CA2888877C - A process for the preparation of pregabalin - Google Patents
A process for the preparation of pregabalin Download PDFInfo
- Publication number
- CA2888877C CA2888877C CA2888877A CA2888877A CA2888877C CA 2888877 C CA2888877 C CA 2888877C CA 2888877 A CA2888877 A CA 2888877A CA 2888877 A CA2888877 A CA 2888877A CA 2888877 C CA2888877 C CA 2888877C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- methyl
- acid
- cyano
- ester
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/002—Nitriles (-CN)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Toxicology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3228MU2012 | 2012-11-07 | ||
| IN3228/MUM/2012 | 2012-11-07 | ||
| PCT/IB2013/002435 WO2014072785A2 (en) | 2012-11-07 | 2013-11-04 | A process for the preparation of pregabalin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2888877A1 CA2888877A1 (en) | 2014-05-15 |
| CA2888877C true CA2888877C (en) | 2021-07-27 |
Family
ID=50685262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2888877A Active CA2888877C (en) | 2012-11-07 | 2013-11-04 | A process for the preparation of pregabalin |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10023885B2 (enExample) |
| EP (1) | EP2916832B1 (enExample) |
| JP (1) | JP6482465B2 (enExample) |
| CA (1) | CA2888877C (enExample) |
| WO (1) | WO2014072785A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481708A (zh) * | 2015-11-26 | 2016-04-13 | 太仓运通生物化工有限公司 | 一种以氰乙酸甲酯、异戊醛为原料合成普瑞巴林的方法 |
| CN105463037A (zh) * | 2015-11-26 | 2016-04-06 | 太仓运通生物化工有限公司 | 一种以异丁基丁二腈为中间体合成普瑞巴林的方法 |
| CN108424900B (zh) * | 2018-02-09 | 2020-11-03 | 浙江工业大学 | 一种腈水解酶突变体及其构建方法和应用 |
| CN110174467B (zh) * | 2018-10-25 | 2022-04-08 | 武汉武药制药有限公司 | 一种高效液相色谱法分析分离2,4-二氰基-3-异丁基戊二酰胺的方法 |
| WO2020183376A1 (en) * | 2019-03-11 | 2020-09-17 | Hikal Limited | Greener and economic process for preparation of pregabalin |
| WO2021105742A1 (en) * | 2019-11-26 | 2021-06-03 | Hikal Limited | An improved process for the preparation of pregabalin |
| CN111004138A (zh) * | 2019-12-12 | 2020-04-14 | 南京恒道医药科技有限公司 | 一种左乙拉西坦关键中间体s-2-氨基丁酸甲酯的绿色生产方法及其装置 |
| CN114164197B (zh) * | 2020-01-13 | 2023-08-18 | 浙江工业大学 | 一种热稳定性和活力提高的腈水解酶突变体及其应用 |
| JP7436689B2 (ja) * | 2020-02-14 | 2024-02-22 | カウンシル オブ サイエンティフィック アンド インダストリアル リサーチ | γ－アミノ酪酸及びその類似体の製造方法 |
| CN114425386B (zh) * | 2020-10-14 | 2023-08-29 | 中国石油化工股份有限公司 | 脂肪酸甲酯乙氧基化催化剂 |
| CN112521299B (zh) * | 2020-12-15 | 2022-08-16 | 内蒙古永太化学有限公司 | 一种普瑞巴林中间体的制备方法 |
| CN112941122B (zh) * | 2021-02-23 | 2022-12-09 | 浙江工业大学 | 一种(s)-3-氰基-5-甲基己酸的制备方法 |
| CN113149823B (zh) * | 2021-03-29 | 2023-12-08 | 上海青平药业有限公司 | 一种2-r1戊酸的制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197819B1 (en) | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| US5616793A (en) | 1995-06-02 | 1997-04-01 | Warner-Lambert Company | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| US5637767A (en) | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| FR2856922B1 (fr) | 2003-07-01 | 2005-08-12 | Oreal | Composition tinctoriale comprenant au moins une base d'oxydation, le 2-chloro 6-methyl 3-aminophenol et la 3-methyl 1-phenyl 5-pyrazolone |
| UA82292C2 (uk) * | 2004-04-14 | 2008-03-25 | Пфайзер Продактс Инк. | Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти) |
| WO2007035789A1 (en) | 2005-09-19 | 2007-03-29 | Teva Pharmaceutical Industries Ltd. | Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the new synthesis of (s)-pregabalin |
| WO2007139933A2 (en) | 2006-05-24 | 2007-12-06 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof |
| WO2007143113A2 (en) * | 2006-05-31 | 2007-12-13 | Teva Pharmaceutical Industries Ltd. | The use of enzymatic resolution for the preparation of intermediates of pregabalin |
| WO2008062460A2 (en) | 2006-10-06 | 2008-05-29 | Cadila Healthcare Limited | Crystalline forms of pregabalin |
| TW200846308A (en) | 2007-03-22 | 2008-12-01 | Teva Pharma | Synthesis of (s)-(+)-3-(aminomethyl)-5-methyl hexanoic acid |
| WO2008137512A2 (en) | 2007-05-03 | 2008-11-13 | Dr. Reddy's Laboratories Ltd. | Process for preparing pregabalin via hofmann reaction and crystalline form thereof |
| WO2008138874A1 (en) | 2007-05-09 | 2008-11-20 | Chemo Ibérica, S.A. | Process for preparing (s)-pregabalin by optical resolution of racemic pregabalin |
| US8168828B2 (en) | 2007-06-25 | 2012-05-01 | Msn Laboratories, Limited | Process for the preparation of pregabalin |
| WO2009044409A2 (en) | 2007-10-01 | 2009-04-09 | Natco Pharma Limited | Novel resolution process for pregabalin |
| ITMI20072262A1 (it) | 2007-12-03 | 2009-06-04 | Dipharma Francis Srl | Procedimento per la preparazione di acido (s)(+)-3-(amminometil)-5-metilesanoico |
| EP2225199A2 (en) | 2007-12-18 | 2010-09-08 | Watson Pharma Private Limited | Improved process for the preparation of (s)-pregabalin |
| EP2222630A1 (en) | 2007-12-26 | 2010-09-01 | Generics (UK) Limited | Processes to pregabalin |
| US20110144383A1 (en) | 2008-02-18 | 2011-06-16 | Matrix Laboratories Limited | Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid |
| AU2009233536A1 (en) | 2008-04-04 | 2009-10-08 | Generics [Uk] Limited | Novel process |
| WO2011141923A2 (en) * | 2010-05-14 | 2011-11-17 | Lupin Limited | Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin |
-
2013
- 2013-11-04 JP JP2015540226A patent/JP6482465B2/ja active Active
- 2013-11-04 WO PCT/IB2013/002435 patent/WO2014072785A2/en not_active Ceased
- 2013-11-04 US US14/434,658 patent/US10023885B2/en active Active
- 2013-11-04 EP EP13853048.0A patent/EP2916832B1/en not_active Not-in-force
- 2013-11-04 CA CA2888877A patent/CA2888877C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015535003A (ja) | 2015-12-07 |
| EP2916832A4 (en) | 2016-06-29 |
| US20150344919A1 (en) | 2015-12-03 |
| US10023885B2 (en) | 2018-07-17 |
| CA2888877A1 (en) | 2014-05-15 |
| EP2916832B1 (en) | 2019-01-16 |
| EP2916832A2 (en) | 2015-09-16 |
| JP6482465B2 (ja) | 2019-03-13 |
| WO2014072785A2 (en) | 2014-05-15 |
| WO2014072785A8 (en) | 2014-09-18 |
| WO2014072785A3 (en) | 2014-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20181030 |
|
| H11 | Ip right ceased following rejected request for revival |
Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED Effective date: 20250506 |