US20050283023A1 - Preparation of pregabalin and related compounds - Google Patents

Preparation of pregabalin and related compounds Download PDF

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Publication number
US20050283023A1
US20050283023A1 US11/157,585 US15758505A US2005283023A1 US 20050283023 A1 US20050283023 A1 US 20050283023A1 US 15758505 A US15758505 A US 15758505A US 2005283023 A1 US2005283023 A1 US 2005283023A1
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formula
compound
salt
alkyl
cyano
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Abandoned
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US11/157,585
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Shanghui Hu
Carlos Martinez
Junhua Tao
William Tully
Patrick Kelleher
Yves Dumond
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Priority to US11/157,585 priority Critical patent/US20050283023A1/en
Publication of US20050283023A1 publication Critical patent/US20050283023A1/en
Priority to US12/254,336 priority patent/US7838686B2/en
Priority to US12/951,429 priority patent/US8044227B2/en
Priority to US13/247,032 priority patent/US8134023B2/en
Abandoned 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
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • 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
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/12—Formation of amino and carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • 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
    • C07C227/20—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 by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
    • 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
    • C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
    • 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
    • C07C229/24—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 more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
    • C12P13/002—Nitriles (-CN)
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Public Health (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US11/157,585 2004-06-21 2005-06-21 Preparation of pregabalin and related compounds Abandoned US20050283023A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/157,585 US20050283023A1 (en) 2004-06-21 2005-06-21 Preparation of pregabalin and related compounds
US12/254,336 US7838686B2 (en) 2004-06-21 2008-10-20 Preparation of pregabalin and related compounds
US12/951,429 US8044227B2 (en) 2004-06-21 2010-11-22 Preparation of pregabalin and related compounds
US13/247,032 US8134023B2 (en) 2004-06-21 2011-09-28 Preparation of pregabalin and related compounds

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US58167104P 2004-06-21 2004-06-21
US62903404P 2004-11-18 2004-11-18
US11/157,585 US20050283023A1 (en) 2004-06-21 2005-06-21 Preparation of pregabalin and related compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/254,336 Continuation US7838686B2 (en) 2004-06-21 2008-10-20 Preparation of pregabalin and related compounds

Publications (1)

Publication Number Publication Date
US20050283023A1 true US20050283023A1 (en) 2005-12-22

Family

ID=35295367

Family Applications (4)

Application Number Title Priority Date Filing Date
US11/157,585 Abandoned US20050283023A1 (en) 2004-06-21 2005-06-21 Preparation of pregabalin and related compounds
US12/254,336 Active US7838686B2 (en) 2004-06-21 2008-10-20 Preparation of pregabalin and related compounds
US12/951,429 Active US8044227B2 (en) 2004-06-21 2010-11-22 Preparation of pregabalin and related compounds
US13/247,032 Active US8134023B2 (en) 2004-06-21 2011-09-28 Preparation of pregabalin and related compounds

Family Applications After (3)

Application Number Title Priority Date Filing Date
US12/254,336 Active US7838686B2 (en) 2004-06-21 2008-10-20 Preparation of pregabalin and related compounds
US12/951,429 Active US8044227B2 (en) 2004-06-21 2010-11-22 Preparation of pregabalin and related compounds
US13/247,032 Active US8134023B2 (en) 2004-06-21 2011-09-28 Preparation of pregabalin and related compounds

Country Status (33)

Country Link
US (4) US20050283023A1 (de)
EP (1) EP1831154B1 (de)
JP (5) JP4174551B2 (de)
KR (3) KR100847928B1 (de)
CN (2) CN102102114B (de)
AP (1) AP2466A (de)
AR (1) AR049446A1 (de)
AT (1) ATE455093T1 (de)
AU (1) AU2005256945B2 (de)
BR (1) BRPI0512347B8 (de)
CA (1) CA2571040C (de)
CR (2) CR8765A (de)
CY (1) CY1110337T1 (de)
DE (1) DE602005018965D1 (de)
DK (1) DK1831154T3 (de)
EA (3) EA200800909A1 (de)
ES (1) ES2336014T3 (de)
GE (1) GEP20104895B (de)
HK (2) HK1104024A1 (de)
HR (1) HRP20100054T1 (de)
IL (1) IL179614A0 (de)
MA (1) MA28674B1 (de)
ME (1) ME01067B (de)
MX (1) MXPA06014228A (de)
NO (1) NO338097B1 (de)
NZ (1) NZ552220A (de)
PL (1) PL1831154T3 (de)
PT (1) PT1831154E (de)
RS (1) RS51210B (de)
SI (1) SI1831154T1 (de)
TW (6) TWI396743B (de)
UA (1) UA83575C2 (de)
WO (1) WO2006000904A2 (de)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060276543A1 (en) * 2005-04-06 2006-12-07 Judith Aronhime Crystalline forms of pregabalin
US20060276544A1 (en) * 2005-05-10 2006-12-07 Lilach Hedvati Pregabalin free of isobutylglutaric acid and a process for preparation thereof
US20060281816A1 (en) * 2005-04-11 2006-12-14 Lilach Hedvati Pregabalin free of lactam and a process for preparation thereof
US20070043241A1 (en) * 2005-05-10 2007-02-22 Lilach Hedvati Optical resolution of 3-carbamoylmethyl-5-methylhexanoic acid
US20070066846A1 (en) * 2005-04-11 2007-03-22 Asher Maymon Process for making (S)-Pregabalin
US20070073085A1 (en) * 2005-05-10 2007-03-29 Lilach Hedvati Method for the preparation of pregabalin and salts thereof
CZ297970B6 (cs) * 2005-08-10 2007-05-09 Zentiva, A. S Zpusob výroby (S)-3-(aminomethyl)-5-methyl-hexanové kyseliny (pregabalinu)
US20070191636A1 (en) * 2005-09-19 2007-08-16 Kansal Vinod K Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the synthesis of (S)-Pregabalin
US20070293694A1 (en) * 2006-05-24 2007-12-20 Lilach Hedvati Processes for the preparation of R-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof
US20080015385A1 (en) * 2006-05-31 2008-01-17 Lilach Hedvati Preparation of (S)-pregabalin-nitrile
WO2007143113A3 (en) * 2006-05-31 2008-01-31 Teva Pharma The use of enzymatic resolution for the preparation of intermediates of pregabalin
US20080306292A1 (en) * 2007-03-22 2008-12-11 Vinod Kumar Kansal Synthesis of (S)-(+)-3-(aminomethyl)-5-methyl hexanoic acid
US20080311635A1 (en) * 2007-05-14 2008-12-18 Dipharma Francis S.R.L. Process for the preparation of (s)(+)-3-(aminomethyl)-5-methylhexanoic acid
US20090062393A1 (en) * 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched pregabalin
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
US20090143615A1 (en) * 2007-12-03 2009-06-04 Dipharma Francis S.R.L. Process for the Preparation of (S)(+)-3-(Aminomethyl)-5-Methylhexanoic Acid
US20090312560A1 (en) * 2008-06-10 2009-12-17 Lambertus Thijs Processes for making pregabalin and intermediates therefor
US20100087525A1 (en) * 2008-06-23 2010-04-08 Lilach Hedvati Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester
WO2010070593A3 (en) * 2008-12-19 2010-11-04 Pfizer Ireland Pharmaceuticals Malonate esters
USRE41920E1 (en) 1996-07-24 2010-11-09 Warner-Lambert Company Llc Isobutylgaba and its derivatives for the treatment of pain
US20100312010A1 (en) * 2007-12-18 2010-12-09 Watson Pharma Private Limited Process for the Preparation of (S)-Pregabalin
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
US8063244B2 (en) 2009-05-07 2011-11-22 Dipharma Francis S.R.L. Process for the synthesis of pregabalin
CN107445864A (zh) * 2017-08-09 2017-12-08 无锡殷达尼龙有限公司 一种纯化长碳链氰基酸产物的方法
CN113651717A (zh) * 2021-08-05 2021-11-16 浙江工业大学 一种光学纯异丁基丁二腈的消旋方法

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Publication number Priority date Publication date Assignee Title
JP5157576B2 (ja) 2007-05-14 2013-03-06 住友化学株式会社 光学活性２−アルキル−１，１，３−トリアルコキシカルボニルプロパンの製造方法
KR100846419B1 (ko) * 2007-08-10 2008-07-15 한국과학기술원 프레가발린의 신규한 제조 방법
CA2710152A1 (en) * 2007-12-26 2009-07-02 Generics (Uk) Limited Processes to pregabalin
EP2116618A1 (de) * 2008-05-09 2009-11-11 Agency for Science, Technology And Research Diagnose und Behandlung des Kawasaki-Syndroms
WO2009141362A2 (en) 2008-05-21 2009-11-26 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
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
WO2012059797A1 (en) * 2010-11-04 2012-05-10 Lupin Limited Process for synthesis of (s) - pregabalin
KR101306585B1 (ko) * 2011-04-14 2013-09-10 한국외국어대학교 연구산학협력단 프레가발린의 제조방법
CN102952057B (zh) * 2012-11-07 2015-09-09 浙江普洛家园药业有限公司 一种4-异丁基吡咯烷-2-酮的制备方法
JP6225490B2 (ja) * 2013-05-31 2017-11-08 大日本印刷株式会社 医薬品包装体
US10076550B2 (en) * 2014-06-25 2018-09-18 Council Of Scientific & Industrial Research Synergistic pharmaceutical composition for gastroinestinal disorders
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
CN104557576B (zh) * 2014-12-19 2019-07-19 浙江华海药业股份有限公司 一种高纯度普瑞巴林的制备方法
CN105348125A (zh) * 2015-11-26 2016-02-24 太仓运通生物化工有限公司 一种以异戊醛为原料合成普瑞巴林的方法
CN108358799B (zh) * 2018-04-24 2020-11-10 贵州师范大学 一种普瑞巴林的制备方法
CN109503403B (zh) * 2018-12-21 2021-11-16 卓和药业集团股份有限公司 一种普瑞巴林的拆分方法
CN113248416B (zh) * 2020-02-10 2024-03-26 江西博腾药业有限公司 1-((苄氧基)羰基)-4-乙基吡咯烷-3-羧酸的制备方法及其应用
WO2021161346A1 (en) 2020-02-14 2021-08-19 Council Of Scientific And Industrial Research Process for the preparation of gamma amino butyric acids and analogs thereof
CN111205288B (zh) 2020-02-19 2021-03-30 四川大学 一种(1S,12bS)内酰胺酯化合物的合成方法
CN113880724A (zh) * 2021-12-06 2022-01-04 南京桦冠生物技术有限公司 一种3-(2-氨基苯基)-2-丙烯酸酯的制备方法

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