JP2018535958A5 - - Google Patents
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- JP2018535958A5 JP2018535958A5 JP2018521300A JP2018521300A JP2018535958A5 JP 2018535958 A5 JP2018535958 A5 JP 2018535958A5 JP 2018521300 A JP2018521300 A JP 2018521300A JP 2018521300 A JP2018521300 A JP 2018521300A JP 2018535958 A5 JP2018535958 A5 JP 2018535958A5
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- JP
- Japan
- Prior art keywords
- tetrahydro
- chloro
- ene
- carboxylic acid
- indazol
- 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.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims 70
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 claims 43
- -1 2-chloro-6-cyclopropylbenzoyl Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000002619 bicyclic group Chemical group 0.000 claims 7
- 208000023275 Autoimmune disease Diseases 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- XEDBDFGQMFSCQN-LYNLNPNLSA-N (1R,2S)-4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-2-methylcyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=C[C@H](C)[C@@H](CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F XEDBDFGQMFSCQN-LYNLNPNLSA-N 0.000 claims 2
- NEGMILSFVWIQIL-LYNLNPNLSA-N (1R,6S)-4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-6-methylcyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CC[C@H]([C@@H](C)C1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F NEGMILSFVWIQIL-LYNLNPNLSA-N 0.000 claims 2
- HTFFYUKPBRMHDC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC2(COC2)C1 HTFFYUKPBRMHDC-UHFFFAOYSA-N 0.000 claims 2
- LBPQGIGHZHRPLL-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-methylsulfonylazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CS(=O)(=O)C1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 LBPQGIGHZHRPLL-UHFFFAOYSA-N 0.000 claims 2
- DCZCULPTHDAODX-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(4-methyl-3-oxopiperazine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN1CCN(CC1=O)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 DCZCULPTHDAODX-UHFFFAOYSA-N 0.000 claims 2
- UYKNWUYMCKKENK-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(difluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-1-methylcyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(C)(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)F UYKNWUYMCKKENK-UHFFFAOYSA-N 0.000 claims 2
- AKPTWDVOBMAVGI-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(difluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)F AKPTWDVOBMAVGI-UHFFFAOYSA-N 0.000 claims 2
- YTKAXVXPINAMOA-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(1-methyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound Cn1ncc2CN(Cc12)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F YTKAXVXPINAMOA-UHFFFAOYSA-N 0.000 claims 2
- GWFUTAVBSXQUPQ-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(2-oxa-7-azaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CCC2(COC2)C1 GWFUTAVBSXQUPQ-UHFFFAOYSA-N 0.000 claims 2
- ADNUHMCTSHLOCW-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxy-3-methylazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1(C)CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F ADNUHMCTSHLOCW-UHFFFAOYSA-N 0.000 claims 2
- XDRNCXANOQPKQZ-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-1-methylcyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(C)(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F XDRNCXANOQPKQZ-UHFFFAOYSA-N 0.000 claims 2
- BGAAVEXGSUFCRP-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F BGAAVEXGSUFCRP-UHFFFAOYSA-N 0.000 claims 2
- IIOLRBSOSSKOMW-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-1-methylcyclohex-3-ene-1-carboxylic acid Chemical compound CC1(CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CC2(C1)CCCO2)C(O)=O IIOLRBSOSSKOMW-UHFFFAOYSA-N 0.000 claims 2
- RQOBBLVHVSGJFR-KWSLZPIXSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(3S,4R)-3-(dimethylamino)-4-fluoropyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)[C@H]1CN(C[C@H]1F)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F RQOBBLVHVSGJFR-KWSLZPIXSA-N 0.000 claims 2
- OYKSKFGHZKUKAZ-HFDKMXLISA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(3S,4R)-3-fluoro-4-hydroxypyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound O[C@@H]1CN(C[C@@H]1F)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F OYKSKFGHZKUKAZ-HFDKMXLISA-N 0.000 claims 2
- NKAXDVAAVROLHJ-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[methyl-[(1-methylpyrazol-4-yl)methyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(Cc1cnn(C)c1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F NKAXDVAAVROLHJ-UHFFFAOYSA-N 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- WBKXHIRGJZEWDZ-APROBQCTSA-N (1R,2S)-4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-hydroxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-2-methylcyclohex-3-ene-1-carboxylic acid Chemical compound C[C@H]1C=C(CC[C@H]1C(O)=O)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CC(O)C1 WBKXHIRGJZEWDZ-APROBQCTSA-N 0.000 claims 1
- ZOXHAJWMESADHM-PRZWFREHSA-N (1R,6S)-4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(4-hydroxypiperidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]-6-methylcyclohex-3-ene-1-carboxylic acid Chemical compound C[C@H]1CC(=CC[C@H]1C(O)=O)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CCC(O)CC1 ZOXHAJWMESADHM-PRZWFREHSA-N 0.000 claims 1
- YRFZSMSVLYGUDY-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropyl-3-fluorobenzoyl)-6-(1,7-diazaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)c(F)ccc2C2CC2)c2CC(CCc12)C(=O)N1CCC2(CCN2)C1 YRFZSMSVLYGUDY-UHFFFAOYSA-N 0.000 claims 1
- ZOMBBXNRGYZKFV-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropyl-3-fluorobenzoyl)-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)c(F)ccc1C1CC1 ZOMBBXNRGYZKFV-UHFFFAOYSA-N 0.000 claims 1
- YKQSSNAIFXXQSS-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropyl-3-fluorobenzoyl)-6-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)c(F)ccc2C2CC2)c2CC(CCc12)C(=O)N1CC2(C1)CCCO2 YKQSSNAIFXXQSS-UHFFFAOYSA-N 0.000 claims 1
- YWIKGOJTNIUWMW-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(1-methyl-1,7-diazaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN1CCC11CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 YWIKGOJTNIUWMW-UHFFFAOYSA-N 0.000 claims 1
- AEANOZLRFWRFJX-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(1-methylpyrrolidin-3-yl)oxycarbonyl-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN1CCC(C1)OC(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 AEANOZLRFWRFJX-UHFFFAOYSA-N 0.000 claims 1
- COESGVXAWXMFNG-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(1-oxa-6-azaspiro[3.3]heptane-6-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC2(CCO2)C1 COESGVXAWXMFNG-UHFFFAOYSA-N 0.000 claims 1
- NOHWGUMUBUJCIW-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(1-oxa-7-azaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC2(CCO2)C1 NOHWGUMUBUJCIW-UHFFFAOYSA-N 0.000 claims 1
- DZECVAUWGFTPTI-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(1-oxa-7-azaspiro[4.4]nonane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC2(CCCO2)C1 DZECVAUWGFTPTI-UHFFFAOYSA-N 0.000 claims 1
- NTXNQMOBDDGHSO-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(2-oxa-7-azaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC2(COC2)C1 NTXNQMOBDDGHSO-UHFFFAOYSA-N 0.000 claims 1
- SQDISUWXOFVEPV-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(2-oxa-7-azaspiro[4.4]nonane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC2(CCOC2)C1 SQDISUWXOFVEPV-UHFFFAOYSA-N 0.000 claims 1
- YSYQTQJMYUHWKK-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3,3-difluoroazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC(F)(F)C1 YSYQTQJMYUHWKK-UHFFFAOYSA-N 0.000 claims 1
- LNQPXTJNQMQDFJ-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-cyano-3-fluoroazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)C1=NN(C(=O)C2=C(Cl)C=CC=C2C2CC2)C2=C1CCC(C2)C(=O)N1CC(F)(C1)C#N LNQPXTJNQMQDFJ-UHFFFAOYSA-N 0.000 claims 1
- FPHHVJUFTMJARF-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-cyclopropyl-3-hydroxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC(O)(C1)C1CC1 FPHHVJUFTMJARF-UHFFFAOYSA-N 0.000 claims 1
- GAJPPMGWYOSXBT-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-hydroxy-3-methylazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC1(O)CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 GAJPPMGWYOSXBT-UHFFFAOYSA-N 0.000 claims 1
- OTZKPNBNVXZALL-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-hydroxy-3-methylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC1(O)CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 OTZKPNBNVXZALL-UHFFFAOYSA-N 0.000 claims 1
- DATIPDUTPZTLOU-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-methoxy-3-methylazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1(C)CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 DATIPDUTPZTLOU-UHFFFAOYSA-N 0.000 claims 1
- AMWNOECANKTNAH-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(3-methoxyazetidine-1-carbonyl)-6-methyl-5,7-dihydro-4H-indazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1(C)CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 AMWNOECANKTNAH-UHFFFAOYSA-N 0.000 claims 1
- ALYCAHOQFJQXFI-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(5-methyl-2,5-diazaspiro[3.4]octane-2-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN1CCCC11CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 ALYCAHOQFJQXFI-UHFFFAOYSA-N 0.000 claims 1
- CDLCHIKGANLBRG-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(5-methyl-2-oxa-5,8-diazaspiro[3.5]nonane-8-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN1CCN(CC11COC1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 CDLCHIKGANLBRG-UHFFFAOYSA-N 0.000 claims 1
- BSMGEHANJQZXGD-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC2(C1)CCCO2 BSMGEHANJQZXGD-UHFFFAOYSA-N 0.000 claims 1
- RZARJTGVPHPBQC-XVAXZDLZSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2R)-2-(fluoromethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC[C@@H]1CF RZARJTGVPHPBQC-XVAXZDLZSA-N 0.000 claims 1
- MVENYUHQISXSEN-XVAXZDLZSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2R)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC[C@H]1CCCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 MVENYUHQISXSEN-XVAXZDLZSA-N 0.000 claims 1
- RIVNLCKIUDDANY-LZBANZJXSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2R)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC[C@H]1CCCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 RIVNLCKIUDDANY-LZBANZJXSA-N 0.000 claims 1
- RZARJTGVPHPBQC-CBNMVNINSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2S)-2-(fluoromethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC[C@H]1CF RZARJTGVPHPBQC-CBNMVNINSA-N 0.000 claims 1
- YLPOIHDFYZLHCA-MHJFOBGBSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2S)-2-(hydroxymethyl)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC[C@@H]1CCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 YLPOIHDFYZLHCA-MHJFOBGBSA-N 0.000 claims 1
- RIVNLCKIUDDANY-HRTMPFAESA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC[C@@H]1CCCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 RIVNLCKIUDDANY-HRTMPFAESA-N 0.000 claims 1
- VDZKIMVTHBJUMU-LZBANZJXSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(3R)-3-(dimethylamino)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)[C@@H]1CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 VDZKIMVTHBJUMU-LZBANZJXSA-N 0.000 claims 1
- MQYZIKACRNPPMY-XVAXZDLZSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(3R)-3-methoxypyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CO[C@@H]1CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 MQYZIKACRNPPMY-XVAXZDLZSA-N 0.000 claims 1
- MQYZIKACRNPPMY-CBNMVNINSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[(3S)-3-methoxypyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CO[C@H]1CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 MQYZIKACRNPPMY-CBNMVNINSA-N 0.000 claims 1
- XCRHLXDDLNLMFD-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[2-(1-methyl-1,2,4-triazol-3-yl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound Cn1cnc(n1)C1CCCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 XCRHLXDDLNLMFD-UHFFFAOYSA-N 0.000 claims 1
- UKZWNFRMWCEDJP-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[2-(methylaminomethyl)pyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CNCC1CCCN1C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 UKZWNFRMWCEDJP-UHFFFAOYSA-N 0.000 claims 1
- UGUHXAGSKUUZHG-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[2-[(2-methylpropan-2-yl)oxycarbonyl]-2,6-diazaspiro[3.3]heptane-6-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC2(C1)CN(C2)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 UGUHXAGSKUUZHG-UHFFFAOYSA-N 0.000 claims 1
- SMHMXDVMEYAVDP-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[3-(1,2,4-triazol-4-yl)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC(C1)n1cnnc1 SMHMXDVMEYAVDP-UHFFFAOYSA-N 0.000 claims 1
- CZHXQDUVLKFFDU-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[3-(1H-1,2,4-triazol-5-yl)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC(C1)c1ncn[nH]1 CZHXQDUVLKFFDU-UHFFFAOYSA-N 0.000 claims 1
- QQFVVYMVOCJCNC-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[3-(2-hydroxypropan-2-yl)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC(C)(O)C1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 QQFVVYMVOCJCNC-UHFFFAOYSA-N 0.000 claims 1
- WYDVNNCUQVFKMT-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[3-(difluoromethyl)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC(C1)C(F)F WYDVNNCUQVFKMT-UHFFFAOYSA-N 0.000 claims 1
- KGOQWERFZLKROR-UHFFFAOYSA-N 4-[1-(2-chloro-6-cyclopropylbenzoyl)-6-[3-(dimethylamino)azetidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)C1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1CC1 KGOQWERFZLKROR-UHFFFAOYSA-N 0.000 claims 1
- BFBGFSFNWOIKPW-UHFFFAOYSA-N 4-[1-[2-(azetidin-1-yl)-4-methylpyridine-3-carbonyl]-6-(3-methoxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound COC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(C)ccnc1N1CCC1 BFBGFSFNWOIKPW-UHFFFAOYSA-N 0.000 claims 1
- AUBZMWYDZUBCIS-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(difluoromethyl)cyclopropyl]benzoyl]-6-(2-oxa-7-azaspiro[3.4]octane-7-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)F)c2CC(CCc12)C(=O)N1CCC2(COC2)C1 AUBZMWYDZUBCIS-UHFFFAOYSA-N 0.000 claims 1
- FPTFEAHQVOCWCL-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-hydroxy-3-methylazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC1(O)CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F FPTFEAHQVOCWCL-UHFFFAOYSA-N 0.000 claims 1
- CRYLFLVBSYOMBH-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-hydroxy-3-methylpyrrolidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CC1(O)CCN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F CRYLFLVBSYOMBH-UHFFFAOYSA-N 0.000 claims 1
- ABKDPJYLDMZBHF-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(3-hydroxyazetidine-1-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC1CN(C1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F ABKDPJYLDMZBHF-UHFFFAOYSA-N 0.000 claims 1
- VOBYZTULZPKRRY-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CC2(C1)CCCO2 VOBYZTULZPKRRY-UHFFFAOYSA-N 0.000 claims 1
- SXDVMHFULCPURC-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-(pyridin-2-ylcarbamoyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)Nc1ccccn1 SXDVMHFULCPURC-UHFFFAOYSA-N 0.000 claims 1
- LJCUCPFZAWKLCD-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(2,2-difluorocyclopropyl)carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)NC1CC1(F)F LJCUCPFZAWKLCD-UHFFFAOYSA-N 0.000 claims 1
- ZSAPETMKHVKRQT-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(2-fluorophenyl)carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)Nc1ccccc1F ZSAPETMKHVKRQT-UHFFFAOYSA-N 0.000 claims 1
- GCHHPSPUFDRDCR-KKXNLOMOSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(3R)-3-cyanopyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N1CC[C@H](C1)C#N GCHHPSPUFDRDCR-KKXNLOMOSA-N 0.000 claims 1
- RQOBBLVHVSGJFR-INLZHIODSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(3S,4S)-3-(dimethylamino)-4-fluoropyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)[C@H]1CN(C[C@@H]1F)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F RQOBBLVHVSGJFR-INLZHIODSA-N 0.000 claims 1
- QJRKKQVHKLZGHQ-OSZFHHHMSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[(3S,4S)-3-hydroxy-4-methoxypyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CO[C@H]1CN(C[C@@H]1O)C(=O)C1CCC2=C(C1)N(N=C2C1=CCC(CC1)C(O)=O)C(=O)C1=C(Cl)C=CC=C1C1(CC1)C(F)(F)F QJRKKQVHKLZGHQ-OSZFHHHMSA-N 0.000 claims 1
- VGRKXRAVPXHMQP-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[4-(dimethylamino)-3,3-difluoropyrrolidine-1-carbonyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)C1CN(CC1(F)F)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F VGRKXRAVPXHMQP-UHFFFAOYSA-N 0.000 claims 1
- LJEMUNHMIUFTGZ-OHDIRIAZSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(1R,2R)-2-hydroxycyclopentyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound O[C@@H]1CCC[C@H]1NC(=O)C1CCC2=C(C1)N(N=C2C1=CCC(CC1)C(O)=O)C(=O)C1=C(Cl)C=CC=C1C1(CC1)C(F)(F)F LJEMUNHMIUFTGZ-OHDIRIAZSA-N 0.000 claims 1
- LJEMUNHMIUFTGZ-MCPMUOGYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(1R,2S)-2-hydroxycyclopentyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound O[C@H]1CCC[C@H]1NC(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F LJEMUNHMIUFTGZ-MCPMUOGYSA-N 0.000 claims 1
- BPXPGLVAXIURDY-QKRATHMNSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(1S,2R)-2-fluorocyclopentyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)N[C@H]1CCC[C@H]1F BPXPGLVAXIURDY-QKRATHMNSA-N 0.000 claims 1
- LJEMUNHMIUFTGZ-BYSKWZFGSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(1S,2R)-2-hydroxycyclopentyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound O[C@@H]1CCC[C@@H]1NC(=O)C1CCC2=C(C1)N(N=C2C1=CCC(CC1)C(O)=O)C(=O)C1=C(Cl)C=CC=C1C1(CC1)C(F)(F)F LJEMUNHMIUFTGZ-BYSKWZFGSA-N 0.000 claims 1
- YLUOHJPXIPEXKD-RIBBAFADSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(3R,4R)-4-fluorooxolan-3-yl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)C1=NN(C(=O)C2=C(Cl)C=CC=C2C2(CC2)C(F)(F)F)C2=C1CCC(C2)C(=O)N[C@@H]1COC[C@@H]1F YLUOHJPXIPEXKD-RIBBAFADSA-N 0.000 claims 1
- YMVYDMHWGYRRAB-RIBBAFADSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(3R,4S)-4-fluoropyrrolidin-3-yl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)C1=NN(C(=O)C2=C(Cl)C=CC=C2C2(CC2)C(F)(F)F)C2=C1CCC(C2)C(=O)N[C@@H]1CNC[C@@H]1F YMVYDMHWGYRRAB-RIBBAFADSA-N 0.000 claims 1
- YLUOHJPXIPEXKD-HCKZNZMISA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(3S,4R)-4-fluorooxolan-3-yl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)C1=NN(C(=O)C2=C(Cl)C=CC=C2C2(CC2)C(F)(F)F)C2=C1CCC(C2)C(=O)N[C@H]1COC[C@@H]1F YLUOHJPXIPEXKD-HCKZNZMISA-N 0.000 claims 1
- YMVYDMHWGYRRAB-HCKZNZMISA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[(3S,4S)-4-fluoropyrrolidin-3-yl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)C1=NN(C(=O)C2=C(Cl)C=CC=C2C2(CC2)C(F)(F)F)C2=C1CCC(C2)C(=O)N[C@H]1CNC[C@@H]1F YMVYDMHWGYRRAB-HCKZNZMISA-N 0.000 claims 1
- VRTVQOCMEMDZPB-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[1-(2,2,2-trifluoroethyl)pyrazol-3-yl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2(CC2)C(F)(F)F)c2CC(CCc12)C(=O)Nc1ccn(CC(F)(F)F)n1 VRTVQOCMEMDZPB-UHFFFAOYSA-N 0.000 claims 1
- UDBLXJOTBXIIJR-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[[3-(dimethylamino)-2,2-difluoropropyl]carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C)CC(F)(F)CNC(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F UDBLXJOTBXIIJR-UHFFFAOYSA-N 0.000 claims 1
- PWFZXPGMGZUFSZ-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[methyl(pyrazin-2-ylmethyl)carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(Cc1cnccn1)C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F PWFZXPGMGZUFSZ-UHFFFAOYSA-N 0.000 claims 1
- LOWWDWFDVLDGSI-UHFFFAOYSA-N 4-[1-[2-chloro-6-[1-(trifluoromethyl)cyclopropyl]benzoyl]-6-[methyl(pyridin-2-yl)carbamoyl]-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound CN(C(=O)C1CCc2c(C1)n(nc2C1=CCC(CC1)C(O)=O)C(=O)c1c(Cl)cccc1C1(CC1)C(F)(F)F)c1ccccn1 LOWWDWFDVLDGSI-UHFFFAOYSA-N 0.000 claims 1
- CXVRKQACCUYWFM-UHFFFAOYSA-N 4-[6-(1,3,3a,4,6,6a-hexahydrofuro[3,4-c]pyrrole-5-carbonyl)-1-(2-chloro-6-cyclopropylbenzoyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CC2COCC2C1 CXVRKQACCUYWFM-UHFFFAOYSA-N 0.000 claims 1
- PYVIDPJYTUEDEX-UHFFFAOYSA-N 4-[6-(azetidine-1-carbonyl)-1-(2-chloro-6-cyclopropylbenzoyl)-4,5,6,7-tetrahydroindazol-3-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC(=CC1)c1nn(C(=O)c2c(Cl)cccc2C2CC2)c2CC(CCc12)C(=O)N1CCC1 PYVIDPJYTUEDEX-UHFFFAOYSA-N 0.000 claims 1
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- 239000002253 acid Substances 0.000 claims 1
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- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 1
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| JP2018531958A (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阻害薬としてのヘテロアリール置換安息香酸及びその使用 |
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| CA3094988A1 (en) | 2018-03-30 | 2019-10-03 | Biotheryx, Inc. | Thienopyrimidinone compounds |
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Family Cites Families (127)
| 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 |
| GB8607294D0 (en) | 1985-04-17 | 1986-04-30 | Ici America Inc | Heterocyclic amide derivatives |
| 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 |
| TW263508B (enExample) | 1991-02-12 | 1995-11-21 | Pfizer | |
| JP3414433B2 (ja) | 1993-03-01 | 2003-06-09 | 日本化薬株式会社 | 電子写真用トナー |
| US5639780A (en) | 1995-05-22 | 1997-06-17 | Merck Frosst Canada, Inc. | N-benzyl indol-3-yl butanoic acid derivatives as cyclooxygenase inhibitors |
| DE19523446A1 (de) | 1995-06-28 | 1997-01-02 | Bayer Ag | Benzotriazole |
| AU6490396A (en) | 1995-07-14 | 1997-02-18 | Smithkline Beecham Corporation | Substituted-pent-4-ynoic acids |
| BR9609888A (pt) | 1995-08-10 | 1999-05-25 | Bayer Ag | Halogenobenzimidazóis |
| HUP9900625A3 (en) | 1995-12-28 | 2003-04-28 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives, pharmaceutical compositions containing them and process for preparing the compounds |
| WO1997048697A1 (en) | 1996-06-19 | 1997-12-24 | Rhone-Poulenc Rorer Limited | Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase |
| ES2215242T3 (es) | 1996-11-19 | 2004-10-01 | Amgen Inc. | Agentes antiinflamatorios de pirrol condensado sustituido con arilo y heteroarilo. |
| US6828344B1 (en) | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6133290A (en) | 1998-07-31 | 2000-10-17 | Eli Lilly And Company | 5-HT1F agonists |
| JP2002527359A (ja) | 1998-09-18 | 2002-08-27 | ビーエーエスエフ アクチェンゲゼルシャフト | キナーゼインヒビターとしての４−アミノピロリピリミジン |
| US6348032B1 (en) | 1998-11-23 | 2002-02-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with benzimidazole derivatives |
| AU6762400A (en) | 1999-08-12 | 2001-03-13 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| WO2001021577A2 (en) | 1999-09-20 | 2001-03-29 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| 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 |
| TWI239942B (en) | 2001-06-11 | 2005-09-21 | Dainippon Pharmaceutical Co | N-arylphenylacetamide derivative and pharmaceutical composition containing the same |
| ATE515495T1 (de) | 2001-08-03 | 2011-07-15 | Schering Corp | Gamma sekretase inhibitoren |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| DE10229777A1 (de) | 2002-07-03 | 2004-01-29 | Bayer Ag | Indolin-Phenylsulfonamid-Derivate |
| FR2845382A1 (fr) | 2002-10-02 | 2004-04-09 | Sanofi Synthelabo | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| UA80171C2 (en) | 2002-12-19 | 2007-08-27 | Pfizer Prod Inc | Pyrrolopyrimidine derivatives |
| JP4601038B2 (ja) | 2003-03-26 | 2010-12-22 | 第一三共株式会社 | インドリルマレイミド類 |
| EP2145888A1 (en) | 2003-09-18 | 2010-01-20 | Conforma Therapeutics Corporation | Deazapurine derivatives as HSP90-Inhibitors |
| SE0302760D0 (sv) | 2003-10-20 | 2003-10-20 | Biovitrum Ab | New compounds |
| US7420059B2 (en) | 2003-11-20 | 2008-09-02 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
| KR20110098980A (ko) | 2003-12-22 | 2011-09-02 | 아지노모토 가부시키가이샤 | 신규한 페닐알라닌 유도체 |
| DE602004025504D1 (de) | 2003-12-23 | 2010-03-25 | Novartis Ag | Bicyclische heterocyclische p-38-kinase-inhibitoren |
| CA2572334A1 (en) | 2004-07-01 | 2006-01-19 | New York University | Compositions and methods for modulation of ror.gamma.t |
| US7592363B2 (en) | 2004-08-03 | 2009-09-22 | Wyeth | Indazoles |
| US20070010537A1 (en) | 2004-08-20 | 2007-01-11 | Kazumasa Hamamura | Fused pyramidine derivative and use thereof |
| EP1786813A2 (en) | 2004-09-03 | 2007-05-23 | 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 |
| AR051780A1 (es) | 2004-11-29 | 2007-02-07 | Japan Tobacco Inc | Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos |
| US20090233955A1 (en) | 2004-12-08 | 2009-09-17 | Frazee James S | 1H-Pyrrolo[2,3-B]Pyridnes |
| ATE517883T1 (de) | 2005-08-25 | 2011-08-15 | Schering Corp | Imidazolderivate als funktionelle selektive agonisten des alpha2c-adrenorezeptors |
| US8003624B2 (en) | 2005-08-25 | 2011-08-23 | Schering Corporation | Functionally selective ALPHA2C adrenoreceptor agonists |
| ATE543813T1 (de) | 2005-09-01 | 2012-02-15 | Janssen Pharmaceutica Nv | Neue benzopyranderivate als kaliumkanalöffner |
| WO2007031429A1 (en) | 2005-09-15 | 2007-03-22 | F. Hoffmann-La Roche Ag | Novel heterobicyclic derivatives useful as inhibitors of liver carnitine palmitoyl transferase |
| EP1996563B1 (en) | 2006-02-13 | 2012-03-21 | F. Hoffmann-La Roche AG | Heterobicyclic sulfonamide derivatives for the treatment of diabetes |
| AU2007217040A1 (en) | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-HT6 receptor affinity |
| KR101411695B1 (ko) | 2006-02-17 | 2014-07-03 | 리겔 파마슈티칼스, 인크. | 자가면역 질환의 치료 또는 예방을 위한 2,4-피리미딘디아민 화합물 |
| 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 |
| CA2645137A1 (en) | 2006-03-07 | 2007-09-13 | James F. Blake | Heterobicyclic pyrazole compounds and methods of use |
| CA2651072A1 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| US20080305169A1 (en) | 2006-05-26 | 2008-12-11 | Japan Tobacco Inc. | Pharmaceutical Compositions Comprising Nitrogen-Containing Fused Ring Coumpounds |
| JP2009538910A (ja) | 2006-06-01 | 2009-11-12 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしての１−スルホニルインダゾリルアミン誘導体および１−スルホニルインダゾリルアミド誘導体 |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| EP2046741B1 (en) | 2006-07-03 | 2012-10-31 | Proximagen Ltd. | Indoles as 5-ht6 modulators |
| TWI315304B (en) | 2006-08-31 | 2009-10-01 | Univ Taipei Medical | Indoline-sulfonamides compounds |
| WO2008045664A2 (en) | 2006-10-06 | 2008-04-17 | Kalypsys, Inc. | Heterocyclic pde4 inhibitors as antiinflammatory agents |
| WO2008062740A1 (fr) | 2006-11-20 | 2008-05-29 | Japan Tobacco Inc. | Composé azoté à anneaux fusionnés et son utilisation |
| US7799933B2 (en) | 2006-12-21 | 2010-09-21 | Hoffman-La Roche Inc. | Sulfonamide derivatives |
| US20080186971A1 (en) | 2007-02-02 | 2008-08-07 | Tarari, Inc. | Systems and methods for processing access control lists (acls) in network switches using regular expression matching logic |
| 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 |
| WO2008150827A1 (en) | 2007-05-29 | 2008-12-11 | Smithkline Beecham Corporation | Naphthyridine, derivatives as p13 kinase inhibitors |
| KR20100025553A (ko) | 2007-06-05 | 2010-03-09 | 쉐링 코포레이션 | 암 치료용 ｅｒｋ 억제제로서의 폴리사이클릭 인다졸 유도체 및 이의 용도 |
| US7776877B2 (en) | 2007-06-22 | 2010-08-17 | Chemocentryx, Inc. | N-(2-(hetaryl)aryl) arylsulfonamides and N-(2-(hetaryl) hetaryl arylsulfonamides |
| US20100317863A1 (en) | 2007-07-25 | 2010-12-16 | Boehringer Ingelheim International Gmbh | Glucocorticoid Mimetics, Methods of Making Them, Pharmaceutical Compositions and Uses Thereof |
| US20110190280A1 (en) | 2007-08-29 | 2011-08-04 | George Adjabeng | Thiazole And Oxazole Kinase Inhibitors |
| WO2009035997A2 (en) | 2007-09-14 | 2009-03-19 | Cara Therapeutics, Inc. | Benzo-fused heterocycles |
| RU2364597C1 (ru) | 2007-12-14 | 2009-08-20 | Андрей Александрович Иващенко | ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ Hh-СИГНАЛЬНОГО КАСКАДА, ЛЕКАРСТВЕННЫЕ КОМПОЗИЦИИ НА ИХ ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С АББЕРАНТНОЙ АКТИВНОСТЬЮ Hh СИГНАЛЬНОЙ СИСТЕМЫ |
| US7960377B2 (en) | 2008-03-28 | 2011-06-14 | Cara Therapeutics, Inc. | Substituted pyridoxazines |
| JP5502077B2 (ja) | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | 新規な化合物 |
| ES2445199T3 (es) | 2008-06-05 | 2014-02-28 | Glaxo Group Limited | Derivados de benzpirazol como inhibidores de PI3-quinasas |
| ES2566339T3 (es) | 2008-06-05 | 2016-04-12 | Glaxo Group Limited | Derivados de 4-carboxamida indazol útiles como inhibidores de PI3-quinasas |
| CA2727373A1 (en) | 2008-06-09 | 2009-12-17 | Sanofi-Aventis | Annelated n-heterocyclic sulfonamides with oxadiazolone headgroup, processes for their preparation and their use as pharmaceuticals |
| EP2288605B1 (en) | 2008-06-09 | 2014-06-25 | Sanofi | Annelated pyrrolidin sulfonamides with oxadiazolone headgroup, processes for their preparation and their use as pharmaceuticals |
| WO2009157196A1 (ja) | 2008-06-25 | 2009-12-30 | 武田薬品工業株式会社 | アミド化合物 |
| WO2010017827A1 (en) | 2008-08-14 | 2010-02-18 | European Molecular Biology Laboratory | 6-substituted 1-sulfonyl-2, 3-dihydro-indole derivatives for the treatment of proliferative diseases |
| PL2344471T3 (pl) | 2008-10-02 | 2013-12-31 | Taisho Pharmaceutical Co Ltd | Pochodna 7-piperydynoalkilo-3,4-dihydrochinolonu |
| EP2181710A1 (en) | 2008-10-28 | 2010-05-05 | Phenex Pharmaceuticals AG | Ligands for modulation of orphan receptor-gamma (NR1F3) activity |
| WO2010050837A1 (ru) | 2008-10-28 | 2010-05-06 | Haskin Lev Yakovlevich | Ветроэнергетическая установка |
| WO2010057101A2 (en) | 2008-11-17 | 2010-05-20 | Schering Corporation | Compounds useful as hiv blockers |
| JP2012509274A (ja) | 2008-11-19 | 2012-04-19 | シェーリング コーポレイション | ジアシルグリセロールアシルトランスフェラーゼの阻害薬 |
| CN102264743B (zh) | 2008-11-25 | 2015-02-11 | 罗彻斯特大学 | Mlk抑制剂及其使用方法 |
| JP5628828B2 (ja) | 2008-12-19 | 2014-11-19 | サートリス ファーマシューティカルズ， インコーポレイテッド | チアゾロピリジンサーチュイン調節化合物 |
| TW201030007A (en) | 2009-02-06 | 2010-08-16 | Gruenenthal Gmbh | Substituted spiro-amides as b1r modulators |
| US8524751B2 (en) | 2009-03-09 | 2013-09-03 | GlaxoSmithKline Intellecutual Property Development | 4-oxadiazol-2-YL-indazoles as inhibitors of P13 kinases |
| TW201102391A (en) | 2009-03-31 | 2011-01-16 | Biogen Idec Inc | Certain substituted pyrimidines, pharmaceutical compositions thereof, and methods for their use |
| WO2010123139A1 (ja) | 2009-04-24 | 2010-10-28 | 持田製薬株式会社 | スルファモイル基を有するアリールカルボキサミド誘導体 |
| CN102459253B (zh) | 2009-04-30 | 2015-03-25 | 葛兰素集团有限公司 | 作为pi3-激酶抑制剂的*唑取代的吲唑化合物 |
| 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 |
| US8119683B2 (en) | 2009-08-10 | 2012-02-21 | Taipei Medical University | Aryl substituted sulfonamide compounds and their use as anticancer agents |
| US9556201B2 (en) | 2009-10-29 | 2017-01-31 | Glaxosmithkline Llc | Bicyclic pyridines and analogs as sirtuin modulators |
| EP2507223A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of p13 kinases |
| US20120238559A1 (en) | 2009-12-03 | 2012-09-20 | Glaxo Group Limited | Novel compounds |
| WO2011067366A1 (en) | 2009-12-03 | 2011-06-09 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
| JP2013514385A (ja) | 2009-12-18 | 2013-04-25 | ヤンセン ファーマシューティカ エヌ．ベー． | エストロゲン関連受容体αモジュレーターとしての置換アミノチアゾロンインダゾール |
| WO2011103189A1 (en) | 2010-02-16 | 2011-08-25 | Uwm Research Foundation, Inc. | Methods of reducing virulence in bacteria |
| EP3064204A1 (en) | 2010-03-01 | 2016-09-07 | GTx, Inc. | Compounds for treatment of cancer |
| US9290499B2 (en) | 2010-05-19 | 2016-03-22 | The University Of North Carolina At Chapel Hill | Pyrazolopyrimidine compounds for the treatment of cancer |
| JP5965402B2 (ja) | 2010-09-08 | 2016-08-03 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｎ−［５−［４−（５−｛［（２ｒ，６ｓ）−２，６−ジメチル−４−モルホリニル］メチル｝−１，３−オキサゾール−２−イル）−１ｈ−インダゾール−６−イル］−２−（メチルオキシ）−３−ピリジニル］メタンスルホンアミドの多形体および塩 |
| WO2012032065A1 (en) | 2010-09-08 | 2012-03-15 | Glaxo Group Limited | Indazole derivatives for use in the treatment of influenza virus infection |
| WO2012037108A1 (en) | 2010-09-13 | 2012-03-22 | Glaxosmithkline Llc | Aminoquinoline derivatives as antiviral agents |
| JP6063870B2 (ja) | 2010-11-08 | 2017-01-18 | ライセラ・コーポレイション | ＲＯＲγ活性の阻害用のＮ−スルホニル化テトラヒドロキノリンおよび関連二環化合物および病気の治療 |
| 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 |
| JP6157358B2 (ja) | 2010-12-22 | 2017-07-05 | ルートヴィヒ‐マクシミリアン‐ユニバーシタット ミュンヘン | 有機亜鉛錯体ならびに有機亜鉛錯体を作製および使用するための方法 |
| EP2487159A1 (en) | 2011-02-11 | 2012-08-15 | MSD Oss B.V. | RorgammaT inhibitors |
| EP2511263A1 (en) | 2011-04-14 | 2012-10-17 | Phenex Pharmaceuticals AG | Pyrrolo sulfonamide compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (RORgamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases |
| JP2014166961A (ja) | 2011-06-20 | 2014-09-11 | Dainippon Sumitomo Pharma Co Ltd | 新規インダゾール誘導体 |
| KR20150013500A (ko) | 2012-05-08 | 2015-02-05 | 머크 샤프 앤드 돔 코포레이션 | Ror감마 활성의 억제를 위한 비시클릭 술폰 화합물 및 질환의 치료 |
| RU2014149136A (ru) | 2012-05-08 | 2016-07-10 | Мерк Шарп И Доум Корп. | ТЕТРАГИДРОНАФТИРИДИНОВЫЕ И РОДСТВЕННЫЕ БИЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ ДЛЯ ИНГИБИРОВАНИЯ RORγ АКТИВНОСТИ И ЛЕЧЕНИЯ ЗАБОЛЕВАНИЯ |
| 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 |
| WO2014026330A1 (en) | 2012-08-15 | 2014-02-20 | Merck Sharp & Dohme Corp. | 3-AMINOCYCLOALKYL COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF |
| WO2015008234A1 (en) | 2013-07-17 | 2015-01-22 | Glenmark Pharmaceuticals S.A. | Bicyclic heterocyclic compounds as ror gamma modulators |
| 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 |
| 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 |
| US9783511B2 (en) | 2013-12-20 | 2017-10-10 | Lycera Corporation | Carbamate benzoxazine propionic acids and acid derivatives for modulation of RORgamma activity and the treatment of disease |
| US9663502B2 (en) | 2013-12-20 | 2017-05-30 | Lycera Corporation | 2-Acylamidomethyl and sulfonylamidomethyl benzoxazine carbamates for inhibition of RORgamma activity and the treatment of disease |
| 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 |
| JP2016141632A (ja) * | 2015-01-30 | 2016-08-08 | 第一三共株式会社 | 縮合二環式ヘテロ環誘導体 |
| CA2975997A1 (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 |
| AU2016344111A1 (en) | 2015-10-27 | 2018-05-10 | Merck Sharp & Dohme Corp. | Substituted bicyclic pyrazole compounds as RORgammaT inhibitors and uses thereof |
| CA3002850A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as rorgammat inhibitors and uses thereof |
| JP2018531958A (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阻害薬としてのヘテロアリール置換安息香酸及びその使用 |
-
2016
- 2016-10-27 CA CA3002850A patent/CA3002850A1/en not_active Abandoned
- 2016-10-27 RU RU2018117503A patent/RU2018117503A/ru not_active Application Discontinuation
- 2016-10-27 JP JP2018521300A patent/JP2018535958A/ja not_active Ceased
- 2016-10-27 EP EP16860768.7A patent/EP3368539B1/en active Active
- 2016-10-27 MX MX2018005004A patent/MX2018005004A/es unknown
- 2016-10-27 AU AU2016344115A patent/AU2016344115A1/en not_active Abandoned
- 2016-10-27 WO PCT/US2016/059063 patent/WO2017075182A1/en not_active Ceased
- 2016-10-27 US US15/770,256 patent/US10287272B2/en active Active
- 2016-10-27 CN CN201680076306.2A patent/CN108431009A/zh active Pending
- 2016-10-27 KR KR1020187014954A patent/KR20180070697A/ko not_active Withdrawn
-
2018
- 2018-04-23 IL IL258870A patent/IL258870A/en unknown
-
2019
- 2019-03-18 US US16/356,172 patent/US10689369B2/en active Active
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