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US 5,633,239 AGranted
Substituted benzenesulfonylureas and -thioureas, processes for their preparation, their use for the production of pharmaceutical preparations, and medicaments containing them
AssigneeHoechst Aktiengesellschaft
InventorsHeinrich Englert, Uwe Gerlach, Dieter Mania, Heinz G ogelein, Joachim Kaiser
Life of this patent
Estimating the term…
Abstract
Substituted benzenesulfonylureas and -thioureas of the formula I ##STR1## exhibit outstanding effects on the cardiovascular system.
Claims17
A substituted benzenesulfonylurea or benzenesulfonylthiourea of the formula I ##STR17## in which:
- R(1) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6 or 7 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
- R(2) is hydrogen, F, Cl, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, alkoxy having 1, 2, 3, 4, 5 or 6 carbon atoms, fluoroalkoxy having 1, 2, 3, 4, 5 or 6 carbon atoms, mercaptoalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms or a C.sub.b H.sub.2b+1 group in which one or more CH.sub.2 groups can be replaced by O, NH or S;
- wherein b is 1, 2, 3, 4, 5, 6, 7 or 8;
- R(3) is H, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a (C.sub.a H.sub.2a+1) group in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- R(4) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a C.sub.a H.sub.2a+1 group in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- or
- R(3) and R(4) together are a C.sub.b H.sub.2b group, in which one or more of the CH.sub.2 groups can be replaced by O, S or N;
- wherein b is 1, 2, 3, 4, 5, 6, 7 or 8;
- R(5) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a (C.sub.a H.sub.2a+1) group in which one or more CH.sub.2 groups are replaced by O, N or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- R(6) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms or a C.sub.a H.sub.2a+1 group, in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- E is oxygen or sulfur;
- X is oxygen or sulfur;
- Y is [CR(7).sub.2 ].sub.1-4, O, S or NH;
- R(7) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, F, Cl or Br;
- and their pharmaceutically acceptable salts.
16 more elements
A process for the preparation of a compound I a ##STR24## in which:
- R(1) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6 or 7 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
- R(2) is hydrogen, F, Cl, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, alkoxy having 1, 2, 3, 4, 5 or 6 carbon atoms, fluoroalkoxy having 1, 2, 3, 4, 5 or 6 carbon atoms, mercaptoalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, cycloalkyl having 3, 4, 5 or 6 carbon atoms or a C.sub.b H.sub.2b+1 group in which one or more CH.sub.2 groups can be replaced by O, NH or S;
- wherein b is 1, 2, 3, 4, 5, 6, 7 or 8;
- R(3) is H, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a C.sub.a H.sub.2a+1 group in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- R(4) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a C.sub.a H.sub.2a+1 group in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- or
- R(3) and R(4) together are a C.sub.b H.sub.2b group, in which one or more of the CH.sub.2 groups can be replaced by O, S or NH;
- wherein b is 1, 2, 3, 4, 5, 6, 7 or 8;
- R(5) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms, or a C.sub.a H.sub.2a+1 group in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- R(6) is H, aryl, alkyl having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, fluoroalkyl having 1, 2, 3, 4, 5 or 6 carbon atoms, fluorocycloalkyl having 3, 4, 5 or 6 carbon atoms or a C.sub.a H.sub.2a+1 group, in which one or more CH.sub.2 groups are replaced by O, NH or S;
- wherein a is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
- X is oxygen or sulfur;
- Y is [CR(7).sub.2 ].sub.1-4, O, S or NH;
- R(7) is hydrogen, alkyl having 1, 2, 3 or a 4 carbon atoms, F, Cl or Br;
- comprising the step of desulfurizing a compound of the formula I b ##STR25##
15 more elements
Dependencies are inferred from the claim text.