Claims
- 1. A proline derivative represented by the formula ##STR127## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.6 alkyl;
- R.sup.2 and R.sup.4 are the same or different and each represents hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.3 is C.sub.1 -C.sub.6 alkyl; and
- Y is C.sub.2 alkylene;
- or a pharmaceutically acceptable salt thereof.
- 2. A proline derivative as defined in claim 1 wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl.
- 3. A proline derivative as defined in claim 1 wherein R.sup.1 is C.sub.3 -C.sub.8 cycloalkyl.
- 4. A proline derivative as defined in claim 1 wherein R.sup.1 is C.sub.4 -C.sub.6 cycloalkyl R.sup.3 is methyl.
- 5. A proline derivative as defined in claim 1 which is selected from the group consisting of:
- N-[(R)-1-ethoxycarbonyl-2-(2-butylthioethylthio)ethyl]-alanyl-(S)-proline methyl ester (.beta.-isomer),
- N-[(R)-1-ethoxycarbonyl-2-(2-cyclohexylthioethylthio)ethyl]-alanyl-(S)-proline methyl ester (.beta.-isomer),
- N-[(R)-1-ethoxycarbonyl-2-(2-cyclopentylthioethylthio)ethyl]-alanyl-(S)-proline methyl ester (.beta.-isomer),
- N-[(R)-1-ethoxycarbonyl-2-(2-butylthioethylthio)ethyl]-alanyl-(S)-proline (.beta.-isomer),
- N-[(R)-1-ethoxycarbonyl-2-(2-cyclohexylthio)ethylthio)ethyl]-alanyl-(S)proline (.beta.-isomer),
- N-[(R)-1-ethoxycarbonyl-2-(2-cyclopentylthioethylthio)ethyl]-alanyl-(S)-proline (.beta.-isomer), and
- N-[(R)-1-ethoxycarbonyl-2-pentyldithioethyl]-alanyl-(S)-proline methyl ester (.beta.-isomer).
- 6. A proline derivative as defined in claim 5 which is N-[(R)-1-ethoxycarbonyl-2-(2-cyclopentyl-thioethylthio)ethyl]-alanyl-(S)-proline (.beta.-isomer).
- 7. A pharmaceutical composition for inhibiting angiotensin converting enzyme comprising an effective amount of at least one of the proline derivative and pharmaceutically acceptable salt thereof as defined in claim 1 in combination with a pharmaceutically acceptable carrier.
- 8. A pharmaceutical composition as defined in claim 7 wherein R.sup.1 is C.sub.3 -C.sub.8 cycloalkyl R.sup.3 is C.sub.1 -C.sub.6 alkyl, and n is 1.
- 9. A pharmaceutical composition as defined in claim 7 wherein R.sup.1 is C.sub.4 -C.sub.6 cycloalkyl R.sup.3 is methyl.
- 10. A pharmaceutical composition as defined in claim 7 which is N-[(R)-1-ethoxycarbonyl-2-(2-cyclopentylthioethylthio)ethyl]-alanyl-(S)-proline (.beta.-isomer).
- 11. A method for inhibiting angiotensin converting enzyme comprising administering to a patient of an effective amount of at least one of the proline derivative and pharmaceutically acceptable salt thereof as defined in claim 1 in an amount effective for inhibiting the angiotensin converting enzyme.
- 12. A method as defined in claim 11 wherein R.sup.1 is C.sub.3 -C.sub.8 cycloalkyl.
- 13. A method as defined in claim 11 wherein R.sup.1 is C.sub.4 -C.sub.6 cycloalkyl and R.sup.3 is methyl.
- 14. A method as defined in claim 11 which is N-[(R)-1-ethoxycarbonyl-2-(2-cyclopentyl-thioethylthio)ethyl]-alanyl-(S)-proline (.beta.-isomer).
Priority Claims (3)
Number |
Date |
Country |
Kind |
61-8634 |
Jan 1986 |
JPX |
|
61-85797 |
Apr 1986 |
JPX |
|
61-293782 |
Dec 1986 |
JPX |
|
Parent Case Info
This application is a continuation of application Ser. No. 001,779 filed Jan. 9, 1987 and now abandoned.
US Referenced Citations (9)
Foreign Referenced Citations (4)
Number |
Date |
Country |
0012401 |
Jun 1980 |
EPX |
0050800 |
May 1982 |
EPX |
55-81845 |
Jun 1980 |
JPX |
2045771A |
Nov 1980 |
GBX |
Continuations (1)
|
Number |
Date |
Country |
Parent |
1779 |
Jan 1987 |
|