Derivatives of 4-amino-3-sulfonamido-pyridine

Details Derivatives of 4-amino-3-sulfonamido-pyridine Derivatives of 4-amino-3-sulfonamido-pyridine

C - Chemistry, Metallurgy

07

D

260/388.2, 260/2

C07D 401/00 (2006.01) C07D 201/00 (2006.01) C07D 213/74 (2006.01) C07D 213/75 (2006.01) C07D 223/00 (2006.01) C07D 521/00 (2006.01) C07F 5/00 (2006.01) C07F 9/00 (2006.01)

Patent

CA 1124720

ABSTRACT The invention is concerned with new pharmaccutically active sulfonamido-pyridine derivatives having the following general formula: Image (I) a- well as the pharmaceutically acceptable acid addition salts thereof, wherein Rl represents a hydrogen atom, a straight or branched chain C1 - C4 alkyl or C3 - C6 cycloalkyl group, a carbamoyl group of the formula: II) or a sulfonamido group of the formula: Image (III) in which R5 and R6 represent Cl - C4 alkyl radicals or form together with the nitrogen atom to which they are attached a saturated C4 - C6 heterocyclic radical; R2 represents a Straight or branched chain Cl - C8 alkyl group, a C1 - C8 halogenoalkyl, C3 - C8 cycloalkyl, C2 - C4 alkenyl, C2 - C4 alkynyl, or C1 - C8 hydroxyalkyl group, an alkoxyalkyl group containing a total of up to 8 carbon atoms, a phenyl radical which may be substituted with C1 - C4 alkyl, halogen, trifluoromethyl or acetyl, a phenylalkyl radical wherein the alkyl group contains 1 to 4 carbon atoms and the phenyl group may be substituted with C1 - C4 alkyl, halogen, trifluoromethyl or acetyl, a diphenylmethyl, isobornyl, furfuryl or tetrahydrofurfuryl group or a dialkyl- aminoalkyl radical containing 1 to 4 carbon atoms in each alkyl group, or a saturated or unsaturated nitrogenous heterocy- clic radical containing 5 to 7 atoms, which radical may be substituted with Cl - C4 alkyl, phenyl or halophenyl: cr Rl and R2 form together with the nitrogen atom to which they are hound a saturated nitrogenous heterocyclic radical containing 5 to 7 atoms, which radical may be substituted with Cl - C4 alkyl, phenyl or halophenyl X represents a Cl - C4 alkoxy radical or a group of the formula: Image (IV) in which R3 represents a hydrogen atom, a straight or branched chain Cl - C8 alkyl or a C2 - C4 alkenyl group: and R4 represents a straight or branched chain Cl - C8 alkyl radical, a C2 - C4 alkenyl, C2 - C4 alkenyl, or Cl - C8 hydroxyalkyl group, a diphenylmethyl, isobornyl, furfuryl, tertrahydrofurfuryl or phenylalkyl group wherein the alkyl group contains 1 to 5 carbon atoms, or a saturated or unsaturated nitrogenous heterocyclic radical containing 5 to 7 atoms which may comprise another heteroatom selected from nitrogen, oxygen and sulfur, which radical may be substituted with Cl - C4 alkyl, phenyl or halo- phenyl: or R3 and R4 form together with the nitrogen atom to which they are bound a saturated nitrogenous heterocyclic radical containing 5 to 7 atoms which may comprise another heteroatom selected from nitrogen, oxygen and sulfur: with the proviso that Rl is different from hydrogen or a Cl - C4 alkyl, when R2 represents an optionally substituted phenyl radical or a furfuryl of Cl - C4 alkyl group and X represents -NR3R4 in which R3 represents hydrogen and R4 represents a Cl - C4 alkyl or C2 - C3 alkenyl radical. The compounds of the invention possess valuable diuretic properties.

319934

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