US4248883A
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1-(3-Mercapto-2-methylpropanoyl)prolyl amino acid derivatives and salts thereof, processes for their preparation, and pharmaceutical compositions containing such compounds
Assignee: Sumitomo Pharma Co Ltd
•
Filing: 1979-06-29
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Granted: 1981-02-03
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Expires: 1999-06-29
Abstract
Abstract 1-(3-Mercapto-2-methylpropanoyl)prolyl amino acid derivatives of the formula <IMAGE> wherein R represents a hydrogen atom, a lower alkyl group, a phenyl-lower alkyl group or a substituted phenyl-lower alkyl group, R1 represents a hydrogen atom, R4CO-, R5S-, or <IMAGE> R2 represents a hydrogen atom or a lower alkyl group, R3 represents a hydrogen atom, a phenyl group, a lower alkyl group, or a substituted lower alkyl group, or R2 and R3 form a heterocyclic ring together with the nitrogen and carbon atoms to which they are respectively bonded; salts of these compounds; compositions comprising these compounds or salts; and processes for preparing these compounds or salts. These compounds and salts have excellent antihypertensive activity.
Inventors
- 👤 Tadahiro Sawayama
- 👤 Hiroaki Kinugasa
- 👤 Haruki Nishimura
- 👤 Kunihiko Takeyama
- 👤 Kanoo Hosoki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:23
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06139; C07K5/06165; A; A61; A61P; A61P43/00; C07C; C07C327/00; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
91 words
A compound of the formula ##STR17## wherein R represents hydrogen, lower alkyl, phenyl-lower alkyl or substituted phenyl-lower alkyl, R 1 represents R 4 CO--, R 2 represents hydrogen or lower alkyl, R 3 represents hydrogen, phenyl, lower alkyl, or substituted lower alkyl in which the substituent is hydroxy, phenyl-lower alkoxy, phenyl or hydroxyphenyl, R 4 represents lower alkyl, phenyl, substituted phenyl, phenyl-lower alkyl or substituted phenyl-lower alkyl, the substituent in the substituted phenyl group in the foregoing definition being halogen, lower alkyl or lower alkoxy; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
91 words
A compound of the formula ##STR17## wherein R represents hydrogen, lower alkyl, phenyl-lower alkyl or substituted phenyl-lower alkyl, R 1 represents R 4 CO--, R 2 represents hydrogen or lower alkyl, R 3 represents hydrogen, phenyl, lower alkyl, or substituted lower alkyl in which the substituent is hydroxy, phenyl-lower alkoxy, phenyl or hydroxyphenyl, R 4 represents lower alkyl, phenyl, substituted phenyl, phenyl-lower alkyl or substituted phenyl-lower alkyl, the substituent in the substituted phenyl group in the foregoing definition being halogen, lower alkyl or lower alkoxy; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
31 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R 3 represents hydrogen, lower alkyl or substituted lower alkyl in which the substituent is phenyl or hydroxyphenyl.
Claim 4
Dependent Claim
17 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R 2 represents hydrogen.
Claim 5
Dependent Claim
30 words
A compound or a pharmaceutically acceptable salt thereof according to claim 3 wherein R 3 represents lower alkyl, or substituted lower alkyl in which the substituent is phenyl or hydroxyphenyl.
Claim 6
Dependent Claim
21 words
A compound or a pharmaceutically acceptable salt thereof according to claim 3 wherein R 3 represents a benzyl or p-hydroxybenzyl group.
Claim 7
Dependent Claim
17 words
A compound or a pharmaceutically acceptable salt thereof according to claim 3 wherein R 3 represents benzyl.
Claim 8
Dependent Claim
19 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R represents hydrogen or lower alkyl.
Claim 9
Dependent Claim
22 words
A compound or a pharmaceutically acceptable salt thereof according to claim 7 wherein R 2 represents hydrogen and R 3 represents benzyl.
Claim 10
Dependent Claim
25 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R 1 represents alkanoyl containing 2 to 7 carbon atoms or benzoyl.
Claim 11
Dependent Claim
52 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R represents hydrogen or lower alkyl, R 1 represents lower alkanoyl or benzoyl, R 2 represents hydrogen or lower alkyl, and R 3 represents hydrogen, lower alkyl, or substituted lower alkyl in which the substituent is phenyl or hydroxyphenyl.
Claim 12
Dependent Claim
35 words
A compound or a pharmaceutically acceptable salt thereof according to claim 10 wherein R 2 represents hydrogen, and R 3 represents lower alkyl, or substituted lower alkyl in which the substituent is phenyl or hydroxyphenyl.
Claim 13
Dependent Claim
21 words
A compound or a pharmaceutically acceptable salt thereof according to claim 11 wherein R 3 represents a benzyl or p-hydroxybenzyl group.
Claim 14
Dependent Claim
17 words
A compound or a pharmaceutically acceptable salt thereof according to claim 11 wherein R 3 represents benzyl.
Claim 15
Dependent Claim
47 words
A compound or a pharmaceutically acceptable salt thereof according to claim 1 wherein R represents hydrogen or alkyl containing 1 or 2 carbon atoms, R 1 represents alkanoyl containing 2 to 7 carbon atoms or benzoyl, R 2 represents hydrogen and R 3 represents benzyl or p-hydroxybenzyl.
Claim 16
Dependent Claim
45 words
A compound of the formula ##STR18## wherein R represents hydrogen or alkyl containing 1 or 2 carbon atoms, R 1 represents alkanoyl containing 2 to 7 carbon atoms or benzoyl, R 2 represents hydrogen and R 3 represents benzyl, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
45 words
A compound of the formula ##STR18## wherein R represents hydrogen or alkyl containing 1 or 2 carbon atoms, R 1 represents alkanoyl containing 2 to 7 carbon atoms or benzoyl, R 2 represents hydrogen and R 3 represents benzyl, or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
28 words
A compound or a pharmaceutically acceptable salt thereof according to claim 15 wherein R and R 2 represent hydrogen, R 1 represents acetyl, and R 3 represents benzyl.
Claim 19
Dependent Claim
28 words
A compound or a pharmaceutically acceptable salt thereof according to claim 15 wherein R and R 2 represent hydrogen, R 1 represents propanoyl, and R 3 represents benzyl.
Claim 20
Dependent Claim
28 words
A compound or a pharmaceutically acceptable salt thereof according to claim 15 wherein R and R 2 represent hydrogen, R 1 represents 2,2-dimethylpropanoyl, and R 3 represents benzyl.
Claim 21
Dependent Claim
28 words
A compound or a pharmaceutically acceptable salt thereof according to claim 15 wherein R and R 2 represent hydrogen, R 1 represents 2-methylpropanoyl, and R 3 represents benzyl.
Claim 22
Dependent Claim
28 words
A compound or a pharmaceutically acceptable salt thereof according to claim 15 wherein R and R 2 represent hydrogen, R 1 represents benzoyl, and R 3 represents benzyl.
Claim 23
Dependent Claim
36 words
A compound or a pharmaceutically acceptable salt thereof according to any one of claims 1, 10, 11, 12, 13, 14 and 15 wherein the configurations of the proline moiety and R 3 are in the L-form.
Claim 24
Dependent Claim
30 words
A compound or a pharmaceutically acceptable salt thereof according to claim 21 wherein the configuration of the methyl group at the 2-position of the group ##STR19## is in the D-form.
Claim 25
Dependent Claim
34 words
A compound or a pharmaceutically acceptable salt thereof according to any one of claims 16, 17, 18, 19 and 20 wherein the configurations of the proline moiety and R 3 are in the L-form.
Claim 26
Dependent Claim
1 words
1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 27
Dependent Claim
1 words
1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 28
Dependent Claim
1 words
1-(D-3-Propanoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 29
Dependent Claim
1 words
1-(D-3-Propanoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 30
Dependent Claim
1 words
1-[D-3-(2,2-Dimethylpropanoyl)thio-2-methylpropanoyl]-L-prolyl-L-phenylalanine.
Claim 31
Dependent Claim
1 words
1-[D-3-(2,2-Dimethylpropanoyl)thio-2-methylpropanoyl]-L-prolyl-L-phenylalanine.
Claim 32
Dependent Claim
1 words
1-[D-3-(2-Methylpropanoyl)thio-2-methylpropanoyl]-L-prolyl-L-phenylalanine.
Claim 33
Dependent Claim
1 words
1-[D-3-(2-Methylpropanoyl)thio-2-methylpropanoyl]-L-prolyl-L-phenylalanine.
Claim 34
Dependent Claim
1 words
1-(D-3-Benzoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 35
Dependent Claim
1 words
1-(D-3-Benzoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine.
Claim 36
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 1.
Claim 37
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 1, and a pharmaceutically acceptable carrier.
Claim 38
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 15.
Claim 39
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 16.
Claim 40
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 17.
Claim 41
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 24.
Claim 42
Dependent Claim
27 words
A method of treating hypertension in mammals which comprises administering an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 25.
Claim 43
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 15, and a pharmaceutically acceptable carrier.
Claim 44
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 16, and a pharmaceutically acceptable carrier.
Claim 45
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 17, and a pharmaceutically acceptable carrier.
Claim 46
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 24, and a pharmaceutically acceptable carrier.
Claim 47
Dependent Claim
26 words
A pharmaceutical composition comprising an antihypertensive effective amount of a compound or a pharmaceutically acceptable salt thereof according to claim 25, and a pharmaceutically acceptable carrier.
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) | 1984-02-03 | 1984-08-04 | 1985-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-03 | 1988-08-04 | 1989-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-03 | 1992-08-04 | 1993-02-03 | $7700.00 | Window Closed / Lapsed |