Patent EP-0196184-B1 (EP)
IPC: C07C259/06
Filed: 1986-03-14
Granted: 1992-09-16
Abstract: Novel compounds of formula (I) Ar-(L-Ar') q-(X) k-(Y) p-Q (I) wherein:- k,p and q are independently 0 or 1, provided that when k is 1 then p must also be 1; Ar represents either:   (i) naphthyl, tetrahydronaphthyl or pyridyl, any of which is optionally substituted by one or more substituents independently selected from C 1-4 alkyl (which may itself optionally be substituted by one or more halogen atoms), C 1-4 alkoxy, halo, nitro, amino, carboxy, C 1-4  alkoxycarbonyl and hydroxy, or (ii) phenyl optionally substituted by one or more substituents independently selected from phenyl (optionally substituted by one or more substituents independently selected from those specified as optional substituents i                      n (i) above) and said optional substituents specified in (i) above;   L is selected from -(CH2) r- (where r is 1-4), -O-, -CH2O-, -CH2S-, -OCH2-, -CONH-, -NHCO-, -CO- and -CH2NH-, and, Ar' represents phenylene, thienylene or pyridylene, any of which may be optionally substituted by one or more substituents independently selected from those specified as optional substituents in definition (i) of Ar; X represents oxygen, sulphur or carbonyl, provided that at least one atom separates said carbonyl group from any carbonyl group in Q as defined below; Y is C 1-10 alkylene or C 1-10 alkenylene;  Q represents a non-cyclic moiety selected from groups of formula <CHEM> in which one of m and n is 0 and the other is 1, and when n is 1 and m is 0, R<1> and R<2> are independently selected from hydrogen and C 1-4 alkyl, with the possibility that R<2> can also be C 5-7cycloalkyl, or when n is 0 and m is 1, R<1> is independently selected from hydrogen, C 1-4 alkyl, groups as defined for Ar above and groups of formula -COR<3> in which R<3> is selected from C 1-4 alkyl (optionally substituted by a carboxy or C 1-4 alkoxycarbonyl group) and groups of formula -N(R<4>)R<5> in which R<4> is hydrogen or C 1-4 alkyl and R<5> represents hydrogen C 1-4 alkyl or phenyl optionally substituted by one or more substituents independently selected from those specified as optional substituents in the definition (i) of Ar, and R<2> is selected from hydrogen, C 1-4 alkyl, amino, C 1-4 alkylamino, di-C 1-4 alkylamino, C 5-7 cycloalkylamino, C 5-7 cycloalkyl (C 1-4 alkyl) amino, anilino, N-C 1-4 alkylanilino and groups as defined for Ar above; or Q represents a cyclic moiety selected from 1-hydroxy-1,3-dihydro-imidazol-2-one and groups of formula <CHEM> in which Z represents a C 2-5 alkylene chain in which one of the carbon atoms may be replaced by a hetero atom; and salts thereof; with the proviso that:- when q is 0, k is 0 or 1 and p is 1, Ar is phenyl or naphthyl, either being optionally substituted by one or more substituents as specified in definition (i) of Ar, and X is oxygen or sulphur (in the case when k is 1) Y is C 1-10 alkylene and Q represents said non-cyclic moiety as hereinbefore defined in which one of R<1> and R<2> is hydrogen or C 1-4 alkyl; then the other of R<1> and R<2> is neither hydrogen nor C 1-4 alkyl. Also described are their preparation, compositions containing them and their use.