RU2009121553A - Новые арилбицикло[3.1.0]гексиламины и способы и композиции для их получения и применения - Google Patents
Новые арилбицикло[3.1.0]гексиламины и способы и композиции для их получения и применения Download PDFInfo
- Publication number
- RU2009121553A RU2009121553A RU2009121553/04A RU2009121553A RU2009121553A RU 2009121553 A RU2009121553 A RU 2009121553A RU 2009121553/04 A RU2009121553/04 A RU 2009121553/04A RU 2009121553 A RU2009121553 A RU 2009121553A RU 2009121553 A RU2009121553 A RU 2009121553A
- Authority
- RU
- Russia
- Prior art keywords
- amine
- hexane
- bicyclo
- hexan
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims 29
- 239000000203 mixture Substances 0.000 title claims 13
- 150000001875 compounds Chemical class 0.000 claims abstract 72
- 125000000217 alkyl group Chemical group 0.000 claims abstract 64
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 50
- 150000002367 halogens Chemical class 0.000 claims abstract 29
- WGBBUURBHXLGFM-UHFFFAOYSA-N hexan-2-amine Chemical compound CCCCC(C)N WGBBUURBHXLGFM-UHFFFAOYSA-N 0.000 claims abstract 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract 27
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 26
- 125000001424 substituent group Chemical group 0.000 claims abstract 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 239000001257 hydrogen Substances 0.000 claims abstract 20
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 18
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 18
- 125000003118 aryl group Chemical group 0.000 claims abstract 18
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 18
- 125000005843 halogen group Chemical group 0.000 claims abstract 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 17
- 239000000651 prodrug Substances 0.000 claims abstract 16
- 229940002612 prodrug Drugs 0.000 claims abstract 16
- 239000012453 solvate Substances 0.000 claims abstract 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract 12
- 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 11
- 150000004677 hydrates Chemical class 0.000 claims abstract 11
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract 9
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 2
- HQLZFBUAULNEGP-UHFFFAOYSA-N hexan-3-amine Chemical compound CCCC(N)CC HQLZFBUAULNEGP-UHFFFAOYSA-N 0.000 claims 18
- 238000007363 ring formation reaction Methods 0.000 claims 16
- 208000015114 central nervous system disease Diseases 0.000 claims 14
- -1 chloro, bromo, iodo Chemical group 0.000 claims 13
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 12
- 210000004027 cell Anatomy 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 11
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 10
- 239000003937 drug carrier Substances 0.000 claims 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 10
- 150000001412 amines Chemical class 0.000 claims 8
- BOPSAQVEGQKJPU-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-3-amine Chemical compound C1C(N)CC2CC21C1=CC=C(Cl)C(Cl)=C1 BOPSAQVEGQKJPU-UHFFFAOYSA-N 0.000 claims 7
- 210000003169 central nervous system Anatomy 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 230000007062 hydrolysis Effects 0.000 claims 7
- 238000006460 hydrolysis reaction Methods 0.000 claims 7
- CYWNXJDAHXCTDY-UHFFFAOYSA-N n,n-dimethyl-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C(C34CC3CC(C4)N(C)C)=CC=CC2=C1 CYWNXJDAHXCTDY-UHFFFAOYSA-N 0.000 claims 7
- BJHKEGAQSFMVQE-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C(C34CC3CC(C4)NC)=CC=CC2=C1 BJHKEGAQSFMVQE-UHFFFAOYSA-N 0.000 claims 7
- GTAVXMAPXFMUMZ-UHFFFAOYSA-N n-methyl-1-naphthalen-2-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=CC2=CC(C34CC3CC(C4)NC)=CC=C21 GTAVXMAPXFMUMZ-UHFFFAOYSA-N 0.000 claims 7
- 238000006268 reductive amination reaction Methods 0.000 claims 7
- JZLBUIIHIYKZQA-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n,n-dimethylbicyclo[3.1.0]hexan-2-amine Chemical compound CN(C)C1CCC2CC12C1=CC=C(Cl)C(Cl)=C1 JZLBUIIHIYKZQA-UHFFFAOYSA-N 0.000 claims 6
- WAEQWTAGGVBEBY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methylbicyclo[3.1.0]hexan-2-amine Chemical compound CNC1CCC2CC12C1=CC=C(Cl)C(Cl)=C1 WAEQWTAGGVBEBY-UHFFFAOYSA-N 0.000 claims 6
- MIOACJKLZCNKBE-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methylbicyclo[3.1.0]hexan-3-amine Chemical compound C1C(NC)CC2CC21C1=CC=C(Cl)C(Cl)=C1 MIOACJKLZCNKBE-UHFFFAOYSA-N 0.000 claims 6
- AKSYYBWFPSRFMM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-2-amine Chemical compound NC1CCC2CC12C1=CC=C(Cl)C(Cl)=C1 AKSYYBWFPSRFMM-UHFFFAOYSA-N 0.000 claims 6
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 5
- XIBILYUXEMBUGY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n,n-dimethylbicyclo[3.1.0]hexan-3-amine Chemical compound C1C(N(C)C)CC2CC21C1=CC=C(Cl)C(Cl)=C1 XIBILYUXEMBUGY-UHFFFAOYSA-N 0.000 claims 5
- ZALDYBSAVFVVJR-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n,n-dimethylbicyclo[3.1.0]hexan-4-amine Chemical compound C1C2C(N(C)C)CCC21C1=CC=C(Cl)C(Cl)=C1 ZALDYBSAVFVVJR-UHFFFAOYSA-N 0.000 claims 5
- DKBYLKRWTWSWJM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-4-amine Chemical compound C1C2C(N)CCC21C1=CC=C(Cl)C(Cl)=C1 DKBYLKRWTWSWJM-UHFFFAOYSA-N 0.000 claims 5
- 230000000035 biogenic effect Effects 0.000 claims 5
- 229960003638 dopamine Drugs 0.000 claims 5
- BWDGXSGYSZASAX-UHFFFAOYSA-N n,n-dimethyl-1-naphthalen-1-ylbicyclo[3.1.0]hexan-4-amine Chemical compound C1=CC=C2C(C34CCC(C3C4)N(C)C)=CC=CC2=C1 BWDGXSGYSZASAX-UHFFFAOYSA-N 0.000 claims 5
- MLMLDKRMIBVOFY-UHFFFAOYSA-N n,n-dimethyl-1-naphthalen-2-ylbicyclo[3.1.0]hexan-4-amine Chemical compound C1=CC=CC2=CC(C34CCC(C3C4)N(C)C)=CC=C21 MLMLDKRMIBVOFY-UHFFFAOYSA-N 0.000 claims 5
- NOHMVCZNSGEVCK-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylbicyclo[3.1.0]hexan-4-amine Chemical compound C1=CC=C2C(C34CCC(C3C4)NC)=CC=CC2=C1 NOHMVCZNSGEVCK-UHFFFAOYSA-N 0.000 claims 5
- GPDDOMZRRYENNX-UHFFFAOYSA-N n-methyl-1-naphthalen-2-ylbicyclo[3.1.0]hexan-4-amine Chemical compound C1=CC=CC2=CC(C34CCC(C3C4)NC)=CC=C21 GPDDOMZRRYENNX-UHFFFAOYSA-N 0.000 claims 5
- 239000002858 neurotransmitter agent Substances 0.000 claims 5
- 229960002748 norepinephrine Drugs 0.000 claims 5
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 229940076279 serotonin Drugs 0.000 claims 5
- BOPSAQVEGQKJPU-SBMIAAHKSA-N (1r,3r,5r)-1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-3-amine Chemical compound C1([C@@]23C[C@@H]2C[C@H](C3)N)=CC=C(Cl)C(Cl)=C1 BOPSAQVEGQKJPU-SBMIAAHKSA-N 0.000 claims 4
- QOERHOWUEYOSMZ-WOSRLPQWSA-N (1r,3r,5r)-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C([C@@]34C[C@@H]3C[C@H](C4)N)=CC=CC2=C1 QOERHOWUEYOSMZ-WOSRLPQWSA-N 0.000 claims 4
- BOPSAQVEGQKJPU-AUTRQRHGSA-N (1r,3s,5r)-1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-3-amine Chemical compound C1([C@@]23C[C@@H]2C[C@@H](C3)N)=CC=C(Cl)C(Cl)=C1 BOPSAQVEGQKJPU-AUTRQRHGSA-N 0.000 claims 4
- QOERHOWUEYOSMZ-HEHGZKQESA-N (1r,3s,5r)-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C([C@@]34C[C@@H]3C[C@@H](C4)N)=CC=CC2=C1 QOERHOWUEYOSMZ-HEHGZKQESA-N 0.000 claims 4
- BOPSAQVEGQKJPU-OYGLUPDLSA-N (1r,5r)-1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-3-amine Chemical compound C1([C@@]23C[C@@H]2CC(C3)N)=CC=C(Cl)C(Cl)=C1 BOPSAQVEGQKJPU-OYGLUPDLSA-N 0.000 claims 4
- QOERHOWUEYOSMZ-GMRULEOSSA-N (1r,5r)-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C([C@@]34C[C@@H]3CC(C4)N)=CC=CC2=C1 QOERHOWUEYOSMZ-GMRULEOSSA-N 0.000 claims 4
- BOPSAQVEGQKJPU-YKXYSFTHSA-N (1s,5s)-1-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-3-amine Chemical compound C1([C@]23C[C@H]2CC(C3)N)=CC=C(Cl)C(Cl)=C1 BOPSAQVEGQKJPU-YKXYSFTHSA-N 0.000 claims 4
- QOERHOWUEYOSMZ-LRRQEPCHSA-N (1s,5s)-1-naphthalen-1-ylbicyclo[3.1.0]hexan-3-amine Chemical compound C1=CC=C2C([C@]34C[C@H]3CC(C4)N)=CC=CC2=C1 QOERHOWUEYOSMZ-LRRQEPCHSA-N 0.000 claims 4
- VRJQNBKWKVEZJL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methylbicyclo[3.1.0]hexan-4-amine Chemical compound C1C2C(NC)CCC21C1=CC=C(Cl)C(Cl)=C1 VRJQNBKWKVEZJL-UHFFFAOYSA-N 0.000 claims 4
- 238000005888 cyclopropanation reaction Methods 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 238000010521 absorption reaction Methods 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 230000006735 deficit Effects 0.000 claims 3
- 230000002140 halogenating effect Effects 0.000 claims 3
- 230000026030 halogenation Effects 0.000 claims 3
- 238000005658 halogenation reaction Methods 0.000 claims 3
- 210000004962 mammalian cell Anatomy 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims 2
- DTWCFCILAJVNPE-UHFFFAOYSA-N 3-methoxycyclopent-2-en-1-one Chemical compound COC1=CC(=O)CC1 DTWCFCILAJVNPE-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- WLHFJOAMEJUDNC-UHFFFAOYSA-N n-methylbicyclo[3.1.0]hexan-2-amine Chemical compound CNC1CCC2CC12 WLHFJOAMEJUDNC-UHFFFAOYSA-N 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/01—Hydrocarbons
- A61K31/015—Hydrocarbons carbocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85766706P | 2006-11-07 | 2006-11-07 | |
| US60/857,667 | 2006-11-07 | ||
| US11/936,016 US8138377B2 (en) | 2006-11-07 | 2007-11-06 | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| US11/936,016 | 2007-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009121553A true RU2009121553A (ru) | 2011-01-27 |
Family
ID=39365134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009121553/04A RU2009121553A (ru) | 2006-11-07 | 2007-11-07 | Новые арилбицикло[3.1.0]гексиламины и способы и композиции для их получения и применения |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8138377B2 (https=) |
| EP (1) | EP2086328A4 (https=) |
| JP (1) | JP2010509334A (https=) |
| KR (1) | KR20090079984A (https=) |
| BR (1) | BRPI0718654A2 (https=) |
| CA (1) | CA2705457A1 (https=) |
| RU (1) | RU2009121553A (https=) |
| WO (1) | WO2008057575A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070043100A1 (en) | 2005-08-16 | 2007-02-22 | Hagen Eric J | Novel polymorphs of azabicyclohexane |
| NZ592836A (en) | 2005-07-27 | 2013-01-25 | Dov Pharmaceutical Inc | 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 |
| US20080269348A1 (en) * | 2006-11-07 | 2008-10-30 | Phil Skolnick | Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use |
| US20090069374A1 (en) * | 2007-06-06 | 2009-03-12 | Phil Skolnick | Novel 1-Heteroaryl-3-Azabicyclo[3.1.0]Hexanes, Methods For Their Preparation And Their Use As Medicaments |
| 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 |
| BR112012000657A2 (pt) | 2009-06-26 | 2016-11-16 | Panacea Biotec Ltd | novos azabicilohexanos |
| US20140206740A1 (en) | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| JP6147279B2 (ja) | 2012-02-17 | 2017-06-14 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | オレキシン−２受容体アンタゴニストの合成において有用な方法および化合物 |
| WO2026069004A1 (en) * | 2024-09-27 | 2026-04-02 | Brandaris Therapeutics B.V. | Aminocyclohexenyl-6,6-bicyclic 5-ht2ar agonists and uses thereof |
Family Cites Families (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE800903A (fr) | 1973-06-14 | 1973-12-14 | Babitsky Boris D | Procede d'obtention de polymeres d'alcoyl-2 butadienes-1,3 ou de copolymeres d'alcoyl-2 butadienes-1,3-butadiene-1,3 |
| JPS535994B2 (https=) | 1974-09-26 | 1978-03-03 | ||
| US4196120A (en) | 1975-07-31 | 1980-04-01 | American Cyanamid Company | Azabicyclohexanes, method of use and preparation of the same |
| US4231935A (en) | 1975-07-31 | 1980-11-04 | American Cyanamid Company | 1-Phenyl-3-azabicyclo[3.1.0]hexanes |
| US4131611A (en) | 1975-07-31 | 1978-12-26 | American Cyanamid Company | Azabicyclohexanes |
| US4088652A (en) | 1975-07-31 | 1978-05-09 | American Cyanamid Company | Acylazabicyclohexanes |
| GB1532682A (en) | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
| GR72713B (https=) | 1976-09-15 | 1983-12-01 | American Cyanamid Co | |
| US4118417A (en) | 1977-06-23 | 1978-10-03 | American Cyanamid Company | Process for resolving cis-1-substituted phenyl-1,2-cyclopropanedicarboxylic acids |
| US4118393A (en) | 1977-06-23 | 1978-10-03 | American Cyanamid Company | Phenyl azabicyclohexanones |
| IL65843A (en) | 1977-08-11 | 1986-12-31 | American Cyanamid Co | Pharmaceutical compositions for the treatment of depression containing 3-aza-bicyclo(3.1.0)hexane derivatives and certain novel compounds of this type |
| CH644580A5 (de) | 1980-01-29 | 1984-08-15 | Hoffmann La Roche | Cyclohexen-derivate. |
| IL63968A (en) | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US4435419A (en) | 1981-07-01 | 1984-03-06 | American Cyanamid Company | Method of treating depression using azabicyclohexanes |
| JPS58150526A (ja) | 1982-03-04 | 1983-09-07 | Ube Ind Ltd | 光学活性プロパルギルアルコ−ル類およびその製法 |
| DE3324263A1 (de) | 1983-07-06 | 1985-01-17 | Hoechst Ag, 6230 Frankfurt | Derivate der 2-azabicyclo(3.1.0)hexan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie 2-azabicyclo(3.1.0)hexan-derivate als zwischenprodukte und verfahren zu deren herstellung |
| US4521131A (en) * | 1984-05-14 | 1985-06-04 | Shell Offshore Inc. | Lightweight semi-flexible dike |
| US5316759A (en) | 1986-03-17 | 1994-05-31 | Robert J. Schaap | Agonist-antagonist combination to reduce the use of nicotine and other drugs |
| DE3822792C2 (de) | 1987-07-11 | 1997-11-27 | Sandoz Ag | Neue Verwendung von 5HT¶3¶-Antagonisten |
| US5198459A (en) | 1987-07-11 | 1993-03-30 | Sandoz Ltd. | Use of 5HT-3 antagonists in preventing or reducing dependency on dependency-inducing agents |
| US5075341A (en) | 1989-12-01 | 1991-12-24 | The Mclean Hospital Corporation | Treatment for cocaine abuse |
| US5130430A (en) | 1990-10-31 | 1992-07-14 | Neurogen Corporation | 2-substituted imidazoquinoxaline diones, a new class of gaba brain receptor ligands |
| US6204284B1 (en) | 1991-12-20 | 2001-03-20 | American Cyanamid Company | Use of 1-(substitutedphenyl)-3-azabicyclo[3.1.0]hexanes for the treatment of chemical dependencies |
| US5478577A (en) | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
| US5232934A (en) | 1992-07-17 | 1993-08-03 | Warner-Lambert Co. | Method for the treatment of psychomotor stimulant addiction |
| US5321012A (en) | 1993-01-28 | 1994-06-14 | Virginia Commonwealth University Medical College | Inhibiting the development of tolerance to and/or dependence on a narcotic addictive substance |
| US5556837A (en) | 1994-08-01 | 1996-09-17 | Regeneron Pharmaceuticals Inc. | Methods for treating addictive disorders |
| US5488056A (en) | 1994-10-31 | 1996-01-30 | Eli Lilly And Company | Method for treating anxiety |
| US5762925A (en) | 1994-11-03 | 1998-06-09 | Sagen; Jacqueline | Preventing opiate tolerance by cellular implantation |
| KR100389518B1 (ko) | 1995-07-17 | 2003-11-15 | 워너-램버트 캄파니 엘엘씨 | 결정질[r-(r*,r*)]-2-(4-플루오로페닐)-베타,델타-디히드록시-5-(1-메틸에틸)-3-페닐-4-[(페닐아미노)카르보닐]-1h-피롤-1-헵탄산헤미칼슘염(아토르바스타틴) |
| AUPN605795A0 (en) | 1995-10-19 | 1995-11-09 | F.H. Faulding & Co. Limited | Analgesic pharmaceutical composition |
| AU703093B2 (en) * | 1995-11-16 | 1999-03-18 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| ZA969485B (en) | 1995-11-16 | 1998-05-12 | Lilly Co Eli | Excitatory amino acid receptor antagonists. |
| TW513409B (en) | 1996-06-07 | 2002-12-11 | Eisai Co Ltd | Polymorphs of donepezil hydrochloride |
| ZA983930B (en) | 1997-05-14 | 1999-11-08 | Lilly Co Eli | Excitatory amino acid receptor modulators. |
| US5911992A (en) | 1997-06-12 | 1999-06-15 | A. Glenn Braswell | Method for controlling weight with hypericum perforatum and garcinia cambogia |
| US6121261A (en) | 1997-11-19 | 2000-09-19 | Merck & Co., Inc. | Method for treating attention deficit disorder |
| US6245911B1 (en) | 1997-12-05 | 2001-06-12 | Eisai Co., Ltd. | Donepezil polycrystals and process for producing the same |
| US6245357B1 (en) | 1998-03-06 | 2001-06-12 | Alza Corporation | Extended release dosage form |
| US6109269A (en) | 1999-04-30 | 2000-08-29 | Medtronic, Inc. | Method of treating addiction by brain infusion |
| US6372919B1 (en) | 2001-01-11 | 2002-04-16 | Dov Pharmaceutical, Inc. | (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as an anti-depressant agent |
| US6569887B2 (en) | 2001-08-24 | 2003-05-27 | Dov Pharmaceuticals Inc. | (−)-1-(3,4-Dichlorophenyl)-3-azabicyclo[3.1.0]hexane, compositions thereof, and uses as a dopamine-reuptake |
| ATE404190T1 (de) * | 2001-12-04 | 2008-08-15 | Schering Corp | N-aryl-n'-arylcycloalkyl-harnstoff als mch antagonisten zur behandlung von fettleibigkeit |
| US20040127541A1 (en) | 2002-07-31 | 2004-07-01 | Janet Codd | Bicifadine formulation |
| BRPI0314377B8 (pt) * | 2002-09-16 | 2021-05-25 | Sepracor Inc | composto, composição farmacêutica, tablete ou cápsula, uso de uma quantidade terapeuticamente eficaz, e, processo para preparar um composto |
| PL376604A1 (pl) | 2002-11-08 | 2006-01-09 | Dov Pharmaceuticals, Inc. | Polimorfy chlorowodorku bicifadyny |
| US7030113B2 (en) * | 2003-10-02 | 2006-04-18 | Schering Corporation | Aminobenzimidazoles as selective melanin concentrating hormone receptor antagonists for the treatment of obesity and related disorders |
| PE20051173A1 (es) | 2004-02-23 | 2006-02-14 | Glaxo Group Ltd | Compuestos azabiciclico (3.1.0) hexanos como moduladores de receptores de dopamina d3 |
| JP2008506705A (ja) * | 2004-07-16 | 2008-03-06 | シェーリング コーポレイション | 肥満および関連する障害の処置のための、選択的メラニン凝集ホルモンレセプターアンタゴニストとしての新規ヘテロシクリル |
| MX2007001827A (es) | 2004-08-18 | 2007-04-23 | Dov Pharmaceutical Inc | Nuevas sustancias polimorfas de azabiciclohexano. |
| US20060223875A1 (en) | 2005-03-08 | 2006-10-05 | Phil Skolnick | Methods and compositions for production, formulation and use of 1-aryl-3-azabicyclo[3.1.0]hexanes |
| GB0507602D0 (en) | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| NZ592836A (en) | 2005-07-27 | 2013-01-25 | Dov Pharmaceutical Inc | Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders |
| WO2007022933A1 (en) | 2005-08-22 | 2007-03-01 | Glaxo Group Limited | Triazole derivatives as modulators of dopamine d3 receptors |
| GB0517191D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
| GB0517193D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Novel use |
| US20080269348A1 (en) | 2006-11-07 | 2008-10-30 | Phil Skolnick | Novel Arylbicyclo[3.1.0]Hexylamines And Methods And Compositions For Their Preparation And Use |
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- 2007-11-06 US US11/936,016 patent/US8138377B2/en not_active Expired - Fee Related
- 2007-11-07 KR KR1020097011844A patent/KR20090079984A/ko not_active Ceased
- 2007-11-07 RU RU2009121553/04A patent/RU2009121553A/ru not_active Application Discontinuation
- 2007-11-07 JP JP2009536293A patent/JP2010509334A/ja active Pending
- 2007-11-07 EP EP07861821A patent/EP2086328A4/en not_active Withdrawn
- 2007-11-07 WO PCT/US2007/023506 patent/WO2008057575A2/en not_active Ceased
- 2007-11-07 BR BRPI0718654-1A patent/BRPI0718654A2/pt not_active IP Right Cessation
- 2007-11-07 CA CA2705457A patent/CA2705457A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2705457A1 (en) | 2008-05-15 |
| JP2010509334A (ja) | 2010-03-25 |
| WO2008057575A2 (en) | 2008-05-15 |
| BRPI0718654A2 (pt) | 2013-11-19 |
| US8138377B2 (en) | 2012-03-20 |
| US20080293822A1 (en) | 2008-11-27 |
| EP2086328A2 (en) | 2009-08-12 |
| KR20090079984A (ko) | 2009-07-22 |
| WO2008057575A3 (en) | 2008-07-03 |
| EP2086328A4 (en) | 2011-03-16 |
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