CA2659215C - Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders - Google Patents

Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders Download PDF

Info

Publication number
CA2659215C
CA2659215C CA2659215A CA2659215A CA2659215C CA 2659215 C CA2659215 C CA 2659215C CA 2659215 A CA2659215 A CA 2659215A CA 2659215 A CA2659215 A CA 2659215A CA 2659215 C CA2659215 C CA 2659215C
Authority
CA
Canada
Prior art keywords
hexane
aza
bicyclo
compound
naphthalen
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.)
Active
Application number
CA2659215A
Other languages
English (en)
French (fr)
Other versions
CA2659215A1 (en
Inventor
Phil Skolnick
Zhengming Chen
Anthony Basile
Joseph W. Epstein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Otsuka America Pharmaceutical Inc
Original Assignee
Otsuka America Pharmaceutical Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Otsuka America Pharmaceutical Inc filed Critical Otsuka America Pharmaceutical Inc
Publication of CA2659215A1 publication Critical patent/CA2659215A1/en
Application granted granted Critical
Publication of CA2659215C publication Critical patent/CA2659215C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/33—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/34—Tobacco-abuse
    • 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
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • C—CHEMISTRY; METALLURGY
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Epidemiology (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Anesthesiology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Pyrrole Compounds (AREA)
CA2659215A 2005-07-27 2006-07-25 Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders Active CA2659215C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US70336405P 2005-07-27 2005-07-27
US60/703,364 2005-07-27
US11/493,431 US20070082940A1 (en) 2005-07-27 2006-07-25 Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
PCT/US2006/029006 WO2007016155A2 (en) 2005-07-27 2006-07-25 Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US11/493,431 2006-07-25

Publications (2)

Publication Number Publication Date
CA2659215A1 CA2659215A1 (en) 2007-02-08
CA2659215C true CA2659215C (en) 2018-07-10

Family

ID=37709141

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2659215A Active CA2659215C (en) 2005-07-27 2006-07-25 Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders

Country Status (16)

Country Link
US (9) US20070082940A1 (enExample)
EP (2) EP1915146A4 (enExample)
JP (3) JP5184354B2 (enExample)
KR (3) KR101733180B1 (enExample)
CN (2) CN101272781A (enExample)
AU (1) AU2006275870B2 (enExample)
BR (1) BRPI0613943B1 (enExample)
CA (1) CA2659215C (enExample)
CY (1) CY1122238T1 (enExample)
IL (2) IL189008A (enExample)
NO (1) NO343037B1 (enExample)
NZ (1) NZ592836A (enExample)
PL (1) PL2719384T3 (enExample)
RU (1) RU2008107336A (enExample)
WO (1) WO2007016155A2 (enExample)
ZA (1) ZA200801825B (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070043100A1 (en) 2005-08-16 2007-02-22 Hagen Eric J Novel polymorphs of azabicyclohexane
CN101272781A (zh) 2005-07-27 2008-09-24 多夫药品公司 新的1-芳基-3-氮杂二环[3.1.0]己烷：其制备方法和用于治疗神经精神障碍的用途
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
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
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
WO2010075064A1 (en) * 2008-12-16 2010-07-01 Sepracor Inc. Triple reuptake inhibitors and methods of their use
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
WO2012042539A2 (en) 2010-09-28 2012-04-05 Panacea Biotec Ltd Novel bicyclic compounds
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
HRP20200424T1 (hr) * 2011-07-30 2020-09-04 Otsuka America Pharmaceutical, Inc. Uporaba (1r,5s)-(+)-1-(naftalen-2-il)-3-azabiciklo(3.1.0)heksana u liječenju uvjeta koji su pod utjecajem monoaminskih neurotransmitera
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
US20160303077A1 (en) * 2013-12-09 2016-10-20 Neurovance, Inc. Novel compositions
CN107921021A (zh) 2015-06-17 2018-04-17 大塚制药美国公司 结晶化合物
WO2018119291A1 (en) * 2016-12-21 2018-06-28 Otsuka America Pharmaceutical, Inc. Synthetic methods
US12054448B2 (en) 2018-04-26 2024-08-06 Api Corporation Method for manufacturing aromatic nitrile compound
CN113661166A (zh) * 2019-01-09 2021-11-16 卫材R&D管理有限公司 用于合成二氮杂二环[6.2.0]癸烷相关化合物的方法
WO2021075494A1 (ja) 2019-10-16 2021-04-22 大塚製薬株式会社 センタナファジンの製造方法
WO2021085468A1 (ja) 2019-10-29 2021-05-06 株式会社エーピーアイ コーポレーション 高純度２－ナフチルアセトニトリル及びその製造方法
JP7787190B2 (ja) 2021-02-23 2025-12-16 大塚製薬株式会社 センタナファジン製剤ならびにその製造および使用方法
WO2022256215A1 (en) 2021-05-31 2022-12-08 Teva Pharmaceuticals International Gmbh Solid state form of centanafadine hcl and process for preparation thereof
EP4357335A4 (en) * 2021-06-15 2025-11-26 Otsuka Pharma Co Ltd AZABICYCLO[3.1.0]HEXANE COMPOUND
CA3264158A1 (en) 2022-09-02 2024-03-07 Otsuka Pharmaceutical Co., Ltd. 1-(NAPHTALENE-2-YL)-3-AZABICYCLO[3.1.0]HEXANE FOR THE TREATMENT OF MAJOR DEPRESSIVE DISORDER

Family Cites Families (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA974518A (en) 1972-04-20 1975-09-16 Merz And Co. Procedure for the manufacture of 1,3,5 trisubstituted adamantan compounds
CS175641B1 (en) * 1973-06-14 1977-05-31 Boris D Babickij Making method of 2-alkyl-1,3-butadiene's 1,4-transpolymers and/or 2-alkyl-1,3-butadiene's stereoregular 1,4 trans-copolymers with 1,3-butadiene
JPS535994B2 (enExample) * 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
US4088652A (en) * 1975-07-31 1978-05-09 American Cyanamid Company Acylazabicyclohexanes
US4131611A (en) * 1975-07-31 1978-12-26 American Cyanamid Company Azabicyclohexanes
US4231935A (en) * 1975-07-31 1980-11-04 American Cyanamid Company 1-Phenyl-3-azabicyclo[3.1.0]hexanes
GB1532682A (en) * 1976-04-27 1978-11-22 Bristol Myers Co Process for the preparation of cephadroxil
US4118393A (en) * 1977-06-23 1978-10-03 American Cyanamid Company Phenyl azabicyclohexanones
US4118417A (en) * 1977-06-23 1978-10-03 American Cyanamid Company Process for resolving cis-1-substituted phenyl-1,2-cyclopropanedicarboxylic acids
GR72713B (enExample) 1976-09-15 1983-12-01 American Cyanamid Co
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
PL120095B2 (en) 1977-10-04 1982-02-27 Univ Lodzki Process for preparing novel derivatives of 1,3,3a,6,7,7a-hexahydrodibenzo-/4,5:8,9/-3a,6-ethenisoindolesagidrodibenzo 4,5:8,9-3a,6-ehtenoizoinidola
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
US4431661A (en) 1981-08-20 1984-02-14 American Cyanamid Company 5-Aryl-3-azabicyclo[3.2.0]heptan-6-one acetals, and analgesic use therefor
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
EP0100426A1 (en) 1982-07-28 1984-02-15 American Cyanamid Company 3a-(substituted-phenyl)-hexaloctahydro-4,7-alkanoisoindoles
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
US5316759A (en) * 1986-03-17 1994-05-31 Robert J. Schaap Agonist-antagonist combination to reduce the use of nicotine and other drugs
US5198459A (en) * 1987-07-11 1993-03-30 Sandoz Ltd. Use of 5HT-3 antagonists in preventing or reducing dependency on dependency-inducing agents
DE3822792C2 (de) * 1987-07-11 1997-11-27 Sandoz Ag Neue Verwendung von 5HT¶3¶-Antagonisten
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
US5204366A (en) 1991-06-10 1993-04-20 American Cyanamid Company 2,5-dioxo-3-pyrroline-1-acetanilide fungicidal agents, compositions and method for use thereof
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
ES2167587T3 (es) * 1995-07-17 2002-05-16 Warner Lambert Co Forma cristalina de la sal hemicalcica del acido (r-(r*,r*))-2-(4-fluorofenil)-beta,delta-dihidroxi-5-(1-metiletil)-3-fenil-4-((fenilamino)carbonil)-1h-pirrol-1-heptanoico (atorvastatina).
AUPN605795A0 (en) * 1995-10-19 1995-11-09 F.H. Faulding & Co. Limited Analgesic pharmaceutical composition
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
US5905154A (en) 1996-06-10 1999-05-18 American Cyanamid Company Process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds
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
EP1048653B1 (en) * 1997-12-05 2004-03-03 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
US6132724A (en) 1998-04-29 2000-10-17 City Of Hope National Medical Center Allelic polygene diagnosis of reward deficiency syndrome and treatment
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
MXPA04005503A (es) 2001-12-04 2004-12-06 Schering Corp Derivados de n-aril-n??arilcicloalquilurea como antagonistas de la hormona concentradora de melanina para el tratamiento de la obesidad.
US20030187026A1 (en) 2001-12-13 2003-10-02 Qun Li Kinase inhibitors
WO2003068211A1 (en) 2002-02-12 2003-08-21 Cypress Bioscience, Inc. Methods of treating attention deficit/hyperactivity disorder (adhd)
US20040127541A1 (en) * 2002-07-31 2004-07-01 Janet Codd Bicifadine formulation
US7094799B2 (en) * 2002-11-08 2006-08-22 Dov Pharmaceutical, Inc. Polymorphs of bicifadine hydrochloride
FR2859208B1 (fr) 2003-09-02 2006-01-21 Servier Lab Nouveaux derives de 9-amino-podophyllotoxine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
HRP20100114T1 (hr) * 2004-02-23 2010-04-30 Glaxo Group Limited Derivati azabiciklo[3.1.0]heksana korisni kao modulatori dopaminskih receptora d3
ZA200701570B (en) 2004-08-18 2008-08-27 Dov Pharmaceutical Inc Novel polymorphs of azabicyclohexane
CA2640120A1 (en) * 2005-03-08 2006-09-14 Dov Pharmaceutical, Inc. 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
GB0507680D0 (en) * 2005-04-15 2005-05-25 Glaxo Group Ltd Compounds
WO2007013936A2 (en) * 2005-07-21 2007-02-01 Wyeth Method for treating nervous system disorders and conditions
US20070082939A1 (en) * 2005-07-26 2007-04-12 Lippa Arnold S Methods and compositions for the treatment of neuropathies and related disorders
CN101272781A (zh) 2005-07-27 2008-09-24 多夫药品公司 新的1-芳基-3-氮杂二环[3.1.0]己烷：其制备方法和用于治疗神经精神障碍的用途
GB0517191D0 (en) 2005-08-22 2005-09-28 Glaxo Group Ltd Compounds
GB0517175D0 (en) * 2005-08-22 2005-09-28 Glaxo Group Ltd Compounds
JP5237807B2 (ja) * 2005-08-22 2013-07-17 グラクソ グループ リミテッド ドーパミンｄ３受容体の調節因子としてのトリアゾール誘導体
GB0517193D0 (en) * 2005-08-22 2005-09-28 Glaxo Group Ltd Novel use
WO2007025144A1 (en) 2005-08-24 2007-03-01 University Of Illinois - Chicago 5-ht2c receptor agonists as anorectic agents
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
US20080058535A1 (en) 2006-07-25 2008-03-06 Zhengming Chen Methods and compositions for production, formulation and use of 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
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
KR100837555B1 (ko) * 2006-11-24 2008-06-12 동부일렉트로닉스 주식회사 반도체 소자 및 그 제조 방법
WO2008153937A2 (en) 2007-06-06 2008-12-18 Dov Pharmaceutical, Inc. Novel 1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
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
HRP20200424T1 (hr) 2011-07-30 2020-09-04 Otsuka America Pharmaceutical, Inc. Uporaba (1r,5s)-(+)-1-(naftalen-2-il)-3-azabiciklo(3.1.0)heksana u liječenju uvjeta koji su pod utjecajem monoaminskih neurotransmitera
US20140228421A1 (en) 2011-09-07 2014-08-14 Anthony McKinney Methods For Inhibiting Native And Promiscuous Uptake Of Monoamine Neurotransmitters
WO2014058742A1 (en) 2012-10-09 2014-04-17 Sears Douglas Therapeutic treatment
US20160303077A1 (en) 2013-12-09 2016-10-20 Neurovance, Inc. Novel compositions
CN107921021A (zh) 2015-06-17 2018-04-17 大塚制药美国公司 结晶化合物

Also Published As

Publication number Publication date
BRPI0613943A2 (pt) 2011-02-22
AU2006275870B2 (en) 2013-01-10
CY1122238T1 (el) 2020-07-31
IL189008A0 (en) 2008-11-03
US8877798B2 (en) 2014-11-04
US9737506B2 (en) 2017-08-22
NO20081016L (no) 2008-04-18
US20180000777A1 (en) 2018-01-04
JP2015134786A (ja) 2015-07-27
CA2659215A1 (en) 2007-02-08
KR101733180B1 (ko) 2017-05-08
RU2008107336A (ru) 2009-09-10
KR20080042098A (ko) 2008-05-14
JP5184354B2 (ja) 2013-04-17
NZ592836A (en) 2013-01-25
BRPI0613943B1 (pt) 2021-06-22
EP2719384A1 (en) 2014-04-16
WO2007016155A3 (en) 2007-11-15
US8461196B2 (en) 2013-06-11
US10039746B2 (en) 2018-08-07
CN101272781A (zh) 2008-09-24
US20210023049A1 (en) 2021-01-28
JP5767178B2 (ja) 2015-08-19
US20130345439A1 (en) 2013-12-26
EP2719384B1 (en) 2018-08-08
US20150148399A1 (en) 2015-05-28
US20070082940A1 (en) 2007-04-12
ZA200801825B (en) 2009-12-30
US20190070148A1 (en) 2019-03-07
US20090233978A1 (en) 2009-09-17
AU2006275870A1 (en) 2007-02-08
EP1915146A4 (en) 2010-06-02
WO2007016155A2 (en) 2007-02-08
CN104059013B (zh) 2016-06-22
CN104059013B8 (zh) 2016-09-21
US20120302619A1 (en) 2012-11-29
KR20140093750A (ko) 2014-07-28
EP1915146A2 (en) 2008-04-30
US20160158197A1 (en) 2016-06-09
US9205074B2 (en) 2015-12-08
CN104059013A (zh) 2014-09-24
KR101465178B1 (ko) 2014-12-02
NO343037B1 (no) 2018-10-08
KR20170005888A (ko) 2017-01-16
IL245489A0 (en) 2016-06-30
IL189008A (en) 2017-04-30
JP2013035842A (ja) 2013-02-21
PL2719384T3 (pl) 2019-02-28
JP2009502939A (ja) 2009-01-29

Similar Documents

Publication Publication Date Title
CA2659215C (en) Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
EP2167083B1 (en) 1- heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments
US20060223875A1 (en) Methods and compositions for production, formulation and use of 1-aryl-3-azabicyclo[3.1.0]hexanes
EP2077837A2 (fr) Derives de pyrrolizine, indolizine et quinolizine, leur preparation et leur application en therapeutique.
DK2719384T3 (en) Novel preparations with 1-naphthyl-3-azabicyclo [3.1.0] hexanes and use in the treatment of neuropsychiatric disorders.
HK1196940A (en) Novel 1-naphthyl-3-azabicyclo[3.1.0]hexanes:preparation and use to treat neuropsychiatric disorders
HK1196940B (en) Novel 1-naphthyl-3-azabicyclo[3.1.0]hexanes:preparation and use to treat neuropsychiatric disorders
MX2008001187A (en) Novel 1-aryl-3-azabicyclo[3.1.0]hexanes:preparation and use to treat neuropsychiatric disorders
HK1122215A (en) Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders

Legal Events

Date Code Title Description
EEER Examination request