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US 5,478,942 AGranted
Cyclic urea derivatives and pharmaceutical compositions containing these compounds
AssigneeKarl Thomae GmbH
InventorsFrank Himmelsbach, Helmut Pieper, Volkhard Austel, Guenter Linz, Thomas Mueller, Johannes Weisenberger, Wolfgang Eisert
Life of this patent
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Abstract
The invention relates to cyclic urea derivatives of general formula ##STR1## wherein R.sub.a, R.sub.b, X and Y are as defined herein, pharmaceutical compositions containing the derivatives and processes for preparing them.
Claims22
A cyclic urea derivative of formula ##STR24## wherein Y is a --CR.sub.c .dbd.N-- or --N.dbd.CR.sub.c -group, wherein R.sub.c is a hydrogen atom, and C.sub.1-4 -alkyl, trifluoromethyl or phenyl group;
- one of the groups R.sub.a or R.sub.b is a group of formula
- A--B--C--
- wherein
- A is a straight-chained or branched C.sub.1-4 -aminoalkyl group, an amino, amidino or guanidino group, wherein in each of the above-mentioned groups, at one of the nitrogen atoms, one hydrogen atom may be replaced by a C.sub.1-4 -alkyl group or an alkoxycarbonyl group having a total of 2 to 5 carbon atoms or by a benzyloxycarbonyl group;
- B is a bond;
- a phenylene group which may be substituted by one or two C.sub.1-4 -alkyl groups, by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylsulphenyl, C.sub.1-4 -alkylsulphinyl, C.sub.1-4 -alkylsulphonyl, nitro, amino, acetylamino, benzoylamino or methanesulphonylamino group, or a C.sub.3-6 -cycloalkylene group;
- C is an ethylene group optionally substituted by a hydroxy group,
- a methylenecarbonyl group linked to the group B via the carbonyl group, or
- a phenylene group which may be substituted by one or two C.sub.1-4 -alkyl groups, by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylsulphenyl, C.sub.1-4 -alkylsulphinyl, C.sub.1-4 -alkylsulphonyl, nitro, amino, acetylamino, benzoylamino or methanesulphonylamino group;
- the other of the groups R.sub.a or R.sub.b is a group of formula
- F--E--D--
- wherein
- D is a C.sub.1-4 -alkylene group,
- a phenylene group which may be substituted by one or two C.sub.1-4 -alkyl groups, by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylsulphenyl, C.sub.1-4 -alkylsulphinyl, C.sub.1-4 -alkylsulphonyl, carboxymethoxy, methoxycarbonylmethoxy, nitro, amino, acetylamino, benzoylamino or methanesulphonylamino group,
- a cyclohexylene group optionally substituted by one or two methyl groups, or
- a 1,4-piperidinylene group, which is linked via the 1-position to the optionally substituted C.sub.1-4 -alkylene group of E;
- E is a bond;
- a C.sub.1-4 -alkylene group optionally substituted by one or two methyl groups or by a hydroxy, methoxy, amino, methylamino, dimethylamino, dibenzylamino, carboxymethyl or methoxycarbonylmethyl group,
- a C.sub.2-3 -alkenylene group;
- a phenylene group which may be substituted by one or two C.sub.1-4 -alkyl groups, by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl or C.sub.1-4 -alkoxy group, or
- a C.sub.1-2 -alkylene group linked to group D by the group W', wherein W' is an oxygen or sulphur atom, a sulphinyl, sulphonyl, --NH--, --N(C.sub.1-4 -alkyl)-, --N(COC.sub.1-4 -alkyl)-, --N(SO.sub.2 C.sub.1-4 -alkyl)-, aminocarbonyl or carbonylamino group;
- and
- F is a carbonyl group substituted by a hydroxy group, by a C.sub.1-6 -alkoxy group or by a phenylalkoxy group having 1 or 2 carbon atoms in the alkoxy part, wherein if A is an amino or aminoalkyl group optionally benzyloxycarbonylated at the nitrogen atom, the shortest distance between the nitrogen atom of this group and group F is at least 10 bonds;
- the tautomers, the stereoisomers, including the mixtures thereof, or the addition salts thereof.
21 more elements
Dependencies are inferred from the claim text.