EE04053B1 - (S)-3-(aminometüül)-5-metüülheksaanhappe valmistamise meetod - Google Patents
(S)-3-(aminometüül)-5-metüülheksaanhappe valmistamise meetodInfo
- Publication number
- EE04053B1 EE04053B1 EE9700320A EE9700320A EE04053B1 EE 04053 B1 EE04053 B1 EE 04053B1 EE 9700320 A EE9700320 A EE 9700320A EE 9700320 A EE9700320 A EE 9700320A EE 04053 B1 EE04053 B1 EE 04053B1
- Authority
- EE
- Estonia
- Prior art keywords
- aminomethyl
- methylhexanoic acid
- alkali
- earth metal
- alkaline earth
- Prior art date
Links
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 8
- 239000003513 alkali Substances 0.000 abstract 5
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 abstract 4
- -1 alkaline earth metal carboxylate salt Chemical class 0.000 abstract 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 2
- 230000000911 decarboxylating effect Effects 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
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)
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 |
|---|---|
| EE9700320A EE9700320A (et) | 1998-06-15 |
| EE04053B1 true EE04053B1 (et) | 2003-06-16 |
Family
ID=23885291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EE9700320A EE04053B1 (et) | 1995-06-07 | 1996-05-13 | (S)-3-(aminometüül)-5-metüülheksaanhappe valmistamise meetod |
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) | CZ291147B6 (cs) |
| DE (1) | DE69617948T2 (cs) |
| DK (1) | DK0830338T3 (cs) |
| EE (1) | EE04053B1 (cs) |
| ES (1) | ES2170231T3 (cs) |
| GE (1) | GEP19991870B (cs) |
| HU (2) | HU228194B1 (cs) |
| NZ (2) | NZ308319A (cs) |
| PL (3) | PL185557B1 (cs) |
| PT (1) | PT830338E (cs) |
| SI (1) | SI0830338T1 (cs) |
| SK (2) | SK282865B6 (cs) |
| WO (1) | WO1996040617A1 (cs) |
Families Citing this family (71)
| 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 |
| DK0934061T6 (en) | 1996-07-24 | 2015-01-26 | Warner Lambert Co | Isobutylgaba and its derivatives for the treatment of pain |
| US6194459B1 (en) | 1997-08-19 | 2001-02-27 | Warner-Lambert Company | Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotors stimulants |
| AU776723C (en) * | 1999-06-10 | 2005-06-02 | Warner-Lambert Company Llc | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| 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 (en) * | 2003-12-18 | 2005-06-22 | Pfizer GmbH Arzneimittelwerk Gödecke | Pregabalin composition |
| RU2335342C2 (ru) * | 2004-03-12 | 2008-10-10 | Уорнер-Ламберт Компани Ллс | C1-симметричные бисфосфиновые лиганды и их применение в асимметрическом синтезе прегабалина |
| UA82292C2 (uk) * | 2004-04-14 | 2008-03-25 | Пфайзер Продактс Инк. | Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти) |
| KR100847929B1 (ko) * | 2004-06-21 | 2008-07-22 | 워너-램버트 캄파니 엘엘씨 | 프레가발린 및 관련 화합물의 제조방법 |
| EP1866275A1 (en) * | 2005-04-06 | 2007-12-19 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of pregabalin |
| MX2007012606A (es) * | 2005-04-11 | 2008-01-11 | Teva Pharma | Proceso para elaborar (s)-pregabalina. |
| US7488846B2 (en) * | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| CA2604624A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
| JP2008505980A (ja) * | 2005-05-10 | 2008-02-28 | テバ ファーマシューティカル インダストリーズ リミティド | イソブチルグルタル酸を有さないプレガバリン及びその調製方法 |
| KR100893312B1 (ko) * | 2005-05-10 | 2009-04-15 | 테바 파마슈티컬 인더스트리즈 리미티드 | 프레가발린 및 이의 염의 제조 방법 |
| EP1879852A1 (en) * | 2005-05-10 | 2008-01-23 | Teva Pharmaceutical Industries Ltd | Pregabalin free of lactam and a process for preparation thereof |
| US7563923B2 (en) * | 2005-09-19 | 2009-07-21 | Teva Pharmaceutical Industries Ltd. | Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key intermediates for the 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 |
| TW200815323A (en) * | 2006-05-24 | 2008-04-01 | Teva Pharma | Processes for the preparation of R-(+)-3-(carbamoylmethyl)-5-methylhexanoic acid and salts thereof |
| US20080026433A1 (en) * | 2006-05-31 | 2008-01-31 | Lilach Hedvati | Use of enzymatic resolution for the preparation of intermediates of pregabalin |
| EP1912931A2 (en) * | 2006-05-31 | 2008-04-23 | Teva Pharmaceutical Industries Ltd. | Preparation of (s)-pregabalin-nitrile |
| WO2008007145A2 (en) | 2006-07-12 | 2008-01-17 | Generics [Uk] Limited | Process of preparing a gamma-amino acid |
| 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 |
| WO2009001372A2 (en) * | 2007-06-25 | 2008-12-31 | Manne Satyanarayana Reddy | A novel 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 |
| US20100312010A1 (en) * | 2007-12-18 | 2010-12-09 | Watson Pharma Private Limited | Process for the Preparation of (S)-Pregabalin |
| JP2011507941A (ja) * | 2007-12-26 | 2011-03-10 | ジェネリクス・（ユーケー）・リミテッド | プレガバリンの製造方法 |
| 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 |
| US8592625B2 (en) * | 2008-01-02 | 2013-11-26 | Zheinjiang Jiuzhou Pharmaceutical Co., Ltd. | Process for resolving S-3-(aminomethyl)-5-methylhexanoic acid |
| WO2009125427A2 (en) * | 2008-02-18 | 2009-10-15 | Matrix Laboratories Limited | Process for preparing (s)-3-(aminomethyl)-5-methylhexanoic acid |
| US20110124909A1 (en) * | 2008-04-04 | 2011-05-26 | Vinayak Gore | 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 |
| CA2724828C (en) * | 2008-05-21 | 2016-01-12 | Sandoz Ag | Process for the stereoselective enzymatic hydrolysis of 5-methyl-3-nitromethyl-hexanoic acid ester |
| US20110190393A1 (en) * | 2008-06-03 | 2011-08-04 | Generics (Uk) Limited | Novel and efficient method for the synthesis of an amino acid |
| WO2009158343A1 (en) * | 2008-06-23 | 2009-12-30 | Teva Pharmaceutical Industries, Ltd. | 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 |
| US9353134B2 (en) * | 2012-10-18 | 2016-05-31 | Kemphys Ltd. | Silicon-containing carboxylic acid derivative |
| US10023885B2 (en) | 2012-11-07 | 2018-07-17 | Hikal Limited | 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 |
| US9745249B2 (en) | 2014-06-12 | 2017-08-29 | 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 |
| 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 |
| 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 |
| US20240000727A1 (en) | 2020-12-04 | 2024-01-04 | Laboratorios Silanes S.A. De C.V. | Stable coated solid pharmaceutical composition of an opioid analgesic and an anti-epileptic for pain |
| 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 |
| CN116041214B (zh) * | 2022-11-15 | 2025-04-22 | 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 |
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|---|---|---|---|---|
| US2516307A (en) * | 1949-01-06 | 1950-07-25 | Gen Mills Inc | Vinyl resins plasticized with cyano esters |
| US3133954A (en) * | 1959-08-18 | 1964-05-19 | Rohm & Haas | Process for preparing chlorinated cyanoesters |
| US3110723A (en) * | 1959-08-18 | 1963-11-12 | Rohm & Haas | Process for preparing monochlorinated 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 |
| HU222339B1 (hu) * | 1992-05-20 | 2003-06-28 | Northwestern University | S-(+)-4-amino-3-(2-metil-propil)-butánsav, és gyógyászati szempontból elfogadható sói, ezeket tartalmazó gyógyászati készítmények, valamint az (S)-(+)-4-amino-3-(2-metil-propil)-butánsav előállítása |
-
1995
- 1995-06-07 US US08/474,874 patent/US5637767A/en not_active Expired - Lifetime
-
1996
- 1996-05-13 NZ NZ308319A patent/NZ308319A/en not_active IP Right Cessation
- 1996-05-13 NZ NZ501628A patent/NZ501628A/en not_active IP Right Cessation
- 1996-05-13 CA CA002219150A patent/CA2219150C/en not_active Expired - Lifetime
- 1996-05-13 EE EE9700320A patent/EE04053B1/xx unknown
- 1996-05-13 PL PL96350438A patent/PL185557B1/pl unknown
- 1996-05-13 JP JP50055997A patent/JP3874306B2/ja not_active Expired - Lifetime
- 1996-05-13 DE DE69617948T patent/DE69617948T2/de not_active Expired - Lifetime
- 1996-05-13 HU HU9802504A patent/HU228194B1/hu unknown
- 1996-05-13 AT AT96914618T patent/ATE210628T1/de active
- 1996-05-13 WO PCT/US1996/006819 patent/WO1996040617A1/en active IP Right Grant
- 1996-05-13 ES ES96914618T patent/ES2170231T3/es not_active Expired - Lifetime
- 1996-05-13 PT PT96914618T patent/PT830338E/pt unknown
- 1996-05-13 CZ CZ19973846A patent/CZ291147B6/cs not_active IP Right Cessation
- 1996-05-13 CZ CZ20010732A patent/CZ296895B6/cs not_active IP Right Cessation
- 1996-05-13 PL PL96323795A patent/PL185425B1/pl unknown
- 1996-05-13 DK DK96914618T patent/DK0830338T3/da active
- 1996-05-13 SK SK1645-97A patent/SK282865B6/sk not_active IP Right Cessation
- 1996-05-13 SI SI9630390T patent/SI0830338T1/xx unknown
- 1996-05-13 HU HU0500934A patent/HU229957B1/hu unknown
- 1996-05-13 SK SK606-2002A patent/SK283507B6/sk not_active IP Right Cessation
- 1996-05-13 EP EP96914618A patent/EP0830338B1/en not_active Expired - Lifetime
- 1996-05-13 PL PL96350439A patent/PL185560B1/pl unknown
- 1996-05-13 GE GEAP19964087A patent/GEP19991870B/en unknown
-
1997
- 1997-02-06 US US08/796,159 patent/US5840956A/en not_active Expired - Lifetime
-
1998
- 1998-08-26 US US09/140,163 patent/US6046353A/en not_active Expired - Lifetime
-
1999
- 1999-10-05 US US09/412,258 patent/US20010016665A1/en not_active Abandoned
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