Benzylidene thiazolidinediones and their use as antimycotic agents

A compound of formula Ia, or a salt or prodrug thereof,

• 95
• wherein
• A is O or S,
• X and Y independently represent O, CH2 and may be the same or different,
• Q is (CH2)m,CH(R1)—(CH2)n,
• R is OR6, NHR8,
• R1 is hydrogen, C1-C6 branched or straight chain alkyl optionally substituted with one or more of hydroxyl, COR, C1-C3 alkylphenyl or phenyl,
• R2 and R3 are independently hydrogen, C1-C10 branched or straight chain alkyl optionally substituted by C3-C6 cycloalkyl, C3-C6 cycloalkyl, C2-C10 branched or straight chain alkenyl, C2-C10 branched or straight chain alkynyl, (CH2)m—(CF2)nCF3 or (CH2)n—CH(R11)—(CH2)q-aryl where aryl is phenyl, pyridyl, thienyl, or furyl wherein phenyl is optionally substituted by one or more substituents selected from F, Cl, Br, CF3, OCF3, OR7, C1-C6 branched or straight chain alkyl, COR, CN, SO2R9, SONR8R9, and pyridyl, thienyl or furyl are optionally substituted by F, Cl, Br, CF3, OR6, C1-C6 branched or straight chain alkyl, provided that R2 and R3 are not both H, with the option that when X is CH2 then R3 may be OR6 and when Y is CH2, then R2 may be OR6;
• R2 and R3 may together form the group (CH2)qCHR10,
• R4 is hydrogen, F, Cl, Br, CF3, OR6, C1-C6 branched or straight chain alkyl or O(CH2)n—CH(R11)—(CH2)q-aryl where aryl is phenyl, pyridyl, thienyl, or furyl wherein phenyl is optionally substituted by one or more substituents selected from F, Cl, Br, CF3, OCF3, OR6, C1-C6 branched or straight chain alkyl, COR, CN, SO2R9, SONR8R9, and pyridyl, thienyl or furyl are optionally substituted by F, Cl, Br, CF3, OR6, C1-C6 branched or straight chain alkyl,
• R5 is hydrogen, C1-C6 branched or straight chain alkyl, phenyl optionally substituted by one or more substituents selected from F, Cl, Br, CF3, OCF3, OR6, C1-C6 branched or straight chain alkyl, COR, CN, SO2R9,
• R6 and R7 are independently hydrogen, C1-C6 branched or straight chain alkyl or C3-C6 cycloalkyl, or aryl, wherein aryl is phenyl optionally substituted by one or more substituents selected from F, Cl, Br, CF3, OCF3, C1-C6 branched or straight chain alkyl, COR, CN, SOR8,
• R8 is hydrogen, C1-C3 alkyl,
• R9 is C1-C6 branched or straight chain alkyl or C3-C6 cycloalkyl, phenyl, C1-C3 alkylphenyl,
• R10 is hydrogen, C1-C10 branched or straight chain alkyl, (CH2)p-aryl where aryl is phenyl optionally substituted by one or more substituents selected from F, Cl, Br, CF3, OCF3, C1-C6 branched or straight chain alkyl, COR, CN, SO2R8,
• R11 is hydrogen, C1-C6 branched or straight chain alkyl, CF3, CO2H, CO2R6, CONR6R9, C1-C6 branched or straight chain alkyl substituted by hydroxyl, CO2H, CO2R6 or CONR6R9;
• taken together R6 and R9 may form a ring optionally incorporating one or more additional heteroatoms wherein the ring may be optionally substituted by one or more of branched or unbranched C1-C6 alkyl, aryl, C1-C3 alkylaryl,
• m is 0-3;
• n is 0-2;
• p is 0-4;
• q is 0-1;
• with the proviso that when X and Y are both 0, R is OH and R4 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, O—CH2-phenyl or O—CH2-phenyl substituted with C1-C4 alkyl, C1-C4 alkoxy or hydroxy, then R2 and R3 are not hydrogen, C1-C6 alkyl, hydroxy, CH2-phenyl or CH2-phenyl substituted by C1-C4 alkyl, C1-C4 alkoxy or hydroxy.