JP2014513703A5 - - Google Patents
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- JP2014513703A5 JP2014513703A5 JP2014510758A JP2014510758A JP2014513703A5 JP 2014513703 A5 JP2014513703 A5 JP 2014513703A5 JP 2014510758 A JP2014510758 A JP 2014510758A JP 2014510758 A JP2014510758 A JP 2014510758A JP 2014513703 A5 JP2014513703 A5 JP 2014513703A5
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- JP
- Japan
- Prior art keywords
- phenyl
- substituted
- pyrrolo
- octahydro
- compound according
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
- -1 haloalkoxy compound Chemical class 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims 19
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 206010012601 diabetes mellitus Diseases 0.000 claims 9
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 201000001320 Atherosclerosis Diseases 0.000 claims 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims 6
- 206010061218 Inflammation Diseases 0.000 claims 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 6
- 208000008589 Obesity Diseases 0.000 claims 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 230000004064 dysfunction Effects 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 230000004054 inflammatory process Effects 0.000 claims 6
- 230000002107 myocardial effect Effects 0.000 claims 6
- 235000020824 obesity Nutrition 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- TZYWCWPNWKEQCG-ANEWXZNUSA-N (3ar,7as)-2-[2-(2,4-dichlorophenyl)-2-hydroxyethyl]-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C([C@@H]1CN(C[C@@H]1C1=O)CC(O)C=2C(=CC(Cl)=CC=2)Cl)CN1C1=CC=C(OCC(F)(F)F)C=C1 TZYWCWPNWKEQCG-ANEWXZNUSA-N 0.000 claims 2
- OOPXPUHSUWIQHN-PBHICJAKSA-N (3ar,7as)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-[2-(trifluoromethoxy)phenyl]sulfonyl-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)OC(F)(F)F)C[C@H]2CC1 OOPXPUHSUWIQHN-PBHICJAKSA-N 0.000 claims 2
- ICURKDZAOKAZKG-OWQGQXMQSA-N (3as,5s,6ar)-5-(butoxymethyl)-5-hydroxy-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@H]1C[C@@](C[C@@H]1C1=O)(O)COCCCC)N1C1=CC=C(OC(F)(F)F)C=C1 ICURKDZAOKAZKG-OWQGQXMQSA-N 0.000 claims 2
- RUZIVNMLRPKBGI-KUBVQFIISA-N (3as,7ar)-1-(2-phenylacetyl)-5-[4-(trifluoromethoxy)phenyl]-2,3,3a,6,7,7a-hexahydro-1h-pyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)[C@H](CNC2C(=O)CC=3C=CC=CC=3)[C@H]2CC1 RUZIVNMLRPKBGI-KUBVQFIISA-N 0.000 claims 2
- IOHFWOZJENTFLA-XJKSGUPXSA-N (3as,7ar)-2-(2-chlorophenyl)sulfonyl-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)[C@@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)Cl)C[C@@H]2CC1 IOHFWOZJENTFLA-XJKSGUPXSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- SDRXORFVMCHESD-CHEUHSMRSA-N (3ar,7as)-1-(2-phenylacetyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3,3a,6,7,7a-hexahydro-1h-pyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@@H](CNC2C(=O)CC=3C=CC=CC=3)[C@@H]2CC1 SDRXORFVMCHESD-CHEUHSMRSA-N 0.000 claims 1
- JWCAWYZVCBQCHU-PBHICJAKSA-N (3ar,7as)-2-(2-chlorophenyl)sulfonyl-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)Cl)C[C@H]2CC1 JWCAWYZVCBQCHU-PBHICJAKSA-N 0.000 claims 1
- URZPTRWITOLAHH-CJNGLKHVSA-N (3ar,7as)-2-(2-chloropyridin-3-yl)sulfonyl-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@H]2CN(S(=O)(=O)C=3C(=NC=CC=3)Cl)C[C@H]2CC1 URZPTRWITOLAHH-CJNGLKHVSA-N 0.000 claims 1
- UTIMXNSQVSYIOG-PBHICJAKSA-N (3ar,7as)-2-(2-hydroxyphenyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound OC1=CC=CC=C1N1C[C@@H]2C(=O)N(C=3C=CC(OCC(F)(F)F)=CC=3)CC[C@@H]2C1 UTIMXNSQVSYIOG-PBHICJAKSA-N 0.000 claims 1
- TUTZPAJFLXAIQH-PBHICJAKSA-N (3ar,7as)-2-(3,3-dimethylbutanoyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C([C@@H]1CN(C[C@@H]1C1=O)C(=O)CC(C)(C)C)CN1C1=CC=C(OCC(F)(F)F)C=C1 TUTZPAJFLXAIQH-PBHICJAKSA-N 0.000 claims 1
- QLGSFDRAOBTLSJ-BEFAXECRSA-N (3ar,7as)-2-(benzenesulfonyl)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@H]2CN(S(=O)(=O)C=3C=CC=CC=3)C[C@H]2CC1 QLGSFDRAOBTLSJ-BEFAXECRSA-N 0.000 claims 1
- VUKYNERAKZLTOZ-UZLBHIALSA-N (3ar,7as)-2-[2-(4-fluorophenyl)acetyl]-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(F)=CC=C1CC(=O)N1C[C@@H]2C(=O)N(C=3C=CC(OCC(F)(F)F)=CC=3)CC[C@@H]2C1 VUKYNERAKZLTOZ-UZLBHIALSA-N 0.000 claims 1
- BMTUEDGSYHQHFI-NQIIRXRSSA-N (3ar,7as)-2-[2-(4-methylphenyl)acetyl]-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(C)=CC=C1CC(=O)N1C[C@@H]2C(=O)N(C=3C=CC(OCC(F)(F)F)=CC=3)CC[C@@H]2C1 BMTUEDGSYHQHFI-NQIIRXRSSA-N 0.000 claims 1
- BWVIKPJQQKIUGB-PBHICJAKSA-N (3ar,7as)-5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-[2-(trifluoromethyl)phenyl]sulfonyl-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OCC(F)(F)F)=CC=C1N1C(=O)[C@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)C[C@H]2CC1 BWVIKPJQQKIUGB-PBHICJAKSA-N 0.000 claims 1
- ZOSXIEYYQRCFQH-XEGUGMAKSA-N (3as,5s,6ar)-5-hydroxy-5-(2,2,2-trifluoroethoxymethyl)-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@H]1C[C@](C[C@@H]1C1=O)(COCC(F)(F)F)O)N1C1=CC=C(OC(F)(F)F)C=C1 ZOSXIEYYQRCFQH-XEGUGMAKSA-N 0.000 claims 1
- FWMIDUCEURWGLJ-DCPHZVHLSA-N (3as,5s,6ar)-5-hydroxy-5-(phenoxymethyl)-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@]1(O)C[C@@H]2C(=O)N(C[C@@H]2C1)C=1C=CC(OC(F)(F)F)=CC=1)OC1=CC=CC=C1 FWMIDUCEURWGLJ-DCPHZVHLSA-N 0.000 claims 1
- UQTFGVGNOYPZBT-NUTKFTJISA-N (3as,5s,6ar)-5-hydroxy-5-(propoxymethyl)-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@H]1C[C@@](C[C@@H]1C1=O)(O)COCCC)N1C1=CC=C(OC(F)(F)F)C=C1 UQTFGVGNOYPZBT-NUTKFTJISA-N 0.000 claims 1
- JQQBOTWLJXCTBZ-KEXXGOCASA-N (3as,6ar)-5-(anilinomethyl)-5-hydroxy-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@H]1C(=O)N(C[C@@H]1C1)C=2C=CC(OC(F)(F)F)=CC=2)C1(O)CNC1=CC=CC=C1 JQQBOTWLJXCTBZ-KEXXGOCASA-N 0.000 claims 1
- SNVFIFXXEAAXLK-XPFLZZBLSA-N (3as,6ar)-5-hydroxy-5-propyl-2-[4-(trifluoromethoxy)phenyl]-3a,4,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-3-one Chemical compound C([C@@H]1CC(C[C@@H]1C1=O)(O)CCC)N1C1=CC=C(OC(F)(F)F)C=C1 SNVFIFXXEAAXLK-XPFLZZBLSA-N 0.000 claims 1
- BVXPXCFIGDWPIB-DNVCBOLYSA-N (3as,6as)-5-(4-ethylphenyl)-4-oxo-n-[4-(trifluoromethoxy)phenyl]-3,3a,6,6a-tetrahydro-1h-pyrrolo[3,4-c]pyrrole-2-carboxamide Chemical compound C1=CC(CC)=CC=C1N1C(=O)[C@@H]2CN(C(=O)NC=3C=CC(OC(F)(F)F)=CC=3)C[C@@H]2C1 BVXPXCFIGDWPIB-DNVCBOLYSA-N 0.000 claims 1
- UTWATDQGGKALAL-SUMWQHHRSA-N (3as,7ar)-2-(2-chlorobenzoyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)[C@@H]2CN(C(=O)C=3C(=CC=CC=3)Cl)C[C@@H]2CC1 UTWATDQGGKALAL-SUMWQHHRSA-N 0.000 claims 1
- YXAQHOMOMXWBST-XJKSGUPXSA-N (3as,7ar)-2-(2-methylpropylsulfonyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C([C@H]1CN(C[C@H]1C1=O)S(=O)(=O)CC(C)C)CN1C1=CC=C(OC(F)(F)F)C=C1 YXAQHOMOMXWBST-XJKSGUPXSA-N 0.000 claims 1
- FIADIBYFRWITEN-XJKSGUPXSA-N (3as,7ar)-2-(3-methylbutanoyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C([C@H]1CN(C[C@H]1C1=O)C(=O)CC(C)C)CN1C1=CC=C(OC(F)(F)F)C=C1 FIADIBYFRWITEN-XJKSGUPXSA-N 0.000 claims 1
- TWMYWSDGOVHDKS-WMLDXEAASA-N (3as,7ar)-2-(3-methylbutylsulfonyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C([C@H]1CN(C[C@H]1C1=O)S(=O)(=O)CCC(C)C)CN1C1=CC=C(OC(F)(F)F)C=C1 TWMYWSDGOVHDKS-WMLDXEAASA-N 0.000 claims 1
- MFAMMXPGEWSZTR-KBXCAEBGSA-N (3as,7ar)-2-(4-fluorobenzoyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 MFAMMXPGEWSZTR-KBXCAEBGSA-N 0.000 claims 1
- WPSQOKLLQVOTBZ-SCLBCKFNSA-N (3as,7ar)-2-(4-fluorophenyl)sulfonyl-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 WPSQOKLLQVOTBZ-SCLBCKFNSA-N 0.000 claims 1
- UVQXTGZXMGDYMH-GHTZIAJQSA-N (3as,7ar)-2-(4-propan-2-ylbenzoyl)-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(C(C)C)=CC=C1C(=O)N1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 UVQXTGZXMGDYMH-GHTZIAJQSA-N 0.000 claims 1
- DXVHIIDHQSBIDF-HNAYVOBHSA-N (3as,7ar)-2-[(4-fluorophenyl)methyl]-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(F)=CC=C1CN1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 DXVHIIDHQSBIDF-HNAYVOBHSA-N 0.000 claims 1
- ABDCELHRYJDOPX-QFBILLFUSA-N (3as,7ar)-2-benzylsulfonyl-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)[C@@H]2CN(S(=O)(=O)CC=3C=CC=CC=3)C[C@@H]2CC1 ABDCELHRYJDOPX-QFBILLFUSA-N 0.000 claims 1
- VTFOQHWGMPFGSF-SCLBCKFNSA-N (3as,7ar)-4-oxo-n,5-bis[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 VTFOQHWGMPFGSF-SCLBCKFNSA-N 0.000 claims 1
- RPGIAZHLHQUFBN-SCLBCKFNSA-N (3as,7ar)-n-(4-fluorophenyl)-4-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)N1C[C@H]2C(=O)N(C=3C=CC(OC(F)(F)F)=CC=3)CC[C@H]2C1 RPGIAZHLHQUFBN-SCLBCKFNSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- SDRNBXQJIXBCGH-QWLMFLSESA-N 2-[(3ar,7as)-4-oxo-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridin-2-yl]-n-(4-fluorophenyl)-3-methylbutanamide Chemical compound C([C@@H]1CN(C[C@@H]1C1=O)C(C(C)C)C(=O)NC=2C=CC(F)=CC=2)CN1C1=CC=C(OCC(F)(F)F)C=C1 SDRNBXQJIXBCGH-QWLMFLSESA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- AGYMBTDCKVMYIT-UHFFFAOYSA-N FC(OC1=CC=C(C=C1)NC(=O)N1C(C2CNCC2C1)C1=CC=C(C=C1)OC(F)(F)F)(F)F Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1C(C2CNCC2C1)C1=CC=C(C=C1)OC(F)(F)F)(F)F AGYMBTDCKVMYIT-UHFFFAOYSA-N 0.000 claims 1
- 102000000019 Sterol Esterase Human genes 0.000 claims 1
- 108010055297 Sterol Esterase Proteins 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZCLNJVVEHPLNDO-BSBHGOPBSA-N n-[(3as,6ar)-3-oxo-2-[4-(trifluoromethoxy)phenyl]-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-2-chlorobenzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)[C@H]2CC(NS(=O)(=O)C=3C(=CC=CC=3)Cl)C[C@H]2C1 ZCLNJVVEHPLNDO-BSBHGOPBSA-N 0.000 claims 1
- NYMDZLNOQPHCMN-CJNGLKHVSA-N tert-butyl (3ar,7as)-4-oxo-5-[4-(2,2,2-trifluoroethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-2-carboxylate Chemical compound C([C@@H]1CN(C[C@@H]1C1=O)C(=O)OC(C)(C)C)CN1C1=CC=C(OCC(F)(F)F)C=C1 NYMDZLNOQPHCMN-CJNGLKHVSA-N 0.000 claims 1
- LMSUQMJAMATPBV-DOMZBBRYSA-N tert-butyl (3ar,7as)-4-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3,3a,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-2-carboxylate Chemical compound C([C@@H]1CN(C[C@@H]1C1=O)C(=O)OC(C)(C)C)CN1C1=CC=C(OC(F)(F)F)C=C1 LMSUQMJAMATPBV-DOMZBBRYSA-N 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11166437.1 | 2011-05-17 | ||
| EP11166437 | 2011-05-17 | ||
| PCT/EP2012/058852 WO2012156339A1 (en) | 2011-05-17 | 2012-05-14 | New hexahydrocyclopentapyrrolone, hexahydropyrrolopyrrolone, octahydropyrrolopyridinone and octahydropyridinone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014513703A JP2014513703A (ja) | 2014-06-05 |
| JP2014513703A5 true JP2014513703A5 (OSRAM) | 2015-07-02 |
Family
ID=46124329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510758A Pending JP2014513703A (ja) | 2011-05-17 | 2012-05-14 | 新規ヘキサヒドロシクロペンタピロロン、ヘキサヒドロピロロピロロン、オクタヒドロピロロピリジノン及びオクタヒドロピリジノン化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8501768B2 (OSRAM) |
| EP (1) | EP2709984B1 (OSRAM) |
| JP (1) | JP2014513703A (OSRAM) |
| KR (1) | KR20140042814A (OSRAM) |
| CN (1) | CN103562180B (OSRAM) |
| BR (1) | BR112013028368A2 (OSRAM) |
| CA (1) | CA2832334A1 (OSRAM) |
| ES (1) | ES2537591T3 (OSRAM) |
| MX (1) | MX346980B (OSRAM) |
| RU (1) | RU2013153898A (OSRAM) |
| WO (1) | WO2012156339A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8497288B2 (en) * | 2011-05-09 | 2013-07-30 | Hoffmann-La Roche Inc. | Hexahydropyrroloimidazolone compounds |
| AR097794A1 (es) | 2013-09-26 | 2016-04-13 | Mnemosyne Pharmaceuticals Inc | Moduladores octahidro-ciclopenta[c]pirrol negativos de nr2b |
| JO3579B1 (ar) | 2014-09-26 | 2020-07-05 | Luc Therapeutics Inc | مُعدِلات تفاغرية سالبة لمستقبل nr2b من المركب n-ألكيل أريل-5-أوكسي أريل-ثامن هيدرو-خماسي الحلقة [c] بيرول |
| WO2016149169A1 (en) * | 2015-03-13 | 2016-09-22 | Abbvie Inc. | (indazol-4-yl)hexahydropyrrolopyrrolones and method of use |
| EP3538123A4 (en) | 2016-11-10 | 2020-10-14 | Keros Therapeutics, Inc. | ACTIVIN RECEPTOR TYPE IIA VARIANTS AND THEIR METHODS OF USE |
| CN120399032A (zh) | 2018-01-12 | 2025-08-01 | 科乐斯疗法公司 | 激活素受体iib型变体及其使用方法 |
| EP4121088A4 (en) | 2020-03-20 | 2024-07-03 | Keros Therapeutics, Inc. | Methods of using activin receptor type iib variants |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942354A1 (de) * | 1999-09-04 | 2001-03-08 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneimitteln |
| HUP0302772A3 (en) * | 2000-03-07 | 2007-03-28 | Sanofi Aventis Deutschland | Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one and use thereof for inhibiting hormone-sensitive lipase |
| HUP0400531A3 (en) * | 2000-12-01 | 2006-05-29 | Cerep Sa | Hydantoin compounds useful as anti-inflammatory agents and pharmaceutical compositions containing them |
| CN101115741A (zh) * | 2005-02-15 | 2008-01-30 | 诺和诺德公司 | 3,4-二氢-1h-异喹啉-2-羧酸5-氨基吡啶-2-基酯 |
| CN101336243A (zh) * | 2005-12-05 | 2008-12-31 | 因塞特公司 | 内酰胺化合物和其使用方法 |
| DK2035379T3 (da) * | 2006-04-25 | 2010-09-06 | Lilly Co Eli | Inhibitorer af 11-beta-hydroxysteroiddehydrogenase 1 |
| CA2685543A1 (en) * | 2007-04-27 | 2008-11-13 | Sanofi-Aventis | 2-heteroaryl-pyrrolo[3,4-c]pyrrole derivatives and their use as scd inhibitors |
| WO2010108268A1 (en) | 2009-03-23 | 2010-09-30 | Merck Frosst Canada Ltd. | Heterocyclic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| KR101859409B1 (ko) * | 2009-10-23 | 2018-05-18 | 얀센 파마슈티카 엔.브이. | 오렉신 수용체 조절제로서의 이치환된 옥타하이드로피롤로［3,4-ｃ］피롤 |
| UY33227A (es) * | 2010-02-19 | 2011-09-30 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de la cdk4/6 |
-
2012
- 2012-05-04 US US13/463,863 patent/US8501768B2/en not_active Expired - Fee Related
- 2012-05-14 CA CA2832334A patent/CA2832334A1/en not_active Abandoned
- 2012-05-14 KR KR1020137033414A patent/KR20140042814A/ko not_active Withdrawn
- 2012-05-14 EP EP12721814.7A patent/EP2709984B1/en not_active Not-in-force
- 2012-05-14 CN CN201280023662.XA patent/CN103562180B/zh not_active Expired - Fee Related
- 2012-05-14 ES ES12721814.7T patent/ES2537591T3/es active Active
- 2012-05-14 MX MX2013011628A patent/MX346980B/es active IP Right Grant
- 2012-05-14 RU RU2013153898/04A patent/RU2013153898A/ru not_active Application Discontinuation
- 2012-05-14 JP JP2014510758A patent/JP2014513703A/ja active Pending
- 2012-05-14 BR BR112013028368A patent/BR112013028368A2/pt not_active IP Right Cessation
- 2012-05-14 WO PCT/EP2012/058852 patent/WO2012156339A1/en not_active Ceased
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