3-Lower alkylcarbamylsulfonamido-4-phenylaminopyridines, 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 1 -C 4 -alkylamino, oxy or thio group, R 1 represents a group of the formula R 3 NHCA (II), wherein A represents oxygen or sulfur, and R 3 represents a C 1 -C 4 -alkyl, alkenyl, cycloalkyl, phenyl (which may be substituted) or R 4 CO (III) group, R 4 representing a phenyl group (which may be substituted), R 2 represents hydrogen or a C 1 -C 4 alkyl group and Z represents a C 1 -C 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.

We claim: .[. 
     
       1.  A compound of the following formula: ##STR10## in which X represents an amino or C 1  -C 4  -alkylamino group;   R 1  represents a group of the formula:   R.sub.3 NHCA                                               (II),       where A represents oxygen or sulfur and R 3  represents a C 1  -C 4  -alkyl, allyl, cyclohexyl, unsubstituted phenyl group or a phenyl group substituted by chloro, or a group of the formula R 4  CO(III), wherein R 4  represents an unsubstituted phenyl group or a phenyl group substituted by chloro; R 2  represents hydrogen or a C 1  -C 4  -alkyl group, and Z represents a C 1  -C 4  -alkyl, methylfuryl, pyridyl or unsubstituted phenyl group, or a phenyl group substituted by one or two halogen atoms or by a C 1  -C 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 1 , R 2 , R 3  and R 4  have all the above indicated meanings; 2. when X represents an alkylamino group, Z may only represent a C 1  -C 4  -alkyl group or a phenyl group as defined hereabove and R 1  may further represent a group of the formula:   R.sub.5 CO                                                 (IV)       in which R 5  represents hydrogen or a C 1  -C 4  -alkyl group;   3. when X represents an amino group and Z is other than a phenyl group, R 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-Isopropylcarbamylsulfonamido     
     
     
        4-(3'-methyl)-phenylaminopyridine-N-oxide..]. 4. 3-Methylcarbamylsulfonamido-4-(3'-trifluoromethyl)-phenylaminopyridine. 
     
     
        . 3-Ethylcarbamylsulfonamido-4-(3'-trifluoromethyl)-phenylaminopyridine. 
     
     
           3-Isopropylcarbamylsulfonamido-4-(3'-chloro)-phenylaminopyridine. 
     
     
        7. 3-Methylcarbamylsulfonamido-4-(3'-methyl)-phenylaminopyridine. 8. A pharmaceutical composition .[.containing an anti-inflammatory, or.]. .Iadd.comprising a .Iaddend.diuretic effective amount of a compound of claim 9 .[.and.]. .Iadd.together with .Iaddend.a pharmaceutical carrier.[.or vehicle.].. .Iadd.9. A compound of the formula: ##STR11## in which: R represents a hydrogen atom or a C 1  -C 4  alkyl group; R 2  represents a hydrogen atom or a C 1  -C 4  -alkyl group;   R 3  represents a C 1  -C 4  -alkyl, allyl, cyclohexyl, unsubstituted phenyl group or a phenyl group substituted by chloro;   A represents oxygen or sulfur; and   Z represents a C 1  -C 4  -alkyl, methylfuryl, pyridyl or unsubstituted phenyl group or a phenyl group substituted by one or two halogen atoms or by a C 1  -C 4  -alkyl, alkoxy, trifluoromethyl or nitro group or by a trifluoromethyl group and a halogen atom;   with the proviso that when R represents a C 1  -C 4  alkyl group, Z may only represent a C 1  -C 4  alkyl or a phenyl group as defined hereabove, and the pharmaceutically acceptable base addition salts or acid addition     
     
     
        salts of said compounds. .Iaddend. .Iadd.10.  A compound according to claim 9, in which: R represents hydrogen,   R 3  represents a C 1  -C 4  -alkyl group,   A represents oxygen, and   Z represents a C 1  -C 4  -alkyl group or a phenyl group as defined in claim 9. .Iaddend. .Iadd.11. 3-Isopropylcarbamylsulfonamido-4-(3'-methyl)phenyl-aminopyridine. .Iaddend. .Iadd.12. A pharmaceutical composition comprising a diuretic effective amount of the compound of claim 3 together with a pharmaceutical carrier. .Iaddend.