WO2009004643A3 - An improved process for preparation of (s)-pregabalin and intermediates thereof - Google Patents

An improved process for preparation of (s)-pregabalin and intermediates thereof Download PDF

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Publication number
WO2009004643A3
WO2009004643A3 PCT/IN2008/000287 IN2008000287W WO2009004643A3 WO 2009004643 A3 WO2009004643 A3 WO 2009004643A3 IN 2008000287 W IN2008000287 W IN 2008000287W WO 2009004643 A3 WO2009004643 A3 WO 2009004643A3
Authority
WO
WIPO (PCT)
Prior art keywords
pregabalin
preparation
intermediates
improved process
relates
Prior art date
Application number
PCT/IN2008/000287
Other languages
French (fr)
Other versions
WO2009004643A2 (en
Inventor
Thirupathi Rao Tippanu
Shriprakash Dhar Dwivedi
Ketan Ambalal Doshi
Rakesh Brijnandan Sahay
Rushikesh Udaykumar Roy
Original Assignee
Cadila Healthcare Ltd
Thirupathi Rao Tippanu
Shriprakash Dhar Dwivedi
Ketan Ambalal Doshi
Rakesh Brijnandan Sahay
Rushikesh Udaykumar Roy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cadila Healthcare Ltd, Thirupathi Rao Tippanu, Shriprakash Dhar Dwivedi, Ketan Ambalal Doshi, Rakesh Brijnandan Sahay, Rushikesh Udaykumar Roy filed Critical Cadila Healthcare Ltd
Publication of WO2009004643A2 publication Critical patent/WO2009004643A2/en
Publication of WO2009004643A3 publication Critical patent/WO2009004643A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • 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
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • 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
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to an improved process for the preparation of (S)- Pregabalin of formula (I) and its intermediates thereof. Particularly, the present invention relates to the process for the preparation (S)-Pregabalin having chiral purity not less than 99.0% by area percentage of HPLC. Further, the present invention relates to the process for the preparation of (S)-Pregabalin having low level of impurities, determined by area percentage of HPLC.
PCT/IN2008/000287 2007-05-08 2008-05-08 An improved process for preparation of (s)-pregabalin and intermediates thereof WO2009004643A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN877MU2007 2007-05-08
IN877/MUM/2007 2007-05-08

Publications (2)

Publication Number Publication Date
WO2009004643A2 WO2009004643A2 (en) 2009-01-08
WO2009004643A3 true WO2009004643A3 (en) 2009-04-30

Family

ID=40039648

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000287 WO2009004643A2 (en) 2007-05-08 2008-05-08 An improved process for preparation of (s)-pregabalin and intermediates thereof

Country Status (1)

Country Link
WO (1) WO2009004643A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102115439B (en) * 2009-12-31 2015-09-16 浙江华海药业股份有限公司 A kind of preparation method of pregabalin intermediate 3-isobutylglutaric acid
WO2012093411A2 (en) * 2011-01-07 2012-07-12 Dr Braja Sundar Pradhan Process for the preparation of r-(-)-3- (carbamoylmethyl)-5-methylhexanoic acid and the intermediates
WO2012142662A1 (en) * 2011-04-21 2012-10-26 Garvan Institute Of Medical Research Modified variable domain molecules and methods for producing and using them b
CN102964263B (en) * 2012-11-29 2014-12-03 太仓市茜泾化工有限公司 Process for preparing (+/-)-3-(Carbamoymethyl)-5-methylhexanoic acid
CN103980144B (en) * 2014-05-16 2018-08-17 浙江华海药业股份有限公司 A kind of using method of pregabalin intermediate mother liquor
CN105175276A (en) * 2015-07-25 2015-12-23 安徽东凯生物科技有限公司 Synthetic method for optically pure(R)-3-carbamyl methyl-5-methyl caproic acid
CN105348123A (en) * 2015-11-26 2016-02-24 太仓运通生物化工有限公司 Method for synthesizing Pregabalin by taking gamma-isobutylglutaric anhydride as intermediate
CN108912004B (en) * 2018-08-01 2021-05-07 宏冠生物药业有限公司 Synthetic method of pregabalin intermediate
CN109320430A (en) * 2018-09-25 2019-02-12 廊坊市泽康医药科技有限公司 A kind of pregabalin intermediate synthetic method
CN117192003A (en) * 2023-09-08 2023-12-08 山东则正医药技术有限公司 Pretreatment method of pregabalin sustained release tablet and detection method of pregabalin and/or related substances

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5629447A (en) * 1995-06-02 1997-05-13 Warner-Lambert Company Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid
WO2006122255A1 (en) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Pregabalin free of isobutylglutaric acid and a process for preparation thereof
US20070043241A1 (en) * 2005-05-10 2007-02-22 Lilach Hedvati Optical resolution of 3-carbamoylmethyl-5-methylhexanoic acid
WO2007127309A2 (en) * 2006-04-24 2007-11-08 Teva Pharmaceutical Industries Ltd. Processes for the synthesis of 3-isobutylglutaric acid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5629447A (en) * 1995-06-02 1997-05-13 Warner-Lambert Company Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid
WO2006122255A1 (en) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Pregabalin free of isobutylglutaric acid and a process for preparation thereof
US20070043241A1 (en) * 2005-05-10 2007-02-22 Lilach Hedvati Optical resolution of 3-carbamoylmethyl-5-methylhexanoic acid
WO2007127309A2 (en) * 2006-04-24 2007-11-08 Teva Pharmaceutical Industries Ltd. Processes for the synthesis of 3-isobutylglutaric acid

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOOTS M R ET AL: "Hypocholesterolemic Agents VII: Inhibition of beta-Hydroxy-beta-methylglutaryl-CoA Reductase by Monoesters of Substituted Glutaric Acids", JOURNAL OF PHARMACEUTICAL SCIENCE, AMERICAN PHARMACEUTICAL ASSOCIATION. WASHINGTON.; US, vol. 69, no. 5, 1 May 1980 (1980-05-01), pages 506 - 509, XP002457176, ISSN: 0022-3549 *
HOEKSTRA M S ET AL: "Chemical development of CI-1008, an enantiomerically pure anticonvulsant", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, CAMBRIDGE, GB, vol. 1, no. 1, 1 January 1997 (1997-01-01), pages 26 - 38, XP000926263 *
RUHEMANN; CUNNINGTON: "Formation of Ethereal Salts of Polycarboxylic Acids", JOURNAL OF THE CHEMICAL SOCIETY, vol. 73, 1898, pages 1006 - 1016, XP009091684 *
SAKURAI ET AL: "Condensation of ethyl malonate and ethyl acetoacetate with aliphatic aldehydes by potassium fluoride", SCIENTIFIC PAPERS OF THE INSTITUTE OF PHYSICAL AND CHEMICALRESEARCH, INSTITUTE PHYSICAL AND CHEMICAL RESEARCH, TOKYO, JP, vol. 53, 1 January 1959 (1959-01-01), pages 250 - 255, XP009091387, ISSN: 0020-3092 *

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Publication number Publication date
WO2009004643A2 (en) 2009-01-08

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