JP2019530720A5 - - Google Patents
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- JP2019530720A5 JP2019530720A5 JP2019520081A JP2019520081A JP2019530720A5 JP 2019530720 A5 JP2019530720 A5 JP 2019530720A5 JP 2019520081 A JP2019520081 A JP 2019520081A JP 2019520081 A JP2019520081 A JP 2019520081A JP 2019530720 A5 JP2019530720 A5 JP 2019530720A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- hexahydro
- pyrrolo
- perfluoropropane
- single enantiomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 50
- -1 Substituted Chemical class 0.000 claims 46
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 229910052717 sulfur Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 35
- 125000005842 heteroatom Chemical group 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 229910052760 oxygen Inorganic materials 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- ZSSCVXMAHNMCPY-UHFFFAOYSA-N propanenitrile 2,2,2-trifluoroacetic acid Chemical compound CCC#N.OC(=O)C(F)(F)F ZSSCVXMAHNMCPY-UHFFFAOYSA-N 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- UFSQHLCNTQHWHK-UMZMAHLQSA-N (1R,3S,4R)-4-[9a-(3-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinoline-7-carbonyl]-3-methylcyclohexane-1-carboxylic acid Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C12C(CCC=3C=C(N=CC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]1[C@H](C[C@@H](CC1)C(=O)O)C UFSQHLCNTQHWHK-UMZMAHLQSA-N 0.000 claims 1
- CSKDKDGLTHHIDT-UMZMAHLQSA-N (1R,3S,4R)-4-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinoline-7-carbonyl]-3-methylcyclohexane-1-carboxylic acid Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(N=CC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]1[C@H](C[C@@H](CC1)C(=O)O)C CSKDKDGLTHHIDT-UMZMAHLQSA-N 0.000 claims 1
- QBMHAHBUIROKGC-WXBXVUQPSA-N (1R,3S,4R)-4-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]-3-methylcyclohexane-1-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(C=NC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]1[C@H](C[C@@H](CC1)C(=O)N)C QBMHAHBUIROKGC-WXBXVUQPSA-N 0.000 claims 1
- ABUIFSRVXZIKJL-JHZSQARYSA-N (1R,3S,4R)-4-[9b-(3-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-methylcyclohexane-1-carboxylic acid Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C12C=3C=CC(=NC=3CCC1N(CC2)C(=O)[C@H]1[C@H](C[C@@H](CC1)C(=O)O)C)C(C(F)(F)F)(C(F)(F)F)F ABUIFSRVXZIKJL-JHZSQARYSA-N 0.000 claims 1
- SUQJXYBCTNLWFL-JHZSQARYSA-N (1R,3S,4R)-4-[9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-methylcyclohexane-1-carboxylic acid Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C=3C=CC(=NC=3CCC1N(CC2)C(=O)[C@H]1[C@H](C[C@@H](CC1)C(=O)O)C)C(C(F)(F)F)(C(F)(F)F)F SUQJXYBCTNLWFL-JHZSQARYSA-N 0.000 claims 1
- SKMPHPWGJSCYBA-WBERWSKZSA-N (1R,3S,4R)-4-[9b-(benzenesulfonyl)-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-methylcyclohexane-1-carboxylic acid Chemical compound C[C@H]1C[C@@H](CC[C@H]1C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=CC=C1)C(=O)O SKMPHPWGJSCYBA-WBERWSKZSA-N 0.000 claims 1
- LQOLTWLGUXAQIY-ORYOPMSGSA-N (3R,5R)-5-[9b-(3-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-fluoro-1-(2-hydroxy-2-methylpropyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@H](C1)C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC(=CC=C1)F)CC(C)(C)O)=O LQOLTWLGUXAQIY-ORYOPMSGSA-N 0.000 claims 1
- OFERFDOYQSSRKG-ORYOPMSGSA-N (3R,5R)-5-[9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-fluoro-1-(2-hydroxy-2-methylpropyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@H](C1)C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)CC(C)(C)O)=O OFERFDOYQSSRKG-ORYOPMSGSA-N 0.000 claims 1
- JCZNISQCKZIDTP-DTUBHJHESA-N (3R,5S)-5-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]-3-fluoro-1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@@H](C1)C(=O)N1CCC2(C1CCC=1C=C(C=NC2=1)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)CCO)=O JCZNISQCKZIDTP-DTUBHJHESA-N 0.000 claims 1
- ZUEHSODYHTYQIB-KEMIWIHDSA-N (3R,5S)-5-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]-3-fluoro-1-(trideuteriomethyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@@H](C1)C(=O)N1CCC2(C1CCC=1C=C(C=NC2=1)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)C([2H])([2H])[2H])=O ZUEHSODYHTYQIB-KEMIWIHDSA-N 0.000 claims 1
- LQOLTWLGUXAQIY-WFTVRUROSA-N (3R,5S)-5-[9b-(3-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-fluoro-1-(2-hydroxy-2-methylpropyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@@H](C1)C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC(=CC=C1)F)CC(C)(C)O)=O LQOLTWLGUXAQIY-WFTVRUROSA-N 0.000 claims 1
- OFERFDOYQSSRKG-WFTVRUROSA-N (3R,5S)-5-[9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-3-fluoro-1-(2-hydroxy-2-methylpropyl)pyrrolidin-2-one Chemical compound F[C@H]1C(N([C@@H](C1)C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)CC(C)(C)O)=O OFERFDOYQSSRKG-WFTVRUROSA-N 0.000 claims 1
- JQNSMMANVWQLSP-UHFFFAOYSA-N 1-[9a-(3-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinolin-7-yl]-2,2,2-trifluoroethanone Chemical compound FC(C(=O)N1CCC2(C1CCC=1C=C(N=CC2=1)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC(=CC=C1)F)(F)F JQNSMMANVWQLSP-UHFFFAOYSA-N 0.000 claims 1
- XFXUWLCSLQBALW-UHFFFAOYSA-N 1-[9a-(3-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinoline-7-carbonyl]-2-(2-hydroxy-2-methylpropyl)pyrazolidin-3-one Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C12C(CCC=3C=C(N=CC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)N1N(C(CC1)=O)CC(C)(C)O XFXUWLCSLQBALW-UHFFFAOYSA-N 0.000 claims 1
- WUKGOEHRLQKELV-UHFFFAOYSA-N 1-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinoline-7-carbonyl]-2-(2-hydroxy-2-methylpropyl)pyrazolidin-3-one Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(N=CC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)N1N(C(CC1)=O)CC(C)(C)O WUKGOEHRLQKELV-UHFFFAOYSA-N 0.000 claims 1
- CARJIACDJLBVSL-UHFFFAOYSA-N 1-[9b-(benzenesulfonyl)-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-2-(2-hydroxy-2-methylpropyl)pyrazolidin-3-one Chemical compound OC(CN1N(CCC1=O)C(=O)N1CCC2(C=3C=CC(=NC=3CCC21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=CC=C1)(C)C CARJIACDJLBVSL-UHFFFAOYSA-N 0.000 claims 1
- SDOIFCUJDSQNRP-UHFFFAOYSA-N 1-[9b-(benzenesulfonyl)-7-[(2,6-dichlorophenyl)methoxy]-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinolin-3-yl]-2,2,2-trifluoroethanone Chemical compound ClC1=C(COC2=NC=3CCC4C(C=3C=C2)(CCN4C(C(F)(F)F)=O)S(=O)(=O)C2=CC=CC=C2)C(=CC=C1)Cl SDOIFCUJDSQNRP-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- BUFKNEMFCZHEPM-UNMCHZSKSA-N 3-[(2S)-2-[7-[(2,6-dichlorophenyl)methoxy]-9b-(4-fluorophenyl)sulfonyl-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-5-oxopyrrolidin-1-yl]propanenitrile Chemical compound ClC1=C(COC2=NC=3CCC4C(C=3C=C2)(CCN4C(=O)[C@H]2N(C(CC2)=O)CCC#N)S(=O)(=O)C2=CC=C(C=C2)F)C(=CC=C1)Cl BUFKNEMFCZHEPM-UNMCHZSKSA-N 0.000 claims 1
- CHWBNSJXLYXNSH-QCVKPBSVSA-N 3-[(2S)-2-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]isoquinoline-7-carbonyl]-5-oxopyrrolidin-1-yl]propanenitrile Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(N=CC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]1N(C(CC1)=O)CCC#N CHWBNSJXLYXNSH-QCVKPBSVSA-N 0.000 claims 1
- LAASMHMDWXOTPL-LQAIBEDLSA-N 3-[(2S)-2-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]-5-oxopyrrolidin-1-yl]propanenitrile Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(C=NC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]1N(C(CC1)=O)CCC#N LAASMHMDWXOTPL-LQAIBEDLSA-N 0.000 claims 1
- ILNOJESQIBYYJI-QCVKPBSVSA-N 3-[(2S)-2-[9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]-5-oxopyrrolidin-1-yl]propanenitrile Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C=3C=CC(=NC=3CCC1N(CC2)C(=O)[C@H]1N(C(CC1)=O)CCC#N)C(C(F)(F)F)(C(F)(F)F)F ILNOJESQIBYYJI-QCVKPBSVSA-N 0.000 claims 1
- GGKDFFGZVLLFNH-UHFFFAOYSA-N 4-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]bicyclo[2.2.2]octane-1-carboxylic acid hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(C=NC13)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)C21CCC(CC2)(CC1)C(=O)O GGKDFFGZVLLFNH-UHFFFAOYSA-N 0.000 claims 1
- PSDYNJKEIGVAKQ-UHFFFAOYSA-N 4-[9b-(benzenesulfonyl)-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-pyrrolo[3,2-f]quinoline-3-carbonyl]bicyclo[2.2.2]octane-1-carboxylic acid Chemical compound FC(C(C(F)(F)F)(C1=NC=2CCC3C(C=2C=C1)(CCN3C(=O)C12CCC(CC1)(CC2)C(=O)O)S(=O)(=O)C1=CC=CC=C1)F)(F)F PSDYNJKEIGVAKQ-UHFFFAOYSA-N 0.000 claims 1
- PFQMJSXPCCBWKI-UHFFFAOYSA-N 6-[9a-(4-fluorophenyl)sulfonyl-3-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6,6a,8,9-tetrahydro-5H-pyrrolo[2,3-h]quinoline-7-carbonyl]spiro[3.3]heptane-2-carboxylic acid Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C12C(CCC=3C=C(C=NC1=3)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)C1CC2(CC(C2)C(=O)O)C1 PFQMJSXPCCBWKI-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- UUVFTWGUGQMBMV-UHFFFAOYSA-N FC(C(=O)O)(F)F.CC(CCCC)=O Chemical compound FC(C(=O)O)(F)F.CC(CCCC)=O UUVFTWGUGQMBMV-UHFFFAOYSA-N 0.000 claims 1
- SWORBWPWOVKDFT-PTXCKITFSA-N FC(C(=O)O)(F)F.FC=1C=C(C=CC1)S(=O)(=O)C12C(CCC=3C=C(N=CC13)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]2N(C(CC2)=O)CCC#N Chemical compound FC(C(=O)O)(F)F.FC=1C=C(C=CC1)S(=O)(=O)C12C(CCC=3C=C(N=CC13)C(C(F)(F)F)(C(F)(F)F)F)N(CC2)C(=O)[C@H]2N(C(CC2)=O)CCC#N SWORBWPWOVKDFT-PTXCKITFSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- ULBXCSDXOZAJHM-UHFFFAOYSA-N propanal 2,2,2-trifluoroacetic acid Chemical compound CCC=O.OC(=O)C(F)(F)F ULBXCSDXOZAJHM-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662407702P | 2016-10-13 | 2016-10-13 | |
| US62/407,702 | 2016-10-13 | ||
| PCT/US2017/056257 WO2018071620A1 (en) | 2016-10-13 | 2017-10-12 | Heterocyclic sulfones as ror gamma modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019530720A JP2019530720A (ja) | 2019-10-24 |
| JP2019530720A5 true JP2019530720A5 (https=) | 2020-11-19 |
| JP7083823B2 JP7083823B2 (ja) | 2022-06-13 |
Family
ID=60162317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019520081A Active JP7083823B2 (ja) | 2016-10-13 | 2017-10-12 | ＲＯＲγ修飾因子としてのヘテロ環スルホン類 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10934286B2 (https=) |
| EP (1) | EP3526218B1 (https=) |
| JP (1) | JP7083823B2 (https=) |
| KR (1) | KR102506326B1 (https=) |
| CN (1) | CN110049985B (https=) |
| ES (1) | ES2872005T3 (https=) |
| WO (1) | WO2018071620A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021524850A (ja) | 2018-05-17 | 2021-09-16 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ＲＯＲγ調節剤としての三環スルホン化合物 |
| JP7542538B2 (ja) | 2018-09-18 | 2024-08-30 | ニカング セラピューティクス， インコーポレイテッド | Ｓｒｃホモロジー－２ホスファターゼ阻害剤としての縮合三環式環誘導体 |
| WO2020231766A1 (en) * | 2019-05-13 | 2020-11-19 | Bristol-Myers Squibb Company | AGONISTS OF ROR GAMMAt |
| CN114981245A (zh) * | 2020-01-24 | 2022-08-30 | 百时美施贵宝公司 | 作为RORγ调节剂的三环砜 |
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| KR20080095885A (ko) * | 2006-01-20 | 2008-10-29 | 쉐링 코포레이션 | 벤젠설포닐-크로만, 티오크로만, 테트라하이드로나프탈렌 및 관련된 감마 세크라타제 억제제 |
| WO2008150364A1 (en) | 2007-05-23 | 2008-12-11 | Merck & Co., Inc. | Cyclopropyl pyrrolidine orexin receptor antagonists |
| EP2368886A1 (en) * | 2010-03-01 | 2011-09-28 | Phenex Pharmaceuticals AG | Novel compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (ROR gamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune desease |
| WO2014141132A1 (en) | 2013-03-14 | 2014-09-18 | Naeja Pharmaceutical Inc. | NEW HETEROCYCLIC COMPOUNDS AND THEIR USE AS ANTIBACTERIAL AGENTS AND β-LACTAMASE INHIBITORS |
| JP6397488B2 (ja) * | 2013-09-20 | 2018-09-26 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ＲＯＲγ調節因子 |
| WO2015103509A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Pyrrolidinyl sulfone derivatives and their use as ror gamma modulators |
| KR102114536B1 (ko) * | 2015-05-07 | 2020-05-22 | 브리스톨-마이어스 스큅 컴퍼니 | RORγ 조정제로서의 트리시클릭 술폰 |
| EP3523279A1 (en) * | 2016-10-10 | 2019-08-14 | Bristol-Myers Squibb Company | Tricyclic sulfones as ror gamma modulators |
-
2017
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- 2017-10-12 WO PCT/US2017/056257 patent/WO2018071620A1/en not_active Ceased
- 2017-10-12 CN CN201780076364.XA patent/CN110049985B/zh active Active
- 2017-10-12 EP EP17788067.1A patent/EP3526218B1/en active Active
- 2017-10-12 KR KR1020197013216A patent/KR102506326B1/ko active Active
- 2017-10-12 JP JP2019520081A patent/JP7083823B2/ja active Active
- 2017-10-12 US US16/341,474 patent/US10934286B2/en active Active
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