CN101367757A - Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide - Google Patents
Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide Download PDFInfo
- Publication number
- CN101367757A CN101367757A CNA2008102328617A CN200810232861A CN101367757A CN 101367757 A CN101367757 A CN 101367757A CN A2008102328617 A CNA2008102328617 A CN A2008102328617A CN 200810232861 A CN200810232861 A CN 200810232861A CN 101367757 A CN101367757 A CN 101367757A
- Authority
- CN
- China
- Prior art keywords
- hydroxyl
- oxo
- thick product
- recrystallization
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 49
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title claims description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 63
- 239000003513 alkali Substances 0.000 claims abstract description 27
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 239000002798 polar solvent Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- 239000000243 solution Substances 0.000 claims description 46
- 238000001953 recrystallisation Methods 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 31
- 239000003729 cation exchange resin Substances 0.000 claims description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 claims description 18
- 239000003957 anion exchange resin Substances 0.000 claims description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 18
- 235000010755 mineral Nutrition 0.000 claims description 18
- 239000011707 mineral Substances 0.000 claims description 18
- 238000006386 neutralization reaction Methods 0.000 claims description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 238000010792 warming Methods 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 150000003440 styrenes Chemical class 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 10
- 235000017550 sodium carbonate Nutrition 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- -1 alcohol compound Chemical class 0.000 claims description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- IHLAQQPQKRMGSS-BYPYZUCNSA-N 2-[(4s)-4-hydroxy-2-oxopyrrolidin-1-yl]acetamide Chemical compound NC(=O)CN1C[C@@H](O)CC1=O IHLAQQPQKRMGSS-BYPYZUCNSA-N 0.000 abstract description 33
- 238000012360 testing method Methods 0.000 abstract description 27
- 239000012043 crude product Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 229960004756 ethanol Drugs 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 229960001227 oxiracetam Drugs 0.000 description 12
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 229960000935 dehydrated alcohol Drugs 0.000 description 6
- 238000007689 inspection Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- IHLAQQPQKRMGSS-SCSAIBSYSA-N 2-[(4r)-4-hydroxy-2-oxopyrrolidin-1-yl]acetamide Chemical compound NC(=O)CN1C[C@H](O)CC1=O IHLAQQPQKRMGSS-SCSAIBSYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000003925 brain function Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | |
Mineral alkali | Yellow soda ash | Sodium bicarbonate | Salt of wormwood | Salt of wormwood |
Embodiment 4 | Embodiment 5 | Embodiment 6 | Embodiment 7 | |
Solvent | Methyl alcohol | Propyl alcohol | Butanols | Virahol |
(S)-4-halogen-3-butyric ester | |
Embodiment 4 | (S)-4-chloro-3-beta-hydroxymethyl butyrate |
Embodiment 5 | (S)-4-chloro-ethyl 3-hydroxybutanoate |
Embodiment 6 | (S)-4-bromo-3-beta-hydroxymethyl butyrate |
Embodiment 7 | (S)-4-bromo-ethyl 3-hydroxybutanoate |
Claims (14)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200810232861 CN101367757B (en) | 2008-10-13 | 2008-10-13 | Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200810232861 CN101367757B (en) | 2008-10-13 | 2008-10-13 | Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201110003973 Division CN102060744B (en) | 2008-10-13 | 2008-10-13 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN201110003499.8A Division CN102070502B (en) | 2008-10-13 | 2008-10-13 | Method for preparing (S)-4-hydroxide radical-2-oxo-1-pyrrolidine acetamide |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101367757A true CN101367757A (en) | 2009-02-18 |
CN101367757B CN101367757B (en) | 2012-09-19 |
Family
ID=40411783
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200810232861 Active CN101367757B (en) | 2008-10-13 | 2008-10-13 | Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101367757B (en) |
Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102101836A (en) * | 2009-12-16 | 2011-06-22 | 北京润德康医药技术有限公司 | New crystal form of S-oxiracetam and preparation method thereof |
CN102204904A (en) * | 2010-03-31 | 2011-10-05 | 重庆润泽医疗器械有限公司 | Application of levorotatory oxiracetamto preparation of medicaments for preventing or treating cognitive dysfunction |
CN102249974A (en) * | 2010-05-21 | 2011-11-23 | 重庆润泽医疗器械有限公司 | Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102249975A (en) * | 2010-05-21 | 2011-11-23 | 重庆润泽医疗器械有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form I and preparation method and application thereof |
CN101885697B (en) * | 2009-05-15 | 2012-04-04 | 天津药物研究院 | Preparation method of Oxiracetam |
CN102442936A (en) * | 2010-10-09 | 2012-05-09 | 重庆润泽医疗器械有限公司 | Purifying method of (S)-4-hydroxyl-2oxo-1-pyrrolidine acetamide |
CN102531989A (en) * | 2011-08-11 | 2012-07-04 | 重庆润泽医疗器械有限公司 | Purification method for (S)-oxiracetam |
CN102558013A (en) * | 2011-08-11 | 2012-07-11 | 重庆润泽医疗器械有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide crystal form II and preparation method thereof |
CN102603602A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of oxiracetam |
CN102603601A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603598A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603606A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603607A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (R)-oxiracetam |
CN102603603A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Method for preparing (S)-oxiracetam |
CN102603605A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603604A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603595A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603599A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Method for preparing (S)-oxiracetam |
CN102603597A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603596A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603594A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102617437A (en) * | 2012-04-10 | 2012-08-01 | 南京优科生物医药研究有限公司 | Novel crystal formations of levogyration oxiracetam and preparation method thereof |
CN102627596A (en) * | 2012-03-16 | 2012-08-08 | 天津景寅医药生物技术发展有限公司 | Preparation method of 4-hydroxy-2-oxo-1-pyrrolidine acetamide |
WO2013020389A1 (en) | 2011-08-11 | 2013-02-14 | 重庆润泽医疗器械有限公司 | Method for purifying levo-oxiracetam |
WO2013075459A1 (en) | 2011-11-23 | 2013-05-30 | 重庆润泽医药有限公司 | Use of levo-oxiracetam and oxiracetam in preparation of medicines for preventing or treating coma |
CN103553998A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam crystal form III |
CN103553997A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam crystal form III |
CN103554000A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | (S)-oxiracetam crystal form III, and preparation method and application thereof |
CN103599101A (en) * | 2013-11-08 | 2014-02-26 | 南京优科生物医药研究有限公司 | Application of levo-oxiracetam in preparation of medicine for treating memory and intelligence disturbance |
CN103724250A (en) * | 2011-01-21 | 2014-04-16 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam |
CN103965090A (en) * | 2014-05-31 | 2014-08-06 | 江苏诚信制药有限公司 | Refining method of oxiracetam |
CN107021901A (en) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | (S)-oxiracetam crystal form II preparation method |
CN114621128A (en) * | 2022-03-10 | 2022-06-14 | 成都百途医药科技有限公司 | Preparation method of (S) -oxiracetam |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4686296A (en) * | 1985-07-26 | 1987-08-11 | Denki Kagaku Kogyo Kabushiki Kaisha | Process for producing oxiracetam |
CH680293A5 (en) * | 1990-06-26 | 1992-07-31 | Lonza Ag | |
KR100572687B1 (en) * | 2004-05-25 | 2006-04-24 | 주식회사 알에스텍 | Process for the preparation of optically pure 4-hydroxy-2-oxo-1-pyrrolidineacetamide |
-
2008
- 2008-10-13 CN CN 200810232861 patent/CN101367757B/en active Active
Cited By (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101885697B (en) * | 2009-05-15 | 2012-04-04 | 天津药物研究院 | Preparation method of Oxiracetam |
CN102101836A (en) * | 2009-12-16 | 2011-06-22 | 北京润德康医药技术有限公司 | New crystal form of S-oxiracetam and preparation method thereof |
CN102204904A (en) * | 2010-03-31 | 2011-10-05 | 重庆润泽医疗器械有限公司 | Application of levorotatory oxiracetamto preparation of medicaments for preventing or treating cognitive dysfunction |
CN102204904B (en) * | 2010-03-31 | 2014-10-01 | 重庆润泽医药有限公司 | Application of levorotatory oxiracetamto preparation of medicaments for preventing or treating cognitive dysfunction |
CN102249975B (en) * | 2010-05-21 | 2013-12-25 | 重庆润泽医药有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form I and preparation method and application thereof |
CN102249974A (en) * | 2010-05-21 | 2011-11-23 | 重庆润泽医疗器械有限公司 | Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102249975A (en) * | 2010-05-21 | 2011-11-23 | 重庆润泽医疗器械有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form I and preparation method and application thereof |
WO2011143872A1 (en) | 2010-05-21 | 2011-11-24 | 重庆润泽医疗器械有限公司 | Crystal form of (s)-4-hydroxy-2-oxo-1-pyrrolidine acetamide, preparation method and use thereof |
WO2011143873A1 (en) | 2010-05-21 | 2011-11-24 | 重庆润泽医疗器械有限公司 | Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102249974B (en) * | 2010-05-21 | 2014-10-15 | 重庆润泽医药有限公司 | Preparation method of (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102442936A (en) * | 2010-10-09 | 2012-05-09 | 重庆润泽医疗器械有限公司 | Purifying method of (S)-4-hydroxyl-2oxo-1-pyrrolidine acetamide |
CN102603603B (en) * | 2011-01-21 | 2014-08-27 | 重庆润泽医药有限公司 | Method for preparing (S)-oxiracetam |
CN102603598A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603606A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603607A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (R)-oxiracetam |
CN102603603A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Method for preparing (S)-oxiracetam |
CN102603605A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603604A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603595A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603599A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Method for preparing (S)-oxiracetam |
CN102603597A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603596A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603594A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN103724250B (en) * | 2011-01-21 | 2016-06-29 | 温州智创科技有限公司 | A kind of preparation method of (S)-Olaxiracetam |
CN103724249B (en) * | 2011-01-21 | 2016-05-11 | 温州智创科技有限公司 | A kind of preparation method of (S)-oxiracetam |
CN103739538B (en) * | 2011-01-21 | 2016-03-16 | 温州智创科技有限公司 | A kind of preparation method of (S)-Olaxiracetam |
CN103739538A (en) * | 2011-01-21 | 2014-04-23 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam |
CN103694159B (en) * | 2011-01-21 | 2015-08-26 | 朱启东 | A kind of preparation method of (S)-Esomeprazole |
CN102603602A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of oxiracetam |
CN102603595B (en) * | 2011-01-21 | 2014-07-16 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam |
CN102603601A (en) * | 2011-01-21 | 2012-07-25 | 重庆润泽医疗器械有限公司 | Preparation method of (S)-oxiracetam |
CN102603605B (en) * | 2011-01-21 | 2014-01-22 | 重庆润泽医药有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603604B (en) * | 2011-01-21 | 2014-01-22 | 重庆润泽医药有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603597B (en) * | 2011-01-21 | 2014-01-22 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam |
CN102603598B (en) * | 2011-01-21 | 2014-07-16 | 重庆润泽医药有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN102603599B (en) * | 2011-01-21 | 2014-06-11 | 温州智创科技有限公司 | Method for preparing (S)-oxiracetam |
CN102603607B (en) * | 2011-01-21 | 2014-06-11 | 温州智创科技有限公司 | Preparation method of (R)-oxiracetam |
CN102603596B (en) * | 2011-01-21 | 2014-05-21 | 温州智创科技有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603602B (en) * | 2011-01-21 | 2014-05-21 | 温州智创科技有限公司 | Preparation method of oxiracetam |
CN103694159A (en) * | 2011-01-21 | 2014-04-02 | 重庆润泽医药有限公司 | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide |
CN103724249A (en) * | 2011-01-21 | 2014-04-16 | 重庆润泽医药有限公司 | Method for preparing (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102603594B (en) * | 2011-01-21 | 2014-04-16 | 重庆东泽医药科技发展有限公司 | Preparation method of (S)-oxiracetam |
CN103724250A (en) * | 2011-01-21 | 2014-04-16 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam |
WO2013020391A1 (en) | 2011-08-11 | 2013-02-14 | 重庆润泽医疗器械有限公司 | (s)-4-hydroxy-2-oxo-1-pyrrolidineacetamide racemate crystal form ii and preparation method therefor |
WO2013020389A1 (en) | 2011-08-11 | 2013-02-14 | 重庆润泽医疗器械有限公司 | Method for purifying levo-oxiracetam |
US9440918B2 (en) | 2011-08-11 | 2016-09-13 | Chongqing Runze Pharmaceutical Co., Ltd. | Method for purifying (S)-Oxiracetam |
CN102531989B (en) * | 2011-08-11 | 2014-02-05 | 重庆润泽医药有限公司 | Purification method for (S)-oxiracetam |
CN102558013B (en) * | 2011-08-11 | 2013-12-18 | 重庆润泽医药有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide crystal form II and preparation method thereof |
WO2013020388A1 (en) | 2011-08-11 | 2013-02-14 | 重庆润泽医疗器械有限公司 | Method for purifying (s)-oxiracetam |
CN102558013A (en) * | 2011-08-11 | 2012-07-11 | 重庆润泽医疗器械有限公司 | (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide crystal form II and preparation method thereof |
CN102531989A (en) * | 2011-08-11 | 2012-07-04 | 重庆润泽医疗器械有限公司 | Purification method for (S)-oxiracetam |
WO2013075459A1 (en) | 2011-11-23 | 2013-05-30 | 重庆润泽医药有限公司 | Use of levo-oxiracetam and oxiracetam in preparation of medicines for preventing or treating coma |
CN102627596A (en) * | 2012-03-16 | 2012-08-08 | 天津景寅医药生物技术发展有限公司 | Preparation method of 4-hydroxy-2-oxo-1-pyrrolidine acetamide |
CN102627596B (en) * | 2012-03-16 | 2016-01-27 | 天津景寅医药生物技术发展有限公司 | A kind of preparation method of Esomeprazole |
CN102617437A (en) * | 2012-04-10 | 2012-08-01 | 南京优科生物医药研究有限公司 | Novel crystal formations of levogyration oxiracetam and preparation method thereof |
CN102617437B (en) * | 2012-04-10 | 2014-10-29 | 南京优科生物医药研究有限公司 | Novel crystal formations of levogyration oxiracetam and preparation method thereof |
WO2015067130A1 (en) | 2013-11-06 | 2015-05-14 | 重庆润泽医药有限公司 | (s)-oxiracetam crystal form iii, preparation method therefor, and application thereof |
CN103553997B (en) * | 2013-11-06 | 2015-11-25 | 温州智创科技有限公司 | The preparation method of a kind of (S)-Oxiracetam crystal form III |
CN103553998B (en) * | 2013-11-06 | 2015-11-25 | 温州智创科技有限公司 | (S) preparation method of-Oxiracetam crystal form III |
CN103554000B (en) * | 2013-11-06 | 2015-03-11 | 重庆润泽医药有限公司 | (S)-oxiracetam crystal form III, and preparation method and application thereof |
CN103553998A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam crystal form III |
CN103553997A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | Preparation method of (S)-oxiracetam crystal form III |
CN103554000A (en) * | 2013-11-06 | 2014-02-05 | 重庆润泽医药有限公司 | (S)-oxiracetam crystal form III, and preparation method and application thereof |
US9670156B2 (en) | 2013-11-06 | 2017-06-06 | Chongqing Ruzer Pharmaceutical Company Limited | Crystal form III of (S)-oxiracetam, preparation method and use thereof |
CN103599101A (en) * | 2013-11-08 | 2014-02-26 | 南京优科生物医药研究有限公司 | Application of levo-oxiracetam in preparation of medicine for treating memory and intelligence disturbance |
CN103965090B (en) * | 2014-05-31 | 2015-11-18 | 江苏诚信药业有限公司 | A kind of process for purification of oxiracetam |
CN103965090A (en) * | 2014-05-31 | 2014-08-06 | 江苏诚信制药有限公司 | Refining method of oxiracetam |
CN107021901A (en) * | 2016-01-29 | 2017-08-08 | 重庆润泽医药有限公司 | (S)-oxiracetam crystal form II preparation method |
CN114621128A (en) * | 2022-03-10 | 2022-06-14 | 成都百途医药科技有限公司 | Preparation method of (S) -oxiracetam |
Also Published As
Publication number | Publication date |
---|---|
CN101367757B (en) | 2012-09-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101367757B (en) | Preparation method for (S)-4-hydroxyl-2-oxo-1-pyrrolidine ethanamide | |
CN102603607A (en) | Preparation method of (R)-oxiracetam | |
EP2743259B1 (en) | Method for purifying (s)-oxiracetam | |
CN102659702B (en) | Purifying process of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) | |
CN102060744B (en) | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide | |
EP2743258B1 (en) | Method for purifying levo-oxiracetam | |
CN102690222A (en) | Preparation method of (R,S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide | |
CN102603603B (en) | Method for preparing (S)-oxiracetam | |
CN102070502B (en) | Method for preparing (S)-4-hydroxide radical-2-oxo-1-pyrrolidine acetamide | |
CN102702051B (en) | A kind of preparation method of cilastatin sodium | |
CN102603595B (en) | Preparation method of (S)-oxiracetam | |
CN102603594A (en) | Preparation method of (S)-oxiracetam | |
WO2013159285A1 (en) | Method for preparing (s)-oxiracetam | |
CN105294686A (en) | Preparation method of riociguat | |
CN103724250B (en) | A kind of preparation method of (S)-Olaxiracetam | |
CN102603596B (en) | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidine acetamide | |
CN103724249B (en) | A kind of preparation method of (S)-oxiracetam | |
CN102603605B (en) | Preparation method of (S)-4-hydroxy-2-oxo-1-pyrrolidineacetamide | |
WO2013159283A1 (en) | Method for preparing (s)-oxiracetam | |
CN102603599B (en) | Method for preparing (S)-oxiracetam | |
CN106631909B (en) | A kind of preparation method of gamatine hydrochloride | |
CN105906513A (en) | Preparation method of trifluoroethylamine | |
CN104923165A (en) | Derivative based on aromatic pyridone molecular skeleton, and application thereof in preparing mercury capturing agent | |
CN102924308A (en) | Method for preparing rosolic acid complexing agent | |
CN102603602B (en) | Preparation method of oxiracetam |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C53 | Correction of patent for invention or patent application | ||
C56 | Change in the name or address of the patentee |
Owner name: CHONGQING RUNZE PHARMACEUTICAL CO., LTD. Free format text: FORMER NAME: CHONGQING RUNZE MEDICAL INSTRUMENTS LTD. |
|
CB03 | Change of inventor or designer information |
Inventor after: Chen Yuying Inventor after: Hao Lina Inventor after: Jie Yunfeng Inventor after: Ye Lei Inventor after: Rong Zuyuan Inventor before: Chen Yuying Inventor before: Li Kun Inventor before: Rong Zuyuan Inventor before: Ye Lei Inventor before: Ping Yuan Inventor before: Yu Yuanyuan |
|
COR | Change of bibliographic data |
Free format text: CORRECT: INVENTOR; FROM: CHEN YUYING LI KUN RONG ZUYUAN YE LEI PING YUAN YU YUANYUAN TO: CHEN YUYING HAO LINA JIE YUNFENG YE LEI RONG ZUYUAN |
|
CP03 | Change of name, title or address |
Address after: 400042 Chongqing city Yubei District Qinye Road No. 9 Patentee after: Chongqing Runze Pharmaceutical Co., Ltd. Address before: 400030 Chongqing city Shapingba District Yubei Road No. 50 of No. 13-15-6A Patentee before: Chongqing Runze Medical Instruments Ltd. |
|
ASS | Succession or assignment of patent right |
Owner name: CHONGQING DONGZE PHARMACEUTICAL TECHNOLOGY DEVELOP Free format text: FORMER OWNER: CHONGQING RUNZE PHARMACEUTICAL CO., LTD. Effective date: 20140305 |
|
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 400042 YUBEI, CHONGQING TO: 400030 SHAPINGBA, CHONGQING |
|
TR01 | Transfer of patent right |
Effective date of registration: 20140305 Address after: 400030 Chongqing city Shapingba District Yubei Road No. 50 of No. 13-15-6A Patentee after: DONGZE PHARMACEUTICAL SCIENCE AND TECHNOLOGY CO., LTD. Address before: 400042 Chongqing city Yubei District Qinye Road No. 9 Patentee before: Chongqing Runze Pharmaceutical Co., Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170823 Address after: 400042 Chongqing city Yubei District Qinye Road No. 9 Patentee after: Chongqing Runze Pharmaceutical Co., Ltd. Address before: 400030 Chongqing city Shapingba District Yubei Road No. 50 of No. 13-15-6A Patentee before: DONGZE PHARMACEUTICAL SCIENCE AND TECHNOLOGY CO., LTD. |