DE3752257D1 - Verfahren zur Herstellung von 2-Arylpropionsäuren - Google Patents

Verfahren zur Herstellung von 2-Arylpropionsäuren

Info

Publication number
DE3752257D1
DE3752257D1 DE3752257T DE3752257T DE3752257D1 DE 3752257 D1 DE3752257 D1 DE 3752257D1 DE 3752257 T DE3752257 T DE 3752257T DE 3752257 T DE3752257 T DE 3752257T DE 3752257 D1 DE3752257 D1 DE 3752257D1
Authority
DE
Germany
Prior art keywords
compound
optionally substituted
ester
ring system
preparation
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
Application number
DE3752257T
Other languages
English (en)
Other versions
DE3752257T2 (de
Inventor
Mauro Atillio Bertola
Arthur Friedrich Marx
Hein Simon Koger
Wilhelmus Johannes Quax
Der Laken Cornelis Jacobus Van
Gareth Thomas Phillips
Brian William Robertson
Peter Douglas Watts
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Shell Internationale Research Maatschappij BV
Original Assignee
Gist Brocades NV
Shell Internationale Research Maatschappij BV
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 Gist Brocades NV, Shell Internationale Research Maatschappij BV filed Critical Gist Brocades NV
Application granted granted Critical
Publication of DE3752257D1 publication Critical patent/DE3752257D1/de
Publication of DE3752257T2 publication Critical patent/DE3752257T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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
    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • 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
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/83—Arthrobacter
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/832—Bacillus
    • Y10S435/836—Bacillus licheniformis
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/832—Bacillus
    • Y10S435/839—Bacillus subtilis
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/848—Escherichia
    • Y10S435/849—Escherichia coli
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/874—Pseudomonas
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/886—Streptomyces

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Analytical Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Virology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Rheumatology (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DE3752257T 1986-01-07 1987-01-06 Verfahren zur Herstellung von 2-Arylpropionsäuren Expired - Fee Related DE3752257T2 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB868600245A GB8600245D0 (en) 1986-01-07 1986-01-07 Preparation of 2-arylpropionic acids

Publications (2)

Publication Number Publication Date
DE3752257D1 true DE3752257D1 (de) 1999-04-08
DE3752257T2 DE3752257T2 (de) 1999-08-05

Family

ID=10590982

Family Applications (2)

Application Number Title Priority Date Filing Date
DE3752257T Expired - Fee Related DE3752257T2 (de) 1986-01-07 1987-01-06 Verfahren zur Herstellung von 2-Arylpropionsäuren
DE8787200008T Expired - Lifetime DE3780184T2 (de) 1986-01-07 1987-01-06 Mikrobielle esterase und verfahren zur herstellung von 2-arylpropionsaeuren.

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE8787200008T Expired - Lifetime DE3780184T2 (de) 1986-01-07 1987-01-06 Mikrobielle esterase und verfahren zur herstellung von 2-arylpropionsaeuren.

Country Status (20)

Country Link
US (2) US4886750A (de)
EP (2) EP0426656B1 (de)
JP (2) JP2702915B2 (de)
KR (1) KR960016868B1 (de)
CN (1) CN87100031A (de)
AT (2) ATE78054T1 (de)
AU (1) AU591541B2 (de)
CA (2) CA1340382C (de)
DE (2) DE3752257T2 (de)
DK (1) DK172862B1 (de)
ES (2) ES2131503T3 (de)
FI (1) FI90565C (de)
GB (1) GB8600245D0 (de)
GR (2) GR3005735T3 (de)
IE (1) IE61983B1 (de)
IL (1) IL81127A (de)
NO (2) NO169498C (de)
NZ (1) NZ218808A (de)
PT (1) PT84060B (de)
ZA (1) ZA8786B (de)

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US4868214A (en) * 1987-11-17 1989-09-19 Analgesic Associates Onset-hastened/enhanced analgesia
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US5229280A (en) * 1988-02-25 1993-07-20 Istituto Guido Donegani S.P.A. Process for the continuous biotechnological preparation of optical isomer s(+) of 2-(6-methoxy-2-naphthyl) propionic acid
US5316931A (en) * 1988-02-26 1994-05-31 Biosource Genetics Corp. Plant viral vectors having heterologous subgenomic promoters for systemic expression of foreign genes
US6054566A (en) 1988-02-26 2000-04-25 Biosource Technologies, Inc. Recombinant animal viral nucleic acids
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US5196568A (en) * 1988-04-07 1993-03-23 Sepracor, Inc. Compounds useful in enzymatic resolution systems and their preparation
ES2090030T3 (es) * 1988-04-21 1996-10-16 Gist Brocades Nv Procedimiento para producir un acido 2-aril-propionico opticamente activo.
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US5238831A (en) * 1989-04-28 1993-08-24 Gist-Brocades Stabilization of carboxyl esterase
KR100204837B1 (ko) * 1989-04-28 1999-06-15 기스트 브로카데스 나암로제 베노오트하프 카르복실 에스테라제의 안정화
DE3919029A1 (de) * 1989-06-10 1990-12-13 Hoechst Ag Verfahren zur enzymatischen spaltung von 2-arylpropionsaeure-vinylester
EP0412676B1 (de) * 1989-08-07 1995-06-07 Yissum Research Development Company Of The Hebrew University Of Jerusalem Verfahren zur Produktion von der Spiroplasma sp. DNA Methylase
IL95468A0 (en) * 1989-08-24 1991-06-30 Syntex Pharma Int Cloning,expression and sequencing of an ester hydrolase gene in escherichia coli
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IE70430B1 (en) * 1990-02-13 1996-11-27 Lonza Ag Microbiological oxidation of methyl groups in heterocyclic compounds
US5175100A (en) * 1990-02-26 1992-12-29 Rhone-Poulenc, Inc. Stereospecific resolution by hydrolysis of esters of 2-arylpropionic acids by liver enzymes
WO1991013163A1 (en) * 1990-02-26 1991-09-05 Rhone-Poulenc Inc. Stereospecific resolution by hydrolysis of esters of 2-arylpropionic acids by liver enzymes
IT1247533B (it) * 1991-04-26 1994-12-17 Mini Ricerca Scient Tecnolog Processo per la separazione degli isomeri ottici di acidi carbossilici alfa-sostitutivi
US5308765A (en) * 1991-05-15 1994-05-03 Mitsubishi Rayon Co., Ltd. Esterase genes, esterase, recombinant plasmids and transformants containing the recombinant plasmid and methods of producing optically acitve carboxylic acids and their enantiomeric esters using said transformants
EP0536671B1 (de) * 1991-10-07 1996-03-06 Hoechst Aktiengesellschaft Carbonsäureester-Schutzgruppen, ein Verfahren zu ihrer Herstellung, ihre Kopplung an eine funktionelle Gruppe sowie ihre Verwendung
US5273895A (en) * 1992-10-26 1993-12-28 Sepracor, Inc. Enantioselective production of chiral carboxylic acids
US5912164A (en) * 1993-03-03 1999-06-15 Laboratorios Menarini S.A. Stereoselective hydrolysis of chiral carboxylic acid esters using esterase from ophiostoma or ceratocystis
GB9304351D0 (en) * 1993-03-03 1993-04-21 Chiros Ltd Arylalkanoic acid resolution and microorganisms for use therein
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US5457051A (en) * 1993-03-09 1995-10-10 Sepracor, Inc. Enantioselective hydrolysis of ketoprofen esters by beauveria bassiana and enzymes derived therefrom
AU7324696A (en) * 1995-11-17 1997-06-11 Aeci Limited Synthesis of propionic acid derivatives
US6201151B1 (en) * 1998-12-17 2001-03-13 National Science Council Of Republic Of China Processes for preparing optically active (S)-α-aryl propionic acid or ester therof
WO2003097851A1 (fr) * 2002-05-15 2003-11-27 Ono Pharmaceutical Co., Ltd. Procede de production de derive d'acide alkylcarboxylique optiquement actif
EP1951395B1 (de) * 2005-09-14 2012-02-29 Ares Trading S.A. Verfahren zur quantitativen bestimmung von poloxameren
WO2009087650A2 (en) * 2007-10-15 2009-07-16 V.B. Medicare Pvt. Ltd. A novel process for synthesis of pregabalin from substituted cyclopropane intermediate and a process for enzymatic resolution of racemic pregabalin
CN101416961B (zh) * 2008-11-21 2012-02-15 合肥金科生物医药科技有限公司 一种苯丙酸类药物光学异构体及其制药用途
WO2010089343A1 (en) * 2009-02-06 2010-08-12 Dsm Ip Assets B.V. Method for the synthesis of chiral alpha-aryl propionic acid derivatives
CN101892283A (zh) * 2010-06-03 2010-11-24 华东理工大学 红球菌Rhodococcus ruber 4.1187催化制备光学纯(S)-(+)-2-苯基丙酸
HU231033B1 (hu) 2016-03-22 2019-12-30 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Eljárás 3-as kötést tartalmazó optikailag aktív karbonsavak, karbonsav sók és karbonsav származékok előállítására
CN109706133B (zh) * 2017-10-25 2022-12-27 上海交通大学 一组新型酯酶及其应用

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Also Published As

Publication number Publication date
DE3780184D1 (de) 1992-08-13
DK172862B1 (da) 1999-08-23
CN87100031A (zh) 1987-09-09
KR960016868B1 (ko) 1996-12-23
ES2051727T3 (es) 1994-07-01
JPH08242853A (ja) 1996-09-24
NO914029L (no) 1987-07-08
EP0426656A2 (de) 1991-05-08
NO914029D0 (no) 1991-10-14
IE61983B1 (en) 1994-12-14
FI870035A (fi) 1987-07-08
DK4987A (da) 1987-07-08
JP2702915B2 (ja) 1998-01-26
DE3752257T2 (de) 1999-08-05
EP0426656B1 (de) 1999-03-03
NO169498B (no) 1992-03-23
FI870035A0 (fi) 1987-01-05
IE870024L (en) 1987-07-07
EP0233656A1 (de) 1987-08-26
NO174350B (no) 1994-01-10
PT84060A (en) 1987-02-01
KR870007276A (ko) 1987-08-18
AU6707286A (en) 1987-07-09
NO169498C (no) 1992-07-01
EP0426656A3 (de) 1991-06-26
NO174350C (no) 1994-04-20
DE3780184T2 (de) 1992-12-24
DK4987D0 (da) 1987-01-06
IL81127A0 (en) 1987-03-31
PT84060B (pt) 1989-02-28
ATE177150T1 (de) 1999-03-15
ES2131503T3 (es) 1999-08-01
IL81127A (en) 1991-07-18
EP0233656B1 (de) 1992-07-08
US5037751A (en) 1991-08-06
FI90565C (fi) 1994-02-25
ATE78054T1 (de) 1992-07-15
AU591541B2 (en) 1989-12-07
JPS6345234A (ja) 1988-02-26
CA1341324C (en) 2001-12-04
NO870040L (no) 1987-07-08
GR3005735T3 (de) 1993-06-07
NO870040D0 (no) 1987-01-06
ZA8786B (en) 1987-12-30
US4886750A (en) 1989-12-12
GR3030040T3 (en) 1999-07-30
NZ218808A (en) 1990-03-27
CA1340382C (en) 1999-02-09
JP2729044B2 (ja) 1998-03-18
FI90565B (fi) 1993-11-15
GB8600245D0 (en) 1986-02-12

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