ES8706643A1 - Un procedimiento para preparar compuestos heterociclicos nitrogenados. - Google Patents

Un procedimiento para preparar compuestos heterociclicos nitrogenados.

Info

Publication number
ES8706643A1
ES8706643A1 ES555013A ES555013A ES8706643A1 ES 8706643 A1 ES8706643 A1 ES 8706643A1 ES 555013 A ES555013 A ES 555013A ES 555013 A ES555013 A ES 555013A ES 8706643 A1 ES8706643 A1 ES 8706643A1
Authority
ES
Spain
Prior art keywords
formula
activity
antihistamine
hetero
iii
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
Application number
ES555013A
Other languages
English (en)
Other versions
ES555013A0 (es
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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
Priority claimed from GB848427878A external-priority patent/GB8427878D0/en
Priority claimed from GB858517714A external-priority patent/GB8517714D0/en
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of ES8706643A1 publication Critical patent/ES8706643A1/es
Publication of ES555013A0 publication Critical patent/ES555013A0/es
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • 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
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Eye Examination Apparatus (AREA)
  • Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Cosmetics (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

METODO DE PREPARAR COMPUESTOS HETEROCICLICOS NITROGENADOS. CONSISTE EN HACER REACCIONAR UN COMPUESTO DE FORMULA (II) CON UN COMPUESTO DE FORMULA (III), PARA OBTENER COMPUESTOS HETEROCICLICOS NITROGENADOS DE FORMULA (I) Y SUS SALES FARMACEUTICAMENTE ACEPTABLES, DONDE R ELEVADO A 1 Y R ELEVADO A 2 SON INDEPENDIENTEMENTE ALQUILO DE C 1 A 4; Y ES ALQUILO DE C 1 A 4 DE CADENA LINEAL O RAMIFICADA; N ES UN ENTERO DE 2 A 5; Z ES UN GRUPO DE SUB-FORMULA (III) O (IV); Y M ES 1. LA REACCION SE LLEVA A CABO EN UN DISOLVENTE Y A TEMPERATURAS COMPRENDIDAS ENTRE 120 Y 170GC. TIENEN APLICACIONES FARMACEUTICAS POR SU ACTIVIDAD ANTI-HISTAMINICA. *FORMULA*
ES555013A 1984-11-03 1986-05-16 Un procedimiento para preparar compuestos heterociclicos nitrogenados. Expired ES8706643A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848427878A GB8427878D0 (en) 1984-11-03 1984-11-03 Compounds
GB858517714A GB8517714D0 (en) 1985-07-13 1985-07-13 Compounds

Publications (2)

Publication Number Publication Date
ES8706643A1 true ES8706643A1 (es) 1987-07-01
ES555013A0 ES555013A0 (es) 1987-07-01

Family

ID=26288415

Family Applications (2)

Application Number Title Priority Date Filing Date
ES548448A Expired ES8702385A1 (es) 1984-11-03 1985-10-31 Un procedimiento para preparar un compuesto heterociclico nitrogenado
ES555013A Expired ES8706643A1 (es) 1984-11-03 1986-05-16 Un procedimiento para preparar compuestos heterociclicos nitrogenados.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES548448A Expired ES8702385A1 (es) 1984-11-03 1985-10-31 Un procedimiento para preparar un compuesto heterociclico nitrogenado

Country Status (22)

Country Link
US (2) US4681883A (es)
EP (1) EP0181163B1 (es)
JP (1) JPH0764816B2 (es)
KR (1) KR930002490B1 (es)
CN (1) CN85108132A (es)
AT (1) ATE48839T1 (es)
AU (1) AU576269B2 (es)
CA (1) CA1260468A (es)
DE (1) DE3574872D1 (es)
DK (1) DK168763B1 (es)
ES (2) ES8702385A1 (es)
FI (1) FI854275A (es)
GR (1) GR852644B (es)
HU (1) HU194211B (es)
IE (1) IE58586B1 (es)
IL (1) IL76871A0 (es)
JO (1) JO1410B1 (es)
NO (1) NO164096C (es)
NZ (1) NZ214023A (es)
PH (1) PH22679A (es)
PT (1) PT81405B (es)
ZW (1) ZW19285A1 (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8417194D0 (en) * 1984-07-05 1984-08-08 Boots Co Plc Therapeutic agents
KR960002875B1 (ko) * 1989-04-28 1996-02-27 도오레 가부시기가이샤 옥사졸유도체 및 이것을 이용한 고감도 발광분석방법
US5451596A (en) * 1992-12-29 1995-09-19 Rhone Poulenc Rorer Pharmaceuticals Inc. Cycloalkyl amine bis-aryl squalene synthase inhibitors
US5434163A (en) * 1993-05-14 1995-07-18 The Medical College Of Pennsylvania Treatment of Cryptococcus neoformans infection
US5455260A (en) * 1993-05-21 1995-10-03 Rhone-Poulenc Rorer Pharmaceuticals Inc. Aliphatic amino bis-aryl squalene synthase inhibitors
AU1117497A (en) * 1995-11-13 1997-06-05 Albany Medical College Analgesic compounds and uses thereof
DE19645313A1 (de) 1996-11-04 1998-05-07 Basf Ag Substituierte 3-Benzylpyrazole
CL2008003120A1 (es) 2007-11-01 2009-10-09 Acucela Inc Compuestos derivados de fenilalquil-, fenilalquenil-, fenilalquinil- amina, feniltioalquilamina, fenilaminoalquilamina, fenilalcoxiamina y fenilalquilguanidina; composicion farmaceutica; y uso de los compuestos para tratar un trastorno o enfermedad oftalmologica tal como retinopatia, maculopatia, retinitis pigmentosa, uveitis, entre otras.
HUE053282T2 (hu) 2013-08-19 2021-06-28 Univ California Vegyületek és eljárások epilepsziás rendellenesség kezelésére
WO2022034121A1 (en) 2020-08-11 2022-02-17 Université De Strasbourg H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA793443B (en) * 1978-07-26 1980-12-31 Glaxo Group Ltd Heterocyclic derivatives
US4496567A (en) * 1978-11-13 1985-01-29 Smith Kline & French Laboratories Limited Phenyl alkylaminopyrimidones
US4521418A (en) * 1979-02-21 1985-06-04 Smith Kline & French Laboratories Limited Guanidinothiazolyl derivatives
ZA815961B (en) * 1980-08-27 1983-04-27 Glaxo Group Ltd Heterocyclic derivatives
US4439437A (en) * 1981-04-28 1984-03-27 Smith Kline & French Laboratories Limited 2-[2-Thiazolyl or 2-guanidino-4-thiazolyl methylthioethyl(or butyl)amino]-3-(hydroxy or carboxy)pyridines, compositions containing same and method of use
US4447611A (en) * 1982-05-27 1984-05-08 American Home Products Corporation Benzo-fused and heterocyclic fused imidazole anti-ulcer agents
US4490527A (en) * 1982-09-30 1984-12-25 American Home Products Corporation Benzo-fused heterocyclic anti-ulcer agents
GB8318638D0 (en) * 1983-07-09 1983-08-10 Smith Kline French Lab Chemical compounds
GB8332091D0 (en) * 1983-12-01 1984-01-11 Smith Kline French Lab Chemical compounds
GB8417194D0 (en) * 1984-07-05 1984-08-08 Boots Co Plc Therapeutic agents
KR930009443B1 (ko) * 1985-03-14 1993-10-04 상꾜 가부시끼가이샤 페녹시알킬아미노 피리미딘 유도체의 제조방법

Also Published As

Publication number Publication date
FI854275A0 (fi) 1985-10-31
AU4911385A (en) 1986-05-08
FI854275A (fi) 1986-05-04
PT81405A (en) 1985-11-01
KR860004053A (ko) 1986-06-16
JPS61115069A (ja) 1986-06-02
DK168763B1 (da) 1994-06-06
NZ214023A (en) 1989-08-29
DK500985A (da) 1986-05-04
EP0181163A3 (en) 1987-02-25
HU194211B (en) 1988-01-28
US4681883A (en) 1987-07-21
NO164096C (no) 1990-08-29
EP0181163B1 (en) 1989-12-20
ES8702385A1 (es) 1987-01-01
JPH0764816B2 (ja) 1995-07-12
ES555013A0 (es) 1987-07-01
IL76871A0 (en) 1986-02-28
CA1260468A (en) 1989-09-26
PH22679A (en) 1988-11-14
DK500985D0 (da) 1985-10-31
PT81405B (pt) 1988-02-17
KR930002490B1 (ko) 1993-04-02
IE852683L (en) 1986-05-03
DE3574872D1 (de) 1990-01-25
JO1410B1 (en) 1986-11-30
AU576269B2 (en) 1988-08-18
EP0181163A2 (en) 1986-05-14
NO164096B (no) 1990-05-21
ES548448A0 (es) 1987-01-01
CN85108132A (zh) 1986-07-16
GR852644B (es) 1986-03-05
IE58586B1 (en) 1993-10-06
ATE48839T1 (de) 1990-01-15
ZW19285A1 (en) 1986-05-21
NO854368L (no) 1986-05-05
HUT38926A (en) 1986-07-28
US4952589A (en) 1990-08-28

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