JP2011116780A5 - - Google Patents
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- Publication number
- JP2011116780A5 JP2011116780A5 JP2011049671A JP2011049671A JP2011116780A5 JP 2011116780 A5 JP2011116780 A5 JP 2011116780A5 JP 2011049671 A JP2011049671 A JP 2011049671A JP 2011049671 A JP2011049671 A JP 2011049671A JP 2011116780 A5 JP2011116780 A5 JP 2011116780A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- salt
- composition
- hydrochloride
- 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.)
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Links
- 150000001875 compounds Chemical class 0.000 claims 53
- 238000000034 method Methods 0.000 claims 51
- 150000003839 salts Chemical class 0.000 claims 41
- 239000000203 mixture Substances 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 239000003795 chemical substances by application Substances 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 16
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 14
- 238000004519 manufacturing process Methods 0.000 claims 14
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 230000002140 halogenating effect Effects 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 3
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 3
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000015114 central nervous system disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 230000001939 inductive effect Effects 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 230000036186 satiety Effects 0.000 claims 3
- 235000019627 satiety Nutrition 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 235000002906 tartaric acid Nutrition 0.000 claims 3
- 239000011975 tartaric acid Substances 0.000 claims 3
- 230000004584 weight gain Effects 0.000 claims 3
- 235000019786 weight gain Nutrition 0.000 claims 3
- 230000037213 diet Effects 0.000 claims 2
- 235000005911 diet Nutrition 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 150000003892 tartrate salts Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *C(C*CC(*)(*)c1c(*)c(*)c(*)c(*)c1)O Chemical compound *C(C*CC(*)(*)c1c(*)c(*)c(*)c(*)c1)O 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47928003P | 2003-06-17 | 2003-06-17 | |
| US60/479,280 | 2003-06-17 | ||
| US51296703P | 2003-10-21 | 2003-10-21 | |
| US60/512,967 | 2003-10-21 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006517336A Division JP4920409B2 (ja) | 2003-06-17 | 2004-06-16 | ３−ベンズアゼピンを調製する方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012049640A Division JP5667593B2 (ja) | 2003-06-17 | 2012-03-06 | ３−ベンズアゼピンを調製する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011116780A JP2011116780A (ja) | 2011-06-16 |
| JP2011116780A5 true JP2011116780A5 (cg-RX-API-DMAC7.html) | 2012-04-26 |
| JP5421311B2 JP5421311B2 (ja) | 2014-02-19 |
Family
ID=34221229
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006517336A Expired - Fee Related JP4920409B2 (ja) | 2003-06-17 | 2004-06-16 | ３−ベンズアゼピンを調製する方法 |
| JP2011049671A Expired - Fee Related JP5421311B2 (ja) | 2003-06-17 | 2011-03-07 | ３−ベンズアゼピンを調製する方法 |
| JP2012049640A Expired - Fee Related JP5667593B2 (ja) | 2003-06-17 | 2012-03-06 | ３−ベンズアゼピンを調製する方法 |
| JP2014090162A Withdrawn JP2014133771A (ja) | 2003-06-17 | 2014-04-24 | ３−ベンズアゼピンを調製する方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006517336A Expired - Fee Related JP4920409B2 (ja) | 2003-06-17 | 2004-06-16 | ３−ベンズアゼピンを調製する方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012049640A Expired - Fee Related JP5667593B2 (ja) | 2003-06-17 | 2012-03-06 | ３−ベンズアゼピンを調製する方法 |
| JP2014090162A Withdrawn JP2014133771A (ja) | 2003-06-17 | 2014-04-24 | ３−ベンズアゼピンを調製する方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US8367657B2 (cg-RX-API-DMAC7.html) |
| EP (4) | EP1636191A2 (cg-RX-API-DMAC7.html) |
| JP (4) | JP4920409B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101215107B1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2004267016B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0411613B8 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2529401C (cg-RX-API-DMAC7.html) |
| CY (1) | CY1117619T1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK2332921T3 (cg-RX-API-DMAC7.html) |
| EA (1) | EA016485B1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2571220T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE028976T2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL172331A (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA05013364A (cg-RX-API-DMAC7.html) |
| PL (1) | PL2332921T3 (cg-RX-API-DMAC7.html) |
| SI (1) | SI2332921T1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005019179A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| EA016485B1 (ru) | 2003-06-17 | 2012-05-30 | Арена Фармасьютикалз, Инк. | Способы получения 3-бензазепинов |
| BRPI0411470A (pt) | 2003-06-17 | 2006-07-11 | Arena Pharm Inc | derivados de benzazepina úteis para o tratamento de doenças associadas com o receptor de 5ht2c |
| NZ555981A (en) * | 2004-12-21 | 2011-01-28 | Arena Pharm Inc | Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| CN102631349A (zh) | 2004-12-23 | 2012-08-15 | 艾尼纳制药公司 | 5HT2c受体调节剂组合物和使用方法 |
| CN101258131B (zh) | 2005-09-01 | 2013-07-24 | 伊莱利利公司 | 作为5-HT2c受体激动剂的6-芳烷基氨基-2,3,4,5-四氢-1H-苯并[d]氮杂䓬 |
| JP5165568B2 (ja) | 2005-09-01 | 2013-03-21 | 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−置換−２，３，４，５−テトラヒドロ−１Ｈ−ベンゾ［ｄ］アゼピン |
| BRPI0615033A2 (pt) | 2005-09-01 | 2011-04-26 | Lilly Co Eli | composto, composição farmacêutica, e, uso de um composto |
| US7981882B2 (en) | 2005-09-01 | 2011-07-19 | Eli Lilly And Company | 6-N-linked heterocycle-substituted 2,3,4,5-tetrahydro-1H-benzo[d]azepines as 5-HT2C receptor agonists |
| JP5188986B2 (ja) | 2006-01-19 | 2013-04-24 | アサーシス， インク． | セロトニン５−ｈｔ２ｃ受容体のリガンドとしてのチオフェニルおよびピロリルアゼピンならびにこの使用 |
| 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 |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| US7897595B2 (en) | 2006-05-26 | 2011-03-01 | Forest Laboratories Holdings Limited | Pyridoazepine derivatives |
| ES2522587T3 (es) | 2006-12-05 | 2014-11-17 | Arena Pharmaceuticals, Inc. | Procesos para preparar (R)-8-cloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzacepina e intermedios de la misma |
| US20090143363A1 (en) * | 2007-10-15 | 2009-06-04 | Concert Pharmaceuticals, Inc. | Deuterated lorcaserin |
| WO2009063992A1 (ja) | 2007-11-15 | 2009-05-22 | Takeda Pharmaceutical Company Limited | 縮合ピリジン誘導体およびその用途 |
| 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 |
| US20100222315A1 (en) * | 2008-09-24 | 2010-09-02 | Harbor BioSciencs, Inc. | Patient populations and treatment methods |
| PL2442870T3 (pl) * | 2009-06-15 | 2014-12-31 | Takeda Pharmaceuticals Co | Pochodne pirazynooksazepiny |
| 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 |
| WO2011153206A1 (en) | 2010-06-02 | 2011-12-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| CN103189053A (zh) | 2010-09-01 | 2013-07-03 | 艾尼纳制药公司 | 用于体重控制的5-ht2c激动剂的调节释放剂型 |
| CA2808890A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| CA2808904A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-ht2c agonists |
| SG10201506873WA (en) | 2010-09-01 | 2015-10-29 | Arena Pharm Inc | Fast-dissolve dosage forms of 5-ht2c agonists |
| JP2013539470A (ja) * | 2010-09-01 | 2013-10-24 | 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 | ロルカセリンと光学活性な酸との塩 |
| 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 |
| CA2886875A1 (en) | 2012-10-09 | 2014-04-17 | 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 |
| KR20150108840A (ko) | 2012-12-21 | 2015-09-30 | 에이비티 홀딩 컴퍼니 | 세로토닌 5-ht2c 수용체 리간드로서 벤즈아제핀 및 그의 용도 |
| WO2014159067A1 (en) | 2013-03-13 | 2014-10-02 | Abt Holding Company | Thienylindole azepines as serotonin 5-ht2c receptor ligands and uses thereof |
| CN105358534A (zh) * | 2013-04-23 | 2016-02-24 | 斯洛文尼亚莱柯制药股份有限公司 | 8-氯-1-甲基-苯并[d]吖庚因的新合成方法、新的中间体及其生产方法 |
| 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 |
| CN103333111A (zh) * | 2013-06-14 | 2013-10-02 | 苏州汇和药业有限公司 | 氯卡色林盐酸盐的制备方法 |
| EP3010887A1 (en) | 2013-06-21 | 2016-04-27 | LEK Pharmaceuticals d.d. | Preparation of chiral 1-methyl-2,3,4,5-1h-benzodiazepines via asymmetric reduction of alpha-substituted styrenes |
| EP2868656A1 (en) | 2013-11-05 | 2015-05-06 | LEK Pharmaceuticals d.d. | Stabilized amorphous lorcaserin hydrochloride |
| WO2015096119A1 (zh) * | 2013-12-27 | 2015-07-02 | 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 |
| EP2924024A3 (en) | 2014-03-21 | 2016-01-20 | Medichem, S.A. | Solid forms of lorcaserin hydrochloride |
| WO2015161730A1 (zh) | 2014-04-21 | 2015-10-29 | 杭州普晒医药科技有限公司 | 一种氯卡色林共晶及其制备方法、药物组合物和用途 |
| 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 |
| US10118890B2 (en) | 2014-10-10 | 2018-11-06 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| WO2016069875A1 (en) | 2014-10-30 | 2016-05-06 | Arena Pharmaceuticals, Inc. | Compositions and methods for ceasing tobacco smoking |
| EP3210975A1 (en) | 2016-02-24 | 2017-08-30 | Enantia, S.L. | Cocrystals of lorcaserin |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| WO2022165382A1 (en) * | 2021-01-29 | 2022-08-04 | Neurawell Therapeutics | Phenylethylidenehydrazine combination therapies |
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