CN102249975B - (s)-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅰ及其制备方法和用途 - Google Patents
(s)-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅰ及其制备方法和用途 Download PDFInfo
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- CN102249975B CN102249975B CN2010105011201A CN201010501120A CN102249975B CN 102249975 B CN102249975 B CN 102249975B CN 2010105011201 A CN2010105011201 A CN 2010105011201A CN 201010501120 A CN201010501120 A CN 201010501120A CN 102249975 B CN102249975 B CN 102249975B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | (S)-4-氯-3-羟基丁酸乙酯用量 | 甘氨酰胺盐酸盐用量 | 乙醇用量 | 碳酸氢钠用量 | 精制及所用乙醇重量与粗品重量关系 | 一次结晶中的物料(重量份数比) | 一次结晶温度、搅拌时间 | 二次结晶 |
3 | 97.7g | 64.8g | 500ml | 98.5g | 不进行 | 粗品与水1:0.4,水与丙酮1:20 | -10~-5℃;2h | 不进行 |
4 | 78.2g | 51.8g | 400ml | 78.8g | 不进行 | 粗品与水1:0.7,水与丙酮1:5 | 8~10℃;12h | 与本实施例一次结晶各参数同 |
5 | 156.4g | 103.6g | 800ml | 157.6g | 进行,乙醇为粗品重量的8倍 | 粗品与水1:0.5,水与丙酮1:10 | 0~5℃;5h | 不进行 |
6 | 4.9Kg | 3.3Kg | 25L | 4.9Kg | 进行,乙醇为粗品重量的2倍 | 粗品与水1:0.6,水与丙酮1:8 | 2~6℃;3h | 不进行 |
Claims (14)
Priority Applications (1)
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CN2010105011201A CN102249975B (zh) | 2010-05-21 | 2010-10-09 | (s)-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅰ及其制备方法和用途 |
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CN201010179812 | 2010-05-21 | ||
CN201010179812.9 | 2010-05-21 | ||
CN2010105011201A CN102249975B (zh) | 2010-05-21 | 2010-10-09 | (s)-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅰ及其制备方法和用途 |
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CN102249975A CN102249975A (zh) | 2011-11-23 |
CN102249975B true CN102249975B (zh) | 2013-12-25 |
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CN2010105011201A Active CN102249975B (zh) | 2010-05-21 | 2010-10-09 | (s)-4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅰ及其制备方法和用途 |
Country Status (5)
Country | Link |
---|---|
US (1) | US9238622B2 (zh) |
EP (1) | EP2573070B1 (zh) |
CN (1) | CN102249975B (zh) |
ES (1) | ES2587978T3 (zh) |
WO (1) | WO2011143872A1 (zh) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9238622B2 (en) | 2010-05-21 | 2016-01-19 | Chongqing Runze Pharmaceutical Co., Ltd. | Crystal form I of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide, preparing method and use thereof |
CN102558013B (zh) * | 2011-08-11 | 2013-12-18 | 重庆润泽医药有限公司 | (s)- 4-羟基-2-氧代-1-吡咯烷乙酰胺晶型ⅱ及其制备方法 |
CN102531988A (zh) * | 2011-08-11 | 2012-07-04 | 重庆润泽医疗器械有限公司 | 一种左旋奥拉西坦的纯化方法 |
CN102531989B (zh) | 2011-08-11 | 2014-02-05 | 重庆润泽医药有限公司 | 一种(s)-奥拉西坦的纯化方法 |
CN102670497A (zh) * | 2012-05-31 | 2012-09-19 | 北京阜康仁生物制药科技有限公司 | 一种稳定的s-奥拉西坦注射用制剂及其制备方法 |
CN103494790B (zh) * | 2013-09-30 | 2014-11-26 | 石药集团欧意药业有限公司 | 一种奥拉西坦胶囊及其制备方法 |
CN103554000B (zh) | 2013-11-06 | 2015-03-11 | 重庆润泽医药有限公司 | (s)-奥拉西坦晶型iii及其制备方法和用途 |
CN105125515B (zh) * | 2013-12-06 | 2018-07-13 | 重庆润泽医药有限公司 | 一种左旋奥拉西坦片剂及其制备方法 |
CN106511305A (zh) * | 2015-09-11 | 2017-03-22 | 重庆润泽医药有限公司 | 一种收率高的左旋奥拉西坦缓释胶囊及其制备方法 |
CN106511311A (zh) * | 2015-09-11 | 2017-03-22 | 重庆润泽医药有限公司 | 一种颗粒流动性好的左旋奥拉西坦缓释胶囊及其制备方法 |
CN106902090A (zh) * | 2015-12-17 | 2017-06-30 | 重庆润泽医药有限公司 | 一种口感好的(s)-4-羟基-2氧代-1-吡咯烷乙酰胺泡腾片及其制备方法 |
CN106890157A (zh) * | 2015-12-17 | 2017-06-27 | 重庆润泽医药有限公司 | 一种不易吸湿的左旋奥拉西坦泡腾片及其制备方法 |
CN107011231A (zh) * | 2016-01-29 | 2017-08-04 | 重庆润泽医药有限公司 | S-奥拉西坦晶型i的制备方法 |
CN107021903A (zh) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | 一种左旋奥拉西坦晶型i的制备方法 |
CN107021913A (zh) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | 一种制备左旋奥拉西坦晶型i的方法 |
CN107021912A (zh) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | 研磨制备左旋奥拉西坦晶型i的方法 |
CN107011230A (zh) * | 2016-01-29 | 2017-08-04 | 重庆润泽医药有限公司 | pH法制备左旋奥拉西坦晶型II的方法 |
CN107011232A (zh) * | 2016-01-29 | 2017-08-04 | 重庆润泽医药有限公司 | 球磨制备左旋奥拉西坦晶型ii的方法 |
CN107021902A (zh) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | 一种左旋奥拉西坦晶型i的制备方法 |
CN107011233A (zh) * | 2016-01-29 | 2017-08-04 | 重庆润泽医药有限公司 | 毛细管法制备左旋奥拉西坦晶型i的方法 |
CN107625747A (zh) * | 2016-07-13 | 2018-01-26 | 重庆润泽医药有限公司 | 一种(s)‑4‑羟基‑2氧代‑1‑吡咯烷乙酰胺缓释胶囊及其制备方法 |
CN107661315A (zh) * | 2016-07-28 | 2018-02-06 | 重庆润泽医药有限公司 | 一种缓释释放的左旋奥拉西坦胶囊及其制备方法 |
CN107661314A (zh) * | 2016-07-28 | 2018-02-06 | 重庆润泽医药有限公司 | 一种稳定性好的(s)‑4‑羟基‑2氧代‑1‑吡咯烷乙酰胺缓释胶囊及其制备方法 |
KR20190051059A (ko) * | 2016-10-24 | 2019-05-14 | 충칭 룬즈 파마슈티컬 컴퍼니 리미티드. | 덱스트랄 옥시라세탐의 결정형 ⅱ, 이의 제조 방법 및 이의 용도 |
CN108567749A (zh) * | 2017-03-14 | 2018-09-25 | 重庆润泽医药有限公司 | 一种适合儿童服用的左旋奥拉西坦口服制剂及其制备方法 |
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CN1956953A (zh) * | 2004-05-25 | 2007-05-02 | 安国药品株式会社 | 旋光纯4-羟基-2-氧化-1-吡咯烷乙酰胺的制备方法 |
CN101367757A (zh) * | 2008-10-13 | 2009-02-18 | 重庆润泽医疗器械有限公司 | 一种(s)-4-羟基-2-氧代-1-吡咯烷乙酰胺的制备方法 |
CN101575309A (zh) * | 2009-04-28 | 2009-11-11 | 中国医药集团总公司四川抗菌素工业研究所 | 合成(s)-奥拉西坦的方法 |
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IT1075564B (it) * | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
EP0223328B1 (en) | 1985-07-26 | 1992-01-29 | Denki Kagaku Kogyo Kabushiki Kaisha | Process for producing oxiracetam |
CN102101836A (zh) | 2009-12-16 | 2011-06-22 | 北京润德康医药技术有限公司 | S-奥拉西坦新晶型及其制备方法 |
US9238622B2 (en) | 2010-05-21 | 2016-01-19 | Chongqing Runze Pharmaceutical Co., Ltd. | Crystal form I of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide, preparing method and use thereof |
CN102249974B (zh) | 2010-05-21 | 2014-10-15 | 重庆润泽医药有限公司 | 一种(s)-4-羟基-2-氧代-1-吡咯烷乙酰胺的制备方法 |
CN102050774B (zh) | 2010-12-02 | 2012-01-11 | 王明 | 一种奥拉西坦化合物及其新方法 |
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2010
- 2010-09-08 US US13/581,821 patent/US9238622B2/en active Active
- 2010-09-08 WO PCT/CN2010/076721 patent/WO2011143872A1/zh active Application Filing
- 2010-09-08 EP EP10851629.5A patent/EP2573070B1/en active Active
- 2010-09-08 ES ES10851629.5T patent/ES2587978T3/es active Active
- 2010-10-09 CN CN2010105011201A patent/CN102249975B/zh active Active
Patent Citations (3)
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CN1956953A (zh) * | 2004-05-25 | 2007-05-02 | 安国药品株式会社 | 旋光纯4-羟基-2-氧化-1-吡咯烷乙酰胺的制备方法 |
CN101367757A (zh) * | 2008-10-13 | 2009-02-18 | 重庆润泽医疗器械有限公司 | 一种(s)-4-羟基-2-氧代-1-吡咯烷乙酰胺的制备方法 |
CN101575309A (zh) * | 2009-04-28 | 2009-11-11 | 中国医药集团总公司四川抗菌素工业研究所 | 合成(s)-奥拉西坦的方法 |
Also Published As
Publication number | Publication date |
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US20130059900A1 (en) | 2013-03-07 |
ES2587978T3 (es) | 2016-10-28 |
EP2573070B1 (en) | 2016-06-01 |
US9238622B2 (en) | 2016-01-19 |
WO2011143872A9 (zh) | 2013-03-21 |
WO2011143872A1 (zh) | 2011-11-24 |
CN102249975A (zh) | 2011-11-23 |
EP2573070A1 (en) | 2013-03-27 |
EP2573070A4 (en) | 2013-10-09 |
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