CA2054850A1 - Derives immino-cycliques, compositions pharmaceutiques qui contiennent de ces composes et procedes d'obtention - Google Patents

Derives immino-cycliques, compositions pharmaceutiques qui contiennent de ces composes et procedes d'obtention

Info

Publication number
CA2054850A1
CA2054850A1 CA2054850A CA2054850A CA2054850A1 CA 2054850 A1 CA2054850 A1 CA 2054850A1 CA 2054850 A CA2054850 A CA 2054850A CA 2054850 A CA2054850 A CA 2054850A CA 2054850 A1 CA2054850 A1 CA 2054850A1
Authority
CA
Canada
Prior art keywords
preparing
compounds
processes
pharmaceutical compositions
compositions containing
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.)
Granted
Application number
CA2054850A
Other languages
English (en)
Other versions
CA2054850C (fr
Inventor
Frank Himmelsbach
Volkhard Austel
Helmut Pieper
Wolfgang Eisert
Thomas Muller
Johannes Weisenberger
Gunter Linz
Gerd Kruger
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2054850A1 publication Critical patent/CA2054850A1/fr
Application granted granted Critical
Publication of CA2054850C publication Critical patent/CA2054850C/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
CA002054850A 1990-11-02 1991-11-01 Derives immino-cycliques, compositions pharmaceutiques qui contiennent de ces composes et procedes d'obtention Expired - Lifetime CA2054850C (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4035961A DE4035961A1 (de) 1990-11-02 1990-11-02 Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DEP4035961.1 1990-11-02

Publications (2)

Publication Number Publication Date
CA2054850A1 true CA2054850A1 (fr) 1992-05-03
CA2054850C CA2054850C (fr) 2001-01-02

Family

ID=6418111

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002054850A Expired - Lifetime CA2054850C (fr) 1990-11-02 1991-11-01 Derives immino-cycliques, compositions pharmaceutiques qui contiennent de ces composes et procedes d'obtention

Country Status (25)

Country Link
US (2) US5541343A (fr)
EP (1) EP0483667B1 (fr)
JP (1) JP2937589B2 (fr)
KR (1) KR100223135B1 (fr)
AT (1) ATE163008T1 (fr)
BG (1) BG62025B2 (fr)
BR (1) BR1100445A (fr)
CA (1) CA2054850C (fr)
DE (2) DE4035961A1 (fr)
DK (1) DK0483667T3 (fr)
EE (1) EE03099B1 (fr)
ES (1) ES2113867T3 (fr)
FI (1) FI107606B (fr)
GR (1) GR3026508T3 (fr)
HK (1) HK1008742A1 (fr)
HU (2) HUT67288A (fr)
IE (1) IE913822A1 (fr)
IL (1) IL99926A (fr)
MX (1) MX9203677A (fr)
NO (1) NO174806B (fr)
NZ (1) NZ240463A (fr)
PT (1) PT99402B (fr)
RU (1) RU2040519C1 (fr)
SG (1) SG81852A1 (fr)
ZA (1) ZA918734B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998006694A1 (fr) * 1996-08-16 1998-02-19 Du Pont Pharmaceuticals Company Amidinophenyl-pyrrolidines, -pyrrolines et -isoxazolidines et leurs derives
US5942544A (en) * 1996-02-22 1999-08-24 Dupont Pharmaceuticals Company α-branched anilines, toluenes, and analogs thereof as factor Xa inhibitors
US6057342A (en) * 1996-08-16 2000-05-02 Dupont Pharmaceutical Co. Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof
US6169107B1 (en) 1993-04-28 2001-01-02 Sumitomo Pharmaceutical Co., Ltd. Indoloylguanidine derivatives

Families Citing this family (85)

* Cited by examiner, † Cited by third party
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DE4127404A1 (de) * 1991-08-19 1993-02-25 Thomae Gmbh Dr K Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
AU646966B2 (en) * 1991-08-23 1994-03-10 Takeda Chemical Industries Ltd. 2-piperazinone compounds, their production and use
DE4213919A1 (de) * 1992-04-28 1993-11-04 Thomae Gmbh Dr K Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DK0567967T3 (da) * 1992-04-28 1996-11-18 Thomae Gmbh Dr K Tritium-mærkede fibrinogen-receptor-antagonister, deres anvendelse og fremgangsmåde til deres fremstilling
DE4213931A1 (de) * 1992-04-28 1993-11-04 Thomae Gmbh Dr K Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE4219158A1 (de) * 1992-06-11 1993-12-16 Thomae Gmbh Dr K Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE4241632A1 (de) * 1992-12-10 1994-06-16 Thomae Gmbh Dr K Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US5314902A (en) * 1993-01-27 1994-05-24 Monsanto Company Urea derivatives useful as platelet aggregation inhibitors
WO1994022820A1 (fr) * 1993-03-31 1994-10-13 G.D. Searle & Co. Amidinophenyl-1-pyrrolidones piperidinones azetinones inhibitrices de l'agregation plaquettaire
DE4424975A1 (de) * 1994-07-15 1996-01-18 Thomae Gmbh Dr K 2-Piperidinone, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0799202A1 (fr) * 1994-12-23 1997-10-08 Dr. Karl Thomae GmbH Derives de piperazine, medicaments contenant ces composes, leur utilisation et leur procede de preparation
CA2216162A1 (fr) * 1995-04-26 1996-10-31 Takeda Chemical Industries, Ltd. Piperazinones utiles comme inhibiteurs d'agregation plaquettaire
DE19515500A1 (de) * 1995-04-27 1996-10-31 Thomae Gmbh Dr K Substituierte Phenylamidine, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US5719296A (en) * 1995-10-30 1998-02-17 Merck & Co., Inc. Pseudopeptide lactam inhibitors of peptide binding to MHC class II proteins
DE19604191A1 (de) * 1996-02-06 1997-08-07 Hoechst Schering Agrevo Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19621483A1 (de) * 1996-05-29 1997-12-04 Hoechst Ag Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19621482A1 (de) 1996-05-29 1997-12-04 Hoechst Ag Substituierte 1-Naphthoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
AU8875798A (en) * 1997-08-29 1999-03-22 Proteus Molecular Design Ltd Meta-benzamidine derivatives as serin protease inhibitors
US6740682B2 (en) 1997-08-29 2004-05-25 Tularik Limited Meta-benzamidine derivatives as serine protease inhibitors
US5962504A (en) * 1997-09-08 1999-10-05 Georgetown University Substituted 2-pyrrolidinone activators of PKC
KR20010032175A (ko) 1997-11-20 2001-04-16 야스이 쇼사꾸 비페닐아미딘 유도체
WO1999050249A2 (fr) 1998-04-01 1999-10-07 Du Pont Pharmaceuticals Company Antagonistes de l'integrine
WO1999052861A1 (fr) * 1998-04-09 1999-10-21 Institut für Diagnostikforschung GmbH an der Freien Universität Berlin NOUVEAUX DERIVES DE BENZYLGUANIDINE POUR LA THERAPIE ET LE DIAGNOSTIC IN VIVO ET $i(IN VITRO)
US6562828B1 (en) 1998-04-10 2003-05-13 Japan Tobacco Inc. Amidine compounds
SK15092000A3 (sk) * 1998-04-23 2001-05-10 Abbott Laboratories Pyrolidíny ako inhibítory neuraminidáz
US6518305B1 (en) 1998-04-23 2003-02-11 Abbott Laboratories Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases
US6455571B1 (en) 1998-04-23 2002-09-24 Abbott Laboratories Inhibitors of neuraminidases
WO2000005234A1 (fr) * 1998-07-22 2000-02-03 Suntory Limited INHIBITEURS DE NF-λB CONTENANT DES DERIVES D'INDANE EN TANT QU'INGREDIENT ACTIF
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US6362201B1 (en) 1999-03-02 2002-03-26 Merck & Co., Inc. 3-cyclopropyl and 3-cyclobutyl pyrrolidine modulators of chemokine receptor activity
CA2360740A1 (fr) 1999-03-02 2000-09-08 Boehringer Ingelheim Pharmaceuticals, Inc. Composes utiles en tant qu'inhibiteurs reversibles de la cathepsine s
US6489354B1 (en) 1999-03-02 2002-12-03 Merck & Co., Inc. 3-alkyl substituted pyrrolidine modulators of chemokine receptor activity
US6372764B1 (en) 1999-03-02 2002-04-16 Merck & Co., Inc. Pyrrolidine modulators of chemokine receptor activity
US6420364B1 (en) 1999-09-13 2002-07-16 Boehringer Ingelheim Pharmaceuticals, Inc. Compound useful as reversible inhibitors of cysteine proteases
FR2817257B1 (fr) * 2000-11-30 2009-03-20 Sanofi Synthelabo Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant
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JP4399253B2 (ja) * 2001-06-20 2010-01-13 ワイス プラスミノゲンアクチベーターインヒビター−１（ｐａｉ−１）のインヒビターとしての、置換されたインドール酸誘導体
TWI224101B (en) * 2001-06-20 2004-11-21 Wyeth Corp Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1)
JP2006514640A (ja) * 2002-12-10 2006-05-11 ワイス プラスミノゲンアクティベータインヒビターのインヒビターとしての置換３−アルキル及び３−アリールアルキル１ｈ−イル酢酸誘導体
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UA80453C2 (en) * 2002-12-10 2007-09-25 Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1)
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US7141592B2 (en) * 2003-09-25 2006-11-28 Wyeth Substituted oxadiazolidinediones
US7446201B2 (en) * 2003-09-25 2008-11-04 Wyeth Substituted heteroaryl benzofuran acids
US7582773B2 (en) * 2003-09-25 2009-09-01 Wyeth Substituted phenyl indoles
US7265148B2 (en) * 2003-09-25 2007-09-04 Wyeth Substituted pyrrole-indoles
US7442805B2 (en) * 2003-09-25 2008-10-28 Wyeth Substituted sulfonamide-indoles
US7420083B2 (en) * 2003-09-25 2008-09-02 Wyeth Substituted aryloximes
US7268159B2 (en) * 2003-09-25 2007-09-11 Wyeth Substituted indoles
US7351726B2 (en) * 2003-09-25 2008-04-01 Wyeth Substituted oxadiazolidinediones
US7534894B2 (en) 2003-09-25 2009-05-19 Wyeth Biphenyloxy-acids
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RU2014151622A (ru) 2007-10-05 2015-08-20 Акусела Инк. Композиции и способы лечения нейродегенеративных заболеваний
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CA2981041C (fr) 2015-03-27 2023-09-05 California Institute Of Technology Alkylation decarboxylative catalytique asymetrique d'alkyle au moyen de faibles concentrations de catalyseur et d'un precatalyseur robuste
EP3426391A4 (fr) 2016-03-11 2019-08-28 California Institute of Technology Compositions et procédés d'acylation de lactames
EP3480190B1 (fr) 2017-11-01 2023-01-04 California Institute of Technology Procédés d'alkylation allylique énantiosélective d'esters, lactones et lactames avec des alcools allyliques inactivés
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US6248772B1 (en) 1993-04-28 2001-06-19 Sumitomo Pharmaceuticals Co., Ltd. Indoloylguanidine derivatives
US5942544A (en) * 1996-02-22 1999-08-24 Dupont Pharmaceuticals Company α-branched anilines, toluenes, and analogs thereof as factor Xa inhibitors
WO1998006694A1 (fr) * 1996-08-16 1998-02-19 Du Pont Pharmaceuticals Company Amidinophenyl-pyrrolidines, -pyrrolines et -isoxazolidines et leurs derives
US6057342A (en) * 1996-08-16 2000-05-02 Dupont Pharmaceutical Co. Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof

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FI915136A0 (fi) 1991-10-31
JPH04264068A (ja) 1992-09-18
RU2040519C1 (ru) 1995-07-25
NO174806B (no) 1994-04-05
EP0483667A2 (fr) 1992-05-06
US5541343A (en) 1996-07-30
PT99402A (pt) 1992-09-30
DE4035961A1 (de) 1992-05-07
DK0483667T3 (da) 1998-09-23
HK1008742A1 (en) 1999-05-14
SG81852A1 (en) 2001-07-24
NO914294D0 (no) 1991-11-01
JP2937589B2 (ja) 1999-08-23
AU8692691A (en) 1992-05-07
EP0483667A3 (en) 1992-09-16
KR920009793A (ko) 1992-06-25
EE03099B1 (et) 1998-06-15
DE59108930D1 (de) 1998-03-12
HU913455D0 (en) 1992-01-28
KR100223135B1 (ko) 1999-10-15
FI915136A (fi) 1992-05-03
FI107606B (fi) 2001-09-14
IL99926A0 (en) 1992-08-18
NZ240463A (en) 1997-04-24
GR3026508T3 (en) 1998-07-31
IE913822A1 (en) 1992-05-22
MX9203677A (es) 1992-07-01
AU650488B2 (en) 1994-06-23
PT99402B (pt) 1999-04-30
BG62025B2 (bg) 1998-12-30
IL99926A (en) 1996-06-18
US5591769A (en) 1997-01-07
HU211563A9 (en) 1995-12-28
EP0483667B1 (fr) 1998-02-04
CA2054850C (fr) 2001-01-02
NO174806C (fr) 1994-07-13
HUT67288A (en) 1995-03-28
ZA918734B (en) 1993-05-04
NO914294L (no) 1992-05-04
ES2113867T3 (es) 1998-05-16
BR1100445A (pt) 2000-07-18
ATE163008T1 (de) 1998-02-15

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