US5376671A
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Propenoyl-imidazole derivatives
Assignee: Bayer AG
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Filing: 1993-04-06
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Granted: 1994-12-27
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Expires: 2013-04-06
Abstract
Abstract Propenoyl-imidazole derivatives are prepared by reaction of appropriate imidazoylaldehydes with CH-acidic compounds and subsequent dehydration of the intermediates. The propenoyl-imidazole derivatives can be employed as active compounds in medicaments for the treatment of arterial hypertension and atherosclerosis.
Inventors
- 👤 Matthias Muller-Gliemann
- 👤 Jurgen Dressel
- 👤 Peter Fey
- 👤 Rudolf Hanko
- 👤 Walter Hubsch
- 👤 Thomas Kramer
- 👤 Ulrich Muller
- 👤 Martin Beuck
- 👤 Stanislav Kazda
- 👤 Andreas Knorr
- 👤 Johannes-Peter Stasch
- 👤 Stefan Wohlfeil
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:42
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/56; C07D233/58; C07D233/66; C07D233/68; A; A61; A61P; A61P9/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
296 words
A propenoyl-imidazole of the formula ##STR47## in which R 1 represents straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms, or represents cycloalkyl having 3 to 8 carbon atoms, R 2 represents hydrogen, halogen or perfluoroalkyl having up to 5 carbon atoms, n represents a number 0, 1, 2 or 3, R 3 represents cycloalkyl having 3 to 7 carbon atoms, R 4 represents hydroxyl, or straight-chain or branched alkoxy having up to 6 carbon atoms, or represents a radical of the formula --CO--NR 7 R 8 , in which R 7 and R 8 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl, R 5 represents hydrogen, halogen, nitro, hydroxyl, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkyl, alkoxy or alkoxycarbonyl, each having up to 6 carbon atoms, cyano or carboxyl, L represents cycloalkyl having 3 to 7 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by phenyl, R 6 represents hydroxyl or straight-chain or branched alkoxy having up to 6 carbon atoms, or represents a radical of the formula --NR 9 SO 2 R 10 or ##STR48## in which R 9 denotes hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, R 10 denotes straight-chain or branched alkyl having up to 6 carbon atoms or phenyl which is optionally substituted by straight-chain or branched alkyl having up to 6 carbon atoms, R 11 denotes hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or a hydroxyl-protective group selected from the group consisting of benzyloxycarbonyl, methanesulphonyl, toluenesulphonyl, 2-nitrobenzyloxycarbonyl, tert-butoxycarbonyl, allyloxycarbonyl, 4-methoxycarbonyl, acetyl, trichloroacetyl, 2,2,2- trichloroethoxycarbonyl, 2,4-dimethoxybenzylcarbonyl, 2-(methylthiomethoxy)ethoxycarbonyl, benzoyl, 4-methylbenzoyl, 4-nitrobenzoyl, 4-fluorobenzoyl, 4-chlorobenzoyl and 4-methoxybenzoyl, or a salt thereof.
Claim 2
Dependent Claim
296 words
A propenoyl-imidazole of the formula ##STR47## in which R 1 represents straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms, or represents cycloalkyl having 3 to 8 carbon atoms, R 2 represents hydrogen, halogen or perfluoroalkyl having up to 5 carbon atoms, n represents a number 0, 1, 2 or 3, R 3 represents cycloalkyl having 3 to 7 carbon atoms, R 4 represents hydroxyl, or straight-chain or branched alkoxy having up to 6 carbon atoms, or represents a radical of the formula --CO--NR 7 R 8 , in which R 7 and R 8 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl, R 5 represents hydrogen, halogen, nitro, hydroxyl, trifluoromethyl, trifluoromethoxy, straight-chain or branched alkyl, alkoxy or alkoxycarbonyl, each having up to 6 carbon atoms, cyano or carboxyl, L represents cycloalkyl having 3 to 7 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by phenyl, R 6 represents hydroxyl or straight-chain or branched alkoxy having up to 6 carbon atoms, or represents a radical of the formula --NR 9 SO 2 R 10 or ##STR48## in which R 9 denotes hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, R 10 denotes straight-chain or branched alkyl having up to 6 carbon atoms or phenyl which is optionally substituted by straight-chain or branched alkyl having up to 6 carbon atoms, R 11 denotes hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or a hydroxyl-protective group selected from the group consisting of benzyloxycarbonyl, methanesulphonyl, toluenesulphonyl, 2-nitrobenzyloxycarbonyl, tert-butoxycarbonyl, allyloxycarbonyl, 4-methoxycarbonyl, acetyl, trichloroacetyl, 2,2,2- trichloroethoxycarbonyl, 2,4-dimethoxybenzylcarbonyl, 2-(methylthiomethoxy)ethoxycarbonyl, benzoyl, 4-methylbenzoyl, 4-nitrobenzoyl, 4-fluorobenzoyl, 4-chlorobenzoyl and 4-methoxybenzoyl, or a salt thereof.
Claim 3
Dependent Claim
252 words
A propenoyl-imidazole according to claim 1, in which R 1 represents straight-chain or branched alkyl or alkenyl each having up to 6 carbon atoms, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, R 2 represents hydrogen, fluorine, chlorine, bromine or perfluoroalkyl having up to 4 carbon atoms, n represents a number 0, 1 or 2, R 3 represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, R 4 represents hydroxyl, straight-chain or branched alkoxy having up to 4 carbon atoms, or represents the group of the formula --CO--NR 7 R 8 , in which R 7 and R 8 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms or phenyl, R 5 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, carboxyl or straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 4 carbon atoms, L represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, or represents straight-chain or branched alkyl having up to 6 carbon atoms or benzyl, R 6 represents hydroxyl or straight-chain or branched alkoxy having up to 4 carbon atoms, or represents a radical of the formula --NR 9 SO 2 R 10 or ##STR49## in which R 9 denotes hydrogen, methyl or ethyl, R 10 denotes straight-chain or branched alkyl having up to 4 carbon atoms or phenyl which is optionally substituted by straight-chain or branched alkyl having up to 4 carbon atoms, R 11 denotes hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms, acetyl or benzyl, or a salt thereof.
Claim 4
Dependent Claim
161 words
A propenoyl-imidazole according to claim 1, in which R 1 represents straight-chain or branched alkyl or alkenyl, each having up to 4 carbon atoms, or represents cyclopropyl, cyclopentyl or cyclohexyl, R 2 represents hydrogen, fluorine, chlorine or perfluoroalkyl having up to 2 carbon atoms, n represents the number 0 or 1, R 3 represents cyclopentyl or cyclohexyl, R 4 represents hydroxyl, methoxy, ethoxy or tert-butoxy, R 5 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy or methyl, L represents cyclopentyl, cyclohexyl or cycloheptyl, or represents straight-chain or branched alkyl having up to 4 carbon atoms or benzyl, R 6 represents hydroxyl or straight-chain or branched alkoxy having up to 4 carbon atoms, or represents a radical of the formula --NR 9 SO 2 R 10 or ##STR50## in which R 9 denotes hydrogen or methyl, R 10 denotes methyl or p-tolyl, R 11 denotes hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms or benzyl, or a salt thereof.
Claim 5
Dependent Claim
20 words
A propenoyl-imidazole according to claim 1 in which the radical --CH(L)--CO--R 4 is in the para-position to the imidazolylmethyl group.
Claim 6
Dependent Claim
21 words
A compound according to claim 1 wherein such compound is 2-[4-{2-n-butyl-4-chloro-5-(3-cyclohexyl-2-methoxycarbonyl-prop-1-en-yl)-1-H-imidazol-1-methyl}phenyl]-2-cyclopentyl-acetic acid-4L-phenyl glycinolamide of the formula ##STR51## or a salt thereof.
Claim 7
Dependent Claim
19 words
A compound according to claim 1 wherein such compound is N-4-toluenesulphonyl-2-[4-{2-n-butyl-4-chloro-5-(3-cyclohexyl-2-carboxy-prop-1-en-yl)-1H-imidazol-1-yl-methyl}phenyl]-2-cyclopentyl-acetamide of the formula ##STR52## or a salt thereof.
Claim 8
Dependent Claim
21 words
A compound according to claim 1 wherein such compound is 2-[4-{2-n-butyl-4-chloro-5-(3-cyclohexyl-2-carboxy-prop-1-en-yl)-1H-imidazol-1-yl-methyl}]-2-isopropyl-acetic acid-L-phenyl-glycinol amide of the formula ##STR53## or a salt thereof.
Claim 9
Dependent Claim
20 words
A compound according to claim 1 wherein such compound is 2-[4-{2-n-butyl-4-chloro-5-(3-cyclohexyl-2-carboxy-prop-1-en-yl)-1H-imidazol-1-yl-methyl}phenyl]-2-cycloheptyl-acetic acid of the formula ##STR54## or a salt thereof.
Claim 10
Dependent Claim
23 words
A compound according to claim 1 wherein such compound is 2-[4-{2-n-butyl-4-chloro-5-(3-cyclohexyl-2-methoxy-carbonyl-prop-1 -en-yl)-1H-imidazol-1-yl -methyl}phenyl]-2-cycloheptyl-acetic acid-L-phenyl-glycinol amide of the formula ##STR55## or a salt thereof.
Claim 11
Dependent Claim
30 words
A composition for the treatment of atriable hypertension and arteriosclerosis comprising an amount effective therefor of a compound or salt thereof according to claim 1 and a pharmacologically acceptable diluent.
Claim 12
Dependent Claim
34 words
The method of treating atriable hypertension and arteriosclerosis in a patient in need thereof which comprises administering to such patient an amount effective therefor of a compound or salt thereof according to claim 1.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1997-12-26 | 1998-06-27 | 1998-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-12-26 | 2002-06-27 | 2002-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-12-26 | 2006-06-27 | 2006-12-27 | $7700.00 | Window Closed / Lapsed |