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US4226775A
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Substituted thio-substituted benzyl-propionyl-L-prolines
Assignee: Wyeth Holdings LLC
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Filing: 1979-06-01
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Granted: 1980-10-07
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Expires: 1999-06-01
Abstract
Abstract This disclosure describes novel substituted ω-aroyl(propionyl or butyryl)-L-prolines and the esters and cationic salts thereof which are useful as hypotensive agents in mammals.
Inventors
- 👤 Francis J. McEvoy
- 👤 Jay D. Albright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:01
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/46; C07C; C07C327/00; C07C59/00; C07C59/40; C07C59/76; C07C59/84; C07C59/88; C07D207/02; C07D207/04; C07D207/10; C07D207/16
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
225 words
A compound selected from the group consisting of those of the formulae: ##STR22## wherein n is zero or one; R 1 is hydrogen or alkyl having up to 3 carbon atoms; R 2 is hydrogen, phenyl or alkyl having up to 3 carbon atoms; R 3 is mercapto, formylthio, benzoylthio, alkanolythio having from 2 to 4 carbon atoms or moieties of the formulae: ##STR23## wherein R 9 is phenyl; R 4 is hydrogen, phenyl or alkyl having up to 4 carbon atoms; R 5 is hydrogen or alkyl having up to 4 carbon atoms; and ARYL is selected from the group consisting of 1-naphthyl, 2-naphthyl, 4-chloro-1-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 4-methoxy-1-naphthyl, 5-acenaphthyl, 4-biphenylyl, 5-indanyl, 4-indanyl and moieties of the formula: ##STR24## wherein R 6 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl, cyano, amnio, phenoxy, halophenoxy, phenylthio, halophenylthio, p-cyclohexylphenoxy, alkyl having up to 4 carbon atoms, alkoxy having up to 4 carbon atoms, alkylamino having up to 4 carbon atoms, alkanoylamino having from 2 to 4 carbon atoms and alkoxycarbonyl having from 2 to 4 carbon atoms, R 7 is selected from the group consisting of chloro, fluoro, bromo, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms, and m is zero, one or two; and the pharmacologically acceptable cationic salts thereof when R 5 is hydrogen.
Claim 2
Dependent Claim
225 words
A compound selected from the group consisting of those of the formulae: ##STR22## wherein n is zero or one; R 1 is hydrogen or alkyl having up to 3 carbon atoms; R 2 is hydrogen, phenyl or alkyl having up to 3 carbon atoms; R 3 is mercapto, formylthio, benzoylthio, alkanolythio having from 2 to 4 carbon atoms or moieties of the formulae: ##STR23## wherein R 9 is phenyl; R 4 is hydrogen, phenyl or alkyl having up to 4 carbon atoms; R 5 is hydrogen or alkyl having up to 4 carbon atoms; and ARYL is selected from the group consisting of 1-naphthyl, 2-naphthyl, 4-chloro-1-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 4-methoxy-1-naphthyl, 5-acenaphthyl, 4-biphenylyl, 5-indanyl, 4-indanyl and moieties of the formula: ##STR24## wherein R 6 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl, cyano, amnio, phenoxy, halophenoxy, phenylthio, halophenylthio, p-cyclohexylphenoxy, alkyl having up to 4 carbon atoms, alkoxy having up to 4 carbon atoms, alkylamino having up to 4 carbon atoms, alkanoylamino having from 2 to 4 carbon atoms and alkoxycarbonyl having from 2 to 4 carbon atoms, R 7 is selected from the group consisting of chloro, fluoro, bromo, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms, and m is zero, one or two; and the pharmacologically acceptable cationic salts thereof when R 5 is hydrogen.
Claim 3
Dependent Claim
30 words
The compound according to claim 1, formula (I) thereof, wherein R 3 is acetylthio, ARYL is 1-naphthyl, and R 1 , R 2 and R 5 are all hydrogen; 1[2-acctylthio-3-(1-naphthoyl)propionyl]-L-proline.
Claim 4
Dependent Claim
30 words
The compound according to claim 1, formula (I) thereof, wherein R 3 is benzoylthio, ARYL is 2-naphthyl, and R 1 , R 2 and R 5 are all hydrogen; 1-[2-benzoylthio-3-(2-naphthoyl)propionyl]-L-proline.
Claim 5
Dependent Claim
30 words
The compound according to claim 1, formula (I) thereof, wherein R 3 is mercapto, ARYL is phenyl, and R 1 , R 2 and R 5 are all hydrogen; 1-[2-mercapto-3-(benzoyl)pripionyl]-L-proline.
Claim 6
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-biphenylyl, R 3 is acetylthio, and R 4 and R 5 are both hydrogen; 1-[3-acetylthio-3-(4-biphenylylcarbonyl)propionyl]-L-proline.
Claim 7
Dependent Claim
27 words
The compound according to claim 1, formula (II) thereof, wherein R 3 is acetylthio, ARYL is 4-chlorophenyl, R 1 is hydrogen, and R 2 is methyl; [S(R*,S*)]-1-[3-acetylthio-4-(4-chlorobenzoyl)-2-methylbutyryl]-L-proline.
Claim 8
Dependent Claim
30 words
The compound according to clai 1, formula (III) thereof, wherein n is zero, R 3 is acetylthio, ARYL is 4-chlorophenyl, R 4 is methyl and R 5 is hydrogen; 1-[3-acetylthio-3-(4-chlorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 9
Dependent Claim
30 words
The compound according to clai 1, formula (III) thereof, wherein n is zero, R 3 is acetylthio, ARYL is 4-chlorophenyl, R 4 is methyl and R 5 is hydrogen; 1-[3-acetylthio-3-(4-chlorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 10
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, R 3 is acetylthio, ARYL is 3-fluorophenyl, R 4 is methyl and R 5 is hydrogen; 1-[3-acetylthio-3-(3-fluorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 11
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-chloro-1-naphthyl, R 3 is acetylthio, and R 4 and R 5 are both hydrogen; 1-[3-acetylthio-3-(4-chloro-1-naphthoyl)propionyl]-L-proline.
Claim 12
Dependent Claim
34 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, m is zero, R 6 is 4-(4-chlorophenoxy), R 3 is acetylthio, and R 4 and R 5 are both hydrogen; 1-{3-acetylthio-3-[4-(4-chlorophenoxy)benzoyl]propionyl}-L-proline.
Claim 13
Dependent Claim
38 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, m is one, R 6 and R 7 are both chloro, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; 1-[3-acetylthio-3-(3,4-dichlorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 14
Dependent Claim
38 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, m is one, R 6 is 4-methoxy, R 7 is 3-fluoro, R 3 is benzoylthio, and R 4 and R 5 are both hydrogen; 1-[3-benzoylthio-3-(3-fluoro-4-methoxybenzoyl)propionyl]-L-proline.
Claim 15
Dependent Claim
38 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, m is two, R 6 is methoxy, R 7 is methoxy, R 3 is acetylthio, and R 4 and R 5 are both hydrogen; 1-[3-acetylthio-3-(3,4,5-trimethoxybenzoyl)propionyl]-L-proline.
Claim 16
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, R 3 is acetylthio, ARYL is 3-trifluoromethylphenyl, R 4 is methyl, and R 5 is hydrogen; 1-[3-acetylthio-3-(3-trifluoromethylbenzoyl)-2-methylpropionyl]-L-proline.
Claim 17
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is phenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,S*]-1-[3-(acetylthio)-3-(benzoyl)-2-methylpropionyl]-L-proline.
Claim 18
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 3-fluorophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-3-(3-fluorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 19
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-bromophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-3-(4-bromobenzoyl)-2-methylpropionyl]-L-proline.
Claim 20
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-bromophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,R*)]-1-[3-acetylthio-3-(4-bromobenzoyl)-2-methylpropionyl]-L-proline.
Claim 21
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-chlorophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-3-(4-chlorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 22
Dependent Claim
30 words
The compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 4-chlorophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,R*)]-1-[3-acetylthio-3-(4-chlorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 23
Dependent Claim
30 words
A compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 2-naphthyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-3-(2-naphthoyl)-2-methylpropionyl]-L-proline.
Claim 24
Dependent Claim
30 words
A compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is phenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,R*)]-1-[3-acetylthio-3-(benzoyl)-2-methylpropionyl]-L-proline.
Claim 25
Dependent Claim
30 words
A compound according to claim 1, formula (III) thereof, wherein n is zero, ARYL is 3-fluorophenyl, R 3 is acetylthio, R 4 is methyl and R 5 is hydrogen; [S-(R*,R*)]-1-[3-acetylthio-3-(3-fluorobenzoyl)-2-methylpropionyl]-L-proline.
Claim 26
Dependent Claim
31 words
A compound according to claim 1, formula (II) thereof, wherein ARYL is phenyl, R 1 is hydrogen, R 2 is methyl, R 3 is acetylthio and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-4-(benzoyl)-2-methylbutyryl]-L-proline.
Claim 27
Dependent Claim
31 words
A compound according to claim 1, formula (II) thereof, wherein ARYL is 3-fluorophenyl, R 1 is hydrogen, R 2 is methyl, R 3 is acetylthio and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-4-(3-fluorobenzoyl)-2-methylbutyryl]-L-proline.
Claim 28
Dependent Claim
31 words
A compound according to claim 1, formula (II) thereof, wherein ARYL is 2-naphthyl, R 1 is hydrogen, R 2 is methyl, R 3 is acetylthio and R 5 is hydrogen; [S-(R*,S*)]-1-[3-acetylthio-4-(2-naphthoyl)-2-methylbutyryl]-L-proline.
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) | 1983-10-07 | 1984-04-07 | 1984-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-07 | 1988-04-07 | 1988-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-07 | 1992-04-07 | 1992-10-07 | $7700.00 | Window Closed / Lapsed |