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, ***e
    • 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

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
DEP4031287.9 1990-10-04
DE4031287A DE4031287A1 (en) 1990-07-23 1990-10-04 New 1-bi:phenylyl:methyl benzimidazole derivs.
DEP4105324.9 1991-02-20
DE4105324A DE4105324A1 (en) 1990-07-23 1991-02-20 New 1-bi:phenylyl:methyl benzimidazole derivs.

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
DE4224133A1 (en) * 1992-07-22 1994-01-27 Thomae Gmbh Dr K Benzimidazoles, medicaments containing these compounds and process for their preparation
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
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
IL103020A (en) * 1991-09-10 1998-10-30 Tanabe Seiyaku Co 3-(1,1'-Biphenyl-4-yl-methyl)-4,5,6,7-tetrahydro-3h-imidazo Ú4,5-c¾ pyridine-4-carboxylic acids their preparation and pharmaceutical compositions containing them
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 New bi:phenyl-methyl-benzimidazole derivs.
US5753672A (en) * 1994-04-19 1998-05-19 Tanabe Seiyaku Co., Ltd. Imidazopyridine derivatives and process for preparing the same
PL318199A1 (en) * 1994-06-29 1997-05-26 Smithkline Beecham Corp Antagonists of vitronectin receptors
EP0882718B1 (en) * 1995-12-28 2005-08-31 Fujisawa 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
PT1685126E (en) * 2003-10-16 2007-04-30 Teva Pharma Preparation of candesartan cilexetil
CA2581723A1 (en) * 2004-10-15 2006-04-27 Teva Pharmaceutical Industries Ltd. Process for preparing telmisartan
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
US7879802B2 (en) 2007-06-04 2011-02-01 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP3239170B1 (en) 2008-06-04 2019-03-20 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
EP3241839B1 (en) 2008-07-16 2019-09-04 Bausch Health Ireland Limited Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
CA2762620A1 (en) 2009-05-29 2010-12-02 Sumitomo Chemical Company, Limited Agent for treatment or prevention of diseases associated with activity of neurotrophic factors
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
US9708367B2 (en) 2013-03-15 2017-07-18 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
CA2905435A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
JP6606491B2 (en) 2013-06-05 2019-11-13 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 Ultra high purity agonist of guanylate cyclase C, method for producing and using the same
AU2014284616B2 (en) 2013-06-21 2019-02-28 Zenith Epigenetics Ltd. Novel bicyclic bromodomain inhibitors
CA2915622C (en) 2013-06-21 2020-08-18 Zenith Epigenetics Corp. Novel substituted bicyclic compounds as bromodomain inhibitors
CA2919948C (en) 2013-07-31 2020-07-21 Zenith Epigenetics Corp. Novel quinazolinones as bromodomain inhibitors
CN107108552A (en) * 2014-08-05 2017-08-29 百时美施贵宝公司 Heterocyclic kinase inhibitors
EP3227281A4 (en) 2014-12-01 2018-05-30 Zenith Epigenetics Ltd. Substituted pyridinones as bromodomain inhibitors
CA2966449A1 (en) 2014-12-11 2016-06-16 Zenith Epigenetics Ltd. Substituted heterocycles as bromodomain inhibitors
JP2017538721A (en) 2014-12-17 2017-12-28 ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． Bromodomain inhibitors

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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
CA2016710A1 (en) * 1989-05-15 1990-11-15 Prasun K. Chakravarty Substituted benzimidazoles as angiotensin ii antagonists
JP2568315B2 (en) * 1989-06-30 1997-01-08 イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー Fused ring aryl substituted imidazole
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
FI105811B (en) 2000-10-13
IE912563A1 (en) 1992-01-29
PT98414B (en) 1999-01-29
NO178927B (en) 1996-03-25
HU912456D0 (en) 1991-12-30
IL98933A (en) 1995-12-31
FI913503A0 (en) 1991-07-22
NO912859D0 (en) 1991-07-22
NO912859L (en) 1992-01-24
IL98933A0 (en) 1992-07-15
DK0468470T3 (en) 1997-09-22
NZ239089A (en) 1994-07-26
EP0468470A1 (en) 1992-01-29
ATE151766T1 (en) 1997-05-15
CA2047496C (en) 2001-10-23
CS230491A3 (en) 1992-02-19
DE59108658D1 (en) 1997-05-22
ES2100907T3 (en) 1997-07-01
JPH04253966A (en) 1992-09-09
AU640505B2 (en) 1993-08-26
NO178927C (en) 1996-07-03
GR3024027T3 (en) 1997-10-31
AU8122791A (en) 1992-01-30
RU1836357C (en) 1993-08-23
HUT58298A (en) 1992-02-28
PT98414A (en) 1992-05-29
FI913503A (en) 1992-01-24
JP2539113B2 (en) 1996-10-02
EP0468470B1 (en) 1997-04-16

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