US4241076A
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Halogenated substituted mercaptoacylamino acids
Assignee: ER Squibb and Sons LLC
•
Filing: 1979-05-09
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Granted: 1980-12-23
•
Expires: 1999-05-09
Abstract
Abstract New halogen substituted mercaptoacylamino acids which have the general formula ##STR1## and basic salts thereof are useful as hypotensive agents.
Inventors
- 👤 Miguel A. Ondetti
- 👤 Peter W. Sprague
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 04:12
CPC Classifications
C; C07; C07C; C07C53/00; C07C53/15; C07C53/19; C07C53/21; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/60
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
122 words
A compound of the formula ##STR18## wherein R is hydrogen, lower alkanoyl, ##STR19## m is zero, one, or two; R 1 is hydrogen or lower alkyl; R 2 , R 5 and R 6 each is hydrogen or halogen; R 3 is hydrogen, lower alkyl, halogen or trifluoromethyl provided that when n is zero R 3 is other than halogen; R 4 is hydrogen, lower alkyl or trifluoromethyl; and n is 0 or 1; with the provisos that at least one of R 2 , R 3 , R 4 , R 5 and R 6 as defined above is a halogen and that only R 2 and R 5 can both be halogen in the same compound; and basic salts thereof.
Claim 2
Dependent Claim
122 words
A compound of the formula ##STR18## wherein R is hydrogen, lower alkanoyl, ##STR19## m is zero, one, or two; R 1 is hydrogen or lower alkyl; R 2 , R 5 and R 6 each is hydrogen or halogen; R 3 is hydrogen, lower alkyl, halogen or trifluoromethyl provided that when n is zero R 3 is other than halogen; R 4 is hydrogen, lower alkyl or trifluoromethyl; and n is 0 or 1; with the provisos that at least one of R 2 , R 3 , R 4 , R 5 and R 6 as defined above is a halogen and that only R 2 and R 5 can both be halogen in the same compound; and basic salts thereof.
Claim 3
Dependent Claim
68 words
A compound of the formula ##STR20## wherein R is hydrogen, lower alkanoyl or ##STR21## R 1 is hydrogen or lower alkyl; R 2 and R 5 are each the same halogen or one is halogen and the other is hydrogen; R 3 and R 4 each is hydrogen or trifluoromethyl, one being hydrogen and the other trifluoromethyl; and n is 0 or 1; and physiologically acceptable salts thereof.
Claim 4
Dependent Claim
68 words
A compound of the formula ##STR20## wherein R is hydrogen, lower alkanoyl or ##STR21## R 1 is hydrogen or lower alkyl; R 2 and R 5 are each the same halogen or one is halogen and the other is hydrogen; R 3 and R 4 each is hydrogen or trifluoromethyl, one being hydrogen and the other trifluoromethyl; and n is 0 or 1; and physiologically acceptable salts thereof.
Claim 5
Dependent Claim
17 words
The compound of claim 2 wherein the proline as represented by the asterisk is in the L-configuration.
Claim 6
Dependent Claim
14 words
The compound of claim 3 wherein R 2 and R 5 are both fluorine.
Claim 7
Dependent Claim
14 words
The compound of claim 4 wherein R is acetyl and R 1 is hydrogen.
Claim 8
Dependent Claim
13 words
The compound of claim 4 wherein R and R 1 are both hydrogen.
Claim 9
Dependent Claim
18 words
The compound of claim 6 wherein n is one; R 3 is trifluoromethyl; and R 4 is hydrogen.
Claim 10
Dependent Claim
18 words
The compound of claim 6 wherein n is one; R 3 is hydrogen; and R 4 is trifluoromethyl.
Claim 11
Dependent Claim
15 words
The compound of claim 3 wherein R 2 is fluorine and R 5 is hydrogen.
Claim 12
Dependent Claim
14 words
The compound of claim 9 wherein R is acetyl and R 1 is hydrogen.
Claim 13
Dependent Claim
13 words
The compound of claim 9 wherein R and R 1 are both hydrogen.
Claim 14
Dependent Claim
15 words
The compound of claim 3 wherein R 2 is chlorine and R 5 is hydrogen.
Claim 15
Dependent Claim
14 words
The compound of claim 12 wherein R is acetyl and R 1 is hydrogen.
Claim 16
Dependent Claim
13 words
The compound of claim 12 wherein R and R 1 are both hydrogen.
Claim 17
Dependent Claim
114 words
A compound of the formula ##STR22## wherein R is hydrogen, lower alkanoyl, or ##STR23## R 1 is hydrogen or lower alkyl; R 2 and R 5 each is hydrogen or halogen provided that when R 2 and R 5 are both halogen the two halogens are the same; R 3 is hydrogen, halogen, or lower alkyl provided that R 3 is halogen when R 2 and R 5 are both hydrogen and R 3 is other than halogen when either or both R 2 and R 5 is halogen; R 4 is hydrogen; and n is zero or one provided that n is one when R 3 is halogen; and physiologically acceptable salts thereof.
Claim 18
Dependent Claim
114 words
A compound of the formula ##STR22## wherein R is hydrogen, lower alkanoyl, or ##STR23## R 1 is hydrogen or lower alkyl; R 2 and R 5 each is hydrogen or halogen provided that when R 2 and R 5 are both halogen the two halogens are the same; R 3 is hydrogen, halogen, or lower alkyl provided that R 3 is halogen when R 2 and R 5 are both hydrogen and R 3 is other than halogen when either or both R 2 and R 5 is halogen; R 4 is hydrogen; and n is zero or one provided that n is one when R 3 is halogen; and physiologically acceptable salts thereof.
Claim 19
Dependent Claim
17 words
The compound of claim 15 wherein the proline as represented by the asterisk is in the L-configuration.
Claim 20
Dependent Claim
22 words
The compound of claim 16 wherein R 2 and R 5 are both hydrogen; n is one; and R 3 is halogen.
Claim 21
Dependent Claim
12 words
The compound of claim 17 wherein R 3 is chlorine or bromine.
Claim 22
Dependent Claim
18 words
The compound of claim 18 wherein R 3 is chlorine; R is acetyl; and R 1 is hydrogen.
Claim 23
Dependent Claim
18 words
The compound of claim 18 wherein R 3 is bromine; R is acetyl; and R 1 is hydrogen.
Claim 24
Dependent Claim
21 words
The compound of claim 16 wherein R 2 and R 5 are both fluorine; and R 3 is hydrogen or methyl.
Claim 25
Dependent Claim
13 words
The compound of claim 21 wherein R and R 1 are both hydrogen.
Claim 26
Dependent Claim
14 words
The compound of claim 22 wherein n is one and R 3 is methyl.
Claim 27
Dependent Claim
6 words
The compound of claim 23, 4,4-difluoro-1-(D-3-mercapto-2-methylpropanoyl)-L-proline.
Claim 28
Dependent Claim
21 words
The compound of claim 16 wherein R 2 and R 5 are both chlorine; and R 3 is hydrogen or methyl.
Claim 29
Dependent Claim
13 words
The compound of claim 25 wherein R and R 1 are both hydrogen.
Claim 30
Dependent Claim
14 words
The compound of claim 26 wherein n is one and R 3 is methyl.
Claim 31
Dependent Claim
21 words
The compound of claim 16 wherein R 2 is fluorine; R 5 is hydrogen; and R 3 is hydrogen or methyl.
Claim 32
Dependent Claim
13 words
The compound of claim 28 wherein R and R 1 are both hydrogen.
Claim 33
Dependent Claim
14 words
The compound of claim 29 wherein n is one and R 3 is methyl.
Claim 34
Dependent Claim
6 words
The compound of claim 30, cis-4-fluoro-1-(D-3-mercapto-2-methylpropanoyl)-2-proline.
Claim 35
Dependent Claim
6 words
The compound of claim 30, trans-4-fluoro-1-(D-3-mercapto-2-methylpropanoyl)-L-proline.
Claim 36
Dependent Claim
21 words
The compound of claim 16 wherein R 2 is chlorine; R 5 is hydrogen; and R 3 is hydrogen or methyl.
Claim 37
Dependent Claim
13 words
The compound of claim 33 wherein R and R 1 are both hydrogen.
Claim 38
Dependent Claim
14 words
The compound of claim 34 wherein n is one and R 3 is methyl.
Claim 39
Dependent Claim
6 words
The compound of claim 35, cis-4-chloro-1-(D-3-mercapto-2-methylpropanoyl)-L-proline.
Claim 40
Dependent Claim
38 words
A method for alleviating hypertension in a hypertensive mammal which comprises administering to said mammal an effective amount of a composition comprising a compound of claim 1 or physiologically acceptable salt thereof and a pharmaceutically acceptable vehicle therefor.
Claim 41
Dependent Claim
34 words
A composition useful for alleviating hypertension in a hypertensive mammal comprising from about 10 to 500 mg. of a compound of claim 1 or physiologically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.
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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) | 1983-12-23 | 1984-06-23 | 1984-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-23 | 1988-06-23 | 1988-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-23 | 1992-06-23 | 1992-12-23 | $7700.00 | Window Closed / Lapsed |