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Claims for Patent: RE30633

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Claims for Patent: RE30633

Title: 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.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)
Application Number:06/119,601
Patent Claims: 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-ox ide..]. .[.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.sub.1 -C.sub.4 alkyl group;

R.sub.2 represents a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group;

R.sub.3 represents a C.sub.1 -C.sub.4 -alkyl, allyl, cyclohexyl, unsubstituted phenyl group or a phenyl group substituted by chloro;

A represents oxygen or sulfur; 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 proviso that when R represents a C.sub.1 -C.sub.4 alkyl group, Z may only represent a C.sub.1 -C.sub.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.sub.3 represents a C.sub.1 -C.sub.4 -alkyl group,

A represents oxygen, and

Z represents a C.sub.1 -C.sub.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.
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