WO2011141923A3 - Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin - Google Patents

Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin Download PDF

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Publication number
WO2011141923A3
WO2011141923A3 PCT/IN2010/000440 IN2010000440W WO2011141923A3 WO 2011141923 A3 WO2011141923 A3 WO 2011141923A3 IN 2010000440 W IN2010000440 W IN 2010000440W WO 2011141923 A3 WO2011141923 A3 WO 2011141923A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
methyl
hexanoic acid
pregabalin
alkyl ester
Prior art date
Application number
PCT/IN2010/000440
Other languages
French (fr)
Other versions
WO2011141923A2 (en
Inventor
Bhairab Nath Roy
Girij Pal Singh
Piyush Suresh Lathi
Manoj Kunjabihari Agrawal
Vijay Sadashiv Pise
Original Assignee
Lupin Limited
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 Lupin Limited filed Critical Lupin Limited
Publication of WO2011141923A2 publication Critical patent/WO2011141923A2/en
Publication of WO2011141923A3 publication Critical patent/WO2011141923A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
    • C07C255/22—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton containing cyano groups and at least two carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The present invention is directed towards synthesis of (S) - 3-cyano-5-methyl-hexanoic acid ethyl ester. A cost effective, eco-friendly process for preparation of enantiomerically pure (S)-3-cyano-5-methyl-hexanoic acid alkyl ester, intermediate of γ-amino acids, particularly (S)-pregabalin.
PCT/IN2010/000440 2010-05-14 2010-06-28 Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin WO2011141923A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN536KO2010 2010-05-14
IN536/KOL/2010 2010-05-14

Publications (2)

Publication Number Publication Date
WO2011141923A2 WO2011141923A2 (en) 2011-11-17
WO2011141923A3 true WO2011141923A3 (en) 2012-01-19

Family

ID=42732683

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2010/000440 WO2011141923A2 (en) 2010-05-14 2010-06-28 Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin

Country Status (1)

Country Link
WO (1) WO2011141923A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2888877C (en) * 2012-11-07 2021-07-27 Hikal Limited A process for the preparation of pregabalin
US9422230B2 (en) 2013-05-09 2016-08-23 Council Of Scientific And Industrial Research Process for the preparation of an anticonvulsant agent pregabalin hydrochloride
CN106608935B (en) * 2015-10-27 2019-07-19 中国石油化工股份有限公司 Catalytic component, catalyst and its application for olefinic polymerization

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996040617A1 (en) * 1995-06-07 1996-12-19 Warner-Lambert Company Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid
US20030212290A1 (en) * 2000-01-27 2003-11-13 Burk Mark Joseph Asymmetric synthesis of pregabalin
US20050283023A1 (en) * 2004-06-21 2005-12-22 Shanghui Hu Preparation of pregabalin and related compounds
WO2007143113A2 (en) * 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. The use of enzymatic resolution for the preparation of intermediates of pregabalin
WO2007143152A2 (en) * 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. Preparation of (s)-pregabalin-nitrile
WO2008062460A2 (en) * 2006-10-06 2008-05-29 Cadila Healthcare Limited Crystalline forms of pregabalin

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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
US6001876A (en) 1996-07-24 1999-12-14 Warner-Lambert Company Isobutylgaba and its derivatives for the treatment of pain
US6329429B1 (en) 1997-06-25 2001-12-11 Warner-Lambert Company Use of GABA analogs such as Gabapentin in the manufacture of a medicament for treating inflammatory diseases
AU9019198A (en) 1997-08-19 1999-03-08 Warner-Lambert Company Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotor stimulants
US6127418A (en) 1997-08-20 2000-10-03 Warner-Lambert Company GABA analogs to prevent and treat gastrointestinal damage
AU8668598A (en) 1997-08-20 1999-03-08 University Of Oklahoma, The Gaba analogs to prevent and treat gastrointestinal damage
JP2002520286A (en) 1998-07-09 2002-07-09 ワーナー−ランバート・カンパニー Composition comprising a GABA analog and caffeine
WO2000002546A2 (en) 1998-07-09 2000-01-20 Warner-Lambert Company Use of caba-analogues for treating insomnia
EP1121114B1 (en) 1998-10-16 2007-01-10 Warner-Lambert Company Llc Use of gaba analogs for the manufacture of a medicament for the treatment of mania and bipolar disorders
UA82292C2 (en) 2004-04-14 2008-03-25 Пфайзер Продактс Инк. A method for stereoselective byconversion of aliphatic dinitriles into cyanocarboxylic acids (variants)
JP4961568B2 (en) 2006-03-03 2012-06-27 国立大学法人 東京大学 Ligand, production method thereof, and catalyst using the ligand

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996040617A1 (en) * 1995-06-07 1996-12-19 Warner-Lambert Company Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid
US20030212290A1 (en) * 2000-01-27 2003-11-13 Burk Mark Joseph Asymmetric synthesis of pregabalin
US20050283023A1 (en) * 2004-06-21 2005-12-22 Shanghui Hu Preparation of pregabalin and related compounds
WO2007143113A2 (en) * 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. The use of enzymatic resolution for the preparation of intermediates of pregabalin
WO2007143152A2 (en) * 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. Preparation of (s)-pregabalin-nitrile
WO2008062460A2 (en) * 2006-10-06 2008-05-29 Cadila Healthcare Limited Crystalline forms of pregabalin

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HOEKSTRA M S ET AL: "Chemical development of CI-1008, an enantiomerically pure anticonvulsant", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, CAMBRIDGE, GB LNKD- DOI:10.1021/OP9600320, vol. 1, no. 1, 1 January 1997 (1997-01-01), pages 26 - 38, XP000926263 *
MARTINEZ C A ET AL: "Development of a Chemoenzymatic Manufacturing Process for Pregabalin", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 12, no. 3, 16 May 2008 (2008-05-16), pages 392 - 398, XP002556922, ISSN: 1083-6160, [retrieved on 20080318], DOI: DOI:10.1021/OP7002248 *

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