Back to results
US 5,856,338 AGranted
Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparation comprising them
AssigneeHoechst Aktiengesellschaft
InventorsJoachim Brendel, Hans Jochen Lang, Uwe Gerlach, Klaus Weidmann
Life of this patent
Estimating the term…
Abstract
Compounds of formula I ##STR1## having the meanings indicated in the claims are outstandingly active substances for the production of medicaments for the prophylaxis and therapy of cardiovascular disorders, in particular arrhythmias; for the treatment of ulcers of the gastrointestinal region; or for the treatment of diarrheal illnesses.
Claims20
A compound of formula I ##STR20## in which:
- X is --NR(7)-;
- R(7) and R(1) together are a bond;
- Y is CR(11);
- R(11) is hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- R(2) is hydrogen, CF.sub.3, C.sub.2 F.sub.5, C.sub.3 F.sub.7, F, Cl, methoxy, 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, CF.sub.3, NO.sub.2, CN, NH.sub.2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
- R(3) is R(12)-C.sub.n --H.sub.2n --NR(13) or R(12)-C.sub.n H.sub.2n --,
- where a CH.sub.2 group of the group C.sub.n H.sub.2n can be replaced by --O--, --CO--, --S--, --SO--, --SO.sub.2 -- or --NR(10a);
- R(10a) is hydrogen, methyl or ethyl;
- R(12) is hydrogen, methyl, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, CF.sub.3, C.sub.2 F.sub.5 or C.sub.3 F.sub.7 ;
- n is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- R(13) is hydrogen or alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms;
- or
- R(12) and R(13) together are a bond if n is not less than 3;
- or
- R(3) and R(4) together are an alkylene chain having 3, 4, 5, 6, 7 or 8 carbon atoms,
- where a CH.sub.2 group of the alkylene chain can be replaced by --O--, --CO--, --S--, --SO--, --SO.sub.2 -- or --NR(10a)-;
- R(10a) is hydrogen, methyl or ethyl;
- R(4) is R(14)-C.sub.r H.sub.2r,
- where a CH.sub.2 group of the group C.sub.r H.sub.2r can be replaced by --O--, --CH.dbd.CH--, --C.tbd.C--, --CO--, --CO--O--, --O--CO--, --S--, --SO--, --SO.sub.2 --, --NR(10b)- or --CONR(10b)-;
- R(10b) is hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- R(14) is methyl, CF.sub.3, C.sub.2 F.sub.5, C.sub.3 F.sub.7, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, --OH, --COOH, --NR(23)R(24), 1-piperidyl, 1-pyrrolidinyl, 4-morpholinyl, 4-methylpiperazin-1-yl, pyridyl, thienyl, imidazolyl or phenyl,
- where pyridyl, thienyl, imidazolyl and phenyl are unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF.sub.3, NO.sub.2, CN, NH.sub.2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
- R(23) and R(24) independently of one another are each hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- or
- R(23) and R(24) together are an alkylene chain of 4 or 5 carbon atoms, of which one CH.sub.2 group can be replaced by --O--, --S--, --NH--, --N(CH.sub.3)-- or --N(benzyl)-;
- r is zero, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20;
- R(5) and R(6) together are a group --CR(15)=CR(16)-CR(17)=CR(18)-,
- where the group may be linked in either direction;
- R(15), R(16), R(17) and R(18) independently of one another are each hydrogen, F, Cl, Br, I, alkyl having 1, 2, 3, 4 or 5 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, --CN, --CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7, --N.sub.3, --NO.sub.2, --Z--C.sub.s H.sub.2s --R(22), thienyl or phenyl,
- which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF.sub.3, NO.sub.2, CN, NH.sub.2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
- Z is --O--, --CO--, --CO--O--, --O--CO--, --S--, --SO--, --SO.sub.2 --, --SO.sub.2 --O--, --SO.sub.2 NR(10c), --NR(10c)- or --CONR(10c)-;
- R(10c) is hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- s is zero, 1, 2, 3, 4, 5 or 6;
- R(22) is hydrogen, CF.sub.3, C.sub.2 F.sub.5, C.sub.3 F.sub.7, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, --NR(19)R(20), --COOR(21), 1-piperidyl, 1-pyrrolidinyl, 4-morpholinyl, 4-methylpiperazin-1-yl, pyridyl, thienyl, imidazolyl, quinolyl, isoquinolyl or phenyl,
- where pyridyl, thienyl, imidazolyl, quinolyl, isoquinolyl and phenyl are unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of F, Cl, Br, I, CF.sub.3, NO.sub.2, CN, NH.sub.2, OH, methyl, ethyl, methoxy, dimethylamino, sulfamoyl, methylsulfonyl and methylsulfonylamino;
- R(19) and R(20) independently of one another are each hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- or
- R(19) and R(20) together are an alkylene chain of 4 or 5 carbon atoms, of which one CH.sub.2 group can be replaced by --O--, --S--, --NH--, --N(CH.sub.3)-- or --N(benzyl)-;
- R(21) is hydrogen or alkyl having 1, 2 or 3 carbon atoms;
- or a physiologically tolerable salt thereof.
38 more elements
Dependencies are inferred from the claim text.