US4371526A
Expired / Lapsed
US
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Phosphinylalkanoyl substituted 4,5-dihydropyrazole-5-carboxylic acid derivatives and hypotensive method and composition
Assignee: ER Squibb and Sons LLC
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Filing: 1981-08-21
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Granted: 1983-02-01
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Expires: 2001-08-21
Abstract
Abstract Compounds of the formula <IMAGE> are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity.
Inventors
- 👤 George C. Rovnyak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:58
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/06; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/301; C07F9/32; C07F9/3205; C07F9/3211; C07F9/48; C07F9/547; C07F9/645; C07F9/6503; C07F9/65031
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
185 words
A compound of the formula: ##STR101## or a basic, physiologically acceptable salt thereof wherein R and R 2 are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 4 carbons, benzyl, and ##STR102## R 3 is hydrogen, alkyl, ##STR103## R 1 is alkyl or ##STR104## R 4 is hydrogen, lower alkyl of 1 to 4 carbons, phenyl, or ##STR105## R 5 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, phenyl, or R 4 and R 5 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR106## R 6 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, or hydroxy; n is one, two or three provided that n is two or three only if R 6 is hydrogen, methyl, methoxy, chloro, or fluoro; R 7 is hydrogen, lower alkyl of 1 to 4 carbons, chloro, bromo, or fluoro; and m is zero or an integer from 1 to 8.
Claim 2
Dependent Claim
185 words
A compound of the formula: ##STR101## or a basic, physiologically acceptable salt thereof wherein R and R 2 are independently selected from the group consisting of hydrogen, lower alkyl of 1 to 4 carbons, benzyl, and ##STR102## R 3 is hydrogen, alkyl, ##STR103## R 1 is alkyl or ##STR104## R 4 is hydrogen, lower alkyl of 1 to 4 carbons, phenyl, or ##STR105## R 5 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, phenyl, or R 4 and R 5 taken together are --(CH 2 ) 2 --, --(CH 2 ) 3 --, --CH═CH--, or ##STR106## R 6 is hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, chloro, bromo, fluoro, trifluoromethyl, or hydroxy; n is one, two or three provided that n is two or three only if R 6 is hydrogen, methyl, methoxy, chloro, or fluoro; R 7 is hydrogen, lower alkyl of 1 to 4 carbons, chloro, bromo, or fluoro; and m is zero or an integer from 1 to 8.
Claim 3
Dependent Claim
97 words
A compound of claim 1 wherein: R and R 2 are independently selected from the group consisting of hydrogen, alkali metal, and ##STR107## provided that at least one of R and R 2 is hydrogen or alkali metal; R 3 is ##STR108## R 4 is hydrogen, methyl, or ##STR109## R 5 is lower alkyl of 1 to 4 carbons or phenyl; R 6 is hydrogen, methyl, methoxy, methylthio, trifluoromethyl, chloro, bromo, fluoro, or hydroxy; and R 1 is alkyl or ##STR110## wherein R 6 is as defined above and m is an integer from 2 to 6.
Claim 4
Dependent Claim
46 words
A compound of claim 2 wherein R and R 2 are independently selected from the group consisting of hydrogen, alkali metal, ##STR111## provided that at least one of R and R 2 is hydrogen or alkali metal; R 3 is phenyl; and R 1 is ##STR112##
Claim 5
Dependent Claim
12 words
The compound of claim 3 wherein R and R 2 are hydrogen.
Claim 6
Dependent Claim
7 words
The compound of claim 4, (+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]-acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid.
Claim 7
Dependent Claim
14 words
The compound of claim 3 wherein R 2 is hydrogen and R is ##STR113##
Claim 8
Dependent Claim
9 words
The compound of claim 6, (+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]-acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester.
Claim 9
Dependent Claim
14 words
The compound of claim 3 wherein R is hydrogen and R 2 is ##STR114##
Claim 10
Dependent Claim
7 words
The compound of claim 8, (+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid.
Claim 11
Dependent Claim
44 words
A composition useful for treating hypertension comprising a pharmaceutically acceptable carrier and an effective amount of a hypotensive agent or pharmaceutically acceptable salt thereof of the formula ##STR115## wherein R, R 1 , R 2 and R 3 are as defined in claim 1.
Claim 12
Dependent Claim
9 words
The composition of claim 10 also including a diuretic.
Claim 13
Dependent Claim
24 words
The method of alleviating hypertension in a mammalian specie suffering from hypertension which comprises administering an effective amount of the composition of claim 10.
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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) | 1986-01-31 | 1986-08-02 | 1987-02-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-01-31 | 1990-08-02 | 1991-02-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-01-31 | 1994-08-02 | 1995-02-01 | $7700.00 | Window Closed / Lapsed |