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|Title:||3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same|
|Abstract:||This invention relates to new derivatives of pyridine having anti-inflammatory and diuretic properties. The new derivatives of pyridine may be represented by the following general formula: ##STR1## in which X represents an amino, C.sub.1 -C.sub.4 -alkylamino, oxy or thio group, R.sub.1 represents a group of the formula R.sub.3 NHCA (II), wherein A represents oxygen or sulfur, and R.sub.3 represents a C.sub.1 -C.sub.4 -alkyl, alkenyl, cycloalkyl, phenyl (which may be substituted) or R.sub.4 CO (III) group, R.sub.4 representing a phenyl group (which may be substituted), R.sub.2 represents hydrogen or a C.sub.1 -C.sub.4 alkyl group and Z represents a C.sub.1 -C.sub.4 -alkyl, methylfuryl, pyridyl or phenyl group (which may be substituted). This invention relates also to the N-oxides of the compounds of formula I, as well as to the acid and base addition salts of said compounds.|
|Inventor(s):||Delarge; Jacques E. (Dolembreux, BE), Lapiere; Charles L. (Tongeren, BE), Georges; Andre H. (Ottignies, BE)|
|Assignee:||A. Christiaens Societe Anonyme (Brussels, BE)|
1. A compound of the following formula: ##STR10## in which X represents an amino or C.sub.1 -C.sub.4 -alkylamino group;
R.sub.1 represents a group of the formula:
where A represents oxygen or sulfur and R.sub.3 represents a C.sub.1 -C.sub.4 -alkyl, allyl, cyclohexyl, unsubstituted phenyl group or a phenyl group substituted by chloro, or a group of the formula R.sub.4 CO(III), wherein R.sub.4 represents an unsubstituted phenyl group or a phenyl group substituted by chloro; R.sub.2 represents hydrogen or a C.sub.1 -C.sub.4 -alkyl group, and Z represents a C.sub.1 -C.sub.4 -alkyl, methylfuryl, pyridyl or unsubstituted phenyl group, or a phenyl group substituted by one or two halogen atoms or by a C.sub.1 -C.sub.4 -alkyl, alkoxy, trifluoromethyl or nitro group, or by a trifluoromethyl group and a halogen atom with the provisos that:
1. when X represents an amino group, Z, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have all the above indicated meanings;
2. when X represents an alkylamino group, Z may only represent a C.sub.1 -C.sub.4 -alkyl group or a phenyl group as defined hereabove and R.sub.1 may further represent a group of the formula:
in which R.sub.5 represents hydrogen or a C.sub.1 -C.sub.4 -alkyl group;
3. when X represents an amino group and Z is other than a phenyl group, R.sub.1 may further represent hydrogen or a group of the formula (IV) as above defined,
as well as a pyridine N-oxide of the compound of formula I and the pharmaceutically acceptable base and acid addition salts of said compounds.
2. 3-Ethylcarbamylsulfonamido-4-(3'-trifluoromethyl)-phenylaminopyridine-N- oxide.
3. 3-I sopropylcarbamylsulfonamido-4-(3'-methyl)-phenylaminopyridine-N-oxide.
8. A pharmaceutical composition containing an anti-inflammatory or diuretic effective amount of a compound of claim 1 and a pharmaceutical carrier or vehicle.