Claims
- 1. A compound which, in its free-base form, is a pharmacologically-active and physiologically-acceptable 3-amino-sydnonimine of the formula ##STR11## wherein R.sup.1 is --H or halo;
- R.sup.2 is --H, --NO, --COR.sup.3 or SO.sub.2 R.sup.4 ;
- R.sup.3 is --H; optionally-substituted aliphatic hydrocarbyl having from 1 to 6 carbon atoms and any substituent of which is alkoxy with from 1 to 6 carbon atoms or carbocyclic aryloxy with from 6 to 12 carbon atoms; cycloaliphatic hydrocarbyl having from 5 to 8 ring carbon atoms; optionally-substituted carbocyclic aryl with from 6 to 12 ring carbon atoms and 0, 1, 2 or 3 substituents, any of which is, independently, halo, alkyl with from 1 to 4 carbon atoms or alkoxy with from 1 to 4 carbon atoms; araliphatic hydrocarbyl with from 7 to 13 carbon atoms; alkoxy with from 1 to 6 carbon atoms; carbocyclic aryloxy with from 6 to 12 ring carbon atoms; heteroaryl with 5 or 6 ring members, at least 2 of which are carbon atoms, at most one of which is a sulfur atom, at most one of which is an oxygen atom and at most three of which are nitrogen atoms, and wherein any ring member is a carbon atom, a sulfur atom, an oxygen atom or a nitrogen atom; or alkoxycarbonyl with from 2 to 7 carbon atoms;
- A is >N--SO.sub.2 R.sup.5 ;
- and
- each of
- R.sup.4 and R.sup.5 is, independently, aliphatic hydrocarbyl with from 1 to 6 carbon atoms; optionally-substituted carbocyclic aryl with from 6 to 12 ring carbon atoms, any substituent of which is methyl or chloro; or dialkylamino, each alkyl of which has, independently, from 1 to 4 carbon atoms.
- 2. A compound according to claim 1 wherein R.sup.3 is --H; optionally-substituted alkyl having from 1 to 6 carbon atoms and any substituent of which is alkoxy with from 1 to 6 carbon atoms or phenoxy; cyclohexyl; optionally-substituted phenyl with 0, 1, 2 or 3 substituents, any of which is, independently, chloro, alkyl with from 1 to 4 carbon atoms or alkoxy with from 1 to 4 carbon atoms; benzyl; styryl; alkoxy with from 1 to 6 carbon atoms; phenoxy; pyridyl; or alkoxycarbonyl with from 2 to 7 carbon atoms; and each of R.sup.4 and R.sup.5 is, independently, alkyl with from 1 to 6 carbon atoms; optionally-substituted phenyl, any substituent of which is methyl or chloro; or dialkylamino, each alkyl of which has, independently, from 1 to 4 carbon atoms.
- 3. A free base according to claim 2.
- 4. A physiologically-acceptable acid-addition salt according to claim 2.
- 5. A compound according to claim 2 wherein R.sup.1 is --H.
- 6. A compound according to claim 5 wherein R.sup.2 is --H.
- 7. A compound according to claim 2 wherein R.sup.2 is --COR.sup.3 and R.sup.3 is alkyl with from 1 to 4 carbon atoms.
- 8. A compound according to claim 7 wherein R.sup.1 is --H.
- 9. A compound according to claim 2 wherein R.sup.2 is --H.
- 10. A compound according to claim 2 wherein R.sup.2 is --CO--pyridyl.
- 11. A compound according to claim 2 or 5 wherein R.sup.2 is --CO--OCH.sub.3 or --CO--O--CH.sub.2 CH.sub.3.
- 12. A compound according to claim 2 or 5 wherein R.sup.2 is --COR.sup.3, and R.sup.3 is alkoxycarbonyl with a total of 2 or 3 carbon atoms.
- 13. A compound according to claim 2 wherein R.sup.2 is --COR.sup.3.
- 14. A compound according to claim 13 wherein R.sup.3 is cycloaliphatic hydrocarbyl.
- 15. A compound according to claim 13 wherein R.sup.3 is optionally-substituted carbocyclic aryl.
- 16. A compound according to claim 13 wherein R.sup.3 is alkoxycarbonyl.
- 17. A compound according to claim 2, wherein R.sup.1 is --H and R.sup.5 is alkyl.
- 18. A compound according to claim 2 wherein R.sup.1 is --H and R.sup.5 is dialkylamino.
- 19. A pharmaceutical composition useful for reducing blood pressure in unit-dosage form having from 0.1 to 50 milligrams of a pharmacologically-acceptable compound according to claim 2 in combination with carrier therefor.
- 20. A pharmaceutical composition for reducing blood pressure and having, per unit dose, an effective amount of a pharmacologically-acceptable compound according to claim 2 in combination with suitable carrier.
- 21. The compound according to claim 2 which is 3-(4-dimethylaminosulfonyl-piperazin-1-yl)sydnonimine.
- 22. The hydrochloride of the compound of claim 21.
- 23. A pharmaceutical composition for reducing cardiac work (in the sense of an anti-anginal action) without provoking reflex tachycardia and having, per unit dose, an effective amount of a pharmacologically-acceptable compound according to claim 2 in combination with a suitable carrier.
- 24. A compound according to claim 2 which is 3-(4-methanesulfonyl-piperazin-1-yl)sydnonimine or a physiologically-acceptable acid-addition salt thereof.
- 25. A compound according to claim 2 which is N.sup.6 -ethoxycarbonyl-3-(4-methanesulfonyl-piperazin-1-yl)sydnonimine or a physiologically-acceptable acid-addition salt thereof.
- 26. A compound according to claim 2 which is N.sup.6 -benzoyl-3-(4-methanesulfonyl-piperazin-1-yl)sydnonimine or a physiologically-acceptable acid-addition salt thereof.
- 27. A compound according to claim 2 which is N.sup.6 -propionyl-3-(4-dimethylaminosulfonyl-piperazin-1-yl)sydnonimine or a physiologically-acceptable acid-addition salt thereof.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2930736 |
Jul 1979 |
DEX |
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CROSS-REFERENCE TO RELATED APPLICATION
The present application is a division of Application Ser. No. 166,951, filed July 8, 1980 now U.S. Pat. No. 4,305,939.
US Referenced Citations (5)
Divisions (1)
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Number |
Date |
Country |
Parent |
166951 |
Jul 1980 |
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