JP2015526441A5 - - Google Patents
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- Publication number
- JP2015526441A5 JP2015526441A5 JP2015527566A JP2015527566A JP2015526441A5 JP 2015526441 A5 JP2015526441 A5 JP 2015526441A5 JP 2015527566 A JP2015527566 A JP 2015527566A JP 2015527566 A JP2015527566 A JP 2015527566A JP 2015526441 A5 JP2015526441 A5 JP 2015526441A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- trifluoromethyl
- indazol
- benzoyl
- alkyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 59
- -1 nitro, hydroxy Chemical group 0.000 claims 34
- 125000003545 alkoxy group Chemical group 0.000 claims 31
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 31
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- FOCBRZYNWUYTNP-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(morpholine-4-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(=O)N2CCOCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F FOCBRZYNWUYTNP-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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- CUJAFWQPUBJJEJ-UHFFFAOYSA-N 2-acetamido-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)C)=CC(C=2C3=CC=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 CUJAFWQPUBJJEJ-UHFFFAOYSA-N 0.000 claims 1
- RQBDVVCZSCAYQL-UHFFFAOYSA-N 3-(4-carboxyphenyl)-1-[2-chloro-6-(trifluoromethyl)benzoyl]indazole-6-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F RQBDVVCZSCAYQL-UHFFFAOYSA-N 0.000 claims 1
- FGSXFZVLHMWUDU-UHFFFAOYSA-N 3-fluoro-4-[1-(1-methylindole-2-carbonyl)indazol-3-yl]benzoic acid Chemical compound C=1C2=CC=CC=C2N(C)C=1C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F FGSXFZVLHMWUDU-UHFFFAOYSA-N 0.000 claims 1
- BPPONUKAAREGJL-UHFFFAOYSA-N 3-fluoro-4-[1-(2-methoxyacetyl)indazol-3-yl]benzoic acid Chemical compound C12=CC=CC=C2N(C(=O)COC)N=C1C1=CC=C(C(O)=O)C=C1F BPPONUKAAREGJL-UHFFFAOYSA-N 0.000 claims 1
- VWAYLDITYUHKSI-UHFFFAOYSA-N 3-fluoro-4-[1-(2-phenylpropanoyl)indazol-3-yl]benzoic acid Chemical compound C=1C=CC=CC=1C(C)C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F VWAYLDITYUHKSI-UHFFFAOYSA-N 0.000 claims 1
- URJOBDIUNWPXTR-UHFFFAOYSA-N 3-fluoro-4-[1-(naphthalene-1-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=CC=CC=C12 URJOBDIUNWPXTR-UHFFFAOYSA-N 0.000 claims 1
- RQLYGRRZWKTFLU-UHFFFAOYSA-N 3-fluoro-4-[1-(oxolane-2-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1OCCC1 RQLYGRRZWKTFLU-UHFFFAOYSA-N 0.000 claims 1
- AHXGVYIRKMKSAV-UHFFFAOYSA-N 3-fluoro-4-[1-(pyridine-3-carbonyl)indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CN=C1 AHXGVYIRKMKSAV-UHFFFAOYSA-N 0.000 claims 1
- FEMMZTXFLFEFMF-UHFFFAOYSA-N 3-fluoro-4-[1-[2-(2-oxopyrrolidin-1-yl)acetyl]indazol-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)CN1C(=O)CCC1 FEMMZTXFLFEFMF-UHFFFAOYSA-N 0.000 claims 1
- UFMFURBJBPRJFN-UHFFFAOYSA-N 3-fluoro-4-[1-[3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-6-carbonyl]indazol-3-yl]benzoic acid Chemical compound C1N(C(=O)OC(C)(C)C)CC2C1C2C(=O)N(C1=CC=CC=C11)N=C1C1=CC=C(C(O)=O)C=C1F UFMFURBJBPRJFN-UHFFFAOYSA-N 0.000 claims 1
- MYRZEDFAAXWOCE-UHFFFAOYSA-N 4-[1-(1-benzofuran-7-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1OC=C2 MYRZEDFAAXWOCE-UHFFFAOYSA-N 0.000 claims 1
- HLQBLHMEGINUEZ-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1-benzofuran-7-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1OCC2 HLQBLHMEGINUEZ-UHFFFAOYSA-N 0.000 claims 1
- ZQSOJGWWQMLPEG-UHFFFAOYSA-N 4-[1-(2,3-dihydro-1h-indene-4-carbonyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC2=C1CCC2 ZQSOJGWWQMLPEG-UHFFFAOYSA-N 0.000 claims 1
- KNXIOXOXYSMFDK-UHFFFAOYSA-N 4-[1-(2-bromo-3-chlorobenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC(Cl)=C1Br KNXIOXOXYSMFDK-UHFFFAOYSA-N 0.000 claims 1
- VQYAVXSWJIEBDY-UHFFFAOYSA-N 4-[1-(2-bromo-3-methylbenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC=CC(C(=O)N2C3=CC=CC=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1Br VQYAVXSWJIEBDY-UHFFFAOYSA-N 0.000 claims 1
- BCDKQBWCSBECKY-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclobutylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCC1 BCDKQBWCSBECKY-UHFFFAOYSA-N 0.000 claims 1
- CKFNTMBCGYATAC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclobutylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCC1 CKFNTMBCGYATAC-UHFFFAOYSA-N 0.000 claims 1
- RDQQWHRZYWLWJC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopentylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CCCC1 RDQQWHRZYWLWJC-UHFFFAOYSA-N 0.000 claims 1
- RUPATPKYIMISQN-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoroindazol-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 RUPATPKYIMISQN-UHFFFAOYSA-N 0.000 claims 1
- ITAJZCHZGRGIEJ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoroindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 ITAJZCHZGRGIEJ-UHFFFAOYSA-N 0.000 claims 1
- AAADBGOEWPPOQQ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)indazol-3-yl]-3,5-difluorobenzoic acid Chemical compound ClC1=C(C(=O)N2N=C(C3=CC=CC=C23)C2=C(C=C(C(=O)O)C=C2F)F)C(=CC=C1)C1CC1 AAADBGOEWPPOQQ-UHFFFAOYSA-N 0.000 claims 1
- CSTNVZNXJBJIAB-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 CSTNVZNXJBJIAB-UHFFFAOYSA-N 0.000 claims 1
- AMQKIZZEIKBRFO-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 AMQKIZZEIKBRFO-UHFFFAOYSA-N 0.000 claims 1
- LMIWUTKCGKCAPR-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 LMIWUTKCGKCAPR-UHFFFAOYSA-N 0.000 claims 1
- NAJJOZBHQMYRCQ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)pyrrolo[3,2-b]pyridin-3-yl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=CN1C(=O)C1=C(Cl)C=CC=C1C1CC1 NAJJOZBHQMYRCQ-UHFFFAOYSA-N 0.000 claims 1
- XQLORDGAAKKHJV-UHFFFAOYSA-N 4-[1-(2-chloro-6-methyl-4-morpholin-4-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC(N2CCOCC2)=CC(Cl)=C1C(=O)N(C1=CC=CN=C11)N=C1C1=CC=C(C(O)=O)C=C1F XQLORDGAAKKHJV-UHFFFAOYSA-N 0.000 claims 1
- MRUIGUAOGXKSOD-UHFFFAOYSA-N 4-[1-(2-chloro-6-morpholin-4-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1N1CCOCC1 MRUIGUAOGXKSOD-UHFFFAOYSA-N 0.000 claims 1
- STTDKBXVHRDKSV-UHFFFAOYSA-N 4-[1-(2-chloro-6-prop-1-en-2-ylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC(=C)C1=CC=CC(Cl)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 STTDKBXVHRDKSV-UHFFFAOYSA-N 0.000 claims 1
- SZTKTFVKDORSMX-UHFFFAOYSA-N 4-[1-(4-amino-2-chloro-6-methylbenzoyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC(N)=CC(Cl)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 SZTKTFVKDORSMX-UHFFFAOYSA-N 0.000 claims 1
- ULGRACMCPGVEEK-UHFFFAOYSA-N 4-[1-(6-chloro-2,3-dihydro-1,4-benzodioxine-5-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC2=C1OCCO2 ULGRACMCPGVEEK-UHFFFAOYSA-N 0.000 claims 1
- ULWLHAACQVHNPR-UHFFFAOYSA-N 4-[1-[2-(dimethylamino)-6-methylbenzoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound CN(C)C1=CC=CC(C)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 ULWLHAACQVHNPR-UHFFFAOYSA-N 0.000 claims 1
- OEJKIMIEMMNCSZ-UHFFFAOYSA-N 4-[1-[2-chloro-4-(2-methoxyethoxy)-6-methylbenzoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound ClC1=CC(OCCOC)=CC(C)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 OEJKIMIEMMNCSZ-UHFFFAOYSA-N 0.000 claims 1
- BIUDEVDBTBYDTN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-2-methylindol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC=CC=C2N(C(=O)C=2C(=CC=CC=2Cl)C(F)(F)F)C(C)=C1C1=CC=C(C(O)=O)C=C1F BIUDEVDBTBYDTN-UHFFFAOYSA-N 0.000 claims 1
- IIYPHUTYQFNHTA-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-formylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(C=O)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F IIYPHUTYQFNHTA-UHFFFAOYSA-N 0.000 claims 1
- LDWYFJQKADHORK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-5-(methylamino)pyrrolo[2,3-c]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C1=2C=NC(NC)=CC=2C(C=2C(=CC(=CC=2)C(O)=O)F)=CN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F LDWYFJQKADHORK-UHFFFAOYSA-N 0.000 claims 1
- ZAFJKTHLHAQPER-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-5-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[2,3-c]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C1=2C=NC(NC(=O)OC(C)(C)C)=CC=2C(C=2C(=CC(=CC=2)C(O)=O)F)=CN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZAFJKTHLHAQPER-UHFFFAOYSA-N 0.000 claims 1
- VWLWIRYLQWWKSU-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazinane-3-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)N2COCCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F VWLWIRYLQWWKSU-UHFFFAOYSA-N 0.000 claims 1
- MUIQMFMWWHLGBL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazol-2-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2OC=CN=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F MUIQMFMWWHLGBL-UHFFFAOYSA-N 0.000 claims 1
- NTVUUWMYIXCQPR-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazole-2-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)C=2OC=CN=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F NTVUUWMYIXCQPR-UHFFFAOYSA-N 0.000 claims 1
- ZXYDLCCOBGDIMX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-oxazolidine-3-carbonyl)pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=NC=C(C=C11)C(=O)N2COCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZXYDLCCOBGDIMX-UHFFFAOYSA-N 0.000 claims 1
- SOLIBFAOUSRRQU-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-thiazol-4-yl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2N=CSC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F SOLIBFAOUSRRQU-UHFFFAOYSA-N 0.000 claims 1
- JJOYOICIYBODAK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1,3-thiazol-5-yl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2SC=NC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JJOYOICIYBODAK-UHFFFAOYSA-N 0.000 claims 1
- NACDHOZIQUKVIW-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-2-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CN1C=CN=C1C1=CC=C(C(=NN2C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=CC=3)C(O)=O)F)C2=C1 NACDHOZIQUKVIW-UHFFFAOYSA-N 0.000 claims 1
- FLOCZDVOIMRSCY-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-4-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound CN1C=NC(C=2C=C3N(C(=O)C=4C(=CC=CC=4Cl)C(F)(F)F)N=C(C3=CC=2)C=2C(=CC(=CC=2)C(O)=O)F)=C1 FLOCZDVOIMRSCY-UHFFFAOYSA-N 0.000 claims 1
- AOMVCSGXIXOKEM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(1-methylimidazol-4-yl)indazol-3-yl]benzoic acid Chemical compound CN1C=NC(C=2C=C3N(C(=O)C=4C(=CC=CC=4Cl)C(F)(F)F)N=C(C3=CC=2)C=2C=CC(=CC=2)C(O)=O)=C1 AOMVCSGXIXOKEM-UHFFFAOYSA-N 0.000 claims 1
- YNUXZWMHLUWWNJ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2,5-dioxoimidazolidin-4-yl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C2C(NC(=O)N2)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F YNUXZWMHLUWWNJ-UHFFFAOYSA-N 0.000 claims 1
- DAEJUPFLIPARNN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-cyanophenyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C=2C(=CC=CC=2)C#N)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DAEJUPFLIPARNN-UHFFFAOYSA-N 0.000 claims 1
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- WHGQARDUXBSUDH-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[(2-methylpropan-2-yl)oxycarbonylamino]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(NC(=O)OC(C)(C)C)=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WHGQARDUXBSUDH-UHFFFAOYSA-N 0.000 claims 1
- FYCDYBZKAVRDMF-GASCZTMLSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[(2r,6s)-2,6-dimethylmorpholine-4-carbonyl]indazol-3-yl]-3-fluorobenzoic acid Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(C(=NN2C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=CC=3)C(O)=O)F)C2=C1 FYCDYBZKAVRDMF-GASCZTMLSA-N 0.000 claims 1
- IAHCCNRIJKPZTM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[2-(dimethylamino)-2-oxoethyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(CC(=O)N(C)C)=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F IAHCCNRIJKPZTM-UHFFFAOYSA-N 0.000 claims 1
- FBVPAOCGDMHZAL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[2-(methylamino)-2-oxoethyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(CC(=O)NC)=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F FBVPAOCGDMHZAL-UHFFFAOYSA-N 0.000 claims 1
- DBLOLXXKJOBMTA-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[5-(hydroxymethyl)-1,3-oxazol-2-yl]indazol-3-yl]-3-fluorobenzoic acid Chemical compound O1C(CO)=CN=C1C1=CC=C(C(=NN2C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C=3C(=CC(=CC=3)C(O)=O)F)C2=C1 DBLOLXXKJOBMTA-UHFFFAOYSA-N 0.000 claims 1
- MHRAJUWMBYVALM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[cyclopropyl(hydroxy)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(O)C1CC1 MHRAJUWMBYVALM-UHFFFAOYSA-N 0.000 claims 1
- KPPSRVSRXSXIEN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[cyclopropyl(methyl)carbamoyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(=O)N(C)C1CC1 KPPSRVSRXSXIEN-UHFFFAOYSA-N 0.000 claims 1
- WDPHOVASCHHXHY-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[hydroxy(1,3-oxazol-2-yl)methyl]pyrazolo[4,3-b]pyridin-3-yl]-3-fluorobenzoic acid Chemical compound C=1N=C2C(C=3C(=CC(=CC=3)C(O)=O)F)=NN(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)C2=CC=1C(O)C1=NC=CO1 WDPHOVASCHHXHY-UHFFFAOYSA-N 0.000 claims 1
- PLUSZQBSIICZOQ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[methyl(methylcarbamoyl)amino]indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(N(C)C(=O)NC)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F PLUSZQBSIICZOQ-UHFFFAOYSA-N 0.000 claims 1
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| US9809561B2 (en) | 2013-12-20 | 2017-11-07 | Merck Sharp & Dohme Corp. | Tetrahydronaphthyridine, benzoxazine, aza-benzoxazine and related bicyclic compounds for inhibition of RORgamma activity and the treatment of disease |
| KR102408261B1 (ko) | 2014-02-03 | 2022-06-10 | 비타이 파마슈티컬즈, 엘엘씨 | Ror-감마의 디하이드로피롤로피리딘 저해제 |
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| WO2015139621A1 (zh) * | 2014-03-18 | 2015-09-24 | 北京韩美药品有限公司 | 4-杂芳基取代的苯甲酸或苯甲酰胺类化合物 |
| 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 |
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| TW201617314A (zh) * | 2014-09-10 | 2016-05-16 | 第一三共股份有限公司 | 羧酸衍生物 |
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| UA118989C2 (uk) * | 2014-10-14 | 2019-04-10 | Вітае Фармасьютікалс, Інк. | Дигідропіролопіридинові інгібітори ror-гамма |
| GB201419015D0 (en) | 2014-10-24 | 2014-12-10 | Orca Pharmaceuticals Ltd | Compounds |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| CA2973185C (en) * | 2015-01-08 | 2021-02-16 | Advinus Therapeutics Limited | Bridgehead nitrogen bicyclic inhibitors/modulators of retinoic acid-related orphan receptor gamma (ror.gamma.) |
| EP3256450B1 (en) * | 2015-02-11 | 2020-12-02 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as ror-gamma-t inhibitors and uses thereof |
| CN107614062A (zh) | 2015-03-12 | 2018-01-19 | 加利福尼亚大学董事会 | 用RORγ抑制剂治疗癌症的方法 |
| 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 |
| KR20180025894A (ko) | 2015-06-11 | 2018-03-09 | 라이세라 코퍼레이션 | Rory의 작용제로서 사용하기 위한 아릴 디히드로-2h-벤조[b][1,4]옥사진 술폰아미드 및 관련 화합물 및 질환의 치료 |
| EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| EP3353179B1 (en) * | 2015-09-21 | 2022-02-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| AU2016344118A1 (en) * | 2015-10-27 | 2018-05-10 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| RU2018117503A (ru) * | 2015-10-27 | 2019-11-28 | Мерк Шарп И Доум Корп. | ЗАМЕЩЕННЫЕ ИНДАЗОЛЬНЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ RORγТ И ИХ ПРИМЕНЕНИЕ |
| 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 |
| KR20180086221A (ko) | 2015-11-20 | 2018-07-30 | 비타이 파마슈티컬즈, 인코포레이티드 | Ror-감마의 조절물질 |
| AU2017208998B2 (en) * | 2016-01-21 | 2021-07-15 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | 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 |
| CN109789146B (zh) | 2016-07-29 | 2023-04-18 | 拉普特医疗公司 | 趋化因子受体调节剂及其用途 |
| US11628159B2 (en) | 2017-01-10 | 2023-04-18 | Eth Zurich | Cell-protective compounds and their use |
| US11242335B2 (en) | 2017-04-11 | 2022-02-08 | Sunshine Lake Pharma Co., Ltd. | Fluorine-substituted indazole compounds and uses thereof |
| WO2018219797A1 (en) | 2017-06-02 | 2018-12-06 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| IL298639A (en) | 2017-07-24 | 2023-01-01 | Vitae Pharmaceuticals Llc | Inhibitors of gamma ror |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| UY38144A (es) | 2018-03-12 | 2019-10-31 | Abbvie Inc | Inhibidores de la señalización mediada por tirosina cinasa |
| GB201811825D0 (en) * | 2018-07-19 | 2018-09-05 | Benevolentai Bio Ltd | Organic compounds |
| AU2021245397A1 (en) * | 2020-03-31 | 2022-10-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| CN117043162A (zh) * | 2021-05-19 | 2023-11-10 | 迈巴制药(南京)有限公司 | Tyk2选择性抑制剂及其用途 |
| TW202345809A (zh) | 2022-03-23 | 2023-12-01 | 美商愛德亞生物科學公司 | 作為parg抑制劑之經哌取代的吲唑化合物 |
Family Cites Families (37)
| 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 |
| 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 |
| 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 |
| BRPI0514017A (pt) | 2004-08-03 | 2008-05-27 | Wyeth Corp | indazóis úteis no tratamento de doenças cardiovasculares |
| CA2583428A1 (en) | 2004-09-03 | 2006-03-09 | Plexxikon, Inc. | Bicyclic heteroaryl pde4b inhibitors |
| SE0402762D0 (sv) | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
| 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 |
| US7696229B2 (en) | 2006-02-17 | 2010-04-13 | 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 |
| WO2007103308A2 (en) | 2006-03-07 | 2007-09-13 | Array Biopharma Inc. | Heterobicyclic pyrazole compounds and methods of use |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| PL2134685T3 (pl) | 2007-04-16 | 2016-02-29 | Abbvie Inc | Pochodne indolu niepodstawione w pozycji 7 jako inhibitory Mcl-1 |
| 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 |
| EP2155722B1 (en) | 2007-06-05 | 2013-08-14 | Merck Sharp & Dohme Corp. | Polycyclic indazole derivatives and their use as erk inhibitors for the treatment of cancer |
| US20100317863A1 (en) | 2007-07-25 | 2010-12-16 | Boehringer Ingelheim International Gmbh | Glucocorticoid Mimetics, Methods of Making Them, Pharmaceutical Compositions and Uses Thereof |
| 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 |
| AU2010330894A1 (en) | 2009-12-18 | 2012-07-05 | Janssen Pharmaceutica Nv | Substituted aminothiazolone indazoles as estrogen related receptor-aalpha 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 |
| US9512111B2 (en) | 2010-11-08 | 2016-12-06 | Lycera Corporation | N-sulfonylated tetrahydroquinolines and related bicyclic compounds for inhibition of RORγ activity and the treatment of disease |
| KR20120063283A (ko) | 2010-12-07 | 2012-06-15 | 제일약품주식회사 | 신규한 피라졸로 피리딘 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| RU2620376C2 (ru) | 2010-12-22 | 2017-05-25 | Людвиг-Максимилианс-Университэт Мюнхен | Цинкорганические комплексы, способы их получения и применение |
| 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 |
| 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 |
| WO2014026327A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 4-heteroaryl substituted benzoic acid compounds as rorgammat inhibitors and uses thereof |
| WO2014026329A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | N-alkylated indole and indazole compounds as rorgammat inhibitors and uses thereof |
-
2012
- 2012-08-15 WO PCT/CN2012/080131 patent/WO2014026327A1/en not_active Ceased
-
2013
- 2013-08-14 WO PCT/US2013/054887 patent/WO2014028589A2/en not_active Ceased
- 2013-08-14 KR KR1020157006322A patent/KR20150042266A/ko not_active Withdrawn
- 2013-08-14 MX MX2015001941A patent/MX2015001941A/es unknown
- 2013-08-14 CA CA2881688A patent/CA2881688A1/en not_active Abandoned
- 2013-08-14 JP JP2015527566A patent/JP6422438B2/ja not_active Expired - Fee Related
- 2013-08-14 BR BR112015003188A patent/BR112015003188A2/pt not_active IP Right Cessation
- 2013-08-14 US US14/421,048 patent/US9745265B2/en active Active
- 2013-08-14 AU AU2013302725A patent/AU2013302725A1/en not_active Abandoned
- 2013-08-14 RU RU2015108894A patent/RU2015108894A/ru unknown
- 2013-08-14 EP EP13829282.6A patent/EP2884981B1/en active Active
-
2015
- 2015-02-12 IN IN1156DEN2015 patent/IN2015DN01156A/en unknown
-
2017
- 2017-07-12 US US15/647,437 patent/US10196354B2/en active Active
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