JP2015526442A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015526442A5 JP2015526442A5 JP2015527567A JP2015527567A JP2015526442A5 JP 2015526442 A5 JP2015526442 A5 JP 2015526442A5 JP 2015527567 A JP2015527567 A JP 2015527567A JP 2015527567 A JP2015527567 A JP 2015527567A JP 2015526442 A5 JP2015526442 A5 JP 2015526442A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- indazol
- chloro
- acid
- benzyl
- Prior art date
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- -1 nitro, hydroxy Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 102000001691 Member 3 Group F Nuclear Receptor Subfamily 1 Human genes 0.000 claims 2
- 108010029279 Member 3 Group F Nuclear Receptor Subfamily 1 Proteins 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000001404 mediated effect Effects 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
- PJOFRBVIMBTWIK-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-[(2-methoxyphenyl)methyl]indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC=C1CN1C2=CC=CC(F)=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 PJOFRBVIMBTWIK-UHFFFAOYSA-N 0.000 claims 1
- YUPMGLZSHHVNCQ-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-[(2-pyrazol-1-ylphenyl)methyl]indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=CC=C1N1N=CC=C1 YUPMGLZSHHVNCQ-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
- WURAGKDKWYTIJC-UHFFFAOYSA-N 4-[1-[(2,6-dichlorophenyl)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=C1Cl WURAGKDKWYTIJC-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
- AFVOPYQPKVJNRT-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]indazol-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F AFVOPYQPKVJNRT-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
- WEMJXBBNHATSQI-UHFFFAOYSA-N 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]pyrrolo[3,2-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=CN1CC1=C(Cl)C=CC=C1C(F)(F)F WEMJXBBNHATSQI-UHFFFAOYSA-N 0.000 claims 1
- UQDTXJLULBMLPM-UHFFFAOYSA-N 4-[1-[[2-ethyl-6-(trifluoromethyl)phenyl]methyl]-4-fluoroindazol-3-yl]-5-fluoro-2-hydroxybenzoic acid Chemical compound CCC1=CC=CC(C(F)(F)F)=C1CN1C2=CC=CC(F)=C2C(C=2C(=CC(=C(O)C=2)C(O)=O)F)=N1 UQDTXJLULBMLPM-UHFFFAOYSA-N 0.000 claims 1
- UKVVZLDCTZVQIU-UHFFFAOYSA-N 4-[6-(azetidine-1-carbonyl)-1-[[2-chloro-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=C(C=C11)C(=O)N2CCC2)=NN1CC1=C(Cl)C=CC=C1C(F)(F)F UKVVZLDCTZVQIU-UHFFFAOYSA-N 0.000 claims 1
- RPKXOBUMLPBYDM-UHFFFAOYSA-N 5-fluoro-4-[4-fluoro-1-[[2-(trifluoromethyl)phenyl]methyl]indazol-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1CC1=CC=CC=C1C(F)(F)F RPKXOBUMLPBYDM-UHFFFAOYSA-N 0.000 claims 1
- KQFHZBNTVAKLMC-UHFFFAOYSA-N 5-fluoro-4-[4-fluoro-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]indazol-3-yl]-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=C1C(F)(F)F KQFHZBNTVAKLMC-UHFFFAOYSA-N 0.000 claims 1
- 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
- HJRLATNTZSLNIF-UHFFFAOYSA-N 5-fluoro-4-[4-fluoro-1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]indazol-3-yl]-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(C(F)(F)F)=C1 HJRLATNTZSLNIF-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000011200 Kawasaki disease Diseases 0.000 claims 1
- 102000016978 Orphan receptors Human genes 0.000 claims 1
- 108070000031 Orphan receptors Proteins 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000004452 carbocyclyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QDFPMRONZBLFHC-UHFFFAOYSA-N methyl 4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-c]pyridin-3-yl]-3-fluorobenzoate Chemical compound COC(=O)c1ccc(-c2nn(Cc3c(Cl)cccc3C(F)(F)F)c3cnccc23)c(F)c1 QDFPMRONZBLFHC-UHFFFAOYSA-N 0.000 claims 1
- 201000000626 mucocutaneous leishmaniasis Diseases 0.000 claims 1
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 102000003702 retinoic acid receptors Human genes 0.000 claims 1
- 108090000064 retinoic acid receptors Proteins 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- LTMWQKQQYYFDQL-UHFFFAOYSA-M sodium;4-[1-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-4-fluoro-6-(3-methoxyazetidine-1-carbonyl)indazol-3-yl]-5-fluoro-2-hydroxybenzoate Chemical compound [Na+].C1C(OC)CN1C(=O)C1=CC(F)=C(C(=NN2CC=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=C(O)C=3)C([O-])=O)F)C2=C1 LTMWQKQQYYFDQL-UHFFFAOYSA-M 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 *c1cccc(*)c1C[n](c1c2****1)nc2-c(c(*)c1)ccc1C(O)=O Chemical compound *c1cccc(*)c1C[n](c1c2****1)nc2-c(c(*)c1)ccc1C(O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2012/080134 | 2012-08-15 | ||
| PCT/CN2012/080134 WO2014026329A1 (en) | 2012-08-15 | 2012-08-15 | N-alkylated indole and indazole compounds as rorgammat inhibitors and uses thereof |
| PCT/US2013/054893 WO2014028591A2 (en) | 2012-08-15 | 2013-08-14 | N-ALKYLATED INDOLE AND INDAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015526442A JP2015526442A (ja) | 2015-09-10 |
| JP2015526442A5 true JP2015526442A5 (enExample) | 2016-09-23 |
| JP6411345B2 JP6411345B2 (ja) | 2018-10-24 |
Family
ID=50101187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015527567A Expired - Fee Related JP6411345B2 (ja) | 2012-08-15 | 2013-08-14 | ＲＯＲγＴ阻害剤としてのＮ−アルキル化インドールおよびインダゾール化合物およびそれらの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9556168B2 (enExample) |
| EP (1) | EP2884977B1 (enExample) |
| JP (1) | JP6411345B2 (enExample) |
| KR (1) | KR20150041659A (enExample) |
| AU (1) | AU2013302727A1 (enExample) |
| BR (1) | BR112015003397A2 (enExample) |
| CA (1) | CA2881693A1 (enExample) |
| RU (1) | RU2015108935A (enExample) |
| WO (2) | WO2014026329A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| 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 |
| WO2014026330A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| JP6466461B2 (ja) | 2014-02-03 | 2019-02-06 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | Ｒｏｒガンマのジヒドロピロロピリジン阻害剤 |
| CA2939305A1 (en) | 2014-02-27 | 2015-09-03 | Lycera Corporation | Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma & related therapeutic methods |
| 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 |
| EP3209641A4 (en) | 2014-05-05 | 2018-06-06 | Lycera Corporation | Benzenesulfonamido and related compounds for use as agonists of ror and the treatement of disease |
| EP3207043B3 (en) | 2014-10-14 | 2019-10-02 | Vitae Pharmaceuticals, LLC | Dihydropyrrolopyridine inhibitors of ror-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 |
| US10435402B2 (en) * | 2015-01-08 | 2019-10-08 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| CA2975157C (en) * | 2015-01-30 | 2019-09-17 | Pfizer Inc. | Sulfonamide-substituted indole modulators of rorc2 and methods of use thereof |
| WO2016130818A1 (en) * | 2015-02-11 | 2016-08-18 | Merck Sharp & Dohme Corp. | SUBSTITUTED PYRAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| WO2016128908A1 (en) | 2015-02-12 | 2016-08-18 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| JP2018513123A (ja) | 2015-03-12 | 2018-05-24 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Ｒｏｒガンマ阻害剤を用いてがんを治療するための方法 |
| 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 |
| CA2987289A1 (en) | 2015-06-11 | 2016-12-15 | Lycera Corporation | Aryl dihydro-2h-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of ror.gamma. and the treatment of disease |
| DK3331876T3 (da) | 2015-08-05 | 2021-01-11 | Vitae Pharmaceuticals Llc | Modulators of ror-gamma |
| JP6863970B2 (ja) * | 2015-09-21 | 2021-04-21 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | ヘテロ環式化合物およびそれらの使用 |
| EP3368535B1 (en) * | 2015-10-27 | 2020-12-02 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| JP2018535958A (ja) | 2015-10-27 | 2018-12-06 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ＲＯＲγＴ阻害薬としての置換インダゾール化合物及びその使用 |
| JP2018531957A (ja) | 2015-10-27 | 2018-11-01 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ＲＯＲγＴ阻害薬としての置換二環式ピラゾール化合物及びその使用 |
| EP3377482B1 (en) | 2015-11-20 | 2021-05-12 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| IL260691B (en) * | 2016-01-21 | 2022-07-01 | Zibo Biopolar Changsheng Pharmaceutical Co Ltd | Bruton's tyrosine kinase inhibitors |
| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| US9481674B1 (en) | 2016-06-10 | 2016-11-01 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| AU2017360939B2 (en) | 2016-11-18 | 2022-03-03 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| WO2018188590A1 (en) * | 2017-04-11 | 2018-10-18 | Sunshine Lake Pharma Co., Ltd. | Fluorine-substituted indazole compounds and uses thereof |
| BR112020001246A2 (pt) | 2017-07-24 | 2020-07-21 | Vitae Pharmaceuticals, Llc | inibidores de rory |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| CN108586432B (zh) * | 2018-05-31 | 2020-08-25 | 温州医科大学 | 一种3-(吲哚-5-基)-吲唑衍生物及其应用 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670447A (en) | 1983-08-22 | 1987-06-02 | Hoechst-Roussel Pharmaceuticals Inc. | Antipsychotic 3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles |
| PT95899A (pt) * | 1989-11-17 | 1991-09-13 | Glaxo Group Ltd | Processo para a preparacao de derivados indole |
| JPH09511334A (ja) * | 1994-03-30 | 1997-11-11 | チバ−ガイギー アクチェンゲゼルシャフト | Ｒｚｒ受容体ファミリーを用いるスクリーニング方法 |
| US5639780A (en) * | 1995-05-22 | 1997-06-17 | Merck Frosst Canada, Inc. | N-benzyl indol-3-yl butanoic acid derivatives as cyclooxygenase inhibitors |
| US6133290A (en) | 1998-07-31 | 2000-10-17 | Eli Lilly And Company | 5-HT1F agonists |
| US6716452B1 (en) * | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
| US6387942B2 (en) * | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| GB0117577D0 (en) | 2001-02-16 | 2001-09-12 | Aventis Pharm Prod Inc | Novel heterocyclic substituted carbonyl derivatives and their use as dopamine D receptor ligands |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| US7754751B2 (en) * | 2004-03-15 | 2010-07-13 | Yung Shin Pharmaceutical Ind. Co., Ltd. | Preferential inhibition of release of pro-inflammatory cytokines |
| BRPI0514017A (pt) | 2004-08-03 | 2008-05-27 | Wyeth Corp | indazóis úteis no tratamento de doenças cardiovasculares |
| EP1786813A2 (en) | 2004-09-03 | 2007-05-23 | Plexxikon, Inc. | Bicyclic heteroaryl pde4b inhibitors |
| JP2008513512A (ja) * | 2004-09-21 | 2008-05-01 | アサーシス， インク． | Ｃｒｔｈ２受容体拮抗作用を示すインドール酢酸およびこれらの使用 |
| CN100516049C (zh) * | 2004-11-16 | 2009-07-22 | 永信药品工业股份有限公司 | 抗血管生成药n2-(取代的芳基甲基)-3-(取代的苯基)吲唑的合成 |
| JP4954086B2 (ja) | 2004-12-08 | 2012-06-13 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | １ｈ−ピロロ［２，３−ｂ］ピリジン |
| WO2007098418A1 (en) | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-ht6 receptor affinity |
| JP4675801B2 (ja) | 2006-03-06 | 2011-04-27 | 日本メナード化粧品株式会社 | Ｒｏｒ活性化剤 |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| JP5496876B2 (ja) | 2007-04-16 | 2014-05-21 | アッヴィ・インコーポレイテッド | ７−置換されていないインドール系Ｍｃｌ−１阻害薬 |
| GB0708141D0 (en) | 2007-04-26 | 2007-06-06 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| AR067326A1 (es) | 2007-05-11 | 2009-10-07 | Novartis Ag | Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido |
| TW200911262A (en) | 2007-06-05 | 2009-03-16 | Schering Corp | Novel compounds that are ERK inhibitors |
| CA2694224A1 (en) | 2007-07-25 | 2009-01-29 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| EP2346508B1 (en) * | 2008-09-26 | 2016-08-24 | Intellikine, LLC | Heterocyclic kinase inhibitors |
| 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 |
| EP2379561B1 (en) | 2008-11-25 | 2015-11-04 | 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 |
| US20130017188A1 (en) | 2009-07-31 | 2013-01-17 | 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 |
| US8263781B2 (en) | 2009-12-18 | 2012-09-11 | Janssen Pharmaceutica Nv | Substituted aminothiazolone indazoles as estrogen related receptor-alpha modulators |
| WO2011103189A1 (en) | 2010-02-16 | 2011-08-25 | Uwm Research Foundation, Inc. | Methods of reducing virulence in bacteria |
| WO2011146313A1 (en) | 2010-05-19 | 2011-11-24 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| 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 |
| BR112013015854B1 (pt) | 2010-12-22 | 2019-07-02 | Ludwig-Maximilians-Universistät München | Processos para produzir reagentes de organozinco e compostos orgânicos, composição de reagentes de organozinco e complexo de coordenação de zinco |
| 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 |
| 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 |
| 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 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 KR KR20157006321A patent/KR20150041659A/ko not_active Withdrawn
- 2013-08-14 EP EP13829125.7A patent/EP2884977B1/en active Active
- 2013-08-14 RU RU2015108935A patent/RU2015108935A/ru unknown
- 2013-08-14 JP JP2015527567A patent/JP6411345B2/ja not_active Expired - Fee Related
- 2013-08-14 CA CA2881693A patent/CA2881693A1/en not_active Abandoned
- 2013-08-14 WO PCT/US2013/054893 patent/WO2014028591A2/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015526442A5 (enExample) | ||
| RU2015108935A (ru) | СОЕДИНЕНИЯ N-АЛКИЛИРОВАННЫХ ИНДОЛОВ И ИНДАЗОЛОВ В КАЧЕСТВЕ ИНГИБИТОРОВ RORgammaT И СПОСОБЫ ИХ ПРИМЕНЕНИЯ | |
| RU2013141528A (ru) | ИНГИБИТОРЫ РЕЦЕПТОРОВ RORгаммаТ | |
| JP2014509316A5 (enExample) | ||
| JP6170040B2 (ja) | ピルフェニドン及び選択された患者における抗線維化療法 | |
| JP2018519323A5 (enExample) | ||
| SI2989100T1 (en) | NAFTIRIDINE DERIVATIVES USED AS ANTAGONISTS INTEGRITY OF ALFA-V-BETA-6 | |
| JP2014526492A5 (enExample) | ||
| JP2015500326A5 (enExample) | ||
| RU2013112122A (ru) | Новые замещенные хинолиновые соединения как ингибиторы s-нитрозоглутатион-редуктазы | |
| NZ610746A (en) | Methods of treatment using selective bcl-2 inhibitors | |
| JP2017502073A5 (enExample) | ||
| RU2009104340A (ru) | Производные [4,5']бипиримидинил-6,4'-диамина в качестве ингибиторов протеинкиназы | |
| ME01462B (me) | Vinilindazolilna jedinjenja" | |
| KR20110117658A (ko) | 메토트렉세이트 및 ｄｈｏｄｈ 억제제를 포함하는 조합물 | |
| JP2007522200A (ja) | 非定型抗精神病薬とコルチコトロピン放出因子拮抗薬の治療的組合せ | |
| NZ603463A (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| JP2012502017A5 (enExample) | ||
| JP2012515787A5 (enExample) | ||
| JP2012515788A5 (enExample) | ||
| JP2004524301A5 (enExample) | ||
| JP2011524896A5 (enExample) | ||
| JP2013520397A5 (enExample) | ||
| JP2016500068A5 (enExample) | ||
| JP2016514711A5 (enExample) |