HK25892A - Aromatic compounds - Google Patents

Aromatic compounds

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Publication number
HK25892A
HK25892A HK258/92A HK25892A HK25892A HK 25892 A HK25892 A HK 25892A HK 258/92 A HK258/92 A HK 258/92A HK 25892 A HK25892 A HK 25892A HK 25892 A HK25892 A HK 25892A
Authority
HK
Hong Kong
Prior art keywords
formula
compound
enyl
pyrrolidino
prop
Prior art date
Application number
HK258/92A
Other languages
German (de)
English (en)
Inventor
Geoffrey George Coker
John William Addison Findlay
Original Assignee
The Wellcome Foundation Limited
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 The Wellcome Foundation Limited filed Critical The Wellcome Foundation Limited
Publication of HK25892A publication Critical patent/HK25892A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Emergency Medicine (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Superconductors And Manufacturing Methods Therefor (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (17)

1. Procédé de préparation d'un composé de formule (I): ou d'un sel, ester ou amide de celui-ci, où
R1 est un radical hydrocarboné aliphatique bivalent en C1-7 ou une liaison simple;
R2 et R3 sont identiques ou différents et sont chacun un atome d'hydrogène ou radical C1-4alcoyle ou bien, pris ensemble avec l'atome d'azote, forment un radical hétérocyclique azoté comptant quatre à six chaînons;
R4 est un atome d'hydrogène ou d'halogène ou radical hydroxyle, cyano, C1-4acyloxy, C1-4alcoxy ou C1-4alcoyle éventuellement substitué par 1 à 3 atomes d'halogène;
X est -N= ou -CH=; et
A et B représentent chacun un atome d'hydrogène ou bien -CA-CB représente -C=C-; qui comprend
a) la réaction d'un composé de formule (VI) ou d'un ester de celui-ci avec une amine HNR2R3 où X, A, B et R1 à R4 sont tels que définis dans la revendication 1 et L est un radical partant;
b) lorsqu'il est requis de préparer un composé de formule (I) où R1 est (CH2)o et A et B sont des atomes d'hydrogène, la réaction d'un composé de formule (VII) où X, R2, R3 et R4 sont tels que définis dans la revendication 1 et R5 est un atome d'halogène, avec un C1-6alcoyllithium, suivie d'un traitement au moyen de dioxyde de carbone;
c) lorsqu'il est requis de préparer un composé de formule (I) où R1 est (CH2)aCH=CH(CH2)b et a est 0, la réaction d'un composé de formule (VIII): où X, R2, R3, R4, A et B sont tels que définis dans la revendication 1, avec un réactif de Wittig propre à fixer la chaîne latérale CH=CH(CH2)bCOR6, où COR6 est un radical acide, ester ou amide tel que défini ci-dessus, suivie de la déprotection du radical carboxyle si la chose est souhaitée;
d) lorsqu'il est requis de préparer un composé de formule (I) où CA-CB représente une double liaison:
i) la réaction d'un ester, amide ou sel d'acide carboxylique d'un composé de formule (IX): avec un réactif de Wittig propre à fixer la chaîne latérale =CHCH2NR2R3 où X et R1 à R4 sont tels que définis dans la revendication 1, suivie de la déprotection du radical carboxyle si la chose est souhaitée;
ii) l'élimination de R7OH d'un composé de formule (X): ou d'un ester ou amide de celui-ci, où X et R1 à R4 sont tels que définis dans la revendication 1 et R7 est un atome d'hydrogène ou radical C1-4acyle;
iii) la réaction d'un composé de formule (XI): avec une amine HNR2R3 où X et R1 à R4 sont tels que définis dans la revendication 1 et R8 est un radical C1-4acyloxy;
e) et ensuite, la conversion facultative d'un composé de formule (I) en un autre composé de formule (I) par isomérisation d'une double liaison, réduction d'une ou plusieurs doubles liaisons ou déestérification du radical ester.
2. Procédé suivant la revendication 1 de préparation d'un composé de formule (II) ou un sel, ester ou amide de celui-ci, où R1 à R4, X, A et B sont tels que définis à propos de la revendication 1.
3. Procédé suivant la revendication 1 ou 2 de préparation d'un composé où R1 est un radical (CH2)n où n est un entier de 0 à 7 ou un radical (CH2)aCH=CH(CH2)b où a et b sont indépendamment 0 à 5 et la somme de a et b n'excède pas 5.
4. Procédé suivant l'une quelconque des revendications 1 à 3 de préparation d'un composé de formule (Illa) ou (Illb) ou d'un sel, ester ou amide de celui-ci, où R1 est (CH2)n, où n est un entier de 1 à 7 ou bien (CH2)aCH:CH(CH2)b' où a et b sont indépendamment 0 à 5 et la somme de a et b n'excède pas 5; R2 et R3 sont identiques ou différents et sont des atomes d'hydrogène ou radicaux alcoyle inférieurs (de 1 à 4 atomes de carbone) ou bien, pris ensemble avec l'atome d'azote, forment un radical hétérocyclique azoté (de 4 à 6 chaînons); et R4A est un atome d'hydrogène ou d'halogène ou radical alcoyle inférieur (de 1 à 4 atomes de carbone) ou alcoxy inférieur (de 1 à 4 atomes de carbone)..
5. Procédé suivant l'une quelconque des revendications 1 à 4 de préparation d'un composé où R2 et R3 pris ensemble avec l'atome d'azote forment un radical pyrrolidino, pipéridino ou morpholino.
6. Procédé suivant l'une quelconque des revendications 1 à 5 de préparation d'un composé où R1 est (CH2)2 ou CH=CH, NR2R3 est un radical pyrrolidino ou diméthylamino et R4 est un radical méthyle, trifluorométhyle, méthoxy, bromo ou chloro.
7. Procédé suivant l'une quelconque des revendications 1 à 6 de préparation d'un composé de formule (IV): ou d'un sel, ester ou amide de celui-ci; où R1 à R4 sont tels que définis dans la revendication 1.
8. Procédé suivant la revendication 7, dans lequel R1 dans la formule (IV) est une liaison simple ou le radical CH=CH ou CH2CH2; NR2R3 est un radical pyrrolidino et R4 est un radical méthyle ou trifluorométhyle.
9. Procédé suivant l'une quelconque des revendications 1 à 8, dans lequel CA-CB représente une double liaison, et le radical CH2NR2R3 est en trans par rapport au cycle contenant X.
10. Procédé suivant l'une quelconque des revendications 1 à 6 de préparation d'un composé de formule (V): ou d'un sel, ester ou amide de celui-ci; où R1 à R4 sont tels que définis dans la revendication 1.
11. Procédé suivant la revendication 10, où R1 dans la formule (V) est une liaison simple ou un radical CH=CH ou CH2CH2, NR2R3 est un radical diméthylamino et R4 est un radical chloro ou bromo.
12. Procédé suivant la revendication 1 de préparation d'un composé choisi parmi:
l'acide (E)-3-(6-(3-pyrrolidino-1-(4-tolyl)prop-1E-ényl)-2-pyridyl)acrylique
l'acide 3-(6-(3-pyrrolidino-1-(4-tolyl)prop-1E-ényl)-2-pyridyl)propionique
l'acide (E)-3-(6-(3-diméthylamino-1-(4-tolyl)prop-1E-ényl)-2-pyridyl)acrylique
l'acide (E)-3-(6-(3-pyrrolidino-1-(4-trifluorométhylphényl)prop-1E-ényl)-2-pyridyl)acrylique
l'acide (E)-3-(6-(3-pyrrolidino-1-(4-méthoxyphényl)prop-1E-ényl)-2-pyridyl)acrylique
l'acide (E)-3-(6-(1-phényl-3-pyrrolidinoprop-1-E-ényl)-2-pyridyl)acrylique
l'acide (E)-3-(6-(1-(4-chlorophényl)-3-pyrrolidinoprop-1E-ényl)-2-pyridyl)acrylique
l'acide 6-(3-pyrrolidino-1-(4-tolyl)prop-1E-ényl)pyridine-2-carboxylique
l'acide (E)-3-(3-pyrrolidino-1-(4-tolyl)prop-1-ényl)benzoïque
l'acide (E)-3-(3-pyrrolidino-1-(4-tolyl)prop-1-ényl)cinnamique
l'acide (E)-3-((E)-3-pyrrolidino-1-(4-méthoxyphényl)prop-1-ényl))cinnamique
l'acide (E)-3-((E)-3-diméthylamino-1-(4-tolyl)prop-1-ényl))cinnamique
l'acide (E)-3-(3-(3-pyrrolidino-1-(4-tolyl)prop-1-ényl)phényl)propionique
ou d'un sel, ester ou amide de celui-ci.
13. Composition pharmaceutique, qui comprend un composé de formule (I) conjointement avec un ou plusieurs excipients pharmaceutiquement acceptables et, facultativement, d'autres constituants thérapeutiques quelconques.
14. Procédé de préparation d'une composition pharmaceutique telle que définie dans la revendication 13, qui comprend le stade de mettre le composé actif en association avec un excipient qui comprend un ou plusieurs constituants accessoires.
15. Procédé de préparation d'un composé de formule X où R1, R2, R3, R4 et X sont tels que définis dans la revendication 1 et R7 est un atome d'hydrogène ou radical C1-4acyle, le procédé comprenant soit
(i) au cas où R7 est un atome d'hydrogène, la réaction d'un composé de formule XX où R2, R3, R4 et X sont tels que définis à propos de la formule X, avec un composé CH=CHCOR13 où COR13 est un radical ester ou amide soit
(ii) la réaction d'un composé de formule XXII où R2, R3, R4, R7 et X sont tels que définis à propos de la formule X, avec l'acide malonique.
16. Procédé de préparation d'un composé de fomrule XI où
R1 est un radical hydrocarboné aliphatique bivalent en C1-7 ou une liaison simple;
R4 est un atome d'hydrogène ou d'halogène ou radical hydroxyle, cyano, C1-4acyloxy, C1-4alcoxy ou C1-4alcoyle éventuellement substitué par 1 à 3 atomes d'halogène;
X est-N= ou ―CH=; et
R8 est un radical C1-4acyloxy lequel procédé comprend l'acylation du composé correspondant où R8 est un radical hydroxyle au moyen d'un agent de C1-4acylation.
17. Procédé suivant la revendication 1, stade opératoire (e), où le composé de formule I est un composé de formule XII où R1, R2, R3, R4 et X sont tels que définis pour la formule I.
HK258/92A 1982-02-04 1992-04-09 Aromatic compounds HK25892A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8203261 1982-02-04
GB8229705 1982-10-18

Publications (1)

Publication Number Publication Date
HK25892A true HK25892A (en) 1992-04-16

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ES (6) ES8403872A1 (fr)
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GB (1) GB2114565B (fr)
GR (1) GR77407B (fr)
HK (1) HK25892A (fr)
HU (1) HU189223B (fr)
IE (1) IE54600B1 (fr)
IL (3) IL67829A (fr)
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ATE64596T1 (de) 1991-07-15
AU555083B2 (en) 1986-09-11
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ES523414A0 (es) 1984-10-01
KR870001916B1 (ko) 1987-10-22
JPH0251897B2 (fr) 1990-11-08
DK43683D0 (da) 1983-02-03
ES523418A0 (es) 1984-10-01
KR870001927B1 (ko) 1987-10-22
EP0085959A2 (fr) 1983-08-17
SI8310221A8 (en) 1995-10-31
PL141639B1 (en) 1987-08-31
DD209446A5 (de) 1984-05-09
PL245842A1 (en) 1985-01-30
EP0085959B1 (fr) 1989-04-19
PL245845A1 (en) 1985-01-30
KR880001466B1 (ko) 1988-08-11
PL245841A1 (en) 1985-01-30
NO830368L (no) 1983-08-05
KR870001918B1 (ko) 1987-10-22
FI830380L (fi) 1983-08-05
BG42005A3 (en) 1987-09-15
PL140812B1 (en) 1987-05-30
NO162556B (no) 1989-10-09
UY23404A1 (es) 1992-10-19
GB2114565A (en) 1983-08-24
KR870001917B1 (ko) 1987-10-22
HU189223B (en) 1986-06-30
ES519491A0 (es) 1984-04-01
CA1275102C (fr) 1990-10-09
IE54600B1 (en) 1989-12-06
ES523415A0 (es) 1984-10-01
DE3382321D1 (de) 1991-07-25
KR870001915B1 (ko) 1987-10-22
ES8500233A1 (es) 1984-10-01
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DK164662C (da) 1992-12-14
GR77407B (fr) 1984-09-13
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JPH01301661A (ja) 1989-12-05
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FI82450C (fi) 1991-03-11
EP0249950B1 (fr) 1991-06-19
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ES523417A0 (es) 1984-10-01
MC1498A1 (fr) 1983-11-17
NL930057I2 (nl) 1994-02-16
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SG106091G (en) 1992-03-20
IL67829A (en) 1988-06-30
NL930057I1 (nl) 1993-09-01
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CY1627A (en) 1992-07-10
ES8500234A1 (es) 1984-10-01
BG41822A3 (en) 1987-08-14
PT76192A (en) 1983-03-01
IL67829A0 (en) 1983-06-15
FI82450B (fi) 1990-11-30
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PT76192B (en) 1986-01-24

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