US4154840A
Expired / Lapsed
US
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Antihypertensive pipecolic acid derivatives
Assignee: ER Squibb and Sons LLC
•
Filing: 1978-03-09
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Granted: 1979-05-15
•
Expires: 1998-03-09
Abstract
Abstract New proline derivatives and related compounds which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
Inventors
- 👤 Miguel A. Ondetti
- 👤 David W. Cushman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:20
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/60; A; A61; A61P; A61P43/00; A61P9/00; A61P9/12; C07C; C07C321/00; C07C323/00; C07C327/00; C07C53/00; C07C53/15; C07C53/19; C07C57/00; C07C57/52; C07C57/58; C07D205/00; C07D205/02; C07D205/04; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
150 words
A compound of the formula ##STR36## wherein R is hydroxy, NH 2 or lower alkoxy; R 1 and R 4 each is hydrogen, lower alkyl, phenyl or phenyl-lower alkyl; R 2 is hydrogen, lower alkyl, phenyl, substituted phenyl wherein the phenyl substituent is halo, lower alkyl or lower alkoxy, phenyl-lower alkyl, diphenyl-lower alkyl, triphenyl-lower alkyl, lower alkylthiomethyl, phenyl-lower alkylthiomethyl, lower alkanoylamidomethyl, ##STR37## R 6 --S-- or R 7 ; R 3 is hydrogen, hydroxy or lower alkyl; R 5 is lower alkyl, phenyl or phenyl-lower alkyl; R 6 is lower alkyl, phenyl, substituted phenyl, wherein the phenyl substituent is halo, lower alkyl or lower alkoxy, hydroxy-lower alkyl or amino(carboxy)lower alkyl; R 7 is ##STR38## M is O or S; m is 3; n and p each is 0, 1 or 2; and basic salts thereof, said lower alkoxy, lower alkyl and lower alkanoyl groups having up to seven carbon atoms.
Claim 2
Dependent Claim
150 words
A compound of the formula ##STR36## wherein R is hydroxy, NH 2 or lower alkoxy; R 1 and R 4 each is hydrogen, lower alkyl, phenyl or phenyl-lower alkyl; R 2 is hydrogen, lower alkyl, phenyl, substituted phenyl wherein the phenyl substituent is halo, lower alkyl or lower alkoxy, phenyl-lower alkyl, diphenyl-lower alkyl, triphenyl-lower alkyl, lower alkylthiomethyl, phenyl-lower alkylthiomethyl, lower alkanoylamidomethyl, ##STR37## R 6 --S-- or R 7 ; R 3 is hydrogen, hydroxy or lower alkyl; R 5 is lower alkyl, phenyl or phenyl-lower alkyl; R 6 is lower alkyl, phenyl, substituted phenyl, wherein the phenyl substituent is halo, lower alkyl or lower alkoxy, hydroxy-lower alkyl or amino(carboxy)lower alkyl; R 7 is ##STR38## M is O or S; m is 3; n and p each is 0, 1 or 2; and basic salts thereof, said lower alkoxy, lower alkyl and lower alkanoyl groups having up to seven carbon atoms.
Claim 3
Dependent Claim
81 words
A compound as in claim 1 wherein R is hydroxy or lower alkoxy; R 1 is hydrogen or lower alkyl; R 2 is hydrogen, R 5 --CO, R 6 --S--, or R 7 ; R 3 and R 4 each is hydrogen; R 5 is lower alkyl or phenyl; R 6 is lower alkyl; R 7 is ##STR39## wherein R, R 1 and R 4 have the same meaning as above; n is 0, 1 or 2; and p is 0.
Claim 4
Dependent Claim
15 words
A compound as in claim 1 wherein R 3 and R 4 each is hydrogen.
Claim 5
Dependent Claim
11 words
A compound as in claim 1 wherein R 3 is hydrogen.
Claim 6
Dependent Claim
53 words
A compound of the formula ##STR40## wherein R is hydroxy or lower alkoxy; R 1 is hydrogen or lower alkyl; R 2 is hydrogen or lower alkanoyl; n is 0, 1 or 2; and physiologically acceptable salts thereof, said lower alkoxy, lower alkyl and lower alkanoyl groups having up to seven carbon atoms.
Claim 7
Dependent Claim
53 words
A compound of the formula ##STR40## wherein R is hydroxy or lower alkoxy; R 1 is hydrogen or lower alkyl; R 2 is hydrogen or lower alkanoyl; n is 0, 1 or 2; and physiologically acceptable salts thereof, said lower alkoxy, lower alkyl and lower alkanoyl groups having up to seven carbon atoms.
Claim 8
Dependent Claim
10 words
A compound as in claim 5 wherein R is hydroxy.
Claim 9
Dependent Claim
10 words
A compound as in claim 5 wherein n is 1.
Claim 10
Dependent Claim
14 words
A compound as in claim 5 wherein R 2 is hydrogen or lower alkanoyl.
Claim 11
Dependent Claim
11 words
A compound as in claim 5 wherein R 2 is hydrogen.
Claim 12
Dependent Claim
11 words
A compound as in claim 5 wherein R 2 is acetyl.
Claim 13
Dependent Claim
14 words
A compound as in claim 5 wherein R 1 is hydrogen or lower alkyl.
Claim 14
Dependent Claim
13 words
A compound as in claim 5 wherein R 1 is hydrogen or methyl.
Claim 15
Dependent Claim
17 words
A compound as in claim 5 wherein R is hydroxy and R 1 is hydrogen or methyl.
Claim 16
Dependent Claim
29 words
A compound as in claim 5 wherein R is hydroxy, R 1 is hydrogen or methyl, R 2 is hydrogen or acetyl and n is 0, 1 or 2.
Claim 17
Dependent Claim
22 words
A compound as in claim 5 wherein R is hydroxy, R 1 and R 2 each is hydrogen and n is 0.
Claim 18
Dependent Claim
22 words
A compound as in claim 5 wherein R is hydroxy, R 1 is hydrogen, R 2 is acetyl and n is 1.
Claim 19
Dependent Claim
22 words
A compound as in claim 5 wherein R is hydroxy, R 1 and R 2 each is hydrogen and n is 1.
Claim 20
Dependent Claim
22 words
A compound as in claim 5 wherein R is hydroxy, R 1 is methyl, R 2 is hydrogen and n is 1.
Claim 21
Dependent Claim
8 words
The L-form of a compound of claim 5.
Claim 22
Dependent Claim
13 words
The compound of claim 18 in which the piperidine is in the L-form.
Claim 23
Dependent Claim
23 words
A compound as in claim 5 wherein R is hydroxy, R 1 is hydrogen, R 2 is lower alkylthio and n is 2.
Claim 24
Dependent Claim
30 words
A compound as in claim 1 wherein R 2 is ##STR41## each R is hydroxy; each R 1 is hydrogen or lower alkyl; and each n is 0 to 2.
Claim 25
Dependent Claim
21 words
A compound as in claim 22 wherein each R is hydroxy; each R 1 is methyl and each n is 1.
Claim 26
Dependent Claim
11 words
The compound according to claim 1 having the name 1-(3-mercapto-2-methylpropanoyl)-L-pipecolic acid.
Claim 27
Dependent Claim
11 words
The compound according to claim 1 having the name 1,1'-[dithiobis(2-methyl-3-propanoyl)]-bis-L-pipecolic acid.
Claim 28
Dependent Claim
13 words
The compound of claim 17 in which the piperidine is in the L-form.
Claim 29
Dependent Claim
24 words
A composition for reducing blood pressure comprising about 10 to 500 mg. of a compound of claim 1 and a pharmaceutically acceptable vehicle therefor.
Claim 30
Dependent Claim
24 words
A composition for reducing blood pressure comprising about 10 to 500 mg. of a compound of claim 18 and a pharmaceutically acceptable vehicle therefor.
Claim 31
Dependent Claim
24 words
A composition for reducing blood pressure comprising about 10 to 500 mg. of a compound of claim 17 and a pharmaceutically acceptable vehicle therefor.
Claim 32
Dependent Claim
24 words
A composition for reducing blood pressure comprising about 10 to 500 mg. of the compound of claim 24 and a pharmaceutically acceptable vehicle therefor.
Claim 33
Dependent Claim
24 words
A composition for reducing blood pressure comprising about 10 to 500 mg. of the compound of claim 25 and a pharmaceutically acceptable vehicle therefor.
Claim 34
Dependent Claim
44 words
A method for reducing blood pressure in a hypertensive mammal which comprises administering to said mammal an effective hypotensive amount of a composition comprisng a compound having the formula in claim 1, or a physiologically acceptable salt thereof, and a pharmaceutically acceptable vehicle therefor.
Claim 35
Dependent Claim
35 words
A method for reducing blood pressure in a hypertensive mammal which comprises administering to said mammal an effective hypotensive amount of a composition comprising a compound of claim 18 and a pharmaceutically acceptable vehicle therefor.
Claim 36
Dependent Claim
35 words
A method for reducing blood pressure in a hypertensive mammal which comprises administering to said mammal an effective hypotensive amount of a composition comprising a compound of claim 17 and a pharmaceutically acceptable vehicle therefor.
Claim 37
Dependent Claim
35 words
A method for reducing blood pressure in a hypertensive mammal which comprises administering to said mammal an effective hypotensive amount of a composition comprising the compound of claim 24 and a pharmaceutically acceptable vehicle therefor.
Claim 38
Dependent Claim
35 words
A method for reducing blood pressure in a hypertensive mammal which comprises administering to said mammal an effective hypotensive amount of a composition comprising the compound of claim 25 and a pharmaceutically acceptable vehicle therefor.
References Cited (Backward Citations)
US4091024A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-14 | 1982-11-13 | 1983-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-14 | 1986-11-13 | 1987-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-14 | 1990-11-13 | 1991-05-15 | $7700.00 | Window Closed / Lapsed |