SK282865B6 - Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty - Google Patents

Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty Download PDF

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Publication number
SK282865B6
SK282865B6 SK1645-97A SK164597A SK282865B6 SK 282865 B6 SK282865 B6 SK 282865B6 SK 164597 A SK164597 A SK 164597A SK 282865 B6 SK282865 B6 SK 282865B6
Authority
SK
Slovakia
Prior art keywords
acid
aminomethyl
water
methylhexanoic acid
methylhexanoic
Prior art date
Application number
SK1645-97A
Other languages
English (en)
Slovak (sk)
Other versions
SK164597A3 (en
Inventor
Todd Michel Grote
Brian Keith Huckabee
Thomas Mulhern
Denis Martin Sobieray
Robert Daniel Titus
Original Assignee
Warner-Lambert Company
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 Warner-Lambert Company filed Critical Warner-Lambert Company
Publication of SK164597A3 publication Critical patent/SK164597A3/sk
Publication of SK282865B6 publication Critical patent/SK282865B6/sk

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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
    • 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
    • C07C227/10—Formation of amino groups in compounds containing carboxyl groups with simultaneously increasing the number of carbon atoms in 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Seasonings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
SK1645-97A 1995-06-07 1996-05-13 Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty SK282865B6 (sk)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/474,874 US5637767A (en) 1995-06-07 1995-06-07 Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid
PCT/US1996/006819 WO1996040617A1 (en) 1995-06-07 1996-05-13 Method of making (s)-3-(aminomethyl)-5-methylhexanoic acid

Publications (2)

Publication Number Publication Date
SK164597A3 SK164597A3 (en) 1998-05-06
SK282865B6 true SK282865B6 (sk) 2003-01-09

Family

ID=23885291

Family Applications (2)

Application Number Title Priority Date Filing Date
SK606-2002A SK283507B6 (sk) 1995-06-07 1996-05-13 Spôsob prípravy kyseliny (±)-3-(aminometyl)-5-metylhexánovej
SK1645-97A SK282865B6 (sk) 1995-06-07 1996-05-13 Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SK606-2002A SK283507B6 (sk) 1995-06-07 1996-05-13 Spôsob prípravy kyseliny (±)-3-(aminometyl)-5-metylhexánovej

Country Status (18)

Country Link
US (4) US5637767A (cs)
EP (1) EP0830338B1 (cs)
JP (1) JP3874306B2 (cs)
AT (1) ATE210628T1 (cs)
CA (1) CA2219150C (cs)
CZ (2) CZ296895B6 (cs)
DE (1) DE69617948T2 (cs)
DK (1) DK0830338T3 (cs)
EE (1) EE04053B1 (cs)
ES (1) ES2170231T3 (cs)
GE (1) GEP19991870B (cs)
HU (2) HU229957B1 (cs)
NZ (2) NZ501628A (cs)
PL (3) PL185560B1 (cs)
PT (1) PT830338E (cs)
SI (1) SI0830338T1 (cs)
SK (2) SK283507B6 (cs)
WO (1) WO1996040617A1 (cs)

Families Citing this family (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5858736A (en) * 1996-05-17 1999-01-12 E. I. Du Pont De Nemours And Company Preparation of lactams from aliphatic α,ω-dinitriles
IL126999A (en) 1996-07-24 2002-03-10 Warner Lambert Co Pharmaceutical preparations containing isobutylgaba and its history for use in the treatment of pain
WO1999008667A2 (en) * 1997-08-19 1999-02-25 Warner-Lambert Company Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotor stimulants
JP3904452B2 (ja) * 1999-06-10 2007-04-11 ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー モノ−およびジ置換３−プロピルガンマ−アミノ酪酸
ME00921B (me) * 2000-01-27 2012-06-20 Warner Lambert Co Asimetrična sinteza pregabalina
GB2368579A (en) * 2000-10-31 2002-05-08 Parke Davis & Co Ltd Azole pharmaceutical agents
US7169812B2 (en) * 2003-07-01 2007-01-30 Medtronic, Inc. Process for producing injectable gabapentin compositions
EP1543831A1 (en) * 2003-12-18 2005-06-22 Pfizer GmbH Arzneimittelwerk Gödecke Pregabalin composition
DE602005002253T2 (de) * 2004-03-12 2008-05-29 Warner-Lambert Company Llc C1-symmetrische bisphosphinliganden und deren verwendung bei der asymmetrischen synthese von pregabalin
UA82292C2 (uk) * 2004-04-14 2008-03-25 Пфайзер Продактс Инк. Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти)
MXPA06014228A (es) * 2004-06-21 2007-02-14 Warner Lambert Co Preparacion de pregabalina y compuestos relacionados.
CN101160281A (zh) * 2005-04-06 2008-04-09 特瓦制药工业有限公司 结晶形态的普瑞巴林
US7488846B2 (en) * 2005-04-11 2009-02-10 Teva Pharmaceuical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
CN101300224A (zh) * 2005-04-11 2008-11-05 特瓦制药工业有限公司 制备(s)-普瑞巴林的方法
WO2006122259A1 (en) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
EP1879853A1 (en) * 2005-05-10 2008-01-23 Teva Pharmaceutical Industries Ltd Pregabalin free of isobutylglutaric acid and a process for preparation thereof
WO2006121557A1 (en) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
CA2604602A1 (en) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Method for the preparation of pregabalin and salts thereof
EP1802568A1 (en) * 2005-09-19 2007-07-04 Teva Pharmaceutical Industries Ltd. Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the new synthesis of (s)-pregabalin
NL2000281C2 (nl) * 2005-11-02 2007-08-07 Pfizer Prod Inc Vaste farmaceutische samenstellingen die pregabaline bevatten.
BRPI0702865A2 (pt) * 2006-04-24 2012-08-07 Teva Pharma processos para preparaÇço do Ácido 3-isobutilglutÁrico e de (s)- pregabalin, a partir de combinaÇÕes de composiÇÕes com fàrmulas especÍficas para uso na dita preparaÇço
US7462738B2 (en) * 2006-05-24 2008-12-09 Teva Pharmaceutical Industries Ltd. Processes for the preparation of R-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof
WO2007143113A2 (en) 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. The use of enzymatic resolution for the preparation of intermediates of pregabalin
US20080015385A1 (en) * 2006-05-31 2008-01-17 Lilach Hedvati Preparation of (S)-pregabalin-nitrile
CA2657544C (en) 2006-07-12 2013-05-28 Generics [Uk] Limited Process for preparing pregabalin
WO2008062460A2 (en) * 2006-10-06 2008-05-29 Cadila Healthcare Limited Crystalline forms of pregabalin
TW200846308A (en) * 2007-03-22 2008-12-01 Teva Pharma Synthesis of (s)-(+)-3-(aminomethyl)-5-methyl hexanoic acid
WO2008138874A1 (en) * 2007-05-09 2008-11-20 Chemo Ibérica, S.A. Process for preparing (s)-pregabalin by optical resolution of racemic pregabalin
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
US8168828B2 (en) 2007-06-25 2012-05-01 Msn Laboratories, Limited Process for the preparation of pregabalin
WO2009044409A2 (en) * 2007-10-01 2009-04-09 Natco Pharma Limited Novel resolution process for pregabalin
KR20090101462A (ko) * 2007-10-03 2009-09-28 테바 파마슈티컬 인더스트리즈 리미티드 프레가발린-4-엘리미네이트, 프레가발린 5-엘리미네이트, 기준 마커 및 표준물로서의 이들의 용도, 및 이들을 낮은 수준으로 함유하는 프레가발린의 제조 방법
ITMI20072262A1 (it) * 2007-12-03 2009-06-04 Dipharma Francis Srl Procedimento per la preparazione di acido (s)(+)-3-(amminometil)-5-metilesanoico
EP2225199A2 (en) * 2007-12-18 2010-09-08 Watson Pharma Private Limited Improved process for the preparation of (s)-pregabalin
WO2009081208A1 (en) * 2007-12-26 2009-07-02 Generics [Uk] Limited Processes to pregabalin
EP2236496A4 (en) * 2007-12-27 2011-12-14 Toray Finechemicals Co Ltd OPTICALLY ACTIVE 3-AMINOPYRROLIDIN SALT, METHOD FOR THE PREPARATION THEREOF AND METHOD FOR THE RACEMATING OF 3-AMINO-PYROLIDIN
DE112008003594B4 (de) 2008-01-02 2018-04-26 Zhejiang Jiuzhou Pharmaceutical Co., Ltd. Neues Abtrennverfahren von S-3-Aminomethyl-5-Methylhexansäure
WO2009125427A2 (en) * 2008-02-18 2009-10-15 Matrix Laboratories Limited Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid
CA2719892A1 (en) * 2008-04-04 2009-10-08 Generics [Uk] Limited Novel process
EP2110372A1 (en) 2008-04-16 2009-10-21 Chemo Ibérica, S.A. Intermediates for the preparation of Pregabalin and process for their preparation
CN101585778B (zh) * 2008-05-19 2014-08-13 上海臣邦医药科技有限公司 一种普瑞巴林制备方法
US8546112B2 (en) * 2008-05-21 2013-10-01 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
AU2009254931A1 (en) * 2008-06-03 2009-12-10 Generics [Uk] Limited A novel and efficient method for the synthesis of an amino acid
US20100087525A1 (en) * 2008-06-23 2010-04-08 Lilach Hedvati Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester
WO2010061403A2 (en) * 2008-11-26 2010-06-03 Ind-Swift Laboratories Limited Process to prepare highly pure (s)-pregabalin
WO2010070593A2 (en) 2008-12-19 2010-06-24 Pfizer Ireland Pharmaceuticals Malonate esters
IT1394292B1 (it) 2009-05-07 2012-06-06 Dipharma Francis Srl Procedimento per la sintesi di pregabalina
ES2362913B1 (es) 2009-12-24 2012-05-24 Moehs Iberica S.L. Nuevo método para la preparación de (s)-pregabalina.
HUP1000186A2 (en) * 2010-04-08 2011-10-28 Richter Gedeon Nyrt Novel industrial process of preparing (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
US8212072B2 (en) 2010-08-13 2012-07-03 Divi's Laboratories, Ltd. Process for the preparation of pregabalin
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
JP5230847B2 (ja) 2011-04-20 2013-07-10 財団法人乙卯研究所 ケイ素含有カルボン酸誘導体
EP2527319A1 (en) 2011-05-24 2012-11-28 Laboratorios Del. Dr. Esteve, S.A. Crystalline forms of pregabalin and co-formers in the treatment of pain
CN104781264A (zh) 2012-10-18 2015-07-15 有限会社肯菲思 含有硅的羧酸衍生物
EP2916832B1 (en) 2012-11-07 2019-01-16 Hikal Limited A process for the preparation of pregabalin
CN103980144B (zh) * 2014-05-16 2018-08-17 浙江华海药业股份有限公司 一种普瑞巴林中间体母液的套用方法
WO2015189068A1 (en) 2014-06-12 2015-12-17 Siegfried Ltd. Method for the preparation of beta-substituted gamma-amino carboxylic acids
CN104086439B (zh) * 2014-06-30 2018-11-16 浙江华海药业股份有限公司 一种pregabalin中间体拆分剂(R)-(+)-α-苯乙胺的回收方法
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
CN104649919B (zh) * 2015-02-10 2021-02-12 浙江华海药业股份有限公司 一种小颗粒普瑞巴林的制备方法
CN107920987A (zh) 2015-05-26 2018-04-17 艾萨·欧蒂迪 控制延缓释放普瑞巴林
CN105175276A (zh) * 2015-07-25 2015-12-23 安徽东凯生物科技有限公司 一种光学纯(r)-3-氨甲酰甲基-5-甲基己酸的合成方法
CN105061234A (zh) * 2015-08-18 2015-11-18 太仓运通生物化工有限公司 一种制备普瑞巴林的方法
CN105085290A (zh) * 2015-08-18 2015-11-25 太仓运通生物化工有限公司 一种合成普瑞巴林的方法
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
CN111333529A (zh) * 2018-12-19 2020-06-26 北京万全德众医药生物技术有限公司 普瑞巴林的一种制备方法
CN109942446B (zh) * 2019-04-17 2021-09-07 黄冈鲁班药业股份有限公司 一种普瑞巴林的制备方法
WO2022119430A1 (es) 2020-12-04 2022-06-09 Laboratorios Silanes S.A. De C.V. Composición farmacéutica sólida recubierta y estable de un analgésico opioide y un antiepiléptico para el dolor
CN112939809A (zh) * 2020-12-30 2021-06-11 江苏恒沛药物科技有限公司 一种1-氰基-3-甲基丁基丙二酸二乙酯的制备方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2516307A (en) * 1949-01-06 1950-07-25 Gen Mills Inc Vinyl resins plasticized with cyano esters
US3110723A (en) * 1959-08-18 1963-11-12 Rohm & Haas Process for preparing monochlorinated cyanoesters
US3133954A (en) * 1959-08-18 1964-05-19 Rohm & Haas Process for preparing chlorinated cyanoesters
US3444161A (en) * 1965-09-02 1969-05-13 Shionogi Seiyaku Kk Alkyl cyano aluminum compounds and process for introducing a cyano group into an alpha,beta unsaturated carbonyl compound
DE1793347A1 (de) * 1968-09-04 1972-02-03 Dynamit Nobel Ag Verfahren zur Herstellung von substituierten Cyanbuttersaeuren
JPS54100316A (en) * 1978-01-25 1979-08-08 Meiji Seika Kaisha Ltd Preparation of derivative of aminobutyric acid
US4428887A (en) * 1982-07-14 1984-01-31 Monsanto Company Method of producing mono-substituted terminal diesters
DE3227388A1 (de) * 1982-07-22 1984-01-26 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von (alpha)-substituierten ss-dicarbonyl-, ss-cyancarbonyl- und ss-dicyanverbindungen
US4760089A (en) * 1985-09-09 1988-07-26 Smithkline Beckman Corporation Irreversible dopamine-β-hydroxylase inhibitors
US5132451A (en) * 1989-08-25 1992-07-21 Warner-Lambert Company Process for cyclic amino acid anticonvulsant compounds
US5077425A (en) * 1990-04-02 1991-12-31 E. I. Du Pont De Nemours And Company Nitrile-accelerated hydrocarboxylation
US6197819B1 (en) * 1990-11-27 2001-03-06 Northwestern University Gamma amino butyric acid analogs and optical isomers
US5366987A (en) * 1991-08-22 1994-11-22 Warner-Lambert Company Isoxazolyl-substituted alkyl amide ACAT inhibitors
SG48288A1 (en) * 1992-05-20 1998-04-17 Univ Northwestern Gaba and l-glutamic acid analogs for antiseizure treatment

Also Published As

Publication number Publication date
PL185560B1 (pl) 2003-06-30
DE69617948T2 (de) 2002-06-13
AU700091B2 (en) 1998-12-24
EP0830338A1 (en) 1998-03-25
HU229957B1 (hu) 2015-03-30
CZ296895B6 (cs) 2006-07-12
EE04053B1 (et) 2003-06-16
PT830338E (pt) 2002-04-29
US5840956A (en) 1998-11-24
JP3874306B2 (ja) 2007-01-31
AU5792196A (en) 1996-12-30
SK283507B6 (sk) 2003-08-05
HU0500934D0 (en) 2005-12-28
NZ308319A (en) 2000-02-28
PL323795A1 (en) 1998-04-27
US6046353A (en) 2000-04-04
ATE210628T1 (de) 2001-12-15
WO1996040617A1 (en) 1996-12-19
JPH11506726A (ja) 1999-06-15
ES2170231T3 (es) 2002-08-01
NZ501628A (en) 2001-09-28
DK0830338T3 (da) 2002-04-02
CZ384697A3 (cs) 1998-03-18
CA2219150A1 (en) 1996-12-19
GEP19991870B (en) 1999-12-06
HUP9802504A2 (hu) 1999-02-01
MX9708652A (es) 1998-06-30
US5637767A (en) 1997-06-10
HU228194B1 (en) 2013-01-28
PL185425B1 (pl) 2003-05-30
EP0830338B1 (en) 2001-12-12
CZ291147B6 (cs) 2002-12-11
SK164597A3 (en) 1998-05-06
EE9700320A (et) 1998-06-15
CA2219150C (en) 2008-11-18
US20010016665A1 (en) 2001-08-23
HUP9802504A3 (en) 2000-06-28
DE69617948D1 (de) 2002-01-24
SI0830338T1 (en) 2002-04-30
PL185557B1 (pl) 2003-06-30

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