JP2020512300A5 - - Google Patents
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- JP2020512300A5 JP2020512300A5 JP2019545893A JP2019545893A JP2020512300A5 JP 2020512300 A5 JP2020512300 A5 JP 2020512300A5 JP 2019545893 A JP2019545893 A JP 2019545893A JP 2019545893 A JP2019545893 A JP 2019545893A JP 2020512300 A5 JP2020512300 A5 JP 2020512300A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- hydrogen
- present
- membered
- 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 189
- 229910052717 sulfur Inorganic materials 0.000 claims 153
- 229910052739 hydrogen Inorganic materials 0.000 claims 144
- 239000001257 hydrogen Substances 0.000 claims 134
- 125000000623 heterocyclic group Chemical group 0.000 claims 93
- 150000002431 hydrogen Chemical class 0.000 claims 91
- 229910052760 oxygen Inorganic materials 0.000 claims 90
- 125000005842 heteroatom Chemical group 0.000 claims 78
- 125000005843 halogen group Chemical group 0.000 claims 69
- 229910052799 carbon Inorganic materials 0.000 claims 64
- 150000001721 carbon Chemical group 0.000 claims 49
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 43
- 125000004432 carbon atom Chemical group C* 0.000 claims 40
- -1 substituted Chemical class 0.000 claims 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 31
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000002837 carbocyclic group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 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 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052705 radium Inorganic materials 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- QHXCPVZGMVAYOZ-QHFRKORRSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-methyl-1,1-dioxothiane-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CC(S(CC1)(=O)=O)C QHXCPVZGMVAYOZ-QHFRKORRSA-N 0.000 claims 2
- MQRUBWHKVFGFSJ-CDJVIQHXSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-6-oxopiperidine-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CNC(CC1)=O MQRUBWHKVFGFSJ-CDJVIQHXSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- XTDAYXIUIHCDSJ-MGCNMGEWSA-N (2R)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-hydroxypropanamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC([C@@H](C)O)=O XTDAYXIUIHCDSJ-MGCNMGEWSA-N 0.000 claims 1
- XSFNSQHWZYZLAD-AALWMKDKSA-N (2S)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1-(2-cyanoethyl)-5-oxopyrrolidine-2-carboxamide Chemical compound C(#N)CCN1[C@@H](CCC1=O)C(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F XSFNSQHWZYZLAD-AALWMKDKSA-N 0.000 claims 1
- NSOZNCDGAWNAJW-YOUFYPILSA-N (2S)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3,3,3-trifluoro-2-hydroxypropanamide Chemical compound FC([C@H](C(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)O)(F)F NSOZNCDGAWNAJW-YOUFYPILSA-N 0.000 claims 1
- NFVMQTJJLOTRQU-GPQLQYNLSA-N (3R)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-4,4,4-trifluoro-3-hydroxybutanamide Chemical compound FC([C@@H](CC(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)O)(F)F NFVMQTJJLOTRQU-GPQLQYNLSA-N 0.000 claims 1
- QYNFVEHOGUQHMA-NHCICSSKSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-(2-hydroxy-2-methylpropyl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NCC(C)(C)O QYNFVEHOGUQHMA-NHCICSSKSA-N 0.000 claims 1
- RORQXNGSZJNUGB-JLRUASKGSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-[(1-hydroxycyclobutyl)methyl]-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NCC1(CCC1)O RORQXNGSZJNUGB-JLRUASKGSA-N 0.000 claims 1
- BYPRNDXXUCKHDZ-VIICAESSSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-[(1-hydroxycyclopentyl)methyl]-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NCC1(CCCC1)O BYPRNDXXUCKHDZ-VIICAESSSA-N 0.000 claims 1
- HWGPLLMBVOATBQ-PSODJOGVSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-[(1-methylsulfonylpyrrolidin-3-yl)methyl]-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NCC1CN(CC1)S(=O)(=O)C HWGPLLMBVOATBQ-PSODJOGVSA-N 0.000 claims 1
- PFZGVNNSJDKHBA-PXDNOPAQSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-[(2R)-2-hydroxypropyl]-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NC[C@@H](C)O PFZGVNNSJDKHBA-PXDNOPAQSA-N 0.000 claims 1
- CTPFTSBIUAYSTN-VIICAESSSA-N (3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-N-[(4-hydroxyoxan-4-yl)methyl]-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)C(=O)NCC1(CCOCC1)O CTPFTSBIUAYSTN-VIICAESSSA-N 0.000 claims 1
- HBFSRQDUIXVHAT-YWEFRBEISA-N (3R,3aS,9bS)-N-(2,3-dihydroxy-3-methylbutyl)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalene-3-carboxamide Chemical compound OC(CNC(=O)[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)C(C)(C)O HBFSRQDUIXVHAT-YWEFRBEISA-N 0.000 claims 1
- RGBQAUAZQBXYOA-SRQWTHTNSA-N (3S)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1-(2-cyanoethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C(#N)CCN1C[C@H](CC1=O)C(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F RGBQAUAZQBXYOA-SRQWTHTNSA-N 0.000 claims 1
- JBWSOLBITSIVFP-REKIFZGPSA-N (3S)-N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-5-oxo-1-(trideuteriomethyl)pyrrolidine-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)[C@@H]1CN(C(C1)=O)C([2H])([2H])[2H] JBWSOLBITSIVFP-REKIFZGPSA-N 0.000 claims 1
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 1
- XJVCBQQIEWBUJL-UHFFFAOYSA-N 1,1-dioxothiane-4-carboxamide Chemical compound NC(=O)C1CCS(=O)(=O)CC1 XJVCBQQIEWBUJL-UHFFFAOYSA-N 0.000 claims 1
- RPJRJUVGGDVVDF-UHFFFAOYSA-N 1,1-dioxothiane-4-carboxylic acid Chemical compound OC(=O)C1CCS(=O)(=O)CC1 RPJRJUVGGDVVDF-UHFFFAOYSA-N 0.000 claims 1
- ZOUXWWBOVSADDJ-YZUZCNPQSA-N 1-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3-(2-hydroxy-2-methylpropyl)urea Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)NCC(C)(C)O ZOUXWWBOVSADDJ-YZUZCNPQSA-N 0.000 claims 1
- XSLZOVDVKRRVRO-TUNNFDKTSA-N 1-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3-(2-hydroxyethyl)urea Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)NCCO XSLZOVDVKRRVRO-TUNNFDKTSA-N 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 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
- NYCMADVMUKSWCE-SILINQRBSA-N C(C([2H])([2H])[2H])(=O)N1CCC(CC1)(C(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)O Chemical compound C(C([2H])([2H])[2H])(=O)N1CCC(CC1)(C(=O)N[C@@H]1CC[C@@]2([C@H]1CCC1=CC(=CC=C21)C(C(F)(F)F)(C(F)(F)F)F)S(=O)(=O)C1=CC=C(C=C1)F)O NYCMADVMUKSWCE-SILINQRBSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- GYJXNPAXBRDCAD-ARACBONISA-N FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CNC(C1)=O Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CNC(C1)=O GYJXNPAXBRDCAD-ARACBONISA-N 0.000 claims 1
- XSLZOVDVKRRVRO-LSFFMHSVSA-N FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)NCC([2H])([2H])O Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)NCC([2H])([2H])O XSLZOVDVKRRVRO-LSFFMHSVSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- LOOWXSUDJJEUCC-JBRSBNLGSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1,1-dioxothiane-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CCS(CC1)(=O)=O LOOWXSUDJJEUCC-JBRSBNLGSA-N 0.000 claims 1
- CBHXZNHHAYIMEF-PPJWLVRDSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1-hydroxycyclohexane-1-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(CCCCC1)O CBHXZNHHAYIMEF-PPJWLVRDSA-N 0.000 claims 1
- KQFDYOLDJVTCIH-MIZPHKNDSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1-hydroxycyclopropane-1-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(CC1)O KQFDYOLDJVTCIH-MIZPHKNDSA-N 0.000 claims 1
- SOVPTYOHXWCJGU-PPJWLVRDSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-1-methyl-2-oxopyridine-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1=CC(N(C=C1)C)=O SOVPTYOHXWCJGU-PPJWLVRDSA-N 0.000 claims 1
- NACPOCRTATWMHW-TXCIXCGHSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2,2,2-trideuterioacetamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(C([2H])([2H])[2H])=O NACPOCRTATWMHW-TXCIXCGHSA-N 0.000 claims 1
- JZUVTKBHDNIOHD-MIZPHKNDSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-hydroxy-2-methylpropanamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(C(C)(C)O)=O JZUVTKBHDNIOHD-MIZPHKNDSA-N 0.000 claims 1
- NDJFPJNHWITLET-CLCZQPDDSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-methyl-2-morpholin-4-ylpropanamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(C(C)(N1CCOCC1)C)=O NDJFPJNHWITLET-CLCZQPDDSA-N 0.000 claims 1
- DASFAWUVRWZPRE-QYBSIVRTSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-methyl-5-oxopyrrolidine-2-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(NC(CC1)=O)C DASFAWUVRWZPRE-QYBSIVRTSA-N 0.000 claims 1
- LVXLSBWEYGATHS-CDJVIQHXSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-2-oxopiperidine-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1CC(NCC1)=O LVXLSBWEYGATHS-CDJVIQHXSA-N 0.000 claims 1
- AFUBNXYCARZLIL-YZUZCNPQSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3-hydroxy-2,2-dimethylpropanamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(C(CO)(C)C)=O AFUBNXYCARZLIL-YZUZCNPQSA-N 0.000 claims 1
- HIKFSOMQAYWOLS-YZUZCNPQSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3-hydroxy-3-methylbutanamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(CC(C)(C)O)=O HIKFSOMQAYWOLS-YZUZCNPQSA-N 0.000 claims 1
- AGXPSKZTBXHXKM-YZUZCNPQSA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-3-methyloxetane-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(COC1)C AGXPSKZTBXHXKM-YZUZCNPQSA-N 0.000 claims 1
- XVZYXRRHNUIONL-SGIRGMQISA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-4-hydroxy-1,1-dioxothiane-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(CCS(CC1)(=O)=O)O XVZYXRRHNUIONL-SGIRGMQISA-N 0.000 claims 1
- LFAYVOLNYZLVHP-SGIRGMQISA-N N-[(3R,3aS,9bS)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-1,2,3,3a,4,5-hexahydrocyclopenta[a]naphthalen-3-yl]-4-hydroxyoxane-4-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)[C@@]12[C@@H](CCC3=CC(=CC=C13)C(C(F)(F)F)(C(F)(F)F)F)[C@@H](CC2)NC(=O)C1(CCOCC1)O LFAYVOLNYZLVHP-SGIRGMQISA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- 208000026935 allergic disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
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| US62/419,607 | 2016-11-09 | ||
| PCT/US2017/060501 WO2018089402A1 (en) | 2016-11-09 | 2017-11-08 | Tricyclic sulfones as ror gamma modulators |
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| JP2020512300A JP2020512300A (ja) | 2020-04-23 |
| JP2020512300A5 true JP2020512300A5 (https=) | 2020-11-12 |
| JP7182553B2 JP7182553B2 (ja) | 2022-12-02 |
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| 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 |
| 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 |
| WO2023232870A1 (en) | 2022-05-31 | 2023-12-07 | Immunic Ag | Rorg/rorgt modulators for the treatment of virus infections like covid-19 |
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| KR20080095885A (ko) * | 2006-01-20 | 2008-10-29 | 쉐링 코포레이션 | 벤젠설포닐-크로만, 티오크로만, 테트라하이드로나프탈렌 및 관련된 감마 세크라타제 억제제 |
| WO2009008980A2 (en) | 2007-07-05 | 2009-01-15 | Schering Corporation | Tetrahydropyranochromene gamma secretase inhibitors |
| US8618123B2 (en) * | 2007-07-17 | 2013-12-31 | Merck Sharp & Dohme Corp. | Benzenesulfonyl-chromane, thiochromane, tetrahydronaphthalene and related gamma secretase inhibitors |
| EP2925313A4 (en) | 2012-11-29 | 2016-05-11 | Merck Sharp & Dohme | SPIROCYCLIC SULPHONES AS GAMMA SECRETASE INHIBITORS |
| WO2015103509A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Pyrrolidinyl sulfone derivatives and their use as ror gamma modulators |
| WO2015103508A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | CARBOCYCLIC SULFONE RORγ MODULATORS |
| CN106061947B (zh) | 2014-01-06 | 2019-12-03 | 百时美施贵宝公司 | 环己基砜RORγ调节剂 |
| WO2015103510A1 (en) | 2014-01-06 | 2015-07-09 | Bristol-Myers Squibb Company | Heterocyclic sulfone as ror-gamma modulators |
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- 2017-11-08 JP JP2019545893A patent/JP7182553B2/ja active Active
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