US4093726A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-(2-benzimidazolyl)-piperazines
Assignee: Abbott Laboratories
•
Filing: 1976-12-02
•
Granted: 1978-06-06
•
Expires: 1996-12-02
Abstract
Abstract Disclosed are compounds of the formula ##STR1## wherein n is 2 or 3, R is hydrogen or methyl, R' is C 1 -C 6 alkyl, acyl, aryl, aroyl, alkoxycarbonyl, tetrahydrofuroyl, dialkylaminocarbonyl, or furoyl, and R" is hydrogen and methoxy. These compounds are useful as antihypertensive agents.
Inventors
- 👤 Martin Winn
- 👤 Jaroslav Kyncl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:47
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A61; A61P; A61P9/00; A61P9/12; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/30; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/24; C07D307/34; C07D307/56; C07D307/68; C07D405/00; C07D405/02; C07D405/12
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
57 words
A compound of the formula: ##STR13## wherein: n is 2; R is selected from the group consisting of hydrogen or methyl; R' is C 1 -C 6 alkyl, 4-methyl valeroyl, phenyl, dimethoxyphenyl, CF 3 -phenyl, tetrahydrofuroyl, Furoyl, ##STR14## or C 2 -C 4 alkoxy carbonyl and R" is selected from the group consisting of hydrogen or methoxy.
Claim 2
Dependent Claim
57 words
A compound of the formula: ##STR13## wherein: n is 2; R is selected from the group consisting of hydrogen or methyl; R' is C 1 -C 6 alkyl, 4-methyl valeroyl, phenyl, dimethoxyphenyl, CF 3 -phenyl, tetrahydrofuroyl, Furoyl, ##STR14## or C 2 -C 4 alkoxy carbonyl and R" is selected from the group consisting of hydrogen or methoxy.
Claim 3
Dependent Claim
45 words
A compound selected from the group consisting of 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazole piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (3,4-dimethoxy-phenyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
45 words
A compound selected from the group consisting of 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazole piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (3,4-dimethoxy-phenyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
22 words
A compound selected from the group consisting of: 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, and 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine.
Claim 6
Dependent Claim
22 words
A compound selected from the group consisting of: 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, and 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine.
Claim 7
Dependent Claim
11 words
A compound in accordance with claim 3; 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester.
Claim 8
Dependent Claim
12 words
A compound in accordance with claim 3; 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester-hydrochloride.
Claim 9
Dependent Claim
58 words
An antihypertensive pharmaceutical composition comprising a compound selected from the group consisting of 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine, N (4-methyl valeroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof and a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
58 words
An antihypertensive pharmaceutical composition comprising a compound selected from the group consisting of 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine, N (4-methyl valeroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof and a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
36 words
A composition of claim 6 wherein the compound is selected from the group consisting of 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, and 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine and pharmaceutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim
20 words
The composition of claim 7 wherein the compound is 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester and pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim
21 words
The composition of claim 7 wherein the compound is 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester and pharmaceutically acceptable acid addition salts thereof.
Claim 14
Independent Claim
64 words
A method of treating hypertension in a mammal comprising administering to a mammal so afflicted a therapeutically effective amount of a compound selected from the groups consisting of: 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof.
Claim 15
Independent Claim
64 words
A method of treating hypertension in a mammal comprising administering to a mammal so afflicted a therapeutically effective amount of a compound selected from the groups consisting of: 1-(5,6-Dimethoxy-2-benzimidazolyl)-4-(2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester, 1-(5,6-Dimethoxy-1-methyl-2-benzimidazolyl)-4-(2-furoyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4 (tetrahydro-2-furoyl) piperazine, 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester, N,N-Dimethyl 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxamide, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3,4-dimethoxy-phenyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(4-methylvaleroyl) piperazine, 1-(5,6-Dimethoxy-2-benzimidazolyl)-4(3-trifluoromethyl phenyl) piperazine, 1-methyl 4(2-benzimidazolyl) piperazine and pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
13 words
The method of claim 10 wherein said compound is 4-(5,6-Dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic ethyl ester.
Claim 17
Dependent Claim
14 words
The method of claim 10 wherein said compound is 4-(5,6-dimethoxy-2-benzimidazolyl) piperazine-1-carboxylic acid isobutyl ester-hydrochloride.
Claim 18
Dependent Claim
41 words
A compound of the formula: ##STR15## wherein: R is selected from the group consisting of hydrogen or methyl; R' is C 2 -C 4 alkoxy carbonyl or N,N-dimethylamino carbonyl and R" is selected from the group consisting of hydrogen or methoxy.
Claim 19
Dependent Claim
41 words
A compound of the formula: ##STR15## wherein: R is selected from the group consisting of hydrogen or methyl; R' is C 2 -C 4 alkoxy carbonyl or N,N-dimethylamino carbonyl and R" is selected from the group consisting of hydrogen or methoxy.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |