JP2014509316A5 - - Google Patents
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- Publication number
- JP2014509316A5 JP2014509316A5 JP2013552823A JP2013552823A JP2014509316A5 JP 2014509316 A5 JP2014509316 A5 JP 2014509316A5 JP 2013552823 A JP2013552823 A JP 2013552823A JP 2013552823 A JP2013552823 A JP 2013552823A JP 2014509316 A5 JP2014509316 A5 JP 2014509316A5
- Authority
- JP
- Japan
- Prior art keywords
- indazol
- chloro
- trifluoromethyl
- benzoyl
- benzoic acid
- 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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- -1 nitro, hydroxy Chemical group 0.000 claims description 21
- DMVNHZZYMKLYHU-UHFFFAOYSA-N 4-[1-(2-cyanophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)C#N)C2=CC=CC=C12 DMVNHZZYMKLYHU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- HCVYKPCTDSMHCB-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F HCVYKPCTDSMHCB-UHFFFAOYSA-N 0.000 claims 2
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-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
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- PXYGPIOPCBREPC-UHFFFAOYSA-N (2,3-dichlorophenyl)-[3-[4-(2h-tetrazol-5-yl)phenyl]indazol-1-yl]methanone Chemical compound ClC1=CC=CC(C(=O)N2C3=CC=CC=C3C(C=3C=CC(=CC=3)C=3NN=NN=3)=N2)=C1Cl PXYGPIOPCBREPC-UHFFFAOYSA-N 0.000 claims 1
- WYCZCJSLFZGBDD-UHFFFAOYSA-N (2,6-dichlorophenyl)-[3-[4-(2h-tetrazol-5-yl)phenyl]indazol-1-yl]methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2NN=NN=2)=N1 WYCZCJSLFZGBDD-UHFFFAOYSA-N 0.000 claims 1
- DZKCUOINIDGQAO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[4-[1-[2-(trifluoromethyl)phenyl]sulfonylindazol-3-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)C2=CC=CC=C12 DZKCUOINIDGQAO-UHFFFAOYSA-N 0.000 claims 1
- HIECFBLIELCFCU-UHFFFAOYSA-N 1-(2-bromo-4-fluorophenyl)sulfonyl-3-[4-(2h-tetrazol-5-yl)phenyl]indazole Chemical compound BrC1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2NN=NN=2)=N1 HIECFBLIELCFCU-UHFFFAOYSA-N 0.000 claims 1
- OFIOGQHBYRFBNL-UHFFFAOYSA-N 1-(3-bromo-5-chlorothiophen-2-yl)sulfonyl-3-[4-(2h-tetrazol-5-yl)phenyl]indazole Chemical compound S1C(Cl)=CC(Br)=C1S(=O)(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2NN=NN=2)=N1 OFIOGQHBYRFBNL-UHFFFAOYSA-N 0.000 claims 1
- JBDVAMKBNHYPFP-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-3-[4-(2h-tetrazol-5-yl)phenyl]indazole Chemical compound ClC1=CC=CC(S(=O)(=O)N2C3=CC=CC=C3C(C=3C=CC(=CC=3)C=3NN=NN=3)=N2)=C1 JBDVAMKBNHYPFP-UHFFFAOYSA-N 0.000 claims 1
- XQAZEEJERSCXMR-UHFFFAOYSA-N 1-[2-chloro-6-(trifluoromethyl)benzoyl]-3-(4-methoxycarbonylphenyl)indazole-6-carboxylic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C(C1=CC=C(C=C11)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F XQAZEEJERSCXMR-UHFFFAOYSA-N 0.000 claims 1
- RAMINHQMDKAQJK-UHFFFAOYSA-N 2-[3-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 RAMINHQMDKAQJK-UHFFFAOYSA-N 0.000 claims 1
- NHNSOLXSBZAMSC-UHFFFAOYSA-N 2-[4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F NHNSOLXSBZAMSC-UHFFFAOYSA-N 0.000 claims 1
- WRMOWVSDUIFHLL-UHFFFAOYSA-N 2-[4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]pyrazolo[4,3-b]pyridin-3-yl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WRMOWVSDUIFHLL-UHFFFAOYSA-N 0.000 claims 1
- QRKXIOBGGXTFBQ-UHFFFAOYSA-N 2-acetyloxy-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 QRKXIOBGGXTFBQ-UHFFFAOYSA-N 0.000 claims 1
- SBFUCWPEOIMBNG-UHFFFAOYSA-N 2-acetyloxy-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC(C=2C3=NC=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 SBFUCWPEOIMBNG-UHFFFAOYSA-N 0.000 claims 1
- OKIIXRZTHUQZKQ-UHFFFAOYSA-N 2-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-5-fluorobenzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(F)=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F OKIIXRZTHUQZKQ-UHFFFAOYSA-N 0.000 claims 1
- JOYBYDMIKBONLP-UHFFFAOYSA-N 2-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JOYBYDMIKBONLP-UHFFFAOYSA-N 0.000 claims 1
- NBOMNRQMPHHFHD-UHFFFAOYSA-N 2-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]pyrazolo[4,3-b]pyridin-3-yl]-5-fluorobenzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(F)=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F NBOMNRQMPHHFHD-UHFFFAOYSA-N 0.000 claims 1
- UJWYJYMPIIEMCI-UHFFFAOYSA-N 3,5-dimethyl-4-[3-[4-(2h-tetrazol-5-yl)phenyl]indazol-1-yl]sulfonyl-1,2-oxazole Chemical compound CC1=NOC(C)=C1S(=O)(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2NN=NN=2)=N1 UJWYJYMPIIEMCI-UHFFFAOYSA-N 0.000 claims 1
- YRNXBQVLKNQKJV-UHFFFAOYSA-N 3-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 YRNXBQVLKNQKJV-UHFFFAOYSA-N 0.000 claims 1
- YNHTWUSPSNPPGC-UHFFFAOYSA-N 3-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-hydroxyethylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)NCCO)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)Cl)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F YNHTWUSPSNPPGC-UHFFFAOYSA-N 0.000 claims 1
- RPMORZDGRFNBRS-UHFFFAOYSA-N 3-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(dimethylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)N(C)C)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)Cl)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F RPMORZDGRFNBRS-UHFFFAOYSA-N 0.000 claims 1
- DGBMGFMYSDUCRS-UHFFFAOYSA-N 3-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DGBMGFMYSDUCRS-UHFFFAOYSA-N 0.000 claims 1
- JVMMADIELFSJFP-UHFFFAOYSA-N 3-chloro-4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JVMMADIELFSJFP-UHFFFAOYSA-N 0.000 claims 1
- KTCDQVHDKAELLY-UHFFFAOYSA-N 3-fluoro-4-[1-(2-fluoro-6-methoxybenzoyl)indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=CC=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 KTCDQVHDKAELLY-UHFFFAOYSA-N 0.000 claims 1
- GFCRKHBJSXCOKY-UHFFFAOYSA-N 3-fluoro-4-[1-(2-fluoro-6-methoxybenzoyl)pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=CC=CN=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 GFCRKHBJSXCOKY-UHFFFAOYSA-N 0.000 claims 1
- QSKUMOHWHFBEED-UHFFFAOYSA-N 3-fluoro-4-[4-fluoro-1-(2-fluoro-6-methoxybenzoyl)indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=CC=CC(F)=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 QSKUMOHWHFBEED-UHFFFAOYSA-N 0.000 claims 1
- BSLVSOOJJHNDAM-UHFFFAOYSA-N 3-fluoro-4-[7-fluoro-1-(2-fluoro-6-methoxybenzoyl)indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=C(F)C=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=N1 BSLVSOOJJHNDAM-UHFFFAOYSA-N 0.000 claims 1
- PEQDJFFHHIZJNF-UHFFFAOYSA-N 4-(1-naphthalen-1-ylsulfonylindazol-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC=CC=C12 PEQDJFFHHIZJNF-UHFFFAOYSA-N 0.000 claims 1
- CNLZQQYAISWKHY-UHFFFAOYSA-N 4-(1-quinolin-8-ylsulfonylindazol-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C2=CC=CC=C12 CNLZQQYAISWKHY-UHFFFAOYSA-N 0.000 claims 1
- AVGUEXUHUPSTLJ-UHFFFAOYSA-N 4-[1-(2,1,3-benzoxadiazol-4-ylsulfonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C3=NON=C3C=CC=2)C2=CC=CC=C12 AVGUEXUHUPSTLJ-UHFFFAOYSA-N 0.000 claims 1
- MTKJHQXUECKDOI-UHFFFAOYSA-N 4-[1-(2,3,4-trichlorophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)C2=CC=CC=C12 MTKJHQXUECKDOI-UHFFFAOYSA-N 0.000 claims 1
- RQEHXXGTIUCAKD-UHFFFAOYSA-N 4-[1-(2,3-dichlorobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC(Cl)=C1Cl RQEHXXGTIUCAKD-UHFFFAOYSA-N 0.000 claims 1
- UTPBZEFICGRPAT-UHFFFAOYSA-N 4-[1-(2,3-dichlorophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)C2=CC=CC=C12 UTPBZEFICGRPAT-UHFFFAOYSA-N 0.000 claims 1
- LZWFKNCYDFBCIJ-UHFFFAOYSA-N 4-[1-(2,4,6-trichlorobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=C(Cl)C=C1Cl LZWFKNCYDFBCIJ-UHFFFAOYSA-N 0.000 claims 1
- OVLLJXFDKBZBPK-UHFFFAOYSA-N 4-[1-(2,5-dichlorophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)C2=CC=CC=C12 OVLLJXFDKBZBPK-UHFFFAOYSA-N 0.000 claims 1
- NEZILFWWNWEUMD-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)-4-fluoroindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl NEZILFWWNWEUMD-UHFFFAOYSA-N 0.000 claims 1
- FGTNCKUVEIEXGG-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)-5-fluoroindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC(F)=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl FGTNCKUVEIEXGG-UHFFFAOYSA-N 0.000 claims 1
- RZXYNOQSMNICHA-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)-6-fluoroindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(F)C=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl RZXYNOQSMNICHA-UHFFFAOYSA-N 0.000 claims 1
- HZLVLWXSRRDXNZ-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)-7-fluoroindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC(F)=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl HZLVLWXSRRDXNZ-UHFFFAOYSA-N 0.000 claims 1
- YRLYJWZLPGDXGP-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl YRLYJWZLPGDXGP-UHFFFAOYSA-N 0.000 claims 1
- PCCSYLMXPNKMER-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl PCCSYLMXPNKMER-UHFFFAOYSA-N 0.000 claims 1
- DWSDIJFPGXVVDL-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)pyrazolo[4,3-c]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CN=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Cl DWSDIJFPGXVVDL-UHFFFAOYSA-N 0.000 claims 1
- RMRLLAPEYLCVMB-UHFFFAOYSA-N 4-[1-(2,6-dichlorobenzoyl)pyrrolo[3,2-b]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=CN1C(=O)C1=C(Cl)C=CC=C1Cl RMRLLAPEYLCVMB-UHFFFAOYSA-N 0.000 claims 1
- KVMHZJKRRYQVLN-UHFFFAOYSA-N 4-[1-(2,6-dichlorophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2Cl)Cl)C2=CC=CC=C12 KVMHZJKRRYQVLN-UHFFFAOYSA-N 0.000 claims 1
- IPVAXIUJHXJPFN-UHFFFAOYSA-N 4-[1-(2,6-dimethylbenzoyl)indazol-3-yl]benzoic acid Chemical compound CC1=CC=CC(C)=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 IPVAXIUJHXJPFN-UHFFFAOYSA-N 0.000 claims 1
- LYRZUBSDODNYOV-UHFFFAOYSA-N 4-[1-(2-bromo-6-chlorobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1Br LYRZUBSDODNYOV-UHFFFAOYSA-N 0.000 claims 1
- GUQXYEUEVSDMNA-UHFFFAOYSA-N 4-[1-(2-bromobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC=C1Br GUQXYEUEVSDMNA-UHFFFAOYSA-N 0.000 claims 1
- BMEPBRVHHVMKBA-UHFFFAOYSA-N 4-[1-(2-bromophenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 BMEPBRVHHVMKBA-UHFFFAOYSA-N 0.000 claims 1
- LONUHOULXYUWOQ-UHFFFAOYSA-N 4-[1-(2-chlorobenzoyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC=C1Cl LONUHOULXYUWOQ-UHFFFAOYSA-N 0.000 claims 1
- FDXIBNODHPRAKX-UHFFFAOYSA-N 4-[1-(2-chlorophenyl)sulfonylpyrazolo[4,3-c]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)Cl)C2=CC=NC=C12 FDXIBNODHPRAKX-UHFFFAOYSA-N 0.000 claims 1
- YIYPBAIVNNJXOU-UHFFFAOYSA-N 4-[1-(2-cyano-5-methylphenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound CC1=CC=C(C#N)C(S(=O)(=O)N2C3=CC=CC=C3C(C=3C=CC(=CC=3)C(O)=O)=N2)=C1 YIYPBAIVNNJXOU-UHFFFAOYSA-N 0.000 claims 1
- OVENOHQCRGGJAL-UHFFFAOYSA-N 4-[1-(2-ethoxybenzoyl)indazol-3-yl]benzoic acid Chemical compound CCOC1=CC=CC=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 OVENOHQCRGGJAL-UHFFFAOYSA-N 0.000 claims 1
- LSOLHRBVLYQDFJ-UHFFFAOYSA-N 4-[1-(2-fluoro-6-methoxybenzoyl)indazol-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 LSOLHRBVLYQDFJ-UHFFFAOYSA-N 0.000 claims 1
- GFZPIRKNDAWCKV-UHFFFAOYSA-N 4-[1-(2-fluoro-6-methoxybenzoyl)pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound COC1=CC=CC(F)=C1C(=O)N1C2=CC=CN=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 GFZPIRKNDAWCKV-UHFFFAOYSA-N 0.000 claims 1
- JLCIXQPSVRKXKF-UHFFFAOYSA-N 4-[1-(2-methoxycarbonylbenzoyl)indazol-3-yl]benzoic acid Chemical compound COC(=O)C1=CC=CC=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 JLCIXQPSVRKXKF-UHFFFAOYSA-N 0.000 claims 1
- KTPWAYLITUPDPD-UHFFFAOYSA-N 4-[1-(2-methyl-6-nitrobenzoyl)indazol-3-yl]benzoic acid Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 KTPWAYLITUPDPD-UHFFFAOYSA-N 0.000 claims 1
- FXYZBHMAULFDAD-UHFFFAOYSA-N 4-[1-(3,5-dichloropyridine-4-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=NC=C1Cl FXYZBHMAULFDAD-UHFFFAOYSA-N 0.000 claims 1
- VCCBFIZVNUDKCM-UHFFFAOYSA-N 4-[1-(3,5-dimethylphenyl)sulfonylindazol-3-yl]-2-(trifluoromethyl)benzoic acid Chemical compound CC1=CC(C)=CC(S(=O)(=O)N2C3=CC=CC=C3C(C=3C=C(C(C(O)=O)=CC=3)C(F)(F)F)=N2)=C1 VCCBFIZVNUDKCM-UHFFFAOYSA-N 0.000 claims 1
- IKYIORIILIVUMR-UHFFFAOYSA-N 4-[1-(3,5-dimethylphenyl)sulfonylindazol-3-yl]-3-fluorobenzoic acid Chemical compound CC1=CC(C)=CC(S(=O)(=O)N2C3=CC=CC=C3C(C=3C(=CC(=CC=3)C(O)=O)F)=N2)=C1 IKYIORIILIVUMR-UHFFFAOYSA-N 0.000 claims 1
- PAFOPTUTKPDSLM-UHFFFAOYSA-N 4-[1-(3-chloro-2-methylphenyl)sulfonylindazol-3-yl]benzoic acid Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=N1 PAFOPTUTKPDSLM-UHFFFAOYSA-N 0.000 claims 1
- ZMLMBQCHASQVQR-UHFFFAOYSA-N 4-[1-(cyclohexanecarbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1CCCCC1 ZMLMBQCHASQVQR-UHFFFAOYSA-N 0.000 claims 1
- RYGDYFKMRVNQJQ-UHFFFAOYSA-N 4-[1-[2-(trifluoromethoxy)phenyl]sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)F)C2=CC=CC=C12 RYGDYFKMRVNQJQ-UHFFFAOYSA-N 0.000 claims 1
- ITGRYFRJMJBLPN-UHFFFAOYSA-N 4-[1-[2-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=CC=CC=C1C(F)(F)F ITGRYFRJMJBLPN-UHFFFAOYSA-N 0.000 claims 1
- QBHSVSDBFDYCRG-UHFFFAOYSA-N 4-[1-[2-(trifluoromethyl)benzoyl]pyrazolo[4,3-b]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=NC=CC=C11)=NN1C(=O)C1=CC=CC=C1C(F)(F)F QBHSVSDBFDYCRG-UHFFFAOYSA-N 0.000 claims 1
- MYKGDAQLKXYOHF-UHFFFAOYSA-N 4-[1-[2-(trifluoromethyl)phenyl]sulfonylindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN(S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)C2=CC=CC=C12 MYKGDAQLKXYOHF-UHFFFAOYSA-N 0.000 claims 1
- WEWIXJKLJWKDND-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-(trifluoromethyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(C=CC=C11)C(F)(F)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WEWIXJKLJWKDND-UHFFFAOYSA-N 0.000 claims 1
- OAHVYZFWMWGOSU-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoro-6-hydroxyindazol-3-yl]-3-fluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=C(O)C=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F OAHVYZFWMWGOSU-UHFFFAOYSA-N 0.000 claims 1
- JWHHHJJIHHFYOF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoro-6-hydroxyindazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=C(F)C=C(O)C=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JWHHHJJIHHFYOF-UHFFFAOYSA-N 0.000 claims 1
- IHYGKWLBDHBDOK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoro-6-methoxyindazol-3-yl]benzoic acid Chemical compound C12=CC(OC)=CC(F)=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F IHYGKWLBDHBDOK-UHFFFAOYSA-N 0.000 claims 1
- ZDDZWHCRQVHUHX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2,3-difluorobenzoic acid Chemical compound FC1=C(F)C(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZDDZWHCRQVHUHX-UHFFFAOYSA-N 0.000 claims 1
- DKQNHVALVAMVFQ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-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)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DKQNHVALVAMVFQ-UHFFFAOYSA-N 0.000 claims 1
- RZGWDVZYMKPEJD-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2,6-difluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=C(F)C=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F RZGWDVZYMKPEJD-UHFFFAOYSA-N 0.000 claims 1
- XQVGCZOOWAZKMD-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-cyanobenzoic acid Chemical compound C1=C(C#N)C(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F XQVGCZOOWAZKMD-UHFFFAOYSA-N 0.000 claims 1
- DFAVWTGRYXEZCF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-fluoro-5-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=C(F)C=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DFAVWTGRYXEZCF-UHFFFAOYSA-N 0.000 claims 1
- JCUFIUVKIKYPFI-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-fluoro-6-hydroxybenzoic acid Chemical compound C1=C(F)C(C(=O)O)=C(O)C=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JCUFIUVKIKYPFI-UHFFFAOYSA-N 0.000 claims 1
- DFIYJQBWWHRCQB-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DFIYJQBWWHRCQB-UHFFFAOYSA-N 0.000 claims 1
- NGAINXNNYFXZPH-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 NGAINXNNYFXZPH-UHFFFAOYSA-N 0.000 claims 1
- IAEPRBMJGSMPPQ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 IAEPRBMJGSMPPQ-UHFFFAOYSA-N 0.000 claims 1
- AAEWPNUFYBXUBS-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-2-propan-2-ylbenzoic acid Chemical compound C1=C(C(O)=O)C(C(C)C)=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1 AAEWPNUFYBXUBS-UHFFFAOYSA-N 0.000 claims 1
- ZNVMVGGDEKBSJL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-3,5-dimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ZNVMVGGDEKBSJL-UHFFFAOYSA-N 0.000 claims 1
- WXYSMKILSMKDMX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-3,6-difluoro-2-hydroxybenzoic acid Chemical compound FC1=C(O)C(C(=O)O)=C(F)C=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WXYSMKILSMKDMX-UHFFFAOYSA-N 0.000 claims 1
- PFVOSXMQCIFOSO-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-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=C1C(F)(F)F PFVOSXMQCIFOSO-UHFFFAOYSA-N 0.000 claims 1
- GQVOUMFKJQIGDN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-3-hydroxybenzoic acid Chemical compound OC1=CC(C(=O)O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F GQVOUMFKJQIGDN-UHFFFAOYSA-N 0.000 claims 1
- STQXKJOFHRMJSB-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F STQXKJOFHRMJSB-UHFFFAOYSA-N 0.000 claims 1
- BJJJSCVVTZEACN-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F BJJJSCVVTZEACN-UHFFFAOYSA-N 0.000 claims 1
- WVXZHSXMGDRAGP-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-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)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WVXZHSXMGDRAGP-UHFFFAOYSA-N 0.000 claims 1
- ICNODFKWCGRHEV-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-4-fluoroindazol-3-yl]-5-fluoro-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(C=2C3=C(F)C=CC=C3N(C(=O)C=3C(=CC=CC=3Cl)C(F)(F)F)N=2)=C1F ICNODFKWCGRHEV-UHFFFAOYSA-N 0.000 claims 1
- JENSMWFEAMWDDZ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-hydroxyethylcarbamoyl)indazol-3-yl]-2-fluorobenzoic acid Chemical compound C12=CC(C(=O)NCCO)=CC=C2C(C=2C=C(F)C(C(O)=O)=CC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F JENSMWFEAMWDDZ-UHFFFAOYSA-N 0.000 claims 1
- UYMZHJXJONTSOA-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-hydroxyethylcarbamoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(C(=O)NCCO)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F UYMZHJXJONTSOA-UHFFFAOYSA-N 0.000 claims 1
- WYFVOOFOMUVMII-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-hydroxyethylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)NCCO)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F WYFVOOFOMUVMII-UHFFFAOYSA-N 0.000 claims 1
- PLLRXVZWFUTOTO-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(2-hydroxypropylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)NCC(O)C)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F PLLRXVZWFUTOTO-UHFFFAOYSA-N 0.000 claims 1
- VQKDVIDEPGKBSX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(3,3-difluoroazetidine-1-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(=O)N2CC(F)(F)C2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F VQKDVIDEPGKBSX-UHFFFAOYSA-N 0.000 claims 1
- AKGIWQUIIOWIAL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(3-fluoroazetidine-1-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(=O)N2CC(F)C2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F AKGIWQUIIOWIAL-UHFFFAOYSA-N 0.000 claims 1
- PCMYBUALWFAPMF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(3-hydroxypropylcarbamoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(C(=O)NCCCO)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F PCMYBUALWFAPMF-UHFFFAOYSA-N 0.000 claims 1
- TZLUXRUJGWIEMH-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(3-hydroxypropylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)NCCCO)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F TZLUXRUJGWIEMH-UHFFFAOYSA-N 0.000 claims 1
- UKSQVCJXNVINIS-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(3-methoxypropylcarbamoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(C(=O)NCCCOC)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F UKSQVCJXNVINIS-UHFFFAOYSA-N 0.000 claims 1
- ASIJDBFRMZAUIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(4-hydroxybutylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)NCCCCO)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F ASIJDBFRMZAUIX-UHFFFAOYSA-N 0.000 claims 1
- PFTJICKKUCIOSE-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(dimethylcarbamoyl)indazol-3-yl]-2-fluorobenzoic acid Chemical compound C12=CC(C(=O)N(C)C)=CC=C2C(C=2C=C(F)C(C(O)=O)=CC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F PFTJICKKUCIOSE-UHFFFAOYSA-N 0.000 claims 1
- YFXXYJKIRBQOOM-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(dimethylcarbamoyl)indazol-3-yl]-2-hydroxybenzoic acid Chemical compound C12=CC(C(=O)N(C)C)=CC=C2C(C=2C=C(O)C(C(O)=O)=CC=2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F YFXXYJKIRBQOOM-UHFFFAOYSA-N 0.000 claims 1
- FHJLBDHYJZKQIK-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(dimethylcarbamoyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(C(=O)N(C)C)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F FHJLBDHYJZKQIK-UHFFFAOYSA-N 0.000 claims 1
- PMTLECPWSQXEGL-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(dimethylcarbamoyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)N(C)C)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F PMTLECPWSQXEGL-UHFFFAOYSA-N 0.000 claims 1
- YXNRXIUVWDPPKF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(hydroxymethyl)indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(CO)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F YXNRXIUVWDPPKF-UHFFFAOYSA-N 0.000 claims 1
- CNIIJEIFAXYLTF-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(hydroxymethyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(CO)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F CNIIJEIFAXYLTF-UHFFFAOYSA-N 0.000 claims 1
- CJCWFPOLOISDTQ-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(methoxymethyl)indazol-3-yl]benzoic acid Chemical compound C12=CC(COC)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F CJCWFPOLOISDTQ-UHFFFAOYSA-N 0.000 claims 1
- NAEVMDLPGVDNGC-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-(pyrrolidine-1-carbonyl)indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=C(C=C11)C(=O)N2CCCC2)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F NAEVMDLPGVDNGC-UHFFFAOYSA-N 0.000 claims 1
- QERJHEXFPHNEFE-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[2-hydroxyethyl(methyl)carbamoyl]indazol-3-yl]-3-fluorobenzoic acid Chemical compound C12=CC(C(=O)N(CCO)C)=CC=C2C(C=2C(=CC(=CC=2)C(O)=O)F)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F QERJHEXFPHNEFE-UHFFFAOYSA-N 0.000 claims 1
- KAMDYUPZWYIVKD-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]-6-[2-hydroxyethyl(methyl)carbamoyl]indazol-3-yl]benzoic acid Chemical compound C12=CC(C(=O)N(CCO)C)=CC=C2C(C=2C=CC(=CC=2)C(O)=O)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F KAMDYUPZWYIVKD-UHFFFAOYSA-N 0.000 claims 1
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| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| WO2013033461A1 (en) | 2011-08-31 | 2013-03-07 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2013064231A1 (en) | 2011-10-31 | 2013-05-10 | Phenex Pharmaceuticals Ag | SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ, NR1F3) |
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| KR20150007300A (ko) * | 2012-05-08 | 2015-01-20 | 머크 샤프 앤드 돔 코포레이션 | Ror감마 활성의 억제를 위한 테트라히드로나프티리딘 및 관련 비시클릭 화합물 및 질환의 치료 |
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| US9156858B2 (en) | 2012-05-23 | 2015-10-13 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR101742954B1 (ko) | 2012-05-31 | 2017-06-02 | 페넥스 파마슈티컬스 아게 | 고아 핵 수용체 ror[감마]의 조절제로서의 카복사미드 또는 설폰아미드가 치환된 티아졸 및 관련된 유도체 |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| HUE042374T2 (hu) | 2012-06-13 | 2019-06-28 | Incyte Holdings Corp | Szubsztituált triciklusos vegyületek mint FGFR inhibitorok |
| JO3215B1 (ar) | 2012-08-09 | 2018-03-08 | Phenex Pharmaceuticals Ag | حلقات غير متجانسة بها 5 ذرات تحتوي على النيتروجين بها استبدال بكربوكساميد أو سلفوناميد كمعدلات لمستقبل نووي غير محمي RORy |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| 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 |
| WO2014026329A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | N-alkylated indole and indazole compounds as rorgammat inhibitors and uses thereof |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| AU2014204045B2 (en) | 2013-01-04 | 2018-10-18 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| JP6324409B2 (ja) | 2013-01-04 | 2018-05-16 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | ボロン酸誘導体及びその治療的使用 |
| KR102469849B1 (ko) | 2013-04-19 | 2022-11-23 | 인사이트 홀딩스 코포레이션 | Fgfr 저해제로서 이환식 헤테로사이클 |
| EP3027616B1 (en) * | 2013-07-30 | 2018-01-10 | Boehringer Ingelheim International GmbH | Azaindole compounds as modulators of rorc |
| EP3041821B1 (en) * | 2013-09-05 | 2018-05-30 | Boehringer Ingelheim International GmbH | Bicylic compounds as modulators of rorgamma |
| HK1223933A1 (zh) * | 2013-09-11 | 2017-08-11 | F. Hoffmann-La Roche Ag | 作为rorc调节剂的酮-咪唑并呲啶衍生物 |
| AU2014334619A1 (en) * | 2013-10-15 | 2016-04-21 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORyt |
| CN105636952A (zh) * | 2013-10-15 | 2016-06-01 | 詹森药业有限公司 | Rorγt的仲醇喹啉基调节剂 |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| EP3057422B1 (en) | 2013-10-15 | 2019-05-15 | Janssen Pharmaceutica NV | Quinolinyl modulators of ror(gamma)t |
| TW201605797A (zh) * | 2013-12-10 | 2016-02-16 | 葛蘭馬克製藥公司 | 作為ror伽馬調節物的雙環雜芳基化合物 |
| CN104530014B (zh) * | 2013-12-25 | 2018-03-20 | 中国科学院广州生物医药与健康研究院 | 2‑氧代‑1,2‑二氢苯并[cd]吲哚‑6‑磺酰胺类化合物及其组合物和应用 |
| WO2015101928A1 (en) * | 2013-12-31 | 2015-07-09 | Aurigene Discovery Technologies Limited | Fused thiophene and thiazole derivatives as ror gamma modulators |
| RS59007B1 (sr) * | 2014-02-03 | 2019-08-30 | Vitae Pharmaceuticals Llc | Dihidropirolopiridinski inhibitori ror-gama |
| CN106132422A (zh) | 2014-02-27 | 2016-11-16 | 莱斯拉公司 | 使用视黄酸受体相关孤儿受体γ的激动剂的过继细胞疗法＆相关治疗方法 |
| 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 |
| RS59488B1 (sr) | 2014-05-05 | 2019-12-31 | Rempex Pharmaceuticals Inc | Sinteza boronatnih soli i njihove upotrebe |
| WO2015171398A1 (en) | 2014-05-05 | 2015-11-12 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| 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 |
| JP6728061B2 (ja) | 2014-05-05 | 2020-07-22 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγアゴニストとして用いるテトラヒドロキノリンスルホンアミド及び関連化合物ならびに疾患の治療 |
| JP6672176B2 (ja) | 2014-05-19 | 2020-03-25 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | ボロン酸誘導体およびその治療的使用 |
| AU2015284307A1 (en) | 2014-07-01 | 2017-02-02 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EA031967B1 (ru) | 2014-10-14 | 2019-03-29 | Вайтаи Фармасьютиклз, Инк. | ДИГИДРОПИРРОЛОПИРИДИНОВЫЕ ИНГИБИТОРЫ ROR-γ |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| 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 |
| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| JP6854776B2 (ja) * | 2015-01-08 | 2021-04-07 | インぺティス バイオサイエンス リミテッド | 二環式化合物、その組成物および医薬用途 |
| AU2016219183B2 (en) * | 2015-02-11 | 2020-06-11 | 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 |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| AU2016219822B2 (en) | 2015-02-20 | 2020-07-09 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| 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 |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10849992B1 (en) * | 2015-04-07 | 2020-12-01 | Alector Llc | Methods of screening for sortilin binding antagonists |
| EP3292119A4 (en) | 2015-05-05 | 2018-10-03 | Lycera Corporation | DIHYDRO-2H-BENZO[b][1,4]OXAZINE SULFONAMIDE AND RELATED COMPOUNDS FOR USE AS AGONISTS OF RORy AND THE TREATMENT OF DISEASE |
| US10106501B2 (en) * | 2015-06-09 | 2018-10-23 | Abbvie Inc. | Nuclear receptor modulators |
| WO2016198908A1 (en) * | 2015-06-09 | 2016-12-15 | Abbvie Inc. | Ror nuclear receptor modulators |
| EP3307738B1 (en) | 2015-06-11 | 2022-04-20 | The Regents of the University of Michigan | Aryl dihydro-2h-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of rory and the treatment of disease |
| WO2017024018A1 (en) | 2015-08-05 | 2017-02-09 | Vitae Pharmaceuticals, Inc. | Modulators of ror-gamma |
| CA3129180A1 (en) * | 2015-09-21 | 2017-03-30 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| AU2016344115A1 (en) | 2015-10-27 | 2018-05-10 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as rorgammat inhibitors 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 |
| WO2017075178A1 (en) * | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | SUBSTITUTED BICYCLIC PYRAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| KR20180086221A (ko) | 2015-11-20 | 2018-07-30 | 비타이 파마슈티컬즈, 인코포레이티드 | Ror-감마의 조절물질 |
| CN105412929B (zh) * | 2015-11-27 | 2018-03-20 | 肖定璋 | Il7r‑3’utr在调控维甲酸相关孤儿核受体表达中的应用 |
| CN109071516B (zh) | 2015-12-15 | 2021-08-31 | 阿斯利康(瑞典)有限公司 | 新颖的化合物 |
| US10793566B2 (en) | 2016-01-21 | 2020-10-06 | Zibo Biopolar Changsheng Pharmaceutical Co. Ltd. | Bruton's tyrosine kinase inhibitors |
| IL260691B (en) * | 2016-01-21 | 2022-07-01 | Zibo Biopolar Changsheng Pharmaceutical Co Ltd | Bruton's tyrosine kinase inhibitors |
| TW202220968A (zh) | 2016-01-29 | 2022-06-01 | 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 |
| JP7060245B2 (ja) | 2016-06-30 | 2022-04-26 | キューペックス バイオファーマ， インコーポレイテッド | ボロン酸誘導体およびその治療的使用 |
| JP6732177B2 (ja) * | 2016-11-01 | 2020-07-29 | 学校法人東京理科大学 | 安息香酸誘導体及び脱水縮合剤、並びにエステル及びラクトンの製造方法 |
| JP2020111510A (ja) * | 2017-03-29 | 2020-07-27 | 科研製薬株式会社 | インダゾール誘導体及びそれを含有する医薬 |
| JP7090639B2 (ja) | 2017-04-11 | 2022-06-24 | サンシャイン・レイク・ファーマ・カンパニー・リミテッド | フッ素置換されたインダゾール化合物及びその使用 |
| IT201700041723A1 (it) | 2017-04-14 | 2018-10-14 | Italfarmaco Spa | Nuovi inibitori selettivi di HDAC6 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| PH12019502736A1 (en) * | 2017-06-12 | 2020-10-26 | Cypress Bio Tech Company Ltd | Multi-application insect repellent additive |
| WO2018229155A1 (en) | 2017-06-14 | 2018-12-20 | Astrazeneca Ab | 2,3-dihydroisoindole-1-carboxamides useful as ror-gamma modulators |
| MA49685A (fr) | 2017-07-24 | 2021-04-14 | Vitae Pharmaceuticals Llc | INHIBITEURS DE ROR gamma |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| CN109485595B (zh) * | 2017-09-12 | 2022-05-27 | 江苏恒瑞医药股份有限公司 | 亲水性基团取代的吲哚甲酰胺类衍生物、其制备方法及其在医药上的应用 |
| CA3078627A1 (en) | 2017-10-11 | 2019-04-18 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis thereof |
| AR117398A1 (es) | 2018-03-12 | 2021-08-04 | Abbvie Inc | Inhibidores de la señalización mediada por tirosina cinasa 2 |
| EP3781576B1 (en) | 2018-04-20 | 2024-06-12 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3788046B1 (en) | 2018-05-04 | 2025-12-10 | Incyte Corporation | Salts of an fgfr inhibitor |
| EP4309737A3 (en) | 2018-05-04 | 2024-03-27 | Incyte Corporation | Solid forms of an fgfr inhibitor and processes for preparing the same |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021076602A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての三環式複素環 |
| KR20220131900A (ko) | 2019-12-04 | 2022-09-29 | 인사이트 코포레이션 | Fgfr 억제제의 유도체 |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CA3215903A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2023232870A1 (en) | 2022-05-31 | 2023-12-07 | Immunic Ag | Rorg/rorgt modulators for the treatment of virus infections like covid-19 |
Family Cites Families (43)
| 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 |
| US4751235A (en) * | 1986-12-23 | 1988-06-14 | Sandoz Pharm. Corp. | Anti-atherosclerotic indolizine derivatives |
| 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 |
| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase 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 |
| UA87494C2 (en) * | 2004-03-30 | 2009-07-27 | Вертекс Фармасьютикалс Инкорпорейтед | Azaindoles useful as inhibitors of jak and other protein kinases |
| CA2560454C (en) * | 2004-03-30 | 2013-05-21 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| US7417063B2 (en) * | 2004-04-13 | 2008-08-26 | Bristol-Myers Squibb Company | Bicyclic heterocycles useful as serine protease inhibitors |
| BRPI0514017A (pt) | 2004-08-03 | 2008-05-27 | Wyeth Corp | indazóis úteis no tratamento de doenças cardiovasculares |
| US7605168B2 (en) * | 2004-09-03 | 2009-10-20 | Plexxikon, Inc. | 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 |
| EP1828180A4 (en) * | 2004-12-08 | 2010-09-15 | Glaxosmithkline Llc | 1H-pyrrolo [2,3-BETA] PYRIDINE |
| AU2007217040A1 (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 |
| MX2008011220A (es) | 2006-03-07 | 2008-09-11 | Array Biopharma Inc | Compuestos de pirazol heterobiciclicos y metodos de uso. |
| CN101490001A (zh) * | 2006-06-09 | 2009-07-22 | Icos股份有限公司 | 用作dp-2拮抗剂的取代的苯乙酸 |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| DK2134685T3 (en) | 2007-04-16 | 2015-12-07 | Abbvie Inc | 7-unsubstituted indole derivatives as MCL-1 inhibitors |
| 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 |
| MY148609A (en) | 2007-06-05 | 2013-05-15 | Merck Sharp & Dohme | Polycyclic indazole derivatives and their use as erk inhibitors for the treatment of cancer |
| CA2694224A1 (en) * | 2007-07-25 | 2009-01-29 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| FR2933609B1 (fr) * | 2008-07-10 | 2010-08-27 | Fournier Lab Sa | Utilisation de derives d'indole comme activateurs de nurr-1, pour le traitement de la maladie de parkinson. |
| EP2181710A1 (en) | 2008-10-28 | 2010-05-05 | Phenex Pharmaceuticals AG | Ligands for modulation of orphan receptor-gamma (NR1F3) activity |
| US8877772B2 (en) * | 2008-11-25 | 2014-11-04 | University Of Rochester | Substituted pyrrolo[2,3-B]pyridines as MLK inhibitors |
| 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 |
| EP2513096A1 (en) | 2009-12-18 | 2012-10-24 | Janssen Pharmaceutica, N.V. | Substituted aminothiazolone indazoles as estrogen related receptor-a modulators |
| WO2011103189A1 (en) | 2010-02-16 | 2011-08-25 | Uwm Research Foundation, Inc. | Methods of reducing virulence in bacteria |
| EP2571361A4 (en) | 2010-05-19 | 2013-11-13 | Univ North Carolina | PYRAZOLOPYRIMIDINE COMPOUNDS FOR CANCER TREATMENT |
| CA2816753A1 (en) | 2010-11-08 | 2012-05-18 | Lycera Corporation | N- sulfonylated tetrahydroquinolines and related bicyclic compounds inhibition of rory activity and the treatment of diseases |
| 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 |
| CN108586500B (zh) * | 2010-12-22 | 2021-06-25 | 慕尼黑路德维希马克西米利安斯大学 | 锌配位络合物及制备有机锌试剂的方法 |
| 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 |
| 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 |
-
2011
- 2011-02-11 EP EP11154188A patent/EP2487159A1/en not_active Withdrawn
-
2012
- 2012-02-10 KR KR1020137023663A patent/KR20140044791A/ko not_active Withdrawn
- 2012-02-10 MX MX2013009149A patent/MX2013009149A/es unknown
- 2012-02-10 BR BR112013020352A patent/BR112013020352A2/pt not_active IP Right Cessation
- 2012-02-10 CA CA2828059A patent/CA2828059A1/en not_active Abandoned
- 2012-02-10 CN CN201280018025.3A patent/CN103748076A/zh active Pending
- 2012-02-10 AU AU2012214029A patent/AU2012214029A1/en not_active Abandoned
- 2012-02-10 WO PCT/CN2012/071017 patent/WO2012106995A1/en not_active Ceased
- 2012-02-10 US US13/983,818 patent/US9095583B2/en active Active
- 2012-02-10 JP JP2013552823A patent/JP5934721B2/ja not_active Expired - Fee Related
- 2012-02-10 RU RU2013141528/04A patent/RU2013141528A/ru not_active Application Discontinuation
- 2012-02-10 EP EP12744370.3A patent/EP2683693B1/en active Active
-
2015
- 2015-06-26 US US14/752,195 patent/US9603838B2/en active Active
-
2017
- 2017-03-20 US US15/463,371 patent/US9884043B2/en active Active
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