ZA200408506B - 5HT2c receptor modulators - Google Patents
5HT2c receptor modulators Download PDFInfo
- Publication number
- ZA200408506B ZA200408506B ZA200408506A ZA200408506A ZA200408506B ZA 200408506 B ZA200408506 B ZA 200408506B ZA 200408506 A ZA200408506 A ZA 200408506A ZA 200408506 A ZA200408506 A ZA 200408506A ZA 200408506 B ZA200408506 B ZA 200408506B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzazepine
- tetrahydro
- methyl
- methoxy
- bromo
- Prior art date
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- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 title 1
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
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Families Citing this family (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8478824B2 (en) * | 2002-02-05 | 2013-07-02 | Portauthority Technologies Inc. | Apparatus and method for controlling unauthorized dissemination of electronic mail |
SE0200968D0 (sv) * | 2002-03-26 | 2002-03-26 | Lars Baltzer | Novel polypeptide scaffolds and use thereof |
US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
TWI329111B (en) | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
MXPA05006567A (es) | 2002-12-20 | 2005-08-16 | Glaxo Group Ltd | Derivados de benzazepina para el tratamiento de trastornos neurologicos. |
CN101792417A (zh) * | 2003-06-17 | 2010-08-04 | 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 |
EP2189448B1 (de) * | 2003-06-17 | 2014-01-29 | Arena Pharmaceuticals, Inc. | Prozesse zur Trennung von 3-Benzazepin-Razematen |
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 |
US20070275949A1 (en) * | 2003-10-22 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases |
US20080009478A1 (en) * | 2003-10-22 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases |
DE602004017206D1 (de) * | 2003-10-23 | 2008-11-27 | Hoffmann La Roche | Benzazepin-derivate als mao-b-hemmer |
PL1720836T3 (pl) | 2004-02-25 | 2014-09-30 | Lilly Co Eli | 6-podstawione 2,3,4,5-tetrahydro-1h-benzo [d]azepiny jako agoniści receptora 5-ht2c |
EP2248524A3 (de) | 2004-08-25 | 2011-03-09 | Takeda Pharmaceutical Company Limited | Mittel zur prävention/behandlung von stressbedingter harninkontinenz und vorsorgeuntersuchungsverfahren dafür |
ATE507832T1 (de) * | 2004-09-03 | 2011-05-15 | Athersys Inc | Trizyklische heteroaryl-piperazine, pyrrolidine und azetidine als serotonin-rezeptor-modulatoren |
US7528175B2 (en) * | 2004-10-08 | 2009-05-05 | Inverseon, Inc. | Method of treating airway diseases with beta-adrenergic inverse agonists |
WO2006044762A2 (en) * | 2004-10-15 | 2006-04-27 | Bayer Pharmaceuticals Corporation | Tetrahydro-5h-pyrimido[4,5-d]azepine derivatives useful for the treatment of diseases associated with the 5-ht2c receptor |
BRPI0519013A2 (pt) * | 2004-12-13 | 2009-11-03 | Lilly Co Eli | composto ou esteroisÈmeros únicos, misturas de esteroisÈmeros, sais, tautÈmeros ou pró-drogas destes farmaceuticamente aceitáveis, composição farmacêutica, e, uso de um composto |
KR101281919B1 (ko) | 2004-12-21 | 2013-07-03 | 아레나 파마슈티칼스, 인크. | (r)-8-클로로-1-메틸-2,3,4,5-테트라히드로-1h-3-벤즈아제핀 히드로클로라이드의 결정질 형태 |
PT1833473E (pt) | 2004-12-23 | 2009-12-17 | Arena Pharm Inc | Composições de modulador de receptor 5ht2c e métodos de utilização |
AU2012201515B2 (en) * | 2004-12-23 | 2015-01-29 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulator compositions and methods of use |
EP1869000A1 (de) * | 2005-03-31 | 2007-12-26 | Pfizer Products Incorporated | Cyclopentapyridin- und tetrahydrochinolinderivate |
WO2007025144A1 (en) * | 2005-08-24 | 2007-03-01 | University Of Illinois - Chicago | 5-ht2c receptor agonists as anorectic agents |
US8420631B2 (en) * | 2005-09-01 | 2013-04-16 | Eli Lilly And Company | 6-substituted-2,3,4,5-tetrahydro-1H-benzo[d]azepines as 5-HT2C receptor agonists |
WO2007028082A1 (en) * | 2005-09-01 | 2007-03-08 | Eli Lilly And Company | 6-substituted- 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists |
JP5249031B2 (ja) * | 2005-09-01 | 2013-07-31 | イーライ リリー アンド カンパニー | 5−HT2C受容体アゴニストとしての6−N結合型へテロ環置換された2,3,4,5−テトラヒドロ−1H−ベンゾ[d]アゼピン |
SI1924561T1 (sl) | 2005-09-01 | 2013-02-28 | Eli Lilly And Company | 6-arilalkilamino-2,3,4,5-tetrahidro-1h-benzo(d)azepini kot agonisti 5-ht2c receptorja |
DE102006009004A1 (de) * | 2006-02-23 | 2007-09-06 | Sustech Gmbh & Co. Kg | Multifunktionelle sternförmige Präpolymere, deren Herstellung und Verwendung |
EP2001852A2 (de) | 2006-04-03 | 2008-12-17 | Arena Pharmaceuticals, Inc. | Verfahren zur herstellung von 8-chlor-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin und entsprechenden zwischenprodukten |
EP2742936A1 (de) | 2006-05-16 | 2014-06-18 | Takeda Pharmaceutical Company Limited | Kondensierte heterocyclische Verbindung und ihre Verwendung |
US7897595B2 (en) * | 2006-05-26 | 2011-03-01 | Forest Laboratories Holdings Limited | Pyridoazepine derivatives |
WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
KR20090029299A (ko) * | 2006-07-14 | 2009-03-20 | 화이자 프로덕츠 인코포레이티드 | (7s)-7-[(5-플루오로-2-메틸-벤질)옥시]-2-[(2r)-2-메틸피페라진-1-일]-6,7-다이하이드로-5h-사이클로펜타[b]피리딘의 타르트레이트 염 |
CA2670285A1 (en) * | 2006-12-05 | 2008-06-12 | Arena Pharmaceuticals, Inc. | Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof |
CL2007003580A1 (es) * | 2006-12-11 | 2009-03-27 | Boehringer Ingelheim Int | Compuestos derivados de piridazina, antagonistas de mch; composicion farmaceutica que comprende a dicho compuesto; procedimiento de preparacion; y uso del compuesto en el tratamiento de trastornos metabolicos y/o trastornos alimentarios como obesidad, bulimia, anorexia, hiperfagia, diabetes. |
US20090143363A1 (en) * | 2007-10-15 | 2009-06-04 | Concert Pharmaceuticals, Inc. | Deuterated lorcaserin |
US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
JP5491421B2 (ja) * | 2008-03-04 | 2014-05-14 | 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アゴニストである(r)−8−クロロ−1−メチル−2,3,4,5−テトラヒドロ−1h−3−ベンゾアゼピンに関連する中間体の調製のためのプロセス |
EP2256105B1 (de) | 2008-03-26 | 2013-12-04 | Daiichi Sankyo Company, Limited | Neuartiges tetrahydroisochinolin-derivat |
EP2246331A1 (de) * | 2009-04-24 | 2010-11-03 | Westfälische Wilhelms-Universität Münster | NR2B-selektive NMDA-Rezeptorantagonisten |
CN102648170A (zh) | 2009-06-18 | 2012-08-22 | 艾尼纳制药公司 | 制备5-ht2c受体激动剂的方法 |
EP2510949A4 (de) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | Therapeutikum für fibromyalgie |
EP2531485B1 (de) | 2010-02-04 | 2019-04-24 | The Board of Trustees of the University of Illionis | Hochselektive 5-ht(2c)-rezeptoragonisten mit antagonistenaktivität am 5-ht(2b)-rezeptor |
BR112012021231A2 (pt) | 2010-02-26 | 2015-09-08 | Basf Plant Science Co Gmbh | método para acentuar o rendimento em plantas, planta, construto, uso de um construto, método para a produção de uma planta transgênica, partes coletáveis de uma planta, produtos derivados de uma planta, uso de um ácido nucleíco e método para a produção de um produto |
US20130012432A1 (en) | 2010-02-26 | 2013-01-10 | Novo Nordisk A/S | Peptides for Treatment of Obesity |
US20110269744A1 (en) * | 2010-03-12 | 2011-11-03 | Astellas Pharma Inc. | Benzazepine Compound |
JP6054861B2 (ja) | 2010-03-26 | 2016-12-27 | ノヴォ ノルディスク アー/エス | 新規のグルカゴン類似体 |
US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
MX2013002430A (es) * | 2010-09-01 | 2013-07-22 | Arena Pharm Inc | Formas de dosis de disolucion de rápida de agonistas de 5-ht2c. |
CN103189360A (zh) | 2010-09-01 | 2013-07-03 | 艾尼纳制药公司 | 5-ht2c激动剂的非吸湿性盐 |
WO2012030938A1 (en) * | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
ES2704455T3 (es) * | 2010-09-01 | 2019-03-18 | Arena Pharm Inc | Formas farmacéuticas de liberación modificada de agonistas de 5-HT2C útiles para la gestión del peso |
EP2939677A1 (de) | 2010-09-01 | 2015-11-04 | Arena Pharmaceuticals, Inc. | Verabreichung von lorcaserin an personen mit nierenerkrankungen |
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 |
BR112013024076A2 (pt) | 2011-03-28 | 2016-12-06 | Novo Nordisk As | análogos de glucagon |
TWI596110B (zh) | 2011-09-23 | 2017-08-21 | 諾佛 儂迪克股份有限公司 | 新穎升糖素類似物 |
CN102895233B (zh) * | 2012-09-04 | 2015-06-24 | 苏州大学 | 苯并氮杂卓类化合物在制备预防或治疗癫痫的药物中的应用 |
AU2012392187B2 (en) | 2012-10-09 | 2018-07-12 | Arena Pharmaceuticals, Inc. | Method of weight management |
WO2014060575A2 (en) | 2012-10-19 | 2014-04-24 | Medichem S.A. | Process for the enantioselective synthesis of a tetrahydrobenzazepine compound |
AU2014255608B2 (en) | 2013-04-18 | 2018-01-25 | Novo Nordisk A/S | Stable, protracted GLP-1/glucagon receptor co-agonists for medical use |
CN105431415A (zh) | 2013-05-20 | 2016-03-23 | 斯洛文尼亚莱柯制药股份有限公司 | 通过烯烃的弗瑞德-克来福特烷基化进行的8-氯-3-苯并[d]氮杂*的新合成方法 |
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 |
CN105555769A (zh) * | 2013-07-19 | 2016-05-04 | 斯洛文尼亚莱柯制药股份有限公司 | 不需要的对映异构体的外消旋化方法 |
WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
EP2868656A1 (de) | 2013-11-05 | 2015-05-06 | LEK Pharmaceuticals d.d. | Stabilisiertes amorphes Lorcaserin Hydrochlorid |
CN104936947B (zh) * | 2013-12-27 | 2017-03-08 | 杭州普晒医药科技有限公司 | 氯卡色林盐及其晶体、其制备方法和用途 |
US9981912B2 (en) | 2014-04-21 | 2018-05-29 | Hangzhou Pushai Pharmaceutical Technology Co., Ltd. | Cocrystal of lorcaserin, preparation methods, pharmaceutical compositions and uses thereof |
CN106536547A (zh) | 2014-06-04 | 2017-03-22 | 诺和诺德股份有限公司 | 用于医疗用途的glp‑1/胰高血糖素受体共激动剂 |
WO2016069875A1 (en) | 2014-10-30 | 2016-05-06 | Arena Pharmaceuticals, Inc. | Compositions and methods for ceasing tobacco smoking |
WO2016123164A1 (en) | 2015-01-29 | 2016-08-04 | The Board Of Trustees Of The University Of Illinois | Cyclopropylmethanamines as selective 5-ht(2c) receptor agonists |
MA42527A (fr) * | 2015-07-31 | 2021-04-07 | Arena Pharm Inc | Agonistes de récepteur 5-ht2c et compositions et procédés d'utilisation |
DE102015117882A1 (de) * | 2015-10-21 | 2017-04-27 | Mehrdad Ghashghaeinia | Pharmazeutische Zusammensetzung |
EP3210975A1 (de) | 2016-02-24 | 2017-08-30 | Enantia, S.L. | Cokristalle von lorcaserin |
JP6725838B2 (ja) * | 2016-09-16 | 2020-07-22 | 富士通クライアントコンピューティング株式会社 | ヒンジ、スタンド装置、及び、電子機器 |
MA49883A (fr) | 2017-03-15 | 2021-04-21 | Novo Nordisk As | Composés bicycliques aptes à se lier au récepteur de mélanocortine 4 |
WO2018170179A1 (en) | 2017-03-15 | 2018-09-20 | Silverback Therapeutics, Inc. | Benzazepine compounds, conjugates, and uses thereof |
EP3733204A4 (de) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | Therapeutikum für belastungsinkontinenz und stuhlinkontinenz |
US20210221867A1 (en) | 2018-05-15 | 2021-07-22 | Novo Nordisk A/S | Compounds Capable of Binding to Melanocortin 4 Receptor |
KR20190132711A (ko) | 2018-05-21 | 2019-11-29 | 주식회사 다림바이오텍 | 비만 예방 또는 치료용 약학 조성물 |
KR20190133482A (ko) | 2018-05-23 | 2019-12-03 | 동국제약 주식회사 | 흰강낭콩 및 아위버섯 추출물을 함유하는 항비만 또는 체지방 감소용 조성물 |
WO2020053414A1 (en) | 2018-09-14 | 2020-03-19 | Novo Nordisk A/S | Bicyclic compounds capable of acting as melanocortin 4 receptor agonists |
US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
EP4106819A1 (de) | 2020-02-21 | 2022-12-28 | Silverback Therapeutics, Inc. | Nectin-4-antikörper-konjugate und verwendungen davon |
KR20230047361A (ko) | 2020-07-01 | 2023-04-07 | 아르스 파마슈티컬스 인크. | 항-asgr1 항체 접합체 및 이의 용도 |
Family Cites Families (80)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US372058A (en) | 1887-10-25 | William m | ||
US434607A (en) | 1890-08-19 | Barrel-washing machine | ||
US405495A (en) | 1889-06-18 | Picker-staff connection for looms | ||
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 |
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 |
FR7736M (de) | 1968-09-02 | 1970-03-09 | ||
US3592523A (en) * | 1969-05-19 | 1971-07-13 | Ncr Co | Angle multiplier apparatus |
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 (de) * | 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 |
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 |
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 |
EP0161350A1 (de) | 1981-11-27 | 1985-11-21 | Smithkline Beckman Corporation | Verfahren zur Herstellung von Benzazepinen |
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 |
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 |
US4762845A (en) * | 1986-05-21 | 1988-08-09 | Abbott Laboratories | 7-(3-Substituted imino-1-pyrrolidinyl)-quinolone-3-carboxylic acids |
EP0285287A3 (de) | 1987-03-23 | 1990-08-16 | Smithkline Beecham Corporation | Verwendung von 3-Benzazepinen zur Behandlung von gastrointestinalen Mobilitätsstörungen |
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 |
US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | 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 |
US5105639A (en) * | 1989-02-23 | 1992-04-21 | Spiro America Inc. | Apparatus for forming spiral pipe |
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 |
IL98487A0 (en) | 1990-06-15 | 1992-07-15 | Schering Corp | 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substituted benzazepines and pharmaceutical compositions containing them |
US5275915A (en) | 1991-06-05 | 1994-01-04 | Dainippon Ink And Chemicals, Inc. | Developer for light-sensitive material |
AU1927992A (en) | 1991-06-21 | 1993-01-25 | Smithkline Beecham Plc | Medicaments |
EP0558824A1 (de) | 1992-02-04 | 1993-09-08 | Duphar International Research B.V | Verfahren zur Herstellung von vicinalen Aminoalkoholen und deren optisch aktive O-geschützte Derivate |
JPH05339263A (ja) | 1992-06-08 | 1993-12-21 | Wakunaga Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
JPH06298746A (ja) | 1993-04-19 | 1994-10-25 | Showa Denko Kk | 環状イミド酸エステルの製造法 |
ZA944513B (en) | 1993-06-23 | 1996-01-16 | Cambridge Neuroscience Inc | Sigma receptor ligands |
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 |
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 |
JPH08134048A (ja) | 1994-11-08 | 1996-05-28 | Sumitomo Chem Co Ltd | オキサゾリン類の製造法 |
GB9508622D0 (en) | 1995-04-28 | 1995-06-14 | Pfizer Ltd | Therapeutic agants |
US5958543A (en) | 1995-07-07 | 1999-09-28 | Stor Media,Inc. | Micro-texturing for sputtered, thin film magnetic media disks utilizing titanium sputtered in the presence of hydrogen to form micro-texturing |
JPH0930960A (ja) | 1995-07-18 | 1997-02-04 | Takasago Internatl Corp | 真菌感染症治療剤 |
JPH0987258A (ja) | 1995-09-28 | 1997-03-31 | Sumitomo Chem Co Ltd | オキサゾリン類、その製造方法およびそれを用いる不斉シクロプロパンカルボン酸類の製造方法 |
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 (de) | 1996-08-15 | 1999-12-29 | Smithkline Beecham Corp | Il-8 rezeptor antagonisten |
WO1998040385A1 (en) | 1997-03-07 | 1998-09-17 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO[3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
AUPP020297A0 (en) | 1997-11-05 | 1997-11-27 | University Of Melbourne, The | A novel receptor, and compounds which bind thereto |
EP0987235B1 (de) | 1998-08-25 | 2003-03-12 | MERCK PATENT GmbH | Verfahren zur Umsetzung von Arenen oder Alkenen mit Iodalkenen, Aryliodiden oder Arendiazoniumsalzen |
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 (de) | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepine und deren Verwendung als metabotrope Glutamatrezeptor-Antagonisten |
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 |
IL155873A0 (en) | 2000-11-14 | 2003-12-23 | Smithkline Beecham Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
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 |
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 |
WO2003062392A2 (en) | 2002-01-18 | 2003-07-31 | Ceretek Llc | Methods of treating conditions associated with an edg receptor |
CA2478183C (en) | 2002-03-12 | 2010-02-16 | Merck & Co. Inc. | Substituted amides |
US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
EP2189448B1 (de) | 2003-06-17 | 2014-01-29 | Arena Pharmaceuticals, Inc. | Prozesse zur Trennung von 3-Benzazepin-Razematen |
CN101792417A (zh) | 2003-06-17 | 2010-08-04 | 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 |
US20070275949A1 (en) | 2003-10-22 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2C Receptor Associated Diseases |
US20080009478A1 (en) | 2003-10-22 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases |
WO2006013209A2 (en) | 2004-08-02 | 2006-02-09 | Genmedica Therapeutics Sl | Compounds for inhibiting copper-containing amine oxidases and uses thereof |
WO2006043710A1 (ja) | 2004-10-19 | 2006-04-27 | Reverse Proteomics Research Institute Co., Ltd. | 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 |
KR101281919B1 (ko) | 2004-12-21 | 2013-07-03 | 아레나 파마슈티칼스, 인크. | (r)-8-클로로-1-메틸-2,3,4,5-테트라히드로-1h-3-벤즈아제핀 히드로클로라이드의 결정질 형태 |
PT1833473E (pt) | 2004-12-23 | 2009-12-17 | Arena Pharm Inc | Composições de modulador de receptor 5ht2c e métodos de utilização |
EP2001852A2 (de) | 2006-04-03 | 2008-12-17 | Arena Pharmaceuticals, Inc. | Verfahren zur herstellung von 8-chlor-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin und entsprechenden zwischenprodukten |
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