CA1175431A - Tri-substituted imidazole derivatives, processes for their manufacture, pharmaceutical preparations containing them, and their use - Google Patents

Tri-substituted imidazole derivatives, processes for their manufacture, pharmaceutical preparations containing them, and their use

Info

Publication number
CA1175431A
CA1175431A CA000382377A CA382377A CA1175431A CA 1175431 A CA1175431 A CA 1175431A CA 000382377 A CA000382377 A CA 000382377A CA 382377 A CA382377 A CA 382377A CA 1175431 A CA1175431 A CA 1175431A
Authority
CA
Canada
Prior art keywords
phenyl
substituted
lower alkoxy
pyridyl
carbon atoms
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
CA000382377A
Other languages
English (en)
French (fr)
Inventor
Alfred Sallmann
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.)
Novartis AG
Original Assignee
Ciba Geigy Investments Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd
Priority to CA000451683A priority Critical patent/CA1185976A/en
Application granted granted Critical
Publication of CA1175431A publication Critical patent/CA1175431A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/26—Radicals substituted by carbon atoms having three bonds to hetero 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
CA000382377A 1980-07-25 1981-07-23 Tri-substituted imidazole derivatives, processes for their manufacture, pharmaceutical preparations containing them, and their use Expired CA1175431A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA000451683A CA1185976A (en) 1980-07-25 1984-04-10 Process for the manufacture of novel tri-substituted imidazole derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH571580 1980-07-25
CH5715/80-5 1980-07-25

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA000451683A Division CA1185976A (en) 1980-07-25 1984-04-10 Process for the manufacture of novel tri-substituted imidazole derivatives

Publications (1)

Publication Number Publication Date
CA1175431A true CA1175431A (en) 1984-10-02

Family

ID=4298165

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000382377A Expired CA1175431A (en) 1980-07-25 1981-07-23 Tri-substituted imidazole derivatives, processes for their manufacture, pharmaceutical preparations containing them, and their use

Country Status (23)

Country Link
US (1) US4447431A (OSRAM)
EP (1) EP0045081B1 (OSRAM)
JP (1) JPS5756466A (OSRAM)
KR (13) KR850000883B1 (OSRAM)
AR (1) AR230269A1 (OSRAM)
AT (1) ATE17349T1 (OSRAM)
AU (2) AU7340481A (OSRAM)
CA (1) CA1175431A (OSRAM)
DD (2) DD201677A5 (OSRAM)
DE (1) DE3173434D1 (OSRAM)
DK (1) DK331881A (OSRAM)
ES (8) ES8301472A1 (OSRAM)
FI (1) FI812326A7 (OSRAM)
GB (1) GB2080805B (OSRAM)
GR (1) GR75287B (OSRAM)
IE (1) IE52071B1 (OSRAM)
IL (1) IL63410A (OSRAM)
NO (1) NO812542L (OSRAM)
NZ (1) NZ197828A (OSRAM)
PL (8) PL237004A1 (OSRAM)
PT (1) PT73424B (OSRAM)
SU (8) SU1235454A3 (OSRAM)
ZA (1) ZA815078B (OSRAM)

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GB2123831B (en) * 1981-07-20 1986-01-15 Ciba Geigy Ag Trisubstituted oxazo compounds
EP0084756A1 (de) * 1982-01-22 1983-08-03 Ciba-Geigy Ag Trisubstituierte Oxazaverbindungen
FR2633291B1 (fr) * 1988-06-27 1990-09-07 Oreal Derives d'hydroxy-4 isoxazoles, leur procede de preparation et compositions cosmetiques et pharmaceutiques les contenant
US5252322A (en) * 1989-09-22 1993-10-12 The Gillette Company Skin tanning compositions containing imidazoles
NZ239161A (en) * 1990-07-31 1994-01-26 Smithkline Beecham Corp Substituted [1h-imidazol-5-yl] alkanoic acid derivatives; medicaments,
MX9300141A (es) * 1992-01-13 1994-07-29 Smithkline Beecham Corp Compuestos de imidazol novedosos, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen.
US5916891A (en) 1992-01-13 1999-06-29 Smithkline Beecham Corporation Pyrimidinyl imidazoles
US5670527A (en) * 1993-07-16 1997-09-23 Smithkline Beecham Corporation Pyridyl imidazole compounds and compositions
US5593991A (en) * 1993-07-16 1997-01-14 Adams; Jerry L. Imidazole compounds, use and process of making
US5593992A (en) * 1993-07-16 1997-01-14 Smithkline Beecham Corporation Compounds
JPH09505055A (ja) 1993-11-08 1997-05-20 スミスクライン・ビーチャム・コーポレイション サイトカイン媒介疾患治療用オキサゾール
US5723477A (en) * 1994-11-10 1998-03-03 Sibia Neurosciences, Inc. Modulators of acetylcholine receptors
US5739143A (en) * 1995-06-07 1998-04-14 Smithkline Beecham Corporation Imidazole compounds and compositions
US5658903A (en) * 1995-06-07 1997-08-19 Smithkline Beecham Corporation Imidazole compounds, compositions and use
US6369068B1 (en) 1995-06-07 2002-04-09 Smithkline Beecham Corporation Amino substituted pyrimidine containing compounds
ZA9610687B (en) 1995-12-22 1997-09-29 Smithkline Beecham Corp Novel synthesis.
KR19990077164A (ko) * 1996-01-11 1999-10-25 스티븐 베네티아너 신규 치환된 이미다졸 화합물
AP9700912A0 (en) 1996-01-11 1997-01-31 Smithkline Beecham Corp Novel cycloalkyl substituted imidazoles
ZA97175B (en) * 1996-01-11 1997-11-04 Smithkline Beecham Corp Novel substituted imidazole compounds.
US6046208A (en) * 1996-01-11 2000-04-04 Smithkline Beecham Corporation Substituted imidazole compounds
WO1997035856A1 (en) * 1996-03-25 1997-10-02 Smithkline Beecham Corporation Novel treatment for cns injuries
WO1998007425A1 (en) 1996-08-21 1998-02-26 Smithkline Beecham Corporation Imidazole compounds, compositions and use
US5929076A (en) * 1997-01-10 1999-07-27 Smithkline Beecham Corporation Cycloalkyl substituted imidazoles
US5965583A (en) * 1997-04-24 1999-10-12 Ortho-Mcneil Pharmaceutical, Inc. Substituted imidazoles useful in the treatment of inflammatory disease
WO1998056377A1 (en) 1997-06-13 1998-12-17 Smithkline Beecham Corporation Novel pyrazole and pyrazoline substituted compounds
CA2294137A1 (en) 1997-06-19 1998-12-23 Smithkline Beecham Corporation Novel aryloxy substituted pyrimidine imidazole compounds
US7301021B2 (en) * 1997-07-02 2007-11-27 Smithkline Beecham Corporation Substituted imidazole compounds
AR016294A1 (es) * 1997-07-02 2001-07-04 Smithkline Beecham Corp Compuesto de imidazol sustituido, composicion farmaceutica que la contiene, su uso en la fabricacion de un medicamento y procedimiento para supreparacion
JP2002509537A (ja) 1997-07-02 2002-03-26 スミスクライン・ビーチャム・コーポレイション 新規なシクロアルキル置換イミダゾール化合物
TW517055B (en) 1997-07-02 2003-01-11 Smithkline Beecham Corp Novel substituted imidazole compounds
US6489325B1 (en) 1998-07-01 2002-12-03 Smithkline Beecham Corporation Substituted imidazole compounds
US6562832B1 (en) 1997-07-02 2003-05-13 Smithkline Beecham Corporation Substituted imidazole compounds
CA2306077A1 (en) 1997-10-08 1999-04-15 Smithkline Beecham Corporation Novel cycloalkenyl substituted compounds
EP1037639A4 (en) 1997-12-19 2002-04-17 Smithkline Beecham Corp HETEROARYL-SUBSTITUTED IMIDAZOLE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS AND USES
CN1548436A (zh) * 1998-05-22 2004-11-24 ʷ��˿�������ȳ�ķ���޹�˾ 新的2-烷基取代咪唑化合物
US6858617B2 (en) 1998-05-26 2005-02-22 Smithkline Beecham Corporation Substituted imidazole compounds
ATE266399T1 (de) * 1998-08-20 2004-05-15 Smithkline Beecham Corp Neue substituierte triazolverbindungen
US6548503B1 (en) 1998-11-04 2003-04-15 Smithkline Beecham Corporation Pyridin-4-yl or pyrimidin-4-yl substituted pyrazines
WO2000029399A1 (en) * 1998-11-12 2000-05-25 Boehringer Ingelheim (Canada) Ltd. Antiherpes compounds
US6239279B1 (en) 1998-12-16 2001-05-29 Smithkline Beecham Corporation Synthesis for 4-aryl-5-pyrimidine imidazole substituted derivatives
ATE382044T1 (de) 1999-11-22 2008-01-15 Smithkline Beecham Plc Imidazol- derivate
US6759410B1 (en) 1999-11-23 2004-07-06 Smithline Beecham Corporation 3,4-dihydro-(1H)-quinazolin-2-ones and their use as CSBP/p38 kinase inhibitors
US7053099B1 (en) 1999-11-23 2006-05-30 Smithkline Beecham Corporation 3,4-dihydro-(1H)quinazolin-2-one compounds as CSBP/p38 kinase inhibitors
EP1233951B1 (en) 1999-11-23 2005-06-01 SmithKline Beecham Corporation 3,4-dihydro-(1h)quinazolin-2-one compounds as csbp/p38 kinase inhibitors
AU1782301A (en) 1999-11-23 2001-06-04 Smithkline Beecham Corporation 3,4-dihydro-(1h)quinazolin-2-one compounds as csbp/p39 kinase inhibitors
US7235551B2 (en) * 2000-03-02 2007-06-26 Smithkline Beecham Corporation 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases
JP2003525936A (ja) * 2000-03-06 2003-09-02 スミスクライン ビーチャム パブリック リミテッド カンパニー Ｒａｆキナーゼ阻害物質としてのイミダゾール誘導体
GB0005357D0 (en) 2000-03-06 2000-04-26 Smithkline Beecham Plc Compounds
ES2372028T3 (es) * 2000-10-23 2012-01-13 Glaxosmithkline Llc Nuevo compuesto de 8h-pirido[2,3-d]pirimidin-7-ona trisustituida para el tratamiento de enfermedades mediadas por la csbp/p38 quinasa.
GB0112348D0 (en) * 2001-05-19 2001-07-11 Smithkline Beecham Plc Compounds
US20040192689A1 (en) * 2001-09-05 2004-09-30 Dean David Kenneth Heterocycle-carboxamide derivatives as raf kinase inhibitors
RU2312101C2 (ru) * 2001-12-18 2007-12-10 Ф.Хоффманн-Ля Рош Аг Цис-имидазолины в качестве ингибиторов mdm2
TW200505446A (en) * 2003-01-17 2005-02-16 Fuj Isawa Pharmaceutical Co Ltd Inhibitor of cox
CA2524889A1 (en) * 2003-05-08 2004-11-18 Astellas Pharma Inc. 1,2-diarylimidazoles useful as inhibitors of cox
TWI389690B (zh) 2005-03-25 2013-03-21 Glaxo Group Ltd 新穎化合物（一）
AU2006229995A1 (en) * 2005-03-25 2006-10-05 Glaxo Group Limited Process for preparing pyrido(2,3-d)pyrimidin-7-one and 3,4-dihydropyrimido(4,5-d)pyrimidin-2(1H)-one derivatives
WO2013049272A2 (en) * 2011-09-29 2013-04-04 Theraceutix, Llc Composition and method for treatment of symptoms associated with various skin conditions

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US3558645A (en) * 1968-07-08 1971-01-26 Sandoz Ag 2-(4-(4',5-diphenyl - 2 - imidazolyl)-phenoxy) lower aliphatic monocarboxylic acids
CH561717A5 (OSRAM) * 1971-05-10 1975-05-15 Ciba Geigy Ag
GB1469532A (en) * 1973-06-28 1977-04-06 Dumex Ltd As Imimdazolyl-alkanoic acid derivatives
US4372964A (en) * 1980-10-30 1983-02-08 E. I. Du Pont De Nemours And Company Antiinflammatory 4,5-diaryl-1H-imidazole-2-methanols

Also Published As

Publication number Publication date
NZ197828A (en) 1985-11-08
DD201677A5 (de) 1983-08-03
ES8307245A1 (es) 1983-07-01
SU1205764A3 (ru) 1986-01-15
NO812542L (no) 1982-01-26
ES514583A0 (es) 1983-05-16
KR850002750A (ko) 1985-05-15
PL237004A1 (en) 1983-02-28
ES514580A0 (es) 1983-05-16
ES8306119A1 (es) 1983-05-16
SU1138023A3 (ru) 1985-01-30
ES8306124A1 (es) 1983-05-16
AU7340481A (en) 1982-01-28
SU1152520A3 (en) 1985-04-23
ATE17349T1 (de) 1986-01-15
ZA815078B (en) 1982-07-28
PL237001A1 (en) 1983-02-28
ES514579A0 (es) 1983-05-16
PL236997A1 (en) 1983-01-03
KR850002753A (ko) 1985-05-15
KR850002744A (ko) 1985-05-15
PT73424B (en) 1983-06-20
KR850002752A (ko) 1985-05-15
SU1227112A3 (ru) 1986-04-23
SU1235454A3 (ru) 1986-05-30
KR850000887B1 (ko) 1985-06-26
PL237000A1 (en) 1983-02-28
KR850000891B1 (ko) 1985-06-26
AR230269A1 (es) 1984-03-01
ES504257A0 (es) 1982-12-01
SU1145928A3 (ru) 1985-03-15
ES8306122A1 (es) 1983-05-16
KR850000886B1 (ko) 1985-06-26
PL135822B1 (en) 1985-12-31
DK331881A (da) 1982-01-26
PL237005A1 (en) 1983-02-28
ES514581A0 (es) 1983-05-16
PL232352A1 (OSRAM) 1982-12-20
DE3173434D1 (en) 1986-02-20
FI812326L (fi) 1982-01-26
KR850002756A (ko) 1985-05-15
JPS5756466A (en) 1982-04-05
KR850000892B1 (ko) 1985-06-26
ES8301472A1 (es) 1982-12-01
KR850002754A (ko) 1985-05-15
KR850000888B1 (ko) 1985-06-26
KR850000911B1 (ko) 1985-06-27
KR850002755A (ko) 1985-05-15
IL63410A (en) 1986-04-29
ES514582A0 (es) 1983-05-16
ES514584A0 (es) 1983-05-16
ES8306123A1 (es) 1983-05-16
ES514585A0 (es) 1983-07-01
US4447431A (en) 1984-05-08
IL63410A0 (en) 1981-10-30
KR850002746A (ko) 1985-05-15
GR75287B (OSRAM) 1984-07-13
AU5655586A (en) 1986-09-11
KR850002747A (ko) 1985-05-15
EP0045081A3 (en) 1982-04-07
ES8306120A1 (es) 1983-05-16
KR850000889B1 (ko) 1985-06-26
KR850002745A (ko) 1985-05-15
ES8306121A1 (es) 1983-05-16
KR850000890B1 (ko) 1985-06-26
EP0045081A2 (de) 1982-02-03
PL237003A1 (en) 1983-02-28
EP0045081B1 (de) 1986-01-08
KR830006230A (ko) 1983-09-20
KR850001064B1 (ko) 1985-07-25
DD202554A5 (de) 1983-09-21
IE811680L (en) 1982-01-25
FI812326A7 (fi) 1982-01-26
KR850000873B1 (ko) 1985-06-22
PT73424A (en) 1981-08-01
SU1169534A3 (ru) 1985-07-23
PL237002A1 (en) 1983-02-28
GB2080805B (en) 1984-03-07
SU1205763A3 (ru) 1986-01-15
KR850002748A (ko) 1985-05-15
KR850000885B1 (ko) 1985-06-26
IE52071B1 (en) 1987-06-10
KR850000884B1 (ko) 1985-06-26
KR850000883B1 (ko) 1985-06-26
KR850002749A (ko) 1985-05-15
GB2080805A (en) 1982-02-10

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