Claims
- 1. A compound having the formula ##STR43## wherein R.sub.1 ' is hydrogen or C.sub.1-6 alkyl;
- R.sub.2 ' and R.sub.5 ', independently, are hydrogen or C.sub.1-6 alkyl;
- R.sub.3 ' and R.sub.4 ', independently, are COOR.sub.7 ' or ##STR44## each R.sub.7 ', independently, is C.sub.1-6 alkyl, C.sub.3-7 -cycloalkyl, C.sub.7-10 phenylalkyl or C.sub.3-6 alkoxyalkyl;
- A is C.sub.1-6 alkylene;
- each
- R.sub.8 ' and R.sub.9 ', independently, is C.sub.1-6 alkyl or C.sub.7-10 phenylalkyl; and
- X is oxygen or sulphur,
- or a pharmaceutically acceptable acid addition salt of a basic compound of the above formula.
- 2. A compound of claim 1 wherein R.sub.1 ' is hydrogen.
- 3. A compound according to claim 1 wherein R.sub.1 ' is hydrogen, R.sub.2 ' and R.sub.5 ' are C.sub.1-6 alkyl, R.sub.3 ' and R.sub.4 ' are COOR.sub.7 ' where R.sub.7 ' is C.sub.1-6 alkyl and X is sulphur.
- 4. A compound according to claim 3 where R.sub.2 ' and R.sub.5 ' are methyl and R.sub.7 ' is methyl, ethyl or t-butyl.
- 5. A compound according to claim 4 where R.sub.7 ' is ethyl.
- 6. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester.
- 7. The compound of claim 1 which is 4-(2,1,3-benzothiadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester.
- 8. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxycarbonylpyridine-5-carboxylic acid isobutyl ester.
- 9. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-isopropyloxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 10. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-isopropyloxyethoxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 11. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-ethoxyethoxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 12. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-cyclopentyloxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 13. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-N-benzyl-N-methylamino ethoxycarbonyl-pyridine-5-carboxylic acid ethyl ester, or a pharmaceutically acceptable acid addition salt thereof.
- 14. The compound of claim 1 which is 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxycarbonyl-pyridine-5-carboxylic acid benzyl ester.
- 15. The compound of claim 1 which is 4-(2,1,3-benzothiadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-isobutyloxycarbonyl-pyridine-5-carboxylic acid ethyl ester.
- 16. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-isobutyloxycarbonyl-pyridine-5-carboxylic acid ethyl ester.
- 17. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-ethoxyethoxycarbonyl-pyridine-5-carboxylic acid ethyl ester.
- 18. The compound of claim 1 which is 4-(2,1,3-benzothiadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-ethoxyethoxycarbonyl-pyridine-5-carboxylic acid ethyl ester.
- 19. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxyethoxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 20. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxyethoxycarbonyl-pyridine-5-carboxylic acid isopropyl ester.
- 21. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxycarbonyl-pyridine-5-carboxylic acid ethyl ester.
- 22. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-1-propyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester.
- 23. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-N-benzyl-N-methylamino ethoxycarbonyl-pyridine-5-carboxylic acid methyl ester, or a pharmaceutically acceptable acid addition salt thereof.
- 24. A pharmaceutical composition useful in treating coronary insufficiency comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 25. A pharmaceutical composition useful in treating intermittent claudication comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 26. A pharmaceutical composition useful in treating cerebrovascular accidents comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 27. A pharmaceutical composition useful in treating muscular spasms comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 28. A pharmaceutical composition useful in treating hypertension comprising a pharmaceutically acceptable carrier or diluent and a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 29. The compound of claim 1 which is 4-(2,1,3-benzoxadiazole-4-yl)-2,6-dimethyl-1,4-dihydro-3-phenethyloxycarbonyl-pyridine-5-carboxylic acid methyl ester.
- 30. A method of treating coronary insufficiency comprising administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 31. A method of treating intermittent claudication comprising administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 32. A method of treating cerebrovascular accidents comprising administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 33. A method of treating muscular spasms comprising administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
- 34. A method of treating hypertension comprising administering to an animal in need of such treatment a therapeutically effective amount of a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof.
Priority Claims (10)
Number |
Date |
Country |
Kind |
7520/77 |
Jun 1977 |
CHX |
|
2865/78 |
Mar 1978 |
CHX |
|
5627/79 |
Jun 1978 |
CHX |
|
12835/78 |
Dec 1978 |
CHX |
|
12888/78 |
Dec 1978 |
CHX |
|
12890/78 |
Dec 1978 |
CHX |
|
3472/79 |
Apr 1979 |
CHX |
|
3477/79 |
Apr 1979 |
CHX |
|
40624/79 |
Nov 1979 |
GBX |
|
294945 |
Dec 1979 |
DEX |
|
Parent Case Info
This is a continuation of application Ser. No. 173,305 filed July 29, 1980 which in turn is a continuation-in-part of Ser. No. 101,591 filed Dec. 10, 1979, which in turn is a continuation-in-part of Ser. No. 915,858, filed June 15, 1978, all now abandoned.
US Referenced Citations (7)
Foreign Referenced Citations (4)
Number |
Date |
Country |
0750139 |
Nov 1970 |
BEX |
2210667 |
Sep 1973 |
DEX |
2210672 |
Sep 1973 |
DEX |
1425059 |
Feb 1976 |
GBX |
Continuations (1)
|
Number |
Date |
Country |
Parent |
173305 |
Jul 1980 |
|
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
101591 |
Dec 1979 |
|
Parent |
915858 |
Jun 1978 |
|