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
- CXVRKQACCUYWFM-JQBYJRRVSA-N 4-[6-[(3aR,6aS)-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)N1C[C@@H]2COC[C@@H]2C1 CXVRKQACCUYWFM-JQBYJRRVSA-N 0.000 claims 1
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- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 208000024340 acute graft versus host disease Diseases 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 208000017760 chronic graft versus host disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000036566 epidermal hyperplasia Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| WO2017075182A1 (en) * | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as rorgammat inhibitors and uses thereof |
| WO2017075185A1 (en) | 2015-10-27 | 2017-05-04 | Merck Sharp & Dohme Corp. | Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof |
| CA3094988A1 (en) | 2018-03-30 | 2019-10-03 | Biotheryx, Inc. | Thienopyrimidinone compounds |
| WO2020229398A1 (de) | 2019-05-14 | 2020-11-19 | Bayer Aktiengesellschaft | (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
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| 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 |
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| MX367341B (es) | 2012-05-08 | 2019-08-14 | Merck Sharp & Dohme | Tetrahidronaftiridina y compuestos biciclicos relacionados para la inhibicion de la actividad de rorgamma y el tratamiento de enfermedades. |
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-
2016
- 2016-10-27 WO PCT/US2016/059063 patent/WO2017075182A1/en not_active Ceased
- 2016-10-27 AU AU2016344115A patent/AU2016344115A1/en not_active Abandoned
- 2016-10-27 JP JP2018521300A patent/JP2018535958A/ja not_active Ceased
- 2016-10-27 KR KR1020187014954A patent/KR20180070697A/ko not_active Withdrawn
- 2016-10-27 MX MX2018005004A patent/MX2018005004A/es unknown
- 2016-10-27 US US15/770,256 patent/US10287272B2/en active Active
- 2016-10-27 EP EP16860768.7A patent/EP3368539B1/en active Active
- 2016-10-27 CA CA3002850A patent/CA3002850A1/en not_active Abandoned
- 2016-10-27 CN CN201680076306.2A patent/CN108431009A/zh active Pending
- 2016-10-27 RU RU2018117503A patent/RU2018117503A/ru not_active Application Discontinuation
-
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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