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WO2010070593A3 - Malonate esters - Google Patents

Malonate esters Download PDF

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Publication number
WO2010070593A3
WO2010070593A3 PCT/IB2009/055786 IB2009055786W WO2010070593A3 WO 2010070593 A3 WO2010070593 A3 WO 2010070593A3 IB 2009055786 W IB2009055786 W IB 2009055786W WO 2010070593 A3 WO2010070593 A3 WO 2010070593A3
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
aryl
malonate esters
enantiomerically enriched
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.)
Ceased
Application number
PCT/IB2009/055786
Other languages
French (fr)
Other versions
WO2010070593A2 (en
Inventor
Benjamin Simon Davies
Mark M. Guzman
Carlos A. Martinez
Paul Oliver Mcdaid
Padraig Mary O'neill
Elango Shanmugam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Ireland Pharmaceuticals
Original Assignee
Pfizer Ireland Pharmaceuticals
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 Pfizer Ireland Pharmaceuticals filed Critical Pfizer Ireland Pharmaceuticals
Publication of WO2010070593A2 publication Critical patent/WO2010070593A2/en
Publication of WO2010070593A3 publication Critical patent/WO2010070593A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention provides a compound of formula (I), in an enantiomerically enriched form; wherein R1 and R2 are each independently selected from optionally substituted alkyl, cycloalkyl, aryl-alkyl and aryl, wherein the 3S-enantiomer is present in excess and the enantiomeric excess is at least 10%. There is also provided a method of preparing, in an enantiomerically enriched form, the compound of formula (I). Use of a compound of formula (I) in a method of preparing pregabalin is also discussed.
PCT/IB2009/055786 2008-12-19 2009-12-16 Malonate esters Ceased WO2010070593A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IE20081008 2008-12-19
IE2008/1008 2008-12-19

Publications (2)

Publication Number Publication Date
WO2010070593A2 WO2010070593A2 (en) 2010-06-24
WO2010070593A3 true WO2010070593A3 (en) 2010-11-04

Family

ID=42169662

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2009/055786 Ceased WO2010070593A2 (en) 2008-12-19 2009-12-16 Malonate esters

Country Status (1)

Country Link
WO (1) WO2010070593A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012025861A1 (en) 2010-08-23 2012-03-01 Pfizer Manufacturing Ireland Process for the preparation of ( s ) - 3 - cyano - 5 - methylhexanoic acid derivatives adn of pregabalin
DE112016001317T5 (en) 2015-03-20 2018-01-04 Stanford University Carbonate-assisted carboxylation reaction for the synthesis of valuable organic compounds
WO2017183539A1 (en) * 2016-04-18 2017-10-26 第一三共株式会社 Method for producing bicyclic compound using meldrum's acid
CN109232311B (en) * 2018-10-08 2021-02-19 浙江新和成股份有限公司 Green and efficient synthesis method of pregabalin
CN117263824A (en) * 2023-09-21 2023-12-22 江苏阿尔法药业股份有限公司 Synthesis process of pregabalin chiral intermediate

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050283023A1 (en) * 2004-06-21 2005-12-22 Shanghui Hu Preparation of pregabalin and related compounds

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3823864A1 (en) 1988-01-29 1989-08-10 Kernforschungsanlage Juelich ENYMATIC PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE CYANHYDRINES
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
AU714980B2 (en) 1996-07-24 2000-01-13 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain
EP1250311B1 (en) 2000-01-27 2004-03-17 Warner-Lambert Company Asymmetric synthesis of pregabalin

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050283023A1 (en) * 2004-06-21 2005-12-22 Shanghui Hu Preparation of pregabalin and related compounds
WO2006000904A2 (en) * 2004-06-21 2006-01-05 Warner-Lambert Company Llc Preparation of pregabalin and related compounds

Also Published As

Publication number Publication date
WO2010070593A2 (en) 2010-06-24

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