CA2047496A1 - Benzimidazoles, pharmaceutical compositions containing these compounds and processes for preparing them - Google Patents

Benzimidazoles, pharmaceutical compositions containing these compounds and processes for preparing them

Info

Publication number
CA2047496A1
CA2047496A1 CA002047496A CA2047496A CA2047496A1 CA 2047496 A1 CA2047496 A1 CA 2047496A1 CA 002047496 A CA002047496 A CA 002047496A CA 2047496 A CA2047496 A CA 2047496A CA 2047496 A1 CA2047496 A1 CA 2047496A1
Authority
CA
Canada
Prior art keywords
oxo
benzimidazoles
compounds
preparing
processes
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.)
Granted
Application number
CA002047496A
Other languages
French (fr)
Other versions
CA2047496C (en
Inventor
Berthold Narr
Norbert Hauel
Jacques Van Meel
Wolfgang Wienen
Michael Entzeroth
Uwe Ries
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Individual
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 DE4023369A external-priority patent/DE4023369A1/en
Application filed by Individual filed Critical Individual
Publication of CA2047496A1 publication Critical patent/CA2047496A1/en
Application granted granted Critical
Publication of CA2047496C publication Critical patent/CA2047496C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity 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
    • 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
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • 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
    • C07D235/08—Radicals containing only hydrogen and 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
    • C07D403/10—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 aromatic rings
    • 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
    • C07D403/14—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 three or more hetero rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Toys (AREA)
  • Instructional Devices (AREA)

Abstract

The invention .relates to benzimidazoles of formula I
(see formula I) their 1-, 3-isomer mixtures, and the salts thereof, wherein the substituents R1, R2, R3 and R4 are preferably as follows: R1 in the 6-position represents a 1-methylbenzimidazol-2-yl, 3,4,5,6-tetrahydro-phthalimino, 2,3-diphenyl-maleic acid imido, 2,3-dimethyl-maleic acid imido, N-phenylmethanesulphonyl.-methylamino, 2-oxo-pyrrolidin-1-yl, 2-oxo-piperidin-1-yl, 2-oxo-hexamethyleneimino, 2-oxo-3, 4-tetramethylene-pyrrolidin-2-yl, 3,3-dimethylglutarimido, N-methylaminocarbonyl-n-pentylamino, propanesultam-1-yl or butanesultam-1-yl group; R2 represents a methyl, ethyl, n-propyl or n-butyl group; R3 represents a carboxy or 1H-tetrazolyl group; and R4 represents a hydrogen atom. These compounds have valuable properties, in particular as angiotensin-II antagonists.
CA002047496A 1990-07-23 1991-07-22 Benzimidazoles, pharmaceutical compositions containing these compounds and processes for preparing them Expired - Lifetime CA2047496C (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE4023369A DE4023369A1 (en) 1990-07-23 1990-07-23 New 1-bi:phenylyl:methyl benzimidazole derivs.
DEP4023369.3 1990-07-23
DE4031287A DE4031287A1 (en) 1990-07-23 1990-10-04 BENZIMIDAZOLE, MEDICAMENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
DEP4031287.9 1990-10-04
DE4105324A DE4105324A1 (en) 1990-07-23 1991-02-20 BENZIMIDAZOLE, MEDICAMENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
DEP4105324.9 1991-02-20

Publications (2)

Publication Number Publication Date
CA2047496A1 true CA2047496A1 (en) 1992-01-24
CA2047496C CA2047496C (en) 2001-10-23

Family

ID=27201487

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002047496A Expired - Lifetime CA2047496C (en) 1990-07-23 1991-07-22 Benzimidazoles, pharmaceutical compositions containing these compounds and processes for preparing them

Country Status (18)

Country Link
EP (1) EP0468470B1 (en)
JP (1) JP2539113B2 (en)
AT (1) ATE151766T1 (en)
AU (1) AU640505B2 (en)
CA (1) CA2047496C (en)
CS (1) CS230491A3 (en)
DE (1) DE59108658D1 (en)
DK (1) DK0468470T3 (en)
ES (1) ES2100907T3 (en)
FI (1) FI105811B (en)
GR (1) GR3024027T3 (en)
HU (1) HUT58298A (en)
IE (1) IE912563A1 (en)
IL (1) IL98933A (en)
NO (1) NO178927C (en)
NZ (1) NZ239089A (en)
PT (1) PT98414B (en)
RU (1) RU1836357C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5594003A (en) * 1991-02-06 1997-01-14 Dr. Karl Thomae Gmbh Tetrahydroimidazo[1,2-a]pyridin-2-yl-(benzimidazol-1-yl)-methyl-biphenyls useful as angiotensin-II antagonists
US5602127A (en) * 1991-02-06 1997-02-11 Karl Thomae Gmbh (Alkanesultam-1-yl)-benzimidazol-1-yl)-1yl)-methyl-biphenyls useful as angiotensin-II antagonists
US5614519A (en) * 1991-02-06 1997-03-25 Karl Thomae Gmbh (1-(2,3 or 4-N-morpholinoalkyl)-imidazol-4-yl)-benizimidazol-1-yl-methyl]-biphenyls useful as angiotensin-II antagonists

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8904174D0 (en) * 1989-02-23 1989-04-05 British Bio Technology Compounds
NZ232785A (en) * 1989-03-15 1991-03-26 Janssen Pharmaceutica Nv 5-(1,2 benzisoxazol-, benzimidazol and benzisothiazol-3- yl)-1h-benzimadazol-2-yl carbamic acid ester derivatives preparatory processes, intermediates and anthelmintic compositions
IE70593B1 (en) * 1989-09-29 1996-12-11 Eisai Co Ltd Biphenylmethane derivative the use of it and pharmacological compositions containing same
DE4224752A1 (en) * 1992-04-11 1994-02-03 Thomae Gmbh Dr K Benzimidazoles, medicaments containing these compounds and process for their preparation
SI9210098B (en) * 1991-02-06 2000-06-30 Dr. Karl Thomae Benzimidazoles, drugs with this compounds, and process for their preparation
DE4224133A1 (en) * 1992-07-22 1994-01-27 Thomae Gmbh Dr K Benzimidazoles, medicaments containing these compounds and process for their preparation
DE4225756A1 (en) * 1992-01-22 1994-03-10 Thomae Gmbh Dr K Benzimidazoles, medicaments containing these compounds and process for their preparation
US5798364A (en) * 1992-03-26 1998-08-25 Merck Patent Gesellschaft Mit Beschrankter Haftung Imidazopyridines
AU644540B2 (en) * 1991-09-10 1993-12-09 Tanabe Seiyaku Co., Ltd. Imidazopyridine derivatives and process for preparation thereof
EP0543263A3 (en) * 1991-11-16 1993-08-25 Dr. Karl Thomae Gmbh Benziimidazoles, pharmaceuticals containing them and process for their preparation
DE4219534A1 (en) * 1992-02-19 1993-12-16 Thomae Gmbh Dr K Substituted biphenylyl derivatives, pharmaceutical compositions containing them and methods for their preparation
DE4207904A1 (en) * 1992-03-12 1993-09-16 Thomae Gmbh Dr K SUBSTITUTED BENZIMIDAZOLYL DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF
US5612360A (en) * 1992-06-03 1997-03-18 Eli Lilly And Company Angiotensin II antagonists
DE4237656A1 (en) * 1992-06-13 1993-12-16 Merck Patent Gmbh benzimidazole derivatives
GB9218449D0 (en) 1992-08-29 1992-10-14 Boots Co Plc Therapeutic agents
DE4304455A1 (en) * 1993-02-15 1994-08-18 Bayer Ag Heterocyclic substituted phenyl-cyclohexane-carboxylic acid derivatives
DE4408497A1 (en) * 1994-03-14 1995-09-21 Thomae Gmbh Dr K Benzimidazoles, medicaments containing these compounds and process for their preparation
US5753672A (en) * 1994-04-19 1998-05-19 Tanabe Seiyaku Co., Ltd. Imidazopyridine derivatives and process for preparing the same
MX9700041A (en) * 1994-06-29 1997-04-30 Smithkline Beecham Corp Vitronectin receptor antagonists.
BR9612434A (en) * 1995-12-28 1999-12-28 Fujiwasa Pharmaceutical Co Ltd Benzimidazole derivatives
TW453999B (en) 1997-06-27 2001-09-11 Fujisawa Pharmaceutical Co Benzimidazole derivatives
SE9903028D0 (en) 1999-08-27 1999-08-27 Astra Ab New use
DE10314702A1 (en) * 2003-03-31 2004-10-21 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for the preparation of telmisartan
ATE357442T1 (en) * 2003-10-16 2007-04-15 Teva Pharma METHOD FOR PRODUCING CANDESARTAN CILEXETIL
JP2008503595A (en) * 2004-10-15 2008-02-07 テバ ファーマシューティカル インダストリーズ リミティド Preparation of telmisartan
JP5546451B2 (en) 2007-06-04 2014-07-09 シナジー ファーマシューティカルズ インコーポレイテッド Agonyl cyclase agonists useful in the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
ES2627848T3 (en) 2008-06-04 2017-07-31 Synergy Pharmaceuticals Inc. Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
ES2624828T3 (en) 2008-07-16 2017-07-17 Synergy Pharmaceuticals Inc. Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer and others
JP2011006409A (en) * 2009-05-29 2011-01-13 Sumitomo Chemical Co Ltd Therapeutic or prophylactic drug for disease associated with activity of neurotrophic factor
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
EP2968439A2 (en) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
US9708367B2 (en) 2013-03-15 2017-07-18 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
PL3004138T3 (en) 2013-06-05 2024-07-29 Bausch Health Ireland Limited Ultra-pure agonists of guanylate cyclase c, method of making and using same
BR112015031073B1 (en) 2013-06-21 2022-11-29 Zenith Epigenetics Ltd BICYCLIC BROMODIMANIUM INHIBITORS AND PHARMACEUTICAL COMPOSITION CONTAINING SAID COMPOUNDS
CN105473581B (en) 2013-06-21 2019-04-23 齐尼思表观遗传学有限公司 Newly substituted bicyclic compounds as bromodomain inhibitors
US9855271B2 (en) 2013-07-31 2018-01-02 Zenith Epigenetics Ltd. Quinazolinones as bromodomain inhibitors
US10035777B2 (en) * 2014-08-05 2018-07-31 Bristol-Myers Squibb Company Heterocyclic kinase inhibitors
HK1245246A1 (en) 2014-12-01 2018-08-24 恒翼生物医药科技(上海)有限公司 Substituted pyridinones as bromodomain inhibitors
JP2017537946A (en) 2014-12-11 2017-12-21 ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． Substituted heterocycles as bromodomain inhibitors
EP3233846A4 (en) 2014-12-17 2018-07-18 Zenith Epigenetics Ltd. Inhibitors of bromodomains

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4820843A (en) * 1987-05-22 1989-04-11 E. I. Du Pont De Nemours And Company Tetrazole intermediates to antihypertensive compounds
US4880804A (en) * 1988-01-07 1989-11-14 E. I. Du Pont De Nemours And Company Angiotensin II receptor blocking benzimidazoles
EP0400835A1 (en) * 1989-05-15 1990-12-05 Merck & Co. Inc. Substituted benzimidazoles as angiotensin II antagonists
EP0479892A1 (en) * 1989-06-30 1992-04-15 E.I. Du Pont De Nemours And Company Fused-ring aryl substituted imidazoles
IE70593B1 (en) * 1989-09-29 1996-12-11 Eisai Co Ltd Biphenylmethane derivative the use of it and pharmacological compositions containing same
IL95975A (en) * 1989-10-24 1997-06-10 Takeda Chemical Industries Ltd N-benzyl- 2-alkylbenzimidazole derivatives, their production and pharmaceutical compositions containing them
IL96019A0 (en) * 1989-10-31 1991-07-18 Fujisawa Pharmaceutical Co Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5594003A (en) * 1991-02-06 1997-01-14 Dr. Karl Thomae Gmbh Tetrahydroimidazo[1,2-a]pyridin-2-yl-(benzimidazol-1-yl)-methyl-biphenyls useful as angiotensin-II antagonists
US5602127A (en) * 1991-02-06 1997-02-11 Karl Thomae Gmbh (Alkanesultam-1-yl)-benzimidazol-1-yl)-1yl)-methyl-biphenyls useful as angiotensin-II antagonists
US5614519A (en) * 1991-02-06 1997-03-25 Karl Thomae Gmbh (1-(2,3 or 4-N-morpholinoalkyl)-imidazol-4-yl)-benizimidazol-1-yl-methyl]-biphenyls useful as angiotensin-II antagonists

Also Published As

Publication number Publication date
PT98414A (en) 1992-05-29
EP0468470B1 (en) 1997-04-16
NZ239089A (en) 1994-07-26
RU1836357C (en) 1993-08-23
DK0468470T3 (en) 1997-09-22
AU8122791A (en) 1992-01-30
JPH04253966A (en) 1992-09-09
ES2100907T3 (en) 1997-07-01
FI913503A7 (en) 1992-01-24
HU912456D0 (en) 1991-12-30
CS230491A3 (en) 1992-02-19
IL98933A (en) 1995-12-31
HUT58298A (en) 1992-02-28
ATE151766T1 (en) 1997-05-15
PT98414B (en) 1999-01-29
DE59108658D1 (en) 1997-05-22
FI105811B (en) 2000-10-13
NO912859D0 (en) 1991-07-22
NO178927B (en) 1996-03-25
JP2539113B2 (en) 1996-10-02
EP0468470A1 (en) 1992-01-29
NO178927C (en) 1996-07-03
NO912859L (en) 1992-01-24
IE912563A1 (en) 1992-01-29
IL98933A0 (en) 1992-07-15
AU640505B2 (en) 1993-08-26
FI913503A0 (en) 1991-07-22
CA2047496C (en) 2001-10-23
GR3024027T3 (en) 1997-10-31

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