Heterocycle substituted aryloxyaniline derivatives and their use as MDR ligands

An aryloxyaniline derivative represented by the formula:

• wherein Ar1 and Ar2 are the same or different, and are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group or a naphthyl group, provided that Ar1 and Ar2 are not both phenyl or both naphthyl and are not phenyl and naphthyl, R1 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group or a group of the formula:
• —NR2(R3) (wherein R2 and R3 are the same or different, and are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms), X1 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a phenoxy group, a halogen atom, a trifluoromethyl group, a carbamoyl group or an aminosulfonyl group, Y1 is a branched or unbranched alkylene group having 1 to 6 carbon atoms or a single bond;
• and pharmaceutically acceptable salts thereof, and
• wherein the substituted phenyl group is a phenyl group substituted with one to three members selected from the group consisting of:
• an alkyl group having 1 to 10 carbon atoms,
• an alkyl group having 1 to 10 carbon atoms substituted with halogen atoms, hydroxyl groups, carboxyl groups or alkoxycarbonyl groups,
• an alkenyl group having 2 to 10 carbon atoms,
• an alkoxy group having 1 to 10 carbon atoms,
• an alkylthio group having 1 to 10 carbon atoms,
• a group of the formula:
• —O—Z—R4 (wherein Z is a branched or unbranched alkylene group having 1 to 10 carbon atoms, and R4 is an amino group, an amino group substituted with one or two of an alkyl group having 1 to 7 carbon atoms, a cyclic amino group having 2 to 7 carbon atoms, a hydroxyl group, a carboxyl group or an alkoxycarbonyl group),
• an alkanoyl group having 2 to 10 carbon atoms or a ketal form thereof,
• a formyl group or an acetal form thereof,
• a carboxyl group,
• an alkoxycarbonyl group having 2 to 10 carbon atoms,
• a carbamoyl group,
• a carbamoyl group substituted with one or two of an alkyl group having 1 to 10 carbon atoms on the nitrogen atom,
• an aminosulfonyl group,
• an aminosulfonyl group substituted with one or two of an alkyl group having 1 to 10 carbon atoms on the nitrogen atom,
• a halogen atom, and
• a nitro group, and
• wherein the substituted pyridyl group is a pyridyl group substituted with one to three of an alkoxy group having 1 to 10 carbon atoms.