Sulfooxy-pyrimidinium, -pyridinium, and -triazinium hydroxide inner salts
AssigneeThe Upjohn Company
InventorJohn M. McCall
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Abstract
The present invention provides novel substituted sulfooxy-pyrimidinium, -pyridinium, and -triazinium hydroxide inner salts. These compounds are useful for the treatment of hypertension and peripheral vascular diseases. They are formed by reacting the corresponding aminopyrimidine, aminotriazine, and aminopyridine N-oxides with a latent sulfate source such as pyridinium-sulfur trioxide complex, triethylamine-sulfur trioxide complex, chlorosulfonic acid or chlorosulfuryl chloride.
Claims6
A compound of the formula II
- wherein
- (a) R.sub.1 is selected from the group consisting of alkyl of from one to 8 carbon atoms, or NHR.sub.4 wherein R.sub.4 is hydrogen or alkyl of from one to 4 carbon atoms;
- (b) R.sub.2 and R.sub.3 are the same or different and are hydrogen, alkyl of from one to 8 carbon atoms, with the proviso that if R.sub.2 is hydrogen, R.sub.3 is not hydrogen or methyl, and vice-versa, alkenyl of from 3 to 8 carbon atoms (excluding unsaturation at the carbon directly bonded to the nitrogen), phenylalkyl wherein the alkyl portion of the moiety is from one to 3 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, or R.sub.2 and R.sub.3 taken together with nitrogen form a heterocyclic moiety selected from the following:
- 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, hexahydro-1H-azepin-1-yl, hexahydro-1(2H)-azocinyl, 4-alkylpiperazinyl (wherein the alkyl portion of the moiety is of one to 3 carbon atoms), 4-morpholinyl, 4-thiomorpholinyl, 3,6-dihydro-1(2H)-pyridinyl, 3-pyrrolin-1-yl, 2,3,4,7-tetrahydro-1H-azepine-1-yl, and 3,4,7,8-tetrahydro-1(2H)-azocinyl,
- said heterocyclic moieties optionally being substituted by one to 3 alkyl groups of from one to 3 carbon atoms, and
- (c) W and Y are the same or different and are nitrogen or carbon;
- or the
A compound of claim 4 wherein R.sub.1 is amino, R.sub.2 and R.sub.3 are 2-propenyl and the compound is 2,6-diamino-4-(di-2-propenylamino)-1-(sulfooxy)-1,3,5-triazinium hydroxide, inner salt.
Dependencies are inferred from the claim text.