RU2008107336A - Новые 1-арил-з-азабицикло{3.1.0.} гексаны: получение и применение для лечения психоневрологических расстройств - Google Patents
Новые 1-арил-з-азабицикло{3.1.0.} гексаны: получение и применение для лечения психоневрологических расстройств Download PDFInfo
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- RU2008107336A RU2008107336A RU2008107336/04A RU2008107336A RU2008107336A RU 2008107336 A RU2008107336 A RU 2008107336A RU 2008107336/04 A RU2008107336/04 A RU 2008107336/04A RU 2008107336 A RU2008107336 A RU 2008107336A RU 2008107336 A RU2008107336 A RU 2008107336A
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- RU
- Russia
- Prior art keywords
- hexane
- aza
- bicyclo
- methyl
- dichlorophenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 87
- 125000000217 alkyl group Chemical group 0.000 claims abstract 65
- 150000002367 halogens Chemical class 0.000 claims abstract 52
- 229910052736 halogen Inorganic materials 0.000 claims abstract 48
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 42
- 125000001424 substituent group Chemical group 0.000 claims abstract 34
- -1 cyano, hydroxy Chemical group 0.000 claims abstract 33
- 150000003839 salts Chemical class 0.000 claims abstract 31
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 17
- 150000002431 hydrogen Chemical group 0.000 claims abstract 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 14
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 12
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract 11
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims abstract 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims abstract 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 37
- 208000015114 central nervous system disease Diseases 0.000 claims 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 210000003169 central nervous system Anatomy 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 12
- 239000003937 drug carrier Substances 0.000 claims 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 239000000126 substance Substances 0.000 claims 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 7
- 230000004700 cellular uptake Effects 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 208000024891 symptom Diseases 0.000 claims 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 5
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 230000000035 biogenic effect Effects 0.000 claims 4
- 229960003638 dopamine Drugs 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 4
- 239000002858 neurotransmitter agent Substances 0.000 claims 4
- 229960002748 norepinephrine Drugs 0.000 claims 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 4
- 229940076279 serotonin Drugs 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- YCEPPWZMXQMHRV-MFKMUULPSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CC)=CC=C(Cl)C(Cl)=C1 YCEPPWZMXQMHRV-MFKMUULPSA-N 0.000 claims 3
- RKQIRCIDIAEOQG-YPMHNXCESA-N (1r,5s)-1-(3-fluoro-4-methylphenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C)=CC=C(C)C(F)=C1 RKQIRCIDIAEOQG-YPMHNXCESA-N 0.000 claims 3
- WDFKHQBXXRJHEC-KCJUWKMLSA-N (1r,5s)-1-[4-chloro-3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(C(F)(F)F)=CC([C@]23[C@H](C2)CNC3)=C1 WDFKHQBXXRJHEC-KCJUWKMLSA-N 0.000 claims 3
- HKHCSWPSUSWGLI-CABCVRRESA-N (1r,5s)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@@]34CNC[C@H]4C3)=CC=C21 HKHCSWPSUSWGLI-CABCVRRESA-N 0.000 claims 3
- COLJOGVSPPXZNW-CVEARBPZSA-N (1r,5s)-3-methyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@@]34C[C@@H]3CN(C4)C)=CC=C21 COLJOGVSPPXZNW-CVEARBPZSA-N 0.000 claims 3
- RKQIRCIDIAEOQG-WCQYABFASA-N (1s,5r)-1-(3-fluoro-4-methylphenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C)=CC=C(C)C(F)=C1 RKQIRCIDIAEOQG-WCQYABFASA-N 0.000 claims 3
- HKHCSWPSUSWGLI-LSDHHAIUSA-N (1s,5r)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@]34CNC[C@@H]4C3)=CC=C21 HKHCSWPSUSWGLI-LSDHHAIUSA-N 0.000 claims 3
- COLJOGVSPPXZNW-JKSUJKDBSA-N (1s,5r)-3-methyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@]34C[C@H]3CN(C4)C)=CC=C21 COLJOGVSPPXZNW-JKSUJKDBSA-N 0.000 claims 3
- XROLNRZXVDVRQA-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(F)C(F)=C1 XROLNRZXVDVRQA-UHFFFAOYSA-N 0.000 claims 3
- NEPFRIDVWPAQEY-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(F)C(Cl)=C1 NEPFRIDVWPAQEY-UHFFFAOYSA-N 0.000 claims 3
- SHGZSVFUPPCUIE-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(F)C(Cl)=C1 SHGZSVFUPPCUIE-UHFFFAOYSA-N 0.000 claims 3
- ZQDUBTPWXSFQGA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1(CN(C)C2)C2C1 ZQDUBTPWXSFQGA-UHFFFAOYSA-N 0.000 claims 3
- RBSUWUVPTHHLHV-UHFFFAOYSA-N 1-naphthalen-2-yl-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CC3CN(C4)C(C)C)=CC=C21 RBSUWUVPTHHLHV-UHFFFAOYSA-N 0.000 claims 3
- CIRWXGMYHWXKHE-UHFFFAOYSA-N 3-ethyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CC3CN(C4)CC)=CC=C21 CIRWXGMYHWXKHE-UHFFFAOYSA-N 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- GJNUJXJSBQTLMX-DOMZBBRYSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-(2-methylpropyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CC(C)C)=CC=C(Cl)C(Cl)=C1 GJNUJXJSBQTLMX-DOMZBBRYSA-N 0.000 claims 2
- MBFDPIYMOIZLLZ-SKDRFNHKSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C)=CC=C(Cl)C(Cl)=C1 MBFDPIYMOIZLLZ-SKDRFNHKSA-N 0.000 claims 2
- HYTFHLKGMUVBOD-RISCZKNCSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C(C)C)=CC=C(Cl)C(Cl)=C1 HYTFHLKGMUVBOD-RISCZKNCSA-N 0.000 claims 2
- CBICSBDJSHIILP-RISCZKNCSA-N (1r,5s)-1-(3,4-dichlorophenyl)-3-propyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CCC)=CC=C(Cl)C(Cl)=C1 CBICSBDJSHIILP-RISCZKNCSA-N 0.000 claims 2
- XROLNRZXVDVRQA-MFKMUULPSA-N (1r,5s)-1-(3,4-difluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CC)=CC=C(F)C(F)=C1 XROLNRZXVDVRQA-MFKMUULPSA-N 0.000 claims 2
- DJQGRQUSJZIZJM-KCJUWKMLSA-N (1r,5s)-1-(3-chloro-4-fluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(F)=CC=C1[C@]1(CNC2)[C@@H]2C1 DJQGRQUSJZIZJM-KCJUWKMLSA-N 0.000 claims 2
- NEPFRIDVWPAQEY-MFKMUULPSA-N (1r,5s)-1-(3-chloro-4-fluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CC)=CC=C(F)C(Cl)=C1 NEPFRIDVWPAQEY-MFKMUULPSA-N 0.000 claims 2
- MIRHDPAAZCWTAT-SKDRFNHKSA-N (1r,5s)-1-(3-chloro-4-fluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C)=CC=C(F)C(Cl)=C1 MIRHDPAAZCWTAT-SKDRFNHKSA-N 0.000 claims 2
- SHGZSVFUPPCUIE-RISCZKNCSA-N (1r,5s)-1-(3-chloro-4-fluorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C(C)C)=CC=C(F)C(Cl)=C1 SHGZSVFUPPCUIE-RISCZKNCSA-N 0.000 claims 2
- AFKUTJAEGSFAJE-PWSUYJOCSA-N (1r,5s)-1-(3-fluoro-4-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(C)=CC=C1[C@]1(CNC2)[C@@H]2C1 AFKUTJAEGSFAJE-PWSUYJOCSA-N 0.000 claims 2
- QJLIHKDLLYUQQE-KCJUWKMLSA-N (1r,5s)-1-(4-chloro-3-fluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(F)=CC([C@]23[C@H](C2)CNC3)=C1 QJLIHKDLLYUQQE-KCJUWKMLSA-N 0.000 claims 2
- JQVAHOXPFLQHIU-SKDRFNHKSA-N (1r,5s)-1-(4-chloro-3-fluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C)=CC=C(Cl)C(F)=C1 JQVAHOXPFLQHIU-SKDRFNHKSA-N 0.000 claims 2
- JXCCCXJMHZUFOM-IUODEOHRSA-N (1r,5s)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C([C@@]34CNC[C@H]4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-IUODEOHRSA-N 0.000 claims 2
- ARMJFBWEHFAODY-DOMZBBRYSA-N (1r,5s)-3-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)CCCC)=CC=C(Cl)C(Cl)=C1 ARMJFBWEHFAODY-DOMZBBRYSA-N 0.000 claims 2
- DLNQEYMDSOUAEK-YGRLFVJLSA-N (1r,5s)-3-cyclopropyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@]1(CN(C2)C3CC3)[C@@H]2C1 DLNQEYMDSOUAEK-YGRLFVJLSA-N 0.000 claims 2
- NOINBIBBSXQXQL-CZUORRHYSA-N (1r,5s)-3-methyl-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C([C@@]34C[C@@H]3CN(C4)C)=CC=CC2=C1 NOINBIBBSXQXQL-CZUORRHYSA-N 0.000 claims 2
- HUWILRCAXKHYEE-ABAIWWIYSA-N (1r,5s)-3-tert-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C(C)(C)C)=CC=C(Cl)C(Cl)=C1 HUWILRCAXKHYEE-ABAIWWIYSA-N 0.000 claims 2
- GJNUJXJSBQTLMX-SWLSCSKDSA-N (1s,5r)-1-(3,4-dichlorophenyl)-3-(2-methylpropyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CC(C)C)=CC=C(Cl)C(Cl)=C1 GJNUJXJSBQTLMX-SWLSCSKDSA-N 0.000 claims 2
- YCEPPWZMXQMHRV-GXFFZTMASA-N (1s,5r)-1-(3,4-dichlorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CC)=CC=C(Cl)C(Cl)=C1 YCEPPWZMXQMHRV-GXFFZTMASA-N 0.000 claims 2
- MBFDPIYMOIZLLZ-JOYOIKCWSA-N (1s,5r)-1-(3,4-dichlorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C)=CC=C(Cl)C(Cl)=C1 MBFDPIYMOIZLLZ-JOYOIKCWSA-N 0.000 claims 2
- HYTFHLKGMUVBOD-SMDDNHRTSA-N (1s,5r)-1-(3,4-dichlorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C(C)C)=CC=C(Cl)C(Cl)=C1 HYTFHLKGMUVBOD-SMDDNHRTSA-N 0.000 claims 2
- CBICSBDJSHIILP-SMDDNHRTSA-N (1s,5r)-1-(3,4-dichlorophenyl)-3-propyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCC)=CC=C(Cl)C(Cl)=C1 CBICSBDJSHIILP-SMDDNHRTSA-N 0.000 claims 2
- XROLNRZXVDVRQA-GXFFZTMASA-N (1s,5r)-1-(3,4-difluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CC)=CC=C(F)C(F)=C1 XROLNRZXVDVRQA-GXFFZTMASA-N 0.000 claims 2
- DJQGRQUSJZIZJM-GZMMTYOYSA-N (1s,5r)-1-(3-chloro-4-fluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(F)=CC=C1[C@@]1(CNC2)[C@H]2C1 DJQGRQUSJZIZJM-GZMMTYOYSA-N 0.000 claims 2
- NEPFRIDVWPAQEY-GXFFZTMASA-N (1s,5r)-1-(3-chloro-4-fluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CC)=CC=C(F)C(Cl)=C1 NEPFRIDVWPAQEY-GXFFZTMASA-N 0.000 claims 2
- MIRHDPAAZCWTAT-JOYOIKCWSA-N (1s,5r)-1-(3-chloro-4-fluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C)=CC=C(F)C(Cl)=C1 MIRHDPAAZCWTAT-JOYOIKCWSA-N 0.000 claims 2
- SHGZSVFUPPCUIE-SMDDNHRTSA-N (1s,5r)-1-(3-chloro-4-fluorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C(C)C)=CC=C(F)C(Cl)=C1 SHGZSVFUPPCUIE-SMDDNHRTSA-N 0.000 claims 2
- AFKUTJAEGSFAJE-CMPLNLGQSA-N (1s,5r)-1-(3-fluoro-4-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(C)=CC=C1[C@@]1(CNC2)[C@H]2C1 AFKUTJAEGSFAJE-CMPLNLGQSA-N 0.000 claims 2
- QJLIHKDLLYUQQE-GZMMTYOYSA-N (1s,5r)-1-(4-chloro-3-fluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(F)=CC([C@@]23[C@@H](C2)CNC3)=C1 QJLIHKDLLYUQQE-GZMMTYOYSA-N 0.000 claims 2
- JQVAHOXPFLQHIU-JOYOIKCWSA-N (1s,5r)-1-(4-chloro-3-fluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C)=CC=C(Cl)C(F)=C1 JQVAHOXPFLQHIU-JOYOIKCWSA-N 0.000 claims 2
- WDFKHQBXXRJHEC-GZMMTYOYSA-N (1s,5r)-1-[4-chloro-3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(C(F)(F)F)=CC([C@@]23[C@@H](C2)CNC3)=C1 WDFKHQBXXRJHEC-GZMMTYOYSA-N 0.000 claims 2
- VHCIUNKECNSBDV-JOYOIKCWSA-N (1s,5r)-1-[4-chloro-3-(trifluoromethyl)phenyl]-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C)=CC=C(Cl)C(C(F)(F)F)=C1 VHCIUNKECNSBDV-JOYOIKCWSA-N 0.000 claims 2
- JXCCCXJMHZUFOM-WFASDCNBSA-N (1s,5r)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C([C@]34CNC[C@@H]4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-WFASDCNBSA-N 0.000 claims 2
- RBSUWUVPTHHLHV-ZWKOTPCHSA-N (1s,5r)-1-naphthalen-2-yl-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@]34C[C@H]3CN(C4)C(C)C)=CC=C21 RBSUWUVPTHHLHV-ZWKOTPCHSA-N 0.000 claims 2
- ARMJFBWEHFAODY-SWLSCSKDSA-N (1s,5r)-3-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)CCCC)=CC=C(Cl)C(Cl)=C1 ARMJFBWEHFAODY-SWLSCSKDSA-N 0.000 claims 2
- DLNQEYMDSOUAEK-IINYFYTJSA-N (1s,5r)-3-cyclopropyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@@]1(CN(C2)C3CC3)[C@H]2C1 DLNQEYMDSOUAEK-IINYFYTJSA-N 0.000 claims 2
- NOINBIBBSXQXQL-BBRMVZONSA-N (1s,5r)-3-methyl-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C([C@]34C[C@H]3CN(C4)C)=CC=CC2=C1 NOINBIBBSXQXQL-BBRMVZONSA-N 0.000 claims 2
- HUWILRCAXKHYEE-XHDPSFHLSA-N (1s,5r)-3-tert-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@]23C[C@H]2CN(C3)C(C)(C)C)=CC=C(Cl)C(Cl)=C1 HUWILRCAXKHYEE-XHDPSFHLSA-N 0.000 claims 2
- UPYBZMLUEHYERX-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(Cl)C=C1Cl UPYBZMLUEHYERX-UHFFFAOYSA-N 0.000 claims 2
- NINMSEOZKXYKQY-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(Cl)C=C1Cl NINMSEOZKXYKQY-UHFFFAOYSA-N 0.000 claims 2
- COUWOHPJYMOZMK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(Cl)C=C1Cl COUWOHPJYMOZMK-UHFFFAOYSA-N 0.000 claims 2
- KCRITGUPBTXIOU-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-ethyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(F)C=C1F KCRITGUPBTXIOU-UHFFFAOYSA-N 0.000 claims 2
- QWPHEZZMMCGXHQ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(F)C=C1F QWPHEZZMMCGXHQ-UHFFFAOYSA-N 0.000 claims 2
- JAKNMMQWYASCBY-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(F)C=C1F JAKNMMQWYASCBY-UHFFFAOYSA-N 0.000 claims 2
- GJNUJXJSBQTLMX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-(2-methylpropyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC(C)C)CC2CC21C1=CC=C(Cl)C(Cl)=C1 GJNUJXJSBQTLMX-UHFFFAOYSA-N 0.000 claims 2
- HYTFHLKGMUVBOD-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(Cl)C(Cl)=C1 HYTFHLKGMUVBOD-UHFFFAOYSA-N 0.000 claims 2
- CBICSBDJSHIILP-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-propyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CCC)CC2CC21C1=CC=C(Cl)C(Cl)=C1 CBICSBDJSHIILP-UHFFFAOYSA-N 0.000 claims 2
- KPJWWZWHMZQVDR-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(F)=CC=C1C1(CNC2)C2C1 KPJWWZWHMZQVDR-UHFFFAOYSA-N 0.000 claims 2
- WXIVKHRXEAQSCE-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(F)C(F)=C1 WXIVKHRXEAQSCE-UHFFFAOYSA-N 0.000 claims 2
- NRGCBXVKYOUSIH-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(F)C(F)=C1 NRGCBXVKYOUSIH-UHFFFAOYSA-N 0.000 claims 2
- DJQGRQUSJZIZJM-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(F)=CC=C1C1(CNC2)C2C1 DJQGRQUSJZIZJM-UHFFFAOYSA-N 0.000 claims 2
- MIRHDPAAZCWTAT-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(F)C(Cl)=C1 MIRHDPAAZCWTAT-UHFFFAOYSA-N 0.000 claims 2
- HUGOTKRAEFZPCO-UHFFFAOYSA-N 1-(3-chloro-4-nitrophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C([N+]([O-])=O)C(Cl)=C1 HUGOTKRAEFZPCO-UHFFFAOYSA-N 0.000 claims 2
- WCECACQMBDOWNI-UHFFFAOYSA-N 1-(3-fluoro-4-methoxyphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(OC)=CC=C1C1(CNC2)C2C1 WCECACQMBDOWNI-UHFFFAOYSA-N 0.000 claims 2
- AFKUTJAEGSFAJE-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(C)=CC=C1C1(CNC2)C2C1 AFKUTJAEGSFAJE-UHFFFAOYSA-N 0.000 claims 2
- RKQIRCIDIAEOQG-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(C)C(F)=C1 RKQIRCIDIAEOQG-UHFFFAOYSA-N 0.000 claims 2
- PTODZCZLADSORB-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(C)C(F)=C1 PTODZCZLADSORB-UHFFFAOYSA-N 0.000 claims 2
- ZVTZIDFCOMHRAL-UHFFFAOYSA-N 1-(4-fluoro-3-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(F)C(C)=CC(C23C(C2)CNC3)=C1 ZVTZIDFCOMHRAL-UHFFFAOYSA-N 0.000 claims 2
- ZJDFOPYAGRPFLM-UHFFFAOYSA-N 1-(4-fluoro-3-methylphenyl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C)CC2CC21C1=CC=C(F)C(C)=C1 ZJDFOPYAGRPFLM-UHFFFAOYSA-N 0.000 claims 2
- SGPXKGOYAUAZHM-UHFFFAOYSA-N 1-(4-fluoro-3-methylphenyl)-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)C)CC2CC21C1=CC=C(F)C(C)=C1 SGPXKGOYAUAZHM-UHFFFAOYSA-N 0.000 claims 2
- LXRGASPBMFUCBR-UHFFFAOYSA-N 1-(4-fluoronaphthalen-1-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(F)=CC=C(C34C(C3)CNC4)C2=C1 LXRGASPBMFUCBR-UHFFFAOYSA-N 0.000 claims 2
- CCWSHTWDGSAUAU-UHFFFAOYSA-N 1-(4-fluoronaphthalen-1-yl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C34CC3CN(C4)C)=CC=C(F)C2=C1 CCWSHTWDGSAUAU-UHFFFAOYSA-N 0.000 claims 2
- JBEISIMRAMNVTP-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C)=CC=C(C34C(C3)CNC4)C2=C1 JBEISIMRAMNVTP-UHFFFAOYSA-N 0.000 claims 2
- PZSAUCRKLIVWSM-UHFFFAOYSA-N 1-(6-ethoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C1(CNC2)C2C1 PZSAUCRKLIVWSM-UHFFFAOYSA-N 0.000 claims 2
- XEECWPXYCFHQRV-UHFFFAOYSA-N 1-(6-ethoxynaphthalen-2-yl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C1(CN(C)C2)C2C1 XEECWPXYCFHQRV-UHFFFAOYSA-N 0.000 claims 2
- QGLYIJQWOLIXCL-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1(CNC2)C2C1 QGLYIJQWOLIXCL-UHFFFAOYSA-N 0.000 claims 2
- ZFAPCMDDVJKHMV-UHFFFAOYSA-N 1-[3-fluoro-4-(trifluoromethoxy)phenyl]-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(OC(F)(F)F)C(F)=CC(C23C(C2)CNC3)=C1 ZFAPCMDDVJKHMV-UHFFFAOYSA-N 0.000 claims 2
- JXCCCXJMHZUFOM-UHFFFAOYSA-N 1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C34CNCC4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-UHFFFAOYSA-N 0.000 claims 2
- HKHCSWPSUSWGLI-UHFFFAOYSA-N 1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CNCC4C3)=CC=C21 HKHCSWPSUSWGLI-UHFFFAOYSA-N 0.000 claims 2
- ARMJFBWEHFAODY-UHFFFAOYSA-N 3-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CCCC)CC2CC21C1=CC=C(Cl)C(Cl)=C1 ARMJFBWEHFAODY-UHFFFAOYSA-N 0.000 claims 2
- DLNQEYMDSOUAEK-UHFFFAOYSA-N 3-cyclopropyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CN(C2)C3CC3)C2C1 DLNQEYMDSOUAEK-UHFFFAOYSA-N 0.000 claims 2
- CDBBAUIFDCZSKO-UHFFFAOYSA-N 3-ethyl-1-(3-fluoro-4-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(C)C(F)=C1 CDBBAUIFDCZSKO-UHFFFAOYSA-N 0.000 claims 2
- ZKCNQDANIMJTBP-UHFFFAOYSA-N 3-ethyl-1-(4-fluoro-3-methylphenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1N(CC)CC2CC21C1=CC=C(F)C(C)=C1 ZKCNQDANIMJTBP-UHFFFAOYSA-N 0.000 claims 2
- PWPCFNCTRMMLFC-UHFFFAOYSA-N 3-methyl-1-(4-methylnaphthalen-1-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C34CC3CN(C4)C)=CC=C(C)C2=C1 PWPCFNCTRMMLFC-UHFFFAOYSA-N 0.000 claims 2
- NOINBIBBSXQXQL-UHFFFAOYSA-N 3-methyl-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C34CC3CN(C4)C)=CC=CC2=C1 NOINBIBBSXQXQL-UHFFFAOYSA-N 0.000 claims 2
- COLJOGVSPPXZNW-UHFFFAOYSA-N 3-methyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CC3CN(C4)C)=CC=C21 COLJOGVSPPXZNW-UHFFFAOYSA-N 0.000 claims 2
- HUWILRCAXKHYEE-UHFFFAOYSA-N 3-tert-butyl-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane Chemical compound C1N(C(C)(C)C)CC2CC21C1=CC=C(Cl)C(Cl)=C1 HUWILRCAXKHYEE-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 238000001308 synthesis method Methods 0.000 claims 2
- BRLQWZUYTZBJKN-VKHMYHEASA-N (-)-Epichlorohydrin Chemical group ClC[C@H]1CO1 BRLQWZUYTZBJKN-VKHMYHEASA-N 0.000 claims 1
- VHCIUNKECNSBDV-SKDRFNHKSA-N (1r,5s)-1-[4-chloro-3-(trifluoromethyl)phenyl]-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1([C@@]23C[C@@H]2CN(C3)C)=CC=C(Cl)C(C(F)(F)F)=C1 VHCIUNKECNSBDV-SKDRFNHKSA-N 0.000 claims 1
- RBSUWUVPTHHLHV-MSOLQXFVSA-N (1r,5s)-1-naphthalen-2-yl-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@@]34C[C@@H]3CN(C4)C(C)C)=CC=C21 RBSUWUVPTHHLHV-MSOLQXFVSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical compound C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000005888 cyclopropanation reaction Methods 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 210000004962 mammalian cell Anatomy 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- QJYHLROZBKJKDS-UHFFFAOYSA-N O=C(C1C2)NCC12[AlH2] Chemical compound O=C(C1C2)NCC12[AlH2] QJYHLROZBKJKDS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
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| US11/493,431 | 2006-07-25 |
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| US20070082940A1 (en) | 2005-07-27 | 2007-04-12 | Phil Skolnick | Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders |
| US20080045725A1 (en) * | 2006-04-28 | 2008-02-21 | Murry Jerry A | Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane |
| EP2016053B1 (en) * | 2006-04-28 | 2010-11-10 | Merck Sharp & Dohme Corp. | Process for the synthesis of (+) and (-)-1-aryl-3-azabicyclo[3.1.0]hexanes |
| US8138377B2 (en) | 2006-11-07 | 2012-03-20 | Dov Pharmaceutical, Inc. | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| US9133159B2 (en) | 2007-06-06 | 2015-09-15 | Neurovance, Inc. | 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| GB0716632D0 (en) * | 2007-08-24 | 2007-10-03 | Glaxo Group Ltd | Compounds |
| GB0716633D0 (en) * | 2007-08-24 | 2007-10-03 | Glaxo Group Ltd | Compounds |
| GB0804326D0 (en) * | 2008-03-07 | 2008-04-16 | Glaxo Group Ltd | Novel compounds |
| ES2421171T3 (es) * | 2008-12-16 | 2013-08-29 | Sunovion Pharmaceuticals Inc. | Inhibidores de reabsorción triples y su uso en métodos |
| CN102803224A (zh) | 2009-06-26 | 2012-11-28 | 万能药生物有限公司 | 新的氮杂双环己烷类化合物 |
| WO2012033956A1 (en) * | 2010-09-08 | 2012-03-15 | Mithridion, Inc. | Cognition enhancing compounds and compositions, methods of making, and methods of treating |
| US9133116B2 (en) | 2010-09-28 | 2015-09-15 | Panacea Biotec Ltd. | Bicyclic compounds |
| LT2819516T (lt) * | 2011-07-30 | 2020-05-25 | Otsuka America Pharmaceutical, Inc. | (1r,5s)-(+)-1-(naftalen-2-il)-3-azabiciklo{3.1.0} heksano naudojimas monoamino neurotransmiterių paveiktoms ligoms gydyti |
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| JP6284140B2 (ja) * | 2013-06-17 | 2018-02-28 | 株式会社タムラ製作所 | Ｇａ２Ｏ３系半導体素子 |
| AU2014374259A1 (en) * | 2013-12-09 | 2016-07-21 | Neurovance, Inc. | Novel compositions |
| HUE059348T2 (hu) | 2015-06-17 | 2022-11-28 | Otsuka America Pharmaceutical Inc | Kristályos vegyületek |
| WO2018119291A1 (en) * | 2016-12-21 | 2018-06-28 | Otsuka America Pharmaceutical, Inc. | Synthetic methods |
| WO2019208807A1 (ja) | 2018-04-26 | 2019-10-31 | 株式会社エーピーアイ コーポレーション | 芳香族ニトリル化合物の製造方法 |
| US12421246B2 (en) * | 2019-01-09 | 2025-09-23 | Eisai R&D Management Co., Ltd. | Method for synthesis of diazabicyclo[6.2.0]decane related compounds |
| KR20220083740A (ko) | 2019-10-16 | 2022-06-20 | 오츠카 세이야쿠 가부시키가이샤 | 센타나파딘의 제조 방법 |
| CN120842114A (zh) | 2019-10-29 | 2025-10-28 | 株式会社Api | 高纯度2-萘乙腈及其生产方法 |
| WO2022181625A1 (en) | 2021-02-23 | 2022-09-01 | Otsuka Pharmaceutical Co., Ltd. | Centanafadine pharmaceutical formulations, and methods of making and using same |
| US20240246914A1 (en) | 2021-05-31 | 2024-07-25 | Teva Pharmaceuticals International Gmbh | Solid state form of centanafadine hcl and process for preparation thereof |
| CN117480153A (zh) * | 2021-06-15 | 2024-01-30 | 大塚制药株式会社 | 氮杂双环[3.1.0]己烷化合物 |
| US20250375418A1 (en) | 2022-09-02 | 2025-12-11 | Otsuka Pharmaceutical Co., Ltd. | 1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane for treating major depressive disorder |
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2006
- 2006-07-25 US US11/493,431 patent/US20070082940A1/en not_active Abandoned
- 2006-07-25 CN CN201410309301.2A patent/CN104059013B8/zh active Active
- 2006-07-25 BR BRPI0613943-4A patent/BRPI0613943B1/pt active IP Right Grant
- 2006-07-25 KR KR1020147018408A patent/KR101733180B1/ko not_active Expired - Fee Related
- 2006-07-25 AU AU2006275870A patent/AU2006275870B2/en active Active
- 2006-07-25 RU RU2008107336/04A patent/RU2008107336A/ru not_active Application Discontinuation
- 2006-07-25 JP JP2008524100A patent/JP5184354B2/ja active Active
- 2006-07-25 EP EP06788541A patent/EP1915146A4/en not_active Withdrawn
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