Patent IL-126955-A (IL)
Title: Sulfonamide-substituted fused 5-membered ring compounds and pharmaceutical preparations comprising them
IPC: C07C311/07
Filed: 1998-11-08
Abstract: Compounds having K+ channel blocking activity of the formula 3215 ה' בכסלו התשס" ג - November 10, 2002 in which: R1 and R2 independently of one another are hydrogen, CF3, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms; or R2 and R9 together are a bond; or R2 is -OR(10a), if X is -CR(22)R(23)-; R(10a) is hydrogen, acetyl or alkyl having 1, 2, or 3 carbon atoms; R3 is R(10b)-CnH2n-NR11 - or R(10b)-C2H2n-, where a CH2 group in the groups CnH2n may be replaced by -O-, -CO-, -S-, -SO-, -SO2- or -NR(12a)-; R(12a) is hydrogen, methyl or ethyl; R(10b) is methyl, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, CF3, C2F5 or C3F7; n is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; R11 is hydrogen or alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms; or R(10b) and R(11) together are a bond if n is greater than 2; or R3 together with R4 is an alkylene chain having 3, 4, 5, 6, 7 or 8 carbon atoms, where a CH2 group of the alkylene chain may be replaced by 3216 ה' בכסלו התשס" ג - November 10, 2002 -O-, -CO-, -S-, -SO-, SO2- or -NR(12a)-; R(12a) is hydrogen, methyl or ethyl; R4 is R(13) - CrH2r, where a CH2 group of the group CrH2r may be replaced by -O-, CH=CH-, -C:C-, -CO-, -CO-O-, -O-CO-, -S-, -SO-,- SO2-, -NR(14)- or -CONR(14)-; R14 is hydrogen, alkyl having 1, 2 or 3 carbon atoms, -CyH2y-OR(12b), -CyH2y -NR(12b)2; R(12b) is hydrogen, methyl or ethyl; y is 2 or 3; R13 is CH3, CF3, C2F5, C3F7, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, -NR(15)R(16), -CONR(15)R(16), -OR(17), -COOR(17), phenyl or a nitrogen- containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, where phenyl and the nitrogen-containing heterocycle are unsubstituted or substituted by 1 or 2 substituents, selected from the group consisting of F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; R(15) and R(16) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; or R(15) and R(16) together are a chain of 4 or 5 methylene groups of which one CH2 gorup may be replaced by -O-, -S-, -NH-, -N(CH3)- or -N(benzyl)-; R(17) is hydrogen, alkyl having 1, 2 or 3 carbon atoms, CzH2zOR(12c); R(12c) is hydrogen, methyl or ethyl; z is 2 or 3; r is zero, 1, 2, 3, 4, 5, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; R(5), R6, R(7) and R(8) independently of one another are hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl gaving 3, 4, 5, 6, 7 or 8 carbon atoms, -CN, -CF3, -C2F5, -C3F7, -N3, -NO2, -Y-CsH2s-R(18), phenyl, thienyl, furyl or a nitrogen-containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, where phenyl, thienyl, furyl and the nitrogen- containing heterocycle are unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, NO2, CN, -NH2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; Y is -O-, -CO-, -CO-O-, -O-CO-, -S-, -SO-, -SO2-, -O-SO2-, -SO2NR(10c)- or -CONR(10c)-, where the link to the skeleton is in each case effected through the atom on the left; R(10c) is hydrogen or alkyl having 1, 2 or 3 carbon atoms; s is zero, 1, 2, 3, 4, 5 or 6; R(18) is hydrogen, methyl, CF3, C2F5, C3F7, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, -OR(21), -COOR(21), -NR(15a) R(16a), -CONR(15a) R(16a), phenyl or a nitrogen- containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, where phenyl and the nitrogen-containing heterocycle are unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, NO2, CN, NH2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino; R(15a) and R(16a) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; or R(15a) and R(16a) together are a chain of 4 or 5 methylene groups of which one CH2 group may be replaced by -O-, -S-, -NH-,