2H) 4.16 (s, 2H) 1.20 (s, 6H); MS (ESI)(+)) m/e 397 (M+H) + .
Example 205
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 51A, substituting 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, methanol-d 4 ) ppm 8.40 (d, J=6.94 Hz, 1H) 8.27 (d, J=7.48 Hz, 2H) 8.00 (s, 1H) 7.80 (s, 1H) 7.53 (s, 1H) 7.47 (s, 1H) 6.93 (d, J=6.83 Hz, 1H) 4.61 (s, 2H) 4.01 (d, J=7.26 Hz, 2H) 2.12-2.30 (m, 1H) 0.93 (d, J=6.61 Hz, 6H); MS (ESI)(+)) m/e 381 (M+H) + .
Example 207
tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.62 (s, 1H), 8.92 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.79 (m, 3H), 7.57-7.49 (m, 3H), 7.39-7.35 (m, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 1.49 (s, 9H); MS (ESI(+)) m/e 367 (M+H) + .
Example 208
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide
Example 208A
tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)benzoic acid for 4-nitrobenzoic acid.
Example 208B
4-amino-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl {4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 208C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydro-2H-pyran-4-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 1A, substituting 4-amino-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.74 (dd, J=7.0, 0.9 Hz, 1H), 8.17 (dd, J=2.2, 0.7 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.91-7.84 (m, 2H), 7.81-7.78 (m, 1H), 7.75-7.68 (m, 2H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 4.79-4.74 (m, 2H), 3.98-3.89 (m, 2H), 3.50-3.38 (m, 2H), 2.38-2.32 (m, 2H), 2.20-2.02 (m, 1H), 1.74-1.61 (m, 2H), 1.47-1.28 (m, 2H); MS (ESI(+)) m/e 393 (M+H) + .





TABLE 11



The following Examples were prepared essentially as described in

Example 208, substituting the appropriate carboxylic acid in Example

208A and the appropriate carboxylic acid in Example 208C.





Ex
Name
MS



209
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-
(ESI(+))


2-ylacetyl)amino]benzamide
m/e 379



(M + H) +

210
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[3-
(ESI(+))


(tetrahydrofuran-2-yl)propanoyl]amino}benzamide
m/e 393



(M + H) +

211
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(propan-2-
(ESI(+))


yloxy)acetyl]amino}benzamide
m/e 367



(M + H) +

212
4-[(3-cyclopentylpropanoyl)amino]-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 391



(M + H) +

213
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(4-
(ESI(+))


methylpentanoyl)amino]benzamide
m/e 365



(M + H) +

214
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(tetrahydrofuran-
(ESI(+))


3-ylacetyl)amino]benzamide
m/e 379



(M + H) +

305
4-[(cyclopentylacetyl)amino]-3-fluoro-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 395



(M + H) +

463
4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 395



(M + H) +

867
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2-
(ESI(+))


methoxyphenyl)acetyl]amino}benzamide
m/e 415



(M + H) +

868
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-
(ESI(+))


[(phenylacetyl)amino]benzamide
m/e 385



(M + H) +

869
4-(benzoylamino)-N-(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)benzamide
m/e 371



(M + H) +

870
2,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)carbamoyl]phenyl}benzamide
m/e 407



(M + H) +

871
3,5-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)carbamoyl]phenyl}benzamide
m/e 407



(M + H) +

872
3,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)carbamoyl]phenyl}benzamide
m/e 407



(M + H) +

873
2,4-difluoro-N-{4-[(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)carbamoyl]phenyl}benzamide
m/e 407



(M + H) +

874
2-fluoro-N-{4-[(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)carbamoyl]phenyl}benzamide
m/e 389



(M + H) +

875
N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]
(ESI(+))


phenyl}-3-methoxybenzamide
m/e 401



(M + H) +

876
4-{[(2-fluorophenyl)acetyl]amino}-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 403



(M + H) +

880
N-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]
(ESI(+))


phenyl}-2-methoxybenzamide
m/e 401



(M + H) +

890
4-{[(2,5-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 421



(M + H) +

891
4-{[(2,4-difluorophenyl)acetyl]amino}-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 421



(M + H) +

895
4-{[difluoro(phenyl)acetyl]amino}-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 421



(M + H) +

896
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[(2-methyl-2-
(ESI(+))


phenylpropanoyl)amino]benzamide
m/e 413



(M + H) +



























































































Example 215
4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
Example 215A
methyl 4-(4-cyanobenzylamino)benzoate
A solution of methyl 4-aminobenzoate (0.2 g, 1.323 mmol) and 4-formylbenzonitrile (0.177 g, 1.350 mmol) in methanol (2 ml) and dichloromethane (4 ml) was treated with acetic acid (0.379 ml, 6.62 mmol) followed by MP-cyanoborohydride (1.151 g, 2.65 mmol) and the reaction was slowly stirred at room temperature. After 16 hours, the mixture was filtered and concentrated and the concentrate was partitioned between 2 N sodium hydroxide and dichloromethane. The organic phase was concentrated to give the title compound with 30% of remaining 4-formylbenzonitrile.
Example 215B
methyl 4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoate
The title compound was prepared as described in Example 52A, substituting methyl 4-(4-cyanobenzylamino)benzoate for methyl 4-aminobenzoate.
Example 215C
4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 215D
4-[(4-cyanobenzyl)(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(N-(4-cyanobenzyl)-2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.08 (t, J=5.8 Hz, 1H), 8.47 (s, 1H), 7.94 (s, 1H), 7.90-7.85 (m, 2H), 7.79-7.74 (m, 2H), 7.56-7.49 (m, 2H), 7.43-7.37 (m, 2H), 7.36-7.30 (m, 2H), 7.21 (dd, J=9.3, 1.7 Hz, 1H), 4.98 (bs, 2H), 4.45 (d, J=5.8 Hz, 2H), 2.19-2.13 (m, 3H), 1.74-1.66 (m, 2H), 1.51-1.38 (m, 4H), 1.01-0.92 (m, 2H); MS (ESI(+)) m/e 492 (M+H) + .
Example 216
tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.56 (s, 1H), 8.51-8.45 (m, 1H), 7.88 (s, 1H), 7.52-7.49 (m, 1H), 7.39-7.36 (m, 1H), 7.35-7.30 (m, 2H), 7.12-7.07 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.67 (t, J=6.0 Hz, 1H), 4.32 (d, J=6.0 Hz, 2H), 4.10-4.00 (m, 2H), 2.89-2.65 (m, 2H), 2.62-2.54 (m, 1H), 1.75-1.66 (m, 2H), 1.49-1.37 (m, 11H); MS (ESI(+)) m/e 450 (M+H) + .
Example 217
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.81 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.40-7.32 (m, 3H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.13-4.03 (m, 2H), 2.91-2.69 (m, 3H), 1.82-1.72 (m, 2H), 1.60-1.44 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 435 (M+H) + .
Example 220
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea
Example 220A
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yl)phenyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 220B
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylcarbonyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yl)phenyl)urea for 3-methylbutan-1-amine and tetrahydrofuran-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.72 (d, J=7.0 Hz, 1H), 8.17-8.12 (m, 1H), 7.98-7.93 (m, 1H), 7.78 (bs, 1H), 7.48-7.41 (m, 1H), 7.35-7.28 (m, 2H), 7.18-7.12 (m, 2H), 4.81-4.72 (m, 1H), 4.67-4.55 (m, 3H), 4.19-4.08 (m, 1H), 4.01-3.91 (m, 1H), 3.90-3.81 (m, 1H), 3.24-3.09 (m, 1H), 2.85-2.67 (m, 2H), 2.30-2.14 (m, 1H), 2.09-1.79 (m, 5H), 1.73-1.46 (m, 2H); MS (ESI(+)) m/e 448 (M+H) + .





TABLE 12



The following Examples were prepared essentially as described in Example

220, substituting the appropriate carboxylic acid in Example 220B.





Ex
Name
MS







221
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-
(ESI(+))


2H-pyran-4-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 462



(M + H) +

222
1-{4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]phenyl}-
(ESI(+))


3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 464



(M + H) +

223
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-
(ESI(+))


2H-pyran-4-ylacetyl)piperidin-4-yl]phenyl}urea
m/e 476



(M + H) +

224
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(morpholin-
(ESI(+))


4-ylacetyl)piperidin-4-yl]phenyl}urea
m/e 477



(M + H) +

225
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
(ESI(+))


(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]phenyl}urea
m/e 462



(M + H) +

226
1-{4-[1-(3-hydroxy-3-methylbutanoyl)piperidin-4-
(ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 450



(M + H) +

227
1-{4-[1-(2-hydroxy-3-methylpropanoyl)piperidin-4-
(ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 436



(M + H) +

228
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-
(ESI(+))


methylpropanoyl)piperidin-4-yl]phenyl}urea
m/e 420



(M + H) +

229
1-[4-(1-benzoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)urea
m/e 454



(M + H) +

243
1-(4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-
(ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 510


a]pyridin-7-ylmethyl)urea
(M + H) +

286
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1[(3S)-
(ESI(+))


tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea
m/e 448



(M + H) +

287
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1[(3R)-
(ESI(+))


tetrahydrofuran-3-ylcarbonyl]piperidin-4-yl}phenyl)urea
m/e 448



(M + H) +

288
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1[(2S)-
(ESI(+))


tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea
m/e 448



(M + H) +

289
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1[(2R)-
(ESI(+))


tetrahydrofuran-2-ylcarbonyl]piperidin-4-yl}phenyl)urea
m/e 448



(M + H) +

709
1-[4-(1-butanoylpiperidin-4-yl)phenyl]-3-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)urea
m/e 420



(M + H) +

710
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1[(2S)-2-
(ESI(+))


methylbutanoyl]piperidin-4-yl}phenyl)urea
m/e 434



(M + H) +

711
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
(ESI(+))


methylcyclopropyl)carbonyl]piperidin-4-yl}phenyl)urea
m/e 432



(M + H) +

712
1-{4-[1-(cyclopropylacetyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 432



(M + H) +

713
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3,3,3-
(ESI(+))


trifluoropropanoyl)piperidin-4-yl]phenyl}urea
m/e 460



(M + H) +

714
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,4,4-
(ESI(+))


trifluorobutanoyl)piperidin-4-yl]phenyl}urea
m/e 474



(M + H) +

715
1-(4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-
(ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 496



(M + H) +

716
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
(ESI(+))


(phenylacetyl)piperidin-4-yl]phenyl}urea
m/e 468



(M + H) +

719
1-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 472



(M + H) +

720
1-{4-[1-(3-fluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 472



(M + H) +

721
1-{4-[1-(4-fluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 472



(M + H) +

722
1-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 490



(M + H) +

723
1-{4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 490



(M + H) +

724
1-{4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 490



(M + H) +

725
1-{4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]phenyl}-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 490



(M + H) +

938
1-(4-{1-[2-chloropyridin-3-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 489



(M + H) +

939
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(3-
ESI(+))


methylbut-2-enoyl)piperidin-4-yl]phenyl}urea
m/e 432



(M + H) +

940
1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 448



(M + H) +

941
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methylcyclopent-1-en-1-yl)carbonyl]piperidin-4-
m/e 458


yl}phenyl)urea
(M + H) +

942
1-{4-[1-(2-ethylbutanoyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 448



(M + H) +

943
1-(4-{1-[4-fluorophenoxy)acetyl]piperidin-4-yl}phenyl)-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 502



(M + H) +

944
1-{4-[1-(2,4-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 514



(M + H) +

945
1-{4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 458



(M + H) +

946
1-{4-[1-(2,5-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 514



(M + H) +

947
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea
m/e 498



(M + H) +

948
1-{4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 498



(M + H) +

949
1-{4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 514



(M + H) +

950
1-{4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]phenyl}-
ESI(+))


3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 477



(M + H) +

951
1-(4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 503


a]pyridin-7-ylmethyl)urea
(M + H) +

952
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-
ESI(+))


methoxyphenyl)acetyl]piperidin-4-yl}phenyl)urea
m/e 498



(M + H) +

953
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[1-oxo-2,3-
ESI(+))


dihydro-1H-inden-4-yl)carbonyl]piperidin-4-
m/e 508


yl}phenyl)urea
(M + H) +

954
1-{4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 513



(M + H) +

955
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-2-
ESI(+))


methylbut-2-enoyl]piperidin-4-yl}phenyl)urea
m/e 432



(M + H) +

956
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(1H-indol-
ESI(+))


3-ylacetyl)piperidin-4-yl]phenyl}urea
m/e 507



(M + H) +

957
1-{4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 484



(M + H) +

1011
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-
ESI(+))


(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}piperidin-
m/e 486


4-yl)phenyl]urea
(M + H) +

1012
1-(4-{1-[(2S)-2,3-dihydro-1,4-benzodioxin-2-
ESI(+))


ylcarbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 512


a]pyridin-7-ylmethyl)urea
(M + H) +

1013
1-(4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 497


a]pyridin-7-ylmethyl)urea
(M + H) +

1014
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-
ESI(+))


4,5,6,7-tetrahydro-2H-indazol-3-yl)carbonyl]piperidin-4-
m/e 512


yl}phenyl)urea
(M + H) +

1015
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-
ESI(+))


tetrahydro-2,1-benzoxazol-3-ylcarbonyl)piperidin-4-
m/e 499


yl]phenyl}urea
(M + H) +

1016
1-(4-{1-[2-chloro-5-fluoropyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 507


ylmethyl)urea
(M + H) +

1017
1-(4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 487


ylmethyl)urea
(M + H) +

1018
1-(4-{1-[2-chloro-3-fluoropyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 507


ylmethyl)urea
(M + H) +

1019
1-(4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 489



(M + H) +

1020
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[1-
ESI(+))


(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-4-
m/e 495


yl)phenyl]urea
(M + H) +

1021
1-(4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 512


ylmethyl)urea
(M + H) +

1022
1-[4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-
ESI(+))


yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-
m/e 494


a]pyridin-7-ylmethyl)urea
(M + H) +

1023
1-{4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)
ESI(+))


piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-
m/e 512


ylmethyl)urea
(M + H) +

1024
1-{4-[1-(2,3-dihydro-1-benzofuran-2-ylcarbonyl)
ESI(+))


piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-
m/e 496


ylmethyl)urea
(M + H) +

1025
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-
ESI(+))


methoxycyclohexyl)carbonyl]piperidin-4-yl}phenyl)urea
m/e 490



(M + H) +

1026
1-{4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)
ESI(+))


piperidin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-
m/e 512


ylmethyl)urea
(M + H) +

1027
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
ESI(+))


(isoquinolin-4-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 505



(M + H) +

1028
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-4-
m/e 509


yl}phenyl)urea
(M + H) +

1029
1-(4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 514


a]pyridin-7-ylmethyl)urea
(M + H) +

1030
1-(4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 471



(M + H) +

1031
1-{4-[1-(cinnolin-4-ylcarbonyl)piperidin-4-yl]phenyl}-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 506



(M + H) +

1032
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(quinolin-7-
ESI(+))


ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 505



(M + H) +

1033
1-{4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-yl]phenyl}-
ESI(+))


3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 497



(M + H) +

1034
1-(4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 485


ylmethyl)urea
(M + H) +

1035
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(5,6,7,8-
ESI(+))


tetrahydroquinolin-3-ylcarbonyl)piperidin-4-
m/e 509


yl]phenyl}urea
(M + H) +

1036
1-{4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-
ESI(+))


ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-
m/e 511


a]pyridin-7-ylmethyl)urea
(M + H) +

1037
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
ESI(+))


(isoquinolin-7-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 505



(M + H) +

1038
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
ESI(+))


(quinoxalin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 506



(M + H) +

1039
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-(2-
ESI(+))


methoxypyridin-3-yl)prop-2-enoyl]piperidin-4-
m/e 511


yl}phenyl)urea
(M + H) +

1040
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2E)-3-
ESI(+))


(pyridin-2-yl)prop-2-enoyl]piperidin-4-yl}phenyl)urea
m/e 481



(M + H) +

1041
1-(4-{1-[(4-chloro-2,6-dimethylpyridin-3-
ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e


a]pyridin-7-ylmethyl)urea
XXX



(M + H) +

1042
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(8-
ESI(+))


methylimidazo[1,2-a]pyridin-2-yl)carbonyl]piperidin-4-
m/e 517


yl}phenyl)urea
(M + H) +

1043
1-(4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 499



(M + H) +

4044
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[1-methyl-
ESI(+))


4,5,6,7-tetrahydro-1H-indazol-3-yl)carbonyl]piperidin-4-
m/e 512


yl}phenyl)urea
(M + H) +

1045
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[4-
ESI(+))


methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]piperidin-4-
m/e 497


yl}phenyl)urea
(M + H) +

1046
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methyl-2,3-dihydro-1-benzofuran-5-yl)carbonyl]
m/e 510


piperidin-4-yl}phenyl)urea
(M + H) +

1047
1-(4-{1-[(4-chloro-1-ethyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 506


a]pyridin-7-ylmethyl)urea
(M + H) +

1048
1-{4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 497



(M + H) +

1049
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-
ESI(+))


(isoquinolin-8-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 505



(M + H) +

1050
1-(4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}phenyl)-3-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 493



(M + H) +

1051
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(3-
ESI(+))


methoxythiophen-2-yl)carbonyl]piperidin-4-
m/e 490


yl}phenyl)urea
(M + H) +

1052
1-{4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl[phenyl}-
ESI(+))


3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 497



(M + H) +

1053
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(4,5,6,7-
ESI(+))


tetrahydro-1,3-benzothiazol-2-ylcarbonyl)piperidin-4-
m/e 515


yl[phenyl}urea
(M + H) +

1054
1-{4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 511



(M + H) +

1055
1-(4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 473



(M + H) +

1056
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[3-methyl-
ESI(+))


1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]carbonyl}piperidin-4-
m/e 498


yl)phenyl]urea
(M + H) +

1057
1-{4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 512



(M + H) +

1058
1-(4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 489



(M + H) +

1059
1-(4-{1-[(5,6-dimethylpyridin-3-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 483



(M + H) +

1060
1-{4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 511



(M + H) +

1065
1-(4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 517



(M + H) +

1066
1-(4-{1-[3,5-difluoropyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 492



(M + H) +

1121
1-(4-{1-[(2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 501


ylmethyl)urea
(M + H) +

1122
1-{4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 511



(M + H) +

1123
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-
ESI(+))


methyl-1H-indazol-6-yl)carbonyl]piperidin-4-yl}
m/e 508


phenyl)urea
(M + H) +

1124
1-(4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 506


a]pyridin-7-ylmethyl)urea
(M + H) +

1125
1-(4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 483



(M + H) +

1126
1-(4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 514


ylmethyl)urea
(M + H) +

1127
1-(4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 471


ylmethyl)urea
(M + H) +

1128
1-(4-{1-[1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 501


ylmethyl)urea
(M + H) +

1129
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(thieno[3,2-
ESI(+))


b]furan-5-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 500



(M + H) +

1130
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-
ESI(+))


methoxythiophen-2-yl)carbonyl]piperidin-4-yl}
m/e 490


phenyl)urea
(M + H) +

1131
1-(4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 485



(M + H) +

1132
1-(4-{1-[5-cyclopropylpyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 495



(M + H) +

1133
1-{4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-4-yl]
ESI(+))


phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 515



(M + H) +

1134
1-[4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-
ESI(+))


yl]carbonyl}piperidin-4-yl)phenyl]-3-(imidazo[1,2-
m/e 514


a]pyridin-7-ylmethyl)urea
(M + H) +

1135
1-{4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-4-
ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 494



(M + H) +

1136
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(4-
ESI(+))


methoxy-5-methylpyridin-2-yl)carbonyl]piperidin-4-yl}
m/e 499


phenyl)urea
(M + H) +

1137
1-(4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 512


ylmethyl)urea
(M + H) +

1138
1-(4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 495



(M + H) +

1139
1-(4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 485



(M + H) +

1140
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[4-
ESI(+))


(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-4-
m/e 498


yl)phenyl]urea
(M + H) +

1141
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-
ESI(+))


methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]piperidin-4-yl}
m/e 500


phenyl)urea
(M + H) +

1142
1-(4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-
ESI(+))


yl)propanoyl]piperidin-4-yl}phenyl)-3-(imidazo[1,2-
m/e 512


a]pyridin-7-ylmethyl)urea
(M + H) +

1143
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(pyrazolo
ESI(+))


[1,5-a]pyridin-2-ylcarbonyl)piperidin-4-yl]phenyl}urea
m/e 494



(M + H) +

1144
1-{4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-4-yl]
ESI(+))


phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 494



(M + H) +

1145
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-
ESI(+))


(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}piperidin-4-yl)
m/e 487


phenyl]urea
(M + H) +

1146
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-
ESI(+))


methyl-1H-indazol-7-yl)carbonyl]piperidin-4-yl}
m/e 508


phenyl)urea
(M + H) +

1147
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methoxy-5-methylpyridin-3-yl)carbonyl]piperidin-4-yl}
m/e 499


phenyl)urea
(M + H) +

1148
1-(4-{1-[5,6-dimethoxypyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 515



(M + H) +

1149
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methyl-2H-indazol-4-yl)carbonyl]piperidin-4-yl}
m/e 508


phenyl)urea
(M + H) +

1150
1-(4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]piperidin-4-
ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 517



(M + H) +

1151
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(2-
ESI(+))


methyl-2H-indazol-6-yl)carbonyl]piperidin-4-yl}
m/e 508


phenyl)urea
(M + H) +

1152
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{1-[(1-
ESI(+))


methyl-1H-indazol-4-yl)carbonyl]piperidin-4-yl}
m/e 508


phenyl)urea
(M + H) +

1153
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-{[2-
ESI(+))


(trifluoromethyl)furan-3-yl]carbonyl}piperidin-4-
m/e 512


yl)phenyl]urea
(M + H) +











































































































































































































































































































































































































































Example 230
4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
Example 230A
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 230B
4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2-hydroxy-2-methylpropanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 /D 2 O, Temp=90° C.) δ ppm 8.77 (dd, J=6.9, 0.9 Hz, 1H), 8.22-8.18 (m, 1H), 8.02-7.98 (m, 1H), 7.88-7.81 (m, 2H), 7.77 (s, 1H), 7.44 (dd, J=6.9, 1.6 Hz, 1H), 7.40-7.34 (m, 2H), 4.76-4.64 (m, 4H), 2.98-2.82 (m, 3H), 1.89-1.81 (m, 2H), 1.65-1.48 (m, 2H), 1.38 (s, 6H); MS (ESI(+)) m/e 421 (M+H) + .





TABLE 13



The following Examples were prepared essentially as described in

Example 230, substituting the appropriate carboxylic acid in

Example 230B.





Ex
Name
MS



231
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]
m/e 443


benzamide
(M + H) +

232
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]
m/e 447


benzamide
(M + H) +

233
4-[1-(1,4-dioxan-2-ylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 445



(M + H) +

234
4-{1-[(1,1-dioxidotetrahydro-2H-thiopyran-4-
(ESI(+))


yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]
m/e 495


pyridin-7-ylmethyl)benzamide
(M + H) +

235
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(tetrahydrofuran-2-ylacetyl)piperidin-4-yl]
m/e 447


benzamide
(M + H) +

236
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]
m/e 461


benzamide
(M + H) +

237
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(propan-2-yloxy)acetyl]piperidin-4-yl}
m/e 435


benzamide
(M + H) +

238
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(2S)-2-methylbutanoyl]piperidin-4-yl}
m/e 419


benzamide
(M + H) +

239
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


methylpropanoyl)piperidin-4-yl]benzamide
m/e 405



(M + H) +

308
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(3S)-tetrahydrofuran-3-ylcarbonyl]piperidin-
m/e 433


4-yl}benzamide
(M + H) +

309
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(3R)-tetrahydrofuran-3-ylcarbonyl]piperidin-
m/e 433


4-yl}benzamide
(M + H) +

310
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(2R)-tetrahydrofuran-2-ylcarbonyl]piperidin-
m/e 433


4-yl}benzamide
(M + H) +

311
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(2S)-tetrahydrofuran-2-ylcarbonyl]piperidin-
m/e 433


4-yl}benzamide
(M + H) +

312
4[1-(cyclopropylacetyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 417



(M + H) +

313
4-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 377



(M + H) +

437
4-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 439



(M + H) +

44
4-{1-[(3,3-difluorocyclobutyl)carbonyl]piperidin-
(ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 453


benzamide
(M + H) +

441
4-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-
(ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 481


benzamide
(M + H) +

484
4-[1-(furan-2-ylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 429



(M + H) +

498
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(pyridin-2-ylcarbonyl)piperidin-4-yl]benzamide
m/e 440



(M + H) +

499
4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 433



(M + H) +

500
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-
(ESI(+))


methylbenzoyl)piperidin-4-yl]benzamide
m/e 453



(M + H) +

501
4-[1-(2,2-dimethylbutanoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 433



(M + H) +

502
4-[1-(cyclohexylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 445



(M + H) +

503
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(thiophen-2-ylcarbonyl)piperidin-4-yl]
m/e 445


benzamide
(M + H) +

504
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(3,3,3-trifluoropropanoyl)piperidin-4-yl]
m/e 445


benzamide
(M + H) +

505
4-(1-butanoylpiperidin-4-yl)-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)benzamide
m/e 405



(M + H) +

506
4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

507
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


methylbenzoyl)piperidin-4-yl]benzamide
m/e 453



(M + H) +

508
4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 457



(M + H) +

509
4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-
(ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 419


benzamide
(M + H) +

510
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(2E)-2-methylpent-2-enoyl]piperidin-4-yl}
m/e 431


benzamide
(M + H) +

511
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(1-methyl-1H-pyrazol-5-yl)carbonyl]piperidin-
m/e 443


4-yl]benzamide
(M + H) +

512
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(3-methyloxetan-3-yl)carbonyl]piperidin-4-yl}
m/e 433


benzamide
(M + H) +

513
4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo
(ESI(+))


[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 457



(M + H) +

514
4-{1-[(1-cyanocyclopropyl)carbonyl]piperidin-4-
(ESI(+))


yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 428


benzamide
(M + H) +

515
4-[1-(cyclopentylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 431



(M + H) +

516
4-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-(imidazo
(ESI(+))


[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 457



(M + H) +

517
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperidin-
m/e 443


4-yl}benzamide
(M + H) +

518
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


oxobutanoyl)piperidin-4-yl]benzamide
m/e 419



(M + H) +

519
4-{1-[(2,5-dimethylfuran-3-yl)carbonyl]
(ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-
m/e 457


7-ylmethyl)benzamide
(M + H) +

520
4-[1-(4-cyanobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 464



(M + H) +

521
4-[1-(3-cyanobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 464



(M + H) +

522
4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

523
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(pyrazin-2-ylcarbonyl)piperidin-4-yl]benzamide
m/e 441



(M + H) +

524
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(3-methylthiophen-2-yl)carbonyl]piperidin-
m/e 459


4-yl}benzamide
(M + H) +

525
4-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]
(ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 458


ylmethyl)benzamide
(M + H) +

526
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methoxybenzoyl)piperidin-4-yl]benzamide
m/e 469



(M + H) +

527
4-[1-(3-chlorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 473



(M + H) +

528
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-
(ESI(+))


methoxybenzoyl)piperidin-4-yl]benzamide
m/e 469



(M + H) +

529
4-[1-(4-chlorobenzoyl)piperidin-4-yl]-N-(imidazo
(ESI(+))


[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 473



(M + H) +

530
4-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

531
4-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 403



(M + H) +

532
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
(ESI(+))


propanoylpiperidin-4-yl)benzamide
m/e 391



(M + H) +

533
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(1-methyl-1H-pyrrol-2-yl)carbonyl]piperidin-
m/e 442


4-yl}benzamide
(M + H) +

534
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methylbutanoyl)piperidin-4-yl]benzamide
m/e 419



(M + H) +

535
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(pyridin-4-ylcarbonyl)piperidin-4-yl]benzamide
m/e 440



(M + H) +

536
4-[1-(2,3-dimethylbutanoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 433



(M + H) +

537
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
(ESI(+))


(pyridin-3-ylcarbonyl)piperidin-4-yl]benzamide
m/e 440



(M + H) +

538
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[(1-methylcyclopropyl)carbonyl]piperidin-
m/e 417


4-yl}benzamide
(M + H) +

539
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


methoxybenzoyl)piperidin-4-yl]benzamide
m/e 469



(M + H) +

699
4-[1-(2-chlorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 473



(M + H) +

700
4-[1-(2,6-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

701
4-[1-(3,4-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

702
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[3-(trifluoromethyl)benzoyl]piperidin-4-yl}
m/e 507


benzamide
(M + H) +

703
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
(ESI(+))


[3-(trifluoromethoxy)benzoyl]piperidin-4-yl}
m/e 523


benzamide
(M + H) +

704
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-
(ESI(+))


(trifluoromethoxy)benzoyl]piperidin-4-yl}
m/e 523


benzamide
(M + H) +

705
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[4-
(ESI(+))


(trifluoromethyl)benzoyl]piperidin-4-yl}
m/e 507


benzamide
(M + H) +

706
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-
(ESI(+))


(trifluoromethoxy)benzoyl]piperidin-4-yl}
m/e 523


benzamide
(M + H) +

707
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4[1-
(ESI(+))


(phenylacetyl)piperidin-4-yl]benzamide
m/e 453



(M + H) +

708
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[2-
(ESI(+))


(trifluoromethyl)benzoyl]piperidin-4-yl}
m/e 507


benzamide
(M + H) +

737
4-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 464


benzamide
(M + H) +

913
4-{1-[(2-chloropyridin-3-yl)carbonyl]piperidin-
(ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 474


benzamide
(M + H) +

914
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
ESI(+))


methylbut-2-enoyl)piperidin-4-yl]benzamide
m/e 417



(M + H) +

915
4-[1-(3-fluoro-4-methoxybenzoyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 487


benzamide
(M + H) +

916
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


methylcyclopent-1-en-1-yl)carbonyl]piperidin-
m/e 443


4-yl}benzamide
(M + H) +

917
4-[1-(2-ethylbutanoyl)piperidin-4-yl]-N-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 433



(M + H) +

918
4-{1-[(4-fluorophenoxy)acetyl]piperidin-4-yl}-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 487


benzamide
(M + H) +

919
4-[1-(3,5-dimethoxybenzoyl)piperidin-4-yl]-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 499


benzamide
(M + H) +

920
4-[1-(cyclohex-3-en-1-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 443


benzamide
(M + H) +

921
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


methoxyphenyl)acetyl]piperidin-4-yl}
m/e 483


benzamide
(M + H) +

922
4-[1-(3-hydroxy-2-phenylpropanoyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 483


benzamide
(M + H) +

923
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
ESI(+))


methylbenzoyl)piperidin-4-yl]benzamide
m/e 453



(M + H) +

924
4-[1-(2-acetylbenzoyl)piperidin-4-yl]-N-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 481


benzamide
(M + H) +

925
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


(methoxymethyl)benzoyl]piperidin-4-yl}
m/e 483


benzamide
(M + H) +

926
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
ESI(+))


phenylpropanoyl)piperidin-4-yl]benzamide
m/e 467



(M + H) +

927
4-[1-(2,6-dimethoxybenzoyl)piperidin-4-yl]-N-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 499



(M + H) +

928
4-[1-(N,N-diethyl-beta-alanyl)piperidin-4-yl]-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 462


benzamide
(M + H) +

929
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[(2-
ESI(+))


methylpropyl)sulfonyl]acetyl}piperidin-4-yl)
m/e 497


benzamide
(M + H) +

930
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
ESI(+))


phenoxypropanoyl)piperidin-4-yl]benzamide
m/e 483



(M + H) +

931
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


({[(1R,2S)-2-methylcyclohexyl]oxy}acetyl)
m/e 489


piperidin-4-yl]benzamide
(M + H) +

932
4-{1-[(2-chloro-6-methylpyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 488


ylmethyl)benzamide
(M + H) +

933
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-
ESI(+))


methoxyphenyl)acetyl]piperidin-4-yl}
m/e 483


benzamide
(M + H) +

934
4-[1-(2-chloro-4-cyanobenzoyl)piperidin-4-yl]-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 498


benzamide
(M + H) +

935
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2E)-2-methylbut-2-enoyl]piperidin-4-yl}
m/e 417


benzamide
(M + H) +

936
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2-methoxy-5-methylphenyl)acetyl]piperidin-
m/e 497


4-yl}benzamide
(M + H) +

937
4-[1-(2-hydroxy-3-methylbenzoyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 469


benzamide
(M + H) +

959
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
ESI(+))


{[1-(propan-2-yl)-1H-pyrazol-3-yl]carbonyl}
m/e 471


piperidin-4-yl)benzamide
(M + H) +

960
4-{1-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]
m/e 483


pyridin-7-ylmethyl)benzamide
(M + H) +

961
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)
m/e 497


carbonyl]piperidin-4-yl}benzamide
(M + H) +

962
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(4,5,6,7-tetrahydro-2,1-benzoxazol-3-
m/e 484


ylcarbonyl)piperidin-4-yl]benzamide
(M + H) +

963
4-{1-[(3-fluoro-6-methylpyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 472


ylmethyl)benzamide
(M + H) +

964
4-{1-[(2-chloro-3-fluoropyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 492


ylmethyl)benzamide
(M + H) +

965
4-{1-[(3-chloropyridin-2-yl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 474


benzamide
(M + H) +

966
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
ESI(+))


{[1-(pyridin-2-yl)cyclopropyl]carbonyl}piperidin-
m/e 480


4-yl)benzamide
(M + H) +

967
4-{1-[(1-cyclopentyl-1H-pyrazol-3-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 497


ylmethyl)benzamide
(M + H) +

968
4-{1-[2-(3-fluorophenoxy)propanoyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 501


benzamide
(M + H) +

969
4-(1-{[1-(difluoromethyl)-1H-pyrazol-5-
ESI(+))


yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]
m/e 479


pyridin-7-ylmethyl)benzamide
(M + H) +

970
4-[1-(3,4-dihydro-2H-chromen-6-ylcarbonyl)
ESI(+))


piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-
m/e 495


ylmethyl)benzamide
(M + H) +

971
4-{1-[(cyclohexyloxy)acetyl]piperidin-4-yl}-N-
ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 475



(M + H) +

972
4-{1-[(2-chloropyridin-3-yl)acetyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 488


benzamide
(M + H) +

973
4-{1-[(5-cyclopropyl-1,2-oxazol-3-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 470


ylmethyl)benzamide
(M + H) +

974
4-[1-(2H-chromen-3-ylcarbonyl)piperidin-4-
ESI(+))


yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 493


benzamide
(M + H) +

975
4-{1-[(3,5-difluoropyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-
m/e 476


7-ylmethyl)benzamide
(M + H) +

976
4-[1-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)
ESI(+))


piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-
m/e 497


7-ylmethyl)benzamide
(M + H) +

977
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-
ESI(+))


methoxycyclohexyl)carbonyl]piperidin-4-yl}
m/e 475


benzamide
(M + H) +

978
4-[1-(2,3-dihydro-1,4-benzodioxin-5-ylcarbonyl)
ESI(+))


piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-
m/e 497


ylmethyl)benzamide
(M + H) +

979
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(isoquinolin-4-ylcarbonyl)piperidin-4-yl]
m/e 490


benzamide
(M + H) +

980
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


methyl-1,3-benzoxazol-6-yl)carbonyl]piperidin-
m/e 494


4-yl}benzamide
(M + H) +

981
4-{1-[(1-tert-butyl-3-methyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]
m/e 499


pyridin-7-ylmethyl)benzamide
(M + H) +

982
4-{1-[(1-cyanocyclopentyl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 456


benzamide
(M + H) +

983
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(thieno[3,2-b]pyridin-2-ylcarbonyl)piperidin-
m/e 496


4-yl]benzamide
(M + H) +

984
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(quinolin-7-ylcarbonyl)piperidin-4-yl]
m/e 490


benzamide
(M + H) +

985
4-[1-(5-cyano-2-fluorobenzoyl)piperidin-4-
ESI(+))


yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 482


benzamide
(M + H) +

986
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(5,6,7,8-tetrahydroquinolin-3-ylcarbonyl)
m/e 494


piperidin-4-yl]benzamide
(M + H) +

987
4-[1-(3,4-dihydro-2H-pyrano[2,3-b]pyridin-6-
ESI(+))


ylcarbonyl)piperidin-4-yl]-N-(imidazo[1,2-a]
m/e 496


pyridin-7-ylmethyl)benzamide
(M + H) +

988
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(isoquinolin-7-ylcarbonyl)piperidin-4-yl]
m/e 490


benzamide
(M + H) +

989
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(quinoxalin-2-ylcarbonyl)piperidin-4-yl]
m/e 491


benzamide
(M + H) +

990
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2E)-3-(2-methoxypyridin-3-yl)prop-2-enoyl]
m/e 496


piperidin-4-yl}benzamide
(M + H) +

991
-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2E)-3-(pyridin-2-yl)prop-2-enoyl]piperidin-
m/e 466


4-yl}benzamide
(M + H) +

992
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(8-
ESI(+))


methylimidazo[1,2-a]pyridin-2-yl)carbonyl]
m/e 493


piperidin-4-yl}benzamide
(M + H) +

993
4-{1-[(2-ethoxypyridin-4-yl)carbonyl]piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 484


benzamide
(M + H) +

994
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-
ESI(+))


methyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)
m/e 497


carbonyl]piperidin-4-yl}benzamide
(M + H) +

995
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(4-methyl-4H-furo[3,2-b]pyrrol-5-yl)carbonyl]
m/e 482


piperidin-4-yl}benzamide
(M + H) +

996
4-[1-(3-cyano-5-fluorobenzoyl)piperidin-4-yl]-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 482


benzamide
(M + H) +

997
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(isoquinolin-8-ylcarbonyl)piperidin-4-yl]
m/e 490


benzamide
(M + H) +

998
4-{1-[(4-cyanophenyl)acetyl]piperidin-4-yl}-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 478


benzamide
(M + H) +

999
4-[1-(3-cyano-4-fluorobenzoyl)piperidin-4-yl]-
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 482


benzamide
(M + H) +

1000
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-
ESI(+))


(4,5,6,7-tetrahydro-1,3-benzothiazol-2-
m/e 500


ylcarbonyl)piperidin-4-yl]benzamide
(M + H) +

1001
4-[1-(1,3-benzothiazol-2-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 496


benzamide
(M + H) +

1002
4-{1-[(3-ethyl-1,2-oxazol-5-yl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 458


benzamide
(M + H) +

1003
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
ESI(+))


{[3-methyl-1-(prop-2-en-1-yl)-1H-pyrazol-5-yl]
m/e 483


carbonyl}piperidin-4-yl)benzamide
(M + H) +

1004
4-[1-(1,2,3-benzothiadiazol-5-ylcarbonyl)
ESI(+))


piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-
m/e 497


ylmethyl)benzamide
(M + H) +

1005
4-{1-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 474


ylmethyl)benzamide
(M + H) +

1006
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-
ESI(+))


(propan-2-yl)pyrimidin-4-yl]carbonyl}piperidin-
m/e 483


4-yl)benzamide
(M + H) +

1007
4-{1-[5,6-dimethylpyridin-3-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 468


ylmethyl)benzamide
(M + H) +

1008
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-
ESI(+))


(propan-2-yl)tetrahydro-2H-pyran-4-yl]carbonyl}
m/e 489


piperidin-4-yl)benzamide
(M + H) +

1009
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
ESI(+))


methoxy-6-methylbenzoyl)piperidin-4-yl]
m/e 483


benzamide
(M + H) +

1010
4-[1-(1,3-benzothiazol-7-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 496


benzamide
(M + H) +

1061
4-{1-[(2-chloro-5-fluoropyridin-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 493


ylmethyl)benzamide
(M + H) +

1062
4-{1-[(3-cyclopropyl-1,2-oxazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 471


ylmethyl)benzamide
(M + H) +

1063
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-
ESI(+))


methoxythiophen-2-yl)carbonyl]piperidin-4-yl}
m/e 476


benzamide
(M + H) +

1064
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-
ESI(+))


methyl-5-(propan-2-yl)furan-3-yl]carbonyl}
m/e 486


piperidin-4-yl)benzamide
(M + H) +

1084
4-{1-[2-cyclopropyl-1,3-thiazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 486


ylmethyl)benzamide
(M + H) +

1085
4-[1-(1,3-benzothiazol-5-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 496


benzamide
(M + H) +

1086
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(1-methyl-1H-indazol-6-yl)carbonyl]piperidin-
m/e 493


4-yl}benzamide
(M + H) +

1087
4-{1-[(4-chloro-1,3-dimethyl-1H-pyrazol-5-
ESI(+))


yl)carbonyl]piperidin-4-yl}-N-(imidazo[1,2-a]
m/e 491


pyridin-7-ylmethyl)benzamide
(M + H) +

1088
4-{1-[(5-ethylpyridin-2-yl)carbonyl]piperidin-4-
ESI(+))


yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 468


benzamide
(M + H) +

1089
4-{1-[(3-chloro-5-cyanopyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 499


ylmethyl)benzamide
(M + H) +

1090
4-{1-[(1-cyano-3-methylcyclobutyl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 456


ylmethyl)benzamide
(M + H) +

1091
4-{1-[(1,5-diethyl-1H-1,2,3-triazol-4-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 486


ylmethyl)benzamide
(M + H) +

1092
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(4-
ESI(+))


methoxythiophen-2-yl)carbonyl]piperidin-4-yl}
m/e 475


benzamide
(M + H) +

1093
4-{1-[(5-cyanothiophen-2-yl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 470


benzamide
(M + H) +

1094
4-{1-[(5-cyclopropylpyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-
m/e 480


7-ylmethyl)benzamide
(M + H) +

1095
4-[1-(4-cyano-2,6-difluorobenzoyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 500


benzamide
(M + H) +

1096
4-(1-{[1-ethyl-3-(propan-2-yl)-1H-pyrazol-4-
ESI(+))


yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]
m/e 499


pyridin-7-ylmethyl)benzamide
(M + H) +

1097
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[1-
ESI(+))


(propan-2-yl)-1H-pyrazol-3-yl]acetyl}piperidin-
m/e 485


4-yl)benzamide
M + H) +

1098
4-[1-(1-benzofuran-3-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 479


benzamide
(M + H) +

1099
Example 1099
ESI(+))


N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
m/e 497


[(3-methyl-5,6,7,8-tetrahydroimidazo[1,5-a]
(M + H) +


pyridin-1-yl)carbonyl]piperidin-4-yl}



benzamide


1100
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(4-methoxy-5-methylpyridin-2-yl)carbonyl]
m/e 484


piperidin-4-yl}benzamide
(M + H) +

1101
4-{1-[(1-cyclopentyl-1H-pyrazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 497


ylmethyl)benzamide
(M + H) +

1102
4-{1-[(4-chloro-1,3-thiazol-5-yl)carbonyl]
ESI(+))


piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-
m/e 480


ylmethyl)benzamide
(M + H) +

1103
4-{1-[(3-cyanothiophen-2-yl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 470


benzamide
(M + H) +

1104
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[4-
ESI(+))


(propan-2-yl)pyrimidin-5-yl]carbonyl}piperidin-
m/e 483


4-yl)benzamide
(M + H) +

1105
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-
ESI(+))


methyl-5-propyl-1H-pyrazol-4-yl)carbonyl]
m/e 485


piperidin-4-yl}benzamide
(M + H) +

1106
4-{1-[2-(3-cyclopropyl-1H-pyrazol-1-yl)
ESI(+))


propanoyl]piperidin-4-yl}-N-(imidazo[1,2-a]
m/e 497


pyridin-7-ylmethyl)benzamide
(M + H) +

1107
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
ESI(+))


methyl-2,3-dihydro-1-benzofuran-7-yl)carbonyl]
m/e 495


piperidin-4-yl}benzamide
(M + H) +

1108
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-{[2-
ESI(+))


(propan-2-yl)-1,3-thiazol-4-yl]carbonyl}
m/e 488


piperidin-4-yl)benzamide
(M + H) +

1109
4-(1-{[1-(difluoromethyl)-5-methyl-1H-pyrazol-
ESI(+))


3-yl]carbonyl}piperidin-4-yl)-N-(imidazo[1,2-a]
m/e 493


pyridin-7-ylmethyl)benzamide
(M + H) +

1110
4-{1-[(4-cyanothiophen-2-yl)carbonyl]piperidin-
ESI(+))


4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 470


benzamide
(M + H) +

1111
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4[1-
ESI(+))


(pyrazolo[1,5-a]pyridin-2-ylcarbonyl)piperidin-
m/e 479


4-yl]benzamide
(M + H) +

1112
4-[1-(1-benzofuran-5-ylcarbonyl)piperidin-
ESI(+))


4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)
m/e 479


benzamide
(M + H) +

1113
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
ESI(+))


{[2-(propan-2-yl)-1,3-oxazol-4-yl]carbonyl}
m/e 472


piperidin-4-yl)benzamide
(M + H) +

1114
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2-methoxy-5-methylpyridin-3-yl)carbonyl]
m/e 484


piperidin-4-yl}benzamide
(M + H) +

1115
4-{1-[(5,6-dimethoxypyridin-2-yl)carbonyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 500


ylmethyl)benzamide
(M + H) +

1116
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2-methyl-2H-indazol-4-yl)carbonyl]
m/e 493


piperidin-4-yl}benzamide
(M + H) +

1117
4-{1-[(2-ethylpiperidin-1-yl)(oxo)acetyl]
ESI(+))


piperidin-4-yl}-N-(imidazo[1,2-a]pyridin-7-
m/e 502


ylmethyl)benzamide
(M + H) +

1118
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(2-methyl-2H-indazol-6-yl)carbonyl]
m/e 493


piperidin-4-yl}benzamide
(M + H) +

1119
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-
ESI(+))


[(1-methyl-1H-indazol-4-yl)carbonyl]
m/e 493


piperidin-4-yl}benzamide
(M + H) +

1120
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-
ESI(+))


{[2-(trifluoromethyl)furan-3-yl]carbonyl}
m/e 497


piperidin-4-yl)benzamide
(M + H) +


















































































































































































































































































































































































































































































































































































































Example 240
4-[(4-cyanobenzyl)(3-methoxypropanoyl)amino]-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 215, substituting 3-methoxypropanoyl chloride for 2-cyclopentylacetyl chloride in Example 215B. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.08 (t, J=5.8 Hz, 1H), 8.46 (dd, J=1.9, 0.9 Hz, 1H), 7.94 (dd, J=1.2, 0.6 Hz, 1H), 7.91-7.85 (m, 2H), 7.79-7.73 (m, 2H), 7.56-7.49 (m, 2H), 7.43-7.39 (m, 2H), 7.38-7.33 (m, 2H), 7.20 (dd, J=9.2, 1.7 Hz, 1H), 5.00 (bs, 2H), 4.45 (d, J=5.8 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 3.17 (s, 3H), 2.43-2.35 (m, 2H); MS (ESI(+)) m/e 468 (M+H) + .
Example 241
5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 241A
5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
A solution of 5-bromothiophene-2-carboxylic acid (1.279 g, 6.18 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (1 g, 6.79 mmol), 1-hydroxybenzotriazole hydrate (1.041 g, 6.79 mmol) and N-methylmorpholine (1.698 ml, 15.44 mmol) in dimethylformamide (20 ml) at room temperature was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.131 g, 11.12 mmol). The mixture was stirred overnight and poured into a gently stirred round-bottom flask containing water (100 ml) and ethyl acetate (30 ml). The resulting bilayer suspension was stirred for several minutes, filtered and washed with water then minimal ethyl acetate to give the title compound after drying.
Example 241B
tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
Example 241C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 241D
5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting acetyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.13-9.06 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.72 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.15 (t, J=4.2 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.28-6.21 (m, 1H), 4.46 (d, J=5.9 Hz, 2H), 4.15-4.04 (m, 2H), 3.61 (dt, J=11.3, 5.6 Hz, 2H), 2.63-2.35 (m, 2H), 2.07-1.99 (m, 3H); MS (ESI)(+)) m/e 381 (M+H) + .
Example 242
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting methanesulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.15-9.07 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.51 (s, 1H), 7.38 (bs, 1H), 7.17 (d, J=3.9 Hz, 1H), 6.83 (d, J=7.0 Hz, 1H), 6.28 (bs, 1H), 4.49-4.43 (m, 2H), 3.88-3.82 (m, 2H), 3.29-3.07 (m, 2H), 2.93 (s, 3H), 2.65-2.41 (m, 2H); MS (ESI)(+)) m/e 417 (M+H) + .
Example 246
5-[1-(cyclopropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting cyclopropyl sulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.17 (d, J=3.9 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.28 (bs, 1H), 4.46 (d, J=5.9 Hz, 2H), 3.95-3.89 (m, 2H), 3.43 (t, J=5.7 Hz, 2H), 2.73-2.56 (m, 3H), 1.26-0.89 (m, 4H); MS (ESI)(+)) m/e 443 (M+H) + .
Example 250
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide
A solution of 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide (84 mg, 0.25 mmol), (R)-4-isopropyloxazolidin-2-one (32 mg, 0.25 mmol), N,N-dimethylethane-1,2-diamine (2 mg, 0.025 mmol), copper(I) iodide (5 mg, 0.025 mmol) and potassium carbonate (121 mg, 0.88 mmol) in dioxane (1 ml) was stirred at 110° C. overnight. Concentration and reverse phase chromatography provided the title compound. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.13 (t, J=5.3 Hz, 1H), 8.74 (d, J=5.5 Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.79 (s, 1H), 7.62 (d, J=4.1 Hz, 1H), 7.47 (d, J=7.0 Hz, 1H), 6.77 (d, J=4.2 Hz, 1H), 4.72 (s, 2H), 4.61-4.42 (m, 3H), 2.46 (ddd, J=10.2, 6.9, 3.5 Hz, 1H), 1.00 (d, J=7.0 Hz, 3H), 0.85 (d, J=6.8 Hz, 3H); (APCI(+)) m/e 385 (M+H) + .
Example 257
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide
Example 257A
tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 257B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 257C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methoxyacetyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and methoxyacetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.39 (d, J=7.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (s, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.92 (dd, J=7.1, 1.2 Hz, 1H), 4.58 (bs, 2H), 3.85-3.76 (m, 2H), 3.03 (tt, J=11.8, 3.8 Hz, 1H), 2.97-2.82 (m, 5H), 2.18-2.09 (m, 2H), 1.96 (s, 1H), 1.86-1.71 (m, 2H); MS (ESI(+)) m/e 413 (M+H) + .





TABLE 14



The following Examples were prepared essentially as described in

Example 257, substituting the appropriate carboxylic acid in

Example 257C.





Ex
Name
MS



258
5-(1-acetylpiperidin-4-yl)-N-(imidazo[1,2-a]
(ESI(+))


pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 383



(M + H) +

259
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-
(ESI(+))


methylpropanoyl)piperidin-4-yl]thiophene-2-
m/e 411


carboxamide
(M + H) +

260
5-[1-(cyclopropylcarbonyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 409


carboxamide
(M + H) +

261
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-
(ESI(+))


(tetrahydrofuran-3-ylcarbonyl)piperidin-4-yl]
m/e 439


thiophene-2-carboxamide
(M + H) +

262
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylacetyl)piperidin-4-yl]
m/e 467


thiophene-2-carboxamide
(M + H) +

263
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-
(ESI(+))


methylbutanoyl)piperidin-4-yl]thiophene-2-
m/e 425


carboxamide
(M + H) +

264
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(1,2-
(ESI(+))


oxazol-5-ylcarbonyl)piperidin-4-yl]thiophene-2-
m/e 436


carboxamide
(M + H) +

879
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-
(ESI(+))


methyl-2-(piperazin-1-yl)propanoyl]piperidin-
m/e 495


4-yl}thiophene-2-carboxamide
(M + H) +

887
5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 481


carboxamide
(M + H) +

888
5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 481


carboxamide
(M + H) +




















































Example 266
5-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 250, substituting 5-(hydroxymethyl)oxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.10 (s, 1H), 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.78 (s, 1H), 7.60 (d, J=4.2 Hz, 1H), 7.52-7.41 (m, 1H), 6.60 (d, J=4.2 Hz, 1H), 4.84 (s, 1H), 4.71 (d, J=4.2 Hz, 2H), 4.16 (t, J=9.1 Hz, 1H), 3.98 (dd, J=8.9, 6.2 Hz, 1H), 3.88 (dd, J=12.7, 3.0 Hz, 1H), 3.69 (dd, J=12.7, 3.6 Hz, 1H); (APCI(+)) m/e 373 (M+H) + .
Example 267
5-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 250, substituting (R)-5-hydroxyoxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.10 (t, J=6.1 Hz, 1H), 8.73 (d, J=6.9 Hz, 1H), 8.16 (d, J=1.8 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=4.2 Hz, 1H), 7.46 (d, J=7.7 Hz, 1H), 6.68 (d, J=4.2 Hz, 1H), 4.71 (s, 2H), 4.62 (t, J=5.7 Hz, 1H), 4.15 (dd, J=10.9, 5.3 Hz, 1H), 3.83 (d, J=10.9 Hz, 1H), 2.97 (dd, J=17.7, 6.2 Hz, 1H), 2.50 (d, J=18.2 Hz, 1H); (APCI(+)) m/e 357 (M+H) + .
Example 268
5-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 250, substituting (S)-5-hydroxyoxazolidin-2-one for (R)-4-isopropyloxazolidin-2-one. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.10 (t, J=5.7 Hz, 1H), 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 7.98 (d, J=2.1 Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=4.2 Hz, 1H), 7.46 (d, J=7.0 Hz, 1H), 6.68 (d, J=4.2 Hz, 1H), 4.71 (s, 2H), 4.62 (t, J=5.7 Hz, 1H), 4.15 (dd, J=10.9, 5.3 Hz, 1H), 3.83 (d, J=11.0 Hz, 1H), 2.97 (dd, J=17.6, 6.2 Hz, 1H), 2.50 (d, J=16.8 Hz, 1H); (APCI(+)) m/e 357 (M+H) + .
Example 271
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(methylsulfonyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting methanesulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.39 (d, J=7.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (s, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.92 (dd, J=7.1, 1.2 Hz, 1H), 4.58 (bs, 2H), 3.85-3.76 (m, 2H), 3.03 (tt, J=11.8, 3.8 Hz, 1H), 2.97-2.82 (m, 5H), 2.18-2.09 (m, 2H), 1.96 (s, 1H), 1.86-1.71 (m, 2H); MS (ESI(+)) m/e 419 (M+H) + .
Example 274
N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide
Example 274A
tert-butyl 4-(3-(imidazo[1,2-a]pyridin-6-ylmethyl)ureido)phenylcarbamate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-aminophenylcarbamate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 274B
1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-(imidazo[1,2-a]pyridin-6-ylmethyl)ureido)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 274C
N-(4-{[(imidazo[1,2-a]pyridin-6-ylmethyl)carbamoyl]amino}phenyl)-4-methylpentanamide
The title compound was prepared as described in Example 1A, substituting 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 3-methylbutan-1-amine and 4-methylpentanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.70 (s, 1H), 8.50 (s, 1H), 8.43 (s, 1H), 7.94 (s, 1H), 7.53 (m, 2H), 7.43 (m, 2H), 7.30 (m, 2H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.61 (t, J=5.9 Hz, 1H), 4.28 (d, J=5.8 Hz, 2H), 2.26 (t, J=7.6 Hz, 2H), 1.60-1.40 (m, 3H), 0.89 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 380 (M+H) + .





TABLE 15



The following Examples were prepared essentially as described in

Example 274, substituting the appropriate carboxylic acid in

Example 274C.






Ex
Name
1 H NMR
MS



275
3-cyclopentyl-
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


N-(4-{[(imidazo
ppm 9.69 (s, 1H), 8.48 (s, 1H), 8.43
m/e 406


[1,2-a]pyridin-
(s, 1H), 7.94 (s, 1H), 7.53 (m, 2H),
(M + H) +


6-ylmethyl)
7.43 (m, 2H), 7.30 (m, 2H), 7.20



carbamoyl]
(dd, J = 9.2, 1.7 Hz, 1H), 6.60 (t,



amino}phenyl)
J = 5.9 Hz, 1H), 4.28 (d, J = 5.8 Hz,



propanamide
2H), 2.26 (t, J = 7.6 Hz, 2H), 1.75




(m, 3H), 1.66-1.39 (m, 6H), 1.08




(m, 2H)


276
N-(4-{[(imidazo
1 H NMR (500 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-6-
ppm 9.36 (s, 1H), 8.53 (s, 1H), 8.43
m/e 382


ylmethyl)
(s, 1H), 7.94 (s, 1H), 7.53 (m, 2H),
(M + H) +


carbamoyl]amino}
7.49 (m, 2H), 7.33 (m, 2H), 7.21



phenyl)-2-(propan-
(dd, J = 9.2, 1.7 Hz, 1H), 6.62 (t,



2-yloxy)acetamide
J = 5.9 Hz, 1H), 4.28 (d, J = 5.9 Hz,




2H), 3.97 (s, 2H), 3.67 (m, 1H),




1.16 (d, J = 6.1 Hz, 6H)


277
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-6-
ppm 9.74 (s, 1H), 8.50 (s, 1H),
m/e 394


ylmethyl)
8.44 (d, J = 1.5 Hz, 1H), 7.96 (s,
(M + H) +


carbamoyl]amino}
1H), 7.54 (m, 2H), 7.44 (m, 2H),



phenyl)-2-
7.31 (m, 2H), 7.22 (dd, J = 9.2, 1.7



(tetrahydrofuran-
Hz, 1H), 6.61 (t, J = 5.9 Hz, 1H),



2-yl)acetamide
4.28 (d, J = 5.9 Hz, 2H), 4.12 (m,




1H), 3.74 (m, 1H), 3.60 (m, 1H),




2.47 (m, 1H), 2.39 (m, 1H), 1.98




(m, 1H), 1.81 (m, 2H), 1.49 (m,




1H)


278
N-(4-{[(imidazo
1 H NMR (500 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-
ppm 9.72 (s, 1H), 8.50 (s, 1H),
m/e 408


6-ylmethyl)
8.43 (s, 1H), 7.94 (s, 1H), 7.53 (m,
(M + H) +


carbamoyl]amino}
2H), 7.43 (m, 2H), 7.31 (m, 2H),



phenyl)-2-
7.21 (dd, J = 9.2, 1.7 Hz, 1H), 6.60



(tetrahydro-2H-
(t, J = 5.9 Hz, 1H), 4.28 (d, J = 5.9



pyran-4-yl)
Hz, 2H), 3.82 (m, 2H), 3.29 (m,



acetamide
2H), 2.20 (d, J = 7.1 Hz, 2H), 2.01




(m, 1H), 1.57 (m, 2H), 1.25 (m,




2H)


279
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-
ppm 9.73 (s, 1H), 8.49 (s, 1H),
m/e 414


6-ylmethyl)
8.42 (s, 1H), 7.94 (s, 1H), 7.53
(M + H) +


carbamoyl]amino}
(m, 2H), 7.42 (m, 2H), 7.35-7.15



phenyl)-3-
(m, 8H), 6.60 (t, J = 5.9 Hz, 1H),



phenylpropanamide
4.28 (d, J = 5.8 Hz, 2H), 2.89 (t, J =




7.3 Hz, 2H), 2.57 (t, J = 5.7 Hz,




2H)


280
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-7-
ppm 9.69 (s, 1H), 8.52 (s, 1H),
m/e 380


ylmethyl)
8.47 (d, J = 7.0 Hz, 1H), 7.87 (s,
(M + H) +


carbamoyl]amino}
1H), 7.50 (bs, 1H), 7.42 (m, 2H),



phenyl)-4-
7.37 (s, 1H), 7.30 (m, 2H), 6.82



methylpentanamide
(dd, J = 7.0, 1.5 Hz, 1H), 6.63 (t,




J = 6.0 Hz, 1H), 4.31 (d, J = 5.9




Hz, 2H), 2.25 (t, J = 7.6 Hz, 2H),




1.60-1.41 (m, 3H), 0.88 (d, J =




6.4 Hz, 6H)


281
3-cyclopentyl-
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


N-(4-{[(imidazo
ppm 9.69 (s, 1H), 8.53 (s, 1H),
m/e 406


[1,2-a]pyridin-
8.48 (d, J = 6.9 Hz, 1H), 7.88 (bs,
(M + H) +


7-ylmethyl)
1H), 7.52 (bs, 1H), 7.44 (m, 2H),



carbamoyl]amino}
7.37 (s, 1H), 7.31 (m, 2H), 6.83



phenyl)
(dd, J = 6.9, 1.4 Hz, 1H), 6.64 (t,



propanamide
J = 6.0 Hz, 1H), 4.32 (d, J = 5.9




Hz, 2H), 2.27 (t, J = 7.6 Hz, 2H),




1.74 (m, 3H), 1.65-1.40 (m, 6H),




1.09 (m, 2H)


282
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-
ppm 9.37 (s, 1H), 8.59 (s, 1H),
m/e 382


7-ylmethyl)
8.49 (m, 1H), 7.89 (s, 1H), 7.50
(M + H) +


carbamoyl]amino}
(m, 3H), 7.39 (s, 1H), 7.34 (m,



phenyl)-2-(propan-
2H), 6.84 (dd, J = 6.9, 1.6 Hz, 1H),



2-yloxy)acetamide
6.68 (t, J = 6.0 Hz, 1H), 4.33 (d,




J = 6.0 Hz, 2H), 3.98 (s, 2H), 3.67




(m, 1H), 1.16 (d, J = 6.1 Hz, 6H)


283
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-7-
ppm 9.73 (s, 1H), 8.54 (s, 1H),
m/e 394


ylmethyl)
8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
(M + H) +


carbamoyl]amino}
1H), 7.51 (s, 1H), 7.44 (m, 2H),



phenyl)-2-
7.38 (bs, 1H), 7.32 (m, 2H), 6.83



(tetrahydrofuran-
(dd, J = 6.9, 1.6 Hz, 1H), 6.65 (t,



2-yl)acetamide
J = 6.0 Hz, 1H), 4.32 (d, J = 5.9




Hz, 2H), 4.16 (m, 1H), 3.76 (m,




1H), 3.60 (m, 1H), 2.50 (m, 1H),




2.39 (m, 1H), 1.99 (m, 1H), 1.83




(m, 2H), 1.53 (m, 1H)


284
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-
ppm 9.72 (s, 1H), 8.53 (s, 1H),
m/e 408


7-ylmethyl)
8.48 (d, J = 6.9 Hz, 1H), 7.88 (bs,
(M + H) +


carbamoyl]amino}
1H), 7.51, (bs, 1H), 7.44 (m, 2H),



phenyl)-2-
7.38 (bs, 1H), 7.32 (m, 2H), 6.83



(tetrahydro-2H-
(m, 1H), 6.65 (m, 1H), 4.32 (m,



pyran-4-yl)
2H), 3.82 (m, 2H), 3.33 (m, 2H),



acetamide
2.20 (d, J = 7.1 Hz, 2H), 1.97 (m,




1H), 1.58 (m, 2H), 1.23 (m, 2H)


285
N-(4-{[(imidazo
1 H NMR (400 MHz, DMSO-d 6 ) δ
(ESI(+))


[1,2-a]pyridin-
ppm 9.74 (s, 1H), 8.54 (s, 1H),
m/e 414


7-ylmethyl)
8.49 (d, J = 6.9 Hz, 1H), 7.89
(M + H) +


carbamoyl]amino}
(bs, 1H), 7.52 (bs, 1H), 7.42 (m,



phenyl)-3-
3H), 7.35-7.22 (m, 6H), 7.17 (m,



phenylpropanamide
1H), 6.84 (d, J = 7.6 Hz, 1H),




6.65 (t, J = 6.0 Hz, 1H), 4.32 (d,




J = 5.9 Hz, 2H), 2.90 (t, J = 7.7




Hz, 2H), 2.58 (t, J = 7.7 Hz, 2H)





























































































































Example 290
tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate
Example 290A
1-(4-bromo-2-fluorophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1C, substituting 4-bromo-2-fluoroaniline for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 290B
tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromo-2-fluorophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.53-8.46 (m, 2H), 8.09 (t, J=8.7 Hz, 1H), 7.91-7.88 (m, 1H), 7.54-7.50 (m, 1H), 7.42-7.37 (m, 1H), 7.33-7.24 (m, 1H), 7.21-7.08 (m, 2H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.17-6.10 (m, 1H), 4.35 (d, J=5.8 Hz, 2H), 4.01-3.94 (m, 2H), 3.55-3.47 (m, 2H), 2.46-2.36 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 466 (M+H) + .
Example 291
tert-butyl (3S)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate
Example 291A
(S)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate
(S)-Tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.4 mmol) was dissolved in 1-fluoro-4-nitrobenzene (13.94 g, 99 mmol). An aqueous solution of 5.9N potassium hydroxide (77 ml, 452 mmol) was added followed by addition of tetrabutylammonium bromide (2.238 g, 6.94 mmol). The reaction mixture was stirred at 40° C. for 24 hours and then cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated to give the title compound.
Example 291B
(S)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting (S)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 291C
tert-butyl (3S)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting (S)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.51-8.44 (m, 2H), 7.88-7.86 (m, 1H), 7.53-7.49 (m, 1H), 7.40-7.27 (m, 3H), 6.86-6.80 (m, 3H), 6.63 (t, J=6.0 Hz, 1H), 4.93-4.84 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.55-3.28 (m, 4H), 2.16-1.94 (m, 2H), 1.42-1.36 (m, 9H); MS (ESI(+)) m/e 452 (M+H) + .
Example 292
tert-butyl {2-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}carbamate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(tert-butoxycarbonylamino)-3-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.26 (s, 1H), 9.08 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91-7.78 (m, 2H), 7.76-7.68 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (bs, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 385 (M+H) + .
Example 297
2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
Example 297A
tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline.
Example 297B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 297C
2-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.27 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.1 Hz, 1H), 8.41 (s, 1H), 7.89 (s, 1H), 7.38-7.56 (m, 7H), 6.85 (dd, J=6.8, 1.7 Hz, 1H), 6.56-6.89 (m, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.08-4.40 (m, 2H), 3.74-3.92 (m, 1H), 3.44-3.66 (m, 1H), 2.66 (s, 2H); MS (ESI(+)) m/e 444 (M+H) + .
Example 298
4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
Example 298A
4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-bromobenzoic acid for 4-nitrobenzoic acid.
Example 298B
4-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 51A, substituting 1-(2-hydroxy-2-methylpropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.19 (d, J=0.8 Hz, 1H), 7.97 (d, J=0.7 Hz, 1H), 7.95-7.86 (m, 3H), 7.73-7.66 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.37 (m, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.73 (s, 1H), 4.51 (d, J=5.8 Hz, 2H), 4.04 (s, 2H), 1.10 (s, 6H); MS (ESI(+)) m/e 390 (M+H) + .
Example 299
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-phenylthiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.14 (t, J=6.0 Hz, 1H), 8.50 (dd, J=7.1, 0.7 Hz, 1H), 7.91-7.88 (m, 1H), 7.84 (d, J=3.9 Hz, 1H), 7.72 (dt, J=8.3, 2.4 Hz, 2H), 7.57 (d, J=3.9 Hz, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.49-7.33 (m, 4H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 334 (M+H).
Example 301
tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.06 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.87 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (m, 3H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.72 (dd, J=10.3, 7.5 Hz, 1H), 3.47 (m, 2H), 3.20 (m, 2H), 2.21 (m, 1H), 1.97 (m, 1H), 1.41 (m, 9H); (ESI(+)) m/e 421 (M+H) + .
Example 302
tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.61 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (d, J=1.1 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.36 (m, 3H), 7.14 (m, 2H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 3.65 (dd, J=10.2, 7.5 Hz, 1H), 3.46 (m, 1H), 3.21 (m, 2H), 3.09 (m, 1H), 2.12 (m, 1H), 1.89 (m, 1H), 1.41 (m, 9H); (ESI(+)) m/e 436 (M+H) + .
Example 303
N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide
Example 303A
tert-butyl 4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenylcarbamate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-aminophenylcarbamate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 303B
1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenylcarbamate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 303C
N-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)biphenyl-2-sulfonamide
In a 4 mL vial was mixed 1-(4-aminophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea (50 mg, 0.178 mmol) in anhydrous tetrahydrofuran (2 mL). To this mixture at room temperature was added 60% sodium hydride (24.88 mg, 0.622 mmol). The reaction was stirred about 30 minutes and biphenyl-2-sulfonyl chloride (53.9 mg, 0.213 mmol) was added. The reaction mixture stirred overnight at room temperature and was quenched with saturated ammonium chloride and water. The aqueous solution was extracted with dichloromethane and 10% methanol/dichloromethane. The organic layers were combined, concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.74 (bs, 1H), 8.56 (s, 1H), 8.47 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (dd, J=7.8, 1.4 Hz, 1H), 7.87 (dd, J=1.2, 0.6 Hz, 1H), 7.62 (m, 1H), 7.54 (m, 1H), 7.51 (m, 1H), 7.38 (m, 4H), 7.30-7.20 (m, 5H), 6.82 (m, 3H), 6.66 (t, J=6.0 Hz, 1H), 4.30 (d, J=6.0 Hz, 2H); (ESI(+)) m/e 498 (M+H) + .
Example 306
1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
Example 306A
1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 306B
1-{2-fluoro-4-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, methanol-d 4 ) δ ppm 8.74 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.00-7.96 (m, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.81-7.77 (m, 1H), 7.50-7.44 (m, 1H), 7.28-7.16 (m, 2H), 6.17-6.11 (m, 1H), 4.61 (bs, 2H), 4.30-4.15 (m, 2H), 3.79 (t, J=5.7 Hz, 2H), 3.08-2.90 (m, 1H), 2.62-2.45 (m, 2H), 1.17-1.08 (m, 6H); MS (ESI(+)) m/e 436 (M+H) + .
Example 307
1-{2-fluoro-4-[1-(tetrahydrofuran-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and tetrahydrofuran-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, methanol-d 4 ) δ ppm 8.74 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.80 (bs, 1H), 7.47 (dd, J=7.0, 1.5 Hz, 1H), 7.28-7.16 (m, 2H), 6.17-6.09 (m, 1H), 4.84-4.70 (m, 1H), 4.61 (bs, 2H), 4.34-4.12 (m, 2H), 4.01-3.68 (m, 4H), 2.67-2.47 (m, 2H), 2.29-1.88 (m, 4H); MS (ESI(+)) m/e 464 (M+H) + .
Example 314
tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
Example 314A
2-(4-bromophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 2-(4-bromophenyl)acetic acid for 4-nitrobenzoic acid.
Example 314B
tert-butyl 4-{4-[2-(imidazo[1,2-a]pyridin-6-ylamino)-2-oxoethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-(4-bromophenyl)-N-(imidazo[1,2-a]pyridin-6-yl)acetamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 10.25 (s, 1H), 9.20-9.16 (m, 1H), 7.98-7.94 (m, 1H), 7.58-7.48 (m, 2H), 7.44-7.36 (m, 2H), 7.35-7.28 (m, 2H), 7.16 (dd, J=9.6, 2.0 Hz, 1H), 6.16-6.09 (m, 1H), 4.05-3.94 (m, 2H), 3.66 (s, 2H), 3.53 (t, J=5.7 Hz, 2H), 2.49-2.40 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 433 (M+H) + .
Example 315
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]benzamide
The title compound was prepared as described in Example 51A, substituting 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.27 (s, 1H), 8.00-7.86 (m, 4H), 7.69 (d, J=8.4 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.5 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 3.94 (d, J=7.1 Hz, 2H), 2.15 (dp, J=13.6, 6.8 Hz, 1H), 0.87 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 374 (M+H) + .
Example 318
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(propan-2-yloxy)phenyl]thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 2-(3-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 8.19 (d, J=0.4 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.86 (d, J=0.5 Hz, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.24 (d, J=3.9 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 4.13 (d, J=6.6 Hz, 2H), 3.09-2.83 (m, 4H), 2.47-2.40 (m, 1H), 2.14-1.96 (m, 1H), 1.88-1.69 (m, 1H), 1.69-1.54 (m, 1H), 1.37-1.14 (m, 1H).
Example 319
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.26 (t, J=5.9 Hz, 1H), 8.50 (d, J=6.8 Hz, 1H), 8.40 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.42 (s, 1H), 6.84 (dd, J=7.1, 1.7 Hz, 1H), 6.72-6.79 (m, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.32 (s, 1H), 4.16 (s, 1H), 3.81-3.89 (m, 2H), 3.73 (s, 2H), 3.36-3.47 (m, 1H), 2.83-3.05 (m, 1H), 2.65 (s, 1H), 2.38-2.54 (m, 2H), 1.50-1.69 (m, 4H); MS (ESI(+)) m/e 452 (M+H) + .
Example 320
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.26 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.1 Hz, 1H), 8.40 (s, 1H), 7.89 (s, 1H), 7.53 (s, 1H), 7.42 (s, 1H), 6.84 (dd, J=7.1, 1.7 Hz, 1H), 6.76 (s, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.29 (s, 1H), 4.16 (s, 1H), 3.62-3.74 (m, 2H), 2.81-3.03 (m, 1H), 2.60-2.69 (m, 1H), 2.50-2.58 (m, 1H), 1.02 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 410 (M+H) + .
Example 321
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide
Example 321A
(S)-tert-butyl 3-(4-(benzyloxycarbonyl)phenoxy)pyrrolidine-1-carboxylate
To a stirred solution of (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (1 g, 5.34 mmol) in tetrahydrofuran (38.1 ml) was added benzyl 4-hydroxybenzoate (1.341 g, 5.87 mmol) and triphenylphpsphine polymer bound (4.45 g, 8.01 mmol). The reaction mixture was cooled to 0° C. and a solution of (E)-diisopropyl diazene-1,2-dicarboxylate (1.367 ml, 6.94 mmol) in tetrahydrofuran (5 mL) was added dropwise over 15 minutes. The reaction was allowed to stir at room temperature for 16 hours and the mixture was filtered. The solids were washed with dichloromethane, and the combined filtrates were concentrated and purified by normal phase chromatography to give the title compound.
Example 321B
(S)-4-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)benzoic acid
The title compound was prepared as described in Example 1B, substituting (R)-tert-butyl 3-(4-(benzyloxycarbonyl)phenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 321C
(S)-tert-butyl 3-(4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (S)-4-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)benzoic acid for 4-nitrobenzoic acid.
Example 321D
(S)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide
The title compound was prepared as described in Example 28A, substituting (S)-tert-butyl 3-(4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)phenoxy)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate.
Example 321E
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide
The title compound was prepared as described in Example 1A, substituting (S)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 , Temp=90° C.) δ ppm 8.67-8.59 (m, 1H), 8.41 (d, J=6.9 Hz, 1H), 7.90-7.84 (m, 2H), 7.81 (s, 1H), 7.50-7.46 (m, 1H), 7.38 (s, 1H), 7.03-6.97 (m, 2H), 6.83 (dd, J=6.9, 1.7 Hz, 1H), 5.17-5.04 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.91-3.36 (m, 5H), 2.31-1.98 (m, 2H), 1.63-1.49 (m, 1H), 1.38-1.23 (m, 1H), 1.00 (d, J=6.7 Hz, 3H), 0.89-0.74 (m, 3H); MS (ESI(+)) m/e 421 (M+H) + .





TABLE 16



The following Examples were prepared essentially as described

in Example 321, substituting the appropriate

carboxylic acid in Example 321E.





Ex
Name
MS



339
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3R)-
(ESI(+))


tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-
m/e 435


yl}oxy)benzamide
(M + H) +

340
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2R)-
(ESI(+))


tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-
m/e 435


yl}oxy)benzamide
(M + H) +

341
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(2S)-
(ESI(+))


tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-
m/e 435


yl}oxy)benzamide
(M + H) +

342
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-
m/e 449


yl]oxy}benzamide
(M + H) +

343
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-
m/e 463


yl]oxy}benzamide
(M + H) +

346
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3S)-1-[(3S)-
(ESI(+))


tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-
m/e 435


yl}oxy)benzamide
(M + H) +

347
4-{[(3S)-1-(cyclopropylacetyl)pyrrolidin-3-yl]oxy}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 419



(M + H) +

348
4-{[(3S)-1-(2-hydroxy-2-methylpropanoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 423



(M + H) +

349
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(3-
(ESI(+))


methoxy-2-methylpropanoyl)pyrrolidin-3-
m/e 437


yl]oxy}benzamide
(M + H) +

350
4-{[(3S)-1-butanoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 407



(M + H) +

351
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3S)-1-(2-
(ESI(+))


methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide
m/e 407



(M + H) +

352
4-{[(3S)-1-(cyclopropylcarbonyl)pyrrolidin-3-yl]oxy}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 405



(M + H) +

353
4-{[(3S)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 441



(M + H) +

354
4-{[(3S)-1-(3-hydroxy-3-methylbutanoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 437



(M + H) +
































































Example 322
tert-butyl 4-[4-(imidazo[1,2-a]pyridin-7-ylcarbamoyl)phenyl]piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-amine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 10.36 (s, 1H), 8.47 (d, J=7.3 Hz, 1H), 8.15-8.10 (m, 1H), 7.94-7.87 (m, 2H), 7.83 (s, 1H), 7.50-7.40 (m, 3H), 7.24 (dd, J=7.3, 2.1 Hz, 1H), 4.16-4.05 (m, 2H), 2.94-2.66 (m, 3H), 1.84-1.73 (m, 2H), 1.65-1.41 (m, 11H); MS (ESI(+)) m/e 421 (M+H) + .
Example 323
tert-butyl 4-[4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl]piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-amine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 10.27 (s, 1H), 9.36-9.31 (m, 1H), 8.03 (s, 1H), 7.95-7.88 (m, 2H), 7.60-7.52 (m, 2H), 7.47-7.35 (m, 3H), 4.15-4.04 (m, 2H), 2.95-2.66 (m, 3H), 1.83-1.73 (m, 2H), 1.65-1.45 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 421 (M+H) + .
Example 324
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(2-methylpropanoyl)amino]oxetan-3-yl}thiophene-2-carboxamide
Example 324A
5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)thiophene-2-carboxylic acid
Butyllithium (6.16 ml, 15.41 mmol) was added dropwise to a stirred solution of diisopropylamine (1.919 ml, 13.69 mmol) in tetrahydrofuran (10 ml) at −78° C. The solution was allowed to warm to room temperature and then added dropwise by syringe to a stirred −78° C. solution of thiophene-2-carboxylic acid (0.877 g, 6.85 mmol) in tetrahydrofuran (30 ml). The resulting suspension was stirred for 40 minutes at −78° C. when a solution of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g, 5.71 mmol) in tetrahydrofuran (10 ml) was added dropwise. After the addition was complete, the reaction mixture was allowed to warm to room temperature, quenched with saturated ammonium chloride and diluted with a water to dissolve the remaining solids. The aqueous solution was extracted with ethyl acetate, adjusted to pH 2 by addition of 1N aqueous hydrochloric acid and re-extracted with ethyl acetate and methylene chloride. The organic extracts were dried with magnesium sulfate, filtered, concentrated and purified by normal phase chromatography to give the title compound.
Example 324B
5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 324C
5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
5-(3-(1,1-Dimethylethylsulfinamido)oxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide (432 mg, 1 mmol) in 10 ml methanol was treated with 4N aqueous HCl in dioxane (0.75 ml, 3 mmol) and the mixture was stirred for 2 hours. Concentration provided the title compound.
Example 324D
The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.03-9.10 (m, 2H), 8.48 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.71 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 6.83 (dd, J=6.9, 1.8 Hz, 1H), 4.80 (d, J=6.7 Hz, 2H), 4.71 (d, J=6.7 Hz, 2H), 4.46 (d, J=6.0 Hz, 2H), 2.40-2.48 (m, 1H), 1.05 (d, J=7.1 Hz, 6H); MS (ESI(+)) m/e 399 (M+H) + .
Example 325
5-[3-(benzoylamino)oxetan-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.70 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.47 (d, J=6.8 Hz, 1H), 7.87-7.93 (m, 3H), 7.72 (d, J=3.7 Hz, 1H), 7.56-7.62 (m, 1H), 7.48-7.55 (m, 3H), 7.37 (s, 1H), 7.29 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.1, 1.7 Hz, 1H), 5.01 (d, J=6.8 Hz, 2H), 4.80 (d, J=7.1 Hz, 2H), 4.45 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 433 (M+H) + .
Example 326
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{3-[(tetrahydrofuran-3-ylacetyl)amino]oxetan-3-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-(tetrahydrofuran-3-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.22 (s, 1H), 9.07 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.71 (d, J=3.6 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.22 (d, J=4.0 Hz, 1H), 6.83 (dd, J=7.1, 1.6 Hz, 1H), 4.81 (d, J=6.7 Hz, 2H), 4.72 (d, J=6.7 Hz, 2H), 4.46 (d, J=6.0 Hz, 2H), 3.56-3.80 (m, 3H), 2.23-2.30 (m, 2H), 1.89-2.04 (m, 1H), 1.45-1.58 (m, 1H); MS (ESI(+)) m/e 441 (M+H) + .
Example 327
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[3-(pentanoylamino)oxetan-3-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and pentanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.11 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.48 (dd, J=7.0, 0.8 Hz, 1H), 7.88 (s, 1H), 7.70 (d, J=4.1 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.21 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.80 (d, J=6.8 Hz, 2H), 4.71 (d, J=6.8 Hz, 2H), 4.46 (d, J=5.8 Hz, 2H), 2.17 (t, J=7.5 Hz, 2H), 1.44-1.57 (m, 2H), 1.22-1.37 (m, 2H), 0.84-0.92 (m, 3H); MS (ESI(+)) m/e 413 (M+H) + .
Example 328
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3S)-1-[(25)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea
Example 328A
(R)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate
(R)-Tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.4 mmol) was dissolved in 1-fluoro-4-nitrobenzene (13.94 g, 99 mmol). An aqueous solution of 5.9N potassium hydroxide (77 ml, 452 mmol) was added followed by addition of tetrabutylammonium bromide (2.238 g, 6.94 mmol). The reaction mixture was stirred at 40° C. for 24 hours, cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated to give the title compound.
Example 328B
(R)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting (R)-tert-butyl 3-(4-nitrophenoxy)pyrrolidine-1-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 328C
tert-butyl (3S)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting (R)-tert-butyl 3-(4-aminophenoxy)pyrrolidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 328D
(R)-1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yloxy)phenyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl (3S)-3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 328E
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3S)-1-[(25)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)phenyl]urea
The title compound was prepared as described in Example 1A, substituting (R)-1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yloxy)phenyl)urea for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.76-8.70 (m, 1H), 8.19-8.12 (m, 1H), 8.00-7.94 (m, 1H), 7.81-7.75 (m, 1H), 7.46 (d, J=7.0 Hz, 1H), 7.34-7.25 (m, 2H), 6.92-6.82 (m, 2H), 5.07-4.95 (m, 1H), 4.58 (bs, 2H), 3.84-3.61 (m, 3H), 3.60-3.45 (m, 1H), 2.67-2.45 (m, 1H), 2.31-2.06 (m, 2H), 1.72-1.57 (m, 1H), 1.50-1.35 (m, 1H), 1.12-1.00 (m, 3H), 0.94-0.85 (m, 3H); MS (ESI(+)) m/e 436 (M+H) + .





TABLE 17



The following Examples were prepared essentially as described

in Example 328, substituting the appropriate alcohol in Example 328A

and the appropriate carboxylic acid in Example 328E.





Ex
Name
MS



329
1-(4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}phenyl)-3-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 456



(M + H) +

330
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-(2-
(ESI(+))


methylpropanoyl)pyrrolidin-3-yl]oxy}phenyl)urea
m/e 422



(M + H) +

331
1-(4-{[(3R)-1-(cyclopropylcarbonyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 420


ylmethyl)urea
(M + H) +

332
1-(4-{[(3R)-1-(cyclopropylacetyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 434


ylmethyl)urea
(M + H) +

333
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylcarbonyl)pyrrolidin-3-
m/e 464


yl]oxy}phenyl)urea
(M + H) +

334
1-(4-{[(3R)-1-(2-hydroxy-2-methylpropanoyl)pyrrol-
(ESI(+))


idin-3-yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 438


ylmethyl)urea
(M + H) +

335
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-
(ESI(+))


[(2R)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-
m/e 450


yl}oxy)phenyl]urea
(M + H) +

336
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-1-
(ESI(+))


[(2S)-tetrahydrofuran-2-ylcarbonyl]pyrrolidin-3-
m/e 450


yl}oxy)phenyl]urea
(M + H) +

337
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-
(ESI(+))


(tetrahydrofuran-3-ylcarbonyl)pyrrolidin-3-
m/e 450


yl]oxy}phenyl)urea
(M + H) +

338
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[(3R)-1-
(ESI(+))


(tetrahydro-2H-pyran-4-ylacetyl)pyrrolidin-3-
m/e 478


yl]oxy}phenyl)urea
(M + H) +

689
1-(4-{[(3R)-1-(2-fluorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 474


ylmethyl)urea
(M + H) +

690
1-(4-{[(3R)-1-(3-fluorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 474


ylmethyl)urea
(M + H) +

691
1-(4-{[(3R)-1-(4-fluorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 474


ylmethyl)urea
(M + H) +

692
1-(4-{[(3R)-1-(2,4-difluorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 492


ylmethyl)urea
(M + H) +

693
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-({(3R)-
(ESI(+))


1-[4-(trifluoromethyl)benzoyl]pyrrolidin-3-
m/e 524


yl}oxy)phenyl]urea
(M + H) +

694
1-(4-{[(3R)-1-(3,5-difluorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 492


ylmethyl)urea
(M + H) +

695
1-(4-{[(3R)-1-(2-chlorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 490


ylmethyl)urea
(M + H) +

696
1-(4-{[(3R)-1-(4-chlorobenzoyl)pyrrolidin-3-
(ESI(+))


yl]oxy}phenyl)-3-(imidazo[1,2-a]pyridin-7-
m/e 490


ylmethyl)urea
(M + H) +












































































Example 355
2-(4-benzoylpiperazin-1-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting phenyl(piperazin-1-yl)methanone for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.86 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.7 Hz, 1H), 7.90 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.50 (m, 5H), 7.37 (s, 1H), 6.82 (dd, J=7.1, 1.6 Hz, 1H), 4.43 (d, J=5.6 Hz, 2H), 3.41-3.82 (m, 8H); MS (ESI(+)) m/e 447 (M+H) + .
Example 356
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(propan-2-yl)piperazin-1-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting 1-isopropylpiperazine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.80 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 6.81 (dd, J=7.1, 1.7 Hz, 1H), 4.42 (d, J=6.1 Hz, 2H), 3.41-3.48 (m, 4H), 2.64-2.79 (m, 1H), 2.51-2.57 (m, 4H), 0.98 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 385 (M+H) + .
Example 357
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[4-(2-methoxyethyl)piperazin-1-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as in Example 53B, substituting 1-(2-methoxyethyl)piperazine for 4-cyanobenzylamine and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 2-bromo-N-(imidazo[1,2-a]pyridin-6-yl)thiazole-5-carboxamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.82 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.7 Hz, 1H), 7.88 (s, 1H), 7.88 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.81 (dd, J=7.1, 1.6 Hz, 1H), 4.43 (d, J=6.0 Hz, 2H), 3.42-3.48 (m, 6H), 3.24 (s, 3H), 2.51-2.56 (m, 6H); MS (ESI(+)) m/e 401 (M+H) + .
Example 358
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide
Example 358A
methyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
Example 358B
4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 358C
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide
The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.15 (t, J=5.8 Hz, 1H), 8.55-8.47 (m, 2H), 8.00-7.84 (m, 5H), 7.54 (dd, J=5.1, 4.1 Hz, 2H), 7.23 (dd, J=9.3, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 3.30-3.21 (m, 2H), 1.62 (dp, J=13.3, 6.6 Hz, 1H), 1.49-1.37 (m, 2H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 365 (M+H) + .
Example 359
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide
The title compound was prepared as described in Example 1A, substituting (S)-(tetrahydrofuran-3-yl)methanamine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-6-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.15 (t, J=5.8 Hz, 1H), 8.68 (t, J=5.7 Hz, 1H), 8.49 (bs, 1H), 8.03-7.85 (m, 5H), 7.58-7.50 (m, 2H), 7.23 (dd, J=9.1, 1.7 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 3.80-3.56 (m, 4H), 3.48 (dd, J=8.5, 5.2 Hz, 1H), 3.28-3.17 (m, 1H), 2.03-1.87 (m, 1H), 1.68-1.46 (m, 1H), 1.37-1.09 (m, 1H); MS (ESI(+)) m/e 379 (M+H) + .
Example 360
1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea
Example 360A
1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea
The title compound was prepared as described in Example 3A, substituting 1-isocyanato-4-bromobenzene for 1-isocyanato-4-nitrobenzene and imidazo[1,2-a]pyridin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 360B
1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea
The title compound was prepared as described in Example 51A, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.59 (s, 1H), 8.44 (s, 1H), 8.04 (s, 1H), 7.95 (s, 1H), 7.76 (s, 1H), 7.57-7.50 (m, 2H), 7.48-7.32 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.65 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 4.04 (t, J=6.9 Hz, 2H), 1.87-1.73 (m, 2H), 0.84 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 375 (M+H) + .
Example 361
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-phenyl-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 51A, substituting phenyl boronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.34 (t, J=5.8 Hz, 1H), 8.56-8.48 (m, 2H), 8.05-7.95 (m, 2H), 7.90 (d, J=0.8 Hz, 1H), 7.60-7.49 (m, 4H), 7.45 (s, 1H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 4.52 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 335 (M+H).
Example 362
1-(imidazo[1,2-a]pyridin-6-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 51A, substituting 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-6-ylmethyl)urea for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.59 (s, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.03 (d, J=0.8 Hz, 1H), 7.97-7.93 (m, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.57-7.50 (m, 2H), 7.44-7.35 (m, 4H), 7.21 (dd, J=9.2, 1.7 Hz, 1H), 6.65 (t, J=5.9 Hz, 1H), 4.30 (d, J=5.8 Hz, 2H), 3.90 (d, J=7.2 Hz, 2H), 2.19-2.06 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 389 (M+H) + .
Example 364
tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)azetidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66 (s, 1H), 8.48 (m, 1H), 7.88 (s, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.39 (m, 3H), 7.19 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.20 (m, 2H), 3.78 (m, 2H), 3.71 (m, 1H), 1.40 (s, 9H); (ESI(+)) m/e 422 (M+H) + .
Example 365
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.95 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.06 (m, 2H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.67 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.67 (m, 2H), 3.18 (m, 2H), 1.92 (m, 2H), 1.52 (m, 2H), 1.41 (s, 9H); (ESI(+)) m/e 451 (M+H) + .
Example 366
tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.47 (m, 2H), 7.88 (d, J=1.1 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.30 (m, 2H), 6.85 (m, 3H), 6.62 (t, J=6.0 Hz, 1H), 4.42 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.64 (m, 2H), 3.15 (m, 2H), 1.86 (m, 2H), 1.51 (m, 2H), 1.40 (s, 9H); (ESI(+)) m/e 466 (M+H) + .
Example 367
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide
Example 367A
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 367B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)pyrrolidin-3-yl]benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.07 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.42 (m, 3H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.90-3.66 (m, 1H), 3.63-3.20 (m, 4H), 2.70 (m, 1H), 2.38-2.18 (m, 1H), 2.10-1.90 (m, 1H), 1.01 (m, 6H); (ESI(+)) m/e 391 (M+H) + .





TABLE 18



The following Examples were prepared essentially

as described in Example 367, substituting

the appropriate carboxylic acid in Example 367B.






Ex
Name
1 H NMR
MS



368
N-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 405


ylmethyl)-4-{1-
7.87 (m, 3H), 7.52 (d, J = 1.2 Hz, 1H),
(M + H) +


[(2S)-2-
7.41 (m, 3H), 6.85 (dd, J = 7.0, 1.6 Hz,



methylbutan-
1H), 4.50 (d, J = 5.9 Hz, 2H), 3.90-3.66



oyl]pyrrolidin-3-
(m, 1H), 3.63-3.20 (m, 4H), 2.51 (m,



yl}benzamide
1H), 2.38-2.18 (m, 1H), 2.10-1.90 (m,




1H), 1.57 (m, 1H), 1.34 (m, 1H),




1.01 (m, 3H), 0.86 (m, 3H)


369
4-[1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


(cyclopropylacet-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 403


yl)pyrrolidin-3-
7.88 (m, 3H), 7.52 (d, J = 1.2 Hz, 1H),
(M + H) +


yl]-N-(imida-
7.42 (m, 3H), 6.85 (dd, J = 7.0, 1.6 Hz,



zo[1,2-a]pyridin-
1H), 4.50 (d, J = 5.9 Hz, 2H), 3.88 (m,



7-ylmethyl)ben-
1H), 3.61 (m, 1H), 3.60-3.20 (m, 3H),



zamide
2.35-2.15 (m, 3H), 2.10-1.88 (m, 1H),




1.99 (m, 1H), 0.44 (m, 2H), 0.12




(m, 2H)


370
4-(1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


benzoylpyrrolidin-
9.07 (m, 1H), 8.48 (t, J = 6.2 Hz, 1H),
m/e 425


3-yl)-N-
7.88 (m, 3H), 7.55 (m, 2H), 7.54-7.34
(M + H) +


(imidazo[1,2-a]py-
(m, 7H), 6.85 (m, 1H), 4.50 (m, 2H),



ridin-7-ylmeth-
4.00 (m, 1H), 3.73 (m, 1H), 3.65-3.40



yl)benzamide
(m, 3H), 2.38-2.22 (m, 1H), 2.15-1.94




(m, 1H)


371
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 421


ylmethyl)-4-{1-
7.89 (m, 3H), 7.52 (d, J = 1.2 Hz, 1H),
(M + H) +


[(propan-2-
7.41 (m, 3H), 6.85 (dd, J = 7.0, 1.6 Hz,



yloxy)acetyl]pyr-
1H), 4.51 (d, J = 5.9 Hz, 2H), 4.05 (d,



rolidin-3-
J = 4.5 Hz, 2H), 3.95-3.81 (m, 1H),



yl}benzamide
3.70-3.55 (m, 2H), 3.55-3.20 (m, 3H),




2.38-2.18 (m, 1H), 2.08-1.88 (m, 1H),




1.11 (m, 6H)


372
4-[1-(2-hydroxy-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


2-methyl-
9.07 (t, J = 6.0 Hz, 1H), 8.48 (d, J = 7.0
m/e 407


propanoyl)pyr-
Hz, 1H), 7.88 (m, 3H), 7.52 (d, J = 1.2
(M + H) +


rolidin-3-yl]-
Hz, 1H), 7.42 (m, 2H), 7.38 (m, 1H),



N-(imidazo[1,2-
6.85 (dd, J = 7.0, 1.6 Hz, 1H), 5.15



a]pyridin-7-
(m, 1H), 4.50 (d, J = 5.9 Hz, 2H), 4.34



ylmethyl)ben-
(m, 1H), 3.85-3.65 (m, 1H), 3.59 (m,



zamide
3H), 2.35-2.10 (m, 1H), 2.05-1.86 (m,




1H), 1.30 (m, 6H); )


373
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 419


ylmethyl)-4-{1-
7.88 (m, 3H), 7.52 (s, 1H), 7.45-7.35
(M + H) +


[(2R)-
(m, 3H), 6.85 (d, J = 7.1 Hz, 1H), 4.55



tetrahydrofuran-2-
(m, 1H), 4.50 (m, 2H), 4.10-3.93 (m,



ylcarbonyl]pyr-
1H), 3.90-3.65 (m, 3H), 3.65-3.20 (m,



rolidin-3-
3H) 2.37-2.19 (m, 1H), 2.10-1.76 (m,



yl}benzamide
5H)


374
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.08 (m, 1H), 8.48 (m, 1H), 7.88 (m,
m/e 419


ylmethyl)-4-{1-
3H), 7.52 (s, 1H), 7.45-7.37 (m, 3H),
(M + H) +


[(2S)-
6.85 (dd, J = 7.0, 1.6 Hz, 1H), 4.55 (m,



tetrahydrofuran-2-
1H), 4.50 (m, 2H), 4.10-3.93 (m, 1H),



ylcarbonyl]pyrroli-
3.90-3.65 (m, 3H), 3.65-3.20 (m, 3H)



din-3-
2.37-2.19 (m, 1H), 2.10-1.75 (m, 5H)



yl}benzamide



375
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.08 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 419


ylmethyl)-4-{1-
7.89 (m, 3H), 7.52 (s, 1H), 7.46 (m,
(M + H) +


[(3S)-
1H), 7.41 (m, 1H), 7.38 (m, 1H), 6.85



tetrahydrofuran-3-
(d, J = 7.1 Hz, 1H), 4.51 (m, 2H), 4.10-



ylcarbonyl]pyrroli-
3.93 (m, 1H), 3.95-3.80 (m, 2H), 3.65-



din-3-
3.20 (m, 6H), 2.36-2.20 (m, 1H), 2.14-



yl}benzamide
1.85 (m, 4H)


376
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 433


ylmethyl)-4-[1-
7.88 (m, 3H), 7.51 (s, 1H), 7.45 (d, J =
(M + H) +


(tetrahydro-2H-
8.0 Hz, 1H), 7.41 (m, 2H), 6.85 (m,



pyran-4-
1H), 4.51 (d, J = 3.0 Hz, 2H), 3.88 (m,



ylcarbonyl)pyrroli-
3H), 3.75 (m, .55 (m, 2H), 3.55-3.20



din-3-
(m, 3H), 2.71 (m, 1H), 2.39-2.19 (m,



yl]benzamide
1H), 2.10-1.85 (m, 1H), 1.59 (m, 4H)


377
4-[1-(1,4-dioxan-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


2-yl-
9.07 (m, 1H), 8.48 (d, J = 7.1 Hz, 1H),
m/e 435


carbonyl)pyrroli-
7.89 (m, 3H), 7.52 (s, 1H), 7.43 (m,
(M + H) +


din-3-yl]-N-
2H), 7.38 (s, 1H), 6.85 (d, J = 7.1 Hz,



(imidazo[1,2-
1H), 4.51 (dd, J = 5.8, 2.9 Hz, 2H),



a]pyridin-7-
4.27 (m, 2H), 4.15-4.00 (m, 1H), 3.90-



ylmethyl)ben-
3.70 (m, 4H), 3.70-3.20 (m, 5H); 2.39-



zamide
2.19 (m, 1H), 2.15-1.88 (m, 1H)


378
N-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
9.07 (m, 1H), 8.48 (d, J = 7.0 Hz, 1H),
m/e 447


ylmethyl)-4-[1-
7.88 (m, 3H), 7.52 (s, 1H), 7.42 (m,
(M + H) +


(tetrahydro-2H-
2H), 7.38 (s, 1H), 6.85 (d, J = 7.1 Hz,



pyran-4-ylacet-
1H), 4.51(m, 2H), 3.95 (m, 1H), 3.83



yl)pyrrolidin-
(m, 3H), 3.63 (m, 1H), 3.47 (m, 2H),



3-yl]benzamide
3.45-3.20 (m, 2H), 2.38-2.15 (m, 3H),




2.10-1.90 (m, 2H), 1.56 (m, 2H),




1.21 (m, 2H)


488
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 431


ylmethyl)-4-[1-

(M + H) +


(thiophen-2-




ylcarbonyl)pyr-




rolidin-3-




yl]benzamide



562
4-[1-(4-fluoro-

(ESI(+))


benzoyl)pyrroli-

m/e 443


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



580
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 403


ylmethyl)-4-{1-

(M + H) +


[(2-methylcyclo-




propyl)carbon-




yl]pyrrolidin-3-




yl}benzamide



581
4-[1-(cyclopentyl-

(ESI(+))


acetyl)pyrroli-

m/e 431


din-3-yl]-N-

(M + H) +


(imidazo[1,2-a]py-




ridin-7-ylmeth-




yl)benzamide



582
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 419


ylmethyl)-4-[1-(3-

(M + H) +


methylpentan-




oyl)pyrrolidin-3-




yl]benzamide



583
4-[1-(cyclopen-

(ESI(+))


tylcarbonyl)pyr-

m/e 417


rolidin-3-

(M + H) +


yl]-N-(imida-




zo[1,2-a]pyri-




din-7-ylmeth-




yl)benzamide



584
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 403


ylmethyl)-4-{1-

(M + H) +


[(1-methylcyc-




lopropyl)car-




bonyl]pyrroli-




din-3-yl}ben-




zamide



585
4-[1-(2,2-dimeth-

(ESI(+))


ylpropanoyl)pyr-

m/e 405


rolidin-3-yl]-N-

(M + H) +


(imidazo[1,2-a]py-




ridin-7-ylmeth-




yl)benzamide



586
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 432


ylmethyl)-4-[1-

(M + H) +


(1,3-thiazol-5-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



587
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 455


ylmethyl)-4-[1-(2-

(M + H) +


methoxyben-




zoyl)pyrrolidin-3-




yl]benzamide



588
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 432


ylmethyl)-4-[1-

(M + H) +


(1,3-thiazol-4-




ylcarbonyl)pyr-




rolidin-3-




yl]benzamide



589
4-[1-(2-fluoroben-

(ESI(+))


zoyl)pyrrolidin-

m/e 443


3-yl]-N-(imida-

(M + H) +


zo[1,2-a]pyri-




din-7-ylmeth-




yl)benzamide



590
4-[1-(furan-2-

(ESI(+))


ylcarbonyl)pyr-

m/e 415


rolidin-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)ben-




zamide



591
4-[1-(3-fluoro-

(ESI(+))


benzoyl)pyrroli-

m/e 443


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



592
4-[1-(2,4-difluor-

(ESI(+))


obenzoyl)pyrroli-

m/e 461


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



593
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 429


ylmethyl)-4-{1-

(M + H) +


[(1-methyl-1H-




pyrazol-3-




yl)carbonyl]pyr-




rolidin-3-




yl}benzamide



594
4-[1-(2-chloroben-

(ESI(+))


zoyl)pyrrolidin-

m/e 459


3-yl]-N-(imida-

(M + H) +


zo[1,2-a]pyri-




din-7-ylmeth-




yl)benzamide



595
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 439


ylmethyl)-4-[1-(2-

(M + H) +


methylben-




zoyl)pyrrolidin-




3-yl]benzamide



596
4-[1-(4-chloro-

(ESI(-0)


benzoyl)pyrroli-

m/e 459


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



597
4-[1-(3-chloro-

(ESI(+))


benzoyl)pyrroli-

m/e 459


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



598
4-[1-(2,2-dimeth-

(ESI(+))


ylbutanoyl)pyr-

m/e 419


rolidin-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-yl-




methyl)benzamide



599
4-[1-(3,5-difluoro-

(ESI(+))


benzoyl)pyrroli-

m/e 461


din-3-yl]-N-

(M + H) +


(imidazo[1,2-a]py-




ridin-7-ylmeth-




yl)benzamide



600
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-yl-

m/e 439


methyl)-4-[1-(4-

(M + H) +


methylben-




zoyl)pyrrolidin-3-




yl]benzamide



601
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 405


ylmethyl)-4-[1-(3-

(M + H) +


methylbutan-




oyl)pyrrolidin-3-




yl]benzamide



602
4-[1-(3,3-dimeth-

(ESI(+))


ylbutanoyl)pyr-

m/e 419


rolidin-3-yl]-

(M + H) +


N-(imidazo[1,2-




a]pyridin-7-yl-




methyl)ben-




zamide



603
4-[1-(3-cyanoben-

(ESI(+))


zoyl)pyrrolidin-

m/e 450


3-yl]-N-(imida-

(M + H) +


zo[1,2-a]pyridin-




7-ylmethyl)ben-




zamide



604
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 455


ylmethyl)-4-[1-(3-

(M + H) +


methoxyben-




zoyl)pyrrolidin-3-




yl]benzamide



605
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 455


ylmethyl)-4-[1-(4-

(M + H) +


methoxyben-




zoyl)pyrrolidin-3-




yl]benzamide



606
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 428


ylmethyl)-4-{1-

(M + H) +


[(1-methyl-1H-




pyrrol-2-




yl)carbonyl]pyr-




rolidin-3-




yl}benzamide



607
4-[1-(cyclohex-

(ESI(+))


ylacetyl)pyrroli-

m/e 445


din-3-yl]-N-

(M + H) +


(imidazo[1,2-a]py-




ridin-7-ylmeth-




yl)benzamide



608
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 426


ylmethyl)-4-[1-

(M + H) +


(pyridin-4-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



609
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 426


ylmethyl)-4-[1-

(M + H) +


(pyridin-3-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



610
4-[1-

(ESI(+))


(cyclohexylcarbon-

m/e 431


yl)pyrrolidin-3-

(M + H) +


yl]-N-(imida-




zo[1,2-a]pyridin-




7-ylmethyl)ben-




zamide



611
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 426


ylmethyl)-4-[1-

(M + H) +


(pyridin-2-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



612
4-[1-(furan-3-

(ESI(+))


ylcarbonyl)pyrroli-

m/e 415


din-3-yl]-N-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)ben-




zamide



613
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 432


ylmethyl)-4-[1-

(M + H) +


(1,3-thiazol-2-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



614
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 445


ylmethyl)-4-{1-

(M + H) +


[(1-methylcyclo-




hex-yl)carbon-




yl]pyrroli-din-3-




yl}benzamide



615
4-[1-(2,3-dimeth-

(ESI(+))


ylbutanoyl)pyrroli-

m/e 419


din-3-yl]-N-

(M + H) +


(imidazo[1,2-a]py-




ridin-7-ylmeth-




yl)benzamide



616
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 439


ylmethyl)-4-[1-(3-

(M + H) +


methylben-




zoyl)pyrrolidin-3-




yl]benzamide



617
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 431


ylmethyl)-4-[1-

(M + H) +


(thiophen-3-




ylcarbonyl)pyrroli-




din-3-




yl]benzamide



618
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 509


ylmethyl)-4-{1-[3-

(M + H) +


(trifluorometh-




oxy)benzoyl]pyr-




rolidin3-yl}ben-




zamide



619
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 445


ylmethyl)-4-{1-

(M + H) +


[(3-




methylthiophen-2-




yl)carbonyl]pyr-




rolidin-3-




yl}benzamide



620
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 493


ylmethyl)-4-{1-[3-

(M + H) +


(trifluorometh-




yl)benzoyl]pyr-




rolidin-3-yl}ben-




zamide



731
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 439


ylmethyl)-4-[1-

(M + H) +


(phenylacetyl)pyr-




rolidin-3-




yl]benzamide



732
N-(imidazo[1,2-

(ESI(+))


a]pyridin-7-

m/e 467


ylmethyl)-4-[1-(2-

(M + H) +


methyl-2-




phenylpropan-




oyl)pyrrolidin-3-




yl]benzamide



733
4-{1-

(ESI(+))


[difluoro(phenyl)a-

m/e 475


cetyl]pyrrolidin-3-

(M + H) +


yl}-N-(imida-




zo[1,2-a]pyridin-




7-ylmethyl)ben-




zamide






































































































































































































































































































































































































































Example 379
1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
Example 379A
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yl)phenyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 379B
1-[4-(1-acetylpyrrolidin-3-yl)phenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(pyrrolidin-3-yl)phenyl)urea for 3-methylbutan-1-amine and acetic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.62 (d, J=6.4 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m, 3H), 7.16 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.69 (m, 1H), 4.33 (d, J=6.0 Hz, 2H), 3.89-3.73 (m, 1H), 3.65-3.45 (m, 3H), 3.10 (m, 1H), 2.29-2.11 (m, 1H), 2.00-1.80 (m, 1H), 1.91 (s, 3H); (ESI(+)) m/e 378 (M+H) + .





TABLE 19



The following Examples were prepared

essentially as described in Example 379, substituting

the appropriate carboxylic acid in Example 379B.






Ex
Name
1 H NMR
MS



380
1-(imida-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]pyri-
8.62 (d, J = 6.5 Hz, 1H), 8.48 (d, J =
m/e 406


din-7-ylmeth-
7.0 Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H),
(M + H) +


yl)-3-{4-[1-(2-
7.36 (m, 3H), 7.16 (m, 2H), 6.83 (d, J =



methyl-pro-
7.1 Hz, 1H), 6.70 (m, 1H), 4.33 (d, J = 6.0



panoyl)pyr-
Hz, 2H), 3.80-3.65 (m, 1H), 3.60-3.48 (m,



rolidin-3-
1H), 3.45-3.20 (m, 2H), 3.13 (m, 1H),



yl]phen-
2.68 (m, 1H), 2.30-2.10 (m, 1H), 2.05-



yl}urea
1.80 (m, 1H), 1.00 (m, 6H)


381
1-(imida-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]pyri-
8.62 (d, J = 6.5 Hz, 1H), 8.48 (d, J = 7.0
m/e 420


din-7-ylmeth-
Hz, 1H), 7.88 (s, 1H), 7.52 (s, 1H), 7.37
(M + H) +


yl)-3-(4-{1-
(m, 3H), 7.17 (m, 2H), 6.83 (dd, J = 7.0,



[(2S)-2-meth-
1.6 Hz, 1H), 6.69 (t, J = 6.0 Hz, 1H), 4.33



ylbutan-
(d, J = 6.0 Hz, 2H), 3.95-3.75 (m, 1H),



oyl]pyrroli-
3.70-3.45 (m, 2H), 3.45-3.20 (m, 1H),



din-3-yl}phen-
3.20 (m, 1H), 2.30-2.11 (m, 1H), 2.05-



yl)urea
1.80 (m, 1H), 1.55 (m, 1H), 1.25 (m, 2H),




0.96 (m, 3H), 0.87 (m, 3H)


382
1-{4-[1-(cyclo-
− 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


propylacet-
8.62 (d, J = 4.1 Hz, 1H), 8.49 (d, J = 7.0 Hz,
m/e 418


yl)pyrrolidin-
1H), 7.89 (s, 1H), 7.52 (s, 1H), 7.37 (m,
(M + H) +


3-yl]phenyl}-
3H), 7.16 (m, 2H), 6.84 (d, J = 7.1 Hz, 1H),



3-(imida-
6.69 (t, J = 6.0 Hz, 1H), 4.33 (d, J = 6.0 Hz,



zo[1,2-a]pyri-
2H), 3.80 (m, 1H), 3.58 (m, 1H), 3.45 (m,



din-7-ylmeth-
1H), 3.40-3.20 (m, 1H), 3.12 (m, 1H),



yl)urea
2.27-2.11 (m, 3H), 1.99-1.81 (m, 1H),




0.98 (m, 1H), 0.44 (m, 2H), 0.11 (m, 2H)


383
1-[4-(1-ben-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zoylpyrroli-
8.62 (m, 1H), 8.48 (d, J = 6.1 Hz, 1H),
m/e 440


din-3-yl)phen-
7.88 (d, J = 3.0 Hz, 1H), 7.53 (m, 3H), 7.50-
(M + H) +


yl]-3-(imida-
7.35 (m, 5H), 7.34 (d, 1H), 7.20 (d, J = 8.2



zo[1,2-a]pyri-
Hz, 1H), 7.13 (d, J = 8.2 Hz, 1H), 6.83 (m,



din-7-ylmeth-
1H), 6.68 (m, 1H), 4.33 (d, J = 14.1 Hz, 2H),



yl)urea
3.68 (m, 1H), 3.60-3.45 (m, 2H), 3.40-3.20




(m, 2H), 2.29-2.13 (m, 1H) 2.07-1.90 (m,




1H)


384
1-(imida-
− 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]pyri-
8.63 (d, J = 6.0 Hz, 1H), 8.48 (d, J = 7.0 Hz,
m/e 436


din-7-ylmeth-
1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m,
(M + H) +


yl)-3-(4-{1-
3H), 7.16 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz,



[(propan-2-
1H), 6.70 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H),



yloxy)acet-
4.03 (d, J = 5.4 Hz, 2H), 3.90-3.74 (m,



yl]pyrrolidin-3-
1H), 3.68-3.52 (m, 2H), 3.47 (m, 1H),



yl}phenyl)urea
3.40-3.20 (m, 1H), 3.16 (m, 1H), 2.29-




2.11 (m, 1H), 2.00-1.73 (m, 1H), 1.10 (m,




6H)


385
1-{4-[1-(2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


hydroxy-2-
8.65 (d, J = 6.0 Hz, 1H), 8.48 (d, J = 7.0
m/e 422


methylpropan-
Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37
(M + H) +


oyl)pyrrolidin-
(m, 3H), 7.16 (m, 2H), 6.83 (dd, J = 7.0,



3-yl]phenyl}-3-
1.6 Hz, 1H), 6.73 (m, 1H), 5.18 (bs, 1H),



(imidazo[1,2-
4.33 (d, J = 6.0 Hz, 2H), 4.28 (m, 1H), 3.80-



a]pyridin-7-
3.60 (m, 1H), 3.60-3.10 (m, 3H), 2.25-2.08



ylmethyl)urea
(m, 1H), 1.97-1.73 (m, 1H), 1.30 (m, 6H)


386
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.62 (d, J = 5.7 Hz, 1H), 8.48 (d, J = 7.0 Hz,
m/e 434


ylmethyl)-3-(4-
1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m,
(M + H) +


{1-[(2R)-
3H), 7.16 (m, 2H), 6.83 (d, J = 6.2 Hz, 1H),



tetrahydro-
6.69 (t, J = 6.0 Hz, 1H), 4.53 (m, 1H), 4.33



furan-2-ylcar-
(d, J = 6.0 Hz, 2H), 3.85-3.64 (m, 3H),



bonyl]pyr-
3.63-3.45 (m, 1H), 3.45-3.20 (m, 2H),



rolidin-3-
3.16 (m, 1H), 2.29-2.10 (m, 1H), 2.08-



yl}phenyl)urea
1.92 (m, 2H), 1.91-1.73 (m, 3H)


387
1-(imidazo[1,2-
− 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.62 (d, J = 5.6 Hz, 1H), 8.48 (d, J = 7.0
m/e 434


ylmethyl)-3-(4-
Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.36
(M + H) +


{1-[(2S)-
(m, 3H), 7.16 (m, 2H), 6.83 (dd, J = 7.0,



tetrahydro-
1.6 Hz, 1H), 6.69 (t, J = 6.0 Hz, 1H), 4.53



furan-2-ylcar-
(m, 1H), 4.33 (d, J = 6.0 Hz, 2H), 3.84-



bonyl]pyr-
3.64 (m, 3H), 3.63-3.45 (m, 1H), 3.45-



rolidin-3-
3.20 (m, 2H), 3.16 (m, 1H), 2.29-2.10



yl}phenyl)urea
(m, 1H), 2.05-1.85 (m, 5H)


388
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.63 (d, J = 6.7 Hz, 1H), 8.48 (d, J = 7.0
m/e 434


ylmethyl)-3-(4-
Hz, 1H), 7.88 (s, 1H), 7.52 (s, 1H), 7.37
(M + H) +


{1-[(3S)-
(m, 3H), 7.17 (m, 2H), 6.83 (dd, J = 7.0,



tetrahydro-
1.6 Hz, 1H), 6.70 (m, 1H), 4.33 (d, J = 6.0



furan-3-
Hz, 2H), 3.97-3.84 (m, 2H), 3.80-3.63 (m,



ylcarbonyl]pyr-
4H), 3.62-3.46 (m, 1H), 3.45-3.10 (m, 3H),



rolidin-3-
2.29-2.10 (m, 1H), 2.09-1.83 (m, 3H)



yl}phenyl)urea



389
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.62 (d, J = 7.5 Hz, 1H), 8.48 (d, J = 7.0 Hz,
m/e 448


ylmethyl)-3-{4-
1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.36 (m,
(M + H) +


[1-(tetrahydro-
3H), 7.16 (m, 2H), 6.83 (d, J = 7.1 Hz, 1H),



2H-pyran-4-
6.69 (t, J = 6.0 Hz, 1H), 4.33 (d, J = 6.0 Hz,



ylcarbonyl)pyr-
2H), 3.90-3.70 (m, 3H), 3.55 (m, 1H),



rolidin-3-
3.45-3.20 (m, 3H), 3.15 (m, 1H), 2.70 (m,



yl]phenyl}urea
1H), 2.28-2.11 (m, 1H), 2.00-1.82 (m,




1H), 1.57 (m, 4H)


390
1-{4-[1-(1,4-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


dioxan-2-
8.62 (d, J = 7.5 Hz, 1H), 8.48 (d, J = 7.0 Hz,
m/e 450


ylcarbonyl)pyr-
1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (m,
(M + H) +


rolidin-3-
3H), 7.16 (m, 2H), 6.83 (d, J = 7.1 Hz, 1H),



yl]phenyl}-3-
6.70 (t, J = 6.0 Hz, 1H), 4.33 (d, J = 6.0 Hz,



(imidazo[1,2-
2H), 4.25 (m, 1H), 3.85-3.70 (m, 3H),



a]pyridin-7-
3.70-3.60 (m, 2H), 3.60-3.45 (m, 3H),



ylmethyl)urea
3.45-3.15 (m, 3H), 2.28-2.11 (m, 1H),




2.00-1.80 (m, 1H)


391
1-(imidazo[1,2-
− 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-yl-
8.62 (d, J = 5.5 Hz, 1H), 8.48 (d, J = 7.0 Hz,
m/e 462


methyl)-3-{4-
1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.36 (m,
(M + H) +


[1-(tetrahydro-
3H), 7.16 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz,



2H-pyran-4-
1H), 6.69 (t, J = 6.0 Hz, 1H), 4.33 (d, J =



ylacetyl)pyr-
5.9 Hz, 2H), 3.90-3.72 (m, 3H), 3.67-



rolidin-3-
3.40 (m, 2H), 3.27-3.08 (m, 2H), 3.14 (m,



yl]phenyl}urea
1H), 2.28-2.10 (m, 3H), 2.00-1.80 (m,




3H), 1.59 (m, 2H), 1.17 (m, 2H)


392
1-(imidazo[1,2-
− 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-yl-
8.65 (d, J = 6.1 Hz, 1H), 8.48 (d, J = 6.9 Hz,
m/e 463


methyl)-3-{4-
1H), 7.88 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H),
(M + H) +


[1-(morpholin-
736 (m, 3H), 7.16 (m, 2H), 6.83 (dd, J =



4-ylacetyl)pyr-
6.9, 1.7 Hz, 1H), 6.72 (td, J = 6.0, 2.3 Hz,



rolidin-3-
1H), 4.33 (d, J = 5.9 Hz, 2H), 3.74 (m, 1H),



yl]phenyl}urea
3.55 (m, 4H), 3.45-3.20 (m, 2H), 3.17 (s,




2H), 3.13-3.03 (m, 2H), 2.44 (m, 4H),




2.30-2.10 (m, 1H), 2.00-1.80 (m, 1H)












































































































































Example 393
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide
Example 393A
methyl 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
Example 393B
4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 393C
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-N′-(3-methylbutyl)benzene-1,4-dicarboxamide
The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.25-9.11 (m, 1H), 8.57-8.37 (m, 2H), 8.04-7.81 (m, 5H), 7.51 (t, J=2.6 Hz, 1H), 7.41 (t, J=2.9 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.58-4.38 (m, 2H), 3.29-3.25 (m, 2H), 1.71-1.56 (m, 1H), 1.53-1.31 (m, 2H), 0.91 (d, J=6.5 Hz, 6H); MS (ESI(+)) m/e 365 (M+H) + .
Example 394
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-N′-[(3S)-tetrahydrofuran-3-ylmethyl]benzene-1,4-dicarboxamide
The title compound was prepared as described in Example 1A, substituting (S)-(tetrahydrofuran-3-yl)methanamine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.69 (t, J=5.7 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.07-7.71 (m, 5H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.80-3.56 (m, 4H), 3.48 (dd, J=8.5, 5.2 Hz, 1H), 2.02-1.87 (m, 1H), 1.68-1.53 (m, 1H), 1.32-1.00 (m, 2H); MS (ESI(+)) m/e 379 (M+H) + .
Example 396
4-{[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]amino}-N-(tetrahydro-2H-pyran-2-ylmethyl)benzamide
A solution of 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide (0.016 g, 0.041 mmol) in chloroform (0.813 ml) was treated with N-chlorosuccinimide (5.70 mg, 0.043 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under a stream of nitrogen and purified using normal phase chromatography to give the title compound. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.11 (s, 1H), 9.02 (s, 1H), 8.89-8.85 (m, 1H), 8.35 (t, J=5.8 Hz, 1H), 7.85-7.79 (m, 2H), 7.69-7.60 (m, 2H), 7.58-7.52 (m, 2H), 7.19 (dd, J=9.5, 2.0 Hz, 1H), 3.91-3.83 (m, 1H), 3.46-3.19 (m, 4H), 1.80-1.73 (m, 1H), 1.66-1.57 (m, 1H), 1.49-1.36 (m, 3H), 1.26-1.09 (m, 1H); MS (ESI(+)) m/e 428 (M+H) + .
Example 398
N-[(3-chloroimidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide
The title compound was prepared as described in Example 396, substituting N-[(3-imidazo[1,2-a]pyridin-6-yl)methyl]-4-[(tetrahydrofuran-3-ylacetyl)amino]benzamide for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 10.15 (s, 1H), 8.95 (t, J=5.8 Hz, 1H), 8.30-8.25 (m, 1H), 7.87-7.80 (m, 2H), 7.71-7.59 (m, 4H), 7.35 (dd, J=9.3, 1.7 Hz, 1H), 4.54 (d, J=5.8 Hz, 2H), 3.86-3.58 (m, 3H), 3.38-3.30 (m, 1H), 2.62-2.52 (m, 1H), 2.47-2.39 (m, 2H), 2.10-1.95 (m, 1H), 1.62-1.46 (m, 1H); MS (ESI(+)) m/e 413 (M+H) + .
Example 399
5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 399A
5-(4-hydroxytetrahydro-2H-pyran-4-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 324A, substituting dihydro-2H-pyran-4(3H)-one for N-(oxetan-3-ylidene)propane-2-sulfinamide.
Example 399B
5-(4-hydroxytetrahydro-2H-pyran-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(4-hydroxytetrahydro-2H-pyran-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.66 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.37 (s, 1H), 7.02 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 5.67 (s, 1H), 4.46 (d, J=6.1 Hz, 2H), 3.63-3.77 (m, 4H), 1.89-2.04 (m, 2H), 1.69 (d, J=11.9 Hz, 2H); MS (ESI(+)) m/e 358 (M+H) + .
Example 400
5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 400A
5-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 324A, substituting tert-butyl 3-oxoazetidine-1-carboxylate for N-(oxetan-3-ylidene)propane-2-sulfinamide.
Example 400B
tert-butyl 3-hydroxy-3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)azetidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 400C
5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-hydroxy-3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 400D
5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.06 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J=3.6 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.18 (d, J=3.6 Hz, 1H), 6.90 (s, 1H), 6.83 (dd, J=6.9, 1.4 Hz, 1H), 4.47 (d, J=6.0 Hz, 2H), 4.41 (d, J=9.1 Hz, 1H), 4.32 (d, J=9.1 Hz, 1H), 4.05 (dd, J=17.5, 9.9 Hz, 2H), 2.46-2.57 (m, 1H), 1.00 (d, J=7.1 Hz, 6H); MS (ESI(+) m/e 399 (M+H) + .
Example 401
5-(1-benzoyl-3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.05 (t, J=5.8 Hz, 1H), 8.48 (d, J=6.1 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J=3.7 Hz, 1H), 7.66-7.71 (m, 2H), 7.43-7.54 (m, 4H), 7.38 (d, J=1.0 Hz, 1H), 7.26 (d, J=3.7 Hz, 1H), 6.93 (s, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.46 (d, J=6.1 Hz, 2H), 4.23-4.63 (br. m, 4H); MS (ESI(+)) m/e 433 (M+H) + .
Example 402
tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.09 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (m, 2H), 3.87 (m, 3H), 1.41 (s, 9H); (ESI(+)) m/e 407 (M+H) + .
Example 403
tert-butyl 4-hydroxy-4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate
Example 403A
5-(1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 324A, substituting tert-butyl 3-oxopiperidine-1-carboxylate for N-(oxetan-3-ylidene)propane-2-sulfinamide.
Example 403B
tert-butyl 4-hydroxy-4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.98 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.01 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 5.72 (s, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.75-3.86 (m, 2H), 1.71-1.86 (m, 2H), 1.41 (s, 9H), 1.21-1.30 (m, 2H), 0.94 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 457 (M+H) + .
Example 404
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea
Example 404A
ethyl 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylate
The title compound was prepared as described in Example 1C, substituting ethyl 2-aminothiazole-5-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 404B
2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid
The title compound was prepared as described in Example 4B, substituting ethyl 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 404C
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[5-(piperidin-1-ylcarbonyl)-1,3-thiazol-2-yl]urea
The title compound was prepared as described in Example 1A, substituting piperidine for 3-methylbutan-1-amine and 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 10.91 (s, 1H), 8.49 (d, J=7.1 Hz, 1H), 7.89 (s, 1H), 7.62 (s, 1H), 7.52 (d, J=0.8 Hz, 1H), 7.39 (s, 1H), 7.11-7.18 (m, 1H), 6.83 (dd, J=6.9, 1.4 Hz, 1H), 4.39 (d, J=6.0 Hz, 2H), 3.54-3.61 (m, 4H), 1.47-1.67 (m, 6H); MS (ESI(+)) m/e 385 (M+H) + .
Example 405
5-{3-hydroxy-1-[(2S)-2-methylbutanoyl]azetidin-3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.06 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.72 (d, J=4.1 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.16 (dd, J=7.0, 3.9 Hz, 1H), 6.89 (s, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 4.46 (d, J=6.1 Hz, 2H), 4.35-4.42 (m, 1H), 4.32 (d, J=8.8 Hz, 1H), 4.09 (dd, J=10.5, 4.4 Hz, 1H), 4.03 (d, J=10.2 Hz, 1H), 2.25-2.38 (m, 1H), 1.49 (s, 1H), 1.23-1.38 (m, 1H), 0.99 (d, J=6.8 Hz, 3H), 0.80-0.88 (m, 3H); MS (ESI(+)) m/e 413 (M+H) + .
Example 406
5-[3-hydroxy-1-(tetrahydro-2H-pyran-4-ylacetyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-hydroxyazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.07 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.18 (d, J=4.0 Hz, 1H), 6.89 (s, 1H), 6.83 (dd, J=7.0, 1.5 Hz, 1H), 4.47 (d, J=5.8 Hz, 2H), 4.37 (d, J=9.2 Hz, 1H), 4.26-4.40 (m, 2H), 4.05-4.11 (m, 1H), 4.00-4.10 (m, 2H), 3.78-3.84 (m, 2H), 2.04-2.07 (m, 2H), 1.85-1.97 (m, 1H), 1.53-1.62 (m, 2H), 1.15-1.28 (m, 2H); MS (ESI(+)) m/e 455 (M+H) + .
Example 407
2-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}-N-(3-methylbutyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting 3-methylbutan-1-amine for 3-methylbutan-1-amine and 2-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)thiazole-5-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.49 (d, J=7.8 Hz, 1H), 8.21 (t, J=5.9 Hz, 1H), 7.88-7.89 (m, J=1.4 Hz, 1H), 7.87 (s, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.39 (s, 1H), 7.18 (t, J=5.8 Hz, 1H), 6.83 (dd, J=6.8, 1.7 Hz, 1H), 4.38 (d, J=6.1 Hz, 2H), 3.16-3.25 (m, 2H), 1.52-1.67 (m, 1H), 1.38 (q, J=6.9 Hz, 2H), 0.83-0.91 (m, 7H); MS (ESI(+)) m/e 387 (M+H) + .
Example 408
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(3-{[(25)-2-methylbutanoyl]amino}oxetan-3-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(3-aminooxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.11 (s, 1H), 9.05 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.71 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.22 (d, J=3.7 Hz, 1H), 6.83 (dd, J=7.1, 1.7 Hz, 1H), 4.77-4.83 (m, 2H), 4.72 (dd, J=6.4, 4.4 Hz, 2H), 4.46 (d, J=5.8 Hz, 2H), 2.19-2.29 (m, 1H), 1.46-1.66 (m, 1H), 1.26-1.43 (m, 1H), 1.03 (d, J=6.8 Hz, 3H), 0.85 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 413 (M+H) + .
Example 409
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide
Example 409A
1-(4-hydroxypiperidin-1-yl)-3-methylbutan-1-one
The title compound was prepared as described in Example 52A, substituting 3-methylbutanoyl chloride for 2-cyclopentylacetyl chloride and piperidin-4-ol for methyl 4-aminobenzoate.
Example 409B
ethyl 1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylate
A solution of 1-(hydroxypiperidin-1-yl)-3-methylbutan-1-one (793 mg, 4.28 mmol), ethyl 1H-pyrazole-4-carboxylate (500 mg, 3.57 mmol) and cyanomethylenetributylphosphorane (1.03 g, 4.28 mmol) in toluene (20 ml) was stirred overnight at 85° C. The solvent was removed and the crude mixture was purified by normal phase chromatography to give the title compound.
Example 409C
1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylic acid
The title compound was prepared as described in Example 4B, substituting ethyl 1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 409D
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]-1H-pyrazole-3-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 1-(1-(3-methylbutanoyl)piperidin-4-yl)-1H-pyrazole-3-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.50 (dd, J=7.0, 0.9 Hz, 1H), 7.93-7.86 (m, 1H), 7.57-7.47 (m, 2H), 7.41 (s, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 5.45-5.28 (m, 1H), 4.57-4.43 (m, 3H), 3.99 (d, J=14.0 Hz, 1H), 3.20-3.03 (m, 1H), 2.70-2.53 (m, 1H), 2.32-2.11 (m, 3H), 2.09-1.68 (m, 4H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 408 (M+H).
Example 424
1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
Example 424A
tert-butyl 3-(4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenoxy)azetidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 3-(4-aminophenoxy)azetidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine
Example 424B
1-(4-(azetidin-3-yloxy)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenoxy)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 424C
1-{4-[(1-acetylazetidin-3-yl)oxy]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(4-(azetidin-3-yloxy)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.50 (m, 2H), 7.88 (s, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 7.33 (m, 2H), 6.83 (dd, J=6.9, 1.6 Hz, 1H), 6.74 (m, 2H), 6.63 (t, J=6.0 Hz, 1H), 4.93 (m, 1H), 4.51 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 4.24 (m, 1H), 4.04 (dd, J=9.6, 4.1 Hz, 1H), 3.72 (dd, J=10.5, 4.0 Hz, 1H), 1.78 (s, 3H); (ESI(+)) m/e 380 (M+H) + .





TABLE 20



The following Examples were prepared

essentially as described in Example 424, substituting

the appropriate carboxylic acid in Example 424C.






Ex
Name
1 H NMR
MS



425
1-(imida-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]pyri-
8.49 (m, 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2
m/e 408


din-7-ylmeth-
Hz, 1H), 7.37 (m, 1H), 7.33 (m, 2H), 6.83
(M + H) +


yl)-3-(4-{[1-
(dd, J = 6.9, 1.7 Hz, 1H), 6.75 (m, 2H),



(2-methylpro-
6.63 (t, J = 6.0 Hz, 1H), 4.95 (m, 1H), 4.57



panoyl)azeti-
(dd, J = 9.4, 6.4 Hz, 1H), 4.32 (d, J = 6.0



din-3-
Hz, 2H), 4.25 (dd, J = 10.5, 6.5 Hz, 1H),



yl]oxy}phen-
4.08 (dd, J = 9.4, 3.9 Hz, 1H), 3.73 (dd, J =



yl)urea
10.5, 4.0 Hz, 1H), 2.47 (m, 1H), 0.97




(m, 6H)


426
1-(imida-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]pyri-
8.49 (m, 2H), 7.88 (d, J = 1.1 Hz, 1H),
m/e 422


din-7-yl-
7.51 (d, J = 1.2 Hz, 1H), 7.37 (m, 1H),
(M + H) +


methyl)-3-[4-
7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz,



({1-[(25)-2-
1H), 6.75 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H),



methylbutan-
4.95 (m, 1H), 4.56 (dd, J = 9.4, 6.5 Hz,



oyl]azetidin-
1H), 4.32 (d, J = 6.0 Hz, 2H), 4.26 (m,



3-yl}ox-
1H), 4.08 (m, 1H), 3.74 (m, 1H), 2.28 (m,



y)phenyl]urea
1H), 1.47 (m, 1H), 1.28 (m, 1H), 0.95 (m,




3H), 0.81 (m, 3H)


427
1-(4-{[1-(cyc-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


lopropylacet-
8.49 (m, 2H), 7.90 (s, 1H), 7.54 (d, J = 1.2
m/e 420


yl)azetidin-
Hz, 1H), 7.39 (s, 1H), 7.33 (m, 2H), 6.86
(M + H) +


3-yl]ox-
(dd, J = 7.0, 1.6 Hz, 1H), 6.74 (m, 2H),



y}phenyl)-
6.64 (t, J = 6.0 Hz, 1H), 4.94 (m, 1H), 4.50



3-(imida-
(dd, J = 9.6, 6.6 Hz, 1H), 4.33 (d, J = 6.0



zo[1,2-a]py-
Hz, 2H), 4.26 (dd, J =10.5, 6.5 Hz, 1H),



ridin-7-yl-
4.03 (dd, J = 9.4, 3.9 Hz, 1H), 3.74 (dd,



methyl)urea
J = 10.5, 3.9 Hz, 1H), 2.02 (d, J = 6.8 Hz,




2H), 0.92 (m, 1H), 0.43 (m, 2H), 0.10




(m, 2H)


428
1-{4-[(1-ben-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zoylazetidin-
8.49 (m, 2H), 7.88 (s, 1H), 7.65 (m, 2H),
m/e 442


3-yl)ox-
7.52 (m, 2H), 7.45 (m, 2H), 7.37 (m, 1H),
(M + H) +


y]phenyl}-
7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.6 Hz,



3-(imida-
1H), 6.75 (m, 2H), 6.63 (t, J = 6.0 Hz, 1H),



zo[1,2-a]py-
5.00 (m, 1H), 4.67 (m, 1H), 4.51 (m, 1H),



ridin-7-yl-
4.32 (d, J = 6.0 Hz, 2H), 4.26 (m, 1H),



methyl)urea
3.97 (m, 1H)


429
1-(imida-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]py-
8.49 (m, 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2
m/e 438


ridin-7-yl-
Hz, 1H), 7.37 (s, 1H), 7.33 (m, 2H), 6.83
(M + H) +


methyl)-3-
(dd, J = 6.9, 1.6 Hz, 1H), 6.74 (m, 2H),



[4-({1-[(pro-
6.64 (t, J = 6.0 Hz, 1H), 4.96 (m, 1H), 4.60



pan-2-ylox-
(dd, J = 10.1, 6.4 Hz, 1H), 4.30 (m, 3H),



y)acetyl]a-
4.11 (dd, J = 10.1, 3.9 Hz, 1H), 3.94 (s,



zetidin-3-
2H), 3.77 (dd, J = 10.7, 3.8 Hz, 1H), 3.58



yl}oxy)phen-
(m, 1H), 1.09 (d, J = 6.1 Hz, 6H)



yl]urea



430
1-(4-{[1-(2-
1 H NMR (400 MHz, DMSO-d 6 ) 8 ppm
(ESI(+))


hydroxy-2-
8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H),
m/e 424


methylpro-
7.38 (s, 1H), 7.33 (m, 2H), 6.83 (dd, J =
(M + H) +


panoyl)azeti-
6.9, 1.6 Hz, 1H), 6.74 (m, 2H), 6.63 (t, J =



din-3-yl]ox-
6.0 Hz, 1H), 5.13 (s, 1H), 4.91 (m, 1H),



y}phenyl)-3-
4.78 (m, 1H), 4.32 (d, J = 6.0 Hz, 3H),



(imidazo[1,2-
4.26 (m, 1H), 3.73 (m, 1H), 1.25 (s, 6H)



a]pyridin-7-




ylmethyl)urea



431
1-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


(imidazo[1,2-
8.49 (m, 2H), 7.88 (s, 1H), 7.51 (d, J =
m/e 436


a]pyridin-7-
1.2 Hz, 1H), 7.37 (s, 1H), 7.33 (m, 2H),
(M + H) +


ylmethyl)-3-
6.83 (dd, J = 6.9, 1.6 Hz, 1H), 6.74 (m,



[4-({1-[(2R)-
2H), 6.63 (t, J = 6.0 Hz, 1H), 4.95 (m, 1H),



tetrahydrofur-
4.66 (m, 1H), 4.31 (m, 4H), 4.13 (m, 1H),



an-2-ylcar-
3.75 (m, 3H), 2.03 (m, 1H), 1.93 (m, 1H),



bonyl]azeti-
1.81 (m, 2H)



din-3-yl}ox-




y)phen-




yl]urea



432
1-(imida-
− 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-
8.49 (m, 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2
m/e 436


a]pyridin-7-
Hz, 1H), 7.37 (s, 1H), 7.33 (m, 2H), 6.83
(M + H) +


ylmethyl)-3-
(dd, J = 6.9, 1.6 Hz, 1H), 6.74 (m, 2H),



[4-({1-[(2S)-
6.64 (t, J = 6.0 Hz, 1H), 4.95 (m, 1H), 4.66



tetrahydro-
(m, 1H), 4.3123 (m, 4H), 4.13 (m, 1H),



furan-2-ylcar-
3.75 (m, 3H), 2.03 (m, 1H), 1.93 (m, 1H),



bonyl]azeti-
1.81 (m, 2H)



din-3-yl}ox-




y)phen-




yl]urea



433
1-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


(imidazo[1,2-
8.48 (m, 2H), 7.88 (d, J = 1.1 Hz, 1H),
m/e 450


a]pyridin-7-
7.51 (d, J = 1.2 Hz, 1H), 7.37 (s, 1H),
(M + H) +


ylmethyl)-3-
7.33 (m, 2H), 6.83 (dd, J = 6.9, 1.7 Hz,



(4-{[1-
1H), 6.74 (m, 2H), 6.64 (t, J = 6.0 Hz, 1H),



(tetrahydro-
4.95 (m, 1H), 4.60 (dd, J = 9.4, 6.5 Hz,



2H-pyran-4-
1H), 4.32 (d, J = 6.0 Hz, 3H), 4.26 (m, 1H),



ylcarbon-
4.11 (dd, J = 9.5, 3.8 Hz, 1H), 3.84 (m, 2H),



yl)azetidin-3-
3.74 (dd, J = 10.6, 3.9 Hz, 1H), 3.36-



yl]oxy}phen-
3.26 (m, 2H), 1.57 (m, 4H)



yl)urea



434
1-(4-{[1-(1,4-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


dioxan-2-
8.48 (d, 2H), 7.88 (s, 1H), 7.51 (s, 1H),
m/e 452


ylcarbon-
7.37 (s, 1H), 7.33 (m, 2H), 6.83 (dd, J =
(M + H) +


yl)azetidin-3-
6.9, 1.6 Hz, 1H), 6.74 (m, 2H), 6.64 (t,



yl]oxy}phen-
J = 6.0 Hz, 1H), 4.96 (m, 1H), 4.69 (m,



yl)-3-(imida-
1H), 4.30 (m, 3H),4.18 (m, 2H), 3.76 (m,



zo[1,2-a]py-
3H), 3.65-3.45 (m, 4H)



ridin-7-yl-




methyl)urea



435
1-(imida-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


zo[1,2-a]py-
8.51 (s, 1H), 8.48 (dd, J = 6.9, 0.9 Hz,
m/e 464


ridin-7-yl-
1H), 7.88 (d, J = 1.1 Hz, 1H), 7.51 (d,
(M + H) +


methyl)-3-
J = 1.2 Hz, 1H), 7.37 (s, 1H), 7.33 (m,



(4-{[1-(tet-
2H), 6.83 (dd, J = 6.9, 1.7 Hz, 1H), 6.74



rahydro-2H-
(m, 2H), 6.64 (t, J = 6.0 Hz, 1H), 4.94 (m,



pyran-4-yla-
1H), 4.52 (m, 1H), 4.32 (d, J = 6.0 Hz, 2H),



cetyl)azeti-
4.25 (m, 1H), 4.04 (dd, J = 9.5, 3.9 Hz, 1H),



din-3-yl]ox-
3.76 (m, 3H), 3.27 (m, 2H), 2.02 (d, J = 1.9



y}phen-
Hz, 2H), 1.87 (m, 1H), 1.54 (m, 2H), 1.19



yl)urea
(m, 2H)





































































































































Example 436
tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 321A-C, substituting (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate for (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate in Example 321A. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.41-8.35 (m, 1H), 7.91-7.83 (m, 2H), 7.81-7.76 (m, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.47-7.43 (m, 1H), 7.06-6.98 (m, 2H), 6.93 (dd, J=7.1, 1.5 Hz, 1H), 5.12-5.05 (m, 1H), 4.62 (bs, 2H), 3.68-3.39 (m, 4H), 2.25-2.13 (m, 2H), 1.49-1.43 (m, 9H).; MS (ESI(+)) m/e 437 (M+H) + .
Example 438
1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
Example 438A
1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 438B
1-[4-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.77-8.70 (m, 1H), 8.19-8.15 (m, 1H), 8.00-7.96 (m, 1H), 7.95-7.88 (m, 1H), 7.80 (s, 1H), 7.53-7.41 (m, 6H), 7.30-7.15 (m, 2H), 6.26-5.95 (m, 1H), 4.61 (bs, 2H), 4.41-4.31 (m, 1H), 4.17-4.08 (m, 1H), 4.02-3.93 (m, 1H), 3.69-3.59 (m, 1H), 2.67-2.52 (m, 2H); MS (ESI(+)) m/e 470 (M+H) + .
Example 439
1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-ylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and 2-(tetrahydro-2H-pyran-4-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.74 (dd, J=7.0, 0.9 Hz, 1H), 8.18-8.15 (m, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.92 (t, J=8.5 Hz, 1H), 7.82-7.78 (m, 1H), 7.47 (dd, J=7.0, 1.6 Hz, 1H), 7.28-7.15 (m, 2H), 6.16-6.10 (m, 1H), 4.61 (bs, 2H), 4.25-4.16 (m, 2H), 3.96-3.87 (m, 2H), 3.83-3.72 (m, 2H), 3.48-3.37 (m, 2H), 2.61-2.54 (m, 1H), 2.53-2.46 (m, 1H), 2.45-2.34 (m, 2H), 2.11-1.97 (m, 1H), 1.73-1.62 (m, 2H), 1.42-1.27 (m, 2H); MS (ESI(+)) m/e 492 (M+H) + .
Example 442
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea
Example 442A
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenoxy)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 442B
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-{[1-(2-methylpropanoyl)piperidin-4-yl]oxy}phenyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H), 7.37 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.62 (t, J=6.0 Hz, 1H), 4.48 (m, 1H), 4.32 (d, J=6.0 Hz, 2H), 3.85 (m, 1H), 3.74 (m 1H), 3.35 (m, 1H), 3.22 (m, 1H), 2.88 (m, 1H), 1.88 (m, 2H), 1.49 (m, 2H), 0.99 (d, J=6.7 Hz, 6H); (ESI(+)) m/e 436 (M+H) + .





TABLE 21



The following Examples were prepared essentially as described in Example

442, substituting the appropriate carboxylic acid in Example 442B.






Ex
Name
1 H NMR
MS



443
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H),
m/e 450


ylmethyl)-3-[4-
7.37 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H),
(M + H) +


({1-[(2S)-2-
6.83 (dd, J = 7.0, 1.6Hz, 1H), 6.65 (t, J =



methylbutanoyl]piperidin-
6.0 Hz, 1H), 4.49 (m, 1H), 4.32 (d, J = 6.0



4-yl}oxy)phenyl]urea
Hz, 2H), 3.84 (m, 2H), 3.26 (m, 2H), 2.72




(m, 1H), 1.90 (m, 2H), 1.51 (m, 3H), 1.29




(m, 1H), 0.97 (d, J = 6.7Hz, 3H), 0.81 (t,




J = 7.4Hz, 3H)


444
1-(4-{[1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


(cyclopropylacetyl)piperidin-
8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H),
m/e 448


4-yl]oxy}phenyl)-3-
7.37 (s, 1H), 7.31 (m, 2H), 6.87 (m, 2H),
(M + H) +


(imidazo[1,2-
6.83 (dd, J = 7.0, 1.6Hz, 1H), 6.62 (t, J =



a]pyridin-7-
6.0 Hz, 1H), 4.47 (m, 1H), 4.32 (d, J = 6.0



ylmethyl)urea
Hz, 2H), 3.85 (m, 1H), 3.66 (m, 1H), 3.30




(m, 1H), 3.22 (m, 1H), 2.26 (d, J = 6.8Hz,




2H), 1.91 (m, 2H), 1.50 (m, 2H), 0.95 (m,




1H), 0.44 (m, 2H), 0.11 (m, 2H)


445
1-{4-[(1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


benzoylpiperidin-
8.48 (m, 2H), 7.88 (s, 1H), 7.51 (s, 1H),
m/e 470


4-yl)oxy]phenyl}-
7.44 (m, 3H), 7.40 (m, 2H), 7.37 (m, 1H),
(M + H) +


3-(imidazo[1,2-
7.31 (m, 2H), 6.87 (m, 2H), 6.83 (dd, J =



a]pyridin-7-
7.0, 1.6Hz, 1H), 6.63 (t, J = 6.0 Hz, 1H),



ylmethyl)urea
4.52 (m, 1H), 4.31 (d, J = 6.0 Hz, 2H),




3.96 (m, 1H), 3.52 (m, 1H), 3.45-3.20




(m, 2H), 1.91 (m, 2H), 1.59 (m, 2H)


446
1-(imidazo[1,2-
1 H NMR (400 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.48 (m, 2H), 7.88 (m, 1H), 7.51 (d, J =
m/e 466


ylmethyl)-3-[4-
1.2Hz, 1H), 7.37 (m, 1H), 7.31 (m, 2H),
(M + H) +


({1-[(propan-2-
6.87 (m, 2H), 6.83 (dd, J = 7.0, 1.6Hz,



yloxy)acetyl]piperidin-
1H), 6.64 (m, 1H), 4.49 (m, 1H), 4.32 (d,



4-yl}oxy)phenyl]urea
J = 6.0 Hz, 2H), 4.08 (s, 2H), 3.82 (m,




1H), 3.67 (m, 1H), 3.59(m, 1H), 3.40-




3.15 (m, 2H), 1.90 (m, 2H), 1.52 (m, 2H),




1.10 (d, J = 6.1Hz, 6H)


447
1-(4-{[1-(2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


hydroxy-2-
8.48 (m, 2H), 7.88 (s, 1H), 7.52 (d, J = 1.2
m/e 452


methylpropanoyl)piperidin-
Hz, 1H), 7.38 (s, 1H), 7.30 (m, 2H), 6.87
(M + H) +


4-yl]oxy}phenyl)-
(m, 2H), 6.83 (dd, J = 7.0, 1.6Hz, 1H),



3-(imidazo[1,2-
6.62 (t, J = 6.0 Hz, 1H), 5.39 (s, 1H), 4.48



a]pyridin-7-
(m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 4.10-



ylmethyl)urea
3.40 (m, 2H), 3.40-3.15 (m, 2H), 1.90




(m, 2H), 1.54 (m, 2H), 1.31 (s, 6H)


448
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.49 (m, 2H), 7.90 (s, 1H), 7.54 (d, J = 1.2
m/e 464


ylmethyl)-3-[4-
Hz, 1H), 7.39 (s, 1H), 7.31 (m, 2H), 6.86
(M + H) +


({1-[(2R)-
(m, 3H), 6.62 (t, J = 6.0 Hz, 1H), 4.67 (m,



tetrahydrofuran-2-
1H), 4.48 (m, 1H), 4.32 (d, J = 6.0 Hz,



ylcarbonyl]piperidin-
2H), 3.78 (m, 4H), 3.45-3.15 (m, 2H),



4-yl}oxy)phenyl]urea
2.10-1.75 (m, 6H), 1.53 (m, 2H)


449
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.48 (m, 2H), 7.89 (s, 1H), 7.52 (d, J = 1.2
m/e 464


ylmethyl)-3-[4-
Hz, 1H), 7.38 (s, 1H), 7.31 (m, 2H), 6.87
(M + H) +


({1-[(2S)-
(m, 2H), 6.83 (dd, J = 7.0, 1.6Hz, 1H),



tetrahydrofuran-2-
6.62 (t, J = 6.0 Hz, 1H), 4.67 (m, 1H),



ylcarbonyl]piperidin-
4.48 (m, 1H), 4.32 (d, J = 6.0 Hz, 2H),



4-yl}oxy)phenyl]urea
3.78 (m, 4H), 3.45-3.16 (m, 2H), 2.09-




1.92 (m, 2H), 2.09-1.92 (m, 4H), 1.53




(m, 2H)


450
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.48 (m, 2H), 7.88 (s, 1H), 7.51 (d, J = 1.2
m/e 478


ylmethyl)-3-(4-
Hz, 1H), 7.38 (s, 1H), 7.31 (m, 2H), 6.87
(M + H) +


{[1-(tetrahydro-
(m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H),



2H-pyran-4-
6.62 (t, J = 6.0 Hz, 1H), 4.48 (m, 1H),



ylcarbonyl)piperidin-
4.32 (d, J = 6.0 Hz, 2H), 3.88-3.71 (m,



4-yl]oxy}phenyl)urea
4H), 3.38 (m, 2H), 3.34-3.16 (m, 1H),




3.22 (m, 1H), 2.89 (m, 1H), 1.91 (m, 2H),




1.67-1.40 (m, 6H)


451
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm
(ESI(+))


a]pyridin-7-
8.48 (m, 2H), 7.88 (s, 1H), 7.52 (bs, 1H),
m/e 492


ylmethyl)-3-(4-
7.38 (bs, 1H), 7.31 (m, 2H), 6.87 (m, 2H),
(M + H) +


{[1-(tetrahydro-
6.83 (dd, J = 7.0, 1.5Hz, 1H), 6.62 (t, J =



2H-pyran-4-
6.0 Hz, 1H), 4.47 (m, 1H), 4.32 (d, J = 6.0



ylacetyl)piperidin-
Hz, 2H), 3.89-3.75 (m, 3H), 3.70 (m,



4-yl]oxy}phenyl)urea
1H), 3.40-3.17 (m, 4H), 2.26 (m, 2H),




1.89 (m, 3H), 1.60-1.40 (m, 4H), 1.19




(m, 2H)


726
1-(4-{[1-(3-

(ESI(+))


fluorobenzoyl)piperidin-

m/e 488


4-yl]oxylphenyl)-3-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)urea



727
1-(4-{[1-(2,4-

(ESI(+))


difluorobenzoyl)piperidin-

m/e 506


4-yl]oxy}phenyl)-3-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)urea



728
1-(4-{[1-(2,5-

(ESI(+))


difluorobenzoyl)piperidin-

m/e 506


4-yl]oxy}phenyl)-3-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)urea



729
1-(4-{[1-(3,4-

(ESI(+))


difluorobenzoyl)piperidin-

m/e 506


4-yl]oxy}phenyl)-3-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)urea



730
1-(4-{[1-(3,5-

(ESI(+))


difluorobenzoyl)piperidin-

m/e 506


4-yl]oxy}phenyl)-3-

(M + H) +


(imidazo[1,2-




a]pyridin-7-




ylmethyl)urea
































































































































Example 452
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea
Example 452A
1-(4-(azetidin-3-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-(3-(imidazo[1,2-a]pyridin-7-ylmethyl)ureido)phenyl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 452B
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropanoyl)azetidin-3-yl]phenyl}urea
The title compound was prepared as described in Example 1A, substituting 1-(4-(azetidin-3-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66 (s, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.51 (s, 1H), 7.39 (m, 3H), 7.22 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.52 (m, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.20 (m, 1H), 4.08 (dd, J=8.5, 5.3 Hz, 1H), 3.76 (m, 2H), 2.49 (m, 1H), 0.99 (d, J=6.8 Hz, 6H); (ESI(+)) m/e 392 (M+H) + .





TABLE 22



The following Examples were prepared essentially as described in Example 452,

substituting the appropriate carboxylic acid in Example 452B.






Ex
Name
1 H NMR
MS



453
1-(imidazo[1,2-a]pyridin-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66
(ESI(+))


7-ylmethyl)-3-(4-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 406


{1-[(2S)-2-
1H), 7.52 (s, 1H), 7.40 (m, 3H), 7.22 (m,
(M + H) +


methylbutanoyl]azetidin-
2H), 6.84 (dd, J = 7.0, 1.6 Hz, 1H), 6.70 (m,



3-yl}phenyl)urea
1H), 4.52 (m, 1H), 4.33 (d, J = 6.0 Hz, 2H),




4.21 (m, 1H), 4.06 (m, 1H), 3.76 (m, 2H),




2.27 (m, 1H), 1.50 (m, 1H), 1.30 (m, 1H),




0.98 (d, J = 6.8 Hz, 3H), 0.84 (t, J = 7.4 Hz,




3H)


454
1-{4-[1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66
(ESI(+))


(cyclopropylacetyl)azetidin-
(s, 1H), 8.49 (d, J = 7.0 Hz, 1H), 7.89 (s,
m/e 404


3-yl]phenyl}-3-
1H), 7.53 (d, J = 1.2 Hz, 1H), 7.40 (m, 3H),
(M + H) +


(imidazo[1,2-
7.22 (m, 2H), 6.85 (dd, J = 7.0, 1.6 Hz, 1H),



a]pyridin-7-
6.70 (t, J = 6.0 Hz, 1H), 4.45 (m, 1H), 4.33



ylmethyl)urea
(d, J = 6.0 Hz, 2H), 4.20 (m, 1H), 4.04 (m,




1H), 3.75 (m, 2H), 2.02 (d, J = 6.8 Hz, 2H),




0.94 (m, 1H), 0.44 (m, 2H), 0.11 (m, 2H)


455
1-[4-(1-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.68
(ESI(+))


benzoylazetidin-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 426


3-yl)phenyl]-3-
1H), 7.68 (m, 2H), 7.52 (m, 2H), 7.46 (m,
(M + H) +


(imidazo[1,2-
2H), 7.40 (m, 3H), 7.26 (m, 2H), 6.83 (dd,



a]pyridin-7-
J = 7.0, 1.6 Hz, 1H), 6.72 (t, J = 6.0 Hz, 1H),



ylmethyl)urea
464 (m, 1H), 4.44 (m, 1H), 4.33 (d, J = 6.0




Hz, 2H), 4.27 (m, 1H), 3.98 (m, 1H), 3.85




(m, 1H)


456
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6) δ ppm 8.67
(ESI(+))


a]pyridin-7-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 422


ylmethyl)-3-(4-
1H), 7.51 (d, J = 1.2Hz, 1H), 7.40 (m, 3H),
(M + H) +


{1-[(propan-2-
7.22 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H),



yloxy)acetyl]azetidin-
6.71 (t, J = 6.0 Hz, 1H), 4.56 (m, 1H), 4.33



3-yl}phenyl)urea
(d, J = 6.0 Hz, 2H), 4.24 (m, 1H), 4.13 (m,




1H), 3.95 (s, 2H), 3.79 (m, 2H), 3.59 (m,




1H), 1.10 (d, J = 6.1Hz, 6H)


457
1-{4-[1-(2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66
(ESI(+))


hydroxy-2-
(s, 1H), 8.50 (d, J = 7.0 Hz, 1H), 7.90 (s,
m/e 408


methylpropanoyl)azetidin-
1H), 7.54 (d, J = 1.2Hz, 1H), 7.40 (m, 3H),
(M + H) +


3-yl]phenyl}-3-
7.21 (m, 2H), 6.86 (dd, J = 7.0, 1.6 Hz, 1H),



(imidazo[1,2-
6.70 (t, J = 6.0 Hz, 1H), 5.09 (s, 1H), 4.75



a]pyridin-7-
(m, 1H), 4.32 (m, 3H), 4.22 (m, 1H), 3.74



ylmethyl)urea
(m, 2H), 1.27 (s, 6H)


458
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.73
(ESI(+))


a]pyridin-7-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 420


ylmethyl)-3-(4-
1H), 7.51 (s, 1H), 7.40 (m, 3H), 7.22 (m,
(M + H) +


{1-[(2R)-
2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.78 (t,



tetrahydrofuran-
J = 6.0 Hz, 1H), 4.60 (m, 1H), 4.37 (m, 1H),



2-ylcarbonyl]azetidin-
4.33 (d, J = 6.0 Hz, 2H), 4.24 (m, 1H), 4.16



3-yl}phenyl)urea
(m, 1H), 3.86-3.69 (m, 4H), 2.04 (m, 1H),




1.96 (m, 1H), 1.82 (m, 2H)


459
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66
(ESI(+))


a]pyridin-7-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 420


ylmethyl)-3-(4-
1H), 7.51 (s, 1H), 7.40 (m, 3H), 7.22 (m,
(M + H) +


{1-[(2S)-
2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.74-



tetrahydrofuran-2-
6.67 (m, 1H), 4.60 (m, 1H), 4.37 (m, 1H),



ylcarbonyl]azetidin-3-
4.33 (d, J = 6.0 Hz, 2H), 4.23 (m, 1H), 4.15



yl}phenyl)urea
(m, 1H), 3.85-3.69 (m, 4H), 2.04 (m, 1H),




1.96 (m, 1H), 1.81 (m, 2H)


460
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.67
(ESI(+))


a]pyridin-7-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 434


ylmethyl)-3-{4-
1H), 7.51 (d, J = 1.1 Hz, 1H), 7.40 (m, 3H),
(M + H) +


[1-(tetrahydro-
7.22 (m, 2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H),



2H-pyran-4-
6.71 (t, J = 6.0 Hz, 1H), 4.54 (m, 1H), 4.33



ylcarbonyl)azetidin-3-
(d, J = 6.0 Hz, 2H), 4.21 (m, 1H), 4.13 (m,



yl]phenyl}urea
1H), 3.85 (m, 2H), 3.77 (m, 2H), 3.40-




3.25 (m, 2H), 2.50 (m, 1H), 1.58 (m, 4H)


461
1-(imidazo[1,2-
1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.70
(ESI(+))


a]pyridin-7-
(s, 1H), 8.48 (d, J = 7.0 Hz, 1H), 7.88 (s,
m/e 448


ylmethyl)-3-{4-
1H), 7.51 (s, 1H), 7.40 (m, 3H), 7.21 (m,
(M + H) +


[1-(tetrahydro-
2H), 6.83 (dd, J = 7.0, 1.6 Hz, 1H), 6.75 (t,



2H-pyran-4-
J = 6.0 Hz, 1H), 4.47 (m, 1H), 4.33 (d, J =



ylacetyl)azetidin-3-
6.0 Hz, 2H), 4.19 (m, 1H), 4.05 (m, 1H),



yl]phenyl}urea
3.85-3.69 (m, 4H), 3.28 (m, 2H), 2.03 (d,




J = 1.8 Hz, 2H), 1.90 (m, 1H), 1.57 (m, 2H),




1.21 (m, 2H)






























































































Example 462
4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
Example 462A
methyl 4-(2-cyclopentylacetamido)-2-fluorobenzoate
The title compound was prepared as described in Example 52A, substituting 2-cyclopentylacetyl chloride for 2-cyclopentylacetyl chloride and methyl 4-amino-2-fluorobenzoate for methyl 4-aminobenzoate.
Example 462B
4-(2-cyclopentylacetamido)-2-fluorobenzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-(2-cyclopentylacetamido)-2-fluorobenzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 462C
4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)-2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (501 MHz, DMSO-d 6 ) δ ppm 10.24 (s, 1H), 8.70-8.63 (m, 1H), 8.46 (s, 1H), 7.95 (s, 1H), 7.74-7.62 (m, 2H), 7.58-7.50 (m, 2H), 7.32 (dd, J=8.5, 1.9 Hz, 1H), 7.24 (dd, J=9.2, 1.7 Hz, 1H), 4.45 (d, J=5.9 Hz, 2H), 2.37-2.31 (m, 2H), 2.31-2.15 (m, 1H), 1.81-1.69 (m, 2H), 1.67-1.45 (m, 4H), 1.25-1.12 (m, 2H); MS (ESI(+)) m/e 395 (M+H) + .
Example 464
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[6-(morpholin-4-yl)pyridin-3-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.34 (t, J=6.0 Hz, 1H), 8.87 (d, J=7.0 Hz, 1H), 8.51 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.2 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 7.90 (dd, J=8.9, 2.6 Hz, 1H), 7.85 (d, J=3.9 Hz, 1H), 7.81 (s, 1H), 7.50-7.44 (m, 2H), 6.94 (d, J=9.0 Hz, 1H), 4.67 (d, J=5.9 Hz, 2H), 3.75-3.66 (m, 4H), 3.57-3.49 (m, 4H); MS (ESI(+)) m/e 420 (M+H).
Example 467
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
Example 467A
tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 467B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(pyrrolidin-3-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 467C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(pyrrolidin-3-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.02 (t, J=5.4 Hz, 1H), 8.48 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.68 (dd, J=3.9, 2.2 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 7.02 (dd, J=8.1, 3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.22-3.94 (m, 5H), 2.21-2.42 (m, 1H), 2.10-2.17 (m, 2H), 1.86-2.09 (m, 2H), 0.86-0.95 (m, 6H); MS (ESI(+)) m/e 411 (M+H) + .





TABLE 23



The following Examples were prepared essentially as described in Example

467, using an appropriate carboxylic acid in Example 467C.





Ex
Name
MS



540
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-
(ESI(+))


trifluoropropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 437



(M + H) +

541
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-
(ESI(+))


methylpropanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 397



(M + H) +

542
5-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)thiophene-2-carboxamide
m/e 431



(M + H) +

717
5-[1-(cyclopropylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 395



(M + H) +

718
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-
(ESI(+))


methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 445



(M + H) +

756
5-[1-(cyclopropylacetyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 409



(M + H) +

757
5-[1-(2-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 465



(M + H) +

758
5-{1-[(4-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 463


carboxamide
(M + H) +

759
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-
(ESI(+))


methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 461



(M + H) +

760
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-
(ESI(+))


methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 461



(M + H) +

761
5-{1-[(3-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 463



(M + H) +

762
5-[1-(3-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 449



(M + H) +

763
5-[1-(4-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 449



(M + H) +

764
5-{1-[(3,5-difluorophenyl)acetyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 481



(M + H) +

765
5-{1-[(2-fluorophenyl)acetyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 463



(M + H) +

766
5-[1-(4-cyanobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 456



(M + H) +

767
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-
(ESI(+))


methyloxetan-3-yl)carbonyl]pyrrolidin-3-yl}thiophene-
m/e 425


2-carboxamide
(M + H) +

768
5-[1-(3,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 467



(M + H) +

769
5-[1-(cyclopentylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 421



(M + H) +

770
5-[1-(4-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 465



(M + H) +

771
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-
(ESI(+))


pyrrol-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-
m/e 434


carboxamide
(M + H) +

772
5-[1-(2,4-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 467



(M + H) +

773
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-4-
(ESI(+))


ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 432



(M + H) +

774
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyridin-2-
(ESI(+))


ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 432



(M + H) +

775
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-
(ESI(+))


pyrazol-4-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-
m/e 435


carboxamide
(M + H) +

776
5-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 449



(M + H) +

777
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2E)-2-
(ESI(+))


methylpent-2-enoyl]pyrrolidin-3-yl}thiophene-2-
m/e 423


carboxamide
(M + H) +

778
5-{1-[(2,5-dimethylfuran-3-yl)carbonyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 449



(M + H) +

779
5-[1-(3-chlorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 465



(M + H) +

780
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-
(ESI(+))


propanoylpyrrolidin-3-yl)thiophene-2-carboxamide
m/e 383



(M + H) +

781
5-{1-[(1-cyanocyclopropyl)carbonyl]pyrrolidin-3-yl}-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 420



(M + H) +

782
5-(1-butanoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)thiophene-2-carboxamide
m/e 397



(M + H) +

783
5-[1-(furan-2-ylcarbonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 421



(M + H) +

784
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4-
(ESI(+))


methoxybenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 461



(M + H) +

785
5-[1-(2,5-difluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 467



(M + H) +

786
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(thiophen-2-
(ESI(+))


ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 437



(M + H) +

787
5-[1-(2,2-dimethylpropanoyl)pyrrolidin-3-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 411


carboxamide
(M + H) +

788
5-[1-(3,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 425



(M + H) +

791
5-[1-(2,2-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 425



(M + H) +

792
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(pyrazin-2-
(ESI(+))


ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 433



(M + H) +

793
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-}1-[(3-
(ESI(+))


methylthiophen-2-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-
m/e 451


carboxamide
(M + H) +

794
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-
(ESI(+))


methylbenzoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 445



(M + H) +

795
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-}1-[(1-
(ESI(+))


methylcyclopropyl)carbonyl]pyrrolidin-3-yl}thiophene-2-
m/e 409


carboxamide
(M + H) +

796
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-
(ESI(+))


trifluorobutanoyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 451



(M + H) +

797
5-{1-[(3,5-dimethyl-1,2-oxazol-4-yl)carbonyl]pyrrolidin-
(ESI(+))


3-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-
m/e 450


carboxamide
(M + H) +

798
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5[1-(pyridin-3-
(ESI(+))


ylcarbonyl)pyrrolidin-3-yl]thiophene-2-carboxamide
m/e 432



(M + H) +

799
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(1-methyl-1H-
(ESI(+))


pyrazol-5-yl)carbonyl]pyrrolidin-3-yl}thiophene-2-
m/e 435


carboxamide
(M + H) +

800
5-[1-(2,3-dimethylbutanoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)thiophene-2-carboxamide
m/e 425



(M + H) +





































































































































































Example 468
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropanoyl)amino]cyclobutyl}thiophene-2-carboxamide
Example 468A
5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 324A, substituting N-cyclobutylidene-2-methylpropane-2-sulfinamide for N-(oxetan-3-ylidene)propane-2-sulfinamide.
Example 468B
5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 468C
5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared in Example 324C, substituting 5-(1-(1,1-dimethylethylsulfinamido)cyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 5-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide.
Example 468D
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.97 (t, J=5.9 Hz, 1H), 8.53 (s, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 7.52 (d, J=1.4 Hz, 1H), 7.38 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=6.8, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.36-2.48 (m, 5H), 1.86-2.01 (m, 2H), 0.99 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 397 (M+H) + .
Example 469
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3-methylbutanoyl)amino]cyclobutyl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.97 (t, J=5.9 Hz, 1H), 8.59 (s, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.05 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.1, 1.7 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.39-2.47 (m, 4H), 1.83-2.03 (m, 5H), 0.87 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 411 (M+H) + .
Example 470
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1-{[(2S)-2-methylbutanoyl]amino}cyclobutyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.97 (t, J=6.1 Hz, 1H), 8.57 (s, 1H), 8.47 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=4.1 Hz, 1H), 7.51 (d, J=1.4 Hz, 1H), 7.37 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 2.37-2.49 (m, 4H), 2.13-2.26 (m, 1H), 1.84-2.01 (m, 2H), 1.40-1.59 (m, 1H), 1.20-1.36 (m, 1H), 0.97 (d, J=6.8 Hz, 3H), 0.82 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 411 (M+H).
Example 471
5-[1-(benzoylamino)cyclobutyl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.17 (s, 1H), 8.98 (t, J=5.9 Hz, 1H), 8.46 (d, J=6.1 Hz, 1H), 7.84-7.90 (m, 3H), 7.65 (d, J=4.1 Hz, 1H), 7.43-7.57 (m, 4H), 7.37 (s, 1H), 7.14 (d, J=4.1 Hz, 1H), 6.81 (dd, J=6.8, 1.7 Hz, 1H), 4.44 (d, J=6.1 Hz, 2H), 2.61-2.73 (m, 2H), 2.50-2.60 (m, 2H), 1.91-2.07 (m, 2H); MS (ESI(+)) m/e 431 (M+H).
Example 472
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3,3,3-trifluoropropanoyl)amino]cyclobutyl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.08 (s, 1H), 9.00 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.8 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=3.7 Hz, 1H), 7.52 (s, 1H), 7.38 (s, 1H), 7.07 (d, J=3.7 Hz, 1H), 6.83 (dd, J=6.8, 1.7 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 3.19-3.36 (m, 2H), 2.43-2.53 (m, 4H), 1.86-2.03 (m, 2H); MS (ESI(+)) m/e 437 (M+H) + .
Example 473
N-(1-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}cyclobutyl)tetrahydro-2H-pyran-4-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(1-aminocyclobutyl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.97 (t, J=6.1 Hz, 1H), 8.60 (s, 1H), 8.48 (d, J=7.1 Hz, 1H), 7.88 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H), 7.37 (s, 1H), 7.04 (d, J=3.7 Hz, 1H), 6.82 (dd, J=7.0, 1.5 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.81-3.89 (m, 2H), 3.24-3.36 (m, 2H), 2.33-2.48 (m, 5H), 1.84-2.00 (m, 2H), 1.47-1.65 (m, 4H); MS (ESI(+)) m/e 439 (M+H) + .
Example 474
tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yloxy)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.98 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.89 (m, 3H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.92 (m, 2H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 5.06 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 2H), 3.80 (m, 2H), 1.39 (s, 9H); MS (ESI(+)) m/e 423 (M+H) + .
Example 485
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
Example 485A
tert-butyl 4-((4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
Example 485B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-((4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1 H NMR (300 MHz, methanol-d 4 ) δ 8.76 (dd, J=7.1, 0.9 Hz, 1H), 8.19 (dd, J=2.2, 0.7 Hz, 1H), 8.07 (s, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.83 (d, J=0.6 Hz, 2H), 7.72 (d, J=3.8 Hz, 1H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.75 (s, 2H), 4.15 (d, J=7.0 Hz, 2H), 3.48-3.36 (m, 2H), 3.08-2.91 (m, 2H), 2.37-2.15 (m, 1H), 1.85 (d, J=14.0 Hz, 2H), 1.63-1.43 (m, 2H); MS (ESI(+)) m/e 421 (M+H) + .
Example 486
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
Example 486A
1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
To a solution of imidazo[1,2-a]pyridin-7-ylmethanamine (500 mg, 3.40 mmol) in dichloromethane (17 ml) at room temperature was added 1-bromo-4-isocyanatobenzene (680 mg, 3.40 mmol) as a single portion. The resulting suspension was stirred overnight and then filtered with dichloromethane washes to give the title compound.
Example 486B
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 51A, substituting substituting 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.02 (d, J=0.8 Hz, 1H), 7.88 (dd, J=1.2, 0.7 Hz, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.54-7.34 (m, 6H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.34 (d, J=5.9 Hz, 2H), 3.90 (d, J=7.1 Hz, 2H), 2.21-2.04 (m, 1H), 0.86 (d, J=6.7 Hz, 6H). MS (ESI(+)) m/e 389 (M+H) + .
Example 487
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-[4-(1-propyl-1H-pyrazol-4-yl)phenyl]urea
The title compound was prepared as described in Example 51A, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ 8.62 (s, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 8.04 (d, J=0.8 Hz, 1H), 7.90-7.86 (m, 1H), 7.76 (d, J=0.8 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.46-7.35 (m, 5H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.69 (t, J=6.0 Hz, 1H), 4.34 (d, J=5.9 Hz, 2H), 4.04 (t, J=6.9 Hz, 2H), 1.91-1.73 (m, 2H), 1.26-1.05 (m, 1H), 0.85 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 375 (M+H) + .
Example 489
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-phenoxybenzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-phenoxybenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (m, 2H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.44 (m, 2H), 7.38 (s, 1H), 7.22 (m, 1H), 7.14-6.98 (m, 4H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H); MS (ESI(+)) m/e 344 (M+H) + .
Example 490
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide
Example 490A
4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 490B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-methylpropanoyl)azetidin-3-yl]benzamide
The title compound was prepared as described in Example 1A, substituting-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and 2-methylpropanoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.10 (t, J=5.9 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.91 (m, 3H), 7.52 (d, J=1.0 Hz, 1H), 7.48 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.58 (t, J=8.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (t, J=9.0 Hz, 1H), 4.18 (dd, J=8.4, 6.0 Hz, 1H), 3.92 (m, 1H), 3.84 (m, 1H), 3.17 (d, J=5.0 Hz, 1H), 1.00 (dd, J=6.8, 1.6 Hz, 6H); MS (ESI(+)) m/e 377 (M+H) + .





TABLE 24



The following Examples were prepared essentially as described in Example

490, using an appropriate carboxylic acid in Example 490B.





Ex
Name
MS



547
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2S)-2-
(ESI(+))


methylbutanoyl]azetidin-3-yl}benzamide
m/e 391



(M + H) +

548
4-[1-(cyclopropylacetyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 389



(M + H) +

549
4-(1-benzoylazetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-
(ESI(+))


ylmethyl)benzamide
m/e 411



(M + H) +

550
4-[1-(2-hydroxy-2-methylpropanoyl)azetidin-3-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 393



(M + H) +

551
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(tetrahydro-2H-
(ESI(+))


pyran-4-ylacetyl)azetidin-3-yl]benzamide
m/e 433



(M + H) +

552
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-2-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 417



(M + H) +

628
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(2-
(ESI(+))


methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide
m/e 389



(M + H) +

629
4-[1-(cyclopentylacetyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 417



(M + H) +

630
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methylpentanoyl)azetidin-3-yl]benzamide
m/e 405



(M + H) +

631
4-[1-(cyclopentylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 403



(M + H) +

632
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-
(ESI(+))


methylcyclopropyl)carbonyl]azetidin-3-yl}benzamide
m/e 389



(M + H) +

633
4-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-N-
(ESI(+))


(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
m/e 391



(M + H) +

634
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-5-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 418



(M + H) +

635
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrazin-2-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 413



(M + H) +

636
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


methoxybenzoyl)azetidin-3-yl]benzamide
m/e 441



(M + H) +

637
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-4-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 418



(M + H) +

638
4-[1-(2-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 429



(M + H) +

639
4-[1-(furan-2-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 401



(M + H) +

640
4-[1-(3-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 429



(M + H) +

641
4-[1-(2,4-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 447



(M + H) +

642
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-
(ESI(+))


pyrazol-3-yl)carbonyl]azetidin-3-yl}benzamide
m/e 415



(M + H) +

643
4-[1-(2-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 445



(M + H) +

644
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(2-
(ESI(+))


methylbenzoyl)azetidin-3-yl]benzamide
m/e 425



(M + H) +

645
4-[1-(4-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 445



(M + H) +

646
4-[1-(3-chlorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 445



(M + H) +

647
4-[1-(2,2-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 405



(M + H) +

648
4-[1-(3,5-difluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 447



(M + H) +

649
4-[1-(4-fluorobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 429



(M + H) +

650
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-
(ESI(+))


methylbenzoyl)azetidin-3-yl]benzamide
m/e 425



(M + H) +

651
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methylbutanoyl)azetidin-3-yl]benzamide
m/e 391



(M + H) +

652
4-[1-(3,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 405



(M + H) +

653
4-[1-(3-cyanobenzoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 436



(M + H) +

654
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methoxybenzoyl)azetidin-3-yl]benzamide
m/e 441



(M + H) +

655
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(4-
(ESI(+))


methoxybenzoyl)azetidin-3-yl]benzamide
m/e 441



(M + H) +

565
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-methyl-1H-
(ESI(+))


pyrrol-2-yl)carbonyl]azetidin-3-yl}benzamide
m/e 414



(M + H) +

657
4-[1-(cyclohexylacetyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 431



(M + H) +

658
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-4-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 412



(M + H) +

659
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyridin-3-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 412



(M + H) +

660
4-[1-(cyclohexylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 417



(M + H) +

661
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4[1-(pyridin-2-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 412



(M + H) +

662
4-[1-(furan-3-ylcarbonyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 401



(M + H) +

663
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4[1-(pyrimidin-4-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 413



(M + H) +

664
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(1,3-thiazol-2-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 418



(M + H) +

665
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(1-
(ESI(+))


methylcyclohexyl)carbonyl]azetidin-3-yl}benzamide
m/e 431



(M + H) +

666
4-[1-(2,3-dimethylbutanoyl)azetidin-3-yl]-N-(imidazo[1,2-
(ESI(+))


a]pyridin-7-ylmethyl)benzamide
m/e 405



(M + H) +

667
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(3-
(ESI(+))


methylbenzoyl)azetidin-3-yl]benzamide
m/e 425



(M + H) +

668
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(thiophen-3-
(ESI(+))


ylcarbonyl)azetidin-3-yl]benzamide
m/e 417



(M + H) +

669
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-
(ESI(+))


(trifluoromethoxy)benzoyl]azetidin-3-yl}benzamide
m/e 495



(M + H) +

670
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[(3-
(ESI(+))


methylthiophen-2-yl)carbonyl]azetidin-3-yl}benzamide
m/e 431



(M + H) +

671
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{1-[3-
(ESI(+))


(trifluoromethyl)benzoyl]azetidin-3-yl}benzamide
m/e 479



(M + H) +











































































































































































Example 491
tert-butyl 4-{4-[(3-chloroimidazo[1,2-a]pyridin-6-yl)carbamoyl]phenyl}piperidine-1-carboxylate
A solution of tert-butyl 4-(4-(imidazo[1,2-a]pyridin-6-ylcarbamoyl)phenyl)piperidine-1-carboxylate (0.015 g, 0.036 mmol) in chloroform (0.618 ml) and methanol (0.095 ml) was treated with N-chlorosuccinimide (5.24 mg, 0.039 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under a stream of warm nitrogen. The residue was purified by normal phase flash chromatography to provide the title compound. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.23 (s, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.62-7.51 (m, 3H), 7.42 (d, J=8.3 Hz, 2H), 4.27-4.19 (m, 2H), 2.96-2.76 (m, 3H), 1.90-1.82 (m, 2H), 1.70-1.57 (m, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 455 (M+H) + .
Example 492
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide
Example 492A
(R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl (3R)-3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 492B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(3R)-1-(2-methylpropanoyl)pyrrolidin-3-yl]oxy}benzamide
The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.94-7.86 (m, 2H), 7.80 (bs, 1H), 7.48 (dd, J=7.0, 1.6 Hz, 1H), 7.11-7.01 (m, 2H), 5.23-5.11 (m, 1H), 4.76 (s, 2H), 3.92-3.47 (m, 4H), 2.87-2.64 (m, 1H), 2.36-2.16 (m, 2H), 1.16-1.01 (m, 6H); MS (ESI(+)) m/e 407 (M+H) + .
Example 493
4-{[(3R)-1-benzoylpyrrolidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.74 (t, J=6.6 Hz, 1H), 8.20-8.14 (m, 1H), 8.01-7.96 (m, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.82-7.76 (m, 1H), 7.59-7.39 (m, 6H), 7.10 (d, J=8.6 Hz, 1H), 7.00 (d, J=8.6 Hz, 1H), 5.24-5.07 (m, 1H), 4.75 (d, J=12.3 Hz, 2H), 3.99-3.70 (m, 3H), 3.66-3.56 (m, 1H), 2.39-2.19 (m, 2H); MS (ESI(+)) m/e 441 (M+H) + .
Example 494
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(3S)-tetrahydrofuran-3-ylcarbonyl]pyrrolidin-3-yl}oxy)benzamide
The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-tetrahydrofuran-3-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.01-7.97 (m, 1H), 7.93-7.86 (m, 2H), 7.82-7.77 (m, 1H), 7.51-7.45 (m, 1H), 7.10-7.01 (m, 2H), 5.23-5.12 (m, 1H), 4.75 (s, 2H), 4.05-3.92 (m, 1H), 3.94-3.63 (m, 7H), 3.57-3.34 (m, 1H), 2.40-2.29 (m, 1H), 2.27-1.97 (m, 3H); MS (ESI(+)) m/e 435 (M+H) + .
Example 495
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({(3R)-1-[(2S)-2-methylbutanoyl]pyrrolidin-3-yl}oxy)benzamide
The title compound was prepared as described in Example 1A, substituting (R)—N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yloxy)benzamide for 3-methylbutan-1-amine and (S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.94-7.86 (m, 2H), 7.82-7.77 (m, 1H), 7.48 (d, J=7.1 Hz, 1H), 7.10-7.00 (m, 2H), 5.22-5.11 (m, 1H), 4.76 (s, 2H), 3.91-3.49 (m, 4H), 2.70-2.49 (m, 1H), 2.35-2.17 (m, 2H), 1.73-1.59 (m, 1H), 1.50-1.36 (m, 1H), 1.14-1.03 (m, 3H), 0.93-0.86 (m, 3H); MS (ESI(+)) m/e 421 (M+H) + .
Example 496
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-phenoxyphenyl)urea
The title compound was prepared as described in Example 1C, substituting 4-phenoxyaniline for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.68 (s, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (t, J=0.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.44 (m, 2H), 7.39 (m, 1H), 7.34 (m, 2H), 7.07 (m, 1H), 6.93 (m, 4H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H); MS (ESI(+)) m/e 359 (M+H) + .
Example 497
5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 497A
5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 51A, substituting 5-bromothiophene-2-carboxylic acid for 4-bromoaniline.
Example 497B
5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.11 (t, J=6.0 Hz, 1H), 8.90 (dd, J=7.1, 1.0 Hz, 1H), 8.46 (s, 1H), 8.15 (d, J=0.9 Hz, 1H), 7.81 (s, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.71-7.64 (m, 1H), 7.23 (d, J=3.8 Hz, 1H), 7.16 (dd, J=7.1, 1.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 3.93 (d, J=7.1 Hz, 2H), 2.20-2.04 (m, 1H), 0.86 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 381 (M+H) + .
Example 543
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide
Example 543A
2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 2-bromothiazole-5-carboxylic acid for 4-nitrobenzoic acid.
Example 543B
tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiazole-5-carboxamide for 4-bromoaniline.
Example 543C
tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 543D
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)thiazol-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 543E
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.33 (s, 1H), 7.89 (bs, 1H), 7.52 (d, J=1.0 Hz, 1H), 7.40 (bs, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=6.1 Hz, 2H), 4.44 (d, J=13.4 Hz, 1H), 4.02 (d, J=13.1 Hz, 1H), 3.34-3.27 (m, 1H), 3.19 (t, J=11.9 Hz, 1H), 2.95-2.84 (m, 1H), 2.72 (t, J=12.1 Hz, 1H), 2.13-2.02 (m, 2H), 1.68-1.43 (m, 2H), 1.04-0.96 (m, 6H); MS (ESI(+)) m/e 412 (M+H) + .
Example 544
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)piperidin-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) 9.23 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 7.92-7.87 (m, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.6 Hz, 1H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 4.51-4.41 (m, 3H), 3.96 (d, J=13.8 Hz, 1H), 3.34-3.24 (m, 1H), 3.16 (t, J=11.7 Hz, 1H), 2.71 (t, J=12.2 Hz, 1H), 2.21 (dd, J=7.0, 2.3 Hz, 2H), 2.10-2.00 (m, 2H), 1.61 (qd, J=12.7, 4.3 Hz, 1H), 1.49 (qd, J=12.5, 4.4 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H) + .
Example 545
2-(1-benzoylpiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) ppm 9.24 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.34 (s, 1H), 7.89 (s, 1H), 7.53 (d, J=1.1 Hz, 1H), 7.43 (ddd, J=9.6, 6.8, 3.7 Hz, 6H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.48 (d, J=5.9 Hz, 1H), 3.72-3.58 (m, 1H), 3.26-3.13 (m, 1H), 3.06-2.91 (m, 1H), 2.17-1.95 (m, 2H), 1.72-1.62 (m, 2H); MS (ESI(+)) m/e 446 (M+H) + .
Example 546
4-[(cyclopentylacetyl)amino]-N-([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.78-8.72 (m, 1H), 8.40 (s, 1H), 7.90-7.83 (m, 2H), 7.75-7.67 (m, 3H), 7.25 (dd, J=7.0, 1.8 Hz, 1H), 4.75-4.69 (m, 2H), 2.44-2.25 (m, 3H), 1.95-1.76 (m, 2H), 1.78-1.50 (m, 4H), 1.35-1.17 (m, 2H); MS (ESI(+)) m/e 378 (M+H) + .
Example 553
5-[4-hydroxy-1-(3-methylbutanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 553A
5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-hydroxy-4-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 553B
5-[3-hydroxy-1-(2-methylpropanoyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-methylpropanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.98 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.87 (m, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.00 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.76 (s, 1H), 4.46 (d, J=5.9 Hz, 2H), 4.33-4.23 (m, 1H), 3.81-3.71 (m, 1H), 2.99-2.85 (m, 1H), 2.21 (d, J=7.0 Hz, 2H), 2.07-1.91 (m, 1H), 1.86-1.71 (m, 4H), 0.94-0.87 (m, 6H); MS (ESI(+)) m/e 441 (M+H) + .
Example 554
5-[4-hydroxy-1-(2-methylpropanoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.98 (s, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 7.01 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.77 (s, 1H), 4.46 (d, J=5.6 Hz, 2H), 4.33-4.22 (m, 1H), 3.88-3.74 (m, 1H), 2.98-2.82 (m, 2H), 1.82 (s, 4H), 1.05-0.96 (m, 6H); MS (ESI(+)) m/e 427 (M+H) + .
Example 555
5-[1-(3,3-dimethylbutanoyl)-4-hydroxypiperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3-dimethylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.98 (t, J=5.8 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.91-7.86 (m, 1H), 7.65 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.00 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.76 (s, 1H), 4.46 (d, J=6.0 Hz, 2H), 4.38-4.28 (m, 1H), 3.89-3.78 (m, 1H), 2.97-2.85 (m, 1H), 2.38-2.13 (m, 3H), 1.86-1.71 (m, 4H), 0.99 (s, 9H); MS (ESI(+)) m/e 455 (M+H) + .
Example 556
5-(1-benzoyl-4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting 5-(4-hydroxypiperidin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.98 (s, 1H), 8.48 (d, J=6.2 Hz, 1H), 7.88 (s, 1H), 7.66 (d, J=3.8 Hz, 1H), 7.53-7.35 (m, 7H), 7.06 (d, J=3.8 Hz, 1H), 6.83 (d, J=7.0 Hz, 1H), 5.83 (s, 1H), 4.46 (d, J=5.9 Hz, 3H), 4.52-4.26 (m, 1H), 1.93 (s, 5H); MS (ESI(+)) m/e 461 (M+H) + .
Example 557
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide
Example 557A
tert-butyl 3-(4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)phenyl)azetidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)azetidin-3-yl)benzoic acid for 4-nitrobenzoic acid.
Example 557B
4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)phenyl)azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 557C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)azetidin-3-yl]benzamide
In a 4 mL vial was mixed 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide bis(2,2,2-trifluoroacetate) (60 mg, 0.112 mmol) in anhydrous tetrahydrofuran (2 mL) at room temperature. To this mixture was added in portions 60% sodium hydride in mineral oil (22.45 mg, 0.561 mmol). This heterogeneous mixture was stirred 1 hour. To this was added propane-2-sulfonyl chloride (0.015 mL, 0.135 mmol) at and reaction mixture was stirred for 3 hours. The mixture was quenched with water, and product was extracted with 10% methanol/dichloromethane. The organic layers were combined, concentrated and purified by normal phase chromatography to give the title compound. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.07 (m, 1H), 8.47 (d, J=7.0 Hz, 1H), 7.90 (m, 3H), 7.48 (m, 3H), 7.37 (s, 1H), 6.84 (m, 1H), 4.50 (d, J=5.9 Hz, 2H), 4.22 (m, 2H), 3.93 (m, 3H), 3.48 (m, 1H), 1.25 (d, J=5.9 Hz, 6H); MS (ESI(+)) m/e 413 (M+H) + .
Example 558
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide
Example 558A
4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenoxy}azetidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 558B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[1-(2-methylpropanoyl)azetidin-3-yl]oxy}benzamide
The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 6.95 (m, 2H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 5.11 (m, 1H), 4.64 (dd, J=9.5, 6.4 Hz, 1H), 4.49 (d, J=5.8 Hz, 2H), 4.32 (dd, J=10.4, 6.3 Hz, 1H), 4.09 (m, 1H), 3.78 (dd, J=10.6, 3.9 Hz, 1H), 2.48 (m, 1H), 0.98 (t, J=6.7 Hz, 6H); MS (ESI(+)) m/e 393 (M+H) + .
Example 559
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-({1-[(2S)-2-methylbutanoyl]azetidin-3-yl}oxy)benzamide
The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and (2S)-2-methylbutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.95 (m, 2H), 6.85 (dd, J=6.9, 1.6 Hz, 1H), 5.11 (dd, J=6.4, 3.5 Hz, 1H), 4.63 (dd, J=9.5, 6.5 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 1H), 4.11 (m, 1H), 3.79 (m, 1H), 2.29 (m, 1H), 1.50 (m, 1H), 1.28 (m, 1H), 0.97 (t, J=6.0 Hz, 3H), 0.82 (m, 3H); MS (ESI(+)) m/e 407 (M+H) + .
Example 560
4-{[1-(cyclopropylacetyl)azetidin-3-yl]oxy}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and cyclopropylacetic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.94 (m, 2H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 5.10 (m, 1H), 4.57 (dd, J=9.5, 6.5 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (dd, J=10.6, 6.5 Hz, 1H), 4.08 (dd, J=9.6, 3.8 Hz, 1H), 3.78 (dd, J=10.6, 3.9 Hz, 1H), 2.03 (d, J=6.8 Hz, 2H), 0.91 (m, 1H), 0.44 (m, 2H), 0.10 (m, 2H); MS (ESI(+)) m/e 405 (M+H) + .
Example 561
4-[(1-benzoylazetidin-3-yl)oxy]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting 4-(azetidin-3-yloxy)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.99 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.90 (m, 3H), 7.66 (m, 2H), 7.59-7.42 (m, 4H), 7.37 (s, 1H), 6.95 (m, 2H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 5.17 (m, 1H), 4.71 (m, 1H), 4.57 (m, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.33 (m, 1H), 4.02 (m, 1H); MS (ESI(+)) m/e 427 (M+H) + .
Example 563
tert-butyl 4-{4-[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.11 (t, J=5.9 Hz, 1H), 8.89 (dd, J=7.0, 0.9 Hz, 1H), 8.44 (s, 1H), 7.89-7.83 (m, 2H), 7.67-7.65 (m, 1H), 7.40-7.34 (m, 2H), 7.15 (dd, J=7.0, 1.8 Hz, 1H), 4.62-4.57 (m, 2H), 4.14-4.03 (m, 2H), 2.91-2.67 (m, 3H), 1.82-1.71 (m, 2H), 1.60-1.37 (m, 11H); MS (ESI(+)) m/e 436 (M+H) + .
Example 564
2-cyclopentyl-N-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)acetamide
The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.68 (s, 1H), 8.89 (d, J=7.0 Hz, 1H), 8.64 (s, 1H), 8.45 (s, 1H), 7.65 (s, 1H), 7.47-7.41 (m, 2H), 7.34-7.28 (m, 2H), 7.14 (dd, J=7.0, 1.8 Hz, 1H), 6.78 (t, J=6.0 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H), 2.29-2.15 (m, 3H), 1.79-1.68 (m, 2H), 1.66-1.43 (m, 4H), 1.24-1.11 (m, 2H); MS (ESI(+)) m/e 393 (M+H) + .
Example 565
tert-butyl 4-(4-{[([1,2,4]triazolo[1,5-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and [1,2,4]triazolo[1,5-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.89 (d, J=7.0 Hz, 1H), 8.66 (s, 1H), 8.45 (s, 1H), 7.64 (s, 1H), 7.36-7.30 (m, 2H), 7.14 (dd, J=7.0, 1.8 Hz, 1H), 7.12-7.07 (m, 2H), 6.80 (t, J=6.0 Hz, 1H), 4.43 (d, J=6.0 Hz, 2H), 4.10-4.00 (m, 2H), 2.90-2.63 (m, 2H), 2.66-2.54 (m, 1H), 1.75-1.67 (m, 2H), 1.49-1.35 (s, 11H); MS (ESI(+)) m/e 451 (M+H) + .
Example 566
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-1-ylcarbonyl)benzamide
The title compound was prepared as described in Example 1A, substituting piperidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.18 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.96 (m, 2H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.47 (m, 2H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.59 (m, 2H), 3.24 (m, 2H), 1.66-1.38 (m, 6H); MS (ESI(+)) m/e 363 (M+H) + .
Example 567
4-[1-(ethylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 557C, substituting ethane sulfonyl chloride for propane-2-sulfonyl chloride. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.93 (m, 2H), 7.88 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.49 (m, 2H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.23 (m, 2H), 3.95 (m, 3H), 3.19 (q, J=7.3 Hz, 2H), 1.25 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 399 (M+H) + .
Example 568
4-[1-(cyclopropylsulfonyl)azetidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 557C, substituting cyclopropane sulfonyl chloride for propane-2-sulfonyl chloride. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.10 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.93 (m, 2H), 7.88 (m, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.50 (m, 2H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.26 (t, J=7.7 Hz, 2H), 3.99 (m, 3H), 2.85 (m, 1H), 1.06 (m, 2H), 0.97 (m, 2H); MS (ESI(+)) m/e 411 (M+H) + .
Example 569
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)azetidin-3-yl]benzamide
The title compound was prepared as described in Example 557C, substituting benzene sulfonyl chloride for propane-2-sulfonyl chloride.— 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.47 (m, 1H), 7.92-7.82 (m, 4H), 7.75 (m, 4H), 7.51 (d, J=1.2 Hz, 1H), 7.36 (s, 1H), 7.97 (m, 2H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.16 (m, 2H), 3.79 (m, 1H), 3.67 (m, 2H); MS (ESI(+)) m/e 447 (M+H) + .
Example 570
propan-2-yl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate
To a suspension N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide (0.103 g, 0.249 mmol) in dichloromethane (2 ml) was added N-methylmorpholine (0.110 ml, 0.997 mmol) followed by isopropylchloroformate (0.374 ml, 0.374 mmol). A second portion of isopropylchloroformate (0.4 ml) was added and after 1 hour the mixture was directly purified by normal phase chromatography to give the title compound. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.05 (t, J=6.0 Hz, 1H), 8.51 (d, J=7.0 Hz, 1H), 7.92 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.56 (d, J=1.2 Hz, 1H), 7.40 (d, J=1.4 Hz, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.88 (dd, J=7.0, 1.7 Hz, 1H), 4.78 (hept, J=6.2 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.05 (d, J=12.9 Hz, 2H), 3.10-2.97 (m, 1H), 2.98-2.81 (m, 2H), 2.01-1.88 (m, 2H), 1.57-1.38 (m, 2H), 1.19 (d, J=6.2 Hz, 6H); MS (ESI(+)) m/e 427 (M+H) + .
Example 571
2-methylpropyl 4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}piperidine-1-carboxylate
The title compound was prepared as described in Example 570, substituting isobutyl carbonochloridate for isopropyl carbonochloridate. 1 H NMR (300 MHz, DMSO-d 6 ) δ 8.99 (t, J=6.0 Hz, 1H), 8.48 (dd, J=7.0, 0.9 Hz, 1H), 7.88 (t, J=1.0 Hz, 1H), 7.67 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.96 (d, J=3.1 Hz, 1H), 6.82 (dd, J=7.0, 1.8 Hz, 1H), 4.46 (d, J=5.8 Hz, 2H), 4.06 (d, J=13.3 Hz, 2H), 3.79 (d, J=6.6 Hz, 2H), 3.13-2.97 (m, 1H), 2.97-2.80 (m, 2H), 2.03-1.77 (m, 3H), 1.48 (qd, J=12.5, 4.2 Hz, 2H), 0.89 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 441 (M+H) + .
Example 572
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 3,3,3-trifluoropropanoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (dd, J=6.9, 1.0 Hz, 1H), 7.88 (t, J=1.0 Hz, 1H), 7.67 (d, J=3.8 Hz, 1H), 7.51 (d, J=1.3 Hz, 1H), 7.40-7.33 (m, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.46 (d, J=6.3 Hz, 2H), 3.90 (d, J=13.8 Hz, 1H), 3.66 (q, J=11.0 Hz, 2H), 3.23-3.04 (m, 2H), 2.71 (td, J=12.8, 2.6 Hz, 1H), 2.07-1.88 (m, 2H), 1.71-1.31 (m, 2H); MS (ESI(+)) m/e 451 (M+H) + .
Example 573
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]piperidin-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2-methylpropane-1-sulfonyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.9 Hz, 1H), 7.89 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.38 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.71-3.59 (m, 2H), 2.99 (tt, J=11.6, 3.6 Hz, 1H), 2.94-2.82 (m, 4H), 2.20-2.08 (m, 1H), 2.08-1.97 (m, 2H), 1.62 (qd, J=12.6, 4.1 Hz, 2H), 1.04 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 461 (M+H) + .
Example 574
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (d, J=6.8 Hz, 1H), 7.89 (s, 1H), 7.68 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.34 (m, 1H), 6.96 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.54-4.38 (m, 3H), 4.02-3.88 (m, 1H), 3.12 (tdt, J=11.3, 7.9, 3.1 Hz, 2H), 2.76-2.41 (m, 5H), 2.06-1.88 (m, 2H), 1.58 (qd, J=12.3, 4.0 Hz, 1H), 1.42 (qd, J=12.5, 4.2 Hz, 1H); MS (ESI(+)) m/e 465 (M+H) + .
Example 575
N-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide
A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(1-isobutyrylpiperidin-4-yl)benzamide (0.025 g, 0.062 mmol) in chloroform (1.030 ml) was treated with N-chlorosuccinimide (9.49 mg, 0.071 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated under a stream of warm nitrogen. The residue was purified by normal phase chromatography to give the title compound. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.67 (d, J=7.0 Hz, 1H), 8.11 (s, 1H), 7.89-7.83 (m, 2H), 7.81 (s, 1H), 7.57 (dd, J=7.1, 1.5 Hz, 1H), 7.43-7.37 (m, 2H), 4.80-4.75 (m, 2H), 4.75-4.67 (m, 1H), 4.25-4.16 (m, 1H), 3.28-3.18 (m, 1H), 3.07-2.88 (m, 2H), 2.79-2.66 (m, 1H), 2.02-1.85 (m, 2H), 1.75-1.53 (m, 2H), 1.17-1.08 (m, 6H); MS (ESI(+)) m/e 439 (M+H) + .
Example 576
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.1, 1.0 Hz, 1H), 8.13 (s, 1H), 7.89 (t, J=1.0 Hz, 1H), 7.81 (s, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.3 Hz, 1H), 7.43-7.36 (m, 1H), 7.23 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.1, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.8, 4.6 Hz, 2H), 3.52 (ddd, J=11.9, 9.1, 3.0 Hz, 2H), 1.51 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.24 (dt, J=13.4, 4.0 Hz, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 436 (M+H) + .
Example 577
5-[1-(2-cyano-2-methylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 2,2-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ 9.05 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.8, 1.0 Hz, 1H), 8.19 (d, J=0.7 Hz, 1H), 7.92 (s, 1H), 7.90-7.88 (m, 1H), 7.76 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.43-7.36 (m, 1H), 7.27 (d, J=3.8 Hz, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H), 4.35 (s, 2H), 1.35 (s, 6H); MS (ESI(+)) m/e 405 (M+H) + .
Example 578
4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
Example 578A
1-(5-bromo-4-chlorothiophen-2-yl)ethanone
2-Bromo-3-chlorothiophene (10.7 g, 51.5 mmol) was dissolved in dichloromethane (73.5 ml). The flask was equipped with a desiccant filled drying tube and the solution was chilled in an ice bath. Acetyl chloride (6.06 g, 77 mmol) was added followed by addition of aluminum trichloride (8.24 g, 61.8 mmol) over about 2 minutes (reaction bubbled vigorously as aluminum trichloride was added). The reaction mixture was stirred overnight, allowing to warm to room temperature, and then added cautiously and with stirring to a 1-L beaker containing 200 mL sat sodium bicarbonate. The mixture was stirred for 30 minutes and diluted with dichloromethane (˜100 mL). The layers were separated and the organic layer was washed with aqueous saturated sodium bicarbonate, water, and brine. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to give a crude solid. This material was recrystallized from hot hexanes to give the title compound.
Example 578B
5-bromo-4-chlorothiophene-2-carboxylic acid
Sodium hydroxide (50% in water) (5.82 ml, 110 mmol) was added to water (15 ml), and the mixture was chilled to 0° C. Bromine solution (1.669 ml, 32.6 mmol) was added, followed by dropwise addition of a solution of 1-(5-bromo-4-chlorothiophen-2-yl)ethanone (2.4 g, 10.02 mmol) in dioxane (18 ml). The mixture was stirred for 1.5 hours at room temperature, washed with dichloromethane, and then the aqueous phase was adjusted to pH 1 using 4N aqueous HCl. The precipitated solid was collected by filtration to give the title compound.
Example 578C
4-chloro-5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 51A, substituting 5-bromo-4-chlorothiophene-2-carboxylic acid for 4-bromoaniline.
Example 578D
4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-chloro-5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) ppm 9.17 (t, J=5.9 Hz, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.31 (s, 1H), 7.93-7.88 (m, 2H), 7.83 (s, 1H), 7.53 (d, J=1.1 Hz, 1H), 7.42 (s, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.98 (d, J=7.2 Hz, 2H), 2.20-2.08 (m, 1H), 0.86 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 414 (M+H) + .
Example 579
4-chloro-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(3R)-tetrahydrofuran-3-ylmethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (R)-4-chloro-5-(1-((tetrahydrofuran-3-yl)methyl)-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, DMSO-d 6 ) ppm 9.17 (t, J=6.0 Hz, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.28 (s, 1H), 7.93-7.88 (m, 2H), 7.83 (s, 1H), 7.53 (d, J=1.2 Hz, 1H), 7.42 (s, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.28-4.15 (m, 3H), 3.78-3.72 (m, 1H), 3.67-3.61 (m, 1H), 1.98-1.90 (m, 1H), 1.84-1.70 (m, 2H), 1.65-1.57 (m, 1H); MS (ESI(+)) m/e 442 (M+H) + .
Example 621
5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
Example 621A
N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 621B
5-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.88 (s, 1H), 8.48 (s, 1H), 8.04 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.72 (s, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.03 (s, 2H), 1.08 (s, 6H); MS (ESI(+)) m/e 397 (M+H) + .
Example 622
5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-(4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.88 (s, 1H), 8.48 (s, 1H), 8.04 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.72 (s, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.03 (s, 2H), 1.08 (s, 6H); MS (ESI(+)) m/e 437 (M+H) + .
Example 623
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)azetidin-3-yl]benzamide
The title compound was prepared as described in Example 557C, substituting methane sulfonyl chloride for propane-2-sulfonyl chloride. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.11 (t, J=6.0 Hz, 1H), 8.49 (m, 1H), 7.91 (m, 2H), 7.88 (m, 1H), 7.52 (m, 2H), 7.49 (m, 1H), 7.39 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.23 (m, 2H), 3.95 (m, 3H), 3.08 (s, 3H); MS (ESI(+)) m/e 385 (M+H) + .
Example 624
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(methylsulfonyl)pyrrolidin-3-yl]benzamide
The title compound was prepared as described in Example 557C, substituting methane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 3.73 (dd, J=9.6, 7.5 Hz, 1H), 3.47 (m, 2H), 3.35 (m, 1H), 3.19 (t, J=9.6 Hz, 1H), 2.97 (s, 3H), 2.31 (m, 1H), 2.02 (m, 1H); MS (ESI(+)) m/e 399 (M+H) + .
Example 625
4-[1-(ethylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 557C, substituting ethane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.52 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (s, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.75 (dd, J=9.5, 7.5 Hz, 1H), 3.50 (m, 2H), 3.38 (m, 1H), 3.26-3.12 (m, 3H), 2.32 (m, 1H), 2.03 (m, 1H), 1.24 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 413 (M+H) + .
Example 626
4-[1-(cyclopropylsulfonyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 557C, substituting cyclopropane sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.07 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.88 (m, 3H), 7.51 (d, J=1.2 Hz, 1H), 7.45 (m, 2H), 7.38 (m, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 4.50 (d, J=5.9 Hz, 2H), 3.79 (dd, J=9.7, 7.5 Hz, 1H), 3.53 (m, 2H), 3.43 (m, 1H), 3.23 (m, 1H), 2.78 (m, 1H), 2.34 (m, 1H), 2.01 (m, 1H), 0.98 (m, 4H); MS (ESI(+)) m/e 425 (M+H) + .
Example 627
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)pyrrolidin-3-yl]benzamide
The title compound was prepared as described in Example 557C, substituting benzene sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.87 (m, 3H), 7.81 (m, 2H), 7.74 (m, 1H), 7.66 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (m, 1H), 7.25 (m, 2H), 6.84 (dd, J=6.9, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.72 (dd, J=9.8, 7.5 Hz, 1H), 3.46 (m, 1H), 3.26 (m, 2H), 3.11 (m, 1H), 2.17 (m, 1H), 1.78 (m, 1H); MS (ESI(+)) m/e 461 (M+H) + .
Example 672
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)pyrrolidin-3-yl]benzamide
The title compound was prepared as described in Example 557C, substituting propane-2-sulfonyl chloride for propane-2-sulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(pyrrolidin-3-yl)benzamide for 4-(azetidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide. 1 H NMR (501 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.47 (d, J=6.9 Hz, 1H), 7.87 (m, 3H), 7.50 (d, J=1.2 Hz, 1H), 7.43 (m, 2H), 7.37 (s, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 3.77 (m, 1H), 3.52 (m, 2H), 3.42 (m, 2H), 3.25 (m, 1H), 2.30 (m, 1H), 2.04 (m, 1H), 1.25 (dd, J=6.8, 1.4 Hz, 6H); MS (ESI(+)) m/e 427 (M+H)+.
Example 673
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(2-methoxyethyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 51A, substituting 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.66 (s, 1H), 8.50 (d, J=7.0 Hz, 1H), 8.01 (s, 1H), 7.90 (s, 1H), 7.77 (s, 1H), 7.54 (s, 1H), 7.40 (m, 5H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 6.71 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H), 4.23 (t, J=5.3 Hz, 2H), 3.69 (t, J=5.3 Hz, 2H), 3.23 (s, 3H); MS (ESI(+)) m/e 391 (M+H) + .
Example 674
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 51A, substituting 1-(tetrahydrofuran-2-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline.— 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.64 (s, 1H), 8.47 (d, J=7.0 Hz, 1H), 8.00 (s, 1H), 7.87 (s, 1H), 7.77 (s, 1H), 7.50 (d, J=1.2 Hz, 1H), 7.40 (m, 5H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.33 (d, J=6.0 Hz, 2H), 4.13 (m, 3H), 3.74 (m, 1H), 3.62 (m, 1H), 1.91 (m, 1H), 1.76 (m, 2H), 1.60 (m, 1H); MS (ESI(+)) m/e 417 (M+H) + .
Example 675
1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-{4-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazol-4-yl]phenyl}urea
The title compound was prepared as described in Example 51A, substituting 1-(tetrahydro-2H-pyran-4-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1-(4-bromophenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 4-bromoaniline. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.64 (s, 1H), 8.47 (d, J=7.0 Hz, 1H), 8.02 (s, 1H), 7.87 (s, 1H), 7.77 (d, J=0.8 Hz, 1H), 7.50 (d, J=1.2 Hz, 1H), 7.40 (m, 5H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.70 (t, J=6.0 Hz, 1H), 4.32 (d, J=5.9 Hz, 2H), 3.98 (d, J=7.1 Hz, 2H), 3.81 (m, 2H), 3.23 (m, 2H), 2.05 (m, 1H), 1.40 (m, 2H), 1.23 (m, 2H); MS (ESI(+)) m/e 431 (M+H) + .
Example 676
5-[1-(1,4-dioxan-2-ylmethyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((1,4-dioxan-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromothiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.90-8.85 (m, 1H), 8.48 (s, 1H), 8.12 (s, 1H), 7.84 (dd, J=9.2, 0.8 Hz, 1H), 7.82 (d, J=0.6 Hz, 1H), 7.71 (d, J=3.9 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.8 Hz, 2H), 4.20-4.12 (m, 2H), 3.95-3.83 (m, 1H), 3.74 (dd, J=11.4, 2.5 Hz, 2H), 3.68-3.60 (m, 1H), 3.59-3.39 (m, 2H), 3.29-3.21 (m, 1H); MS (ESI(+)) m/e 425 (M+H) + .
Example 677
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (dd, J=7.0, 0.8 Hz, 1H), 7.91-7.85 (m, 1H), 7.67 (d, J=3.8 Hz, 1H), 7.55-7.35 (m, 4H), 7.34-7.25 (m, 2H), 6.98 (dd, J=3.8, 0.5 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.60 (d, J=13.2 Hz, 1H), 4.46 (d, J=5.9 Hz, 2H), 3.45 (d, J=12.7 Hz, 1H), 3.28-3.08 (m, 2H), 2.93 (td, J=12.8, 2.5 Hz, 1H), 2.00 (dd, J=43.2, 12.5 Hz, 2H), 1.68-1.39 (m, 2H); MS (ESI(+)) m/e 463 (M+H) + .
Example 678
tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.00-8.96 (m, 1H), 8.51-8.46 (m, 1H), 8.04-8.00 (m, 1H), 7.89-7.81 (m, 2H), 7.81-7.77 (m, 1H), 7.39-7.32 (m, 2H), 4.68 (s, 2H), 4.27-4.16 (m, 2H), 2.97-2.70 (m, 3H), 1.92-1.78 (m, 2H), 1.71-1.50 (m, 2H), 1.48 (s, 9H); MS (ESI(+)) m/e 436 (M+H)+.
Example 679
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.19 (d, J=0.9 Hz, 1H), 8.65 (d, J=1.2 Hz, 1H), 8.20 (d, J=1.1 Hz, 1H), 8.03 (d, J=1.5 Hz, 1H), 7.90-7.83 (m, 2H), 7.73-7.66 (m, 2H), 4.74 (s, 2H), 2.44-2.22 (m, 3H), 1.92-1.76 (m, 2H), 1.76-1.49 (m, 4H), 1.35-1.14 (m, 2H); MS (ESI(+)) m/e 378 (M+H) + .
Example 680
tert-butyl 4-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyrazin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.99-8.95 (m, 1H), 8.48-8.44 (m, 1H), 8.02 (s, 1H), 7.81-7.77 (m, 1H), 7.33-7.26 (m, 2H), 7.15-7.09 (m, 2H), 4.49 (s, 2H), 4.22-4.14 (m, 2H), 2.92-2.73 (m, 2H), 2.74-2.58 (m, 1H), 1.82-1.74 (m, 2H), 1.61-1.41 (m, 11H); MS (ESI(+)) m/e 451 (M+H) + .
Example 681
2-cyclopentyl-N-(4-{[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]amino}phenyl)acetamide
The title compound was prepared as described in Example 1C, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyrazin-6-ylmethanamine for imidazo[1,2-a]pyridin-6-amine 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.17-9.13 (m, 1H), 8.60 (s, 1H), 8.18 (s, 1H), 7.99 (d, J=1.5 Hz, 1H), 7.46-7.40 (m, 2H), 7.35-7.29 (m, 2H), 4.56 (bs, 2H), 2.37-2.23 (m, 3H), 1.90-1.77 (m, 2H), 1.77-1.49 (m, 4H), 1.34-1.17 (m, 2H); MS (ESI(+)) m/e 393 (M+H) + .
Example 682
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide
A solution of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide (0.05 g, 0.150 mmol) in tetrahydrofuran (1.246 ml) was treated with sodium hydride (0.018 g, 0.449 mmol) in 3 portions. The reaction was stirred at ambient temperature for 45 minutes and became a partially homogeneous solution. Benzenesulfonyl chloride (0.021 ml, 0.164 mmol) was added and the mixture was stirred for 16 hours. The reaction was treated with 0.1 mL water and was concentrated under a stream of nitrogen. Reverse-phase chromatography provided the title compound. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.73 (dd, J=7.0, 0.9 Hz, 1H), 8.15 (dd, J=2.2, 0.8 Hz, 1H), 7.97 (d, J=2.2 Hz, 1H), 7.89-7.75 (m, 5H), 7.73-7.59 (m, 3H), 7.46 (dd, J=7.0, 1.6 Hz, 1H), 7.37-7.31 (m, 2H), 4.75 (s, 2H), 3.96-3.88 (m, 2H), 2.67-2.52 (m, 1H), 2.48-2.37 (m, 2H), 1.95-1.72 (m, 4H); MS (ESI(+)) m/e 475 (M+H) + .
Example 683
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.17 (d, J=2.2 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 7.89-7.83 (m, 2H), 7.80 (s, 1H), 7.49 (dd, J=7.0, 1.6 Hz, 1H), 7.43-7.37 (m, 2H), 4.77 (s, 2H), 3.95-3.87 (m, 2H), 3.38-3.29 (m, 1H), 3.12-3.00 (m, 2H), 2.89-2.75 (m, 1H), 1.95-1.86 (m, 2H), 1.82-1.68 (m, 2H), 1.34 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 417 (M+H) + .
Example 684
4-[1-(cyclopropylsulfonyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide
The title compound was prepared as described in Example 682, substituting cyclopropanesulfonyl chloride for benzenesulfonyl chloride. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (dd, J=7.0, 0.9 Hz, 1H), 8.19-8.15 (m, 1H), 7.98 (d, J=2.2 Hz, 1H), 7.90-7.84 (m, 2H), 7.80 (s, 1H), 7.48 (dd, J=7.0, 1.6 Hz, 1H), 7.45-7.38 (m, 2H), 4.77 (s, 2H), 3.92-3.84 (m, 2H), 3.07-2.96 (m, 2H), 2.86-2.73 (m, 1H), 2.57-2.46 (m, 1H), 2.00-1.91 (m, 2H), 1.88-1.73 (m, 2H), 1.13-0.99 (m, 4H); MS (ESI(+)) m/e 439 (M+H) + .
Example 685
5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 685A
tert-butyl 5-formylthiophene-2-carboxylate
5-Formylthiophene-2-carboxylic acid (5.3 g, 33.9 mmol) was taken up in tetrahydrofuran (100 ml) and boc-anhydride (16.30 g, 74.7 mmol) was added, followed by N,N-dimethylaminopyridine (0.829 g, 6.79 mmol). The mixture was stirred overnight at room temperature, during which time the reaction became a dark, purplish color. It was diluted with saturated sodium bicarbonate and extracted with ether. The organic layers were dried over sodium sulfate, concentrated then purified by normal phase chromatography to give the title compound.
Example 685B
(S,E)-tert-butyl 5-(((tert-butylsulfinyl)imino)methyl)thiophene-2-carboxylate
tert-Butyl 5-formylthiophene-2-carboxylate (2 g, 9.42 mmol) and (S)-2-methylpropane-2-sulfinamide (1.370 g, 11.31 mmol) were dissolved in dichloromethane (100 ml).). The mixture was chilled in an ice bath, and then tetraethoxytitanium (8.7 ml, 41.5 mmol) was added. The mixture was allowed to warm to room temperature overnight with stirring. The mixture was poured into a large Erlenmeyer flask with 200 mL dichloromethane and was diluted with 18 mL H 2 O. After vigorous stirring for 30 minutes the suspension was filtered through diatomaceous earth and the filtrate was concentrated. Purification using normal phase chromatography provided the title compound.
Example 685C
tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate and tert-butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate
(S,E)-tert-Butyl 5-((tert-butylsulfinylimino)methyl)thiophene-2-carboxylate (1 g, 3.17 mmol) was dissolved in dichloromethane (15.85 ml) and chilled to −45° C. in an acetone bath to which dry ice had been added to achieve the desired temperature. Isobutylmagnesium bromide (2.0M in diethyl ether; 3.17 ml, 6.34 mmol) was added dropwise over 5 minutes. The mixture was stirred for 4 hours keeping the temperature between −40° C. and −50° C. by periodic addition of dry ice and then warmed to room temperature overnight. The mixture was quenched with saturated ammonium chloride (exothermic, bubbling) and extracted with dichloromethane (three times; considerable emulsion formed). The organic extracts were dried with sodium sulfate, filtered, concentrated and chromatographed to provide both tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate and tert-butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate as separate compounds.
Example 685D
(R)-tert-butyl 5-(1-amino-3-methylbutyl)thiophene-2-carboxylate
The title compound was prepared as described in Example 324C, substituting tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate.
Example 685E
(R)-5-(1-(cyclopropanecarboxamido)-3-methylbutyl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 1A, substituting (R)-tert-butyl 5-(1-amino-3-methylbutyl)thiophene-2-carboxylate for 3-methylbutan-1-amine and cyclopropanecarboxylic acid for 4-nitrobenzoic acid followed by acidic deprotection as described in Example 28A, substituting (R)-tert-butyl 5-(1-(cyclopropanecarboxamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 685F
5-{(1R)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and (R)-5-(1-(cyclopropanecarboxamido)-3-methylbutyl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.00 (t, J=6.0 Hz, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.48 (d, J=7.4 Hz, 1H), 7.88 (d, J=1.1 Hz, 1H), 7.64 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 5.11 (td, J=8.8, 5.0 Hz, 1H), 4.46 (d, J=5.9 Hz, 2H), 1.80-1.52 (m, 4H), 0.95-0.83 (m, 6H), 0.75-0.59 (m, 4H); MS (ESI(+)) m/e 411 (M+H) + .
Example 686
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{(1R)-3-methyl-1-[(tetrahydrofuran-3-ylacetyl)amino]butyl}thiophene-2-carboxamide
The title compound was described as in Example 685, substituting 2-(tetrahydrofuran-3-yl)acetic acid for cyclopropanecarboxylic acid in Example 685E. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.00 (t, J=6.0 Hz, 1H), 8.48 (d, J=7.0 Hz, 1H), 8.39 (d, J=8.5 Hz, 1H), 7.88 (s, 1H), 7.64 (d, J=3.7 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 6.97 (d, J=3.8 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 5.16-5.05 (m, 1H), 4.45 (d, J=5.9 Hz, 2H), 3.76-3.51 (m, 3H), 3.29-3.21 (m, 1H), 2.29-2.16 (m, 3H), 2.02-1.86 (m, 1H), 1.78-1.40 (m, 4H), 0.99-0.77 (m, 6H); MS (ESI(+)) m/e 455 (M+H) + .
Example 687
5-{(1S)-1-[(cyclopropylcarbonyl)amino]-3-methylbutyl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was described as in Example 685, substituting butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate for tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate in Example 685D. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.04-8.96 (m, 1H), 8.55 (d, J=8.4 Hz, 1H), 8.48 (dd, J=7.0, 0.9 Hz, 1H), 7.88 (s, 1H), 7.64 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.37 (s, 1H), 6.98 (d, J=3.8 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 5.17-5.05 (m, 1H), 4.46 (d, J=5.9 Hz, 2H), 1.77-1.44 (m, 4H), 1.01-0.77 (m, 6H), 0.66 (d, J=7.2 Hz, 4H); MS (ESI(+)) m/e 411 (M+H) + .
Example 688
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide
Example 688A
ethyl 2-(piperidin-4-yl)thiazole-5-carboxylate
Ethyl 3-ethoxyacrylate (1.50 g, 10.38 mml) was dissolved in dioxane/water and chilled to −10° C. N-Bromosuccinimide (2.03 g, 11.42 mmol) was added and the mixture was stirred 1 hour at room temperature. tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (2.54 g, 10.38 mmol) was added and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into 25 mL saturated ammonium hydroxide and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.
Example 688B
ethyl 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate
Ethyl 2-(piperidin-4-yl)thiazole-5-carboxylate (100 mg, 0.416 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (21 mg, 0.033 mmol), bis(dibenzylideneacetone)palladium(0) (15 mg, 0.017 mmol) and cesium carbonate (678 mg, 2.081 mmol) were placed in a pressure tube capped with a septum and degassed with nitrogen by passing a stream through the vessel for 30 minutes. Separately, bromobenzene (68.6 mg, 0.437 mmol) was dissolved in toluene (2 ml) and the solution was degassed by bubbling nitrogen for 30 minutes. The bromobenzene solution was added to the solid mixture and the sealed tube was heated to 100° C. overnight. The mixture was partitioned between dichloromathane and water and the combined organic layers were concentrated and purified by normal phase chromatography to give the title compound.
Example 688C
lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate
A solution of ethyl 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate (31 mg, 0.098 mmol) in 1 ml of 1:1 tetrahydrofuran/methanol was treated with 1M LiOH (0.11 ml, 0.11 mol) and stirred at 65° C. for 3 hours. The mixture was taken to dryness and used directly in the next step.
Example 688D
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide
Lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate (28.8 mg, 0.098 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (17.31 mg, 0.118 mmol), 4-methylmorpholine (49.6 mg, 0.490 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (55.9 mg, 0.147 mmol) were combined in a vial with dichloromethane (2.5 ml) and the reaction was stirred overnight. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate. The organic layers were dried with sodium sulfate, filtered, and concentrated. Trituration of the crude material with dichloromethane provided the title compound. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.34 (s, 1H), 7.91-7.88 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.43-7.38 (m, 1H), 7.26-7.16 (m, 2H), 7.01-6.93 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.81-6.72 (m, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.81-3.73 (m, 2H), 3.24-3.01 (m, 1H), 2.90-2.78 (m, 2H), 2.19-2.09 (m, 2H), 1.90-1.73 (m, 2H); MS (ESI(+)) m/e 418 (M+H) + .
Example 697
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(pyridin-2-yl)piperidin-4-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 688, substituting 2-bromopyridine for bromobenzene in Example 688B. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 8.13-8.09 (m, 1H), 7.89 (s, 1H), 7.55-7.48 (m, 2H), 7.40 (s, 1H), 6.86 (d, J=8.7 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.61 (dd, J=6.9, 5.1 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.40-4.32 (m, 2H), 3.03-2.92 (m, 2H), 2.14-2.05 (m, 2H), 1.68 (qd, J=12.5, 3.9 Hz, 2H); MS (ESI(+)) m/e 419 (M+H) + .
Example 698
5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=6.0 Hz, 1H), 8.49 (d, J=7.1 Hz, 1H), 8.11 (s, 1H), 7.89 (s, 1H), 7.85 (s, 1H), 7.75 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.26 (d, J=3.9 Hz, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.42 (d, J=21.4 Hz, 2H), 3.74 (ddd, J=11.4, 4.6, 2.9 Hz, 2H), 3.51 (td, J=11.3, 2.0 Hz, 2H), 1.92-1.64 (m, 2H), 1.55 (t, J=11.8 Hz, 2H); MS (ESI(+)) m/e 440 (M+H) + .
Example 734
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide
Example 734A
5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-bromofuran-2-carboxylic acid for 4-nitrobenzoic acid.
Example 734B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and bromide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.89 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.13 (d, J=0.5 Hz, 1H), 7.91-7.86 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.67 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 4.07 (s, 2H), 3.68 (dt, J=11.5, 4.5 Hz, 2H), 3.51 (ddd, J=11.9, 9.3, 3.0 Hz, 2H), 1.51 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.33-1.15 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 420 (M+H) + .
Example 735
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
Example 735A
tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
Example 735B
tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 735C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)furan-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 735D
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.85 (t, J=6.1 Hz, 1H), 8.47 (dd, J=7.0, 0.8 Hz, 1H), 7.92-7.83 (m, 1H), 7.55-7.45 (m, 2H), 7.41 (td, J=7.5, 1.5 Hz, 1H), 7.37 (s, 1H), 7.34-7.25 (m, 2H), 7.06 (d, J=3.4 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.33 (dd, J=3.5, 0.7 Hz, 1H), 4.53 (d, J=13.4 Hz, 1H), 4.44 (d, J=6.0 Hz, 2H), 3.44 (d, J=13.0 Hz, 1H), 3.19 (t, J=12.8 Hz, 1H), 3.11-2.90 (m, 2H), 2.09 (d, J=11.0 Hz, 1H), 1.94 (d, J=11.9 Hz, 1H), 1.73-1.42 (m, 2H); MS (ESI(+)) m/e 447 (M+H) + .
Example 736
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(piperidin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.84 (t, J=6.1 Hz, 1H), 8.47 (dd, J=7.0, 0.8 Hz, 1H), 7.94-7.82 (m, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.42-7.33 (m, 1H), 7.05 (d, J=3.4 Hz, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 6.31 (dd, J=3.4, 0.6 Hz, 1H), 4.44 (d, J=6.0 Hz, 3H), 4.06-3.90 (m, 1H), 3.21-3.07 (m, 1H), 3.07-2.77 (m, 2H), 2.77-2.59 (m, 1H), 2.06-1.90 (m, 2H), 1.61-1.37 (m, 2H), 0.99 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 395 (M+H)+.
Example 738
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.33 (s, 1H), 8.13-8.09 (m, 1H), 7.89 (s, 1H), 7.55-7.48 (m, 2H), 7.40 (s, 1H), 6.86 (d, J=8.7 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.61 (dd, J=6.9, 5.1 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.40-4.32 (m, 2H), 3.03-2.92 (m, 2H), 2.14-2.05 (m, 2H), 1.68 (qd, J=12.5, 3.9 Hz, 2H); MS (ESI(+)) m/e 390 (M+H) + .
Example 739
2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}acetamide
The title compound was prepared as described in Example 1A, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 8.75 (dd, J=6.9, 1.0 Hz, 1H), 8.21-8.16 (m, 1H), 8.01 (d, J=2.1 Hz, 1H), 7.89 (s, 1H), 7.55-7.45 (m, 5H), 3.99 (s, 2H), 2.39-2.24 (m, 3H), 1.91-1.76 (m, 2H), 1.78-1.46 (m, 4H), 1.39-1.15 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 740
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.88 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.15 (s, 1H), 7.90-7.86 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.65 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 3.95 (d, J=7.2 Hz, 2H), 2.21-2.05 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 364 (M+H) + .
Example 741
5-(1-benzyl-1H-pyrazol-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.92 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.27 (d, J=0.7 Hz, 1H), 7.93 (d, J=0.7 Hz, 1H), 7.89 (t, J=0.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41-7.23 (m, 6H), 7.17 (d, J=3.5 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 5.39 (s, 2H), 4.49 (d, J=6.1 Hz, 2H); MS (ESI(+)) m/e 398 (M+H) + .
Example 742
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(25)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting (S)-1-((tetrahydrofuran-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.94 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.15 (s, 1H), 7.89 (s, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 4.28-4.09 (m, 3H), 3.78-3.69 (m, 1H), 3.68-3.55 (m, 1H), 2.01-1.88 (m, 1H), 1.85-1.66 (m, 2H), 1.66-1.54 (m, 1H); MS (ESI(+)) m/e 392 (M+H) + .
Example 743
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-pyrazol-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting (R)-1-((tetrahydrofuran-2-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.94 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.15 (s, 1H), 7.89 (s, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 6.68 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.1 Hz, 2H), 4.28-4.07 (m, 3H), 3.78-3.69 (m, 1H), 3.68-3.59 (m, 1H), 2.01-1.88 (m, 1H), 1.85-1.66 (m, 2H), 1.66-1.54 (m, 1H); MS (ESI(+)) m/e 392 (M+H) + .
Example 744
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide
Example 744A
tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
Example 744B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carb oxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)furan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 744C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.00 (t, J=5.3 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.58 (d, J=3.0 Hz, 1H), 6.53 (s, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.25 (s, 1H), 4.13 (s, 1H), 3.66 (dd, J=12.2, 6.1 Hz, 2H), 3.01-2.82 (m, 1H), 2.47 (bs, 1H), 2.36 (bs, 1H), 1.09-0.86 (m, 6H); MS (ESI(+)) m/e 393 (M+H) + .
Example 745
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.00 (dd, J=8.8, 5.7 Hz, 1H), 8.49 (dd, J=7.0, 0.5 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (dd, J=3.4, 2.1 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.58 (dd, J=6.2, 3.5 Hz, 1H), 6.52 (d, J=15.2 Hz, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.17 (dd, J=21.3, 2.5 Hz, 2H), 3.74-3.53 (m, 2H), 2.45 (bs, 1H), 2.37 (bs, 1H), 2.27 (d, J=7.0 Hz, 1H), 2.22 (d, J=6.9 Hz, 1H), 2.06-1.94 (m, 1H), 0.91 (dd, J=6.5, 5.3 Hz, 6H); MS (ESI(+)) m/e 407 (M+H) + .
Example 746
5-(1-benzoyl-1,2,3,6-tetrahydropyridin-4-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.62 (t, J=5.4 Hz, 1H), 8.44-8.39 (m, 1H), 7.81 (s, 1H), 7.51-7.35 (m, 7H), 7.08 (d, J=3.5 Hz, 1H), 6.82 (dd, J=7.0, 1.6 Hz, 1H), 6.53 (d, J=3.5 Hz, 1H), 6.50-6.43 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.20 (d, J=2.1 Hz, 2H), 3.64 (t, J=5.3 Hz, 2H), 2.52-2.46 (m, 2H); MS (ESI(+)) m/e 427 (M+H) + .
Example 747
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[4-(2-methylpropyl)phenyl]furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 4-isobutylphenylboronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.08 (t, J=6.1 Hz, 1H), 8.49 (dd, J=6.9, 0.8 Hz, 1H), 7.92-7.87 (m, 1H), 7.87-7.79 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.45-7.38 (m, 1H), 7.25 (d, J=8.3 Hz, 2H), 7.21 (d, J=3.6 Hz, 1H), 7.04 (d, J=3.6 Hz, 1H), 6.87 (dd, J=7.0, 1.7 Hz, 1H), 4.51 (d, J=6.0 Hz, 2H), 2.49-2.46 (m, 2H), 1.86 (dp, J=13.4, 6.8 Hz, 1H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 374 (M+H) + .
Example 748
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2S)-2-methylbutanoyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and (2S)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.00 (t, J=5.0 Hz, 1H), 8.49 (dd, J=7.0, 0.6 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.1 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 6.61-6.56 (m, 1H), 6.53 (d, J=9.8 Hz, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.35-4.07 (m, 2H), 3.75-3.58 (m, 2H), 2.90-2.62 (m, 1H), 2.48-2.30 (m, 2H), 1.57 (dt, J=24.3, 8.8 Hz, 1H), 1.32 (dt, J=13.1, 6.8 Hz, 1H), 0.99 (dd, J=9.6, 6.8 Hz, 3H), 0.81 (q, J=7.1 Hz, 3H); MS (ESI(+)) m/e 407 (M+H) + .
Example 749
5-[1-(3,3-dimethylbutanoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 3,3-dimethylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.00 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (t, J=3.4 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.57 (dd, J=6.1, 3.6 Hz, 1H), 6.51 (d, J=23.1 Hz, 1H), 4.47 (d, J=6.0 Hz, 2H), 4.19 (dd, J=31.4, 2.4 Hz, 2H), 3.73-3.62 (m, 2H), 2.41 (d, J=31.8 Hz, 2H), 2.28 (d, J=17.4 Hz, 2H), 0.99 (d, J=7.2 Hz, 9H); MS (ESI(+)) m/e 421 (M+H) + .
Example 750
5-[1-(cyclopropylacetyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and cyclopropylacetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.05-8.93 (m, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 7.90-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (bs, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 6.58 (dd, J=6.9, 3.5 Hz, 1H), 6.55-6.48 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.15 (d, J=8.4 Hz, 2H), 3.63 (dt, J=18.3, 5.7 Hz, 2H), 2.48-2.35 (m, 2H), 2.35-2.27 (m, 2H), 1.03-0.91 (m, 1H), 0.49-0.41 (m, 2H), 0.12 (dq, J=10.2, 5.0 Hz, 2H); MS (ESI(+)) m/e 405 (M+H) + .
Example 751
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide
Example 751A
tert-butyl 3-(5-formylthiazol-2-yl)pyrrolidine-1-carboxylate
tert-Butyl 3-carbamothioylpyrrolidine-1-carboxylate (5 g, 21.71 mmol), 2-chloromalonaldehyde (3.70 g, 34.7 mmol) and magnesium carbonate (1.830 g, 21.71 mmol) were combined in dioxane (100 ml). The mixture was heated to 60° C. for 3 hours, stirred overnight at room temperature and then filtered through a pad of diatomaceous earth, rinsing with dichloromethane. The filtrate was concentrated in vacuo and then purified by normal phase chromatography to provide the title compound.
Example 751B
2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)thiazole-5-carboxylic acid
tert-Butyl 3-(5-formylthiazol-2-yl)pyrrolidine-1-carboxylate (3.65 g, 12.93 mmol) was suspended in water (35 ml) and t-butanol (60 ml). Sodium dihydrogenphosphate (2.094 g, 17.45 mmol) was added, followed by 2-methylbut-2-ene (5.34 ml, 50.4 mmol). After 5 minutes, sodium chlorite (2.92 g, 32.3 mmol) was added in portions over about 5 minutes (mildly exothermic). The reaction was stirred for 1 hour at room temperature, then additional 2-methyl-2-butene (2 mL) was added. After stirring for 2 hours at room temperature, the reaction was concentrated and water (100 mL) was added. The mixture was adjusted to pH 2 by addition of 1N hydrochloric acid, then extracted dichloromethane. The organic extracts were dried over sodium sulfate, filtered and concentrated to provide the title compound.
Example 751C
tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)pyrrolidine-1-carboxylate
The title compound was prepared as described in Example 688D, substituting 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)thiazole-5-carboxylic acid for lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
Example 751D
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 3-(5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiazol-2-yl)pyrrolidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 751E
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-{1-[(2-methylpropyl)sulfonyl]pyrrolidin-3-yl}-1,3-thiazole-5-carboxamide
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide, 2.7-trifluoroacetic acid (150 mg, 0.236 mmol) was dissolved in N,N-dimethylformamide (0.7 mL). Triethylamine (0.3 mL, 2.152 mmol) was added, followed by 2-methylpropane-1-sulfonyl chloride (74.0 mg, 0.472 mmol) and the reaction was stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered, and concentrated and purified by normal phase chromatography to give the title compound. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.24 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.35 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.91 (p, J=7.2 Hz, 1H), 3.74 (dd, J=9.8, 7.3 Hz, 1H), 3.51-3.35 (m, 3H), 2.99 (d, J=6.6 Hz, 2H), 2.46-2.33 (m, 1H), 2.24-2.03 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 448 (M+H) + .
Example 752
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(phenylsulfonyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.20 (t, J=5.9 Hz, 1H), 8.50 (dd, J=7.0, 0.9 Hz, 1H), 8.21 (s, 1H), 7.89 (t, J=0.9 Hz, 1H), 7.84-7.77 (m, 2H), 7.74-7.65 (m, 1H), 7.65-7.57 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (bs, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 3.80-3.59 (m, 2H), 3.44-3.31 (m, 3H), 2.32-2.17 (m, 1H), 2.06-1.93 (m, 1H); MS (ESI(+)) m/e 468 (M+H) + .
Example 753
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(2-methylpropyl)sulfonyl]-1,2,3,6-tetrahydropyridin-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 682, substituting 2-methylpropane sulfonyl chloride for benzenesulfonyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.04-8.96 (m, 1H), 8.48 (dd, J=6.9, 0.9 Hz, 1H), 7.89-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.13 (d, J=3.5 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.62-6.57 (m, 1H), 6.56-6.51 (m, 1H), 4.47 (d, J=6.1 Hz, 2H), 3.97-3.91 (m, 2H), 3.40 (t, J=5.7 Hz, 2H), 2.97 (d, J=6.5 Hz, 2H), 2.54-2.48 (m, 2H), 2.19-2.05 (m, 1H), 1.07-1.01 (m, 6H); MS (ESI(+)) m/e 443 (M+H) + .
Example 754
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.10-9.01 (m, 2H), 8.53 (d, J=1.3 Hz, 1H), 8.18-8.16 (m, 1H), 8.14 (d, J=0.5 Hz, 1H), 7.83-7.79 (m, 2H), 7.76 (d, J=3.9 Hz, 1H), 7.22 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.13 (dp, J=13.6, 6.7 Hz, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 381 (M+H) + .
Example 755
tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 8.13 (s, 1H), 7.91-7.86 (m, 1H), 7.81 (d, J=0.4 Hz, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.23 (d, J=3.8 Hz, 1H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.8 Hz, 2H), 4.02 (s, 2H), 3.65-3.50 (m, 2H), 3.19-3.02 (m, 2H), 1.47-1.34 (m, 11H), 1.30-1.15 (m, 2H), 0.93 (s, 3H); MS (ESI(+)) m/e 535 (M+H) + .
Example 789
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 14.80 (s, 1H), 9.65 (t, J=6.0 Hz, 1H), 9.20 (s, 1H), 8.99 (s, 1H), 8.91 (d, J=7.0 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 8.21 (s, 1H), 8.17 (d, J=2.1 Hz, 1H), 7.96 (d, J=3.9 Hz, 1H), 7.86 (s, 1H), 7.84 (s, 1H), 7.51 (dd, J=7.0, 1.4 Hz, 1H), 7.28 (d, J=3.8 Hz, 1H), 4.64 (d, J=5.8 Hz, 2H), 4.10 (s, 2H), 3.19-3.12 (m, 2H), 3.04-2.96 (m, 2H), 1.74-1.59 (m, 2H), 1.57-1.46 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 435 (M+H) + .
Example 790
5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 8.97 (t, J=6.1 Hz, 1H), 8.50 (dd, J=13.4, 3.5 Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 7.92 (s, 1H), 7.56 (d, J=1.1 Hz, 1H), 7.43 (s, 1H), 7.18 (d, J=3.5 Hz, 1H), 6.89 (dd, J=7.0, 1.5 Hz, 1H), 6.71 (d, J=6.4 Hz, 1H), 4.51 (d, J=6.1 Hz, 2H), 4.46 (d, J=21.9 Hz, 2H), 3.81-3.70 (m, 2H), 3.56-3.45 (m, 2H), 1.89-1.68 (m, 2H), 1.53 (t, J=11.7 Hz, 2H); MS (ESI(+)) m/e 424 (M+H) + .
Example 801
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(phenylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.97 (t, J=6.1 Hz, 1H), 8.47 (d, J=6.5 Hz, 1H), 7.88 (s, 1H), 7.85-7.78 (m, 2H), 7.75-7.68 (m, 1H), 7.69-7.60 (m, 2H), 7.51 (d, J=1.2 Hz, 1H), 7.37 (s, 1H), 7.10 (d, J=3.5 Hz, 1H), 6.82 (dd, J=7.0, 1.7 Hz, 1H), 6.54 (d, J=3.5 Hz, 1H), 6.46-6.43 (m, 1H), 4.46 (d, J=6.1 Hz, 2H), 3.79-3.74 (m, 2H), 3.28-3.21 (m, 2H), 2.45 (s, 2H); MS (ESI(+)) m/e 463 (M+H) + .
Example 802
2-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(piperidin-4-yl)thiazole-5-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 9.23 (t, J=5.9 Hz, 1H), 8.49 (d, J=6.9 Hz, 1H), 8.34 (s, 1H), 7.89 (s, 1H), 7.56-7.36 (m, 4H), 7.35-7.25 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 4.61-4.52 (m, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.51-3.39 (m, 1H), 3.42-3.34 (m, 1H), 3.23 (t, J=12.1 Hz, 1H), 3.01 (td, J=12.7, 2.9 Hz, 1H), 2.21-2.13 (m, 1H), 2.08-1.97 (m, 1H), 1.77-1.54 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 803
5-[1-(2-fluorobenzoyl)-1,2,3,6-tetrahydropyridin-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)furan-2-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.66-8.58 (m, 1H), 8.45-8.39 (m, 1H), 7.81 (s, 1H), 7.54-7.44 (m, 2H), 7.43-7.36 (m, 2H), 7.31-7.21 (m, 2H), 7.08 (d, J=3.5 Hz, 1H), 6.82 (dd, J=6.9, 1.7 Hz, 1H), 6.53 (d, J=3.4 Hz, 1H), 6.48 (bs, 1H), 4.47 (d, J=6.1 Hz, 2H), 4.41-3.34 (m, 4H), 2.52-2.37 (m, 2H); MS (ESI(+)) m/e 445 (M+H) + .
Example 804
2-[1-(2-fluorobenzoyl)pyrrolidin-3-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.95-8.88 (m, 1H), 8.43 (d, J=7.0 Hz, 1H), 8.32-8.17 (m, 1H), 7.82 (s, 1H), 7.53-7.35 (m, 4H), 7.30-7.19 (m, 2H), 6.85-6.78 (m, 1H), 4.50-4.44 (m, 2H), 4.05-3.23 (m, 5H), 2.45-2.11 (m, 2H); MS (ESI(+)) m/e 450 (M+H) + .
Example 805
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(2-methylpropanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.28-9.19 (m, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.91-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.11-3.33 (m, 5H), 3.17 (d, J=5.2 Hz, 1H), 2.74-2.59 (m, 1H), 2.46-2.00 (m, 6H), 1.03-0.97 (m, 1H); MS (ESI(+)) m/e 398 (M+H) + .
Example 806
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-[1-(3-methylbutanoyl)pyrrolidin-3-yl]-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.28-9.19 (m, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.91-7.87 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.43-7.38 (m, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.97-3.72 (m, 2H), 3.70-3.46 (m, 2H), 3.17 (d, J=5.1 Hz, 1H), 2.45-1.91 (m, 5H), 0.94-0.86 (m, 6H); MS (ESI(+)) m/e 412 (M+H) + .
Example 807
2-(1-benzoylpyrrolidin-3-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)-1,3-thiazole-5-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) ppm 8.94-8.87 (m, 1H), 8.43 (d, J=6.9 Hz, 1H), 8.27 (s, 1H), 8.23-8.16 (m, 1H), 7.82 (s, 1H), 7.52-7.38 (m, 6H), 6.81 (dd, J=6.9, 1.7 Hz, 1H), 4.47 (d, J=5.8 Hz, 2H), 3.94-3.84 (m, 2H), 3.76-3.53 (m, 3H), 2.44-2.34 (m, 1H), 2.24-2.14 (m, 1H); MS (ESI(+)) m/e 432 (M+H) + .
Example 808
tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate
Example 808A
tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.500 g, 2.58 mmol), tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (0.593 g, 2.58 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.746 g, 3.09 mmol) were stirred together in toluene (10 ml) at 85° C. overnight. The reaction was concentrated and purified by normal phase chromatography to give the title compound.
Example 808B
tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=6.0 Hz, 1H), 8.53-8.45 (m, 1H), 8.16 (s, 1H), 7.89 (d, J=0.7 Hz, 1H), 7.79 (d, J=0.5 Hz, 1H), 7.74 (d, J=3.8 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.22 (d, J=3.9 Hz, 1H), 6.84 (dd, J=7.0, 1.6 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 4.23 (t, J=6.5 Hz, 2H), 3.29-3.25 (m, 2H), 2.74 (t, J=6.6 Hz, 2H), 2.42-2.33 (m, 4H), 1.38 (s, 9H); MS (ESI(+)) m/e 536 (M+H) + .
Example 809
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-[2-(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)ethyl]piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.34 (t, J=5.9 Hz, 1H), 8.94 (s, 2H), 8.87 (d, J=7.0 Hz, 1H), 8.33 (dd, J=2.1, 0.7 Hz, 1H), 8.22 (d, J=0.8 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 7.87 (d, J=0.8 Hz, 1H), 7.82 (d, J=3.9 Hz, 1H), 7.79 (s, 1H), 7.47 (dd, J=7.0, 1.5 Hz, 1H), 7.27 (d, J=3.8 Hz, 1H), 4.65 (d, J=5.9 Hz, 2H), 4.43-4.34 (m, 2H), 3.22-3.16 (m, 6H), 2.98-2.89 (m, 4H); MS (ESI(+)) m/e 436 (M+H) + .
Example 810
5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide
Example 810A
N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromofuran-2-carboxamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromofuran-2-carboxylic acid for 4-nitrobenzoic acid.
Example 810B
5-{1-[(4-fluorotetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-fluorotetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromofuran-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.93 (t, J=6.0 Hz, 1H), 8.90-8.85 (m, 1H), 8.48 (s, 1H), 8.13 (s, 1H), 7.92 (d, J=0.5 Hz, 1H), 7.84 (dd, J=9.2, 0.7 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.16 (d, J=3.6 Hz, 1H), 6.70 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 4.45 (d, J=21.8 Hz, 2H), 3.82-3.66 (m, 2H), 3.51 (td, J=11.2, 2.0 Hz, 2H), 1.92-1.63 (m, 2H), 1.60-1.42 (m, 2H); MS (ESI(+)) m/e 425 (M+H) + .
Example 811
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide
Example 811A
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 811B
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(2-methylpropanoyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.24 (s, 1H), 8.72-8.68 (m, 1H), 8.27-8.23 (m, 1H), 8.11-8.07 (m, 1H), 7.88-7.82 (m, 2H), 7.41-7.35 (m, 2H), 4.76 (s, 2H), 4.75-4.66 (m, 1H), 4.24-4.15 (m, 1H), 3.29-3.18 (m, 1H), 3.06-2.85 (m, 2H), 2.78-2.64 (m, 1H), 2.02-1.84 (m, 2H), 1.74-1.52 (m, 2H), 1.17-1.07 (m, 6H); MS (ESI(+)) m/e 406 (M+H) + .
Example 812
4-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 4-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.29-9.25 (m, 1H), 8.72 (d, J=1.4 Hz, 1H), 8.27 (d, J=1.7 Hz, 1H), 8.12 (d, J=1.7 Hz, 1H), 7.89-7.83 (m, 2H), 7.55-7.45 (m, 2H), 7.44-7.38 (m, 2H), 7.25-7.16 (m, 2H), 4.87-4.84 (m, 1H), 4.77 (s, 2H), 3.90-3.79 (m, 1H), 3.33-3.19 (m, 1H), 3.03-2.89 (m, 2H), 2.07-1.61 (m, 4H); MS (ESI(+)) m/e 458 (M+H) + .
Example 813
4-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2,5-difluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.23 (s, 1H), 8.69 (s, 1H), 8.24 (d, J=1.6 Hz, 1H), 8.07 (d, J=1.6 Hz, 1H), 7.89-7.83 (m, 2H), 7.43-7.36 (m, 2H), 7.31-7.15 (m, 3H), 4.84-4.73 (m, 3H), 3.71-3.62 (m, 1H), 3.36-3.24 (m, 1H), 3.04-2.90 (m, 2H), 2.04-1.95 (m, 1H), 1.92-1.61 (m, 3H); MS (ESI(+)) m/e 476 (M+H) + .
Example 814
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 1-methylcyclopropanecarboxylic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.28 (s, 1H), 8.73 (s, 1H), 8.28 (d, J=1.7 Hz, 1H), 8.13 (d, J=1.7 Hz, 1H), 7.89-7.83 (m, 2H), 7.42-7.36 (m, 2H), 4.78 (s, 2H), 4.62-4.53 (m, 2H), 3.20-2.70 (m, 3H), 1.97-1.89 (m, 2H), 1.72-1.57 (m, 2H), 1.33 (s, 3H), 0.96-0.89 (m, 2H), 0.71-0.58 (m, 2H); MS (ESI(+)) m/e 418 (M+H) + .
Example 815
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.22 (d, J=1.4 Hz, 1H), 8.68 (d, J=1.4 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 7.89-7.82 (m, 2H), 7.42-7.34 (m, 2H), 4.81-4.65 (m, 3H), 4.11-3.99 (m, 1H), 3.62-3.44 (m, 2H), 3.37-3.21 (m, 1H), 3.01-2.86 (m, 1H), 2.85-2.71 (m, 1H), 1.99-1.85 (m, 2H), 1.85-1.54 (m, 2H); MS (ESI(+)) m/e 446 (M+H) + .
Example 816
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(3-methylbutanoyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 99.24 (d, J=1.4 Hz, 1H), 8.70 (d, J=1.4 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.09 (d, J=1.7 Hz, 1H), 7.89-7.82 (m, 2H), 7.41-7.34 (m, 2H), 4.79-4.66 (m, 3H), 4.19-4.07 (m, 1H), 3.30-3.16 (m, 1H), 3.00-2.85 (m, 1H), 2.80-2.63 (m, 1H), 2.36-2.29 (m, 2H), 2.17-2.00 (m, 1H), 2.01-1.84 (m, 2H), 1.75-1.50 (m, 2H), 0.99 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 420 (M+H) + .
Example 817
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(propan-2-ylsulfonyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (500 MHz, methanol-d 4 ) δ ppm 9.21 (d, J=1.4 Hz, 1H), 8.67 (d, J=1.4 Hz, 1H), 8.22 (d, J=1.6 Hz, 1H), 8.05 (d, J=1.6 Hz, 1H), 7.89-7.82 (m, 2H), 7.40-7.35 (m, 2H), 4.85-4.79 (m, 1H), 4.75 (s, 2H), 3.96-3.85 (m, 2H), 3.12-3.00 (m, 2H), 2.88-2.74 (m, 1H), 1.95-1.85 (m, 2H), 1.84-1.65 (m, 2H), 1.33 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 442 (M+H) + .
Example 818
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.7 Hz, 1H), 7.89 (s, 1H), 7.54-7.51 (m, 2H), 7.41 (s, 1H), 7.30 (d, J=3.6 Hz, 1H), 6.96 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.6 Hz, 1H), 6.76 (d, J=1.9 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.22 (d, J=7.3 Hz, 2H), 2.04 (dp, J=13.8, 6.8 Hz, 1H), 0.81 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 364 (M+H) + .
Example 819
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide
Example 819A
5-(1-isobutyl-1H-pyrazol-4-yl)furan-2-carboxylic acid
The title compound was prepared as described in Example 51A, substituting 5-bromofuran-2-carboxylic acid for 4-bromoaniline.
Example 819B
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)furan-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.05-9.02 (m, 1H), 8.90 (t, J=6.0 Hz, 1H), 8.52 (d, J=1.4 Hz, 1H), 8.19-8.14 (m, 2H), 7.90-7.88 (m, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.17 (d, J=3.5 Hz, 1H), 6.65 (d, J=3.5 Hz, 1H), 4.56 (d, J=5.9 Hz, 2H), 3.96 (d, J=7.1 Hz, 2H), 2.20-2.07 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 365 (M+H) + .
Example 820
5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)furan-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 8.94-8.85 (m, 2H), 8.48 (s, 1H), 8.14 (s, 1H), 7.87 (s, 1H), 7.84 (d, J=9.1 Hz, 1H), 7.66 (dd, J=9.1, 1.7 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 6.64 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 3.95 (d, J=7.1 Hz, 2H), 2.21-1.97 (m, 1H), 0.90-0.76 (m, 6H); MS (ESI(+)) m/e 365 (M+H) + .
Example 821
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(3-methylbutyl)-1H-pyrazol-5-yl]furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-isopentyl-1H-pyrazol-5-ylboronic acid for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.8 Hz, 1H), 7.89 (s, 1H), 7.58-7.43 (m, 2H), 7.43-7.37 (m, 1H), 7.30 (d, J=3.5 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.73 (d, J=1.9 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 4.44-4.36 (m, 2H), 1.68-1.38 (m, 3H), 0.84 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 378 (M+H) + .
Example 822
5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-bromofuran-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.95-8.83 (m, 2H), 8.48 (s, 1H), 8.15-8.09 (m, 1H), 7.88 (d, J=0.4 Hz, 1H), 7.83 (dd, J=9.2, 0.7 Hz, 1H), 7.66 (dd, J=9.2, 1.7 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 6.66 (d, J=3.5 Hz, 1H), 4.56 (d, J=6.0 Hz, 2H), 4.06 (s, 2H), 3.68 (dt, J=11.4, 4.5 Hz, 2H), 3.51 (ddd, J=11.9, 9.3, 2.9 Hz, 2H), 1.50 (ddd, J=13.4, 9.2, 4.2 Hz, 2H), 1.31-1.17 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 421 (M+H) + .
Example 823
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide
Example 823A
Methyl 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate
The title compound was prepared as described in Example 688D, substituting 5-(methoxycarbonyl)thiophene-2-carboxylic acid for lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
Example 823B
Lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate
The title compound was prepared as described in Example 688C, substituting methyl 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for ethyl 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate.
Example 823C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting), (R)-2-(methoxymethyl)pyrrolidine for 3-methylbutan-1-amine and lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=4.0 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.39 (m, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.35-4.23 (m, 1H), 3.78-3.65 (m, 2H), 3.26 (s, 3H), 2.02-1.81 (m, 4H); MS (ESI(+)) m/e 399 (M+H) + .
Example 824
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting), 2-isobutylpyrrolidine for 3-methylbutan-1-amine and lithium 5-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)thiophene-2-carboxylate for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) ppm 9.23 (t, J=6.0 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=4.0 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.39 (m, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 4.49 (d, J=5.9 Hz, 2H), 4.35-4.23 (m, 1H), 3.78-3.65 (m, 2H), 3.26 (s, 3H), 2.02-1.81 (m, 4H); MS (ESI(+)) m/e 411 (M+H) + .
Example 825
5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.89 (t, J=6.1 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.11 (d, J=0.5 Hz, 1H), 7.95-7.83 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.46-7.34 (m, 1H), 7.17 (d, J=3.4 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.66 (d, J=3.5 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 3.95 (s, 2H), 0.92 (s, 9H); MS (ESI(+)) m/e 378 (M+H) + .
Example 826
4-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.08-9.00 (m, 2H), 8.49 (d, J=1.4 Hz, 1H), 8.16-8.13 (m, 1H), 7.92-7.85 (m, 2H), 7.79 (d, J=1.0 Hz, 1H), 7.57-7.23 (m, 6H), 4.74-4.61 (m, 1H), 4.57 (d, J=5.7 Hz, 2H), 3.54-3.43 (m, 1H), 3.24-3.14 (m, 1H), 3.00-2.79 (m, 2H), 1.97-1.84 (m, 1H), 1.82-1.47 (m, 3H); MS (ESI(+)) m/e 458 (M+H) + .
Example 827
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
Example 827A
tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and ethyl 5-bromothiophene-2-carboxylate for 4-bromoaniline.
Example 827B
tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 827C
5-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiophene-2-carboxylic acid
In a 250 mL round bottom flask was mixed tert-butyl 4-(5-(ethoxycarbonyl)thiophen-2-yl)piperidine-1-carboxylate (5.00 g, 14.73 mmol) in tetrahydrofuran (50 ml). Aqueous 4N NaOH (38.41 ml, 73.6 mmol) solution was added along with some methanol (10 ml) to get a single phase solution. The mixture was stirred overnight at room temperature. The solvents were removed to give a white slurry that was diluted with water and adjusted to pH of 5 with 1N aqueous hydrochloric acid. Filtration provided the title compound.
Example 827D
tert-butyl 4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 827E
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 827F
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.05 (m, 2H), 8.50 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.7 Hz, 1H), 7.50 (m, 1H), 7.43 (m, 1H), 7.31 (m, 2H), 6.98 (d, J=3.8 Hz, 1H), 4.60 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.45 (m, 1H), 3.18 (m, 2H), 2.93 (m, 1H), 2.12-1.85 (m, 2H), 1.52 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 828
5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 4-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.05 (m, 2H), 8.51 (d, J=1.4 Hz, 1H), 8.16 (t, J=0.8 Hz, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.70 (d, J=3.8 Hz, 1H), 7.49 (m, 2H), 7.28 (m, 2H), 6.99 (dd, J=3.7, 0.8 Hz, 1H), 4.54 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.65 (m, 1H), 3.15 (m, 2H), 2.93 (m, 1H), 1.97 (m, 2H), 1.59 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 829
5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2,4-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.05 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 7.52 (m, 1H), 7.37 (td, J=9.7, 2.4 Hz, 1H), 7.19 (td, J=8.5, 2.5 Hz, 1H), 6.98 (d, J=3.8 Hz, 1H), 4.58 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.43 (m, 1H), 3.17 (m, 2H), 2.92 (m, 1H), 2.00 (m, 2H), 1.52 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 830
5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.04 (m, 2H), 8.51 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.1 Hz, 1H), 7.70 (d, J=3.8 Hz, 1H), 7.56 (m, 1H), 7.36 (m, 2H), 6.98 (d, J=3.8 Hz, 1H), 4.57 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.02 (m, 2H), 1.55 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 831
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
Example 831A
tert-butyl 4-(5-(([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 831B
N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(5-(([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)carbamoyl)thiophen-2-yl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 831C
5-[1-(2-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.50 (m, 1H), 7.42 (m, 1H), 7.31 (m, 2H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.60 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.45 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.54 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 832
5-[1-(3-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 3-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.66 (m, 2H), 7.50 (m, 1H), 7.34-7.22 (m, 3H), 6.98 (d, J=3.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.56 (m, 1H), 3.13 (m, 2H), 2.91 (m, 1H), 1.97 (m, 2H), 1.60 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 833
5-[1-(4-fluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 4-fluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.47 (m, 2H), 7.27 (m, 2H), 6.98 (dd, J=3.7, 0.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.62 (m, 1H), 3.14 (m, 2H), 2.91 (m, 1H), 1.97 (m, 2H), 1.58 (m, 2H); MS (ESI(+)) m/e 464 (M+H) + .
Example 834
5-[1-(2,4-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2,4-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.52 (m, 1H), 7.36 (td, J=9.7, 2.4 Hz, 1H), 7.19 (m, 1H), 6.97 (dd, J=3.8, 0.8 Hz, 1H), 4.57 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.18 (m, 2H), 2.92 (m, 1H), 2.07 (m, 1H), 1.93 (m, 1H), 1.52 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 835
5-[1-(2,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 2,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.37 (m, 3H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.57 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.46 (m, 1H), 3.19 (m, 2H), 2.93 (m, 1H), 2.13 (m, 1H), 1.92 (m, 1H), 1.54 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 836
5-[1-(3,5-difluorobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 52A, substituting 3,5-difluorobenzoyl chloride for 2-cyclopentylacetyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.34 (tt, J=9.4, 2.4 Hz, 1H), 7.19 (m, 2H), 6.98 (dd, J=3.8, 0.8 Hz, 1H), 4.55 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.55 (m, 1H), 3.15 (m, 2H), 2.90 (m, 1H), 2.03 (m, 1H), 1.90 (m, 1H), 1.61 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 837
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(2-methylpropanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (m, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 4.02 (m, 1H), 3.13 (m, 2H), 2.90 (m, 1H), 2.64 (m, 1H), 1.99 (m, 2H), 1.43 (m, 2H), 1.00 (m, 6H); MS (ESI(+)) m/e 412 (M+H) + .
Example 838
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(3-methylbutanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 3.96 (m, 1H), 3.10 (m, 2H), 2.64 (m, 1H), 2.21 (d, J=7.0 Hz, 2H), 1.99 (m, 3H), 1.43 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H) + .
Example 839
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylcyclopropyl)carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (d, J=0.9 Hz, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.33 (m, 2H), 3.11 (m, 1H), 2.93 (m, 2H), 1.99 (m, 2H), 1.47 (m, 2H), 1.23 (s, 3H), 0.80 (m, 2H), 0.54 (m, 2H); MS (ESI(+)) m/e 424 (M+H) + .
Example 840
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 3.94 (m, 1H), 3.13 (m, 2H), 2.66 (m, 3H), 2.50 (m, 2H), 1.97 (m, 2H), 1.57 (m, 1H), 1.41 (m, 1H); MS (ESI(+)) m/e 466 (M+H) + .
Example 841
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-ylcarboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (m, 2H), 8.50 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.69 (d, J=3.8 Hz, 1H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 4.07 (m, 1H), 3.84 (m, 2H), 3.40 (m, 2H), 3.13 (m, 2H), 2.89 (m, 1H), 2.64 (m, 1H), 1.98 (m, 2H), 1.77-1.30 (m, 6H); MS (ESI(+)) m/e 454 (M+H) + .
Example 842
5-[1-(2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.64 (m, 2H), 6.96 (d, J=3.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 4.02 (m, 1H), 3.12 (m, 2H), 2.88 (m, 1H), 2.63 (m, 1H), 1.99 (m, 2H), 1.43 (m, 2H), 1.00 (m, 6H); MS (ESI(+)) m/e 412 (M+H)+.
Example 843
5-[1-(3-methylbutanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 3.96 (m, 1H), 3.10 (m, 2H), 2.63 (m, 1H), 2.21 (m, 2H), 1.98 (m, 3H), 1.43 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 426 (M+H) + .
Example 844
5-{1-[(25)-2-methylbutanoyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (25)-2-methylbutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (d, J=3.8 Hz, 1H), 4.52 (d, J=5.8 Hz, 2H), 4.49 (m, 1H), 4.05 (m, 1H), 3.13 (m, 2H), 2.69 (m, 2H), 1.99 (m, 2H), 1.61-1.18 (m, 4H), 0.98 (m, 3H), 0.82 (m, 3H); MS (ESI(+)) m/e 426 (M+H) + .
Example 845
5-{1-[(1-methylcyclopropyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylcyclopropyl)carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.96 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.33 (m, 2H), 3.10 (m, 1H), 2.92 (m, 2H), 1.98 (m, 2H), 1.47 (m, 2H), 1.23 (s, 3H), 0.80 (m, 2H), 0.53 (m, 2H); MS (ESI(+)) m/e 424 (M+H) + .
Example 846
N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 3,3,3-trifluoropropanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.65 (m, 2H), 6.95 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.45 (m, 1H), 3.90 (m, 1H), 3.66 (m, 2H), 3.13 (m, 2H), 2.70 (m, 1H), 1.97 (m, 2H), 1.57 (m, 1H), 1.42 (m, 1H); MS (ESI(+)) m/e 452 (M+H) + .
Example 847
N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 4,4,4-trifluorobutanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.47 (m, 1H), 3.94 (m, 1H), 3.12 (m, 2H), 2.65 (m, 3H), 2.50 (m, 2H), 1.96 (m, 2H), 1.57 (m, 1H), 1.41 (m, 1H); MS (ESI(+)) m/e 466 (M+H) + .
Example 848
5-{1-[(4,4-difluorocyclohexyl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (4,4-difluorocyclohexyl)carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.06 (m, 1H), 3.13 (m, 2H), 2.82 (m, 1H), 2.65 (m, 1H), 2.10-1.80 (m, 6H), 1.80-1.30 (m, 6H); MS (ESI(+)) m/e 488 (M+H) + .
Example 849
5-[1-(tetrahydro-2H-pyran-4-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and tetrahydro-2H-pyran-4-ylcarboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.86 (m, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.06 (m, 1H), 3.84 (m, 2H), 3.38 (m, 2H), 3.12 (m, 2H), 2.89 (m, 1H), 2.64 (m, 1H), 1.98 (m, 2H), 1.65-1.30 (m, 6H); MS (ESI(+)) m/e 454 (M+H) + .
Example 850
5-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-hydroxy-2-methylpropanoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.47 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.95 (dd, J=3.7, 0.8 Hz, 1H), 5.39 (s, 1H), 5.00-4.30 (m, 2H), 4.53 (d, J=5.8 Hz, 2H), 3.10 (m, 1H), 3.10-2.60 (m, 2H), 1.96 (m, 2H), 1.50 (m, 2H), 1.32 (s, 6H); MS (ESI(+)) m/e 428 (M+H) + .
Example 851
5-{1-[(1-methylpiperidin-4-yl)carbonyl]piperidin-4-yl}-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and (1-methylpiperidin-4-yl)carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.8 Hz, 1H), 8.85 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.64 (m, 2H), 6.95 (d, J=3.8 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 4.48 (m, 1H), 4.00 (m, 1H), 3.04 (m, 4H), 2.80-2.57 (m, 4H), 2.13 (s, 3H), 2.07-1.80 (m, 4H), 1.81-0.93 (m, 4H); MS (ESI(+)) m/e 467 (M+H) + .
Example 852
5-[1-(2-cyanobenzoyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and 2-cyanobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.02 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.47 (s, 1H), 7.95 (m, 1H), 7.82 (m, 2H), 7.70-7.57 (m, 4H), 6.96 (dd, J=3.7, 0.8 Hz, 1H), 4.61 (m, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.35 (m, 1H), 3.14 (m, 2H), 2.97 (m, 1H), 2.09 (m, 1H), 1.89 (m, 1H), 1.60 (m, 2H); MS (ESI(+)) m/e 471 (M+H) + .
Example 853
5-[1-(pyridin-2-ylcarbonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for 3-methylbutan-1-amine and pyridin-2-ylcarboxylic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.8 Hz, 1H), 8.86 (m, 1H), 8.59 (m, 1H), 8.48 (s, 1H), 7.92 (td, J=7.7, 1.7 Hz, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 7.57 (dt, J=7.7, 1.1 Hz, 1H), 7.47 (m, 1H), 6.97 (dd, J=3.7, 0.8 Hz, 1H), 4.58 (m, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.72 (m, 1H), 3.17 (m, 2H), 2.93 (m, 1H), 2.08 (m, 1H), 1.91 (m, 1H), 1.58 (m, 2H); MS (ESI(+)) m/e 447 (M+H) + .
Example 854
2-cyclopentyl-N-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}acetamide
The title compound was prepared as described in Example 1A, substituting N-(4-aminophenyl)-2-cyclopentylacetamide for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-6-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.12 (bs, 1H), 9.77 (bs, 1H), 8.47-8.44 (m, 1H), 7.94 (s, 1H), 7.58-7.43 (m, 6H), 7.19 (dd, J=9.2, 1.7 Hz, 1H), 3.64 (bs, 2H), 2.30-2.19 (m, 3H), 1.82-1.65 (m, 2H), 1.66-1.43 (m, 4H), 1.26-1.08 (m, 2H); MS (ESI(+)) m/e 377 (M+H) + .
Example 855
tert-butyl 4-{4-[(imidazo[1,2-b]pyridazin-6-ylmethyl)carbamoyl]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-b]pyridazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.15 (t, J=5.9 Hz, 1H), 8.24 (s, 1H), 8.07 (d, J=9.3 Hz, 1H), 7.88-7.82 (m, 2H), 7.75 (d, J=1.2 Hz, 1H), 7.41-7.34 (m, 2H), 7.20 (d, J=9.3 Hz, 1H), 4.63 (d, J=5.8 Hz, 2H), 4.13-4.03 (m, 2H), 2.91-2.67 (m, 3H), 1.80-1.72 (m, 2H), 1.61-1.44 (m, 2H), 1.42 (s, 9H); MS (ESI(+)) m/e 436 (M+H) + .
Example 856
4-[(cyclopentylacetyl)amino]-N-(imidazo[1,2-b]pyridazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-b]pyridazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.38 (d, J=1.9 Hz, 1H), 8.28 (dd, J=9.4, 0.7 Hz, 1H), 8.07 (d, J=1.9 Hz, 1H), 7.90-7.84 (m, 2H), 7.79-7.66 (m, 3H), 4.91-4.79 (m, 2H), 2.43-2.25 (m, 3H), 1.92-1.78 (m, 2H), 1.79-1.50 (m, 4H), 1.33-1.18 (m, 2H); MS (ESI(+)) m/e 378 (M+H) + .
Example 857
5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
Example 857A
methyl 5-(3-cyclopropylpropioloyl)thiophene-2-carboxylate
Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate (500 mg, 2.443 mmol) was dissolved in triethylamine (5 mL) and the suspension was degassed with nitrogen. Copper(I) iodide (40 mg, 0.210 mmol) and bistriphenylphosphine palladium (II) chloride (40 mg, 0.057 mmol) were added followed by ethynylcyclopropane (162 mg, 2.443 mmol). The mixture was stirred overnight, diluted with methanol and concentrated to dryness. The crude material was partitioned between dichloromethane and water. The organic extracts were dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.
Example 857B
methyl 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylate
Methyl 5-(3-cyclopropylpropioloyl)thiophene-2-carboxylate (100 mg, 0.427 mmol) was dissolved in N,N-dimethylformamide (2 mL), and the solution was cooled to 0° C. Benzylhydrazine hydrochloride (74.5 mg, 0.470 mmol) was added followed by potassium carbonate (77 mg, 0.555 mmol). The mixture was stirred at 0° C. until the ice bath melted and was stirred overnight at room temperature. The solution was partitioned between water and ethyl acetate. The organic extract was dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.
Example 857C
5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid
The title compound was prepared as described in Example 4B, substituting methyl 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 857D
5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 5-(1-benzyl-3-cyclopropyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.91-7.87 (m, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.24 (m, 5H), 7.23-7.15 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.38 (s, 1H), 5.44 (bs, 2H), 4.47 (d, J=5.9 Hz, 2H), 1.94-1.81 (m, 1H), 0.97-0.86 (m, 2H), 0.72-0.59 (m, 2H); MS (ESI(+)) m/e 454 (M+H) + .
Example 858
5-[1-(2,2-dimethylpropyl)-1H-pyrazol-4-yl]-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
Example 858A
5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 5-bromothiophene-2-carboxylic acid for 4-nitrobenzoic acid.
Example 858B
The title compound was prepared as described in Example 51A, substituting 1-neopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.10-8.99 (m, 2H), 8.53 (d, J=1.3 Hz, 1H), 8.17 (d, J=0.9 Hz, 1H), 8.10 (d, J=0.5 Hz, 1H), 7.82-7.78 (m, 2H), 7.76 (d, J=3.8 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 3.92 (s, 2H), 0.92 (s, 9H); MS (ESI(+)) m/e 395 (M+H) + .
Example 859
5-[1-(propan-2-ylsulfonyl)piperidin-4-yl]-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 682, substituting propane-2-sulfonyl chloride for benzenesulfonyl chloride and N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.03 (t, J=5.8 Hz, 1H), 8.86 (d, J=1.5 Hz, 1H), 8.48 (s, 1H), 7.83 (dd, J=9.1, 0.9 Hz, 1H), 7.64 (m, 2H), 6.97 (dd, J=3.7, 0.9 Hz, 1H), 4.53 (d, J=5.8 Hz, 2H), 3.71 (m, 2H), 3.25 (m, 1H), 3.02 (m, 3H), 2.00 (m, 2H), 1.56 (m, 2H), 1.22 (d, J=6.8 Hz, 6H); MS (ESI(+)) m/e 448 (M+H)+.
Example 860
The title compound was prepared as described in Example 682, substituting N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-5-(piperidin-4-yl)thiophene-2-carboxamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.01 (t, J=5.9 Hz, 1H), 8.85 (s, 1H), 8.47 (s, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.81-7.69 (m, 3H), 7.71-7.55 (m, 4H), 6.90 (d, J=3.8 Hz, 1H), 4.51 (d, J=5.8 Hz, 2H), 3.73 (m, 2H), 2.84 (m, 1H), 2.37 (m, 2H), 1.99 (m, 2H), 1.61 (m, 2H); MS (ESI(+)) m/e 482 (M+H) + .
Example 861
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[(4-methyltetrahydro-2H-pyran-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.09-9.01 (m, 2H), 8.53 (d, J=1.4 Hz, 1H), 8.18-8.15 (m, 1H), 8.13 (d, J=0.5 Hz, 1H), 7.83-7.79 (m, 2H), 7.76 (d, J=3.9 Hz, 1H), 7.23 (d, J=3.9 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.04 (s, 2H), 3.68 (dt, J=11.4, 4.5 Hz, 2H), 3.51 (ddd, J=11.8, 9.2, 2.9 Hz, 2H), 1.50 (ddd, J=13.4, 9.1, 4.1 Hz, 2H), 1.33-1.18 (m, 2H), 0.96 (s, 3H); MS (ESI(+)) m/e 437 (M+H) + .
Example 862
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-6-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 10.14 (s, 1H), 8.52 (s, 1H), 8.01 (d, J=1.3 Hz, 1H), 7.65-7.58 (m, 2H), 7.54-7.47 (m, 2H), 7.31 (dd, J=9.2, 1.7 Hz, 1H), 7.20-7.13 (m, 2H), 4.11-3.99 (m, 2H), 3.68 (s, 2H), 2.89-2.54 (m, 3H), 1.76-1.66 (m, 2H), 1.53-1.32 (m, 11H); MS (ESI(+)) m/e 435 (M+H) + .
Example 863
N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide
Example 863A
2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-6-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 863B
N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.77 (s, 1H), 8.21 (d, J=2.2 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.55-7.35 (m, 4H), 7.33-7.26 (m, 1H), 7.25-7.17 (m, 3H), 4.83-4.74 (m, 1H), 3.91 (s, 2H), 3.68-3.58 (m, 1H), 3.30-3.18 (m, 1H), 3.02-2.78 (m, 2H), 2.01-1.91 (m, 1H), 1.87-1.50 (m, 3H); MS (ESI(+)) m/e 457 (M+H) + .
Example 864
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-[1-(phenylsulfonyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 682, substituting N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(piperidin-4-yl)benzamide for N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 9.04-8.96 (m, 1H), 8.51 (s, 1H), 8.05 (s, 1H), 7.85-7.79 (m, 5H), 7.73-7.66 (m, 1H), 7.67-7.59 (m, 2H), 7.35-7.28 (m, 2H), 4.72-4.67 (m, 2H), 3.96-3.88 (m, 2H), 2.63-2.51 (m, 1H), 2.48-2.37 (m, 2H), 1.93-1.85 (m, 2H), 1.86-1.72 (m, 2H); MS (ESI(+)) m/e 476 (M+H) + .
Example 865
2-(imidazo[1,2-a]pyridin-6-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.77 (d, J=1.4 Hz, 1H), 8.21 (dd, J=2.2, 0.7 Hz, 1H), 8.03 (d, J=2.2 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.53-7.47 (m, 2H), 7.23-7.17 (m, 2H), 4.73-4.64 (m, 1H), 4.21-4.13 (m, 1H), 3.91 (s, 2H), 3.27-3.14 (m, 1H), 2.99 (hept, J=6.7 Hz, 1H), 2.88-2.74 (m, 1H), 2.76-2.63 (m, 1H), 1.96-1.81 (m, 2H), 1.71-1.45 (m, 2H), 1.16-1.07 (m, 6H); MS (ESI(+)) m/e 405 (M+H)+.
Example 866
N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-6-yl)acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-6-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2,4-difluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.77 (d, J=1.4 Hz, 1H), 8.23-8.18 (m, 1H), 8.03 (d, J=2.2 Hz, 1H), 8.01-7.94 (m, 1H), 7.93-7.87 (m, 1H), 7.54-7.42 (m, 3H), 7.25-7.19 (m, 2H), 7.13-7.05 (m, 2H), 4.84-4.74 (m, 2H), 3.91 (s, 2H), 3.68-3.59 (m, 1H), 3.30-3.20 (m, 1H), 3.02-2.79 (m, 1H), 2.00-1.91 (m, 1H), 1.88-1.52 (m, 3H); MS (ESI(+)) m/e 475 (M+H) + .
Example 877
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide
Example 877A
methyl 4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)benzoate
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(methoxycarbonyl)benzoic acid for 4-nitrobenzoic acid.
Example 877B
4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)benzoic acid
The title compound was prepared as described in Example 4B, substituting methyl 4-((imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl)benzoate for methyl 4-(3-imidazo[1,2-a]pyridin-6-ylureido)benzoate.
Example 877C
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(2-methylpropyl)pyrrolidin-1-yl]carbonyl}benzamide
The title compound was prepared as described in Example 1A, substituting 2-isobutylpyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.17 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.89 (d, J=1.2 Hz, 1H), 7.56 (d, J=8.0 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.7 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 4.25-4.14 (m, 1H), 3.58-3.51 (m, 1H), 3.51-3.38 (m, 1H), 2.09-1.53 (m, 5H), 1.33-1.17 (m, 2H), 0.94 (d, J=6.4 Hz, 6H); MS (ESI(+)) m/e 405 (M+H)+.
Example 878
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}benzamide
The title compound was prepared as described in Example 1A, substituting (2R)-2-(methoxymethyl)pyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.18 (t, J=4.8 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.95 (d, J=8.3 Hz, 2H), 7.88 (s, 1H), 7.57 (d, J=7.7 Hz, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 6.86 (dd, J=7.0, 1.6 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.62-2.88 (br m, 8H), 2.05-1.64 (br m, 4H); MS (ESI(+)) m/e 393 (M+H) + .
Example 881
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(phenylsulfonyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-7-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.53 (t, J=5.9 Hz, 1H), 8.83 (d, J=6.9 Hz, 1H), 8.30 (d, J=2.1 Hz, 1H), 8.16-8.07 (m, 5H), 8.03-7.97 (m, 2H), 7.80-7.61 (m, 4H), 7.46 (dd, J=6.9, 1.6 Hz, 1H), 4.68 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 392 (M+H) + .
Example 882
4-(phenylsulfonyl)-N-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting [1,2,4]triazolo[1,5-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.32 (t, J=5.8 Hz, 1H), 8.92-8.87 (m, 1H), 8.49-8.46 (m, 1H), 8.07 (m, 4H), 8.01-7.95 (m, 2H), 7.85-7.78 (m, 1H), 7.75-7.67 (m, 1H), 7.68-7.60 (m, 3H), 4.57 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 393 (M+H) + .
Example 889
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide
Example 889A
tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)furan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)furan-2-carboxamide for 4-bromoaniline.
Example 889B
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}furan-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)furan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.70 (s, 2H), 9.28 (t, J=6.1 Hz, 1H), 8.87 (d, J=6.7 Hz, 1H), 8.33 (s, 2H), 8.15 (d, J=2.1 Hz, 1H), 8.00 (s, 1H), 7.82 (s, 1H), 7.49 (dd, J=7.0, 1.5 Hz, 1H), 7.26 (d, J=3.5 Hz, 1H), 6.72 (d, J=3.5 Hz, 1H), 4.73-4.59 (m, 4H), 3.66-3.56 (m, 2H), 3.41 (d, J=11.4 Hz, 8H); MS (ESI(+)) m/e 420 (M+H) + .
Example 892
5-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 857, substituting methylhydrazine for benzylhydrazine in Example 857B. 1 H NMR (300 MHz, DMSO-d 6 ) δ 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.30 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.32 (s, 1H), 4.47 (d, J=5.9 Hz, 2H), 3.84 (s, 3H), 1.97-1.84 (m, 1H), 1.04-0.89 (m, 2H), 0.75-0.63 (m, 2H); MS (ESI(+)) m/e 378 (M+H) + .
Example 893
5-[3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 857, substituting (2-methoxyethyl)hydrazine for benzylhydrazine in Example 857B. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.04 (t, J=6.0 Hz, 1H), 8.49 (dd, J=7.0, 1.0 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.31 (d, J=3.8 Hz, 1H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.31 (s, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.33 (t, J=5.5 Hz, 2H), 3.73 (t, J=5.5 Hz, 2H), 3.24 (s, 3H), 2.00-1.87 (m, 1H), 1.01-0.92 (m, 2H), 0.72-0.63 (m, 2H); MS (ESI(+)) m/e 422 (M+H)+.
Example 894
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
See Example 894A
tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline.
Example 894B
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-5-{1-[2-(piperazin-1-yl)ethyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(2-(4-(5-((imidazo[1,2-a]pyrazin-6-ylmethyl)carbamoyl)thiophen-2-yl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.52 (s, 2H), 9.28-9.17 (m, 2H), 8.68 (d, J=1.2 Hz, 1H), 8.36-8.30 (m, 1H), 8.27 (d, J=0.4 Hz, 1H), 8.05 (d, J=1.4 Hz, 1H), 7.91 (d, J=0.5 Hz, 1H), 7.81 (d, J=3.9 Hz, 1H), 7.27 (d, J=3.9 Hz, 1H), 4.71-4.48 (m, 2H), 4.07 (s, 8H), 3.37 (s, 4H); MS (ESI(+)) m/e 437 (M+H) + .
Example 897
N-(imidazo[1,2-a]pyrazin-6-ylmethyl)-4-(phenylsulfonyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.38 (t, J=5.8 Hz, 1H), 9.11 (s, 1H), 8.61-8.57 (m, 1H), 8.18 (s, 1H), 8.16-8.03 (m, 4H), 8.04-7.97 (m, 2H), 7.93-7.89 (m, 1H), 7.76-7.68 (m, 1H), 7.70-7.61 (m, 2H), 4.60 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 393 (M+H) + .
Example 898
N-(imidazo[1,2-a]pyridin-6-ylmethyl)-4-(phenylsulfonyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyridin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(phenylsulfonyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.47 (t, J=5.8 Hz, 1H), 8.82 (s, 1H), 8.35-8.30 (m, 1H), 8.19-8.14 (m, 1H), 8.12-8.08 (m, 4H), 8.05-7.88 (m, 4H), 7.76-7.68 (m, 1H), 7.68-7.60 (m, 2H), 4.61 (d, J=5.8 Hz, 2H); MS (ESI(+)) m/e 392 (M+H) + .
Example 899
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 51A, substituting 1-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide for 4-bromoaniline. 1 H NMR (500 MHz, DMSO-d 6 ) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.51 (dd, J=7.0, 0.7 Hz, 1H), 7.90 (d, J=0.8 Hz, 1H), 7.87 (d, J=3.9 Hz, 1H), 7.57-7.49 (m, 2H), 7.43 (s, 1H), 7.39 (d, J=3.9 Hz, 1H), 6.87 (dd, J=7.0, 1.6 Hz, 1H), 6.56 (d, J=1.9 Hz, 1H), 4.51 (d, J=5.9 Hz, 2H), 4.08 (d, J=7.4 Hz, 2H), 2.09 (dp, J=13.8, 6.9 Hz, 1H), 0.80 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 380 (M+H) + .
Example 900
tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.16 (s, 1H), 8.55 (d, J=6.9 Hz, 1H), 7.97 (s, 1H), 7.65-7.53 (m, 2H), 7.53-7.47 (m, 2H), 7.20-7.13 (m, 2H), 7.01-6.95 (m, 1H), 4.09-4.00 (m, 2H), 3.72 (s, 2H), 2.87-2.55 (m, 3H), 1.76-1.67 (m, 2H), 1.50-1.35 (m, 11H); MS (ESI(+)) m/e 435 (M+H) + .
Example 901
N-[(3-chloro imidazo[1,2-a]pyrazin-6-yl)methyl]-4-[(cyclopentylacetyl)amino]benzamide
The title compound was prepared as described in Example 396, substituting 4-(2-cyclopentylacetamido)-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.07 (s, 1H), 9.09 (s, 1H), 8.95 (t, J=5.7 Hz, 1H), 8.28 (s, 1H), 7.95 (s, 1H), 7.87-7.81 (m, 2H), 7.69-7.63 (m, 2H), 4.61 (d, J=5.6 Hz, 2H), 2.38-2.12 (m, 3H), 1.80-1.64 (m, 2H), 1.66-1.40 (m, 4H), 1.25-1.09 (m, 2H); MS (ESI(+)) m/e 412 (M+H) + .
Example 902
N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
Example 902A
2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 902B
N-{4-[1-(2,4-difluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2,4-difluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.29 (s, 1H), 8.84 (d, J=6.9 Hz, 1H), 8.31 (d, J=1.9 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 7.89 (s, 1H), 7.56-7.47 (m, 3H), 7.47-7.40 (m, 1H), 7.42-7.31 (m, 1H), 7.23-7.15 (m, 3H), 4.68-4.60 (m, 1H), 3.95 (bs, 2H), 3.58-3.44 (m, 1H), 3.26-3.09 (m, 1H), 2.94-2.70 (m, 2H), 1.94-1.81 (m, 1H), 1.79-1.40 (m, 3H); MS (ESI(+)) m/e 475 (M+H) + .
Example 903
2-(imidazo[1,2-a]pyridin-7-yl)-N-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and isobutyric acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.28 (s, 1H), 8.84 (d, J=6.9 Hz, 1H), 8.34-8.28 (m, 1H), 8.18-8.14 (m, 1H), 7.89 (s, 1H), 7.55-7.43 (m, 3H), 7.22-7.16 (m, 2H), 4.60-4.50 (m, 1H), 4.09-4.00 (m, 1H), 3.96 (s, 2H), 3.18-3.01 (m, 1H), 2.96-2.82 (m, 1H), 2.79-2.67 (m, 1H), 2.63-2.50 (m, 1H), 1.87-1.70 (m, 2H), 1.57-1.30 (m, 2H), 1.07-0.93 (m, 6H); MS (ESI(+)) m/e 405 (M+H) + .
Example 904
1-[(3-chloroimidazo[1,2-a]pyridin-7-yl)methyl]-3-{4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl}urea
The title compound was prepared as described in Example 396, substituting 1-(imidazo[1,2-a]pyridin-7-ylmethyl)-3-(4-(1-isobutyrylpiperidin-4-yl)phenyl)urea for 4-(3-imidazo[1,2-a]pyridin-6-ylureido)-N-((tetrahydro-2H-pyran-2-yl)methyl)benzamide. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.31 (bs, 1H), 8.24 (d, J=7.0 Hz, 1H), 7.58 (s, 1H), 7.46 (s, 1H), 7.35-7.29 (m, 2H), 7.12-7.02 (m, 3H), 6.62-6.55 (m, 1H), 4.38 (d, J=6.0 Hz, 2H), 4.36-4.19 (m, 2H), 2.93-2.62 (m, 4H), 1.85-1.77 (m, 2H), 1.53-1.37 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 454 (M+H) + .
Example 905
N-{4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
The title compound was prepared as described in Example 1A, substituting 2-(imidazo[1,2-a]pyridin-7-yl)-N-(4-(piperidin-4-yl)phenyl)acetamide for 3-methylbutan-1-amine and 2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.18 (d, J=2.2 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.89 (s, 1H), 7.56-7.35 (m, 5H), 7.33-7.25 (m, 1H), 7.25-7.17 (m, 3H), 4.83-4.74 (m, 1H), 3.99 (s, 2H), 3.68-3.59 (m, 1H), 3.31-3.18 (m, 1H), 3.03-2.76 (m, 2H), 2.00-1.92 (m, 1H), 1.87-1.51 (m, 3H); MS (ESI(+)) m/e 457 (M+H) + .
Example 906
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[1-methyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 857, substituting 4-methylpent-1-yne for ethynylcyclopropane in Example 857A and methylhydrazine for benzylhydrazine in Example 857B. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.05 (t, J=5.9 Hz, 1H), 8.49 (dd, J=6.9, 0.9 Hz, 1H), 7.89 (s, 1H), 7.74 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.40 (s, 1H), 7.35 (d, J=3.8 Hz, 1H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 6.46 (s, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.75 (s, 3H), 2.54-2.51 (m, 2H), 1.96-1.84 (m, 1H), 0.94 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 394 (M+H) + .
Example 907
5-[1-benzyl-3-(2-methylpropyl)-1H-pyrazol-5-yl]-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide
The title compound was prepared as described in Example 857, substituting 4-methylpent-1-yne for ethynylcyclopropane in Example 857A. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 9.05 (t, J=5.8 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 7.89 (s, 1H), 7.76 (d, J=3.9 Hz, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.42-7.38 (m, 2H), 7.37-7.23 (m, 3H), 7.17-7.11 (m, 2H), 6.85 (dd, J=7.0, 1.7 Hz, 1H), 6.56 (s, 1H), 5.35 (bs, 2H), 4.48 (d, J=5.9 Hz, 2H), 2.49-2.45 (m, 2H), 1.87-1.74 (m, 1H), 0.87 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 470 (M+H) + .
Example 908
4-[(cyclopentylacetyl)amino]-2-fluoro-N-(imidazo[1,2-a]pyrazin-6-ylmethyl)benzamide
The title compound was prepared as described in Example 1A, substituting imidazo[1,2-a]pyrazin-6-ylmethanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)-2-fluorobenzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.27 (s, 1H), 9.13 (s, 1H), 8.73-8.65 (m, 1H), 8.59-8.56 (m, 1H), 8.24 (s, 1H), 7.94-7.91 (m, 1H), 7.75-7.67 (m, 2H), 7.34 (dd, J=8.5, 1.9 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 2.37-2.32 (m, 2H), 2.32-2.16 (m, 1H), 1.82-1.68 (m, 2H), 1.67-1.44 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 396 (M+H) + .
Example 909
N-(2,5-difluorobenzyl)-N′-(imidazo[1,2-a]pyridin-7-ylmethyl)benzene-1,4-dicarboxamide
The title compound was prepared as described in Example 1A, substituting 2,5-difluorobenzyl amine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.42 (t, J=5.9 Hz, 1H), 9.20 (t, J=5.8 Hz, 1H), 8.83 (d, J=6.9 Hz, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.10 (d, J=2.0 Hz, 1H), 8.04-8.00 (m, 4H), 7.78 (s, 1H), 7.45 (dd, J=6.9, 1.6 Hz, 1H), 7.32-7.12 (m, 3H), 4.69 (d, J=5.8 Hz, 2H), 4.52 (d, J=5.7 Hz, 2H); MS (ESI(+)) m/e 421 (M+H) + .
Example 910
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-{[2-(propan-2-yl)pyrrolidin-1-yl]carbonyl}benzamide
The title compound was prepared as described in Example 1A, substituting (propan-2-yl)pyrrolidine for 3-methylbutan-1-amine and 4-(imidazo[1,2-a]pyridin-7-ylmethylcarbamoyl)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.44-9.36 (m, 1H), 8.86 (d, J=6.9 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.14 (d, J=2.1 Hz, 1H), 8.01-7.95 (m, 2H), 7.80 (s, 1H), 7.65-7.59 (m, 2H), 7.49 (d, J=7.6 Hz, 1H), 4.69 (d, J=5.8 Hz, 2H), 4.15-4.05 (m, 1H), 3.47-3.19 (m, 2H), 2.39-2.26 (m, 1H), 1.96-1.57 (m, 4H), 0.93-0.85 (m, 6H); MS (ESI(+)) m/e 391 (M+H) + .
Example 911
N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
Example 911A
N′-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide
A suspension of 4-nitrobenzohydrazide (0.500 g, 2.76 mmol), and 4-methylmorpholine (0.455 ml, 4.14 mmol) were stirred in dichloromethane (20 ml). 3,3-Dimethylbutanoyl chloride (0.422 ml, 3.04 mmol) was added and the reaction mixture was stirred for 2 hours. Normal phase chromatography of the crude reaction mixture gave the title compound.
Example 911B
2-neopentyl-5-(4-nitrophenyl)-1,3,4-oxadiazole
A mixture of N′-(3,3-dimethylbutanoyl)-4-nitrobenzohydrazide (0.556 g, 1.991 mmol) and methyl N-(triethylammoniumsulfonyl)carbamate (0.572 g, 2.389 mmol) in tetrahydrofuran (10 ml) was heated to 120° C. in a microwave for 45 minutes. The crude reaction mixture was concentrated and purified by normal phase chromatography to give the title compound.
Example 911C
4-(5-neopentyl-1,3,4-oxadiazol-2-yl)aniline
The title compound was prepared as described in Example 1B, substituting 2-neopentyl-5-(4-nitrophenyl)-1,3,4-oxadiazole for tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate.
Example 911D
N-{4-[5-(2,2-dimethylpropyl)-1,3,4-oxadiazol-2-yl]phenyl}-1-(pyridazin-3-yl)azetidine-3-carboxamide
The title compound was prepared as described in Example 1A, substituting 4-(5-neopentyl-1,3,4-oxadiazol-2-yl)aniline for tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid for 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.55 (s, 1H), 8.49 (d, J=7.0 Hz, 1H), 7.96-7.89 (m, 3H), 7.86-7.79 (m, 2H), 7.53 (d, J=1.1 Hz, 1H), 7.49 (s, 1H), 6.88 (dd, J=7.0, 1.6 Hz, 1H), 3.77 (s, 2H), 2.82 (s, 2H), 1.02 (s, 9H); MS (ESI(+)) m/e 390 (M+H) + .
Example 912
tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate
Example 912A
tert-butyl 4-(4-amino-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate
The title compound was prepared as described in Example 51A, substituting tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-2-fluoroaniline for 4-bromoaniline.
Example 912B
tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1B, substituting tert-butyl 4-(4-amino-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate for N-isopentyl-4-nitrobenzamide.
Example 912C
tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate
The title compound was prepared as described in Example 1C, substituting tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate for 4-amino-N-isopentylbenzamide and imidazo[1,2-a]pyridin-7-ylmethanamine for imidazo[1,2-a]pyridin-6-amine. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 8.49 (d, J=7.0 Hz, 1H), 8.37 (d, J=2.3 Hz, 1H), 7.97 (t, J=8.5 Hz, 1H), 7.88 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.39 (s, 1H), 7.12-7.04 (m, 2H), 7.00-6.94 (m, 1H), 6.82 (dd, J=7.0, 1.6 Hz, 1H), 4.35 (d, J=5.9 Hz, 2H), 4.10-4.01 (m, 2H), 2.89-2.56 (m, 3H), 1.77-1.68 (m, 2H), 1.41 (s, 11H); MS (ESI(+)) m/e 468 (M+H) + .
Example 958
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(pyrrolidin-1-ylcarbonyl)piperidin-4-yl]benzamide
The title compound was prepared as described in Example 1068, substituting pyrrolidine-1-carbonyl chloride for piperidine-1-carbonyl chloride. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.28-9.21 (m, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.91-7.85 (m, 2H), 7.77 (s, 1H), 7.47 (dd, J=7.0, 1.6 Hz, 1H), 7.43-7.36 (m, 2H), 4.67 (d, J=5.8 Hz, 2H), 3.83-3.75 (m, 2H), 3.35-3.23 (m, 4H), 2.85-2.72 (m, 3H), 1.81-1.69 (m, 6H), 1.71-1.53 (m, 2H); MS (ESI(+)) m/e 432 (M+H) + .
Example 1067
tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate
The title compound was prepared as described in Example 1A, substituting tert-butyl 4-(4-amino-3-fluorophenyl)piperidine-1-carboxylate for 3-methylbutan-1-amine and 2-(imidazo[1,2-a]pyridin-7-yl)acetic acid hydrochloride for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.97 (s, 1H), 8.58 (d, J=6.9 Hz, 1H), 8.00 (s, 1H), 7.77-7.67 (m, 2H), 7.58 (d, J=1.4 Hz, 1H), 7.15 (dd, J=12.2, 1.9 Hz, 1H), 7.06-6.99 (m, 2H), 4.10-4.01 (m, 2H), 3.82 (bs, 2H), 2.94-2.58 (m, 3H), 1.78-1.69 (m, 2H), 1.53-1.36 (m, 11H); MS (ESI(+)) m/e 453 (M+H) + .
Example 1068
N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-[1-(piperidin-1-ylcarbonyl)piperidin-4-yl]benzamide
A solution of piperidine-1-carbonyl chloride (0.033 g, 0.224 mmol) in N-methyl-2-pyrrolidinone (1 mL) was treated with N-(imidazo[1,2-a]pyridin-7-ylmethyl)-4-(piperidin-4-yl)benzamide (0.05 g, 0.150 mmol) and triethylamine (0.042 ml, 0.299 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The mixture was purified by reverse-phase HPLC to give the title compound. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.84 (d, J=7.0 Hz, 1H), 8.30 (d, J=2.1 Hz, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.91-7.84 (m, 2H), 7.76 (s, 1H), 7.50-7.44 (m, 1H), 7.42-7.36 (m, 2H), 4.67 (d, J=5.8 Hz, 2H), 3.71-3.62 (m, 2H), 3.16-3.10 (m, 4H), 2.89-2.68 (m, 3H), 1.81-1.72 (m, 2H), 1.68-1.44 (m, 8H); MS (ESI(+)) m/e 446 (M+H) + .
Example 1069
1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
Example 1069A
1-(2-fluoro-4-(piperidin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-(3-fluoro-4-{[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]amino}phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 1069B
1-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
The title compound was prepared as described in Example 1A, substituting 1-(2-fluoro-4-(piperidin-4-yl)phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.73 (d, J=7.0 Hz, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.99-7.95 (m, 1H), 7.85-7.77 (m, 2H), 7.50-7.39 (m, 6H), 7.11-6.99 (m, 2H), 4.84-4.72 (m, 1H), 4.60 (bs, 2H), 3.93-3.73 (m, 1H), 3.29-3.15 (m, 1H), 3.00-2.76 (m, 2H), 2.03-1.84 (m, 1H), 1.83-1.53 (m, 3H); MS (ESI(+)) m/e 472 (M+H) + .





TABLE 25



The following Examples were prepared essentially as described in Example

1069, substituting an appropriate carboxylic acid in Example 1069B.





Ex
Name
MS



1070
1-{4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-2-
(ESI(+))


fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 452



(M + H) +

1071
1-{4-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]-2-
(ESI(+))


fluorophenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 466



(M + H) +

1072
1-{2-fluoro-4-[1-(4-methylpentanoyl)piperidin-4-
(ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 466



(M + H) +

1073
1-(2-fluoro-4-{1-[(2S)-2-methylbutanoyl]piperidin-4-
(ESI(+))


yl}phenyl)-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 452



(M + H) +

1074
1-{2-fluoro-4-[1-(tetrahydro-2H-pyran-4-
(ESI(+))


ylcarbonyl)piperidin-4-yl]phenyl}-3-(imidazo[1,2-
m/e 480


a]pyridin-7-ylmethyl)urea
(M + H) +

1075
1-{2-fluoro-4-[1-(pyridin-2-ylcarbonyl)piperidin-4-
(ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 473



(M + H) +

1076
1-{4-[1-(2-cyanobenzoyl)piperidin-4-yl]-2-fluorophenyl}-
(ESI(+))


3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 497



(M + H) +

1078
1-{2-fluoro-4-[1-(2-methylpropanoyl)piperidin-4-
(ESI(+))


yl]phenyl}-3-(imidazo[1,2-a]pyridin-7-ylmethyl)urea
m/e 438



(M + H) +













































Example 1077
4-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]phenyl}-N,N-dimethylpiperidine-1-carboxamide
The title compound was prepared as described in Example 1068, substituting N,N-dimethylamine-1-carbonyl chloride for piperidine-1-carbonyl chloride. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.75 (d, J=7.0 Hz, 1H), 8.19-8.15 (m, 1H), 8.01-7.97 (m, 1H), 7.89-7.83 (m, 2H), 7.80 (s, 1H), 7.51-7.46 (m, 1H), 7.44-7.38 (m, 2H), 4.77 (s, 2H), 3.85-3.76 (m, 2H), 2.98-2.77 (m, 9H), 1.90-1.81 (m, 2H), 1.81-1.66 (m, 2H); MS (ESI(+)) m/e 406 (M+H) + .
Example 1079
4-[(cyclopentylacetyl)amino]-N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]benzamide
The title compound was prepared as described in Example 1A, substituting (7-fluoroimidazo[1,2-a]pyridin-6-yl)methanamine for 3-methylbutan-1-amine and 4-(2-cyclopentylacetamido)benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, DMSO-d 6 ) δ ppm 10.08 (s, 1H), 8.87 (t, J=5.5 Hz, 1H), 8.56 (d, J=7.3 Hz, 1H), 7.96 (s, 1H), 7.88-7.82 (m, 2H), 7.71-7.64 (m, 2H), 7.52 (d, J=1.2 Hz, 1H), 7.46-7.39 (m, 1H), 4.49 (d, J=5.5 Hz, 2H), 2.36-2.30 (m, 2H), 2.31-2.15 (m, 1H), 1.81-1.68 (m, 2H), 1.68-1.43 (m, 4H), 1.26-1.10 (m, 2H); MS (ESI(+)) m/e 395 (M+H) + .
Example 1080
N-[(7-fluoroimidazo[1,2-a]pyridin-6-yl)methyl]-5-[1-(2-methylpropyl)-1H-pyrazol-4-yl]thiophene-2-carboxamide
The title compound was prepared as described in Example 1A, substituting (7-fluoroimidazo[1,2-a]pyridin-6-yl)methanamine for 3-methylbutan-1-amine and 5-(1-isobutyl-1H-pyrazol-4-yl)thiophene-2-carboxylic acid for 4-nitrobenzoic acid. 1 H NMR (300 MHz, DMSO-d 6 ) δ ppm 8.93 (t, J=5.5 Hz, 1H), 8.58 (d, J=7.7 Hz, 1H), 8.14 (d, J=0.8 Hz, 1H), 7.98 (s, 1H), 7.80 (d, J=0.8 Hz, 1H), 7.73 (d, J=3.8 Hz, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.44 (d, J=11.0 Hz, 1H), 7.21 (d, J=3.8 Hz, 1H), 4.48 (d, J=5.5 Hz, 2H), 3.92 (d, J=7.2 Hz, 2H), 2.21-2.05 (m, 1H), 0.85 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 398 (M+H) + .
Example 1081
N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
Example 1081A
N-(2-fluoro-4-(piperidin-4-yl)phenyl)-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
The title compound was prepared as described in Example 28A, substituting tert-butyl 4-{3-fluoro-4-[(imidazo[1,2-a]pyridin-7-ylacetyl)amino]phenyl}piperidine-1-carboxylate for tert-butyl 4-(4-(3-imidazo[1,2-a]pyridin-6-ylureido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate.
Example 1081B
N-[4-(1-benzoylpiperidin-4-yl)-2-fluorophenyl]-2-(imidazo[1,2-a]pyridin-7-yl)acetamide
The title compound was prepared as described in Example 1A, substituting N-(2-fluoro-4-(piperidin-4-yl)phenyl)-2-(imidazo[1,2-a]pyridin-7-yl)acetamide for 3-methylbutan-1-amine and benzoic acid for 4-nitrobenzoic acid. 1 H NMR (400 MHz, methanol-d 4 ) δ ppm 8.75 (dd, J=6.9, 0.9 Hz, 1H), 8.19 (dd, J=2.2, 0.8 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.91 (s, 1H), 7.78 (t, J=8.2 Hz, 1H), 7.53-7.38 (m, 6H), 7.16-7.04 (m, 2H), 4.83-4.69 (m, 1H), 4.06 (s, 2H), 3.91-3.79 (m, 1H), 3.30-3.14 (m, 1H), 3.03-2.81 (m, 2H), 2.07-1.54 (m, 4H); MS (ESI(+)) m/e 457 (M+H)+.