JP3209568B2 - 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤 - Google Patents

新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤

Info

Publication number
JP3209568B2
JP3209568B2 JP11673092A JP11673092A JP3209568B2 JP 3209568 B2 JP3209568 B2 JP 3209568B2 JP 11673092 A JP11673092 A JP 11673092A JP 11673092 A JP11673092 A JP 11673092A JP 3209568 B2 JP3209568 B2 JP 3209568B2
Authority
JP
Japan
Prior art keywords
group
carbon atoms
general formula
lower alkyl
acid derivative
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
JP11673092A
Other languages
English (en)
Japanese (ja)
Other versions
JPH05125052A (ja
Inventor
靖志 河野
勝也 粟野
孝義 石崎
英介 児島
真司 工藤
康彦 迫江
康治 斉藤
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.)
Kyorin Pharmaceutical Co Ltd
Original Assignee
Kyorin Pharmaceutical Co 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 to JP11673092A priority Critical patent/JP3209568B2/ja
Application filed by Kyorin Pharmaceutical Co Ltd filed Critical Kyorin Pharmaceutical Co Ltd
Priority to CA002085347A priority patent/CA2085347C/en
Priority to KR1019920703236A priority patent/KR960007085B1/ko
Priority to EP92908279A priority patent/EP0538477B1/en
Priority to PCT/JP1992/000476 priority patent/WO1992018482A1/ja
Priority to CS923651A priority patent/CZ282165B6/cs
Priority to AT92908279T priority patent/ATE226196T1/de
Priority to DE69232812T priority patent/DE69232812T2/de
Priority to DK92908279T priority patent/DK0538477T3/da
Priority to HU9203870A priority patent/HU222522B1/hu
Priority to HU9203870A priority patent/HU9203870D0/hu
Priority to SK3651-92A priority patent/SK282146B6/sk
Priority to US07/956,012 priority patent/US5359076A/en
Priority to RO92-01558A priority patent/RO114615B1/ro
Priority to ES92908279T priority patent/ES2184730T3/es
Priority to AU15549/92A priority patent/AU647612B2/en
Priority to TW081103268A priority patent/TW203606B/zh
Priority to BG97173A priority patent/BG61262B1/bg
Priority to NO924854A priority patent/NO179174C/no
Priority to FI925697A priority patent/FI101300B/fi
Publication of JPH05125052A publication Critical patent/JPH05125052A/ja
Application granted granted Critical
Publication of JP3209568B2 publication Critical patent/JP3209568B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • 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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • C07D215/36—Sulfur 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
    • C07D215/40—Nitrogen atoms attached in position 8
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Immunology (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)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • External Artificial Organs (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
JP11673092A 1991-04-16 1992-04-10 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤 Expired - Fee Related JP3209568B2 (ja)

Priority Applications (20)

Application Number Priority Date Filing Date Title
JP11673092A JP3209568B2 (ja) 1991-04-16 1992-04-10 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤
SK3651-92A SK282146B6 (sk) 1991-04-16 1992-04-15 Cyklické deriváty aminofenyloctovej kyseliny, spôsob a medziprodukty na ich výrobu a farmaceutické prostriedky na ich báze
EP92908279A EP0538477B1 (en) 1991-04-16 1992-04-15 Novel cyclic aminophenylacetic acid derivative, production thereof, and immune response modulator containing the same as active ingredient
PCT/JP1992/000476 WO1992018482A1 (fr) 1991-04-16 1992-04-15 Nouveau derive d'acide aminophenylacetique, production de ce derive et modulateur de reponse immune contenant ce derive comme principe actif
CS923651A CZ282165B6 (cs) 1991-04-16 1992-04-15 Cyklické deriváty aminofenyloctové kyseliny, způsob jejich výroby a léčiva na jejich bázi
AT92908279T ATE226196T1 (de) 1991-04-16 1992-04-15 Neue cyclische aminophenylessigsäurederivate, ihre herstellung und immunomodulatoren , welche diese als aktiven bestandteil enthalten
KR1019920703236A KR960007085B1 (ko) 1991-04-16 1992-04-15 신규한 환상 아미노페닐아세트산 유도체, 이의 제조법 및 이들을 유효성분으로 하는 면역응답의 수식제
DK92908279T DK0538477T3 (da) 1991-04-16 1992-04-15 Hidtil ukendte cykliske aminophenyleddikesyrederivater, fremstilling deraf og immunreaktonskodulator, der indeholder disse som aktiv bestanddel
HU9203870A HU222522B1 (hu) 1991-04-16 1992-04-15 Tetrahidrokinolinil-ecetsav-származékok, hatóanyagként ilyen vegyületeket tartalmazó gyógyszerkészítmények, valamint eljárás a hatóanyagok és a gyógyszerkészítmények előállítására
HU9203870A HU9203870D0 (en) 1991-04-16 1992-04-15 Cyclic amino-phenyl-acetic acid derivatives, pharmaceutical products containing said compounds and method for producing them
CA002085347A CA2085347C (en) 1991-04-16 1992-04-15 Novel cyclic aminophenylacetic acid derivative, production therof, and immune response modulator containing the same as active ingredient
DE69232812T DE69232812T2 (de) 1991-04-16 1992-04-15 Neue cyclische aminophenylessigsäurederivate, ihre herstellung und immunomodulatoren , welche diese als aktiven bestandteil enthalten
US07/956,012 US5359076A (en) 1991-04-16 1992-04-15 Cyclic aminophenylacetic acid derivatives, process for preparing the same and immune response modulator having the same as an effective ingredient
ES92908279T ES2184730T3 (es) 1991-04-16 1992-04-15 Nuevo derivado del acido aminofenilacetico, produccion del mismo, y modulador de respuesta inmune que contiene este derivado como ingrediente activo.
AU15549/92A AU647612B2 (en) 1991-04-16 1992-04-15 Novel cyclic aminophenylacetic acid derivative, production thereof, and immune response modulator containing the same as active ingredient
RO92-01558A RO114615B1 (ro) 1991-04-16 1992-04-15 Derivaţi ciclici ai acidului aminofenilacetic cu acţiune imunomodulatoare, procedee de preparare şi intermediari în sinteza acestora
TW081103268A TW203606B (forum.php) 1991-04-16 1992-04-25
BG97173A BG61262B1 (en) 1991-04-16 1992-12-15 Cyclic derivatives of the aminophenylacetic acid, method fortheir preparation and application
NO924854A NO179174C (no) 1991-04-16 1992-12-15 Immunresponsmodulator-aktive aminofenyl-eddiksyre-derivater
FI925697A FI101300B (fi) 1991-04-16 1992-12-15 Menetelmä farmakologisesti aktiivisten 1,2,3,4-tetrahydrokinoliini-6-e tikkahappojohdannaisten valmistamiseksi ja välituotteena käytettävät k inoliinijohdannaiset

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP11100091 1991-04-16
JP3-111000 1991-04-16
JP11673092A JP3209568B2 (ja) 1991-04-16 1992-04-10 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤

Publications (2)

Publication Number Publication Date
JPH05125052A JPH05125052A (ja) 1993-05-21
JP3209568B2 true JP3209568B2 (ja) 2001-09-17

Family

ID=26450490

Family Applications (1)

Application Number Title Priority Date Filing Date
JP11673092A Expired - Fee Related JP3209568B2 (ja) 1991-04-16 1992-04-10 新規環状アミノフェニル酢酸誘導体、その製造法及びそれらを有効成分とする免疫応答の修飾剤

Country Status (19)

Country Link
US (1) US5359076A (forum.php)
EP (1) EP0538477B1 (forum.php)
JP (1) JP3209568B2 (forum.php)
KR (1) KR960007085B1 (forum.php)
AT (1) ATE226196T1 (forum.php)
AU (1) AU647612B2 (forum.php)
BG (1) BG61262B1 (forum.php)
CA (1) CA2085347C (forum.php)
CZ (1) CZ282165B6 (forum.php)
DE (1) DE69232812T2 (forum.php)
DK (1) DK0538477T3 (forum.php)
ES (1) ES2184730T3 (forum.php)
FI (1) FI101300B (forum.php)
HU (2) HU9203870D0 (forum.php)
NO (1) NO179174C (forum.php)
RO (1) RO114615B1 (forum.php)
SK (1) SK282146B6 (forum.php)
TW (1) TW203606B (forum.php)
WO (1) WO1992018482A1 (forum.php)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL112567A (en) * 1994-02-10 2000-02-29 Wyeth John & Brother Ltd Substituted quinolines their preparation and pharmaceutical compositions containing them
WO1999067238A2 (en) 1998-06-25 1999-12-29 Sepracor, Inc. Tetrahydroquinoline-indole derivatives antimicrobial agents, their uses and compositions containing them
CN102958919A (zh) * 2010-07-02 2013-03-06 霍夫曼-拉罗奇有限公司 新的四氢喹啉衍生物
US8592594B2 (en) 2010-07-02 2013-11-26 Hoffmann-La Roche Inc. Tetrahydro-quinoline derivatives
ES2805031T3 (es) 2016-02-10 2021-02-10 Sumitomo Chemical Co Método de producción de 1-metilpirrolidin-3-ol
CN116648245A (zh) 2020-12-25 2023-08-25 东丽株式会社 四氢喹啉衍生物及其医药用途
CN119403554A (zh) 2022-06-24 2025-02-07 东丽株式会社 肌萎缩性侧索硬化症的治疗剂或预防剂

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3778511A (en) 1969-04-21 1973-12-11 Ciba Geigy Corp Alpha-(1,2,3,4-tetrahydro-6-quinoyl)-carboxylic acids and derivatives thereof for treating inflammation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH576445A5 (forum.php) * 1972-03-10 1976-06-15 Ciba Geigy Ag
JPS5665097A (en) * 1979-05-30 1981-06-02 Lion Corp Manufacture of fatty acid lower alcohol ester
JPS58116466A (ja) * 1981-12-29 1983-07-11 Nippon Zoki Pharmaceut Co Ltd 新規キノリル酢酸誘導体及び該化合物を含有する医薬組成物
US4956372A (en) * 1987-10-02 1990-09-11 Kyorin Pharmaceutical Co., Ltd. Cyclic anthranilic acid derivatives and process for their preparation
US5124325A (en) * 1989-06-13 1992-06-23 Kyorin Pharmaceutical Co., Ltd. Therapeutic agents of metabolic bone disease

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3778511A (en) 1969-04-21 1973-12-11 Ciba Geigy Corp Alpha-(1,2,3,4-tetrahydro-6-quinoyl)-carboxylic acids and derivatives thereof for treating inflammation

Also Published As

Publication number Publication date
TW203606B (forum.php) 1993-04-11
JPH05125052A (ja) 1993-05-21
RO114615B1 (ro) 1999-06-30
KR930700449A (ko) 1993-03-15
HUT68184A (en) 1995-05-29
FI101300B1 (fi) 1998-05-29
AU1554992A (en) 1992-11-17
CZ282165B6 (cs) 1997-05-14
HU9203870D0 (en) 1993-03-29
FI925697A0 (fi) 1992-12-15
CZ365192A3 (en) 1993-08-11
AU647612B2 (en) 1994-03-24
ES2184730T3 (es) 2003-04-16
EP0538477A1 (en) 1993-04-28
HU222522B1 (hu) 2003-08-28
SK365192A3 (en) 2000-11-07
DE69232812D1 (de) 2002-11-21
FI101300B (fi) 1998-05-29
BG97173A (bg) 1993-12-24
DK0538477T3 (da) 2002-11-11
SK282146B6 (sk) 2001-11-06
WO1992018482A1 (fr) 1992-10-29
EP0538477A4 (en) 1993-02-12
NO179174B (no) 1996-05-13
NO179174C (no) 1996-08-21
DE69232812T2 (de) 2003-08-07
CA2085347C (en) 2003-08-19
FI925697A7 (fi) 1992-12-15
US5359076A (en) 1994-10-25
BG61262B1 (en) 1997-04-30
ATE226196T1 (de) 2002-11-15
KR960007085B1 (ko) 1996-05-27
NO924854L (no) 1993-02-16
EP0538477B1 (en) 2002-10-16
NO924854D0 (no) 1992-12-15
CA2085347A1 (en) 1992-10-17

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