Patent IL-125642-A (IL)
Title: Sulfonamide-substituted bi- and tricyclic dihydropyran compounds, processes for their preparation and pharmaceutical compositions comprising them
IPC: C07D491/04
Filed: 1998-08-03
Abstract: Potassium-channel blocking compounds of the formula 3188 ה' בכסלו התשס" ג - November 10, 2002 in which: R1 and R2 independently of one another are hydrogen, CF3, C2F5, C3F7, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms or phenyl, which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, methyl, methoxy, sulfamoyl and methylsulfonyl; or R1 and R2 together are an alkylene chain having 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms; where one CH2 group of the alkylene chain can be replaced by -O-,- CO-, -S-, -SO-, -SO2- or -NR10-; R10 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; R3 is R12 - CHaH2a [NR13)]m-; R12 is hydrogen or cycloalkyl having 2, 4, 5, 6, 7 or 8 carbon atoms, CF3, C2F5 or C3F7; a is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m is zero or 1; R13 is hydrogen or alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms; or R12 and R13 together are an alkylene group having 4, 5, 6, 7 or 8 carbon atoms, where one CH2 group of the alkylene group can be replaced by -O-, -[SOzero, 1 3189 ה' בכסלו התשס" ג - November 10, 2002 or 2]-, -CO- or NR10-; R10 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; R4 is R14 - CrH2r; r is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19 or 20; R14 is hydrogen, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, piperidyl, 1-pyrrolidinyl, N-morpholino, N-methylpiperazino, CF3, C2F5, C3F7, pyridyl, thienyl, imidazolyl or phenyl, which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, methyl, methoxy, sulfamoyl, methylsulfonyl and methylsulfonylamino; where one CH2 group of the group CrH2r can be replaced by -O-,- CH=CH-, -C:C-, -CO-, -CO-O-, -CO-NR11-, -[SOzero, 1 or 2] - or -NR11-; R11 is hydrogen or -(CaH2a)- R10; where one CH2 group of the group CaH2a can be replaced by - O-, CH=CH-, -C:C-, -CO-, -CO-O-, -O-CO-, -S-, -SO-, -SO2-, NR10- or -CONR10-; R10 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; or R3 and R4 together are an alkylene chain haivng 3, 4, 5, 6, 7 or 8 carbon atoms, where one CH2 group of the alkylene chain can be replaced by -O-, -[SOzero, 1 or 2]-, -CO- or -NR11-; R11 is hydrogen or -(CaH2a) - R10; where one CH2 group of the group CaH2a can be replaced by - O-, CH=CH-, -C:C-, -CO-, -CO-O-, -O-CO-, -S-, -SO-, -SO2-, NR10 - or -CONR10-; R10 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; R5 and R6 are -CR15=CR16-CR17=N-, -CR15=CR16-N=CR17-; -CR15=N-CR17=N-, -CR15=N-N=CR17-, -N=CR16-CR17=N- or -S-CR15=CR16-; R15, R16 and R17 independently of one another are hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3, or 4 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, CN, CF3, C2F5, N3, NO2, -CONR19R21, -COOR21, R22-CsH2s-Z- or phenyl, which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, methyl, methoxy, sulfamoyl and methylsulfonyl; R19 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; R21 is hydrogen, methyl, ethyl, phenyl or -CuH2u-NR19R20; where the phenyl is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, methyl, methoxy, sulfamoyl and methylsulfonyl; R20 is hydrogen or alkyl having 1, 2 or 3 carbon atoms; u is 2 or 3; R22 is hydrogen, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, -COOR21, CONR19R21, thienyl, imidazolyl, pyridyl, quinolyl, isoquinolyl, piperidyl, 1-pyrrolidinyl, N-morpholino, N-methylpiperazino, CF3, C2F7 or phenyl, which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF3, methyl, methoxy, sulfamoyl and methylsulfonyl; s is zero, 1, 2, 3, 4, 5 or 6; Z is -[S(O)zero, 1 or 2]-, CO-, -SO(0, 1 or 2)- NR11-, -SO2-O-, -O-, -NR11- or - [CO-NR11]-; R7 is hydrogen, hydroxyl, alkoxy having 1, 2, 3 or 4 carbon atoms, acyloxy having 1, 2, 3 or 4 carbon atoms, Cl, Br, F, alkyl having 1, 2, 3 or