Claims for Patent: 4,466,972

Summary for Patent: 4,466,972

Title:	Benzoxadiazoles and benzothiadiazoles, their preparation and pharmaceutical compositions containing them
Abstract:	Compounds of formula I, ##STR1## wherein X is oxygen or sulphur, and R.sub.1 -R.sub.6 are various substituents. The compounds are useful for treating coronary insufficiency, intermittent claudication, cerebrovascular insults, spasms in muscles and hypertension.
Inventor(s):	Neumann; Peter (Berne, CH)
Assignee:	Sandoz Ltd. (Basel, CH)
Application Number:	06/359,751
Patent 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-dicarbo xylic 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-dicar boxylic 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-methoxycarbonylpyr idine-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-isopropyloxycarbon yl-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-isopropyloxyethoxy carbonyl-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-ethoxyethoxycarbon yl-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-cyclopentyloxycarb onyl-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-methyla mino 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-py ridine-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-isobutyloxycarb onyl-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-isobutyloxycarbon yl-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-ethoxyethoxycarbo nyl-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-ethoxyethoxycar bonyl-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-methoxyethoxycarb onyl-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-methoxyethoxycarb onyl-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-p yridine-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-methyl amino 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-phenethyloxycarbo nyl-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.