RU2015108935A - СОЕДИНЕНИЯ N-АЛКИЛИРОВАННЫХ ИНДОЛОВ И ИНДАЗОЛОВ В КАЧЕСТВЕ ИНГИБИТОРОВ RORgammaT И СПОСОБЫ ИХ ПРИМЕНЕНИЯ - Google Patents
СОЕДИНЕНИЯ N-АЛКИЛИРОВАННЫХ ИНДОЛОВ И ИНДАЗОЛОВ В КАЧЕСТВЕ ИНГИБИТОРОВ RORgammaT И СПОСОБЫ ИХ ПРИМЕНЕНИЯ Download PDFInfo
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- RU2015108935A RU2015108935A RU2015108935A RU2015108935A RU2015108935A RU 2015108935 A RU2015108935 A RU 2015108935A RU 2015108935 A RU2015108935 A RU 2015108935A RU 2015108935 A RU2015108935 A RU 2015108935A RU 2015108935 A RU2015108935 A RU 2015108935A
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- Prior art keywords
- fluoro
- indazol
- chloro
- acid
- benzyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract 27
- 238000000034 method Methods 0.000 title claims 4
- 150000002473 indoazoles Chemical class 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 26
- 150000003839 salts Chemical class 0.000 claims abstract 15
- 239000012453 solvate Substances 0.000 claims abstract 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical group 0.000 claims abstract 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 13
- -1 nitro, hydroxy Chemical group 0.000 claims abstract 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- IKGQYGPZQXDRLX-UHFFFAOYSA-N 4-[1-[(2-chloro-6-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(F)C=CC=C1Cl IKGQYGPZQXDRLX-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- MBEXROPPFIYEST-UHFFFAOYSA-N 3-fluoro-4-[1-[(2,3,6-trifluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC(F)=C1F MBEXROPPFIYEST-UHFFFAOYSA-N 0.000 claims 1
- UOQQRZRMSQCDFP-UHFFFAOYSA-N 3-fluoro-4-[1-[1-[2-(trifluoromethyl)phenyl]ethyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound N1=C(C=2C(=CC(=CC=2)C(O)=O)F)C2=NC=CC=C2N1C(C)C1=CC=CC=C1C(F)(F)F UOQQRZRMSQCDFP-UHFFFAOYSA-N 0.000 claims 1
- ZVOMDSUOZWCCOV-UHFFFAOYSA-N 3-fluoro-4-[1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC=C1C(F)(F)F ZVOMDSUOZWCCOV-UHFFFAOYSA-N 0.000 claims 1
- QCJIXFMKLFDINN-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-[(2-fluoro-6-methoxyphenyl)methyl]indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1CN1C2=CC=CC(F)=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 QCJIXFMKLFDINN-UHFFFAOYSA-N 0.000 claims 1
- KOIBUQVZBHWSBU-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-[[2-fluoro-5-(trifluoromethoxy)phenyl]methyl]indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(OC(F)(F)F)=CC=C1F KOIBUQVZBHWSBU-UHFFFAOYSA-N 0.000 claims 1
- KCJINTIQSDPDEI-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-[[3-(trifluoromethoxy)phenyl]methyl]indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=CC(OC(F)(F)F)=C1 KCJINTIQSDPDEI-UHFFFAOYSA-N 0.000 claims 1
- STPWOOVOHOVOOC-UHFFFAOYSA-N 4-(1-benzyl-4-fluoroindazol-3-yl)-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=CC=C1 STPWOOVOHOVOOC-UHFFFAOYSA-N 0.000 claims 1
- YLDCERSLUCUTDK-UHFFFAOYSA-N 4-[1-(1-benzothiophen-7-ylmethyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=CC=CC2=C1SC=C2 YLDCERSLUCUTDK-UHFFFAOYSA-N 0.000 claims 1
- OWVOGNOZKCFTAV-UHFFFAOYSA-N 4-[1-[(2,3-dichloro-6-fluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC(Cl)=C1Cl OWVOGNOZKCFTAV-UHFFFAOYSA-N 0.000 claims 1
- ZQYPITWSSIRYAA-UHFFFAOYSA-N 4-[1-[(2,5-dichlorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(Cl)=CC=C1Cl ZQYPITWSSIRYAA-UHFFFAOYSA-N 0.000 claims 1
- RXAAQCKHPNLMBV-UHFFFAOYSA-N 4-[1-[(2,6-dichlorophenyl)methyl]-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1Cl RXAAQCKHPNLMBV-UHFFFAOYSA-N 0.000 claims 1
- APEQDZPDQZHIBT-UHFFFAOYSA-N 4-[1-[(2,6-difluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC=C1F APEQDZPDQZHIBT-UHFFFAOYSA-N 0.000 claims 1
- XPMNNYBIPJCYPI-UHFFFAOYSA-N 4-[1-[(2-bromo-3-fluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=CC=CC(F)=C1Br XPMNNYBIPJCYPI-UHFFFAOYSA-N 0.000 claims 1
- TWRCGSFWZYWGHK-UHFFFAOYSA-N 4-[1-[(2-bromo-5-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(F)=CC=C1Br TWRCGSFWZYWGHK-UHFFFAOYSA-N 0.000 claims 1
- FIJUMHIHBIPOSO-UHFFFAOYSA-N 4-[1-[(2-bromo-6-chlorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(Cl)C=CC=C1Br FIJUMHIHBIPOSO-UHFFFAOYSA-N 0.000 claims 1
- VXCPJCUOCADWBI-UHFFFAOYSA-N 4-[1-[(2-bromo-6-fluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC=C1Br VXCPJCUOCADWBI-UHFFFAOYSA-N 0.000 claims 1
- LYVRLEWJCUKJIB-UHFFFAOYSA-N 4-[1-[(2-chloro-3,6-difluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC(F)=C1Cl LYVRLEWJCUKJIB-UHFFFAOYSA-N 0.000 claims 1
- XFFJJPIEGCBVNL-UHFFFAOYSA-N 4-[1-[(2-chloro-4-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=C(F)C=C1Cl XFFJJPIEGCBVNL-UHFFFAOYSA-N 0.000 claims 1
- GKDJIGKBPRMCAU-UHFFFAOYSA-N 4-[1-[(2-chloro-5-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(F)=CC=C1Cl GKDJIGKBPRMCAU-UHFFFAOYSA-N 0.000 claims 1
- PYKZZZGWNQUKIU-UHFFFAOYSA-N 4-[1-[(2-chloro-6-cyclopropylphenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1C1CC1 PYKZZZGWNQUKIU-UHFFFAOYSA-N 0.000 claims 1
- WUFBYPPOWBWJHP-UHFFFAOYSA-N 4-[1-[(2-chloro-6-fluoro-3-methoxyphenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound COC1=CC=C(F)C(CN2C3=CC=CN=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1Cl WUFBYPPOWBWJHP-UHFFFAOYSA-N 0.000 claims 1
- HLRFMNHKFMBVPT-UHFFFAOYSA-N 4-[1-[(2-chloro-6-fluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(F)C=CC=C1Cl HLRFMNHKFMBVPT-UHFFFAOYSA-N 0.000 claims 1
- RBRMMYDNJVNNKB-UHFFFAOYSA-N 4-[1-[(2-chloro-6-methoxycarbonylphenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound COC(=O)C1=CC=CC(Cl)=C1CN1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 RBRMMYDNJVNNKB-UHFFFAOYSA-N 0.000 claims 1
- WMAJGLCGUMZZHV-UHFFFAOYSA-N 4-[1-[(2-chloro-6-methylphenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound CC1=CC=CC(Cl)=C1CN1C2=CC=CC(F)=C2C(C=2C(=CC(=C(O)C=2)C(O)=O)F)=N1 WMAJGLCGUMZZHV-UHFFFAOYSA-N 0.000 claims 1
- WJUMAGBJYHNHPM-UHFFFAOYSA-N 4-[1-[(2-cyanophenyl)methyl]-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=CC=C1C#N WJUMAGBJYHNHPM-UHFFFAOYSA-N 0.000 claims 1
- SWDDGKKLWQNVDO-UHFFFAOYSA-N 4-[1-[(3,5-dichlorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(Cl)=CC(Cl)=C1 SWDDGKKLWQNVDO-UHFFFAOYSA-N 0.000 claims 1
- LXFXMHBPHXOBHM-UHFFFAOYSA-N 4-[1-[(3,6-dichloro-2-fluorophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(Cl)C=CC(Cl)=C1F LXFXMHBPHXOBHM-UHFFFAOYSA-N 0.000 claims 1
- SFBMOSWFNDPQGC-UHFFFAOYSA-N 4-[1-[(3-chloro-5-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC(F)=CC(Cl)=C1 SFBMOSWFNDPQGC-UHFFFAOYSA-N 0.000 claims 1
- MNPUFYMIIBIBHU-UHFFFAOYSA-N 4-[1-[(4-bromo-2-fluorophenyl)methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=C(Br)C=C1F MNPUFYMIIBIBHU-UHFFFAOYSA-N 0.000 claims 1
- FMOGOMQESOYLOL-UHFFFAOYSA-N 4-[1-[(5-chloro-2-cyanophenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=CC(Cl)=CC=C1C#N FMOGOMQESOYLOL-UHFFFAOYSA-N 0.000 claims 1
- UMXMUTZTYXXWRH-UHFFFAOYSA-N 4-[1-[(6-chloro-2-fluoro-3-methoxyphenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound COC1=CC=C(Cl)C(CN2C3=CC=CN=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1F UMXMUTZTYXXWRH-UHFFFAOYSA-N 0.000 claims 1
- UMZFNONHAAREOC-UHFFFAOYSA-N 4-[1-[(6-chloro-2-fluoro-3-methylphenyl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC=C(Cl)C(CN2C3=CC=CN=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1F UMZFNONHAAREOC-UHFFFAOYSA-N 0.000 claims 1
- DVHGXCCMQJBABK-UHFFFAOYSA-N 4-[1-[1-[2-chloro-6-(trifluoromethyl)phenyl]ethyl]-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound N1=C(C=2C(=CC(=CC=2)C(O)=O)F)C2=C(F)C=CC=C2N1C(C)C1=C(Cl)C=CC=C1C(F)(F)F DVHGXCCMQJBABK-UHFFFAOYSA-N 0.000 claims 1
- WXFNQSRZVJSJNS-UHFFFAOYSA-N 4-[1-[[2,6-dichloro-3-(trifluoromethyl)phenyl]methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(Cl)C=CC(C(F)(F)F)=C1Cl WXFNQSRZVJSJNS-UHFFFAOYSA-N 0.000 claims 1
- KPHHIXOCRMMGTI-UHFFFAOYSA-N 4-[1-[[2-bromo-6-(trifluoromethyl)phenyl]methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Br)C=CC=C1C(F)(F)F KPHHIXOCRMMGTI-UHFFFAOYSA-N 0.000 claims 1
- CDFNKXNAPBCTQM-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(1-hydroxycyclobutyl)phenyl]methyl]-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1C1(O)CCC1 CDFNKXNAPBCTQM-UHFFFAOYSA-N 0.000 claims 1
- MOXBQBYZYCYBDJ-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-4-fluoroindazol-3-yl]-2,5-difluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F MOXBQBYZYCYBDJ-UHFFFAOYSA-N 0.000 claims 1
- UEFCQVHKUHFXBD-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F UEFCQVHKUHFXBD-UHFFFAOYSA-N 0.000 claims 1
- AFJYKLOUMRIMDF-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-4-fluoroindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F AFJYKLOUMRIMDF-UHFFFAOYSA-N 0.000 claims 1
- GKBHCRMCWLYHNU-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F GKBHCRMCWLYHNU-UHFFFAOYSA-N 0.000 claims 1
- KVXXSQKFUUMXSE-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-c]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=NC=C11)=CN1CC1=C(Cl)C=CC=C1C(F)(F)F KVXXSQKFUUMXSE-UHFFFAOYSA-N 0.000 claims 1
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- QFDPESDKWVARHY-UHFFFAOYSA-N 5-fluoro-4-[4-fluoro-1-[[2-methyl-6-(trifluoromethyl)phenyl]methyl]indazol-3-yl]-2-hydroxybenzoic acid Chemical compound CC1=CC=CC(C(F)(F)F)=C1CN1C2=CC=CC(F)=C2C(C=2C(=CC(=C(O)C=2)C(O)=O)F)=N1 QFDPESDKWVARHY-UHFFFAOYSA-N 0.000 claims 1
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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Applications Claiming Priority (3)
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| PCT/CN2012/080134 WO2014026329A1 (en) | 2012-08-15 | 2012-08-15 | N-alkylated indole and indazole compounds as rorgammat inhibitors and uses thereof |
| CNPCT/CN2012/080134 | 2012-08-15 | ||
| PCT/US2013/054893 WO2014028591A2 (en) | 2012-08-15 | 2013-08-14 | N-ALKYLATED INDOLE AND INDAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
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| US11104690B2 (en) | 2016-11-18 | 2021-08-31 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
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| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
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| WO2014026327A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 4-heteroaryl substituted benzoic acid compounds as rorgammat inhibitors and uses thereof |
| WO2014026330A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| DK3102576T3 (da) | 2014-02-03 | 2019-07-22 | Vitae Pharmaceuticals Llc | Dihydropyrrolopyridininhibitorer af ror-gamma |
| EP3110429A4 (en) | 2014-02-27 | 2018-02-21 | Lycera Corporation | Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma & related therapeutic methods |
| WO2015171558A2 (en) | 2014-05-05 | 2015-11-12 | Lycera Corporation | BENZENESULFONAMIDO AND RELATED COMPOUNDS FOR USE AS AGONISTS OF RORγ AND THE TREATEMENT OF DISEASE |
| EP3140291A4 (en) | 2014-05-05 | 2018-01-10 | Lycera Corporation | Tetrahydroquinoline sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| MX371304B (es) | 2014-10-14 | 2020-01-24 | Vitae Pharmaceuticals Llc | Dihidropirrolopiridinas inhibidoras del receptor huérfano-gamma. |
| GB201419015D0 (en) | 2014-10-24 | 2014-12-10 | Orca Pharmaceuticals Ltd | Compounds |
| US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
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| EP3256450B1 (en) | 2015-02-11 | 2020-12-02 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as ror-gamma-t inhibitors and uses thereof |
| WO2016128908A1 (en) | 2015-02-12 | 2016-08-18 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| EP3268087A4 (en) | 2015-03-12 | 2018-08-29 | The Regents of the University of California | METHODS FOR TREATING CANCER WITH RORgamma INHIBITORS |
| JP2018515491A (ja) | 2015-05-05 | 2018-06-14 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγの作動薬及び疾患の療法として使用するジヒドロ−２Ｈ−ベンゾ［ｂ］［１，４］オキサジンスルホンアミド及び関連化合物 |
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| WO2017024018A1 (en) | 2015-08-05 | 2017-02-09 | Vitae Pharmaceuticals, Inc. | Modulators of ror-gamma |
| TWI732785B (zh) * | 2015-09-21 | 2021-07-11 | 美商普雷辛肯公司 | 雜環化合物及其用途 |
| US10344000B2 (en) | 2015-10-27 | 2019-07-09 | Merck Sharp & Dohme Corp. | Substituted bicyclic pyrazole compounds as RORgammaT inhibitors and uses thereof |
| US10287272B2 (en) | 2015-10-27 | 2019-05-14 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as RORgammaT inhibitors and uses thereof |
| WO2017075185A1 (en) * | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| AU2016355710B2 (en) | 2015-11-20 | 2021-03-25 | Vitae Pharmaceuticals, Llc | Modulators of ROR-gamma |
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| JP5731978B2 (ja) * | 2008-09-26 | 2015-06-10 | インテリカイン， エルエルシー | 複素環キナーゼ阻害剤 |
| WO2010050837A1 (ru) | 2008-10-28 | 2010-05-06 | Haskin Lev Yakovlevich | Ветроэнергетическая установка |
| EP2181710A1 (en) | 2008-10-28 | 2010-05-05 | Phenex Pharmaceuticals AG | Ligands for modulation of orphan receptor-gamma (NR1F3) activity |
| AU2009324894B2 (en) | 2008-11-25 | 2015-04-09 | University Of Rochester | MLK inhibitors and methods of use |
| WO2010150837A1 (ja) | 2009-06-25 | 2010-12-29 | 第一三共株式会社 | インドリン誘導体 |
| EP2459184A1 (en) | 2009-07-31 | 2012-06-06 | The Brigham and Women's Hospital, Inc. | Modulation of sgk1 expression in th17 cells to modulate th17-mediated immune responses |
| WO2011055270A1 (en) * | 2009-11-04 | 2011-05-12 | Wyeth Llc | Indole based receptor crth2 antagonists |
| CN102770429A (zh) * | 2009-12-18 | 2012-11-07 | 詹森药业有限公司 | 用作雌激素相关受体-α调节剂的取代的氨基噻唑酮吲唑 |
| CN102883602B (zh) | 2010-02-16 | 2017-07-18 | Uwm研究基金会有限公司 | 降低细菌的毒力的方法 |
| EP2571361A4 (en) | 2010-05-19 | 2013-11-13 | Univ North Carolina | PYRAZOLOPYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| WO2012064744A2 (en) | 2010-11-08 | 2012-05-18 | Lycera Corporation | Tetrahydroquinoline and related bicyclic compounds for inhibition of rorϒ activity and the treatment of disease |
| CN103429598B (zh) | 2010-12-22 | 2018-03-30 | 慕尼黑路德维希马克西米利安斯大学 | 有机锌络合物及其制备和使用方法 |
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| JP2014166961A (ja) | 2011-06-20 | 2014-09-11 | Dainippon Sumitomo Pharma Co Ltd | 新規インダゾール誘導体 |
| WO2014026330A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| WO2014026327A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 4-heteroaryl substituted benzoic acid compounds as rorgammat inhibitors and uses thereof |
| WO2014026328A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-cyclohexenyl substituted indole and indazole compounds as rorgammat inhibitors and uses thereof |
-
2012
- 2012-08-15 WO PCT/CN2012/080134 patent/WO2014026329A1/en not_active Ceased
-
2013
- 2013-08-14 RU RU2015108935A patent/RU2015108935A/ru unknown
- 2013-08-14 BR BR112015003397A patent/BR112015003397A2/pt not_active IP Right Cessation
- 2013-08-14 US US14/421,052 patent/US9556168B2/en active Active
- 2013-08-14 AU AU2013302727A patent/AU2013302727A1/en not_active Abandoned
- 2013-08-14 JP JP2015527567A patent/JP6411345B2/ja not_active Expired - Fee Related
- 2013-08-14 KR KR20157006321A patent/KR20150041659A/ko not_active Withdrawn
- 2013-08-14 EP EP13829125.7A patent/EP2884977B1/en active Active
- 2013-08-14 WO PCT/US2013/054893 patent/WO2014028591A2/en not_active Ceased
- 2013-08-14 CA CA2881693A patent/CA2881693A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11104690B2 (en) | 2016-11-18 | 2021-08-31 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014028591A3 (en) | 2014-04-17 |
| US20150210687A1 (en) | 2015-07-30 |
| EP2884977B1 (en) | 2017-10-11 |
| CA2881693A1 (en) | 2014-02-20 |
| JP2015526442A (ja) | 2015-09-10 |
| EP2884977A4 (en) | 2016-05-11 |
| WO2014028591A2 (en) | 2014-02-20 |
| KR20150041659A (ko) | 2015-04-16 |
| EP2884977A2 (en) | 2015-06-24 |
| BR112015003397A2 (pt) | 2019-09-24 |
| AU2013302727A1 (en) | 2015-03-05 |
| WO2014026329A1 (en) | 2014-02-20 |
| JP6411345B2 (ja) | 2018-10-24 |
| US9556168B2 (en) | 2017-01-31 |
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