ATE195973T1 - Enzymatische verfahren zur resolution von enantiomeren-mischungen nützlich wie zwischenprodukte zur herstellung von taxanen - Google Patents
Enzymatische verfahren zur resolution von enantiomeren-mischungen nützlich wie zwischenprodukte zur herstellung von taxanenInfo
- Publication number
- ATE195973T1 ATE195973T1 AT93300241T AT93300241T ATE195973T1 AT E195973 T1 ATE195973 T1 AT E195973T1 AT 93300241 T AT93300241 T AT 93300241T AT 93300241 T AT93300241 T AT 93300241T AT E195973 T1 ATE195973 T1 AT E195973T1
- Authority
- AT
- Austria
- Prior art keywords
- taxanes
- resolution
- production
- intermediate products
- enzymatic process
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US82201592A | 1992-01-15 | 1992-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
ATE195973T1 true ATE195973T1 (de) | 2000-09-15 |
Family
ID=25234887
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT93300241T ATE195973T1 (de) | 1992-01-15 | 1993-01-15 | Enzymatische verfahren zur resolution von enantiomeren-mischungen nützlich wie zwischenprodukte zur herstellung von taxanen |
AT99124119T ATE280240T1 (de) | 1992-01-15 | 1993-01-15 | Enzymatische verfahren zur aüftrennüng von enantiomeren-mischungen nützlich als zwischenprodukte zur herstellung von taxanen |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT99124119T ATE280240T1 (de) | 1992-01-15 | 1993-01-15 | Enzymatische verfahren zur aüftrennüng von enantiomeren-mischungen nützlich als zwischenprodukte zur herstellung von taxanen |
Country Status (11)
Country | Link |
---|---|
US (2) | US5567614A (de) |
EP (2) | EP0552041B1 (de) |
JP (1) | JP3184350B2 (de) |
AT (2) | ATE195973T1 (de) |
CA (2) | CA2087359A1 (de) |
DE (2) | DE69329304T2 (de) |
DK (2) | DK1001036T3 (de) |
ES (2) | ES2149800T3 (de) |
GR (1) | GR3034942T3 (de) |
HK (1) | HK1027130A1 (de) |
PT (2) | PT552041E (de) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6335362B1 (en) * | 1991-09-23 | 2002-01-01 | Florida State University | Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them |
US6521660B2 (en) | 1991-09-23 | 2003-02-18 | Florida State University | 3′-alkyl substituted taxanes and pharmaceutical compositions containing them |
US6005138A (en) | 1991-09-23 | 1999-12-21 | Florida State University | Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them |
DK1001036T3 (da) * | 1992-01-15 | 2004-11-29 | Squibb & Sons Inc | Enzymatiske fremgangsmåder til spaltning af enantiomerblandinger af forbindelser, der er nyttige som mellemprodukter ved fremstillingen af taxaner |
US5646176A (en) | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
TW397866B (en) | 1993-07-14 | 2000-07-11 | Bristol Myers Squibb Co | Enzymatic processes for the resolution of enantiomeric mixtures of compounds useful as intermediates in the preparation of taxanes |
DE4420751A1 (de) * | 1994-06-15 | 1995-12-21 | Basf Ag | Verfahren zur Herstellung von enantiomerenreinen Lactamen |
US5602272A (en) * | 1994-06-21 | 1997-02-11 | Bristol-Myers Squibb Company | Reduction and resolution methods for the preparation of compounds useful as intemediates for preparing taxanes |
US6201140B1 (en) | 1994-07-28 | 2001-03-13 | Bristol-Myers Squibb Company | 7-0-ethers of taxane derivatives |
US5523233A (en) * | 1995-05-03 | 1996-06-04 | Merck & Co., Inc. | Enzymatic hydrolysis of 3,3-diethyl-4-[(4-carboxy)phenoxy]-2-azetidinone esters |
US5635531A (en) * | 1996-07-08 | 1997-06-03 | Bristol-Myers Squibb Company | 3'-aminocarbonyloxy paclitaxels |
EP1308519B1 (de) * | 1997-01-24 | 2006-04-19 | Sumitomo Chemical Company, Limited | Verfahren zur Verbesserung der optischen Aktivität von Azetidin-2-carbonsäure |
GB9714877D0 (en) * | 1997-07-15 | 1997-09-17 | Chiroscience Ltd | Microorganism and its use |
EP0933360A1 (de) | 1997-12-22 | 1999-08-04 | Pharmachemie B.V. | Synthese von Beta-lactamen |
US5919672A (en) * | 1998-10-02 | 1999-07-06 | Schering Corporation | Resolution of trans-2-(alkoxycarbonylethyl)-lactams useful in the synthesis of 1-(4-fluoro-phenyl)-3(R)- (S)-hydroxy-3-(4-fluorophenyl)-propyl!-4(S)-(4-hydroxyphenyl)-2-azetidinone |
KR100567108B1 (ko) * | 1999-07-16 | 2006-03-31 | 에스케이 주식회사 | 효소적 방법에 의한 트랜스-(1s,2s)-1-아지도 2-인단올 및 트랜스-(1r,2r)-1-아지도 2-인다닐 아세테이트의 제조방법 |
CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
US6548293B1 (en) | 1999-10-18 | 2003-04-15 | Fsu Research Foundation, Inc. | Enzymatic process for the resolution of enantiomeric mixtures of β-lactams |
JP2003522171A (ja) | 2000-02-02 | 2003-07-22 | フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド | 抗腫瘍剤としてのc10カーボネート置換タキサン |
BR0104351A (pt) | 2000-02-02 | 2002-01-02 | Univ Florida State Res Found | Taxanos substituìdos com carbonato c7 como agentes antitumor |
DE60131927D1 (de) * | 2000-02-02 | 2008-01-31 | Univ Florida State Res Found | Heterosubstituierte taxan-c10-acetate als antitumormittel |
CO5280224A1 (es) * | 2000-02-02 | 2003-05-30 | Univ Florida State Res Found | Taxanos sustituidos con ester en c7, utiles como agentes antitumorales y composiciones farmaceuticas que los contienen |
US6649632B2 (en) * | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
EP1165551B1 (de) * | 2000-02-02 | 2008-07-16 | Florida State University Research Foundation, Inc. | C10-carbamoyloxysubstituierte taxane als antitumormittel |
HUP0200752A3 (en) | 2000-02-02 | 2005-02-28 | Univ Florida State Res Found | C7 carbamoyloxy substituted taxanes as antitumor agents |
KR20010112393A (ko) * | 2000-02-02 | 2001-12-20 | 플로리다 스테이트 유니버시티 리서치 파운데이션, 인크 | 항종양제로서 c7 헤테로치환된 아세테이트 탁산 |
DE10004926A1 (de) * | 2000-02-04 | 2001-08-09 | Gruenenthal Gmbh | Verfahren zur enzymatischen Racematspaltung von Aminomethyl-Aryl-Cyclohexanol-Derivaten |
ES2284613T3 (es) * | 2000-02-11 | 2007-11-16 | Shire Biochem Inc. | Sintesis estereoselectiva de analogos de nucleosido. |
WO2002070512A1 (fr) * | 2001-03-07 | 2002-09-12 | Daiichi Pharmaceutical Co, Ltd. | Procede de fabrication d'un derive d'azetidinone-2 |
US6653501B2 (en) | 2001-06-27 | 2003-11-25 | Napro Biotherapeutics, Inc. | Chiral resolution method for producing compounds useful in the synthesis of taxanes |
US7063977B2 (en) * | 2001-08-21 | 2006-06-20 | Bristol-Myers Squibb Company | Enzymatic resolution of t-butyl taxane derivatives |
MXPA04005038A (es) | 2001-11-30 | 2004-08-11 | Bristol Myers Squibb Co | Solvatos de paclitaxel. |
KR100433633B1 (ko) * | 2002-04-18 | 2004-05-31 | 학교법인 포항공과대학교 | 무용매 이상계 시스템을 이용한 효소적 광학분할 방법 |
US7064980B2 (en) * | 2003-09-17 | 2006-06-20 | Sandisk Corporation | Non-volatile memory and method with bit line coupled compensation |
HN2005000054A (es) * | 2004-02-13 | 2009-02-18 | Florida State University Foundation Inc | Taxanos sustituidos con esteres de ciclopentilo en c10 |
AR048078A1 (es) | 2004-03-05 | 2006-03-29 | Univ Florida State Res Found | Taxanos con sustituyente lactiloxilo en el c7 |
PE20061090A1 (es) * | 2005-02-14 | 2006-10-12 | Univ Florida State Res Found | Preparaciones de taxanos sustituidos con esteres de ciclopropilo en c10 |
WO2009118750A1 (en) * | 2008-03-26 | 2009-10-01 | Council Of Scientific & Industrial Research | Stereoselective hydrolysis for the resolution of racemic mixtures of (+/-) -cis-s-acetoxy-l- (4-methoxyphenyl) -4- (2-furyl) -2-azetidinone, (+/-) -cis-s-acetoxy-l- (4-methoxyphenyl) -4- (2-thienyl) -2-azetidinone, or |
US8242166B2 (en) * | 2008-03-31 | 2012-08-14 | Florida State University Research Foundation, Inc. | C(10) ethyl ester and C(10) cyclopropyl ester substituted taxanes |
Family Cites Families (31)
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US4492757A (en) * | 1981-12-28 | 1985-01-08 | Denki Kagaku Kogyo Kabushiki Kaisha | Process for preparing L-threonine |
JPS60248192A (ja) * | 1984-05-23 | 1985-12-07 | Sumitomo Chem Co Ltd | 光学活性なスレオ−3−フエニルセリン誘導体の製造方法 |
FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
US4876399A (en) * | 1987-11-02 | 1989-10-24 | Research Corporation Technologies, Inc. | Taxols, their preparation and intermediates thereof |
US4942184A (en) * | 1988-03-07 | 1990-07-17 | The United States Of America As Represented By The Department Of Health And Human Services | Water soluble, antineoplastic derivatives of taxol |
FR2629819B1 (fr) * | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
US4943528A (en) * | 1988-11-22 | 1990-07-24 | Nitto Chemical Industry Co., Ltd. | Process for the production of optically active (R)-(-)-3-halo-1,2-propanediol |
US4960790A (en) * | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
CA2012364A1 (en) * | 1989-04-01 | 1990-10-01 | Fumio Moriuchi | Optically active compound and process for preparing the same |
KR920701469A (ko) * | 1989-05-15 | 1992-08-11 | 스테이너 브이. 캔스태드 | 향균성 화합물 및 이의 중간물질의 제조방법 |
US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
CA2019484A1 (en) * | 1989-06-21 | 1990-12-21 | Joseph E. Lynch | Nitrogen deprotected 4-acyloxyazetidin-2-ones |
CA2023645C (fr) * | 1989-08-23 | 2002-03-26 | Jean-Noel Denis | Procede pour la preparation enantioselective de derives de la phenylisoserine |
US5241064A (en) * | 1989-10-02 | 1993-08-31 | Fujisawa Pharmaceutical Co., Ltd. | Enzymatic process for preparing optically active 3-substituted azetidinones |
US5136060A (en) * | 1989-11-14 | 1992-08-04 | Florida State University | Method for preparation of taxol using an oxazinone |
US5015744A (en) * | 1989-11-14 | 1991-05-14 | Florida State University | Method for preparation of taxol using an oxazinone |
CA2071160A1 (en) * | 1991-07-31 | 1993-02-01 | Vittorio Farina | Asymmetric synthesis of taxol side chain |
EP0529483B1 (de) * | 1991-08-22 | 1996-02-28 | Lonza Ag | Verfahren zur Herstellung von optisch aktiven 4-Amino-3-hydroxycarbonsäuren |
US5250683A (en) * | 1991-09-23 | 1993-10-05 | Florida State University | Certain substituted taxanes and pharmaceutical compositions containing them |
US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
US5227400A (en) * | 1991-09-23 | 1993-07-13 | Florida State University | Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them |
DK1001036T3 (da) * | 1992-01-15 | 2004-11-29 | Squibb & Sons Inc | Enzymatiske fremgangsmåder til spaltning af enantiomerblandinger af forbindelser, der er nyttige som mellemprodukter ved fremstillingen af taxaner |
US5272171A (en) * | 1992-02-13 | 1993-12-21 | Bristol-Myers Squibb Company | Phosphonooxy and carbonate derivatives of taxol |
US5294637A (en) * | 1992-07-01 | 1994-03-15 | Bristol-Myers Squibb Company | Fluoro taxols |
US5254580A (en) * | 1993-01-19 | 1993-10-19 | Bristol-Myers Squibb Company | 7,8-cyclopropataxanes |
EP0582469A2 (de) * | 1992-08-06 | 1994-02-09 | Wisconsin Alumni Research Foundation | Verfahren zur Herstellung von Taxol-Typ-Verbindungen vom Beta-Laktam-Vorläufer |
NO310238B1 (no) * | 1992-12-24 | 2001-06-11 | Bristol Myers Squibb Co | Kjemiske forbindelser og farmasöytisk preparat samt anvendelse av slike preparater |
US5516676A (en) * | 1993-06-15 | 1996-05-14 | Bristol-Myers Squibb Company | Preparation of C-13 hydroxyl-bearing taxanes using nocardioides or a hydrolase isolated therefrom |
US5523219A (en) * | 1993-06-15 | 1996-06-04 | Bristol-Myers Squibb Company | Enzymatic hydrolysis method for the preparation of C-10 hydroxyl-bearing taxanes and enzymatic esterification method for the preparation of C-10 acyloxy-bearing |
-
1993
- 1993-01-15 DK DK99124119T patent/DK1001036T3/da active
- 1993-01-15 EP EP93300241A patent/EP0552041B1/de not_active Expired - Lifetime
- 1993-01-15 PT PT93300241T patent/PT552041E/pt unknown
- 1993-01-15 ES ES93300241T patent/ES2149800T3/es not_active Expired - Lifetime
- 1993-01-15 PT PT99124119T patent/PT1001036E/pt unknown
- 1993-01-15 AT AT93300241T patent/ATE195973T1/de not_active IP Right Cessation
- 1993-01-15 EP EP99124119A patent/EP1001036B1/de not_active Expired - Lifetime
- 1993-01-15 ES ES99124119T patent/ES2230790T3/es not_active Expired - Lifetime
- 1993-01-15 DE DE69329304T patent/DE69329304T2/de not_active Expired - Fee Related
- 1993-01-15 DK DK93300241T patent/DK0552041T3/da active
- 1993-01-15 DE DE69333675T patent/DE69333675T2/de not_active Expired - Fee Related
- 1993-01-15 CA CA002087359A patent/CA2087359A1/en not_active Abandoned
- 1993-01-15 AT AT99124119T patent/ATE280240T1/de not_active IP Right Cessation
- 1993-01-15 CA CA002434312A patent/CA2434312A1/en not_active Abandoned
- 1993-01-18 JP JP00573493A patent/JP3184350B2/ja not_active Expired - Fee Related
-
1994
- 1994-05-23 US US08/247,789 patent/US5567614A/en not_active Expired - Lifetime
-
1996
- 1996-08-01 US US08/691,058 patent/US5811292A/en not_active Expired - Fee Related
-
2000
- 2000-09-28 HK HK00106189A patent/HK1027130A1/xx not_active IP Right Cessation
- 2000-11-30 GR GR20000402521T patent/GR3034942T3/el not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE69333675D1 (de) | 2004-11-25 |
HK1027130A1 (en) | 2001-01-05 |
DE69329304D1 (de) | 2000-10-05 |
PT1001036E (pt) | 2005-01-31 |
EP1001036A2 (de) | 2000-05-17 |
PT552041E (pt) | 2000-12-29 |
DK1001036T3 (da) | 2004-11-29 |
EP0552041A3 (en) | 1994-10-05 |
JP3184350B2 (ja) | 2001-07-09 |
DE69329304T2 (de) | 2001-01-04 |
ATE280240T1 (de) | 2004-11-15 |
ES2149800T3 (es) | 2000-11-16 |
EP1001036A3 (de) | 2000-08-02 |
US5811292A (en) | 1998-09-22 |
DE69333675T2 (de) | 2006-02-02 |
JPH05308996A (ja) | 1993-11-22 |
US5567614A (en) | 1996-10-22 |
ES2230790T3 (es) | 2005-05-01 |
GR3034942T3 (en) | 2001-02-28 |
CA2087359A1 (en) | 1993-07-16 |
DK0552041T3 (da) | 2000-10-09 |
EP1001036B1 (de) | 2004-10-20 |
CA2434312A1 (en) | 1993-07-16 |
EP0552041A2 (de) | 1993-07-21 |
EP0552041B1 (de) | 2000-08-30 |
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