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

Info

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

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
    • C07C227/34—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

Landscapes

  • 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 (fr) 1995-06-07 1996-05-13 Procede de preparation d'acide (s)-3-(aminomethyl)-5-methylhexanoique

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 (fr)
EP (1) EP0830338B1 (fr)
JP (1) JP3874306B2 (fr)
AT (1) ATE210628T1 (fr)
CA (1) CA2219150C (fr)
CZ (2) CZ291147B6 (fr)
DE (1) DE69617948T2 (fr)
DK (1) DK0830338T3 (fr)
EE (1) EE04053B1 (fr)
ES (1) ES2170231T3 (fr)
GE (1) GEP19991870B (fr)
HU (2) HU229957B1 (fr)
NZ (2) NZ501628A (fr)
PL (3) PL185560B1 (fr)
PT (1) PT830338E (fr)
SI (1) SI0830338T1 (fr)
SK (2) SK283507B6 (fr)
WO (1) WO1996040617A1 (fr)

Families Citing this family (71)

* 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
PT934061E (pt) 1996-07-24 2003-10-31 Warner Lambert Co Isobutilgaba e seus derivados para o tratamento da dor
AU9019198A (en) * 1997-08-19 1999-03-08 Warner-Lambert Company Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotor stimulants
CA2374755C (fr) * 1999-06-10 2010-03-30 Warner-Lambert Company Acides 3-propyle gamma-aminobutyriques monosubstitues et disubstitues
KR100549748B1 (ko) * 2000-01-27 2006-02-08 워너-램버트 캄파니 엘엘씨 프레가발린의 비대칭 합성
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 (fr) * 2003-12-18 2005-06-22 Pfizer GmbH Arzneimittelwerk Gödecke Composition de pregabaline
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)
CN102102114B (zh) * 2004-06-21 2013-08-14 沃尼尔·朗伯有限责任公司 普瑞巴林和相关化合物的制备
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
WO2006110783A2 (fr) * 2005-04-11 2006-10-19 Teva Pharmaceutical Industries Ltd. Procede de fabrication de (s)-pregabaline
US7488846B2 (en) * 2005-04-11 2009-02-10 Teva Pharmaceuical Industries Ltd. Pregabalin free of lactam and a process for preparation thereof
EP1879852A1 (fr) * 2005-05-10 2008-01-23 Teva Pharmaceutical Industries Ltd Pregabaline exempte de lactame et son procede de preparation
CA2604602A1 (fr) * 2005-05-10 2006-11-16 Teva Pharmaceutical Industries Ltd. Procede pour preparer de la pregabaline et des sels de celle-ci
MX2007000525A (es) * 2005-05-10 2007-03-28 Teva Pharma Pregabalina libre de acido isobutilglutarico y un proceso para la preparacion de ella.
ATE523484T1 (de) * 2005-05-10 2011-09-15 Teva Pharma Optische lösung a us 3-carbamoylmethyl-5-methyl- hexansäure
WO2007035890A1 (fr) * 2005-09-19 2007-03-29 Teva Pharmaceutical Industries Ltd. Synthese asymetrique de l'acide (s)-(+)-3-(aminomethyl)-5-methylhexanoique
NL2000281C2 (nl) * 2005-11-02 2007-08-07 Pfizer Prod Inc Vaste farmaceutische samenstellingen die pregabaline bevatten.
KR20080016658A (ko) * 2006-04-24 2008-02-21 테바 파마슈티컬 인더스트리즈 리미티드 3-이소부틸글루타르산의 합성 방법
WO2007139933A2 (fr) * 2006-05-24 2007-12-06 Teva Pharmaceutical Industries Ltd. Procédés pour la préparation d'acide r-(+)-3-(carbamoyl méthyl)-5-méthylhexanoïque et de sels de celui-ci
WO2007143152A2 (fr) * 2006-05-31 2007-12-13 Teva Pharmaceutical Industries Ltd. Préparation de (s)-prégabaline nitrile
BRPI0702897A2 (pt) 2006-05-31 2011-03-15 Teva Pharmaceutical Ind Ltda processo para preparar um intermediário de pregabalina
EP2054375A2 (fr) 2006-07-12 2009-05-06 Merck Generics (UK) Limited Procédé de préparation de dérives de gamma-aminoacides
WO2008062460A2 (fr) * 2006-10-06 2008-05-29 Cadila Healthcare Limited Formes cristallines de la prégabaline
EP2021318A2 (fr) * 2007-03-22 2009-02-11 Teva Pharmaceutical Industries Ltd. Synthese de l'acide (s)-(+)-3-(aminomethyl)-5-methylhexanoique
WO2008138874A1 (fr) * 2007-05-09 2008-11-20 Chemo Ibérica, S.A. Procédé de préparation de la (s)-prégabaline par résolution optique de prégabaline racémique
EP1992609A1 (fr) * 2007-05-14 2008-11-19 Dipharma Francis S.r.l. Processus de préparation d'acide (S)(+)-3-(aminomethyl)-5-methylhexanoique
WO2009001372A2 (fr) 2007-06-25 2008-12-31 Manne Satyanarayana Reddy Nouveau procédé pour la préparation de la prégabaline
WO2009044409A2 (fr) * 2007-10-01 2009-04-09 Natco Pharma Limited Nouveau procédé de résolution pour la prégabaline
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
US20100312010A1 (en) * 2007-12-18 2010-12-09 Watson Pharma Private Limited Process for the Preparation of (S)-Pregabalin
EP2222630A1 (fr) * 2007-12-26 2010-09-01 Generics (UK) Limited Procédés de préparation de la prégabaline
US7879903B2 (en) 2007-12-27 2011-02-01 Toray Fine Chemicals Co., Ltd. Optically active 3-aminopyrrolidine salt, process for production thereof, and method for optical resolution of 3-aminopyrrolidine
DE112008003594B4 (de) 2008-01-02 2018-04-26 Zhejiang Jiuzhou Pharmaceutical Co., Ltd. Neues Abtrennverfahren von S-3-Aminomethyl-5-Methylhexansäure
US20110144383A1 (en) * 2008-02-18 2011-06-16 Matrix Laboratories Limited Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid
WO2009122215A1 (fr) * 2008-04-04 2009-10-08 Generics [Uk] Limited Nouveau procédé
EP2110372A1 (fr) 2008-04-16 2009-10-21 Chemo Ibérica, S.A. Intermédiaires pour la préparation de prégabaline et leur procédé de préparation
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
AU2009248750B2 (en) * 2008-05-21 2015-05-21 Sandoz Ag Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester
CN102112436A (zh) * 2008-06-03 2011-06-29 基因里克斯(英国)有限公司 用于合成氨基酸的新的和有效方法
US20100087525A1 (en) * 2008-06-23 2010-04-08 Lilach Hedvati Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester
WO2010061403A2 (fr) * 2008-11-26 2010-06-03 Ind-Swift Laboratories Limited Procédé pour préparer de la (s)-prégabaline très pure
WO2010070593A2 (fr) 2008-12-19 2010-06-24 Pfizer Ireland Pharmaceuticals Esters de malonate
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 (fr) 2010-05-14 2011-11-17 Lupin Limited Synthèse améliorée d'un ester alkylique optiquement pur de l'acide (s) - 3-cyano-5-méthyl-hexanoïque, intermédiaire de la (s)-prégabaline
US8212072B2 (en) 2010-08-13 2012-07-03 Divi's Laboratories, Ltd. Process for the preparation of pregabalin
WO2012025861A1 (fr) 2010-08-23 2012-03-01 Pfizer Manufacturing Ireland Procédé de préparation de dérivés d'acide (s)-3-cyano-5-méthylhexanoïque et de prégabaline
EP2700645A4 (fr) 2011-04-20 2014-09-24 Kemphys Ltd Dérivé d'acide carboxylique contenant du silicium
EP2527319A1 (fr) 2011-05-24 2012-11-28 Laboratorios Del. Dr. Esteve, S.A. Formes cristallines de prégabaline et co-formateurs pour le traitement de la douleur
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 (fr) 2012-11-07 2019-01-16 Hikal Limited Procédé de préparation de prégabaline
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 (fr) 2014-06-12 2015-12-17 Siegfried Ltd. Procédé pour la préparation d'acides gamma-aminocarboxyliques substitués en position bêta
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 (fr) 2014-11-10 2016-05-19 Sandoz Ag Amination réductrice stéréosélective d'aldéhydes alpha-chiraux au moyen d'ω-transaminases pour la synthèse de précurseurs de la prégabaline et du brivaracétam
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
US10561602B2 (en) 2015-05-26 2020-02-18 Isa Odidi Controlled extended release pregabalin
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
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
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
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
EP4230199A4 (fr) 2020-12-04 2024-07-31 Laboratorios Silanes S A De C V Composition pharmaceutique solide recouverte et stable d'un analgésique et d'un antiépileptique contre la douleur
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
CN116041214A (zh) * 2022-11-15 2023-05-02 奥锐特药业股份有限公司 一种普瑞巴林中间体的制备方法及其应用

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
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

Also Published As

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

Similar Documents

Publication Publication Date Title
SK282865B6 (sk) Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej a medziprodukty
US5616793A (en) Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid
EP1250311B1 (fr) Synthese asymetrique de pregabaline
WO2008009897A1 (fr) Procédé de préparation de la prégabaline et de son énantiomère opposé
EP2017273A1 (fr) Processus de préparation énantiosélective de prégabaline
US4297282A (en) Resolution of mercaptopropionic acids
EP1235786B1 (fr) Procede de preparation de composes enrichis sur le plan enantiomorphe
AU700091C (en) Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid
MXPA97008652A (en) Method for making acid (s) -3- (aminomethyl) -5-methylhexane
EP0837843B1 (fr) Procede de preparation des formes enantiomeres de l'acide amino alkylaminophenyl propanoique
JP2000044521A (ja) α―位に第三級炭化水素基を有するアミノ酢酸エステルの製造方法

Legal Events

Date Code Title Description
MK4A Patent expired

Expiry date: 20160513