KR20070077468A

KR20070077468A - 단백질 키나아제 활성을 저해하는 이미다조피리딘 유도체,이의 제조방법 및 이를 함유하는 약학 조성물

단백질 키나아제 활성을 저해하는 이미다조피리딘 유도체,이의 제조방법 및 이를 함유하는 약학 조성물 Download PDF

Info

Publication number: KR20070077468A
Authority: KR; South Korea
Prior art keywords: imidazo; pyridine; carboxylic acid; phenyl; amide
Prior art date: 2006-01-23
Legal status : Withdrawn

Application number

KR1020070007182A

Other languages

English (en)

Korean (ko)

Inventor

이승철

최진석

오정훈

박분생

김용은

이준희

신동규

김철민

현영란

이철순

조중명

노성구

Original Assignee

크리스탈지노믹스(주)

Priority date

2006-01-23

Filing date

2007-01-23

Publication date

2007-07-26

2007-01-23 Application filed by 크리스탈지노믹스(주) filed Critical 크리스탈지노믹스(주)

2007-07-26 Publication of KR20070077468A publication Critical patent/KR20070077468A/ko

Status Withdrawn legal-status Critical Current

Links

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238000002360 preparation method Methods 0.000 title description 6
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125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 18
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230000002401 inhibitory effect Effects 0.000 claims description 16
ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical compound NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 claims description 14
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
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125000004122 cyclic group Chemical group 0.000 claims description 12
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239000001257 hydrogen Substances 0.000 claims description 12
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125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Chemical group 0.000 claims description 10
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JSRJCOJTWVQZSD-UHFFFAOYSA-N 2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CO1 JSRJCOJTWVQZSD-UHFFFAOYSA-N 0.000 claims description 9
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125000003282 alkyl amino group Chemical group 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 9
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
102000043136 MAP kinase family Human genes 0.000 claims description 8
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102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
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ZXISZMDLMKPPRD-UHFFFAOYSA-N 2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC=C1 ZXISZMDLMKPPRD-UHFFFAOYSA-N 0.000 claims description 6
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QLXAAIYGPASHLZ-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 QLXAAIYGPASHLZ-UHFFFAOYSA-N 0.000 claims description 3
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JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
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UOPKVHCDEOWBAC-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 UOPKVHCDEOWBAC-UHFFFAOYSA-N 0.000 claims description 2
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QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 2
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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150000003217 pyrazoles Chemical class 0.000 claims description 2
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DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
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MYMLGBAVNHFRJS-UHFFFAOYSA-N trifluoromethanamine Chemical compound NC(F)(F)F MYMLGBAVNHFRJS-UHFFFAOYSA-N 0.000 claims description 2
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IYDOPXDHGIQJRR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 IYDOPXDHGIQJRR-UHFFFAOYSA-N 0.000 claims 1
GVIOPRAVURDOPN-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 GVIOPRAVURDOPN-UHFFFAOYSA-N 0.000 claims 1
BJKIFPFBHVOYMH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)C=CN=C2N1 BJKIFPFBHVOYMH-UHFFFAOYSA-N 0.000 claims 1
RKXLHWLESRGUHW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CC(=CC=3)N3CCCCC3)C=CN=C2N1 RKXLHWLESRGUHW-UHFFFAOYSA-N 0.000 claims 1
HTUQLRGQAKIXEG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(5-methyl-1h-pyrazol-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1N=C(C)C=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 HTUQLRGQAKIXEG-UHFFFAOYSA-N 0.000 claims 1
LMWBLUOSHRWDFY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(5-methylhexan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)CCC(C)C)=CC=NC=2NC=1C1=CC=C(F)C=C1 LMWBLUOSHRWDFY-UHFFFAOYSA-N 0.000 claims 1
OWMRNYYYDXSHOZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(5-methylpyridin-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1=CC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OWMRNYYYDXSHOZ-UHFFFAOYSA-N 0.000 claims 1
NBOSZAQIZQBVIZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(6-methoxy-2-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=NC(OC)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 NBOSZAQIZQBVIZ-UHFFFAOYSA-N 0.000 claims 1
VRTRQVPLCINGQW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(6-methoxy-4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 VRTRQVPLCINGQW-UHFFFAOYSA-N 0.000 claims 1
PLRHNKUYIYOGHI-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(6-methoxy-5-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(C)C(OC)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 PLRHNKUYIYOGHI-UHFFFAOYSA-N 0.000 claims 1
PZYPBNVFICAMJQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(6-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 PZYPBNVFICAMJQ-UHFFFAOYSA-N 0.000 claims 1
YETNXCCQDPJOKQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 YETNXCCQDPJOKQ-UHFFFAOYSA-N 0.000 claims 1
MRYBKVJSDGVAIJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[1-(hydroxymethyl)cyclopentyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(F)=CC=3)=NC=2C=1C(=O)NC1(CO)CCCC1 MRYBKVJSDGVAIJ-UHFFFAOYSA-N 0.000 claims 1
SCONMLNPUQKGHM-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(2-fluoropyridin-4-yl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=C(F)N=CC=3)C=CN=C2N1 SCONMLNPUQKGHM-UHFFFAOYSA-N 0.000 claims 1
UDGGXLPMLOQYCY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(2-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 UDGGXLPMLOQYCY-UHFFFAOYSA-N 0.000 claims 1
OOTQHVRYFXGMCL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(2-methylpyridin-3-yl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OOTQHVRYFXGMCL-UHFFFAOYSA-N 0.000 claims 1
UJQFOUYJDYVEIK-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-(3-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 UJQFOUYJDYVEIK-UHFFFAOYSA-N 0.000 claims 1
YXWSHPHZQFVQNM-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[2-(methylamino)pyridin-4-yl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NC)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 YXWSHPHZQFVQNM-UHFFFAOYSA-N 0.000 claims 1
CQLBZSYBRGRBDX-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[3-(3-morpholin-4-ylpropoxy)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=C(OCCCN4CCOCC4)C=CC=3)C=CN=C2N1 CQLBZSYBRGRBDX-UHFFFAOYSA-N 0.000 claims 1
DKAAUOXUZFLKMS-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[3-(trifluoromethyl)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=C(C=CC=3)C(F)(F)F)C=CN=C2N1 DKAAUOXUZFLKMS-UHFFFAOYSA-N 0.000 claims 1
DRCCBKPDCHOIJO-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[4-(methanesulfonamido)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 DRCCBKPDCHOIJO-UHFFFAOYSA-N 0.000 claims 1
KZXMYTBRBSQBKT-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=NC=CC(C(=O)NCCC=3C=CC(NS(=O)(=O)C(F)(F)F)=CC=3)=C2N1 KZXMYTBRBSQBKT-UHFFFAOYSA-N 0.000 claims 1
NHHOETDOAXJFKA-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[2-[4-[(4-methylpiperazine-1-carbonyl)amino]phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC(C=C1)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 NHHOETDOAXJFKA-UHFFFAOYSA-N 0.000 claims 1
QXYQCYVVDIZAGT-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-(6-fluoropyridin-3-yl)propyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCCC=3C=NC(F)=CC=3)C=CN=C2N1 QXYQCYVVDIZAGT-UHFFFAOYSA-N 0.000 claims 1
LPFRRWLBWNPBNN-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[3-(trifluoromethoxy)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C(OC(F)(F)F)C=CC=3)C=CN=C2N1 LPFRRWLBWNPBNN-UHFFFAOYSA-N 0.000 claims 1
OXVQBKMXTCVMJN-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-(2-methylpropoxy)pyridin-3-yl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC(C)COC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OXVQBKMXTCVMJN-UHFFFAOYSA-N 0.000 claims 1
XJPAIKWFDMNTHH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pentan-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(CC)CC)=CC=NC=2NC=1C1=CC=C(F)C=C1 XJPAIKWFDMNTHH-UHFFFAOYSA-N 0.000 claims 1
QAGFQPQTMMVBOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CC=CC=3)C=CN=C2N1 QAGFQPQTMMVBOB-UHFFFAOYSA-N 0.000 claims 1
HUBLLQRDAVHKSE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-phenyl-n-propan-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)C(C=1N=2)=CC=NC=1NC=2C1=CC=C(F)C=C1 HUBLLQRDAVHKSE-UHFFFAOYSA-N 0.000 claims 1
OPKDMPYKGNOJNL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-piperidin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CCNCC3)C=CN=C2N1 OPKDMPYKGNOJNL-UHFFFAOYSA-N 0.000 claims 1
ZNOJAIYGZRZNHV-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3N=CC=CC=3)C=CN=C2N1 ZNOJAIYGZRZNHV-UHFFFAOYSA-N 0.000 claims 1
DYEDOXXZFLAMCF-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 DYEDOXXZFLAMCF-UHFFFAOYSA-N 0.000 claims 1
BVQXBIYLJQDDNR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CN=CC=3)C=CN=C2N1 BVQXBIYLJQDDNR-UHFFFAOYSA-N 0.000 claims 1
CLCZTFQKXCHQGG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-quinolin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CC=CC4=NC=3)C=CN=C2N1 CLCZTFQKXCHQGG-UHFFFAOYSA-N 0.000 claims 1
IHOYHHJZSFKVHH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-quinolin-6-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CC=NC4=CC=3)C=CN=C2N1 IHOYHHJZSFKVHH-UHFFFAOYSA-N 0.000 claims 1
KHPNUIAWAQGPJW-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(=CC=3)N3CCOCC3)=NC=2C=1C(=O)NC1=CC=CN=C1 KHPNUIAWAQGPJW-UHFFFAOYSA-N 0.000 claims 1
NPOWZLUWBWSCRY-UHFFFAOYSA-N 2-(4-piperidin-1-ylphenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(=CC=3)N3CCCCC3)=NC=2C=1C(=O)NC1=CC=CN=C1 NPOWZLUWBWSCRY-UHFFFAOYSA-N 0.000 claims 1
PQJRVDCPLYXOAN-UHFFFAOYSA-N 2-(furan-2-yl)-n-(2-pyridin-2-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3OC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CC=N1 PQJRVDCPLYXOAN-UHFFFAOYSA-N 0.000 claims 1
NEUQSYHOGRTVPT-UHFFFAOYSA-N 2-(furan-2-yl)-n-(2-pyridin-3-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3OC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CN=C1 NEUQSYHOGRTVPT-UHFFFAOYSA-N 0.000 claims 1
PKFONCXRXGYJNT-UHFFFAOYSA-N 2-(furan-2-yl)-n-(2-pyridin-4-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3OC=CC=3)=NC=2C=1C(=O)NCCC1=CC=NC=C1 PKFONCXRXGYJNT-UHFFFAOYSA-N 0.000 claims 1
CCSHLFLPHURCNU-UHFFFAOYSA-N 2-(furan-2-yl)-n-(3-pyridin-3-ylpropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3OC=CC=3)=NC=2C=1C(=O)NCCCC1=CC=CN=C1 CCSHLFLPHURCNU-UHFFFAOYSA-N 0.000 claims 1
WIHOVJJYLFHKFU-UHFFFAOYSA-N 2-(furan-2-yl)-n-(3-pyridin-4-ylpropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3OC=CC=3)=NC=2C=1C(=O)NCCCC1=CC=NC=C1 WIHOVJJYLFHKFU-UHFFFAOYSA-N 0.000 claims 1
LUXYKJRTIVWRLO-UHFFFAOYSA-N 2-(furan-2-yl)-n-[2-(2-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 LUXYKJRTIVWRLO-UHFFFAOYSA-N 0.000 claims 1
JZXPPWUHYRPEJD-UHFFFAOYSA-N 2-(furan-2-yl)-n-[2-(3-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2OC=CC=2)=C1 JZXPPWUHYRPEJD-UHFFFAOYSA-N 0.000 claims 1
ANSHOPYYNAHZCP-UHFFFAOYSA-N 2-(furan-2-yl)-n-[2-[4-(methanesulfonamido)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 ANSHOPYYNAHZCP-UHFFFAOYSA-N 0.000 claims 1
LDDCSDYOXIOVRU-UHFFFAOYSA-N 2-(furan-2-yl)-n-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CCNC(=O)C1=CC=NC2=C1NC(C=1OC=CC=1)=N2 LDDCSDYOXIOVRU-UHFFFAOYSA-N 0.000 claims 1
VSGNIHWLYWCPAG-UHFFFAOYSA-N 2-(furan-3-yl)-n-(2-pyridin-2-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=COC=C3)=NC=2C=1C(=O)NCCC1=CC=CC=N1 VSGNIHWLYWCPAG-UHFFFAOYSA-N 0.000 claims 1
SVWGARGNXASWPF-UHFFFAOYSA-N 2-(furan-3-yl)-n-(2-pyridin-3-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=COC=C3)=NC=2C=1C(=O)NCCC1=CC=CN=C1 SVWGARGNXASWPF-UHFFFAOYSA-N 0.000 claims 1
YNURAOKTQSBWLD-UHFFFAOYSA-N 2-(furan-3-yl)-n-(2-pyridin-4-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=COC=C3)=NC=2C=1C(=O)NCCC1=CC=NC=C1 YNURAOKTQSBWLD-UHFFFAOYSA-N 0.000 claims 1
SUXOSKYHNOHKSZ-UHFFFAOYSA-N 2-(furan-3-yl)-n-(3-pyridin-3-ylpropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=COC=C3)=NC=2C=1C(=O)NCCCC1=CC=CN=C1 SUXOSKYHNOHKSZ-UHFFFAOYSA-N 0.000 claims 1
KNRPYKSEEOGBLC-UHFFFAOYSA-N 2-(furan-3-yl)-n-(3-pyridin-4-ylpropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=COC=C3)=NC=2C=1C(=O)NCCCC1=CC=NC=C1 KNRPYKSEEOGBLC-UHFFFAOYSA-N 0.000 claims 1
FMFFFDSDWRKNIK-UHFFFAOYSA-N 2-(furan-3-yl)-n-[2-(2-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 FMFFFDSDWRKNIK-UHFFFAOYSA-N 0.000 claims 1
ZYMWSSWMOUVXRN-UHFFFAOYSA-N 2-(furan-3-yl)-n-[2-(3-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=COC=C2)=C1 ZYMWSSWMOUVXRN-UHFFFAOYSA-N 0.000 claims 1
KNJXEPXFBQECHC-UHFFFAOYSA-N 2-(furan-3-yl)-n-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CCNC(=O)C1=CC=NC2=C1NC(C1=COC=C1)=N2 KNJXEPXFBQECHC-UHFFFAOYSA-N 0.000 claims 1
YANQLUHXIURGSC-UHFFFAOYSA-N 2-[2-[2-[[2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(Cl)=CC=1)Cl)N2 YANQLUHXIURGSC-UHFFFAOYSA-N 0.000 claims 1
AUWDQLMIROWQBQ-UHFFFAOYSA-N 2-[3-[2-[(2-phenyl-1h-imidazo[4,5-b]pyridine-7-carbonyl)amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 AUWDQLMIROWQBQ-UHFFFAOYSA-N 0.000 claims 1
BEGFBKZRIWCJJK-UHFFFAOYSA-N 2-[3-[2-[[2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 BEGFBKZRIWCJJK-UHFFFAOYSA-N 0.000 claims 1
FIKYJRZIEBMIRV-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCCCC1 FIKYJRZIEBMIRV-UHFFFAOYSA-N 0.000 claims 1
VDNHHYXGZIFLMB-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCCC1 VDNHHYXGZIFLMB-UHFFFAOYSA-N 0.000 claims 1
WNKHXYVQIDVFHO-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C(=CC=NC=2)C)C=C1 WNKHXYVQIDVFHO-UHFFFAOYSA-N 0.000 claims 1
XVCQHGPGUXYVTR-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC(C)=CC=2)C=C1 XVCQHGPGUXYVTR-UHFFFAOYSA-N 0.000 claims 1
XAWXRXNZBKUQHS-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC=CC=2)C=C1 XAWXRXNZBKUQHS-UHFFFAOYSA-N 0.000 claims 1
KYDFTLLBJAJVRL-UHFFFAOYSA-N 2-[4-(diethylamino)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 KYDFTLLBJAJVRL-UHFFFAOYSA-N 0.000 claims 1
OGPAURVRXPCBML-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 OGPAURVRXPCBML-UHFFFAOYSA-N 0.000 claims 1
CAWVZSLQMHKENN-UHFFFAOYSA-N 2-[4-(methylsulfinylmethyl)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(CS(=O)C)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 CAWVZSLQMHKENN-UHFFFAOYSA-N 0.000 claims 1
NIWPQBLXDNURDI-UHFFFAOYSA-N 2-[4-(piperidin-4-ylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NC1CCNCC1 NIWPQBLXDNURDI-UHFFFAOYSA-N 0.000 claims 1
PFCCDXDYVNKMHB-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethyl-methylamino]phenyl]-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(C)CCN(CC)CC)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 PFCCDXDYVNKMHB-UHFFFAOYSA-N 0.000 claims 1
XASORHMQUPDWQW-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCN(CC)CC)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 XASORHMQUPDWQW-UHFFFAOYSA-N 0.000 claims 1
JEQHSKOSWDGKJD-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-n-(4,6-dimethylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(C)CCN(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC(C)=NC=3)C)C=CN=C2N1 JEQHSKOSWDGKJD-UHFFFAOYSA-N 0.000 claims 1
QSUFKEYHZODFPP-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-n-(4-ethoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N(C)CCN(C)C)N2 QSUFKEYHZODFPP-UHFFFAOYSA-N 0.000 claims 1
YMDRBMAVRQKSSB-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-n-(4-ethylsulfanylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N(C)CCN(C)C)N2 YMDRBMAVRQKSSB-UHFFFAOYSA-N 0.000 claims 1
GNRRVQLUKYFLAY-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(C)CCN(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(C)=CC=3)C=CN=C2N1 GNRRVQLUKYFLAY-UHFFFAOYSA-N 0.000 claims 1
SMZUUCQJFAOUCS-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(1-hydroxy-2-methylpropan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC(C)(C)CO)C=CN=C2N1 SMZUUCQJFAOUCS-UHFFFAOYSA-N 0.000 claims 1
SWQBDNCFYKBTOO-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(2,4,4-trimethylpentan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC(C)(C)CC(C)(C)C)C=CN=C2N1 SWQBDNCFYKBTOO-UHFFFAOYSA-N 0.000 claims 1
DRZJFVDIROQPMJ-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(2-ethoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN(C)C)=CC=1)N2 DRZJFVDIROQPMJ-UHFFFAOYSA-N 0.000 claims 1
RXLQUQJNVGSPGB-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(2-methylbutan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)(C)CC)=CC=NC=2NC=1C1=CC=C(NCCN(C)C)C=C1 RXLQUQJNVGSPGB-UHFFFAOYSA-N 0.000 claims 1
DLOHIVZMHMQNOG-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(3,3,5-trimethylcyclohexyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN(C)C)=CC=1)N2 DLOHIVZMHMQNOG-UHFFFAOYSA-N 0.000 claims 1
CULWXYUOQAZHRY-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(4,4-dimethylpentan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(CC(C)(C)C)C)=CC=NC=2NC=1C1=CC=C(NCCN(C)C)C=C1 CULWXYUOQAZHRY-UHFFFAOYSA-N 0.000 claims 1
RELPDTIIYVWXGW-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 RELPDTIIYVWXGW-UHFFFAOYSA-N 0.000 claims 1
UPUQEEDJXNBQSE-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(5-methylhexan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)CCC(C)C)=CC=NC=2NC=1C1=CC=C(NCCN(C)C)C=C1 UPUQEEDJXNBQSE-UHFFFAOYSA-N 0.000 claims 1
FFILPPXGANINRS-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-[1-(dimethylamino)propan-2-yl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(CN(C)C)C)=CC=NC=2NC=1C1=CC=C(NCCN(C)C)C=C1 FFILPPXGANINRS-UHFFFAOYSA-N 0.000 claims 1
XZYOOFGRGZVPBB-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-[1-(hydroxymethyl)cyclopentyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC3(CO)CCCC3)C=CN=C2N1 XZYOOFGRGZVPBB-UHFFFAOYSA-N 0.000 claims 1
FFIFZJSASKFLOP-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-pentan-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(CC)CC)=CC=NC=2NC=1C1=CC=C(NCCN(C)C)C=C1 FFIFZJSASKFLOP-UHFFFAOYSA-N 0.000 claims 1
IDKADBSXCTXJRM-UHFFFAOYSA-N 2-[4-[2-[(2-phenyl-1h-imidazo[4,5-b]pyridine-7-carbonyl)amino]ethyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 IDKADBSXCTXJRM-UHFFFAOYSA-N 0.000 claims 1
ICBVWCRVJUQMQK-UHFFFAOYSA-N 2-[4-[2-[[2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]ethyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(Cl)=CC=1)Cl)N2 ICBVWCRVJUQMQK-UHFFFAOYSA-N 0.000 claims 1
JOBGMYARAOUHMX-UHFFFAOYSA-N 2-[4-[3-(4-methylpiperazin-1-yl)propylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1CN(C)CCN1CCCNC1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 JOBGMYARAOUHMX-UHFFFAOYSA-N 0.000 claims 1
AYILHZSYWQDSNE-UHFFFAOYSA-N 2-[4-[3-(diethylamino)pyrrolidin-1-yl]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1C(N(CC)CC)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 AYILHZSYWQDSNE-UHFFFAOYSA-N 0.000 claims 1
NFSOWYJHVILDTE-UHFFFAOYSA-N 2-[4-[3-(diethylamino)pyrrolidin-1-yl]phenyl]-n-(4-ethylsulfanylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CC(CC1)N(CC)CC)N2 NFSOWYJHVILDTE-UHFFFAOYSA-N 0.000 claims 1
BCHUWZFASZPKOP-UHFFFAOYSA-N 2-[4-[3-(diethylamino)pyrrolidin-1-yl]phenyl]-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1C(N(CC)CC)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC(C)=CC=2)C=C1 BCHUWZFASZPKOP-UHFFFAOYSA-N 0.000 claims 1
WLKFYKGSAFDUMK-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)propylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCCN(C)C)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 WLKFYKGSAFDUMK-UHFFFAOYSA-N 0.000 claims 1
DIKLPGIYMYKXIZ-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)propylamino]phenyl]-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 DIKLPGIYMYKXIZ-UHFFFAOYSA-N 0.000 claims 1
GCKOJSNQSUQTFR-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)butylamino]phenyl]-n-(4-ethoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCCCN(C)C)=CC=1)N2 GCKOJSNQSUQTFR-UHFFFAOYSA-N 0.000 claims 1
FXIAQLUMIVMDGX-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)butylamino]phenyl]-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 FXIAQLUMIVMDGX-UHFFFAOYSA-N 0.000 claims 1
JFFOUICIRBXFRC-UHFFFAOYSA-N 2-aminocyclopentan-1-ol Chemical compound NC1CCCC1O JFFOUICIRBXFRC-UHFFFAOYSA-N 0.000 claims 1
YVDIFVFOIUNCBL-UHFFFAOYSA-N 2-cyclopropyl-n-[2-(3-hydroxyphenyl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2CC2)=C1 YVDIFVFOIUNCBL-UHFFFAOYSA-N 0.000 claims 1
LSUFXKMMAVAXDP-UHFFFAOYSA-N 2-cyclopropyl-n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1CC1)N2 LSUFXKMMAVAXDP-UHFFFAOYSA-N 0.000 claims 1
BYXZXCSIHGBYHK-UHFFFAOYSA-N 2-cyclopropyl-n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1CC1)N2 BYXZXCSIHGBYHK-UHFFFAOYSA-N 0.000 claims 1
UQTAKGVBPAMBRQ-UHFFFAOYSA-N 2-phenyl-n-(2-pyridin-2-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CC=N1 UQTAKGVBPAMBRQ-UHFFFAOYSA-N 0.000 claims 1
KHGBMZXJOZRSKB-UHFFFAOYSA-N 2-phenyl-n-(2-pyridin-3-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CN=C1 KHGBMZXJOZRSKB-UHFFFAOYSA-N 0.000 claims 1
BQXBGBRTZUBLIX-UHFFFAOYSA-N 2-phenyl-n-(2-pyridin-4-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NCCC1=CC=NC=C1 BQXBGBRTZUBLIX-UHFFFAOYSA-N 0.000 claims 1
HVLREFAGUFBFFH-UHFFFAOYSA-N 2-phenyl-n-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NC(C=C1)=CC=C1N1CCCCC1 HVLREFAGUFBFFH-UHFFFAOYSA-N 0.000 claims 1
NAHHNSMHYCLMON-UHFFFAOYSA-N 2-pyridin-3-ylethanamine Chemical compound NCCC1=CC=CN=C1 NAHHNSMHYCLMON-UHFFFAOYSA-N 0.000 claims 1
XTWXMYKEBXIAMF-UHFFFAOYSA-N 2-thiophen-2-yl-n-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 XTWXMYKEBXIAMF-UHFFFAOYSA-N 0.000 claims 1
FHQRLGOEFMJXHW-UHFFFAOYSA-N 2-thiophen-3-yl-n-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 FHQRLGOEFMJXHW-UHFFFAOYSA-N 0.000 claims 1
NITIVZUQNQWBCD-UHFFFAOYSA-N 3-[[2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]bicyclo[2.2.1]heptane-3-carboxylic acid Chemical compound C1C(C2)CCC2C1(C(=O)O)NC(=O)C(C=1N=2)=CC=NC=1NC=2C1=CC=C(F)C=C1 NITIVZUQNQWBCD-UHFFFAOYSA-N 0.000 claims 1
XAVBRZMHQJCGDI-UHFFFAOYSA-N 4,4-dimethylpentan-2-amine Chemical compound CC(N)CC(C)(C)C XAVBRZMHQJCGDI-UHFFFAOYSA-N 0.000 claims 1
XHEMFRKTOJUJJX-UHFFFAOYSA-N 4-ethoxypyridin-3-amine Chemical compound CCOC1=CC=NC=C1N XHEMFRKTOJUJJX-UHFFFAOYSA-N 0.000 claims 1
IBKMZYWDWWIWEL-UHFFFAOYSA-N 4-methylpyridin-3-amine Chemical compound CC1=CC=NC=C1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 claims 1
ZTNMFJQPMDLSSK-UHFFFAOYSA-N 6-bromo-2-(3-fluorophenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=C(Br)C=NC2=C1N=C(C=1C=C(F)C=CC=1)N2 ZTNMFJQPMDLSSK-UHFFFAOYSA-N 0.000 claims 1
ONAYKSLRQUVXKU-UHFFFAOYSA-N 6-bromo-2-(3-methoxyphenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(C=2NC3=NC=C(Br)C(C(=O)NC=4C(=CC=NC=4)C)=C3N=2)=C1 ONAYKSLRQUVXKU-UHFFFAOYSA-N 0.000 claims 1
YQGMWHXDWKFMQS-UHFFFAOYSA-N 6-bromo-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1C=2C(C(=O)O)=C(Br)C=NC=2N=C1C=1C=COC=1 YQGMWHXDWKFMQS-UHFFFAOYSA-N 0.000 claims 1
URTFOBNIBGQKHS-UHFFFAOYSA-N 6-bromo-2-phenyl-n-(2-thiophen-2-ylethyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound BrC1=CN=C2NC(C=3C=CC=CC=3)=NC2=C1C(=O)NCCC1=CC=CS1 URTFOBNIBGQKHS-UHFFFAOYSA-N 0.000 claims 1
QXWRNQKUEPFKGG-UHFFFAOYSA-N 6-bromo-n-(4-ethoxy-6-methylpyridin-3-yl)-2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class CCOC1=CC(C)=NC=C1NC(=O)C1=C(Br)C=NC2=C1N=C(C=1C=C(F)C=CC=1)N2 QXWRNQKUEPFKGG-UHFFFAOYSA-N 0.000 claims 1
VTLCZFRTEHOXRU-UHFFFAOYSA-N 6-bromo-n-[2-(2-chloropyridin-4-yl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(F)=CC=C1C(NC1=NC=C2Br)=NC1=C2C(=O)NCCC1=CC=NC(Cl)=C1 VTLCZFRTEHOXRU-UHFFFAOYSA-N 0.000 claims 1
FNCJUURHSISAEB-UHFFFAOYSA-N 6-bromo-n-[2-(2-chloropyridin-4-yl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2Br)C=2C=CC=CC=2)=C1 FNCJUURHSISAEB-UHFFFAOYSA-N 0.000 claims 1
ZIGDNQOAGUFKQX-UHFFFAOYSA-N 6-bromo-n-[2-(2-chloropyridin-4-yl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2Br)C2=CSC=C2)=C1 ZIGDNQOAGUFKQX-UHFFFAOYSA-N 0.000 claims 1
MCYRFJLKOBTLCI-UHFFFAOYSA-N 6-chloro-2-phenyl-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=CC=C1)C(=O)O MCYRFJLKOBTLCI-UHFFFAOYSA-N 0.000 claims 1
VSBISZPNLZFTPG-UHFFFAOYSA-N 6-chloro-5-methylpyridin-3-amine Chemical compound CC1=CC(N)=CN=C1Cl VSBISZPNLZFTPG-UHFFFAOYSA-N 0.000 claims 1
PSNIBCMODLHKHE-UHFFFAOYSA-N 6-chloro-n-[2-(2-chloropyridin-4-yl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(F)=CC=C1C(NC1=NC=C2Cl)=NC1=C2C(=O)NCCC1=CC=NC(Cl)=C1 PSNIBCMODLHKHE-UHFFFAOYSA-N 0.000 claims 1
HIQHEVILHKLVDP-UHFFFAOYSA-N [2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridin-7-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)N3CCCCC3)C=CN=C2N1 HIQHEVILHKLVDP-UHFFFAOYSA-N 0.000 claims 1
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 1
UGVFOBZKKJNIBX-UHFFFAOYSA-N n,2-diphenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NC1=CC=CC=C1 UGVFOBZKKJNIBX-UHFFFAOYSA-N 0.000 claims 1
BOUDMRIVTUEUPO-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4OCOC4=CC=3)C=CN=C2N1 BOUDMRIVTUEUPO-UHFFFAOYSA-N 0.000 claims 1
JCEFBHJSHKPQJC-UHFFFAOYSA-N n-(1-adamantyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC34CC5CC(CC(C5)C3)C4)C=CN=C2N1 JCEFBHJSHKPQJC-UHFFFAOYSA-N 0.000 claims 1
DZCGRPVBKNWNTK-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=C(C(=O)NC4C5CCN(CC5)C4)C=CN=C3N=2)C=C1 DZCGRPVBKNWNTK-UHFFFAOYSA-N 0.000 claims 1
JKVIBCKDHIHMRV-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CCN(CC=4C=CC=CC=4)CC3)C=CN=C2N1 JKVIBCKDHIHMRV-UHFFFAOYSA-N 0.000 claims 1
CCUBOAKNLVLYBQ-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CN(CC=4C=CC=CC=4)CC3)C=CN=C2N1 CCUBOAKNLVLYBQ-UHFFFAOYSA-N 0.000 claims 1
NSXUCGQZUUDOOD-UHFFFAOYSA-N n-(2,5-dichloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=NC=C(Cl)C=3)Cl)C=CN=C2N1 NSXUCGQZUUDOOD-UHFFFAOYSA-N 0.000 claims 1
DBMKPFVROMAHHJ-UHFFFAOYSA-N n-(2,6-diethylphenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 DBMKPFVROMAHHJ-UHFFFAOYSA-N 0.000 claims 1
YXCHAYPSARRAFZ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 YXCHAYPSARRAFZ-UHFFFAOYSA-N 0.000 claims 1
LFWYBBUTCBDHHF-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-morpholin-4-ylethylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class CC1=CC=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN3CCOCC3)=CC=1)N2 LFWYBBUTCBDHHF-UHFFFAOYSA-N 0.000 claims 1
BGEYPWBJQYWSAH-UHFFFAOYSA-N n-(2,6-dimethylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 BGEYPWBJQYWSAH-UHFFFAOYSA-N 0.000 claims 1
GMCVEGRQDRKGJC-UHFFFAOYSA-N n-(2-adamantyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3C4CC5CC(C4)CC3C5)C=CN=C2N1 GMCVEGRQDRKGJC-UHFFFAOYSA-N 0.000 claims 1
RLNLUWXYIMVEEC-UHFFFAOYSA-N n-(2-adamantyl)-2-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1C2CC(C3)CC1CC3C2NC(=O)C(C=1N=2)=CC=NC=1NC=2C(C=C1)=CC=C1N1CCOCC1 RLNLUWXYIMVEEC-UHFFFAOYSA-N 0.000 claims 1
PJJHWMIDAKDFOR-UHFFFAOYSA-N n-(2-adamantyl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC2C3CC4CC(C3)CC2C4)C=C1 PJJHWMIDAKDFOR-UHFFFAOYSA-N 0.000 claims 1
OKHUCQDXAQWPBU-UHFFFAOYSA-N n-(2-chloro-4-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC(Cl)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OKHUCQDXAQWPBU-UHFFFAOYSA-N 0.000 claims 1
LPSIOVICRJEOTO-UHFFFAOYSA-N n-(2-chloro-5-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CN=C(Cl)C(NC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 LPSIOVICRJEOTO-UHFFFAOYSA-N 0.000 claims 1
RJCZUSAZDBTIAU-UHFFFAOYSA-N n-(2-chloro-6-methoxypyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=NC(OC)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 RJCZUSAZDBTIAU-UHFFFAOYSA-N 0.000 claims 1
FWDIHJDLMPCKSR-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=NC=CC=3)Cl)C=CN=C2N1 FWDIHJDLMPCKSR-UHFFFAOYSA-N 0.000 claims 1
VFKCPBVQOGPBTE-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-2-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=NC=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1N=CC=CC=1)N2 VFKCPBVQOGPBTE-UHFFFAOYSA-N 0.000 claims 1
VRUYJGSWNPMICG-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=NC=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 VRUYJGSWNPMICG-UHFFFAOYSA-N 0.000 claims 1
UQZOEVMGSBGAFC-UHFFFAOYSA-N n-(2-ethoxyphenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 UQZOEVMGSBGAFC-UHFFFAOYSA-N 0.000 claims 1
NZFIPRUIBTUBCN-UHFFFAOYSA-N n-(2-pyridin-2-ylethyl)-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CC=N1 NZFIPRUIBTUBCN-UHFFFAOYSA-N 0.000 claims 1
OWNDLJOJBHUSNP-UHFFFAOYSA-N n-(2-pyridin-2-ylethyl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CSC=C3)=NC=2C=1C(=O)NCCC1=CC=CC=N1 OWNDLJOJBHUSNP-UHFFFAOYSA-N 0.000 claims 1
HEKFRQONKKSVIK-UHFFFAOYSA-N n-(2-pyridin-3-ylethyl)-2-[4-(3-pyrrolidin-1-ylpropylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(NCCCN4CCCC4)=CC=3)=NC=2C=1C(=O)NCCC1=CC=CN=C1 HEKFRQONKKSVIK-UHFFFAOYSA-N 0.000 claims 1
GKVIBNKRSVBNHK-UHFFFAOYSA-N n-(2-pyridin-3-ylethyl)-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NCCC1=CC=CN=C1 GKVIBNKRSVBNHK-UHFFFAOYSA-N 0.000 claims 1
AZLAHEXYOHKDHG-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NCCC1=CC=NC=C1 AZLAHEXYOHKDHG-UHFFFAOYSA-N 0.000 claims 1
XRNURYUGUIBFJZ-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CSC=C3)=NC=2C=1C(=O)NCCC1=CC=NC=C1 XRNURYUGUIBFJZ-UHFFFAOYSA-N 0.000 claims 1
GZDTVDMLXOLBTK-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC(OC)=CC(NC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 GZDTVDMLXOLBTK-UHFFFAOYSA-N 0.000 claims 1
PRWKGZSVRHSEDV-UHFFFAOYSA-N n-(3-acetamidophenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC(=O)NC1=CC=CC(NC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 PRWKGZSVRHSEDV-UHFFFAOYSA-N 0.000 claims 1
XMOSXLIJHFDDTG-UHFFFAOYSA-N n-(3-aminocyclohexyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1C(N)CCCC1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 XMOSXLIJHFDDTG-UHFFFAOYSA-N 0.000 claims 1
BJKZHDSHGCGZEX-UHFFFAOYSA-N n-(3-aminocyclohexyl)-2-[4-[2-(dimethylamino)ethylamino]phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC3CC(N)CCC3)C=CN=C2N1 BJKZHDSHGCGZEX-UHFFFAOYSA-N 0.000 claims 1
BDINYSCMWNVRTM-UHFFFAOYSA-N n-(3-cyanophenyl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C(C=CC=3)C#N)C=CN=C2N1 BDINYSCMWNVRTM-UHFFFAOYSA-N 0.000 claims 1
ABJPWSCXORJWGM-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC=CC=3)=NC=2C=1C(=O)NCCCN1CCOCC1 ABJPWSCXORJWGM-UHFFFAOYSA-N 0.000 claims 1
IIDYSIAWQFUYJF-UHFFFAOYSA-N n-(3-pyridin-3-ylpropyl)-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NCCCC1=CC=CN=C1 IIDYSIAWQFUYJF-UHFFFAOYSA-N 0.000 claims 1
XQDIDCJBIBVXBY-UHFFFAOYSA-N n-(3-pyridin-3-ylpropyl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CSC=C3)=NC=2C=1C(=O)NCCCC1=CC=CN=C1 XQDIDCJBIBVXBY-UHFFFAOYSA-N 0.000 claims 1
CZYCNUUEYDDHTE-UHFFFAOYSA-N n-(3-pyridin-4-ylpropyl)-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NCCCC1=CC=NC=C1 CZYCNUUEYDDHTE-UHFFFAOYSA-N 0.000 claims 1
MCJXHQJWKAGVNT-UHFFFAOYSA-N n-(3-pyridin-4-ylpropyl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CSC=C3)=NC=2C=1C(=O)NCCCC1=CC=NC=C1 MCJXHQJWKAGVNT-UHFFFAOYSA-N 0.000 claims 1
GXLCZHKVPIZVII-UHFFFAOYSA-N n-(4,6-dichloropyrimidin-5-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=NC=NC=3Cl)Cl)C=CN=C2N1 GXLCZHKVPIZVII-UHFFFAOYSA-N 0.000 claims 1
FABYPTROSNLQQN-UHFFFAOYSA-N n-(4,6-dimethylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 FABYPTROSNLQQN-UHFFFAOYSA-N 0.000 claims 1
LNMOEAJOLNDOBC-UHFFFAOYSA-N n-(4,6-dimethylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 LNMOEAJOLNDOBC-UHFFFAOYSA-N 0.000 claims 1
CSOLAVAFEHRDBI-UHFFFAOYSA-N n-(4,6-dimethylpyridin-3-yl)-2-(4-pyrrolidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCC1)N2 CSOLAVAFEHRDBI-UHFFFAOYSA-N 0.000 claims 1
KBBGDYPMHVMWAB-UHFFFAOYSA-N n-(4,6-dimethylpyridin-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C(=CC(C)=NC=2)C)C=C1 KBBGDYPMHVMWAB-UHFFFAOYSA-N 0.000 claims 1
XAVIZACPQWYGPG-UHFFFAOYSA-N n-(4-benzamidophenyl)-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1NC(=O)C(C=1N=2)=CC=NC=1NC=2C=1C=COC=1 XAVIZACPQWYGPG-UHFFFAOYSA-N 0.000 claims 1
HZYBFPVIEVVYAE-UHFFFAOYSA-N n-(4-benzamidophenyl)-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1NC(=O)C(C=1N=2)=CC=NC=1NC=2C1=CC=CC=C1 HZYBFPVIEVVYAE-UHFFFAOYSA-N 0.000 claims 1
PIGQPMRAMXUTER-UHFFFAOYSA-N n-(4-benzamidophenyl)-6-bromo-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound BrC1=CN=C2NC(C=3C=CC=CC=3)=NC2=C1C(=O)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 PIGQPMRAMXUTER-UHFFFAOYSA-N 0.000 claims 1
UZWOFJUJQLOLCY-UHFFFAOYSA-N n-(4-chloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)Cl)C=CN=C2N1 UZWOFJUJQLOLCY-UHFFFAOYSA-N 0.000 claims 1
YSLWPFDUJHOPST-UHFFFAOYSA-N n-(4-ethoxy-6-methylpyridin-3-yl)-2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC(C)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(F)C=CC=1)N2 YSLWPFDUJHOPST-UHFFFAOYSA-N 0.000 claims 1
HKHOYPXHOPLHBH-UHFFFAOYSA-N n-(4-ethoxy-6-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC(C)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 HKHOYPXHOPLHBH-UHFFFAOYSA-N 0.000 claims 1
PWBRCCIFKUSMBJ-UHFFFAOYSA-N n-(4-ethoxy-6-methylpyridin-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC(C)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCN(C)CC1)N2 PWBRCCIFKUSMBJ-UHFFFAOYSA-N 0.000 claims 1
KXUUYDDJRABLCN-UHFFFAOYSA-N n-(4-ethoxy-6-methylpyridin-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC(C)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 KXUUYDDJRABLCN-UHFFFAOYSA-N 0.000 claims 1
SANLYIPIWADLOQ-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(F)C=CC=1)N2 SANLYIPIWADLOQ-UHFFFAOYSA-N 0.000 claims 1
QXCOTWZYCWZZEI-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(3-methoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(OC)C=CC=1)N2 QXCOTWZYCWZZEI-UHFFFAOYSA-N 0.000 claims 1
KONUVNNRPCDKBD-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 KONUVNNRPCDKBD-UHFFFAOYSA-N 0.000 claims 1
RJZZVNXEGMOBLM-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(4-pyrrolidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCC1)N2 RJZZVNXEGMOBLM-UHFFFAOYSA-N 0.000 claims 1
AQTIVJLBQUPKOB-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCN(C)CC1)N2 AQTIVJLBQUPKOB-UHFFFAOYSA-N 0.000 claims 1
VDJAUUNPSCVECS-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1N=CC=CC=1)N2 VDJAUUNPSCVECS-UHFFFAOYSA-N 0.000 claims 1
AWRGNBUVZZRABP-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 AWRGNBUVZZRABP-UHFFFAOYSA-N 0.000 claims 1
BIBWWLFNXJSWMW-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CN=CC=1)N2 BIBWWLFNXJSWMW-UHFFFAOYSA-N 0.000 claims 1
XCBKVDKXNJJFAG-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 XCBKVDKXNJJFAG-UHFFFAOYSA-N 0.000 claims 1
MKTCKWVSLVOXFM-UHFFFAOYSA-N n-(4-ethylsulfanyl-6-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC(C)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 MKTCKWVSLVOXFM-UHFFFAOYSA-N 0.000 claims 1
RTGXWCOKEBMSHL-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(F)C=CC=1)N2 RTGXWCOKEBMSHL-UHFFFAOYSA-N 0.000 claims 1
HOVYCEVWMLDTLX-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 HOVYCEVWMLDTLX-UHFFFAOYSA-N 0.000 claims 1
WVHOTCAPLQWTPI-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 WVHOTCAPLQWTPI-UHFFFAOYSA-N 0.000 claims 1
OUTVKJDVYXIFFV-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-(4-pyrrolidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCC1)N2 OUTVKJDVYXIFFV-UHFFFAOYSA-N 0.000 claims 1
LWJUUGMIJCFBQU-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCN(C)CC1)N2 LWJUUGMIJCFBQU-UHFFFAOYSA-N 0.000 claims 1
WHDZQAVEGOPYDQ-UHFFFAOYSA-N n-(4-ethylsulfanylpyridin-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 WHDZQAVEGOPYDQ-UHFFFAOYSA-N 0.000 claims 1
VILVOBGLGPSMAH-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)-2-[4-(2-morpholin-4-ylethylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1CC(O)CCC1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN3CCOCC3)=CC=1)N2 VILVOBGLGPSMAH-UHFFFAOYSA-N 0.000 claims 1
QLQGELDYENXNOJ-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCOCC1)N2 QLQGELDYENXNOJ-UHFFFAOYSA-N 0.000 claims 1
SFZKLLFYZVCCKG-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 SFZKLLFYZVCCKG-UHFFFAOYSA-N 0.000 claims 1
GYBBOCAZYPZDJD-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-[4-(2-morpholin-4-ylethylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN3CCOCC3)=CC=1)N2 GYBBOCAZYPZDJD-UHFFFAOYSA-N 0.000 claims 1
HSCUGKKDVRFVTB-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-[4-(3-pyrrolidin-1-ylpropylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCCN3CCCC3)=CC=1)N2 HSCUGKKDVRFVTB-UHFFFAOYSA-N 0.000 claims 1
VFERNPYCXMFETK-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1N=CC=CC=1)N2 VFERNPYCXMFETK-UHFFFAOYSA-N 0.000 claims 1
GEAYIBAWLHKTSY-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 GEAYIBAWLHKTSY-UHFFFAOYSA-N 0.000 claims 1
RZINWQFCBHNFHO-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CN=CC=1)N2 RZINWQFCBHNFHO-UHFFFAOYSA-N 0.000 claims 1
CHKSEMFNPTXEIK-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1N=C(C)C=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 CHKSEMFNPTXEIK-UHFFFAOYSA-N 0.000 claims 1
HBZKSGZWXGZKGL-UHFFFAOYSA-N n-(6-acetamidopyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NC(=O)C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 HBZKSGZWXGZKGL-UHFFFAOYSA-N 0.000 claims 1
WMUNTSNHSGIFTB-UHFFFAOYSA-N n-(6-chloro-4-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC(Cl)=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 WMUNTSNHSGIFTB-UHFFFAOYSA-N 0.000 claims 1
MUEZNHNQLOPZND-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(Cl)=CC=3)C=CN=C2N1 MUEZNHNQLOPZND-UHFFFAOYSA-N 0.000 claims 1
DXGDWEHQDPWOEH-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 DXGDWEHQDPWOEH-UHFFFAOYSA-N 0.000 claims 1
IVIFFFJHOAWHTN-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 IVIFFFJHOAWHTN-UHFFFAOYSA-N 0.000 claims 1
XCUZDMXYUPDSKY-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-(4-pyrrolidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCC1)N2 XCUZDMXYUPDSKY-UHFFFAOYSA-N 0.000 claims 1
LXNUFXZGANZLRZ-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-[4-(4-methylpiperazin-1-yl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCN(C)CC1)N2 LXNUFXZGANZLRZ-UHFFFAOYSA-N 0.000 claims 1
UYWQNOIDIQLCOK-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 UYWQNOIDIQLCOK-UHFFFAOYSA-N 0.000 claims 1
WFSZOABEEDLRRK-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 WFSZOABEEDLRRK-UHFFFAOYSA-N 0.000 claims 1
JWMXCGAAUZSCSL-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 JWMXCGAAUZSCSL-UHFFFAOYSA-N 0.000 claims 1
KLYUMNUQXBHAIT-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-(4-pyrrolidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCC1)N2 KLYUMNUQXBHAIT-UHFFFAOYSA-N 0.000 claims 1
RJILDFIPBLVLBD-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1N=CC=CC=1)N2 RJILDFIPBLVLBD-UHFFFAOYSA-N 0.000 claims 1
ZUECFQPFZZLCTO-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 ZUECFQPFZZLCTO-UHFFFAOYSA-N 0.000 claims 1
LNKZASDQNDRGFQ-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CN=CC=1)N2 LNKZASDQNDRGFQ-UHFFFAOYSA-N 0.000 claims 1
GMCJZWOHTPRAQL-UHFFFAOYSA-N n-[1-(dimethylamino)propan-2-yl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(CN(C)C)C)=CC=NC=2NC=1C1=CC=C(F)C=C1 GMCJZWOHTPRAQL-UHFFFAOYSA-N 0.000 claims 1
XYQFKRRGCIGCBM-UHFFFAOYSA-N n-[2,6-di(propan-2-yl)phenyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 XYQFKRRGCIGCBM-UHFFFAOYSA-N 0.000 claims 1
YDJPHOZYLLTYGK-UHFFFAOYSA-N n-[2-(2-chloropyridin-3-yl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C(=NC=CC=3)Cl)C=CN=C2N1 YDJPHOZYLLTYGK-UHFFFAOYSA-N 0.000 claims 1
SDMDKCQMMFZDIF-UHFFFAOYSA-N n-[2-(2-chloropyridin-3-yl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 SDMDKCQMMFZDIF-UHFFFAOYSA-N 0.000 claims 1
LZEOTCSAIRQNRZ-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=C(Cl)N=CC=3)C=CN=C2N1 LZEOTCSAIRQNRZ-UHFFFAOYSA-N 0.000 claims 1
UWPWNFNXUJBLRN-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2OC=CC=2)=C1 UWPWNFNXUJBLRN-UHFFFAOYSA-N 0.000 claims 1
CMMAUDPSHAAYJH-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=COC=C2)=C1 CMMAUDPSHAAYJH-UHFFFAOYSA-N 0.000 claims 1
DPGPFEFQJCVZQZ-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 DPGPFEFQJCVZQZ-UHFFFAOYSA-N 0.000 claims 1
WZZKXOQYMWWENO-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 WZZKXOQYMWWENO-UHFFFAOYSA-N 0.000 claims 1
RSABWBNYESUOEQ-UHFFFAOYSA-N n-[2-(2-chloropyridin-4-yl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 RSABWBNYESUOEQ-UHFFFAOYSA-N 0.000 claims 1
AWFPSHWTHAZXQE-UHFFFAOYSA-N n-[2-(2-fluoropyridin-4-yl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(F)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 AWFPSHWTHAZXQE-UHFFFAOYSA-N 0.000 claims 1
QMGVGMGOOCHFGY-UHFFFAOYSA-N n-[2-(2-hydroxyphenyl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 QMGVGMGOOCHFGY-UHFFFAOYSA-N 0.000 claims 1
OATNLZDGRBLRGE-UHFFFAOYSA-N n-[2-(2-hydroxyphenyl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 OATNLZDGRBLRGE-UHFFFAOYSA-N 0.000 claims 1
KDFJBTWXHJHAMW-UHFFFAOYSA-N n-[2-(2-hydroxyphenyl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 KDFJBTWXHJHAMW-UHFFFAOYSA-N 0.000 claims 1
KRJYSWQZBOPRIW-UHFFFAOYSA-N n-[2-(2-methylpyridin-3-yl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 KRJYSWQZBOPRIW-UHFFFAOYSA-N 0.000 claims 1
WALNBWHBGYMLPK-UHFFFAOYSA-N n-[2-(2-methylpyridin-3-yl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 WALNBWHBGYMLPK-UHFFFAOYSA-N 0.000 claims 1
AVJXAVCOFJDOGA-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=C(Cl)C=CC=3)C=CN=C2N1 AVJXAVCOFJDOGA-UHFFFAOYSA-N 0.000 claims 1
CKHGXVXWGWTMAZ-UHFFFAOYSA-N n-[2-(3-hydroxyphenyl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 CKHGXVXWGWTMAZ-UHFFFAOYSA-N 0.000 claims 1
NCUFSXVHHVVDEG-UHFFFAOYSA-N n-[2-(3-hydroxyphenyl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 NCUFSXVHHVVDEG-UHFFFAOYSA-N 0.000 claims 1
FEUGJYRGZOGDFH-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(Cl)=CC=1)Cl)N2 FEUGJYRGZOGDFH-UHFFFAOYSA-N 0.000 claims 1
VACCRPGXTDGQCE-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 VACCRPGXTDGQCE-UHFFFAOYSA-N 0.000 claims 1
JMILLZVIEOOIDX-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 JMILLZVIEOOIDX-UHFFFAOYSA-N 0.000 claims 1
MDBSPUAXTNFXCN-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 MDBSPUAXTNFXCN-UHFFFAOYSA-N 0.000 claims 1
WRUFYTBXUKXDEI-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 WRUFYTBXUKXDEI-UHFFFAOYSA-N 0.000 claims 1
AWOPDLAVFQFHCD-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 AWOPDLAVFQFHCD-UHFFFAOYSA-N 0.000 claims 1
DGUAGZVFTIQOBS-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 DGUAGZVFTIQOBS-UHFFFAOYSA-N 0.000 claims 1
BVTKSTVWSNIMLK-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2OC=CC=2)=C1 BVTKSTVWSNIMLK-UHFFFAOYSA-N 0.000 claims 1
WOKFTJKGYXDGTR-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=COC=C2)=C1 WOKFTJKGYXDGTR-UHFFFAOYSA-N 0.000 claims 1
BJWHKFRMXYKXLL-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 BJWHKFRMXYKXLL-UHFFFAOYSA-N 0.000 claims 1
RJXVMGOTHYEVPE-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 RJXVMGOTHYEVPE-UHFFFAOYSA-N 0.000 claims 1
UDOCVVBFQBPICG-UHFFFAOYSA-N n-[2-(4-fluoro-3-hydroxyphenyl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=C(F)C(O)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 UDOCVVBFQBPICG-UHFFFAOYSA-N 0.000 claims 1
WUGNXBSWEVYWPV-UHFFFAOYSA-N n-[2-(6-chloropyridin-3-yl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCC=3C=NC(Cl)=CC=3)C=CN=C2N1 WUGNXBSWEVYWPV-UHFFFAOYSA-N 0.000 claims 1
FBHGESQNMLQONL-UHFFFAOYSA-N n-[2-(6-chloropyridin-3-yl)ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 FBHGESQNMLQONL-UHFFFAOYSA-N 0.000 claims 1
CKBDQCDTXBFPAC-UHFFFAOYSA-N n-[2-(6-chloropyridin-3-yl)ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 CKBDQCDTXBFPAC-UHFFFAOYSA-N 0.000 claims 1
XSDPAGDUHADNHH-UHFFFAOYSA-N n-[2-(6-chloropyridin-3-yl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 XSDPAGDUHADNHH-UHFFFAOYSA-N 0.000 claims 1
AFKXRVDDQLVUHZ-UHFFFAOYSA-N n-[2-(6-chloropyridin-3-yl)ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 AFKXRVDDQLVUHZ-UHFFFAOYSA-N 0.000 claims 1
KWWSQEBWEYUCKG-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 KWWSQEBWEYUCKG-UHFFFAOYSA-N 0.000 claims 1
YGFAREWDQVCIIH-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 YGFAREWDQVCIIH-UHFFFAOYSA-N 0.000 claims 1
BFOGJCNRUDCCMC-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 BFOGJCNRUDCCMC-UHFFFAOYSA-N 0.000 claims 1
REGIMNBNZQBLAJ-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 REGIMNBNZQBLAJ-UHFFFAOYSA-N 0.000 claims 1
BHUXJUKSQPDHQR-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 BHUXJUKSQPDHQR-UHFFFAOYSA-N 0.000 claims 1
TZUJXEMVYKJCNS-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-3-yl]ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound NCC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 TZUJXEMVYKJCNS-UHFFFAOYSA-N 0.000 claims 1
KKAPSSBMQTWZQJ-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-4-yl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 KKAPSSBMQTWZQJ-UHFFFAOYSA-N 0.000 claims 1
PARLZSDDMYPHFZ-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-4-yl]ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=COC=C2)=C1 PARLZSDDMYPHFZ-UHFFFAOYSA-N 0.000 claims 1
ZYUZVQBMDRRSSP-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-4-yl]ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 ZYUZVQBMDRRSSP-UHFFFAOYSA-N 0.000 claims 1
ZROJYFAEJLPIAW-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-4-yl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 ZROJYFAEJLPIAW-UHFFFAOYSA-N 0.000 claims 1
LOITWOBTCDYXGB-UHFFFAOYSA-N n-[2-[2-(methylamino)pyridin-4-yl]ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NC)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 LOITWOBTCDYXGB-UHFFFAOYSA-N 0.000 claims 1
ZTIRUECFCOIXLA-UHFFFAOYSA-N n-[2-[3-[2-(dimethylamino)ethoxy]phenyl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class CN(C)CCOC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 ZTIRUECFCOIXLA-UHFFFAOYSA-N 0.000 claims 1
FXRDEIDYLHYPRU-UHFFFAOYSA-N n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 FXRDEIDYLHYPRU-UHFFFAOYSA-N 0.000 claims 1
VXQCTPIPGDZHCL-UHFFFAOYSA-N n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 VXQCTPIPGDZHCL-UHFFFAOYSA-N 0.000 claims 1
VLGLRNGLXIKNGY-UHFFFAOYSA-N n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 VLGLRNGLXIKNGY-UHFFFAOYSA-N 0.000 claims 1
PCOUZWQMPOLWHU-UHFFFAOYSA-N n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 PCOUZWQMPOLWHU-UHFFFAOYSA-N 0.000 claims 1
GCZGDGYVEBPMFG-UHFFFAOYSA-N n-[2-[4-(dimethylsulfamoylamino)phenyl]ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)N(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 GCZGDGYVEBPMFG-UHFFFAOYSA-N 0.000 claims 1
PQIARJKZGNSQTI-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-(1-oxothiophen-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CS(=O)C=C1)N2 PQIARJKZGNSQTI-UHFFFAOYSA-N 0.000 claims 1
OFTLPBYNGGRVQM-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OFTLPBYNGGRVQM-UHFFFAOYSA-N 0.000 claims 1
UEPISACUDGRXJT-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-(4-fluorophenyl)-3-methylimidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2C UEPISACUDGRXJT-UHFFFAOYSA-N 0.000 claims 1
NLMCVNVRBPWZCG-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 NLMCVNVRBPWZCG-UHFFFAOYSA-N 0.000 claims 1
NSSKRYTXKRSSHN-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 NSSKRYTXKRSSHN-UHFFFAOYSA-N 0.000 claims 1
JLMLOAXSQPVMKQ-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 JLMLOAXSQPVMKQ-UHFFFAOYSA-N 0.000 claims 1
WYQFGFSCDJKYOY-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 WYQFGFSCDJKYOY-UHFFFAOYSA-N 0.000 claims 1
LXZKEEJUQCASDL-UHFFFAOYSA-N n-[2-[4-(methanesulfonamido)phenyl]ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 LXZKEEJUQCASDL-UHFFFAOYSA-N 0.000 claims 1
OALFZNFPYZQTDF-UHFFFAOYSA-N n-[2-[4-(methanesulfonamido)phenyl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 OALFZNFPYZQTDF-UHFFFAOYSA-N 0.000 claims 1
XATKMURPPHAPKO-UHFFFAOYSA-N n-[2-[4-(methanesulfonamido)phenyl]ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 XATKMURPPHAPKO-UHFFFAOYSA-N 0.000 claims 1
XVMSIYRNOSRUEM-UHFFFAOYSA-N n-[2-[4-[[2-(4-ethylpiperazin-1-yl)acetyl]amino]phenyl]ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(CC)CCN1CC(=O)NC(C=C1)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 XVMSIYRNOSRUEM-UHFFFAOYSA-N 0.000 claims 1
IHQNWIBBCHBIEY-UHFFFAOYSA-N n-[2-[4-[[2-(dimethylamino)acetyl]amino]phenyl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical class C1=CC(NC(=O)CN(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 IHQNWIBBCHBIEY-UHFFFAOYSA-N 0.000 claims 1
ZHOOEPBELBZFIQ-UHFFFAOYSA-N n-[2-[4-[[2-(dimethylamino)acetyl]amino]phenyl]ethyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 ZHOOEPBELBZFIQ-UHFFFAOYSA-N 0.000 claims 1
LTVOQLSJNSYQHZ-UHFFFAOYSA-N n-[2-[4-[[2-(dimethylamino)acetyl]amino]phenyl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 LTVOQLSJNSYQHZ-UHFFFAOYSA-N 0.000 claims 1
ZYMLSQJXSVTVAO-UHFFFAOYSA-N n-[2-[6-(aminomethyl)pyridin-3-yl]ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 ZYMLSQJXSVTVAO-UHFFFAOYSA-N 0.000 claims 1
OVACBTGBDBACDQ-UHFFFAOYSA-N n-[3-(2-chloropyridin-4-yl)propyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCCC=3C=C(Cl)N=CC=3)C=CN=C2N1 OVACBTGBDBACDQ-UHFFFAOYSA-N 0.000 claims 1
ZANFYENAQDQFEM-UHFFFAOYSA-N n-[3-(2-chloropyridin-4-yl)propyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 ZANFYENAQDQFEM-UHFFFAOYSA-N 0.000 claims 1
NJHDMQKTYOFSJO-UHFFFAOYSA-N n-[3-(2-chloropyridin-4-yl)propyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC(CCCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 NJHDMQKTYOFSJO-UHFFFAOYSA-N 0.000 claims 1
SITMZFLQLMDVHL-UHFFFAOYSA-N n-[3-(2-fluoropyridin-3-yl)propyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound FC1=NC=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 SITMZFLQLMDVHL-UHFFFAOYSA-N 0.000 claims 1
WDNPVLXOVPGOHN-UHFFFAOYSA-N n-[3-(2-fluoropyridin-3-yl)propyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound FC1=NC=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 WDNPVLXOVPGOHN-UHFFFAOYSA-N 0.000 claims 1
PRMIUWPTXICFLU-UHFFFAOYSA-N n-[3-(6-chloropyridin-3-yl)propyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NCCCC=3C=NC(Cl)=CC=3)C=CN=C2N1 PRMIUWPTXICFLU-UHFFFAOYSA-N 0.000 claims 1
COJPTJYDHOPNFB-UHFFFAOYSA-N n-[3-(6-chloropyridin-3-yl)propyl]-2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C=1OC=CC=1)N2 COJPTJYDHOPNFB-UHFFFAOYSA-N 0.000 claims 1
OYPCRDXZGYJFNJ-UHFFFAOYSA-N n-[3-(6-chloropyridin-3-yl)propyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 OYPCRDXZGYJFNJ-UHFFFAOYSA-N 0.000 claims 1
APUSXTQYLYCKSA-UHFFFAOYSA-N n-[3-(6-chloropyridin-3-yl)propyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 APUSXTQYLYCKSA-UHFFFAOYSA-N 0.000 claims 1
QROVFQZSNWONAU-UHFFFAOYSA-N n-[3-(6-chloropyridin-3-yl)propyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 QROVFQZSNWONAU-UHFFFAOYSA-N 0.000 claims 1
YOCFNBGZNOEQQE-UHFFFAOYSA-N n-[3-(6-fluoropyridin-3-yl)propyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(F)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 YOCFNBGZNOEQQE-UHFFFAOYSA-N 0.000 claims 1
YFGGZUAXXDLFSS-UHFFFAOYSA-N n-[3-(6-fluoropyridin-3-yl)propyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(F)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 YFGGZUAXXDLFSS-UHFFFAOYSA-N 0.000 claims 1
FYTNANYDIOUPOS-UHFFFAOYSA-N n-[3-[6-(methanesulfonamido)pyridin-3-yl]propyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1CCCNC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 FYTNANYDIOUPOS-UHFFFAOYSA-N 0.000 claims 1
PQOZCVOJMUROIC-UHFFFAOYSA-N n-[4-(cyclopropylmethoxy)pyridin-3-yl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)OCC3CC3)C=CN=C2N1 PQOZCVOJMUROIC-UHFFFAOYSA-N 0.000 claims 1
QVUWLSHFWFLQOZ-UHFFFAOYSA-N n-[4-[2-(dimethylamino)ethoxy]pyridin-3-yl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CN(C)CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 QVUWLSHFWFLQOZ-UHFFFAOYSA-N 0.000 claims 1
JEKIQBATTBQYBD-UHFFFAOYSA-N n-[6-(dimethylamino)pyridin-3-yl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 JEKIQBATTBQYBD-UHFFFAOYSA-N 0.000 claims 1
CYSUTTFTMOPIFR-UHFFFAOYSA-N n-[6-(methylamino)pyridin-3-yl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NC)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 CYSUTTFTMOPIFR-UHFFFAOYSA-N 0.000 claims 1
SCLMBVCBYJJNSU-UHFFFAOYSA-N n-benzyl-n-ethyl-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(F)=CC=3)=NC=2C=1C(=O)N(CC)CC1=CC=CC=C1 SCLMBVCBYJJNSU-UHFFFAOYSA-N 0.000 claims 1
YPMCTRUWNKXUEX-UHFFFAOYSA-N n-cycloheptyl-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CCCCCC3)C=CN=C2N1 YPMCTRUWNKXUEX-UHFFFAOYSA-N 0.000 claims 1
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