ES2036145B1 - Procedimiento de preparacion de derivados de aril (o heteroaril)-pipe-razinil-butil-azoles. - Google Patents

Procedimiento de preparacion de derivados de aril (o heteroaril)-pipe-razinil-butil-azoles.

Info

Publication number
ES2036145B1
ES2036145B1 ES09200630A ES9200630A ES2036145B1 ES 2036145 B1 ES2036145 B1 ES 2036145B1 ES 09200630 A ES09200630 A ES 09200630A ES 9200630 A ES9200630 A ES 9200630A ES 2036145 B1 ES2036145 B1 ES 2036145B1
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ES
Spain
Prior art keywords
radical
denotes
optionally substituted
atom
denoted
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
ES09200630A
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English (en)
Other versions
ES2036145A1 (es
Inventor
Vidal Ramon Merce
Constansa Jordi Frigola
Corominas Juan Pares
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.)
Esteve Pharmaceuticals SA
Original Assignee
Laboratorios del Dr Esteve SA
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
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Application filed by Laboratorios del Dr Esteve SA filed Critical Laboratorios del Dr Esteve SA
Publication of ES2036145A1 publication Critical patent/ES2036145A1/es
Application granted granted Critical
Publication of ES2036145B1 publication Critical patent/ES2036145B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurosurgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

PROCEDIMIENTO DE PREPARACION DE DERIVADOS DE ARIL (O HETEROARIL)-PIPERAZINIL-BUTIL-AZOLES. EL PROCEDIMIENTO DE PREPARACION DE UN DERIVADO DE FORMULA GENERAL I, EN LA CUAL: AR REPRESENTA UN RADICAL AROMATICO, ESCOGIDO ENTRE LOS ARILOS DIFERENTEMENTE SUBSTITUIDOS, LA 2-PIRIMIDINA DIFERENTEMENTE SUBSTITUIDA, EL 2-N-METIL-IMIDAZOL Y EL 3-(1,2-BENZISOTIAZOL), Z1, Z2, Z4 REPRESENTAN SENDOS ATOMOS DE NITROGENO O DE CARBONO, Y R1, R2, R3 Y R4 REPRESENTAN UN ATOMO DE HIDROGENO, UN HALOGENO, UN RADICAL ALQUILO INFER IOR, UN RADICAL NITRO, UN RADICAL HIDROXI, UN RADICAL ALCOXI, UN RADICAL CIANO, UN RADICAL CARBOXILICO, UN RADICAL CARBOXAMIDO UN RADICAL CARBOXILATO DE ETILO, UN RADICAL ARILO, UN RADICAL SULFONICO, UN RADICAL SULFONAMIDO, UN RADICAL AMINO O AMINO SUBSTITUIDO, CONSISTE EN HACER REACCIONAR UN COMPUESTO DE FORMULA GENERAL IX, CON UN COMPUESTO DE FORMULA GENERAL III,EN LAS CUALES AR Y Z1, Z2, Z4 Y R3 TIENEN LOS SIGNIFICADOS ANTERIORES, Y X REPRESENTA UN ATOMO DE HALOGENO.
ES09200630A 1991-03-07 1992-03-05 Procedimiento de preparacion de derivados de aril (o heteroaril)-pipe-razinil-butil-azoles. Expired - Fee Related ES2036145B1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9102735A FR2673628B1 (fr) 1991-03-07 1991-03-07 Procede de preparation de derives d'aryl (ou heteroaryl)-piperazinyl-butyl-azoles.

Publications (2)

Publication Number Publication Date
ES2036145A1 ES2036145A1 (es) 1993-05-01
ES2036145B1 true ES2036145B1 (es) 1994-10-16

Family

ID=9410449

Family Applications (1)

Application Number Title Priority Date Filing Date
ES09200630A Expired - Fee Related ES2036145B1 (es) 1991-03-07 1992-03-05 Procedimiento de preparacion de derivados de aril (o heteroaril)-pipe-razinil-butil-azoles.

Country Status (17)

Country Link
US (1) US5227486A (es)
EP (1) EP0502786B1 (es)
JP (1) JP3084537B2 (es)
KR (1) KR0124133B1 (es)
AT (1) ATE137233T1 (es)
AU (1) AU651177B2 (es)
CA (1) CA2062468A1 (es)
DE (1) DE69210076T2 (es)
DK (1) DK0502786T3 (es)
ES (1) ES2036145B1 (es)
FR (1) FR2673628B1 (es)
GR (1) GR3020341T3 (es)
HU (1) HU219405B (es)
NO (1) NO180376C (es)
RU (1) RU2053230C1 (es)
YU (1) YU48213B (es)
ZA (1) ZA921682B (es)

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FR2665161B1 (fr) * 1990-07-26 1992-11-27 Esteve Labor Dr Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments.
US5712392A (en) * 1990-12-28 1998-01-27 Neurogen Corporation Certain 4-piperidine- and piperazinoalkyl-2-phenyl imidazole derivatives; dopamine receptor subtype specific ligands
US5681956A (en) * 1990-12-28 1997-10-28 Neurogen Corporation 4-aryl substituted piperazinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype specific ligands
FR2701260B1 (fr) * 1993-02-05 1995-05-05 Esteve Labor Dr Dérivés de 2-[4-(4-azolylbutyl)-1-pipérazinyl]-5-hydroxypyrimidine, leur préparation et leur application en tant que médicaments.
FR2705098B1 (fr) * 1993-05-10 1995-08-04 Esteve Labor Dr Procédé de préparation de 2-{4-[4-(chloro-1-pyrazolyl)butyl]1-pipérazinyl}pyrimidine (Lesopitron) .
JPH09505029A (ja) * 1993-07-19 1997-05-20 藤沢薬品工業株式会社 ドパミン受容体作動薬、５−ＨＴ受容体拮抗薬あるいはα▲下１▼受容体拮抗薬として有用なベンズイミダゾール誘導体
US5521313A (en) * 1994-05-05 1996-05-28 Bristol-Myers Squibb Company Process for preparing certain azapirones
US6355659B1 (en) 1994-07-29 2002-03-12 Laboratorios Del Dr. Esteve, S.A. 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same
FR2723091B1 (fr) * 1994-07-29 1996-11-08 Esteve Labor Dr Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles
GB9500580D0 (en) * 1995-01-12 1995-03-01 Merck Sharp & Dohme Therapeutic agents
ES2099031B1 (es) * 1995-05-31 1997-12-01 Esteve Labor Dr Nuevos polimorfos de diclorhidrato de lesopitron y sus formas hidratadas, procedimientos de preparacion y composiciones que los contienen.
US6011052A (en) * 1996-04-30 2000-01-04 Warner-Lambert Company Pyrazolone derivatives as MCP-1 antagonists
FR2763950B1 (fr) 1997-06-02 2002-09-20 Esteve Labor Dr 2- {4- [4-(4,5-dichloro-2-methylimidazol-1-yl)butyl] -1- piperazinyl }-5-fluoropyrimidine, sa preparation et son utilisation therapeutique
US6166205A (en) * 1998-09-02 2000-12-26 Neurogen Corporation 2-Aryl-4-(1-[4-heteroaryl]piperazin-1-yl)methylimidazoles: dopamine . D.sub4 receptor subtype ligands
US6046331A (en) * 1998-12-17 2000-04-04 Synaptic Pharmaceutical Corporation Imidazolones and their use in treating benign prostatic hyperplasia and other disorders
US7332494B2 (en) 2000-08-14 2008-02-19 Janssen Pharmaceutica, N.V. Method for treating allergies using substituted pyrazoles
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DE60126286T2 (de) 2000-08-14 2007-11-15 Ortho-Mcneil Pharmaceutical, Inc. Substituierte pyrazole
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DK1531822T3 (da) 2002-06-12 2009-12-07 Chemocentryx Inc 1-aryl-4-substituerede piperazin derivater til anvendelse som CCR1 antagonister til behandlingen af inflammation og immunforstyrrelser
US7842693B2 (en) * 2002-06-12 2010-11-30 Chemocentryx, Inc. Substituted piperazines
US20050256130A1 (en) * 2002-06-12 2005-11-17 Chemocentryx, Inc. Substituted piperazines
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CA2428237C (en) * 2003-05-08 2010-07-20 Delmar Chemicals Inc. Process for the preparation of carbostyril derivatives
US7435831B2 (en) * 2004-03-03 2008-10-14 Chemocentryx, Inc. Bicyclic and bridged nitrogen heterocycles
CN1950082B (zh) * 2004-03-03 2013-02-06 凯莫森特里克斯股份有限公司 双环和桥连的含氮杂环化物
CN101213194A (zh) 2004-08-03 2008-07-02 惠氏公司 可用于治疗心血管疾病的吲唑化合物
JP2006169154A (ja) * 2004-12-15 2006-06-29 Sumitomo Chemical Co Ltd 第四級アンモニウム塩の製造方法
US9802929B2 (en) * 2012-11-26 2017-10-31 Shenyang Haiwang Biotechnology Co., Ltd. Benzo five-membered nitrogen heterocyclic piperidine or piperazine derivatives and preparation methods and pharmaceutical compositions thereof
CN105669665A (zh) * 2016-03-15 2016-06-15 烟台贝森医药科技有限公司 哌罗匹隆的制备方法

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CA1279645C (en) * 1986-02-27 1991-01-29 Ineke Van Wijngaarden Aryl-substituted (n-piperidinyl)methyl- and (n-piperazinyl)methylazoles having antipsychotic properties
FR2642759B1 (fr) * 1989-02-09 1991-05-17 Laboratorios Esteve Sa Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante
FR2672052B1 (fr) * 1991-01-28 1995-05-24 Esteve Labor Dr Derives d'aryl (ou heteroaryl)-piperazinyl-alkyl-azoles, leur preparation et leur application en tant que medicaments.
US5077293A (en) * 1990-06-29 1991-12-31 Bristol-Myers Squibb Co. 1-indolyalkyl-4-(alkoxypyrimidinyl)piperazines

Also Published As

Publication number Publication date
NO180376C (no) 1997-04-09
DE69210076T2 (de) 1996-10-24
YU48213B (sh) 1997-08-22
YU21592A (sh) 1994-06-24
DE69210076D1 (de) 1996-05-30
JP3084537B2 (ja) 2000-09-04
NO920888D0 (no) 1992-03-06
AU1142992A (en) 1992-09-10
JPH0578313A (ja) 1993-03-30
KR0124133B1 (ko) 1997-11-24
RU2053230C1 (ru) 1996-01-27
EP0502786A1 (fr) 1992-09-09
HU219405B (hu) 2001-04-28
EP0502786B1 (fr) 1996-04-24
CA2062468A1 (en) 1992-09-08
ES2036145A1 (es) 1993-05-01
HU9200768D0 (en) 1992-05-28
DK0502786T3 (da) 1996-05-13
GR3020341T3 (en) 1996-09-30
HUT60731A (en) 1992-10-28
US5227486A (en) 1993-07-13
FR2673628B1 (fr) 1993-07-09
FR2673628A1 (fr) 1992-09-11
NO920888L (no) 1992-09-08
KR920018046A (ko) 1992-10-21
NO180376B (no) 1996-12-30
ATE137233T1 (de) 1996-05-15
AU651177B2 (en) 1994-07-14
ZA921682B (en) 1992-11-25

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Effective date: 20040601