AU2014240833B2 - Process and intermediates for the preparation of pregabalin - Google Patents

Process and intermediates for the preparation of pregabalin Download PDF

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Publication number
AU2014240833B2
AU2014240833B2 AU2014240833A AU2014240833A AU2014240833B2 AU 2014240833 B2 AU2014240833 B2 AU 2014240833B2 AU 2014240833 A AU2014240833 A AU 2014240833A AU 2014240833 A AU2014240833 A AU 2014240833A AU 2014240833 B2 AU2014240833 B2 AU 2014240833B2
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AU
Australia
Prior art keywords
alkyl
formula
compound
acid
crc3
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AU2014240833A
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English (en)
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AU2014240833A1 (en
Inventor
Sebastien DEBARGE
David Thomas Erdman
Michael John KARMILOWICZ
Rajesh Kumar
Padraig Mary O'neill
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Pfizer Ireland Pharmaceuticals UC
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Pfizer Ireland Pharmaceuticals UC
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Publication of AU2014240833A1 publication Critical patent/AU2014240833A1/en
Priority to AU2016203782A priority Critical patent/AU2016203782B2/en
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Publication of AU2014240833B2 publication Critical patent/AU2014240833B2/en
Ceased legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • 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
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • 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
    • C07C227/12—Formation of amino and carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/66—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/005—Amino acids other than alpha- or beta amino acids, e.g. gamma amino acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • 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
    • C07C227/08—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 by reaction of ammonia or amines with acids containing functional groups
    • 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
    • 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
    • C07C59/74—Unsaturated compounds containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Steroid Compounds (AREA)
AU2014240833A 2013-03-27 2014-03-25 Process and intermediates for the preparation of pregabalin Ceased AU2014240833B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2016203782A AU2016203782B2 (en) 2013-03-27 2016-06-07 Process and intermediates for the preparation of pregabalin

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361805786P 2013-03-27 2013-03-27
US61/805,786 2013-03-27
PCT/IB2014/060140 WO2014155291A1 (en) 2013-03-27 2014-03-25 Process and intermediates for the preparation of pregabalin

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2016203782A Division AU2016203782B2 (en) 2013-03-27 2016-06-07 Process and intermediates for the preparation of pregabalin

Publications (2)

Publication Number Publication Date
AU2014240833A1 AU2014240833A1 (en) 2015-10-01
AU2014240833B2 true AU2014240833B2 (en) 2016-07-07

Family

ID=50483187

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2014240833A Ceased AU2014240833B2 (en) 2013-03-27 2014-03-25 Process and intermediates for the preparation of pregabalin
AU2016203782A Ceased AU2016203782B2 (en) 2013-03-27 2016-06-07 Process and intermediates for the preparation of pregabalin

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU2016203782A Ceased AU2016203782B2 (en) 2013-03-27 2016-06-07 Process and intermediates for the preparation of pregabalin

Country Status (21)

Country Link
US (1) US20160024540A1 (enExample)
EP (2) EP2978748B1 (enExample)
JP (1) JP2016516744A (enExample)
KR (1) KR20150121202A (enExample)
CN (3) CN107746834A (enExample)
AU (2) AU2014240833B2 (enExample)
BR (2) BR112015024859A2 (enExample)
CA (1) CA2905411A1 (enExample)
CY (1) CY1118945T1 (enExample)
DK (1) DK2978748T3 (enExample)
ES (1) ES2630128T3 (enExample)
HU (1) HUE034834T2 (enExample)
IL (1) IL241438A0 (enExample)
MX (1) MX2015013589A (enExample)
PL (1) PL2978748T3 (enExample)
PT (1) PT2978748T (enExample)
RU (2) RU2017125261A (enExample)
SG (1) SG11201506998XA (enExample)
SI (1) SI2978748T1 (enExample)
WO (1) WO2014155291A1 (enExample)
ZA (1) ZA201506798B (enExample)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE036104T2 (hu) 2009-01-08 2018-06-28 Codexis Inc Transzamináz polipeptidek
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
EP3761036B1 (en) 2015-03-03 2025-11-19 ARK Diagnostics, Inc. Pregabalin immunoassays
WO2018231462A1 (en) * 2017-06-14 2018-12-20 Codexis, Inc. Engineered transaminase polypeptides for industrial biocatalysis
BR112021000202B1 (pt) 2018-07-09 2023-03-28 Merck Sharp & Dohme Llc Métodos para síntese enzimática de nucleosídeo 4'-etinila 2-desóxi e compostos
CN111004102B (zh) * 2019-12-23 2022-11-04 万华化学集团股份有限公司 一种制备光学活性香茅醛的方法及用于该方法的催化剂
CN118772033A (zh) * 2024-06-11 2024-10-15 中国科学院成都生物研究所 一种普瑞巴林三聚体的合成方法
CN121914996B (zh) * 2026-03-27 2026-06-23 浙江华康药业股份有限公司 一种甲酸脱氢酶突变体及其应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003093220A1 (en) * 2002-04-30 2003-11-13 Warner-Lambert Company Llc Process for preparing highly functionalized y-butyrolactams and y-amino acids
WO2008127646A2 (en) * 2007-04-11 2008-10-23 Dsm Ip Assets B.V. Transaminase-based processes for preparation of pregabalin

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GB834100A (en) 1957-10-26 1960-05-04 Eastman Kodak Co Improvements in the preparation of mixed aldols
US4239636A (en) * 1978-10-23 1980-12-16 Exxon Research & Engineering Co. Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions
US6197819B1 (en) 1990-11-27 2001-03-06 Northwestern University Gamma amino butyric acid analogs and optical isomers
JPH06107597A (ja) * 1992-03-12 1994-04-19 Noguchi Kenkyusho （Ｒ）−α−ヒドロキシ−β，γ−不飽和エステルの製造法
US5268387A (en) * 1992-04-24 1993-12-07 Allergan, Inc. Pharmaceutical compositions and method for administering 3 and 4-substituted 2(5H)-furanones to a mammal for inhibiting bone loss
CA2236939A1 (en) * 1995-11-07 1997-05-15 E. John Deviny Initiator system and adhesive composition made therewith
EP0934061B3 (en) 1996-07-24 2015-01-21 Warner-Lambert Company LLC Isobutylgaba and its derivatives for the treatment of pain
SE9801992D0 (sv) * 1998-06-04 1998-06-04 Astra Ab New 3-aryl-2-hydroxypropionic acid derivative I
MX2007012606A (es) * 2005-04-11 2008-01-11 Teva Pharma Proceso para elaborar (s)-pregabalina.
RU2008109031A (ru) * 2005-08-11 2009-09-20 Вертекс Фармасьютикалз Инкорпорейтед (Us) Модуляторы муковисцидозного трансмембранного регулятора проводимости
KR100846419B1 (ko) * 2007-08-10 2008-07-15 한국과학기술원 프레가발린의 신규한 제조 방법
CN101362696A (zh) * 2008-09-27 2009-02-11 开原亨泰精细化工厂 3-氨甲基-5-甲基己酸即混旋普瑞巴林的制备新方法
HUE036104T2 (hu) * 2009-01-08 2018-06-28 Codexis Inc Transzamináz polipeptidek
WO2011086565A1 (en) * 2010-01-15 2011-07-21 Lupin Limited Method for preparation of enantiomerically enriched and/or racemic gamma-amino acids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003093220A1 (en) * 2002-04-30 2003-11-13 Warner-Lambert Company Llc Process for preparing highly functionalized y-butyrolactams and y-amino acids
WO2008127646A2 (en) * 2007-04-11 2008-10-23 Dsm Ip Assets B.V. Transaminase-based processes for preparation of pregabalin

Also Published As

Publication number Publication date
ES2630128T3 (es) 2017-08-18
PL2978748T3 (pl) 2017-09-29
SG11201506998XA (en) 2015-10-29
CN105051022B (zh) 2017-10-27
CN105051022A (zh) 2015-11-11
ZA201506798B (en) 2019-05-29
MX2015013589A (es) 2016-06-23
US20160024540A1 (en) 2016-01-28
CN107746834A (zh) 2018-03-02
BR122017006144A2 (pt) 2019-09-03
CN107556273A (zh) 2018-01-09
EP2978748B1 (en) 2017-05-10
EP3216863A1 (en) 2017-09-13
SI2978748T1 (sl) 2017-07-31
RU2017125261A (ru) 2019-01-31
HK1213882A1 (zh) 2016-07-15
WO2014155291A1 (en) 2014-10-02
KR20150121202A (ko) 2015-10-28
CA2905411A1 (en) 2014-10-02
JP2016516744A (ja) 2016-06-09
AU2014240833A1 (en) 2015-10-01
HUE034834T2 (en) 2018-03-28
CY1118945T1 (el) 2018-01-10
EP2978748A1 (en) 2016-02-03
AU2016203782A1 (en) 2016-06-23
BR112015024859A2 (pt) 2017-10-10
RU2015138545A (ru) 2017-05-03
AU2016203782B2 (en) 2017-06-01
IL241438A0 (en) 2015-11-30
RU2628298C2 (ru) 2017-08-15
DK2978748T3 (en) 2017-07-24
PT2978748T (pt) 2017-07-06

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