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.)
- Granted
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 (enExample) | 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 (enExample) |
| EP (4) | EP2332921B1 (enExample) |
| JP (4) | JP4920409B2 (enExample) |
| KR (1) | KR101215107B1 (enExample) |
| AU (1) | AU2004267016B2 (enExample) |
| BR (1) | BRPI0411613B8 (enExample) |
| CA (1) | CA2529401C (enExample) |
| CY (1) | CY1117619T1 (enExample) |
| DK (1) | DK2332921T3 (enExample) |
| EA (1) | EA016485B1 (enExample) |
| ES (1) | ES2571220T3 (enExample) |
| HU (1) | HUE028976T2 (enExample) |
| IL (1) | IL172331A (enExample) |
| MX (1) | MXPA05013364A (enExample) |
| PL (1) | PL2332921T3 (enExample) |
| SI (1) | SI2332921T1 (enExample) |
| WO (1) | WO2005019179A2 (enExample) |
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 |
| EP2332921B1 (en) | 2003-06-17 | 2016-03-02 | Arena Pharmaceuticals, Inc. | 8-Chloro-1 -methyl-2,3,4,5-tetrahydro-1 H-3benzazapine Hydrochloride |
| 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 |
| NZ589756A (en) * | 2004-12-21 | 2012-05-25 | Arena Pharm Inc | Method for the preparation of crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| WO2006071740A2 (en) | 2004-12-23 | 2006-07-06 | Arena Pharmaceuticals, Inc. | 5ht2c receptor modulator compositions and methods of use |
| EP1926712B1 (en) | 2005-09-01 | 2009-07-29 | Eli Lilly And Company | 6-substituted 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists |
| DE602006008323D1 (de) | 2005-09-01 | 2009-09-17 | Lilly Co Eli | 6-substituierte- 2,3,4,5-tetrahydro-1h-benzoädüazepine als 5-ht2c-rezeptoragonisten |
| EP1924578B1 (en) | 2005-09-01 | 2013-11-06 | Eli Lilly And Company | 6-N-LINKED HETEROCYCLE-SUBSTITUTED 2,3,4,5-TETRAHYDRO-1H-BENZO[d]AZEPINES AS 5-HT2C RECEPTOR AGONISTS |
| JP5155864B2 (ja) | 2005-09-01 | 2013-03-06 | 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−アリールアルキルアミノ−２，３，４，５−テトラヒドロ−１Ｈ−ベンゾ［ｄ］アゼピン |
| EP1981337B1 (en) | 2006-01-19 | 2015-09-02 | Athersys, Inc. | Thiophenyl azepines as serotonin 5-ht2c receptor ligands and uses thereof |
| CN101466684B (zh) | 2006-04-03 | 2012-06-20 | 艾尼纳制药公司 | 8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的制备工艺和其相关中间体 |
| 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 |
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| 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 |
| WO2009051747A1 (en) * | 2007-10-15 | 2009-04-23 | 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 |
| EP2288585A1 (en) * | 2008-03-04 | 2011-03-02 | 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 |
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| EA021079B1 (ru) | 2009-06-15 | 2015-03-31 | Такеда Фармасьютикал Компани Лимитед | Производные пиразинооксазепина |
| EP2443080A2 (en) | 2009-06-18 | 2012-04-25 | Arena Pharmaceuticals, Inc. | Process for the preparation of 5-ht2c receptor agonists |
| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| WO2012030939A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| EP3485878A1 (en) * | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| EP2611433A2 (en) | 2010-09-01 | 2013-07-10 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-ht2c agonists |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| WO2012030953A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| IN2013DN02552A (enExample) * | 2010-09-01 | 2015-08-07 | Arena Pharm Inc | |
| JP2015534563A (ja) | 2012-10-09 | 2015-12-03 | 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 | 体重管理の方法 |
| WO2014060575A2 (en) | 2012-10-19 | 2014-04-24 | Medichem S.A. | Process for the enantioselective synthesis of a tetrahydrobenzazepine compound |
| BR112015014674A2 (pt) | 2012-12-21 | 2017-07-11 | Abt Holding Co | benzazepinas como ligantes do receptor de serotonina 5-ht2c e usos das mesmas |
| US9309262B2 (en) | 2013-03-13 | 2016-04-12 | Abt Holding Company | Thienylindole azepines as serotonin 5-HT2C receptor ligands and uses thereof |
| WO2014173928A1 (en) * | 2013-04-23 | 2014-10-30 | Lek Pharmaceuticals D.D. | Novel synthetic process to 8-chloro-1-methyl-benzo[d]azepine, novel intermediates and the production thereof |
| 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 |
| US9981912B2 (en) | 2014-04-21 | 2018-05-29 | Hangzhou Pushai Pharmaceutical Technology Co., Ltd. | Cocrystal of lorcaserin, preparation methods, pharmaceutical compositions and uses thereof |
| 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 |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | 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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2004
- 2004-06-16 EP EP10010301.9A patent/EP2332921B1/en not_active Expired - Lifetime
- 2004-06-16 DK DK10010301.9T patent/DK2332921T3/en active
- 2004-06-16 EA EA200600049A patent/EA016485B1/ru not_active IP Right Cessation
- 2004-06-16 BR BRPI0411613A patent/BRPI0411613B8/pt not_active IP Right Cessation
- 2004-06-16 MX MXPA05013364A patent/MXPA05013364A/es active IP Right Grant
- 2004-06-16 HU HUE10010301A patent/HUE028976T2/en unknown
- 2004-06-16 EP EP09012098.1A patent/EP2189448B1/en not_active Expired - Lifetime
- 2004-06-16 AU AU2004267016A patent/AU2004267016B2/en not_active Expired
- 2004-06-16 CA CA2529401A patent/CA2529401C/en not_active Expired - Lifetime
- 2004-06-16 WO PCT/US2004/019279 patent/WO2005019179A2/en not_active Ceased
- 2004-06-16 SI SI200432322A patent/SI2332921T1/sl unknown
- 2004-06-16 JP JP2006517336A patent/JP4920409B2/ja not_active Expired - Fee Related
- 2004-06-16 EP EP04801895A patent/EP1636191A2/en not_active Withdrawn
- 2004-06-16 US US10/560,953 patent/US8367657B2/en not_active Expired - Fee Related
- 2004-06-16 ES ES10010301T patent/ES2571220T3/es not_active Expired - Lifetime
- 2004-06-16 EP EP10010295A patent/EP2332919A3/en not_active Withdrawn
- 2004-06-16 PL PL10010301T patent/PL2332921T3/pl unknown
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2005
- 2005-12-02 IL IL172331A patent/IL172331A/en active IP Right Grant
- 2005-12-16 KR KR1020057024265A patent/KR101215107B1/ko not_active Expired - Lifetime
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2011
- 2011-03-07 JP JP2011049671A patent/JP5421311B2/ja not_active Expired - Fee Related
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2012
- 2012-03-06 JP JP2012049640A patent/JP5667593B2/ja not_active Expired - Fee Related
- 2012-09-14 US US13/619,788 patent/US9102627B2/en not_active Expired - Lifetime
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2014
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2015
- 2015-07-27 US US14/810,063 patent/US20160185729A1/en not_active Abandoned
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2016
- 2016-05-18 CY CY20161100427T patent/CY1117619T1/el unknown