DE69619809D1 - Verfahren zur herstellung von (s)-3-(aminoethyl)-5-metylhexansäure - Google Patents
Verfahren zur herstellung von (s)-3-(aminoethyl)-5-metylhexansäureInfo
- Publication number
- DE69619809D1 DE69619809D1 DE69619809T DE69619809T DE69619809D1 DE 69619809 D1 DE69619809 D1 DE 69619809D1 DE 69619809 T DE69619809 T DE 69619809T DE 69619809 T DE69619809 T DE 69619809T DE 69619809 D1 DE69619809 D1 DE 69619809D1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbamoylmethyl
- reacting
- methylhexanoic acid
- methylhexanoic
- 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.)
- Expired - Fee Related
Links
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
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/458,950 US5616793A (en) | 1995-06-02 | 1995-06-02 | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
PCT/US1996/005831 WO1996038405A1 (en) | 1995-06-02 | 1996-04-26 | Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69619809D1 true DE69619809D1 (de) | 2002-04-18 |
DE69619809T2 DE69619809T2 (de) | 2002-09-26 |
Family
ID=23822760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69619809T Expired - Fee Related DE69619809T2 (de) | 1995-06-02 | 1996-04-26 | Verfahren zur herstellung von (s)-3-(aminoethyl)-5-metylhexansäure |
Country Status (16)
Country | Link |
---|---|
US (2) | US5616793A (de) |
EP (1) | EP0828704B1 (de) |
JP (1) | JP3965440B2 (de) |
AT (1) | ATE214361T1 (de) |
AU (1) | AU699982B2 (de) |
CZ (1) | CZ297631B6 (de) |
DE (1) | DE69619809T2 (de) |
DK (1) | DK0828704T3 (de) |
EE (1) | EE03964B1 (de) |
ES (1) | ES2173279T3 (de) |
HU (1) | HUP9802090A3 (de) |
NZ (1) | NZ307030A (de) |
PL (1) | PL185034B1 (de) |
PT (1) | PT828704E (de) |
SK (1) | SK283663B6 (de) |
WO (1) | WO1996038405A1 (de) |
Families Citing this family (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1094757C (zh) | 1996-07-24 | 2002-11-27 | 沃尼尔·朗伯公司 | 用于治疗疼痛的异丁基γ-氨基丁酸及其衍生物 |
AU777046B2 (en) * | 2000-01-27 | 2004-09-30 | Warner-Lambert Company Llc | Asymmetric synthesis of pregabalin |
EP1543831A1 (de) * | 2003-12-18 | 2005-06-22 | Pfizer GmbH Arzneimittelwerk Gödecke | Zusammensetzung enthaltend Pregabalin |
RU2335342C2 (ru) * | 2004-03-12 | 2008-10-10 | Уорнер-Ламберт Компани Ллс | C1-симметричные бисфосфиновые лиганды и их применение в асимметрическом синтезе прегабалина |
ME01067B (me) * | 2004-06-21 | 2012-10-20 | Warner Lambert Co | Dobijanje pregabalina i srodnih jedinjenja |
EP1866275A1 (de) * | 2005-04-06 | 2007-12-19 | Teva Pharmaceutical Industries Ltd. | Kristalline formen des pregabalins |
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 |
EP1879852A1 (de) * | 2005-05-10 | 2008-01-23 | Teva Pharmaceutical Industries Ltd | Lactamfreies pregabalin und herstellungsverfahren dafür |
WO2006122258A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Method for the preparation of pregabalin and salts thereof |
ATE523484T1 (de) * | 2005-05-10 | 2011-09-15 | Teva Pharma | Optische lösung a us 3-carbamoylmethyl-5-methyl- hexansäure |
BRPI0605833A (pt) * | 2005-05-10 | 2007-12-18 | Teva Pharma | pregabalina livre de ácido isobutilglutárico e um processo para sua preparação |
CN100410242C (zh) * | 2005-06-23 | 2008-08-13 | 江苏恩华药业股份有限公司 | 普瑞巴林中间体及其制备方法 |
WO2007035789A1 (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 |
NL2000281C2 (nl) | 2005-11-02 | 2007-08-07 | Pfizer Prod Inc | Vaste farmaceutische samenstellingen die pregabaline bevatten. |
CA2646474A1 (en) * | 2006-04-24 | 2007-11-08 | Teva Pharmaceutical Industries Ltd. | Processes for the synthesis of 3-isobutylglutaric acid |
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 |
US20080015385A1 (en) * | 2006-05-31 | 2008-01-17 | Lilach Hedvati | Preparation of (S)-pregabalin-nitrile |
WO2007143113A2 (en) | 2006-05-31 | 2007-12-13 | Teva Pharmaceutical Industries Ltd. | The use of enzymatic resolution for the preparation of intermediates of pregabalin |
ITMI20061297A1 (it) * | 2006-07-04 | 2008-01-05 | Laboratorio Chimico Int Spa | Procedimento per la preparazione della'acido (r)-(-)-3-(carbamoilmetil)-5-metilesanoico e del pregabalin e intermedi di sintesi |
GB0614133D0 (en) * | 2006-07-15 | 2006-08-23 | Pliva Istrazivanje I Razvoj D | Process for preparing a pharmaceutical compound |
US8097754B2 (en) * | 2007-03-22 | 2012-01-17 | Teva Pharmaceutical Industries Ltd. | Synthesis of (S)-(+)-3-(aminomethyl)-5-methyl hexanoic acid |
WO2008137512A2 (en) * | 2007-05-03 | 2008-11-13 | Dr. Reddy's Laboratories Ltd. | Process for preparing pregabalin via hofmann reaction and crystalline form thereof |
WO2009004643A2 (en) * | 2007-05-08 | 2009-01-08 | Cadila Healthcare Limited | An improved process for preparation of (s)-pregabalin and intermediates thereof |
EP1992609A1 (de) * | 2007-05-14 | 2008-11-19 | Dipharma Francis S.r.l. | Verfahren für die Herstellung einer (S)(+)-3-(Aminomethyl)-5-Methylhexan-Säure |
WO2009046309A2 (en) * | 2007-10-03 | 2009-04-09 | Teva Pharmaceutical Industries Ltd. | Pregabalin -4-eliminate, pregabalin 5-eliminate, their use as reference marker and standard, and method to produce pregabalin containing low levels thereof |
JP5234901B2 (ja) * | 2007-10-04 | 2013-07-10 | 学校法人東京理科大学 | 不斉触媒マイケル反応生成物の製造方法 |
CN101910111B (zh) * | 2007-11-30 | 2013-06-12 | 化学实验室国际股份公司 | 制备取代的γ-氨基酸的方法 |
ITMI20072262A1 (it) * | 2007-12-03 | 2009-06-04 | Dipharma Francis Srl | Procedimento per la preparazione di acido (s)(+)-3-(amminometil)-5-metilesanoico |
WO2009087674A2 (en) * | 2007-12-18 | 2009-07-16 | Watson Pharma Private Limited | Improved process for the preparation of (s)-pregabalin |
WO2009125427A2 (en) * | 2008-02-18 | 2009-10-15 | Matrix Laboratories Limited | Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid |
UA103997C2 (ru) | 2008-05-21 | 2013-12-25 | Сандоз Аг | Способ стереоселективного ферментативного гидролиза эстера 5-метил-3-нитрометилгексановой кислоты |
WO2009158343A1 (en) * | 2008-06-23 | 2009-12-30 | Teva Pharmaceutical Industries, Ltd. | Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester |
WO2010070593A2 (en) | 2008-12-19 | 2010-06-24 | Pfizer Ireland Pharmaceuticals | Malonate esters |
EP2213659A1 (de) | 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 | Zwischenprodukte bei der enantioselektiven Synthese von 3-(Aminomethyl)-5-Methyl-Hexansäure |
CN101987826A (zh) * | 2009-08-04 | 2011-03-23 | 铜陵凯顺生物科技有限公司 | 一种(3s)-3-氨甲基-5-甲基己酸的合成方法 |
CN102126979A (zh) * | 2009-12-15 | 2011-07-20 | 中国科学院成都有机化学有限公司 | 一种光学纯的3-(氨甲酰甲基)-5-甲基己酸的制备方法 |
ES2362913B1 (es) | 2009-12-24 | 2012-05-24 | Moehs Iberica S.L. | Nuevo método para la preparación de (s)-pregabalina. |
WO2011077463A1 (en) * | 2009-12-24 | 2011-06-30 | Msn Laboratories Limited | Process for preparing pregabalin and its intermediate |
WO2011078172A1 (ja) * | 2009-12-25 | 2011-06-30 | 株式会社カネカ | 光学活性3-置換グルタル酸モノアミドの製造法 |
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 |
KR101306585B1 (ko) * | 2011-04-14 | 2013-09-10 | 한국외국어대학교 연구산학협력단 | 프레가발린의 제조방법 |
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 |
WO2013076630A1 (en) | 2011-11-24 | 2013-05-30 | Lupin Limited | Novel process for racemization of an optically active (s)-3-carbamoylmethyl-5-methyl-hexanoic acid to corresponding 3-carbamoylmethyl-5-methyl-hexanoic acid racemate |
CN102863326A (zh) * | 2012-03-20 | 2013-01-09 | 常州制药厂有限公司 | 一种抗癫痫药物中间体的制备方法 |
US9353134B2 (en) * | 2012-10-18 | 2016-05-31 | Kemphys Ltd. | Silicon-containing carboxylic acid derivative |
CN102898320A (zh) * | 2012-10-26 | 2013-01-30 | 浙江省天台县奥锐特药业有限公司 | (3r)-(-)-3-(2-乙酰氨基)-5-甲基己酸的制备方法 |
JP6482465B2 (ja) | 2012-11-07 | 2019-03-13 | ハイカル リミテッド | プレガバリンの調製方法 |
CN102964263B (zh) * | 2012-11-29 | 2014-12-03 | 太仓市茜泾化工有限公司 | 一种(±)-3-(氨甲酰基)-5-甲基己酸的制备方法 |
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 |
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 |
CN104356016B (zh) * | 2014-10-24 | 2019-08-23 | 浙江华海药业股份有限公司 | 一种用回收制备3-异丁基戊二酸单酰胺的方法 |
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 |
CN104496832A (zh) * | 2014-11-21 | 2015-04-08 | 浙江美诺华药物化学有限公司 | 一种普瑞巴林的合成方法 |
CN104557577B (zh) * | 2014-12-26 | 2016-08-17 | 上海臣邦医药科技有限公司 | 高纯度(+)-普瑞巴林和(-)-普瑞巴林的制备方法 |
MX2017009004A (es) | 2015-01-08 | 2018-03-15 | Lee Pharma Ltd | Nuevo proceso para la preparacion del inhibidor de la enzima dipeptidil peptidasa-4 (dpp-4). |
CN104803869A (zh) * | 2015-03-27 | 2015-07-29 | 浙江华海药业股份有限公司 | 一种无溶剂反应制备3-异丁基戊二酸单酰胺的方法 |
CN104803868B (zh) * | 2015-03-27 | 2020-10-02 | 浙江华海药业股份有限公司 | 一种回收3-异丁基戊二酸单酰胺的方法 |
CN104803871B (zh) * | 2015-05-12 | 2021-03-05 | 浙江华海药业股份有限公司 | 一种制备普瑞巴林中间体的方法 |
CN104892441A (zh) * | 2015-05-22 | 2015-09-09 | 浙江华海药业股份有限公司 | 一种制备普瑞巴林异构体r-普瑞巴林的方法 |
JP2018520112A (ja) | 2015-05-26 | 2018-07-26 | オディディ,イサ | 制御持続放出プレガバリン |
WO2017019791A1 (en) | 2015-07-27 | 2017-02-02 | Teva Pharmaceuticals International Gmbh | Synthesis of (s)-pregabalin |
CN105481712A (zh) * | 2015-11-30 | 2016-04-13 | 常州市阳光药业有限公司 | 普瑞巴林中间体拆分母液的消旋回收方法 |
WO2019193607A1 (en) * | 2018-04-04 | 2019-10-10 | Msn Laboratories Private Limited, R&D Center | An improved process for the preparation of pregabalin |
CN108912004B (zh) * | 2018-08-01 | 2021-05-07 | 宏冠生物药业有限公司 | 一种普瑞巴林中间体的合成方法 |
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 |
CN112062689A (zh) * | 2019-06-11 | 2020-12-11 | 太仓市茜泾化工有限公司 | 一种r-3-(氨甲酰基)-5-甲基己酸的制备方法 |
CN113045468A (zh) * | 2019-12-26 | 2021-06-29 | 上虞京新药业有限公司 | 一种布瓦西坦中间体的制备方法 |
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 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2944969A (en) * | 1957-02-06 | 1960-07-12 | Petrolite Corp | Prevention of rust and corrosion |
US3544467A (en) * | 1966-02-07 | 1970-12-01 | Chevron Res | Acid-amide pour point depressants |
US3857879A (en) * | 1967-12-04 | 1974-12-31 | W Abramitis | Amine salts of substituted succinamic acids |
US4024174A (en) * | 1973-12-25 | 1977-05-17 | Ono Pharmaceutical Company | Tranes-delta 2-prostaglandins |
US4123438A (en) * | 1975-03-05 | 1978-10-31 | Stamicarbon, B.V. | Process for preparing 2-pyrrolidones |
US4739114A (en) * | 1982-09-30 | 1988-04-19 | Rhone-Poulenc Agrochimie | Process for the preparation of 3-alkyl-substituted glutaric acids and 2-alkyl-substituted succinic acids |
US4711671A (en) * | 1985-10-03 | 1987-12-08 | National Starch And Chemical Corporation | Storage stable paper size composition containing ethoxylated lanolin |
DE4033259A1 (de) * | 1990-10-19 | 1992-04-23 | Basf Ag | Verfahren zur herstellung von 2-pyrrolidinonen |
JP3856816B2 (ja) * | 1992-05-20 | 2006-12-13 | ノースウェスターン ユニヴァーシティ | 抗発作治療用のgaba及びl−グルタミン酸類縁体 |
-
1995
- 1995-06-02 US US08/458,950 patent/US5616793A/en not_active Expired - Lifetime
-
1996
- 1996-04-26 DK DK96913186T patent/DK0828704T3/da active
- 1996-04-26 ES ES96913186T patent/ES2173279T3/es not_active Expired - Lifetime
- 1996-04-26 PL PL96323563A patent/PL185034B1/pl unknown
- 1996-04-26 SK SK1621-97A patent/SK283663B6/sk not_active IP Right Cessation
- 1996-04-26 HU HU9802090A patent/HUP9802090A3/hu unknown
- 1996-04-26 EE EE9700311A patent/EE03964B1/xx not_active IP Right Cessation
- 1996-04-26 DE DE69619809T patent/DE69619809T2/de not_active Expired - Fee Related
- 1996-04-26 PT PT96913186T patent/PT828704E/pt unknown
- 1996-04-26 EP EP96913186A patent/EP0828704B1/de not_active Expired - Lifetime
- 1996-04-26 CZ CZ0374297A patent/CZ297631B6/cs not_active IP Right Cessation
- 1996-04-26 AU AU55778/96A patent/AU699982B2/en not_active Ceased
- 1996-04-26 AT AT96913186T patent/ATE214361T1/de not_active IP Right Cessation
- 1996-04-26 JP JP53647696A patent/JP3965440B2/ja not_active Expired - Fee Related
- 1996-04-26 NZ NZ307030A patent/NZ307030A/xx unknown
- 1996-04-26 WO PCT/US1996/005831 patent/WO1996038405A1/en not_active Application Discontinuation
- 1996-06-28 US US08/672,783 patent/US5629447A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
NZ307030A (en) | 1999-02-25 |
CZ374297A3 (cs) | 1998-10-14 |
DE69619809T2 (de) | 2002-09-26 |
PL323563A1 (en) | 1998-04-14 |
CZ297631B6 (cs) | 2007-02-14 |
US5629447A (en) | 1997-05-13 |
WO1996038405A1 (en) | 1996-12-05 |
ATE214361T1 (de) | 2002-03-15 |
HUP9802090A3 (en) | 1999-08-30 |
PT828704E (pt) | 2002-08-30 |
EE03964B1 (et) | 2003-02-17 |
PL185034B1 (pl) | 2003-02-28 |
AU5577896A (en) | 1996-12-18 |
SK162197A3 (en) | 1998-10-07 |
JPH11506098A (ja) | 1999-06-02 |
US5616793A (en) | 1997-04-01 |
JP3965440B2 (ja) | 2007-08-29 |
EP0828704B1 (de) | 2002-03-13 |
HUP9802090A2 (hu) | 1998-12-28 |
EE9700311A (et) | 1998-06-15 |
ES2173279T3 (es) | 2002-10-16 |
SK283663B6 (sk) | 2003-11-04 |
DK0828704T3 (da) | 2002-07-01 |
AU699982B2 (en) | 1998-12-17 |
EP0828704A1 (de) | 1998-03-18 |
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