WO2007139933A3 - Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof - Google Patents

Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof Download PDF

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Publication number
WO2007139933A3
WO2007139933A3 PCT/US2007/012485 US2007012485W WO2007139933A3 WO 2007139933 A3 WO2007139933 A3 WO 2007139933A3 US 2007012485 W US2007012485 W US 2007012485W WO 2007139933 A3 WO2007139933 A3 WO 2007139933A3
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WO
WIPO (PCT)
Prior art keywords
salts
processes
preparation
methylhexanoic acid
carbamoyl methyl
Prior art date
Application number
PCT/US2007/012485
Other languages
French (fr)
Other versions
WO2007139933A2 (en
Inventor
Lilach Hedvati
Eyal Gilboa
Sharon Avhar-Maydan
Original Assignee
Teva Pharma
Lilach Hedvati
Eyal Gilboa
Sharon Avhar-Maydan
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 Teva Pharma, Lilach Hedvati, Eyal Gilboa, Sharon Avhar-Maydan filed Critical Teva Pharma
Priority to CA002649115A priority Critical patent/CA2649115A1/en
Priority to EP07795344A priority patent/EP2019817A2/en
Priority to BRPI0702883-0A priority patent/BRPI0702883A2/en
Publication of WO2007139933A2 publication Critical patent/WO2007139933A2/en
Publication of WO2007139933A3 publication Critical patent/WO2007139933A3/en
Priority to IL194874A priority patent/IL194874A0/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • 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
    • 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
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • 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
    • C07C229/34—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 containing six-membered aromatic rings
    • C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • 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

Abstract

Provided are processes for the synthesis of R-(+)-3-(carbamoylmethyl)-5-methylhexanoic acid and salts thereof, intermediates in the synthesis of S-pregabalin.
PCT/US2007/012485 2006-05-24 2007-05-24 Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof WO2007139933A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002649115A CA2649115A1 (en) 2006-05-24 2007-05-24 Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof
EP07795344A EP2019817A2 (en) 2006-05-24 2007-05-24 Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof
BRPI0702883-0A BRPI0702883A2 (en) 2006-05-24 2007-05-24 process for the preparation of r - (+) - 3- (carbamoyl methyl) -5-methylhexanoic acid and its salts
IL194874A IL194874A0 (en) 2006-05-24 2008-10-23 Processes for the prepartion of r-(+)-3-(carbomoyl methyl)-5-methylhexanoic acid and salts thereof

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
US80832006P 2006-05-24 2006-05-24
US60/808,320 2006-05-24
US81424506P 2006-06-15 2006-06-15
US60/814,245 2006-06-15
US84381706P 2006-09-11 2006-09-11
US60/843,817 2006-09-11
US85086806P 2006-10-10 2006-10-10
US60/850,868 2006-10-10
US91817707P 2007-03-14 2007-03-14
US60/918,177 2007-03-14
US92034807P 2007-03-26 2007-03-26
US60/920,348 2007-03-26

Publications (2)

Publication Number Publication Date
WO2007139933A2 WO2007139933A2 (en) 2007-12-06
WO2007139933A3 true WO2007139933A3 (en) 2008-04-17

Family

ID=38779241

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/012485 WO2007139933A2 (en) 2006-05-24 2007-05-24 Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof

Country Status (7)

Country Link
US (1) US7462738B2 (en)
EP (1) EP2019817A2 (en)
KR (1) KR20080027880A (en)
CA (1) CA2649115A1 (en)
IL (1) IL194874A0 (en)
TW (1) TW200815323A (en)
WO (1) WO2007139933A2 (en)

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CA2619472A1 (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
KR20080016658A (en) * 2006-04-24 2008-02-21 테바 파마슈티컬 인더스트리즈 리미티드 Processes for the synthesis of 3-isobutylglutaric acid
US8097754B2 (en) 2007-03-22 2012-01-17 Teva Pharmaceutical Industries Ltd. Synthesis of (S)-(+)-3-(aminomethyl)-5-methyl hexanoic acid
EP1992609A1 (en) * 2007-05-14 2008-11-19 Dipharma Francis S.r.l. A process for the preparation of a (S)(+)-3-(aminomethyl)-5-methylhexanoic acid
US20090137842A1 (en) * 2007-10-03 2009-05-28 Vollerner Yuri Pregabalin -4-eliminate, pregabalin 5-eliminate, their use as reference marker and standard, and method to produce pregabalin containing low levels thereof
EP2116618A1 (en) 2008-05-09 2009-11-11 Agency for Science, Technology And Research Diagnosis and treatment of Kawasaki disease
BRPI0913094A2 (en) 2008-05-21 2015-08-11 Sandoz Ag Process for stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl hexanoic acid ester
EP2213659A1 (en) 2009-01-29 2010-08-04 The Provost, Fellows and Scholars of the College of the Holy and Undivided Trinity of Queen Elizabeth near Dublin Intermediates in the Enantioselective Synthesis of 3-(Aminomethyl)-5-Methyl-Hexanoic Acid
WO2011078172A1 (en) * 2009-12-25 2011-06-30 株式会社カネカ Process for production of optically active 3-substituted glutaric acid monoamide
US10023885B2 (en) 2012-11-07 2018-07-17 Hikal Limited Process for the preparation of pregabalin
US20140243412A1 (en) * 2013-02-28 2014-08-28 Dr. Reddy's Laboratories Ltd. Process for preparation of pregabalin
WO2016075082A1 (en) 2014-11-10 2016-05-19 Sandoz Ag Stereoselective reductive amination of alpha-chiral aldehydes using omega-transaminases for the synthesis of precursors of pregabalin and brivaracetam
WO2020051796A1 (en) * 2018-09-12 2020-03-19 上海宣泰医药科技有限公司 Preparation method for brivaracetam and intermediate thereof
CN110407715A (en) * 2019-07-01 2019-11-05 陕西师范大学 A kind of synthetic method of pregabalin intermediate

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TW200815323A (en) 2008-04-01
CA2649115A1 (en) 2007-12-06
WO2007139933A2 (en) 2007-12-06
US7462738B2 (en) 2008-12-09
KR20080027880A (en) 2008-03-28
IL194874A0 (en) 2009-08-03
US20070293694A1 (en) 2007-12-20
EP2019817A2 (en) 2009-02-04

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