Patent EP-0174832-A2 (EP)
Inventor: AL-SHAAR ADNAN HASSAN
IPC: A61P25/28
Filed: 1985-09-10
Abstract: Ethene derivatives of the general formula:
     wherein R 5  represents a heterocyclyl group, containing 1, 2 or 3 rings and one or more heteroatoms selected from nitrogen, oxygen, sulphur and selenium atoms, which is unsubstituted or substituted by one or more substituents R 8  [which may be the same or different and each represents a 
    
     halogen atom or an amino, carboxy, cyano, nitro, hydroxy, oxo, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzyloxycarbonylamino, sulphamoyl, tetrazol-5-yl, carbamoyl, thiocarbamoyl, arylcarbamoyl or aroyl group, or a straight-or branched-chain alkyl group containing from 1 to 10 carbon atoms, or a straight- or branched-chain alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylsulphamoyl, arylalkyl or arylalkoxy group containing from 1 to 10 carbon atoms in the alkyl moiety, a straight- or branched-chain alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarbamoyl or alkanoylamino group containing from 2 to 6 carbon atoms, an N-benzyloxycarbonyl-N-alkylamino group wherein the alkylamino moiety is straight- or branched-chain and contains from 1 to 6 carbon atoms, or a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group wherein the alkyl moieties may be straight or branched and may each contain from 1 to 6 carbon atoms and may be linked together to form a ring, or a group of the formula -CR 4 =CR 2 R 3 , or an aryl group which is unsubstituted or substituted by one or more substituents R S  (as hereinbefore defined), or a heterocyclylalkyl or arylalkyl group wherein the heterocyclyl or aryl moiety is as hereinbefore defined and the alkyl moiety is straight- or branched-chain and contains 1 or 2 carbons atoms, and R 1  represents a group of the general formula:
     wherein R 6  represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents R S  (as hereinbefore defined) or an aryl group which may be substituted by one or more substituents R 8  (as hereinbefore defined), or R 5  represents a quinonoidal group R 7  derived from a nitrogen-containing heterocyclyl group within the definition of R 5  as hereinbefore defined, bearing on said ring-nitrogen atom a substituent selected from straight- and branched-chain alkyl groups containing from 1 to 6 carbon atoms which may be substituted by one or more substituents R S  (as hereinbefore defined), and aryl groups which may be substituted by one or more substituents R S  (as hereinbefore defined), and R 1  represents an atom =N-, R 4  represents a hydrogen atom or a straight- or branched-chain alkoxy or alkylthio group containing from 1 to 6 carbon atoms, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms which may be substituted by one or more substituents R 8  (as hereinbefore defined), or an aryl group which may be substituted by one or more substituents R 8  (as hereinbefore defined), R 2  represents a cyano or formyl group, a straight- or branched-chain alkoxycarbonyl or alkylsulphonyl group containing up to 6 carbons, or a dialkylcarbamoyl or dialkylthiocarbamoyl group wherein the alkyl groups may be the same or different and each may be straight or branched and each contains from 1 to 6 carbon atoms, or an aryloxycarbonyl, arylsulphinyl or arylsulphonyl group wherein the aryl moiety may be substituted by one or more substituents R 8  (as hereinbefore defined), R 3  represents a group within the definition of R 2  or a hydrogen atom or a nitro group or an aryl or aroyl group which may be substituted by one or more substituents R 8  (as hereinbefore defined) or a straight- or branched-chain alkanoyl group containing up to 6 carbon atoms, and m and n each represents 1 or 2, and pharmaceutically acceptable salts thereof, with the provisos that the following classes of compounds are excluded:-
     (i) compounds of formula I wherein R 5  represents a pyridyl group which is unsubstituted or substituted by one or more substituents R 9  which may be the same or different and each represents a group within the definition of R e  other than oxo, straight- or branched-chain alkyl containing from 7 to 10 carbon atoms, straight- or branched-chain alkoxy, alkylthio, alkylsulphonyl, alkylamino, alkylsulphamoyl or arylalkyl containing from 7 to 10 carbon atoms in the alkyl moiety, straight- or branched-chain alkylsulphinyl or arylalkoxy containing from 1 to 10 carbon atoms in the alkyl moiety, or a group -CR 4 =CR 2 R 3  as hereinbefore defined, R 2  and R 3  may be the same or different and each represents a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R 9  (as hereinbefore defined), R' represents a group of formula II, R 4  and R 6  represent hydrogen atoms and m and n both represent 1;   (ii) compounds of formula I wherein R 5  represents a 5-halogenopyrid-2-yl group, R 2  and R 3  both represent cyano groups, R 1  represents a group of formula II, R 4  and R° represent hydrogen atoms and m and n both represent 1; and   (iii) compounds of formula I wherein R 5  represents a 1,2,4-triazolo[4,8-a]-quinoline group which is unsubstituted or substituted by one or more substituents R 10  which may be the same or different and each represents a group within the definition of R 9  or a straight- or branched-chain alkylsulphinyl group containing from 1 to 6 carbon atoms, R 2  and R 3  may be the same or different and each represents a cyano group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 6 carbon atoms, or a phenylsulphonyl group which may be unsubstituted or substituted by one or more substituents R 10  (as hereinbefore defined), R' represents a group of formula II, R 4  and R 6  represent hydrogen atoms and m and n both represent 1, possess useful pharmacological properties.