1, 2, 3-Triazole derivatives as new cannabinoid-1 receptor antagonists

A compound of formula I

• Ar—X—Y—Z formula I
• and pharmaceutically acceptable salts, prodrugs and solvates thereof,
• wherein Ar is
• in which R1 and R2 each independently represent H, phenyl, thienyl or pyridyl, unsubstituted or substituted by halo, hydroxy, cyano, nitro, thiohydroxy, amino, carbonyl, carbamoyl, sulfamoyl, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 alkyl alcohol, C1-4 haloalkyl, C1-4 haloalkylthio, C1-4 alkylamino, C1-4 alkylamido, C1-4 alkylsulfonyl, C1-4 haloalkylsulfonyl, C1-4 alkoxycarbonyl or C1-4 alkylcarbamoyl, with a proviso that one of R1 and R2 is not H;
• X is —(CH2)b— in which b is 0, 1, 2, 3 or 4;
• Y is —C(O)— or —S(O2)—;
• and
• Z is —(CH2)r(Ph)s in which s is 1 or 2 and r is 0, 1, 2, 3 or 4, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C5-9 aryl, C4-9 cycloalkyl, naphthyl, anthracenyl, OR3, NR4R5, or C4-9 heteroaryl or C3-10 heterocycloalkyl comprising one to three heteroatoms which each independently are N, O or S;
• R3 is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, —(CH2)r(Ph)s, C5-9 aryl, C4-9 cycloalkyl, naphthyl, anthracenyl, C4-9 heteroaryl or C3-10 heterocycloalkyl comprising one to three heteroatoms which each independently are N, O, or S;
• R4 and R5 each independently are H,
• —(CH2)r(Ph)s, —C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C5-9 aryl, C4-9 cycloalkyl, carbamoyl, ureido, adamantyl, —CHR6R7, or C4-9 heteroaryl or C3-10 heterocycloalkyl comprising one to three heteroatoms which each independently are N, O, or S, in which R6 and R7 each independently are C1-4 alkyl alcohol, C1-4 alkyl or benzyl, with a proviso that one of R4 and R5 is not H and one of R6 and R7 is not H,
• wherein R6 and R7 are unsubstituted or optionally substituted by thiohydroxy, hydroxy, phenyl, nitro, or C1-4 alkoxy;
• and
• R3, R4, R5, ph, C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C5-9 aryl, C4-9 cycloalkyl, C4-9 heteroaryl, C3-10 heterocycloalkyl, naphthyl, anthracenyl are unsubstituted or optionally substituted by halo, hydroxy, cyano, nitro, thiohydroxy, amino, carbonyl, carbamoyl, sulfamoyl, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 alkyl alcohol, C1-4 haloalkyl, C1-4 haloalkylthio, C1-4 alkylamino, C1-4 alkylamido, C1-4 alkylsulfonyl, C1-4 haloalkylsulfonyl, C1-4 alkoxycarbonyl, C1-4 alkylcarbamoyl, phenyl or benzyl.