WO2008062460A3 - Crystalline forms of pregabalin - Google Patents

Crystalline forms of pregabalin Download PDF

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Publication number
WO2008062460A3
WO2008062460A3 PCT/IN2007/000467 IN2007000467W WO2008062460A3 WO 2008062460 A3 WO2008062460 A3 WO 2008062460A3 IN 2007000467 W IN2007000467 W IN 2007000467W WO 2008062460 A3 WO2008062460 A3 WO 2008062460A3
Authority
WO
WIPO (PCT)
Prior art keywords
pregabalin
crystalline
crystalline forms
methylhex
carbethoxy
Prior art date
Application number
PCT/IN2007/000467
Other languages
French (fr)
Other versions
WO2008062460A2 (en
Inventor
Dwivedi Shriprakash Dhar
Rajiv Kumar
Tippanu Thirupathi Rao
Doshi Ketan Ambalal
Original Assignee
Cadila Healthcare Ltd
Dwivedi Shriprakash Dhar
Rajiv Kumar
Tippanu Thirupathi Rao
Doshi Ketan Ambalal
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, Dwivedi Shriprakash Dhar, Rajiv Kumar, Tippanu Thirupathi Rao, Doshi Ketan Ambalal filed Critical Cadila Healthcare Ltd
Publication of WO2008062460A2 publication Critical patent/WO2008062460A2/en
Publication of WO2008062460A3 publication Critical patent/WO2008062460A3/en

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Classifications

    • 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
    • C07C227/34—Preparation of optical isomers by separation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • C07C59/50—Mandelic acid
    • 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
    • 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
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Abstract

The invention relates to crystalline 'forms of Pregabalin and their process o preparation. The invention also relates to a process for preparing 2-carbethoxy-5- methylhex-2-enoic acid ethyl ester, an important intermediat for synthesis of crystalline Pregabalin, having less than about, 1-2% 2-carbethoxy-5-methylhex-3-enoic acid ethyl ester. Moreover, the present invention provides an industrially applicable process for recovery of chiral reagent used for resolution of the (+) (-)Pregabalin; thereby to provide a cost effective and economical process for preparation of Pregabalin.
PCT/IN2007/000467 2006-10-06 2007-10-05 Crystalline forms of pregabalin WO2008062460A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1655MU2006 2006-10-06
IN1655/MUM/2006 2006-10-06

Publications (2)

Publication Number Publication Date
WO2008062460A2 WO2008062460A2 (en) 2008-05-29
WO2008062460A3 true WO2008062460A3 (en) 2009-01-15

Family

ID=39259624

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000467 WO2008062460A2 (en) 2006-10-06 2007-10-05 Crystalline forms of pregabalin

Country Status (1)

Country Link
WO (1) WO2008062460A2 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1879851B1 (en) 2005-05-10 2010-11-03 Teva Pharmaceutical Industries Ltd Method for the preparation of pregabalin and salts thereof
ATE523484T1 (en) 2005-05-10 2011-09-15 Teva Pharma OPTICAL SOLUTION FROM 3-CARBAMOYLMETHYL-5-METHYL-HEXANIC ACID
ES2398579T3 (en) 2005-09-19 2013-03-20 Teva Pharmaceutical Industries Ltd An asymmetric synthesis of (S) - (+) - 3- (aminomethyl) -5-methylhexanoic acid
WO2009125427A2 (en) * 2008-02-18 2009-10-15 Matrix Laboratories Limited Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid
WO2010061403A2 (en) * 2008-11-26 2010-06-03 Ind-Swift Laboratories Limited Process to prepare highly pure (s)-pregabalin
ES2362913B1 (en) * 2009-12-24 2012-05-24 Moehs Iberica S.L. NEW METHOD FOR THE PREPARATION OF (S) -PREGABALINA.
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
WO2012059797A1 (en) * 2010-11-04 2012-05-10 Lupin Limited Process for synthesis of (s) - pregabalin
CA2888877C (en) 2012-11-07 2021-07-27 Hikal Limited A process for the preparation of pregabalin
CN103145571A (en) * 2013-03-27 2013-06-12 李兴惠 Crystal form of derivative of aminomethyl caproic acid
CN103450045A (en) * 2013-08-22 2013-12-18 河北诚信有限责任公司 Synthetic method of pregabalin intermediate 2-carboxethyl-3-cyano-5-methylethyl caproate
CN104649919B (en) * 2015-02-10 2021-02-12 浙江华海药业股份有限公司 Preparation method of small-particle pregabalin
CN105367434A (en) * 2015-11-26 2016-03-02 太仓运通生物化工有限公司 Method for synthesizing pregabalin from isobutyraldehyde
CN111170879B (en) * 2020-01-21 2023-07-14 石药集团中奇制药技术（石家庄）有限公司 Small-granularity pregabalin and preparation method thereof
EP4103168A4 (en) 2020-02-14 2024-04-24 Council Scient Ind Res Process for the preparation of gamma amino butyric acids and analogs thereof
CN112939809A (en) * 2020-12-30 2021-06-11 江苏恒沛药物科技有限公司 Preparation method of 1-cyano-3-methyl diethyl butylmalonate

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322548A (en) * 1980-02-13 1982-03-30 Kay Fries, Inc. Resolution of racemic mandelic acid
WO1996040617A1 (en) * 1995-06-07 1996-12-19 Warner-Lambert Company Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid
CN1827590A (en) * 2006-04-14 2006-09-06 北京润德康医药技术有限公司 Novel pregabalin crystalline form, its preparing process and pharmaceutical compositions thereof
US20060270871A1 (en) * 2005-05-30 2006-11-30 Khanduri Chandra H Polymorphic form i of pregabalin and processes for its preparation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322548A (en) * 1980-02-13 1982-03-30 Kay Fries, Inc. Resolution of racemic mandelic acid
WO1996040617A1 (en) * 1995-06-07 1996-12-19 Warner-Lambert Company Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid
US20060270871A1 (en) * 2005-05-30 2006-11-30 Khanduri Chandra H Polymorphic form i of pregabalin and processes for its preparation
CN1827590A (en) * 2006-04-14 2006-09-06 北京润德康医药技术有限公司 Novel pregabalin crystalline form, its preparing process and pharmaceutical compositions thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "Crystal form of the active ingredient in LYRICA 300 mg hard capsules (3S)-3-(Aminomethyl)-5-methylhexanoic acid", INTERNET ARTICLE, 22 February 2005 (2005-02-22), XP002477783, Retrieved from the Internet <URL:www.ip.com/pubview/IPCOM000073295D> [retrieved on 20080422] *
DATABASE WPI Week 200707, Derwent World Patents Index; AN 2007-058680, XP002477784 *
N. VENU ET AL: "(S)-3-(Ammoniomethyl)-5-methyl-hexanoate (pregabalin)", ACTA CRYST. SECTION C, vol. C63, 2007, pages O306 - O308, XP002504548 *

Also Published As

Publication number Publication date
WO2008062460A2 (en) 2008-05-29

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