PH22944A - Cyclic amine derivatives - Google Patents

Cyclic amine derivatives

Info

Publication number
PH22944A
PH22944A PH34532A PH34532A PH22944A PH 22944 A PH22944 A PH 22944A PH 34532 A PH34532 A PH 34532A PH 34532 A PH34532 A PH 34532A PH 22944 A PH22944 A PH 22944A
Authority
PH
Philippines
Prior art keywords
group
carbon atoms
general formula
hereinbefore
alkyl
Prior art date
Application number
PH34532A
Inventor
Psiorz Dr Manfred
Bomhard Dr Andreas
Reiffen Dr Manfred
Hauel Dr Norbert
Narr Dr Berthold
Heider Dr Joachim
Noll Dr Klaus
Dammgen Dr Juergen
Lillie Dr Christian
Kobinger Prof Dr Walter
Original Assignee
Thomae Gmbh Dr K
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 Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K
Publication of PH22944A publication Critical patent/PH22944A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (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 Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1. Claims for the contracting states : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE New cyclic amine derivatives of general formula see diagramm : EP0224794,P49,F1 wherein A represents a -CH2 -CH2 -, -CH=CH-, see diagramm : EP0224794,P49,F2 or see diagramm : EP0224794,P49,F3 group and B represents a methylene, carbonyl or thiocarbonyl group or A represents a -CO-CO- or see diagramm : EP0224794,P49,F4 group and B represents a methylene group, whilst the atom marked x is linked to the phenyl nucleus, E represents a straight-chained alkylene group with 1 to 3 carbon atoms optionally substituted by an alkyl group with 1 to 3 carbon atoms, G represents a straight-chained alkylene group with 1 to 5 carbon atoms optionally substituted by an alkyl group with 1 to 3 carbon atoms, whilst a methylene group, adjacent to a phenyl nucleus, of a straight-chained alkylene group with 3 to 5 carbon atoms optionally substituted by an alkyl group may be replaced by an oxygen or sulphur atom or by an imino, methylimino, sulphinyl or sulphonyl group, R1 represents a hydrogen or halogen atom, a trifluoromethyl, nitro, amino, alkylamino, dialkylamino, alkyl, hydroxy, alkoxy or phenylalkoxy group, whilst each alkyl moiety may contain from 1 to 3 carbon atoms, R2 represents a hydrogen or halogen atom, a hydroxy, alkoxy, phenylalkoxy or alkyl group, whilst each alkyl moiety may contain from 1 to 3 carbon atoms, or R1 and R2 together represent an alkylenedioxy group with 1 or 2 carbon atoms, R3 represents a hydrogen or halogen atom, an alkyl or alkoxy group with 1 to 3 carbon atoms in the alkyl moiety, or a hydroxy, nitro, cyano or trifluoromethyl group, R4 represents a hydrogen atom, an alkoxy, alkanesulphonyloxy, amino, alkylamino or dialkylamino group with 1 to 3 carbon atoms in each alkyl moiety or an alkanoylamino group with 2 or 3 carbon atoms in the alkanoyl moiety or R3 and R4 together represent an alkylenedioxy group with 1 or 2 carbon atoms, R5 represents a hydrogen or halogen atom, a hydroxy, alkyl or alkoxy group with 1 to 3 carbon atoms in the alkyl moiety, m represents the number 1, 2, 3, 4 or 5 and n represents the number 0, 1 or 2, but n + m must represent the number 3, 4 or 5, the enantiomers, diastereomers and acid addition salts thereof. 1. Claims for the contracting states : AT, ES, GR Process for preparing new cyclic amine derivatives of general formula see diagramm : EP0224794,P54,F1 wherein A represents a -CH2 -CH2 -, -CH=CH-, see diagramm : EP0224794,P54,F2 or see diagramm : EP0224794,P54,F3 group and B represents a methylene, carbonyl or thiocarbonyl group or A represents a -CO-CO- or see diagramm : EP0224794,P54,F4 group and B represents a methylene group, whilst the atom marked x is linked to the phenyl nucleus, a methylene group, whilst the atom marked x is linked to the phenyl nucleus, E represents a straight-chained alkylene group with 1 to 3 carbon atoms optionally substituted by an alkyl group with 1 to 3 carbon atoms, G represents a straight-chained alkylene group with 1 to 5 carbon atoms optionally substituted by an alkyl group with 1 to 3 carbon atoms, whilst a methylene group, adjacent to a phenyl nucleus, of a straight-chained alkylene group with 3 to 5 carbon atoms optionally substituted by an alkyl group may be replaced by an oxygen or sulphur atom or by an imino, methylimino, sulphinyl or sulphonyl group, R1 represents a hydrogen or halogen atom, a trifluoromethyl, nitro, amino, alkylamino, dialkylamino, alkyl, hydroxy, alkoxy or phenylalkoxy group, whilst each alkyl moiety may contain from 1 to 3 carbon atoms, R2 represents a hydrogen or halogen atom, a hydroxy, alkoxy, phenylalkoxy or alkyl group, whilst each alkyl moiety may contain from 1 to 3 carbon atoms, or R1 and R2 together represent an alkylenedioxy group with 1 or 2 carbon atoms, R3 represents a hydrogen or halogen atom, an alkyl or alkoxy group with 1 to 3 carbon atoms in the alkyl moiety, or a hydroxy, nitro, cyano or trifluoromethyl group, R4 represents a hydrogen atom, an alkoxy, alkanesulphonyloxy, amino, alkylamino or dialkylamino group with 1 to 3 carbon atoms in each alkyl moiety or an alkanoylamino group with 2 or 3 carbon atoms in the alkanoyl moiety or R3 and R4 together represent an alkylenedioxy group with 1 or 2 carbon atoms, R5 represents a hydrogen or halogen atom, a hydroxy, alkyl or alkoxy group with 1 to 3 carbon atoms in the alkyl moiety, m represents the number 1, 2, 3, 4 or 5 and n represents the number 0, 1 or 2, but n + m must represent the number 3, 4 or 5, the enantiomers, diastereomers and acid addition salts thereof, characterised in that a) a compound of general formula see diagramm : EP0224794,P55,F1 wherein A, B, E, m and n are defined as hereinbefore, R'1 represents a hydroxy, amino or alkylamino group protected by a protecting group or has the meanings given for R1 hereinbefore and R'2 represents a hydroxy group protected by a protecting group or has the meanings given for R2 hereinbefore, is reacted with a compound of general formula see diagramm : EP0224794,P55,F2 wherein R'3 , R'4 and R'5 have the meanings given for R3 , R4 and R5 hereinbefore but the hydroxy, amino or alkylamino groups contained in the groups R3 to R5 may be protected by a protecting group, and U represents a nucleophilic leaving group such as a halogen atom or a sulphonyloxy group, and optionally any protecting group used is subsequently split off, or b) in order to prepare compounds of general formula I wherein G has the meanings given for Gin claims 1 to 5, with the exception of the groups containing a sulphenyl, sulphinyl or sulphonyl group, A represents a -CH2 -CH2 - group, B represents a methylene or carbonyl group and m + n represent the number 4, a compound of general formula see diagramm : EP0224794,P55,F3 wherein R1 to R5 and E are defined as hereinbefore, G' has the meanings given for Gas hereinbefore with the exception of the radicals containing a sulphur atom or a sulphinyl or sulphonyl group, A' represents a -CH=CH- or -CH2 CH2 - group and B' represents a methylene or carbonyl group, is hydrogenated in a solvent or mixture of solvents, or c) in order to prepare compounds of general formula I wherein B represents a carbonyl or methylene group, a compound of general formula see diagramm : EP0224794,P56,F1 wherein A is defined as hereinbefore, R'1 represents a hydroxy, amino or alkylamino group protected by a protecting group or has the meanings given for R1 hereinbefore, R'2 represents a hydroxy group protected by a protecting group or has the meanings given for R2 hereinbefore, and B' represents a carbonyl or methylene group, is reacted with a compound of general formula see diagramm : EP0224794,P56,F2 wherein E, G, m and n are defined as hereinbefore, R'3 , R'4 and R'5 have the meanings given for R3 , R4 and R5 hereinbefore, but the hydroxy, amino or alkylamino groups contained in the groups R3 to R5 may be protected by a protecting group, and V represents a nucleophilically exchangeable group such as a halogen atom or a sulphonyloxy group, and optionally any protecting group used is subsequently split off, or d) in order to prepare compounds of general formula I wherein A represents a -CH2 -CH2 - or -CH=CH- group and B represents a thiocarbonyl group, a compound of general formula see diagramm : EP0224794,P57,F1 wherein R1 to R5 , E, G, m and n are defined as hereinbefore and A' represents a -CH2 -CH2 - or -CH=CH- group, is reacted with a sulphurising agent, or e) in order to prepare compounds of general formula I wherein A represents a see diagramm : EP0224794,P57,F2 group and B represents a methylene group, a compound of general formula see diagramm : EP0224794,P57,F3 wherein R1 to R5 , E, G, m and n are defined as hereinbefore is reduced in a suitable solvent, or f) in order to prepare compounds of general formula I wherein A represents a -CH2 -CH2 - or -CH=CH- group and B represents a methylene group, a compound of general formula see diagramm : EP0224794,P57,F4 wherein R1 to R5 , E, G, m and n are defined as hereinbefore and A, represents a -CH2 -CH2 - or -CH=CH- group, is reduced in a suitable solvent, or g) in order to prepare compounds of general formula I wherein A represents a -COCO- group, a compound of general formula see diagramm : EP0224794,P58,F1 wherein R1 to R5 , E, G, m and n are defined as hereinbefore is oxidised in a suitable solvent or mixture of solvents, or h) in order to prepare compounds of general formula I wherein G has the meanings given for G hereinbefore with the exception of the radicals containing a sulphur atom or a sulphinyl or sulphonyl group, A represents a -CH2 -CH2 - group and B represents a methylene or carbonyl group, a compound of general formula see diagramm : EP0224794,P58,F2 wherein R1 to R5 , E, m and n are defined as hereinbefore, G' has the meanings given for G hereinbefore, with the exception of the radicals containing a sulphur atom or a sulphinyl or sulphonyl group and B' represents a methylene or carbonyl group, is hydrogenated in a solvent or mixture of solvents and subsequently, if desired, a compound of general formula I thus obtained wherein R1 and/or R3 represents a nitro group is converted by reduction into a corresponding amino compound of general formula I, or a compound of general formula I thus obtained wherein R4 represents a hydroxy or amino group is converted by acylation into a corresponding alkanesulphonyloxy or alkanoylamino compound of general formula I, or a compound of general formula I thus obtained which contains at least one chiral centre is resolved into its diastereomers or into its enantiomers and/or a compound of general formula I thus obtained is converted into the acid addition salts thereof, particularly its physiologically acceptable acid addition salts with inorganic or organic acids.
PH34532A 1985-11-27 1986-11-27 Cyclic amine derivatives PH22944A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19853541811 DE3541811A1 (en) 1985-11-27 1985-11-27 NEW CYCLIC AMINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF

Publications (1)

Publication Number Publication Date
PH22944A true PH22944A (en) 1989-02-03

Family

ID=6286902

Family Applications (1)

Application Number Title Priority Date Filing Date
PH34532A PH22944A (en) 1985-11-27 1986-11-27 Cyclic amine derivatives

Country Status (25)

Country Link
EP (1) EP0224794B1 (en)
JP (1) JPH0625128B2 (en)
KR (1) KR950007589B1 (en)
AT (1) ATE56447T1 (en)
AU (1) AU589712B2 (en)
CA (1) CA1321194C (en)
CZ (1) CZ410391A3 (en)
DD (1) DD256132A5 (en)
DE (2) DE3541811A1 (en)
DK (1) DK174564B1 (en)
ES (1) ES2018152B3 (en)
FI (1) FI88299C (en)
GR (1) GR3001107T3 (en)
HK (1) HK123993A (en)
HU (1) HU196787B (en)
IE (1) IE59487B1 (en)
IL (1) IL80758A (en)
MX (1) MX9202813A (en)
NO (1) NO168034C (en)
NZ (1) NZ218412A (en)
PH (1) PH22944A (en)
PT (1) PT83815B (en)
SU (1) SU1442073A3 (en)
UA (1) UA8034A1 (en)
ZA (1) ZA868933B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3717561A1 (en) * 1987-05-25 1988-12-08 Thomae Gmbh Dr K INDOL, ISOCHINOLINE AND BENZAZEPINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
CA1298427C (en) * 1987-03-13 1992-03-31 Johannes Adrianus Maria Van Broekhoven Process for removing palladium catalyst remnants from copolymers of carbon monoxide with one or more olefinically unsaturated compounds
FI95572C (en) * 1987-06-22 1996-02-26 Eisai Co Ltd Process for the preparation of a medicament useful as a piperidine derivative or its pharmaceutical salt
FR2634207B1 (en) * 1988-07-12 1990-09-07 Synthelabo ((PIPERIDINYL-4) METHYL) BENZAZEPINES DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
DE10018401A1 (en) * 2000-04-13 2001-10-25 Boehringer Ingelheim Pharma Medicament for treating hypertrophy-related myocardial disease, containing bradycardic agent, preferably cilobradine, and optionally another cardiac drug
DK1362590T3 (en) * 2002-07-25 2004-03-29 Boehringer Ingelheim Pharma Use of cilobradine or its pharmaceutically acceptable salts for the treatment or prevention of heart failure
US20040138306A1 (en) 2002-07-25 2004-07-15 Boehringer Ingelheim Pharma Gmbh & Co. Kg Use of a specific cyclic amine derivative or the pharmaceutically acceptable salts thereof for the treatment or prevention of heart failure
EP1762179A1 (en) 2005-09-07 2007-03-14 Boehringer Ingelheim Vetmedica Gmbh Method for improving diagnostic quality in echocardiography
EP2741736B1 (en) 2011-08-12 2017-11-22 Boehringer Ingelheim Vetmedica GmbH Taste masked pharmaceutical composition
EP2953612A1 (en) 2013-02-11 2015-12-16 Boehringer Ingelheim Vetmedica GmbH Kit-of-parts

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2639718C2 (en) * 1976-09-03 1987-03-05 Dr. Karl Thomae Gmbh, 7950 Biberach 1-[6,7-Dimethoxy-3,4-dihydro-2H-isoquinolin-1-on-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane, its physiologically acceptable acid addition salts and medicaments containing these compounds
CH645632A5 (en) * 1977-01-01 1984-10-15 Thomae Gmbh Dr K Arylalkylamines
DE3119874A1 (en) * 1981-05-19 1982-12-09 Dr. Karl Thomae Gmbh, 7950 Biberach "BENZAZEPINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS MEDICINAL PRODUCTS"
DE3418271A1 (en) * 1984-05-17 1985-11-21 Dr. Karl Thomae Gmbh, 7950 Biberach NEW BENZAZEPINE DERIVATIVES, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF

Also Published As

Publication number Publication date
DE3541811A1 (en) 1987-06-04
KR950007589B1 (en) 1995-07-12
FI88299C (en) 1993-04-26
FI864785A (en) 1987-05-28
HUT43056A (en) 1987-09-28
HK123993A (en) 1993-11-19
IE59487B1 (en) 1994-03-09
IL80758A (en) 1991-01-31
JPH0625128B2 (en) 1994-04-06
ATE56447T1 (en) 1990-09-15
DK174564B1 (en) 2003-06-10
MX9202813A (en) 1992-06-30
CZ410391A3 (en) 1993-03-17
PT83815B (en) 1989-06-30
AU589712B2 (en) 1989-10-19
AU6576486A (en) 1987-06-04
DK568386A (en) 1987-05-28
DK568386D0 (en) 1986-11-26
DD256132A5 (en) 1988-04-27
GR3001107T3 (en) 1992-05-12
JPS62138491A (en) 1987-06-22
CA1321194C (en) 1993-08-10
EP0224794A3 (en) 1988-10-19
NO864744D0 (en) 1986-11-26
IL80758A0 (en) 1987-02-27
DE3674159D1 (en) 1990-10-18
ZA868933B (en) 1988-07-27
FI88299B (en) 1993-01-15
EP0224794B1 (en) 1990-09-12
SU1442073A3 (en) 1988-11-30
ES2018152B3 (en) 1991-04-01
HU196787B (en) 1989-01-30
PT83815A (en) 1986-12-01
IE863110L (en) 1987-05-27
NO168034C (en) 1992-01-08
NO168034B (en) 1991-09-30
KR870004973A (en) 1987-06-02
NZ218412A (en) 1989-05-29
FI864785A0 (en) 1986-11-25
EP0224794A2 (en) 1987-06-10
UA8034A1 (en) 1995-12-26

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