US4544664A
Expired / Lapsed
US
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Antihypertensive substituted imidazole derivatives
Assignee: Orion Oyj
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Filing: 1982-07-07
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Granted: 1985-10-01
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Expires: 2002-07-07
Abstract
Abstract The invention provides novel compounds of the formula: ##STR1## wherein the various substituents are defined herein below. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions comprising at least one of the compounds of their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as antihypertensive agents. Furthermore, some of the compounds have proved to possess antithrombotic and diuretic activity. Antimycotic and antifungal properties have also been found.
Inventors
- 👤 Arto J. Karjalainen
- 👤 Kauko O. A. Kurkela
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:24
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/63; A; A61; A61P; A61P31/00; A61P31/04; A61P31/10; A61P7/00; A61P7/02; A61P7/10; A61P9/00; A61P9/12; C07C45/67; C07C45/68; C07C45/69; C07C45/72; C07C45/74; C07C49/00; C07C49/20; C07C49/213; C07C49/217; C07D; C07D233/00; C07D233/54; C07D233/56; C07D233/64; C07D405/00; C07D405/02; C07D405/06
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
182 words
A substituted imidazole of the formula: ##STR61## or a non-toxic pharmaceutically acceptable addition salt thereof, wherein R 1 is H, alkyl of 1 to 4 carbon atoms or --CH 2 OH; R 2 is H or --CH 3 ; R 3 is --CH 3 , --CH 2 CH 3 , --CH 2 CH 2 CH 3 , ##STR62## --CH 2 CH 2 CH 2 CH 3 , or --CH 2 CH═CH 2 , and R 4 is H or OH; or R 3 and R 4 together represent ═CH 2 , ═CH--CH 3 , ═CH--CH 2 --CH 3 , ##STR63## or ═CH--CH 2 CH 2 CH 2 CH 3 ; R 5 R 6 and R 7 which can be the same or different are H, --CH 3 , --CH 2 CH 3 , halogen, OH or --OCH 3 , at least one of R 5 , R 6 and R 7 being other than hydrogen, or R 5 is hydrogen and R 6 and R 7 together form an --O--CH 2 --O--bridge between two adjacent carbon atoms in the phenyl group.
Claim 2
Dependent Claim
182 words
A substituted imidazole of the formula: ##STR61## or a non-toxic pharmaceutically acceptable addition salt thereof, wherein R 1 is H, alkyl of 1 to 4 carbon atoms or --CH 2 OH; R 2 is H or --CH 3 ; R 3 is --CH 3 , --CH 2 CH 3 , --CH 2 CH 2 CH 3 , ##STR62## --CH 2 CH 2 CH 2 CH 3 , or --CH 2 CH═CH 2 , and R 4 is H or OH; or R 3 and R 4 together represent ═CH 2 , ═CH--CH 3 , ═CH--CH 2 --CH 3 , ##STR63## or ═CH--CH 2 CH 2 CH 2 CH 3 ; R 5 R 6 and R 7 which can be the same or different are H, --CH 3 , --CH 2 CH 3 , halogen, OH or --OCH 3 , at least one of R 5 , R 6 and R 7 being other than hydrogen, or R 5 is hydrogen and R 6 and R 7 together form an --O--CH 2 --O--bridge between two adjacent carbon atoms in the phenyl group.
Claim 3
Dependent Claim
50 words
A compound of formula (I) according to claim 1 wherein each of R 5 , R 6 and R 7 , which can be the same or different, is hydrogen, methyl, ethyl or halogen, at least one of R 5 , R 6 and R 7 being other than hydrogen.
Claim 4
Dependent Claim
24 words
A compound of formula (I) according to claim 1, wherein R 4 is hydrogen and R 3 is methyl, ethyl, propyl, isopropyl or butyl.
Claim 5
Dependent Claim
14 words
A compound of formula (I) according to claim 3 wherein R 1 is methyl.
Claim 6
Dependent Claim
18 words
A compound according to claim 1 which is 4-[(α-methyl)-2,6-dimethylbenzyl]imidazole or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
18 words
A cmpound according to claim 1 which is 4-[(α-methyl)-2,3-dimethylbenzyl]imidazole or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
18 words
A compound according to claim 1 which is 4-[(α-methyl)-2-methylbenzyl]imidazole or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
18 words
A compound according to claim 1 which is 4-[(α-methyl)-2-chlorobenzyl]imidazole or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
18 words
A compound according to claim 1 which is 4-[(α-ethyl)-2,3-dimethylbenzyl]imidazole or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
18 words
A compound according to claim 1 which is 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)-ethylene or a non-toxic pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
204 words
A pharmaceutical composition useful for producing an anti-hypertensive effect comprising an effective amount of a substituted imidazole of the formula: ##STR64## or a non-toxic pharmaceutically acceptable acid addition salt thereof, wherein R 1 is H, alkyl of 1 to 4 carbon atoms or --CH 2 OH; R 2 is H or --CH 3 ; R 3 is --CH 3 , --CH 2 CH 3 , --CH 2 CH 2 CH 3 , ##STR65## --CH 2 CH 2 CH 2 CH 3 , or --CH 2 CH═CH 2 , and R 4 is H or OH; or R 3 and R 4 together represent ═CH 2 , ═CH--CH 3 , ═CH--CH 2 --CH 3 , ##STR66## or ═CH--CH 2 CH 2 CH 2 CH 3 ; R 5 R 6 and R 7 which can be the same or different are H, --CH 3 , --CH 2 CH 3 , halogen, OH or --OCH 3 , at least one of R 5 , R 6 and R 7 being other than hydrogen, or R 5 is hydrogen and R 6 and R 7 together form an --O--CH 2 --O--bridge between two adjacent carbon atoms in the phenyl group, and a compatible, pharmaceutically acceptable carrier therefor.
Claim 13
Dependent Claim
204 words
A pharmaceutical composition useful for producing an anti-hypertensive effect comprising an effective amount of a substituted imidazole of the formula: ##STR64## or a non-toxic pharmaceutically acceptable acid addition salt thereof, wherein R 1 is H, alkyl of 1 to 4 carbon atoms or --CH 2 OH; R 2 is H or --CH 3 ; R 3 is --CH 3 , --CH 2 CH 3 , --CH 2 CH 2 CH 3 , ##STR65## --CH 2 CH 2 CH 2 CH 3 , or --CH 2 CH═CH 2 , and R 4 is H or OH; or R 3 and R 4 together represent ═CH 2 , ═CH--CH 3 , ═CH--CH 2 --CH 3 , ##STR66## or ═CH--CH 2 CH 2 CH 2 CH 3 ; R 5 R 6 and R 7 which can be the same or different are H, --CH 3 , --CH 2 CH 3 , halogen, OH or --OCH 3 , at least one of R 5 , R 6 and R 7 being other than hydrogen, or R 5 is hydrogen and R 6 and R 7 together form an --O--CH 2 --O--bridge between two adjacent carbon atoms in the phenyl group, and a compatible, pharmaceutically acceptable carrier therefor.
Claim 14
Dependent Claim
47 words
A method of producing an anti-hypertensive effect in a subject in whom such an effect is desired which comprises administering thereto an amount effective as an antihypertensive agent of a substituted imidazole as defined in claim 1 or of a non-toxic pharmaceutically acceptable acid addition salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-30 | 1989-04-01 | 1989-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-30 | 1993-04-01 | 1993-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-30 | 1997-04-01 | 1997-10-01 | $7700.00 | Window Closed / Lapsed |