JP2009523845A5 - - Google Patents

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Publication number

JP2009523845A5

JP2009523845A5 JP2008552225A JP2008552225A JP2009523845A5 JP 2009523845 A5 JP2009523845 A5 JP 2009523845A5 JP 2008552225 A JP2008552225 A JP 2008552225A JP 2008552225 A JP2008552225 A JP 2008552225A JP 2009523845 A5 JP2009523845 A5 JP 2009523845A5

Authority

JP

Japan

Prior art keywords

imidazo

pyridine

carboxylic acid

phenyl

amide

Prior art date

2007-01-23

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• -1 pyrrolidinylphenyl Chemical group 0.000 claims description 88
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 150000001875 compounds Chemical class 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 150000001408 amides Chemical class 0.000 claims description 17
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 102000001253 Protein Kinase Human genes 0.000 claims description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 150000004677 hydrates Chemical class 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 108060006633 protein kinase Proteins 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 3
• ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 2
• QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical group CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims description 2
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 125000004193 piperazinyl group Chemical group 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 238000007614 solvation Methods 0.000 claims description 2
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• 125000005425 toluyl group Chemical group 0.000 claims description 2
• DIEZPEIBLRSBCS-UHFFFAOYSA-N 2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(F)C=C1 DIEZPEIBLRSBCS-UHFFFAOYSA-N 0.000 claims 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
• 238000000034 method Methods 0.000 claims 8
• RPHWPBRVXJHHLL-UHFFFAOYSA-N 2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=COC=1 RPHWPBRVXJHHLL-UHFFFAOYSA-N 0.000 claims 7
• FEQIQCKIKLJLFO-UHFFFAOYSA-N 2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=CSC=1 FEQIQCKIKLJLFO-UHFFFAOYSA-N 0.000 claims 7
• 239000000203 mixture Substances 0.000 claims 7
• 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 6
• YTHVZLQCXJKFCN-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 YTHVZLQCXJKFCN-UHFFFAOYSA-N 0.000 claims 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
• 239000000126 substance Substances 0.000 claims 6
• 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 5
• FXLXAUUIWODDSG-UHFFFAOYSA-N 2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CS1 FXLXAUUIWODDSG-UHFFFAOYSA-N 0.000 claims 5
• CHXNAASGPJTHBO-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(Cl)C=C1 CHXNAASGPJTHBO-UHFFFAOYSA-N 0.000 claims 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
• 108091000080 Phosphotransferase Proteins 0.000 claims 4
• 239000003960 organic solvent Substances 0.000 claims 4
• 102000020233 phosphotransferase Human genes 0.000 claims 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
• ODJBWKPAXQTWRT-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 ODJBWKPAXQTWRT-UHFFFAOYSA-N 0.000 claims 3
• HQGXXVORJDZFLH-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound CN(CCN(C1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1)C)C HQGXXVORJDZFLH-UHFFFAOYSA-N 0.000 claims 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
• 238000010992 reflux Methods 0.000 claims 3
• VZWQWIABGPXJSY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(Cl)C=C1Cl VZWQWIABGPXJSY-UHFFFAOYSA-N 0.000 claims 2
• USLKSBWEDVVGFB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 USLKSBWEDVVGFB-UHFFFAOYSA-N 0.000 claims 2
• KCOHGYMERVIMPD-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(6-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(OC)=CC=3)C=CN=C2N1 KCOHGYMERVIMPD-UHFFFAOYSA-N 0.000 claims 2
• MEUCXTWWHIWTFZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(C)=CC=3)C=CN=C2N1 MEUCXTWWHIWTFZ-UHFFFAOYSA-N 0.000 claims 2
• MUFRLVBIHPTHDD-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1N1CCOCC1 MUFRLVBIHPTHDD-UHFFFAOYSA-N 0.000 claims 2
• MADDGOYCVBBCPW-UHFFFAOYSA-N 2-[4-(2-morpholin-4-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=C1NCCN1CCOCC1 MADDGOYCVBBCPW-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• RTGHKIIZLAVHKB-UHFFFAOYSA-N 2-cyclopropyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=NC=2N=C1C1CC1 RTGHKIIZLAVHKB-UHFFFAOYSA-N 0.000 claims 2
• IBKMZYWDWWIWEL-UHFFFAOYSA-N 4-methylpyridin-3-amine Chemical compound CC1=CC=NC=C1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 claims 2
• 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 claims 2
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims 2
• 102000001267 GSK3 Human genes 0.000 claims 2
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
• 108091008611 Protein Kinase B Proteins 0.000 claims 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims 2
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 2
• 239000004480 active ingredient Substances 0.000 claims 2
• 229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
• 239000003054 catalyst Substances 0.000 claims 2
• 239000007822 coupling agent Substances 0.000 claims 2
• 238000010438 heat treatment Methods 0.000 claims 2
• MQBDNSDYRHAIFK-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(OC)=CC=1)N2 MQBDNSDYRHAIFK-UHFFFAOYSA-N 0.000 claims 2
• XQZJTSNZNNCKSD-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-(4-pyrrolidin-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)N1CCCC1)N2 XQZJTSNZNNCKSD-UHFFFAOYSA-N 0.000 claims 2
• CWHPXAXQZKXBTI-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC(OC)=NC=3)C)C=CN=C2N1 CWHPXAXQZKXBTI-UHFFFAOYSA-N 0.000 claims 2
• RGRIWPWQUSKWLK-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 RGRIWPWQUSKWLK-UHFFFAOYSA-N 0.000 claims 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
• 150000007524 organic acids Chemical class 0.000 claims 2
• 239000007800 oxidant agent Substances 0.000 claims 2
• 239000002904 solvent Substances 0.000 claims 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
• RNJXYMFLEOXNBQ-UHFFFAOYSA-N 2-(1-oxothiophen-3-yl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=CS(=O)C=1 RNJXYMFLEOXNBQ-UHFFFAOYSA-N 0.000 claims 1
• WZBSPCUQEPLQEY-UHFFFAOYSA-N 2-(1-oxothiophen-3-yl)-n-(3-pyridin-3-ylpropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CS(=O)C=C3)=NC=2C=1C(=O)NCCCC1=CC=CN=C1 WZBSPCUQEPLQEY-UHFFFAOYSA-N 0.000 claims 1
• IEMWGGNELWEWIX-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-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(Cl)=CC=1)Cl)N2 IEMWGGNELWEWIX-UHFFFAOYSA-N 0.000 claims 1
• BDGAESRITDOUAO-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-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(Cl)=CC=2)Cl)=C1 BDGAESRITDOUAO-UHFFFAOYSA-N 0.000 claims 1
• RUELGHZBFJJFRS-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-[2-(4-sulfonylcyclohexa-1,5-dien-1-yl)ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC2=NC=CC(C(=O)NCCC=3C=CC(CC=3)=S(=O)=O)=C2N1 RUELGHZBFJJFRS-UHFFFAOYSA-N 0.000 claims 1
• FKEVBALJZQKULE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(F)C=C1F FKEVBALJZQKULE-UHFFFAOYSA-N 0.000 claims 1
• GOOXERMRDZVNAO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-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(F)=CC=1)F)N2 GOOXERMRDZVNAO-UHFFFAOYSA-N 0.000 claims 1
• HJDNYULQEGIHAU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-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)F)N2 HJDNYULQEGIHAU-UHFFFAOYSA-N 0.000 claims 1
• SNFMPYNCDDDXMP-UHFFFAOYSA-N 2-(3-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC(Cl)=C1 SNFMPYNCDDDXMP-UHFFFAOYSA-N 0.000 claims 1
• BJCUCIYPKOQESA-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=C(Cl)C=CC=1)N2 BJCUCIYPKOQESA-UHFFFAOYSA-N 0.000 claims 1
• BJYUDQWXCKOMFI-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=C(Cl)C=CC=1)N2 BJYUDQWXCKOMFI-UHFFFAOYSA-N 0.000 claims 1
• NUTSBBKBRGDWBN-UHFFFAOYSA-N 2-(3-chlorophenyl)-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=C(Cl)C=CC=1)N2 NUTSBBKBRGDWBN-UHFFFAOYSA-N 0.000 claims 1
• YYLGFKSVCZCPPV-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC(F)=C1 YYLGFKSVCZCPPV-UHFFFAOYSA-N 0.000 claims 1
• CKVBERPZKGLQGP-UHFFFAOYSA-N 2-(3-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=C(F)C=CC=1)N2 CKVBERPZKGLQGP-UHFFFAOYSA-N 0.000 claims 1
• FPQSNKMLZQWPLX-UHFFFAOYSA-N 2-(3-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=C(F)C=CC=1)N2 FPQSNKMLZQWPLX-UHFFFAOYSA-N 0.000 claims 1
• CNSQWZVWEBCADO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C(=CC=NC=2)C)=C1 CNSQWZVWEBCADO-UHFFFAOYSA-N 0.000 claims 1
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• FWVAFXFAIHCNCP-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[6-(2-morpholin-4-ylethoxy)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(OCCN4CCOCC4)=CC=3)C=CN=C2N1 FWVAFXFAIHCNCP-UHFFFAOYSA-N 0.000 claims 1
• NSOAUQXIPCRWHD-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-naphthalen-2-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=CC=3)C=CN=C2N1 NSOAUQXIPCRWHD-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
• 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
• 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
• VKSFGYPSXMVOKE-UHFFFAOYSA-N 2-(furan-3-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(C1=COC=C1)N2 VKSFGYPSXMVOKE-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
• VUZDOEHITRVKIW-UHFFFAOYSA-N 2-[4-(2-piperazin-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=C1NCCN1CCNCC1 VUZDOEHITRVKIW-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
• XVCQHGPGUXYVTR-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-(6-methylpyridin-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(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
• 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
• 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
• 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 compound 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
• 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
• NZQDQPDYLZMCFO-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-n-(2-hydroxycyclopentyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(=O)NC3C(CCC3)O)C=CN=C2N1 NZQDQPDYLZMCFO-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
• 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
• 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
• 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
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• 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
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• 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
• KXXFOBAWNDDEQA-UHFFFAOYSA-N n-(4,4-dimethylpentan-2-yl)-2-(4-fluorophenyl)-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(F)C=C1 KXXFOBAWNDDEQA-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
• 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
• 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
• 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
• PDCLLGAZLJHFBW-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(4-piperidin-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)N1CCCCC1)N2 PDCLLGAZLJHFBW-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 compound 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
• VILVOBGLGPSMAH-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)-2-[4-(2-morpholin-4-ylethylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound 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 compound 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
• QVJINTSNTMHOCE-UHFFFAOYSA-N n-(6-chloro-5-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1=C(Cl)C(C)=CC(NC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 QVJINTSNTMHOCE-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 compound 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 compound 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
• XATTWOQASIHXNV-UHFFFAOYSA-N n-[2-(2-chloropyridin-3-yl)ethyl]-2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound ClC1=NC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 XATTWOQASIHXNV-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
• VDQWQBMDLPTPAH-UHFFFAOYSA-N n-[2-(3-hydroxyphenyl)ethyl]-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound OC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C2=CSC=C2)=C1 VDQWQBMDLPTPAH-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
• ASIPQJZKVFOMPJ-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-(4-fluorophenyl)-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(F)=CC=1)N2 ASIPQJZKVFOMPJ-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• 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 compound 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 compound 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
• PQCORBHAPGUMBJ-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-thiophen-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=1SC=CC=1)N2 PQCORBHAPGUMBJ-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
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