CN102015591B - 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法 - Google Patents

制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法 Download PDF

Info

Publication number
CN102015591B
CN102015591B CN200980116092.7A CN200980116092A CN102015591B CN 102015591 B CN102015591 B CN 102015591B CN 200980116092 A CN200980116092 A CN 200980116092A CN 102015591 B CN102015591 B CN 102015591B
Authority
CN
China
Prior art keywords
chloro
phenyl
ethanol
propan
chlorophenyl
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.)
Expired - Fee Related
Application number
CN200980116092.7A
Other languages
English (en)
Chinese (zh)
Other versions
CN102015591A (zh
Inventor
马龙·V·卡洛斯
瑞安·O·卡斯特罗
陶菲克·加鲍伊
卢晓雄
马友安
尼古拉斯·D·桑马丁
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.)
Arena Pharmaceuticals Inc
Original Assignee
Arena Pharmaceuticals 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 Arena Pharmaceuticals Inc filed Critical Arena Pharmaceuticals Inc
Publication of CN102015591A publication Critical patent/CN102015591A/zh
Application granted granted Critical
Publication of CN102015591B publication Critical patent/CN102015591B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN200980116092.7A 2008-03-04 2009-03-03 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法 Expired - Fee Related CN102015591B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US6810208P 2008-03-04 2008-03-04
US61/068,102 2008-03-04
PCT/US2009/001340 WO2009111004A1 (en) 2008-03-04 2009-03-03 Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine

Publications (2)

Publication Number Publication Date
CN102015591A CN102015591A (zh) 2011-04-13
CN102015591B true CN102015591B (zh) 2014-01-29

Family

ID=40589739

Family Applications (1)

Application Number Title Priority Date Filing Date
CN200980116092.7A Expired - Fee Related CN102015591B (zh) 2008-03-04 2009-03-03 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2，3，4，5-四氢-1h-3-苯并氮杂卓相关的中间体的方法

Country Status (5)

Country Link
US (1) US8822727B2 (enExample)
EP (1) EP2288585A1 (enExample)
JP (1) JP5491421B2 (enExample)
CN (1) CN102015591B (enExample)
WO (1) WO2009111004A1 (enExample)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA05013364A (es) 2003-06-17 2006-03-17 Arena Pharm Inc Procedimiento para preparar 3-benzazepinas.
BRPI0515862A2 (pt) 2004-12-23 2011-10-11 Arena Pharm Inc uso de fentermina e agonista seletivo do receptor de 5ht-2c na preparação de composições, composições moduladoras do receptor de 5ht-2c e forma de dosagem unitária compreendendo as mesmas
JP5199997B2 (ja) 2006-04-03 2013-05-15 アリーナ ファーマシューティカルズ， インコーポレイテッド ８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス
US8822727B2 (en) 2008-03-04 2014-09-02 Arena Pharmaceuticals, Inc. Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
WO2010148207A2 (en) 2009-06-18 2010-12-23 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-ht2c receptor agonists
KR20130112848A (ko) 2010-06-02 2013-10-14 아레나 파마슈티칼스, 인크. 5-ｈｔ2ｃ 수용체 아고니스트의 제조 방법
KR20130138770A (ko) 2010-09-01 2013-12-19 아레나 파마슈티칼스, 인크. 광학적으로 활성 산을 갖는 로르카세린의 염
EP2611781A1 (en) 2010-09-01 2013-07-10 Arena Pharmaceuticals, Inc. Fast-dissolve dosage forms of 5-ht2c agonists
EP3485878A1 (en) 2010-09-01 2019-05-22 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-ht2c agonists useful for weight management
SG188361A1 (en) 2010-09-01 2013-04-30 Arena Pharm Inc Non-hygroscopic salts of 5-ht2c agonists
US20130267500A1 (en) 2010-09-01 2013-10-10 Arena Pharmaceuticals, Inc. 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level
US8999970B2 (en) 2010-09-01 2015-04-07 Arena Pharmaceuticals, Inc. Administration of an anti-obesity compound to individuals with renal impairment
CA2886875A1 (en) 2012-10-09 2014-04-17 Arena Pharmaceuticals, Inc. Method of weight management
WO2014187768A1 (en) 2013-05-20 2014-11-27 Lek Pharmaceuticals D.D. Novel synthetic processes to 8-chloro-3-benzo[d]azepine via friedel-crafts alkylation of olefin
CN105517994A (zh) 2013-06-21 2016-04-20 斯洛文尼亚莱柯制药股份有限公司 通过α-取代的苯乙烯类的不对称还原制备手性1-甲基-2，3，4，5-1H-苯并二氮杂*类
CN103901151A (zh) * 2014-04-23 2014-07-02 湖北朗昕生化药业有限公司 一种hplc法检测氯卡色林盐酸盐含量的方法
WO2015170346A1 (en) 2014-05-09 2015-11-12 Council Of Scientific & Industrial Research A process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-benzo[d]azepine its enantiomers
WO2016069875A1 (en) 2014-10-30 2016-05-06 Arena Pharmaceuticals, Inc. Compositions and methods for ceasing tobacco smoking
CN107673949B (zh) * 2017-10-25 2021-02-23 南京恒旺生物医药有限公司 一种1-氯-3-甲基-2-丁烯的制备方法
CN112358406A (zh) * 2020-10-28 2021-02-12 山东省药学科学院 一种氯卡色林中间体的制备方法
CN115784911A (zh) * 2022-10-19 2023-03-14 山东省药学科学院 一种1-[2-(4-氯苯基)-乙基氨基]-2-丙醇的合成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007120517A2 (en) * 2006-04-03 2007-10-25 Arena Pharmaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto

Family Cites Families (117)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2900415A (en) 1954-12-14 1959-08-18 Lakeside Lab Inc Synthesized antispasmodic compounds
CH481110A (de) 1967-02-17 1969-11-15 Geigy Ag J R Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen
CH498122A (de) 1968-02-09 1970-10-31 Geigy Ag J R Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates
CH500194A (de) 1968-02-15 1970-12-15 Ciba Geigy Ag Verfahren zur Herstellung von Tetrahydroazepinderivaten
US4233217A (en) 1968-03-11 1980-11-11 Pennwalt Corporation Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines
GB1268243A (en) 1968-03-11 1972-03-22 Wallace & Tiernan Inc 0,2,4,5,-tetrahydro-3h,3-benzazepines
FR314F (enExample) 1968-03-22 1970-05-25
FR7736M (enExample) 1968-09-02 1970-03-09
US3716639A (en) 1970-03-11 1973-02-13 Ciba Geigy Corp Anorexigenic tetrahydrobenzazepines
US3795683A (en) 1970-08-19 1974-03-05 Hoffmann La Roche 2,3,4,5-tetrahydro-1h-3-benzazepines
LU65954A1 (enExample) 1972-08-25 1974-03-07
US4210749A (en) 1974-11-12 1980-07-01 Pennwalt Corporation Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines
SE7510988L (sv) 1975-10-01 1977-04-02 Draco Ab Nya farmaceutiskt aktiva foreningar
US4111957A (en) 1977-02-02 1978-09-05 Smithkline Corporation Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds
US4108989A (en) 1977-04-01 1978-08-22 Smithkline Corporation 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones
DE2758001A1 (de) 1977-12-24 1979-07-12 Hoechst Ag Cephalosporinderivate und verfahren zu ihrer herstellung
CA1090797A (en) 1978-06-20 1980-12-02 Kenneth G. Holden Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1h- 3-benzazepine compounds
AU515236B2 (en) 1978-06-26 1981-03-26 Smithkline Corporation Substituted-1-thienyl and furyl-2,3,4,5-tetrahydro-14-3 benzazepine derivatives
ZA792785B (en) 1978-07-07 1980-08-27 Smithkline Corp Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines
IE50355B1 (en) 1979-10-20 1986-04-02 Wyeth John & Brother Ltd Morpholine derivatives
US4477378A (en) 1980-02-05 1984-10-16 Schering Corp. Esters of substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines
ZA827887B (en) 1981-11-27 1983-11-30 Smithkline Beckman Corp Pharmaceutical compositions and method of producing alpha2 antagonism
EP0080779B1 (en) 1981-11-27 1986-07-16 Smithkline Beckman Corporation 3-benzazepines as alpha-2 antagonists
FR2518544A1 (fr) 1981-12-22 1983-06-24 Lipha Benzodiazepines-1,3 thione-2, procede de preparation et medicament les contenant
FR2525603A1 (fr) 1982-04-27 1983-10-28 Adir Benzoazacycloalkyl-spiro-imidazolinines, leur preparation et leur application en therapeutique
US4988690A (en) 1982-06-14 1991-01-29 Hoechst-Roussel Pharmaceuticals Inc. 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof
DE3418270A1 (de) 1984-05-17 1985-11-21 Dr. Karl Thomae Gmbh, 7950 Biberach Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US4541954A (en) 1984-09-05 1985-09-17 Smithkline Beckman Corporation Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
EP0204349A3 (de) 1985-06-01 1990-01-03 Dr. Karl Thomae GmbH Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EG18188A (en) 1986-05-01 1992-09-30 Pfizer Ltd Process for preparation anti-arhythmia agents
US4762845A (en) 1986-05-21 1988-08-09 Abbott Laboratories 7-(3-Substituted imino-1-pyrrolidinyl)-quinolone-3-carboxylic acids
EP0285287A3 (en) 1987-03-23 1990-08-16 Smithkline Beecham Corporation 3-benzazepine compounds for use in treating gastrointestinal motility disorders
US5015639A (en) 1987-03-27 1991-05-14 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
US5247080A (en) 1987-03-27 1993-09-21 Schering Corporation Substituted benzazepines useful as intermediates for producing pharmaceutically active compounds
ZA882080B (en) 1987-03-27 1989-04-26 Schering Corp Substituted benzazepines,their preparation and pharmaceutical compositions containing them
AU1700688A (en) 1987-04-09 1988-11-04 Smithkline Beckman Corporation Sulfinyl and sulfonyl substituted 3-benzazepines
US4957914A (en) 1987-05-15 1990-09-18 Syntex (U.S.A.) Inc. 1,9-alkano-bridged-2,3,4,5-tetrahydro-1H-3-benzazepines
DK107688D0 (da) 1988-03-01 1988-03-01 Novo Industri As Carbaminsyreestere af substituerede 7-hydroxy-2,3,4,5-tetrahydro-1h-3-benzazepiner
US5422355A (en) 1989-06-02 1995-06-06 John Wyeth & Brother, Limited Composition for treating depression with (N-heteroaryl)alkylamines
US5178786A (en) 1989-08-04 1993-01-12 The Lubrizol Corporation Corrosion-inhibiting compositions and functional fluids containing same
CA2037162A1 (en) 1990-03-12 1991-09-13 Steven Howard Shaber Heterocyclicacetonitriles and fungicidal use
ZA914536B (en) 1990-06-15 1992-03-25 Schering Corp 8-lower alkyl-5-cycloalkyl or 5-cycloakenyl substituted benzazepines and pharmaceutical compositions containing them
JP2502723Y2 (ja) 1990-06-25 1996-06-26 油谷重工株式会社 建設機械のピン結合装置
US5275915A (en) 1991-06-05 1994-01-04 Dainippon Ink And Chemicals, Inc. Developer for light-sensitive material
CA2110575A1 (en) 1991-06-21 1993-01-07 John Gerard Ward Use of tetrahydrobenzazepine derivatives for the treatment of portal hypertension and migraine
GB9116824D0 (en) 1991-08-05 1991-09-18 Smithkline Beecham Corp Chemical compounds
EP0558824A1 (en) 1992-02-04 1993-09-08 Duphar International Research B.V Method for the preparation of vicinal aminoalcohols and optically active O-protected derivatives thereof
US5241065A (en) 1992-02-25 1993-08-31 Schering Corporation 2,3,4,5-tetrahydro-1h-3-benzazepines having anti-psychotic activity
US5218385A (en) * 1992-03-17 1993-06-08 Lii Jein Hei Flash light eyeglasses with hinge switch
EP0615166B1 (en) * 1993-02-26 1998-09-23 Mitsui Chemicals, Inc. Resins for electrophotographic toners
US6087346A (en) 1993-06-23 2000-07-11 Cambridge Neuroscience, Inc. Sigma receptor ligands and the use thereof
US5387685A (en) 1993-07-16 1995-02-07 American Cyanamid Co MDR reversal agents
GB9322976D0 (en) 1993-11-08 1994-01-05 Pfizer Ltd Therapeutic agents
US5421119A (en) * 1994-05-31 1995-06-06 Miner; Donald W. Rifle firing pin
DE4419315A1 (de) 1994-06-01 1995-12-07 Merckle Gmbh Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie
DE4419247A1 (de) 1994-06-01 1995-12-07 Merckle Gmbh Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie
DE4419246A1 (de) 1994-06-01 1995-12-07 Merckle Gmbh Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie
DE4427838A1 (de) 1994-08-05 1996-02-08 Thomae Gmbh Dr K Kondensierte Azepinderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE4429079A1 (de) 1994-08-17 1996-02-22 Thomae Gmbh Dr K Cyclische Harnstoffderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
GB9508622D0 (en) 1995-04-28 1995-06-14 Pfizer Ltd Therapeutic agants
FR2740531B1 (fr) * 1995-10-27 1997-11-21 Legris Sa Perfectionnement a un dispositif de liaison d'un tube a un embout
CA2190708A1 (en) 1995-12-08 1997-06-09 Johannes Aebi Aminoalkyl substituted benzo-heterocyclic compounds
US5892116A (en) 1996-01-03 1999-04-06 Georgetown University Gelators
US5925651A (en) 1996-04-03 1999-07-20 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US5691362A (en) 1996-06-05 1997-11-25 Schering-Plough Corporation Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists
EP0920417A4 (en) 1996-08-15 1999-12-29 Smithkline Beecham Corp IL-8 RECEPTOR ANTAGONISTS
US5908830A (en) 1996-10-31 1999-06-01 Merck & Co., Inc. Combination therapy for the treatment of diabetes and obesity
EP0973778A1 (en) 1997-03-07 2000-01-26 Novo Nordisk A/S 4,5,6,7-TETRAHYDRO-THIENO 3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE
US5795895A (en) 1997-06-13 1998-08-18 Anchors; J. Michael Combination anorexiant drug therapy for obesity using phentermine and an SSRI drug
AUPP020297A0 (en) 1997-11-05 1997-11-27 University Of Melbourne, The A novel receptor, and compounds which bind thereto
JP4345230B2 (ja) 1998-03-10 2009-10-14 小野薬品工業株式会社 カルボン酸誘導体およびその誘導体を有効成分として含有する薬剤
EP1072591A4 (en) 1998-03-26 2005-01-05 Santen Pharmaceutical Co Ltd NEW UREA CONNECTIONS
EP0987235B1 (en) 1998-08-25 2003-03-12 MERCK PATENT GmbH Method for the conversion of arenes or alkenes with iodoalkenes, aryl iodides or arenediazonium salts
JP2000159702A (ja) 1998-11-25 2000-06-13 Mitsubishi Chemicals Corp １−（４−クロロフェニル）−ω−ブロモアルカンの製造方法
EP1074549B1 (en) 1999-08-06 2003-11-19 F. Hoffmann-La Roche Ag Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors
DE60006618T2 (de) 1999-08-06 2004-09-23 F. Hoffmann-La Roche Ag Tetrahydro-benzo(d)azepine und deren Verwendung als metabotrope Glutamatrezeptor-Antagonisten
US6403657B1 (en) 1999-10-04 2002-06-11 Martin C. Hinz Comprehensive pharmacologic therapy for treatment of obesity
DE10003708A1 (de) 2000-01-28 2001-08-02 Solvent Innovation Gmbh Neuartige chirale ionische Flüssigkeiten und Verfahren zu ihrer Darstellung in enantiomerenreiner oder enantiomerenangereicherter Form
BR0111947A (pt) 2000-06-30 2003-05-06 Glaxo Group Ltd Composto, composição farmacêutica, método para o tratamento de um distúrbio em um mamìfero, uso de um composto e processo para preparar, um composto
CN1254474C (zh) 2000-11-14 2006-05-03 史密斯克莱·比奇曼公司 作为多巴胺D<sub>3</sub>受体调节剂(精神抑制药)的四氢苯并氮杂䓬衍生物
DE10057751A1 (de) 2000-11-22 2002-05-23 Bayer Ag Neue Carbamat-substituierte Pyrazolopyridinderivate
GB0030710D0 (en) 2000-12-15 2001-01-31 Hoffmann La Roche Piperazine derivatives
WO2002074746A1 (en) 2001-03-16 2002-09-26 Yamanouchi Pharmaceutical Co., Ltd. Benzazepine derivatives
US6825198B2 (en) 2001-06-21 2004-11-30 Pfizer Inc 5-HT receptor ligands and uses thereof
JP2003034681A (ja) * 2001-07-18 2003-02-07 Tosoh Corp Ｎ−（ω−ブロモアルキル）フタルイミド類の製造方法
BR0212787A (pt) 2001-09-24 2005-01-25 Elan Pharm Inc Composto ou sal farmaceuticamente aceitável do mesmo, métodos de tratamento ou prevenção de doenças e de preparação de um composto, uso de um composto ou sal, e, composição farmacêutica
JP2005518414A (ja) 2001-12-21 2005-06-23 スミスクライン　ビーチャム　パブリック　リミテッド　カンパニー ドーパミン受容体のモジュレーターとしての７−スルホニル−３−ベンゾアゼピン誘導体およびｃｎｓ障害の治療のためのその使用
WO2003057161A2 (en) 2001-12-28 2003-07-17 Bayer Pharmaceuticals Corporation BENZOTHIENO [3,2-c]PYRAZOLYL AND BENZOFURANO [3,2-c] PYRAZOLYL COMPOUNDS, THEIR USE IN DISEASES ASSOCIATED WITH THE 5-HT2C RECEPTOR AND INTERMEDIATE COMPOUNDS THEREOF
JP2005519915A (ja) 2002-01-18 2005-07-07 セレテック・リミテッド・ライアビリティ・カンパニー Ｅｄｇ受容体に関連する症状の処置方法
ATE486842T1 (de) 2002-03-12 2010-11-15 Merck Sharp & Dohme Substituierte amide
US6953787B2 (en) 2002-04-12 2005-10-11 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
DE10220570A1 (de) 2002-05-08 2003-11-20 Bayer Ag Carbamat-substituierte Pyrazolopyridine
GB0224557D0 (en) 2002-10-22 2002-11-27 Glaxo Group Ltd Novel compounds
JP4188060B2 (ja) 2002-11-08 2008-11-26 北興化学工業株式会社 １−置換フェニル−ω−ブロモアルカンの製造法
DE10261131A1 (de) 2002-12-20 2004-07-01 Grünenthal GmbH Substituierte 5-Aminomethyl-1H-pyrrol-2-carbonsäureamide
US7145012B2 (en) 2003-04-23 2006-12-05 Pfizer Inc. Cannabinoid receptor ligands and uses thereof
US7232823B2 (en) 2003-06-09 2007-06-19 Pfizer, Inc. Cannabinoid receptor ligands and uses thereof
MXPA05013364A (es) 2003-06-17 2006-03-17 Arena Pharm Inc Procedimiento para preparar 3-benzazepinas.
US7704993B2 (en) 2003-06-17 2010-04-27 Arena Pharmaceuticals, Inc. Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
TW200510324A (en) 2003-08-11 2005-03-16 Lilly Co Eli 6-(2,2,2-trifluoroethylamino)-7-chiloro-2, 3, 4, 5-tetrahydro-1h-benzo[d]azepine as a 5-ht2c receptor agonist
US20080009478A1 (en) 2003-10-22 2008-01-10 Arena Pharmaceuticals, Inc. Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases
US20070275949A1 (en) 2003-10-22 2007-11-29 Arena Pharmaceuticals, Inc. Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases
US20090143276A1 (en) * 2007-10-08 2009-06-04 Anaphore, Inc. Trimeric IL-1Ra
EA011011B1 (ru) 2004-02-25 2008-12-30 Эли Лилли Энд Компани 6-ЗАМЕЩЁННЫЕ 2,3,4,5-ТЕТРАГИДРО-1H-БЕНЗО[d]АЗЕПИНЫ В КАЧЕСТВЕ АГОНИСТОВ РЕЦЕПТОРОВ 5-HT
SE0401871D0 (sv) 2004-07-15 2004-07-15 Glucogene Medical Hfm Ab New compositions
MX2007001337A (es) 2004-08-02 2008-03-13 Genmedica Therapeutics Sl Compuestos para inhibir amina-oxidasas que contienen cobre y usos de los mismos.
US8178077B2 (en) 2004-10-19 2012-05-15 Reverse Proteomics Research Institute Co., Ltd. Drug development target protein and target gene, and method of screening
BRPI0519726B8 (pt) 2004-12-21 2021-05-25 Arena Pharm Inc composto de hemidrato de (r)-8-cloro-1-metil-2,3,4,5-tetraidro-1h-3-benzazepina, composição compreendendo o referido composto e seus usos
BRPI0515862A2 (pt) 2004-12-23 2011-10-11 Arena Pharm Inc uso de fentermina e agonista seletivo do receptor de 5ht-2c na preparação de composições, composições moduladoras do receptor de 5ht-2c e forma de dosagem unitária compreendendo as mesmas
JP4984567B2 (ja) 2006-02-24 2012-07-25 東ソー株式会社 分岐アルキルブロミドの製造方法
JP5404414B2 (ja) 2006-12-05 2014-01-29 アリーナ ファーマシューティカルズ， インコーポレイテッド （ｒ）−８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピンおよびその中間体を調製するための方法
JP5339263B2 (ja) 2007-07-26 2013-11-13 コクヨ株式会社 引き戸の取付構造、引き戸及び収納装置
US8166624B2 (en) * 2008-01-17 2012-05-01 Jon Andreasen Linearly extendible impact anchor driving pole and anchor system
US8822727B2 (en) 2008-03-04 2014-09-02 Arena Pharmaceuticals, Inc. Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
WO2010148207A2 (en) 2009-06-18 2010-12-23 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-ht2c receptor agonists
US8999970B2 (en) 2010-09-01 2015-04-07 Arena Pharmaceuticals, Inc. Administration of an anti-obesity compound to individuals with renal impairment
CN102126988A (zh) 2010-12-17 2011-07-20 张家港瀚康化工有限公司 4-(4-氯苯基)-2-溴甲基-2-苯基丁腈的制备方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007120517A2 (en) * 2006-04-03 2007-10-25 Arena Pharmaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto

Also Published As

Publication number Publication date
JP2011513402A (ja) 2011-04-28
WO2009111004A1 (en) 2009-09-11
CN102015591A (zh) 2011-04-13
JP5491421B2 (ja) 2014-05-14
US20110015438A1 (en) 2011-01-20
US8822727B2 (en) 2014-09-02
EP2288585A1 (en) 2011-03-02

Similar Documents

Publication Publication Date Title
CN102015591A (zh) 制备与5-ht2c激动剂(r)-8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂䓬相关的中间体的方法
CN101547892B (zh) 制备(r)-8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的方法和其中间体
US8168782B2 (en) Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto
US8367657B2 (en) Processes for preparing 3-benzazepines
FI95246C (fi) Menetelmä terapeuttisesti käyttökelpoisten, substituoitujen aminometyylibentsodihydropyraanien ja aminometyyli(di- ja tetra)hydronaftaleenien valmistamiseksi
US8952197B2 (en) Processes for the preparation of 5-HT2C receptor agonists
EP1838677A2 (en) Crystalline forms of (r)-8-chloro-1-methyl- 2,3,4,5-tetrahydro-1h-3-benzazepine hydrochloride
EA016675B1 (ru) Способы получения фенилпиразолов и кристаллическая форма производного фенилпиразола
KR20030068583A (ko) 순수한 온단세트론 하이드로클로라이드 이수화물의 개선된제조 방법
KR101153713B1 (ko) 이토프라이드의 제조 방법 및 중간체 화합물
KR20040043176A (ko) 5-치환 이소벤조퓨란의 제조 방법
AU2002236753A1 (en) An improved process for preparing pure ondansetron hydrochloride dihydrate
US20060094876A1 (en) Process for making camptothecin derivatives
CN101687859A (zh) 阿呋唑嗪及其盐的制备工艺
CN102282137A (zh) 二苯并氧杂七环化合物的制备方法
HK1133635B (en) Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof
HK1176604A (en) Process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20140129

Termination date: 20160303