PT830338E - Metodo para a preparacao de acido (s)-3-(aminometil)-5-metilhexanoico - Google Patents
Metodo para a preparacao de acido (s)-3-(aminometil)-5-metilhexanoicoInfo
- Publication number
- PT830338E PT830338E PT96914618T PT96914618T PT830338E PT 830338 E PT830338 E PT 830338E PT 96914618 T PT96914618 T PT 96914618T PT 96914618 T PT96914618 T PT 96914618T PT 830338 E PT830338 E PT 830338E
- Authority
- PT
- Portugal
- 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT830338E true PT830338E (pt) | 2002-04-29 |
Family
ID=23885291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT96914618T PT830338E (pt) | 1995-06-07 | 1996-05-13 | Metodo para a preparacao de acido (s)-3-(aminometil)-5-metilhexanoico |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US5637767A (pt) |
| EP (1) | EP0830338B1 (pt) |
| JP (1) | JP3874306B2 (pt) |
| AT (1) | ATE210628T1 (pt) |
| CA (1) | CA2219150C (pt) |
| CZ (2) | CZ291147B6 (pt) |
| DE (1) | DE69617948T2 (pt) |
| DK (1) | DK0830338T3 (pt) |
| EE (1) | EE04053B1 (pt) |
| ES (1) | ES2170231T3 (pt) |
| GE (1) | GEP19991870B (pt) |
| HU (2) | HU229957B1 (pt) |
| NZ (2) | NZ501628A (pt) |
| PL (3) | PL185425B1 (pt) |
| PT (1) | PT830338E (pt) |
| SI (1) | SI0830338T1 (pt) |
| SK (2) | SK283507B6 (pt) |
| WO (1) | WO1996040617A1 (pt) |
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 |
| AU714980B2 (en) | 1996-07-24 | 2000-01-13 | Warner-Lambert Company Llc | 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 |
| IL146969A0 (en) * | 1999-06-10 | 2002-08-14 | Warner Lambert Co | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| RS50257B (sr) * | 2000-01-27 | 2009-07-15 | Warner-Lambert Company Llc., | 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 |
| PL1727620T3 (pl) * | 2004-03-12 | 2007-12-31 | Warner Lambert Co | C1-symetryczne ligandy bifosfin i ich zastosowanie w asymetrycznej syntezie pregabaliny |
| UA82292C2 (uk) * | 2004-04-14 | 2008-03-25 | Пфайзер Продактс Инк. | Спосіб стереоселективного біоперетворення аліфатичних динітрилів в ціанокарбонові кислоти (варіанти) |
| HRP20100054T1 (hr) * | 2004-06-21 | 2010-05-31 | Warner-Lambert Company Llc | Dobivanje pregabalina i njemu sličnih spojeva |
| WO2006108151A1 (en) * | 2005-04-06 | 2006-10-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of pregabalin |
| US7488846B2 (en) * | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| MX2007012606A (es) * | 2005-04-11 | 2008-01-11 | Teva Pharma | Proceso para elaborar (s)-pregabalina. |
| BRPI0605833A (pt) * | 2005-05-10 | 2007-12-18 | Teva Pharma | pregabalina livre de ácido isobutilglutárico e um processo para sua preparação |
| EP1879854B1 (en) * | 2005-05-10 | 2011-09-07 | Teva Pharmaceutical Industries Ltd | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
| US7763749B2 (en) * | 2005-05-10 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Method for the preparation of Pregabalin and salts thereof |
| WO2006121557A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| ES2398579T3 (es) * | 2005-09-19 | 2013-03-20 | Teva Pharmaceutical Industries Ltd | Una síntesis asimétrica de ácido (S)-(+)-3-(aminometil)-5-metilhexanoico |
| 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 (en) * | 2006-05-24 | 2007-12-06 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of r-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof |
| EP2071032A3 (en) | 2006-05-31 | 2009-07-08 | Teva Pharmaceutical Industries Ltd | The 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 |
| KR101036536B1 (ko) * | 2007-03-22 | 2011-05-24 | 테바 파마슈티컬 인더스트리즈 리미티드 | (ｓ)-(+)-3-(아미노메틸)-5-메틸 헥산산의 합성 |
| 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 |
| 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 |
| 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 |
| EP2222630A1 (en) * | 2007-12-26 | 2010-09-01 | Generics (UK) Limited | Processes to pregabalin |
| KR101489267B1 (ko) | 2007-12-27 | 2015-02-04 | 도오레 화인케미칼 가부시키가이샤 | 광학 활성 3-아미노피롤리딘염, 그 제조 방법 및 3-아미노피롤리딘의 광학 분할 방법 |
| 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 |
| 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 |
| CN102099482B (zh) * | 2008-05-21 | 2014-04-16 | 桑多斯股份公司 | 5-甲基-3-硝基甲基-己酸酯的立体选择性酶水解方法 |
| EP2280930A1 (en) * | 2008-06-03 | 2011-02-09 | Generics [UK] Limited | A 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 |
| 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 |
| EP4230199A4 (en) | 2020-12-04 | 2024-07-31 | Laboratorios Silanes, S.A. de C.V. | COATED AND STABLE SOLID PHARMACEUTICAL COMPOSITION OF AN ANALGESIC AND AN ANTIEPILEPTIC AGAINST 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 |
| ES2165857T3 (es) * | 1992-05-20 | 2002-04-01 | Univ Northwestern | Analogos de gaba y acido l-glutamico para el tratamiento de trastornos del sistema nervioso central. |
-
1995
- 1995-06-07 US US08/474,874 patent/US5637767A/en not_active Expired - Lifetime
-
1996
- 1996-05-13 DK DK96914618T patent/DK0830338T3/da active
- 1996-05-13 EP EP96914618A patent/EP0830338B1/en not_active Expired - Lifetime
- 1996-05-13 SK SK606-2002A patent/SK283507B6/sk not_active IP Right Cessation
- 1996-05-13 ES ES96914618T patent/ES2170231T3/es not_active Expired - Lifetime
- 1996-05-13 PL PL96323795A patent/PL185425B1/pl unknown
- 1996-05-13 NZ NZ501628A patent/NZ501628A/en not_active IP Right Cessation
- 1996-05-13 JP JP50055997A patent/JP3874306B2/ja not_active Expired - Lifetime
- 1996-05-13 EE EE9700320A patent/EE04053B1/xx unknown
- 1996-05-13 SI SI9630390T patent/SI0830338T1/xx unknown
- 1996-05-13 HU HU0500934A patent/HU229957B1/hu 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 WO PCT/US1996/006819 patent/WO1996040617A1/en not_active Ceased
- 1996-05-13 PT PT96914618T patent/PT830338E/pt unknown
- 1996-05-13 GE GEAP19964087A patent/GEP19991870B/en unknown
- 1996-05-13 SK SK1645-97A patent/SK282865B6/sk not_active IP Right Cessation
- 1996-05-13 AT AT96914618T patent/ATE210628T1/de active
- 1996-05-13 PL PL96350438A patent/PL185557B1/pl unknown
- 1996-05-13 PL PL96350439A patent/PL185560B1/pl unknown
- 1996-05-13 CA CA002219150A patent/CA2219150C/en not_active Expired - Lifetime
- 1996-05-13 NZ NZ308319A patent/NZ308319A/en not_active IP Right Cessation
- 1996-05-13 HU HU9802504A patent/HU228194B1/hu unknown
- 1996-05-13 DE DE69617948T patent/DE69617948T2/de not_active Expired - Lifetime
-
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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