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US 5,852,192 AGranted
Cyclic urea derivatives, pharmaceutical compositions containing these compounds and processes for preparing them
AssigneeDr. Karl Thomae GmbH
InventorsFrank Himmelsbach, Helmut Pieper, Volkhard Austel, Guenter Linz, Johannes Weisenberger, Wolfgang Eisert, Thomas Mueller
Life of this patent
Estimating the term…
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.
Claims10
A cyclic urea derivative of the formula ##STR24## wherein X, represents a carbonyl group;
- Y represents an ethylene group;
- one of the groups R.sub.a or R.sub.b represents a group of thc formula
- A--B----C--
- wherein A represents a straight-chained or branched C.sub.1-5 -aminoalkyl group, an amino, amidino or guanidino group, whilst in each of the above-mentioned groups at one of the nitrogen atoms, one or two hydrogen atoms may be replaced by a C.sub.1-4 -alkyl or one hydrogen atom may be replaced by a C.sub.2-5 -alkoxycarbonyl group or by an alkylcarbonyl, arylcarbonyl, aryloxycarbonyl or aralkoxycarbonyl group, or A may represent a cyano group or a cyanoalkyl group having 1 to 4 carbon atoms in the alkyl moiety;
- B represents a bond, and
- C represents a phenylene group which may be mono- or disubstituted by fluorine, chlorine or bromine atoms, by C.sub.1-4 -alkyl groups, by trifluoromethyl, hydroxy, alkoxy, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, (R.sub.1).sub.2 N--,(R.sub.1).sub.2 NCO--,(R.sub.1).sub.2 NSO.sub.2 -- or nitro groups or by R.sub.1 NH-groups substituted by an alkylcarbonyl, aralkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkylsulphonyl, aralkylsulphonyl or arylsulphonyl group, whilst the substituents may be identical or different;
- the other of the groups R.sub.a or R.sub.b represents a group of the formul a
- F--E--D--
- wherein D represents a cyclohexaline group optionally substituted by an alkyl, aralkyl or aryl group, wherein one CH moiety is replaced by a nitrogen atom, whilst additionally one methylene group adjacent to the nitrogen atom may be replaced by a carbonyl group;
- E represents
- a C.sub.1-5 -alkylene group or a C.sub.2-5 -alkenylene group, each of which may be substituted by one or two alkyl groups, or by a hydroxy, alkoxy, amino, alkylamino, aralkylamino, dialkylamino, bis(aralkyl)amino, carboxyalkyl, alkoxycarbonylalkyl or aralkoxycarbonylalkyl group;
- and
- F represents a carbonyl group substituted by a hydroxy or C.sub.1-6 -alkoxy group, whilst a C.sub.1-3 -alkoxy group may be substituted in the 1-, 2- or 3-position by an aryl group, whilst if A represents a cyano group or an amino or aminoalkyl group optionally benzoylated or benzyloxy-carbonylated at the nitrogen atom, the shortest spacing between the nitrogen atom of these groups and group F is at least 10 bonds;
- or a tautomer or salt thereof,
- and, wherein, unless otherwise specified,
- the above-mentioned alkyl, alkylene, alkenylene or alkoxy moieties may each contain 1 to 3 carbon atoms, and
- the term "an aryl group" used above denotes a phenyl group which may be monosubstituted by a trifluoromethyl, carboxy, (R.sub.3).sub.2 NCO--, alkoxycarbonyl, alkylcarbonyl, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, nitro, (R.sub.3).sub.2 N--, alkylcarbonyl-NR.sub.3 -, aralkylcarbonyl-NR.sub.3 -, arylcarbonyl-NR.sub.3 -, heteroarylcarbonyl-NR.sub.3 -, alkylsulphonyl-NR.sub.3 -, aralkylsulphonyl-NR.sub.3 -, arylsulphonyl-NR.sub.3 - or (R.sub.3).sub.2 N-sulphonyl group or may be mono-, di- or trisubstituted by fluorine, chlorine or bromine atoms or by hydroxy, alkoxy or alkyl groups having 1 to 4 carbon atoms.
14 more elements
1-(4-amidino-phenyl)-3-imidazolidin-2-one or a salt thereof.
Dependencies are inferred from the claim text.