ES2052028T3 - Un metodo para preparar compuestos diarilicos anti-ateroscleroticos. - Google Patents

Un metodo para preparar compuestos diarilicos anti-ateroscleroticos.

Info

Publication number
ES2052028T3
ES2052028T3 ES89312025T ES89312025T ES2052028T3 ES 2052028 T3 ES2052028 T3 ES 2052028T3 ES 89312025 T ES89312025 T ES 89312025T ES 89312025 T ES89312025 T ES 89312025T ES 2052028 T3 ES2052028 T3 ES 2052028T3
Authority
ES
Spain
Prior art keywords
diarilic
aterosclerotic
compounds
preparing anti
compound
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 - Lifetime
Application number
ES89312025T
Other languages
English (en)
Inventor
William Paul Jackson
Clifford John Harris
Richard James Arrowsmith
John Gordon Dann
Kevin Julian O'connor
Robert Frederick Geoffre Booth
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Application granted granted Critical
Publication of ES2052028T3 publication Critical patent/ES2052028T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C327/44—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Steroid Compounds (AREA)
  • Prostheses (AREA)
  • Polarising Elements (AREA)
  • Eye Examination Apparatus (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

LA PRESENTE INVENCION CONCIERNE A COMPUESTOS DE FORMULA (I) DONDE M ES 0 O 1. W ES HIDROGENO, UN GRUPO ALQUILO CICLIDO, RAMIFICADAS O RECTAS C2 - 16, O UN GRUPO ALQUINIL, O PN(CH2)N DONDE F ES FENIL Y N ES UN ENTERO DE 0 A 2, EL GRUPO FENIL ES OPCIONALMENTE SUSTITUIDO POR UNO O MAS ATOMOS DE CARBONO O GRUPOS INDEPENDIENTEMENTE SELECCIONADOS DE HALOGENO, HIDROXI, NITRO, ALCOXI C1 - 4, Y ALQUIL C1 - 4, DONDE UNO O MAS ATOMOS DE HIDROGENO EN DICHO GRUPO ALQUILICO OPCIONALMENTE REEMPLAZADOS POR HALOGENOS, R1NHCO DONDE R1 ES HIDROGENO O UN GRUPO ALQUILICO C1 - 6 O R2CONH DONDE R2 ES HIDROGENO O UN GRUPO ALQUILICO C1 - 6; X ES -(CH2)P NHCO N H, DONDE P ES UN ENTERO DE 0 A 2. LAS FORMULA 1, 2, 3, 4, Y 5 DONDE A ES UN HALOGENO; Y ES -(CH2)Q DONDE Q ES UN ENTERO DE 1 A 3 O -CH=CH-(E O Z); Z ES UN GRUPO ALQUILICO C1 - 6 OP. SUS. POR UNO O MAS GRUPOS POLARES SELECCIONADOS; Y UN ANILLO A ES OP. SUS., POR 1 O MAS ATOMOS O GRUPOS SELECCIONADOS DE HALOGENO, HIDROXI, NITRO, ALCOXI, C1 - 4 Y ALQUIL C1 - 4 DONDE UNO O MAS ATOMOS DE HIDROGENO EN DICHO GRUPO ALQUILICO ES OPCIONALMENTE REEMPLAZADO POR HALOGENO. DICHO COMPUESTO DE FORMULA (I) NO ES N - [(4 METILFENIL METIL] FENIL) ACETAMINA O (ALFA) (P-TOLIL) - OCRESOL CARBANILATO; Y SALES SOLVENTES Y DERIVADOS FUNCIONALES FISIOLOGICAMENTE DEL MISMO, PROCESOS PARA LA PREPARACION DEL COMPUESTO Y FORMULACIONES FARMACEUTICAS QUE CONTIENE Y SU USO EN LA MEDICINA ESTAN DISPUESTAS
ES89312025T 1988-11-21 1989-11-20 Un metodo para preparar compuestos diarilicos anti-ateroscleroticos. Expired - Lifetime ES2052028T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB888827152A GB8827152D0 (en) 1988-11-21 1988-11-21 Anti-atherosclerotic diaryl compounds

Publications (1)

Publication Number Publication Date
ES2052028T3 true ES2052028T3 (es) 1994-07-01

Family

ID=10647180

Family Applications (2)

Application Number Title Priority Date Filing Date
ES91107475T Expired - Lifetime ES2062610T3 (es) 1988-11-21 1989-11-20 Compuesto diarilico anti-ateroesclerotico.
ES89312025T Expired - Lifetime ES2052028T3 (es) 1988-11-21 1989-11-20 Un metodo para preparar compuestos diarilicos anti-ateroscleroticos.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES91107475T Expired - Lifetime ES2062610T3 (es) 1988-11-21 1989-11-20 Compuesto diarilico anti-ateroesclerotico.

Country Status (27)

Country Link
EP (2) EP0370740B1 (es)
JP (1) JPH02188568A (es)
KR (1) KR900007790A (es)
AT (2) ATE78812T1 (es)
AU (1) AU638950B2 (es)
CA (1) CA2003395A1 (es)
CZ (1) CZ277693B6 (es)
DD (1) DD289263A5 (es)
DE (2) DE68913762T2 (es)
DK (1) DK581889A (es)
ES (2) ES2062610T3 (es)
FI (1) FI895520A0 (es)
GB (1) GB8827152D0 (es)
GR (1) GR3006091T3 (es)
HU (1) HU205342B (es)
IE (2) IE940341L (es)
IL (1) IL92358A (es)
LT (1) LTIP418A (es)
MX (1) MX9203417A (es)
MY (1) MY106247A (es)
NO (1) NO172233C (es)
NZ (1) NZ231448A (es)
PL (1) PL162010B1 (es)
PT (2) PT92354A (es)
RU (1) RU2036901C1 (es)
TW (1) TW213445B (es)
ZA (1) ZA898842B (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ229828A (en) * 1988-08-09 1992-03-26 Squibb & Sons Inc Aryl cyanoguanidine derivatives and pharmaceutical compositions
US5290814A (en) * 1988-11-21 1994-03-01 Burroughs Wellcome Co. Anti-atherosclerotic diaryl compounds
GB9020841D0 (en) * 1990-09-25 1990-11-07 Wellcome Found Anti-atherosclerotic aryl compounds
GB9027023D0 (en) * 1990-12-12 1991-01-30 Wellcome Found Anti-atherosclerotic aryl compounds
IL100915A (en) * 1991-02-19 1996-03-31 Erba Carlo Spa Double-transformed urea and theories, their preparation and pharmaceutical preparations containing them
US5310748A (en) * 1992-05-11 1994-05-10 The Du Pont Merck Pharmaceutical Company Imidazoles for the treatment of atherosclerosis
US5364875A (en) * 1992-05-11 1994-11-15 The Du Pont Merck Pharmaceutical Company Imidazoles linked to bicyclic heterocyclic groups for the treatment of atherosclerosis
CA2123728A1 (en) * 1993-05-21 1994-11-22 Noriyoshi Sueda Urea derivatives and their use as acat inhibitors
JP3894949B2 (ja) * 1993-06-30 2007-03-22 ザ、ウェルカム、ファンデーション、リミテッド 抗アテローム性動脈硬化症ジアリール化合物
NZ264063A (en) * 1993-08-13 1995-11-27 Nihon Nohyaku Co Ltd N-(2-phenylpyrid-3-yl)- and n-(4-phenylpyrimidin-5-yl)-n'-phenylurea derivatives and pharmaceutical compositions
US5547966A (en) * 1993-10-07 1996-08-20 Bristol-Myers Squibb Company Aryl urea and related compounds
US5576335A (en) * 1994-02-01 1996-11-19 Nisshin Flour Milling Co., Ltd. Urea derivatives and their use as ACAT inhibitors
US5491152A (en) * 1994-03-23 1996-02-13 The Du Pont Merck Pharmaceutical Company Derivatives of cyclic ethers and sulfides for the treatment of atherosclerosis
CA2200981A1 (en) * 1994-10-04 1996-04-11 Hisashi Takasugi Urea derivatives and their use as acat-inhibitors
EP0742208A1 (en) * 1995-05-05 1996-11-13 Grelan Pharmaceutical Co., Ltd. 2-Ureido-benzamide derivatives
US5866609A (en) * 1996-08-09 1999-02-02 Ss Pharmaceutical Co., Ltd. Substituted vinylurea derivatives and medicine containing the same
FR2946340B1 (fr) 2009-06-05 2011-06-24 Galderma Res & Dev Nouveaux n-phenyl acetamie, inhibiteurs de l'enzyme soat-1, compositions pharmaceutiques et cosmetiques les contenant.
FR2946345B1 (fr) 2009-06-05 2011-05-20 Galderma Res & Dev Nouveaux derives dioxo-imidazolidine, inhibiteurs de l'enzyme soat-1, compositions pharmaceutiques et cosmetiques les contenant.
FR2946342B1 (fr) 2009-06-05 2011-06-24 Galderma Res & Dev Nouveaux derives de dioxo-imidazolidine, inhibiteurs de l'enzyme soat-1, compositions pharmaceutiques et cosmetiques les contenant.
FR2946346B1 (fr) 2009-06-05 2011-05-20 Galderma Res & Dev Nouveaux derives dioxo-imidazolidine, inhibiteurs de l'enzyme soat-1, compositions pharmaceutiques et cosmetiques les contenant.

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4029786A (en) * 1972-08-11 1977-06-14 Imperial Chemical Industries Limited Morpholine derivatives for treating depression
GB1382526A (en) * 1972-08-11 1975-02-05 Ici Ltd Morpholine derivatives
ZA801680B (en) * 1979-04-03 1981-03-25 Fujisawa Pharmaceutical Co 2-imidazoline derivatives,process for the preparation thereof and the pharmaceutical composition of the same
US4269829A (en) * 1979-06-18 1981-05-26 Rohm And Haas Company Method and composition for treating helminths containing O,O-dialkyl-N-(substituted phenyl)aminothiocarbonyl phosphoramidates
US4387106A (en) * 1982-01-26 1983-06-07 American Cyanamid Company Method of treating atherosclerosis with di(aralkyl)ureas and di(aralkyl)thioureas
JPS60500176A (ja) * 1982-12-30 1985-02-07 ビ−チヤム　グル−プ　ピ−エルシ− 四環式化合物
US4603145A (en) * 1983-05-06 1986-07-29 American Cyanamid Company Antiatherosclerotic diphenyl alkanamides
US4716175A (en) * 1987-02-24 1987-12-29 Warner-Lambert Company Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase
ES2037768T3 (es) * 1987-07-02 1993-07-01 Warner-Lambert Company Procedimiento para preparar n-(fenil(2,6-disustituido))-ureas y carbamatos inhibidores de acil-coa: colesterol acil-transferasa.

Also Published As

Publication number Publication date
TW213445B (es) 1993-09-21
DK581889A (da) 1990-05-22
NO894616D0 (no) 1989-11-20
DE68913762D1 (de) 1994-04-14
DK581889D0 (da) 1989-11-20
CZ277693B6 (en) 1993-03-17
IE893700L (en) 1990-05-21
DD289263A5 (de) 1991-04-25
AU638950B2 (en) 1993-07-15
AU4536389A (en) 1990-05-24
ATE78812T1 (de) 1992-08-15
FI895520A0 (fi) 1989-11-20
CA2003395A1 (en) 1990-05-21
IE65411B1 (en) 1995-10-18
MX9203417A (es) 1992-07-01
PT92354A (pt) 1990-05-31
PT101725A (pt) 1996-01-31
GR3006091T3 (es) 1993-06-21
IL92358A (en) 1994-06-24
ATE102604T1 (de) 1994-03-15
IE940341L (en) 1990-05-21
DE68902301T2 (de) 1993-02-25
MY106247A (en) 1995-04-29
EP0450660A1 (en) 1991-10-09
NO172233C (no) 1993-06-23
ES2062610T3 (es) 1994-12-16
PL162010B1 (pl) 1993-08-31
RU2036901C1 (ru) 1995-06-09
HUT52040A (en) 1990-06-28
NO172233B (no) 1993-03-15
IL92358A0 (en) 1990-07-26
LTIP418A (en) 1994-09-25
EP0370740B1 (en) 1992-07-29
NO894616L (no) 1990-05-22
HU205342B (en) 1992-04-28
GB8827152D0 (en) 1988-12-29
EP0370740A1 (en) 1990-05-30
EP0450660B1 (en) 1994-03-09
KR900007790A (ko) 1990-06-02
DE68902301D1 (de) 1992-09-03
ZA898842B (en) 1991-07-31
NZ231448A (en) 1992-03-26
JPH02188568A (ja) 1990-07-24
CS655889A3 (en) 1992-11-18
PT101725B (pt) 1997-08-29
DE68913762T2 (de) 1994-06-23

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