C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/291.4, 260/3
C07D 295/18 (2006.01) C07D 295/13 (2006.01) C07D 295/14 (2006.01)
Patent
CA 1246562
ABSTRACT OF THE DISCLOSURE Substituted sulfonamidobenzamides useful as antiarrhythmic agents having the formula Image I wherein R is lower alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl (lower) alkyl, benzyl, or benzyl substituted by halogen, loweralkyl, loweralkoxy, or lower alkyl substituted by hydroxy, lower alkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-di-lower- alkylcarbamoyl and sulfamoyl; X and X1 are hydrogen and halogen; R1 is hydrogen, loweralkyl, unsaturated loweralkyl, loweralkoxy- loweralkyl, or collectively with R2 is an alkylene chain forming an azetidine, pyrrolidine, piperidine, or hexahydroazepine ring, or collectively with R3 is a bond or an alkylene chain forming an azetidine, pyrrolidine, piperidine or a hexahydroazepine ring, or collectively with R5 may produce a piperazine or a hexahydro-1,4- diazepine ring system; R2 is hydrogen, loweralkyl or collectively with R3 is a bond or an alkylene chain to form a saturated carbocylic ring or from 4 to 8 ring carbon atoms, R3 and R4 are hydrogen, loweralkyl or collectively is an alkylene chain forming a saturated carbocyclic ring of from 4 to 6 ring carbon atoms; R5 and R6 are hydrogen, loweralkyl, unsaturated loweralkyl, C1-C12 straight or branched chain alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl(lower)alkyl, or when taken together form a saturated heterocyclic ring of from 4 to 8 ring members which may be substituted by one or more methyl groups or may contain a -O-, or Image linkage wherein p is the integer 0, 1 or 2; R6 is loweralkyl substituted by phenyl which may be substituted by up to 3 sub- stitutents selected from hydroxy or methoxy groups; n is 0, 1 or 2; or a pharmaceutically acceptable salt thereof; with the provisos that; (a) R5 and R6 are not both hydrogen, (b) when either R5 or R6 is hydrogen then the other is a C5-C10 straight or branched chain alkyl, cycloalkyl, cycloalkyl lower alkyl or lower alkyl substituted by phenyl which may be substituted by up to 3 substituents selected from hydroxy or methoxy groups, (c) when any of R1 , R5 and R6 is unsaturated loweralkyl, the unsaturation is other than alpha to the nitrogen atom. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
476879
Davey David D.
Lumma William C.
Wohl Ronald A.
Marks & Clerk
Schering Aktiengesellschaft
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