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

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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
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chloro
phenyl
ethanol
propan
chlorophenyl
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CN102015591A (zh
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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
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Arena Pharmaceuticals Inc
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    • 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

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  • 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

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

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US (1) US8822727B2 (https=)
EP (1) EP2288585A1 (https=)
JP (1) JP5491421B2 (https=)
CN (1) CN102015591B (https=)
WO (1) WO2009111004A1 (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE028976T2 (en) 2003-06-17 2017-02-28 Arena Pharm Inc 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
SG158168A1 (en) 2004-12-23 2010-01-29 Arena Pharm Inc 5ht2c receptor modulator compositions and methods of use
EP2471779A1 (en) 2006-04-03 2012-07-04 Arena Pharmaceuticals, Inc. Process for the resolution of a mixture of (R)- and (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
CN102015591B (zh) 2008-03-04 2014-01-29 艾尼纳制药公司 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
US8952197B2 (en) 2009-06-18 2015-02-10 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
JP2013536859A (ja) 2010-09-01 2013-09-26 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 ５−ｈｔ２ｃアゴニストの非吸湿性塩
EP3485878A1 (en) 2010-09-01 2019-05-22 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-ht2c agonists useful for weight management
KR20140091458A (ko) 2010-09-01 2014-07-21 아레나 파마슈티칼스, 인크. 신장 손상을 갖는 개체에 대한 로카세린의 투여
KR20130138770A (ko) 2010-09-01 2013-12-19 아레나 파마슈티칼스, 인크. 광학적으로 활성 산을 갖는 로르카세린의 염
AU2011296027A1 (en) 2010-09-01 2013-04-04 Arena Pharmaceuticals, Inc. Fast-dissolve dosage forms 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
WO2014058441A1 (en) 2012-10-09 2014-04-17 Arena Pharmaceuticals, Inc. Method of weight management
EP2999692A1 (en) 2013-05-20 2016-03-30 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
TW201618787A (zh) 2014-10-30 2016-06-01 艾尼納製藥公司 組合物及方法
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
CH498122A (de) 1968-02-09 1970-10-31 Geigy Ag J R Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates
CH481110A (de) 1967-02-17 1969-11-15 Geigy Ag J R Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen
CH500194A (de) 1968-02-15 1970-12-15 Ciba Geigy Ag Verfahren zur Herstellung von Tetrahydroazepinderivaten
CA974989A (en) 1968-03-11 1975-09-23 Wallace And Tiernan Inc. Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby
US4233217A (en) 1968-03-11 1980-11-11 Pennwalt Corporation Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines
FR314F (https=) 1968-03-22 1970-05-25
FR7736M (https=) 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 (https=) 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
DE3272044D1 (de) 1981-11-27 1986-08-21 Smithkline Beckman Corp 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
WO1988007858A1 (en) 1987-04-09 1988-10-20 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
AU8201591A (en) 1990-06-15 1992-01-07 Schering Corporation 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substitued 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
EP0589973A1 (en) 1991-06-21 1994-04-06 Smithkline Beecham Plc Medicaments
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
DE69413434T2 (de) * 1993-02-26 1999-04-01 Mitsui Chemicals, Inc., Tokio/Tokyo Harze für elektrophotographische Entwickler
CA2166100A1 (en) 1993-06-23 1995-01-05 Richard A. Glennon 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
DE4419247A1 (de) 1994-06-01 1995-12-07 Merckle Gmbh Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie
DE4419315A1 (de) 1994-06-01 1995-12-07 Merckle Gmbh Heteropyrrolizinverbindungen 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
JP2001514631A (ja) 1997-03-07 2001-09-11 ノボ ノルディスク アクティーゼルスカブ ４，５，６，７−テトラヒドロ−チエノ［３，２−ｃ］ピリジン誘導体類、それらの製造方法及び使用
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
ATE451346T1 (de) 1998-03-10 2009-12-15 Ono Pharmaceutical Co Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten
CN1305846C (zh) 1998-03-26 2007-03-21 参天制药株式会社 脲衍生物
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
DE60006618T2 (de) 1999-08-06 2004-09-23 F. Hoffmann-La Roche Ag Tetrahydro-benzo(d)azepine und deren Verwendung als metabotrope Glutamatrezeptor-Antagonisten
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
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
PL204958B1 (pl) 2000-06-30 2010-02-26 Glaxo Group Ltd Ditosylany związków chinazolinowych, środek farmaceutyczny i zastosowanie tych związków
JP4272423B2 (ja) 2000-11-14 2009-06-03 スミスクライン ビーチャム ピー エル シー ドーパミンｄ３受容体のモジュレーターとして有用なテトラヒドロベンズアゼピン誘導体（抗精神病剤）
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
JPWO2002074746A1 (ja) 2001-03-16 2004-07-08 山之内製薬株式会社 ベンゾアゼピン誘導体
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
EP1430032A2 (en) 2001-09-24 2004-06-23 Elan Pharmaceuticals, Inc. Substituted amides for the treatment of neurological disorders
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
AU2002367323A1 (en) 2001-12-28 2003-07-24 Bayer Pharmaceuticals Corporation Benzothieno (3,2-
EP1513522A2 (en) 2002-01-18 2005-03-16 Sri International Methods of treating conditions associated with an edg receptor
NZ534757A (en) 2002-03-12 2006-07-28 Merck & Co Inc Substituted amides
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
CN1805938B (zh) 2003-06-17 2010-06-16 艾尼纳制药公司 用于治疗5ht2c受体相关疾病的苯并氮杂卓衍生物
HUE028976T2 (en) 2003-06-17 2017-02-28 Arena Pharm Inc 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
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
WO2005042491A1 (en) 2003-10-22 2005-05-12 Arena Pharmaceuticals, Inc. Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
WO2005042490A1 (en) 2003-10-22 2005-05-12 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
CN102329267A (zh) 2004-02-25 2012-01-25 伊莱利利公司 作为5-HT2C受体激动剂的6-取代的2,3,4,5-四氢-1H-苯并［d］氮杂䓬
SE0401871D0 (sv) 2004-07-15 2004-07-15 Glucogene Medical Hfm Ab New compositions
US20080269282A1 (en) 2004-08-02 2008-10-30 Genmedica Therapeutics Sl Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof
JPWO2006043710A1 (ja) 2004-10-19 2008-05-22 株式会社リバース・プロテオミクス研究所 創薬標的タンパク質及び標的遺伝子、並びにスクリーニング方法
SI1838677T1 (sl) 2004-12-21 2010-01-29 Arena Pharm Inc Kristalne oblike (R)-8-kloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzazepin hidroklorida
SG158168A1 (en) 2004-12-23 2010-01-29 Arena Pharm Inc 5ht2c receptor modulator compositions and methods of use
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
US8299241B2 (en) 2006-12-05 2012-10-30 Arena Pharmaceuticals, Inc. Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates thereof
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
CN102015591B (zh) 2008-03-04 2014-01-29 艾尼纳制药公司 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
US8952197B2 (en) 2009-06-18 2015-02-10 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
KR20140091458A (ko) 2010-09-01 2014-07-21 아레나 파마슈티칼스, 인크. 신장 손상을 갖는 개체에 대한 로카세린의 투여
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

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