Imidazonline compounds

A process for producing a compound of the general formula (I):

• wherein Ar1, Ar2 and A3 represent independently aryl which may be substituted, the substituent being selected from the group consisting of cyano, halogen atom, nitro, lower alkyl, halo(lower)alkyl, hydroxy(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkenyl, lower alkylamino, di-lower alkylamino, lower alkanoylamino, lower alkylsulfonylamino, arylsulfonylamino, hydroxy, lower alkoxy, halo(lower)alkoxy, aryloxy, heteroaryloxy, lower alkylthio, carboxyl, formyl, lower alkanoyl, lower alkoxycarbonyl, carbamoyl, lower alkylcarbamoyl, di-lower alkylcarbamoyl, lower alkylsulfonyl, arylsulfonyl, aryl and heteroaryl;
• R1 represents a group represented by the formula of —Ar3;
• R2 and R3 represent independently hydrogen atom, cyclo(lower)alkyl, lower alkenyl or lower alkyl which may be substituted, the substituent being selected from the group consisting of halogen atom, lower alkylamino, di-lower alkylamino, lower alkanoylamino, hydroxy, lower alkoxy, formyl, lower alkoxycarbonyl, lower alkylcarbamoyl and di-lower alkylcarbamoyl;
• provided that when both R2 and R3 represent hydrogen atom, Ar1, Ar2 and R1 do not represent simultaneously an unsubstituted phenyl group;
• or a salt or pharmaceutically acceptable ester of a carboxyl group thereof, which comprises reacting a compound of the general formula (II):
• wherein Ar1p and Ar3p represent independently aryl which may be substituted, the substituent being selected from the group consisting of cyano, halogen atom, nitro, lower alkyl, halo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, loweralkenyl, di-lower alkylamino, lower alkoxy, halo(lower)alkoxy, aryloxy, heteroaryloxy, lower alkylthio, formyl, lower alkanoyl, lower alkoxycarbonyl, di-lower alkylcarbamoyl, lower alkylsulfonyl, arylsulfonyl, aryl, heteroaryl and an optionally protected, hydroxy(lower)alkyl, lower alkylamino, lower alkanoylamino, lower alkylsulfonylamino, arylsulfonylamino, hydroxy, carboxyl, carbamoyl, or lower alkylcarbamoyl group;
• R1p represents a group represented by the formula of —Ar3p;
• R2p and R3p represent independently hydrogen atom, cyclo(lower)alkyl, lower alkenyl or lower alkyl which may be substituted, the substituent being selected from the group consisting of halogen atom, di-lower alkylamino, lower alkoxy, formyl, lower alkoxycarbonyl, di-lower alkylcarbamoyl and an optionally protected, lower alkylamino, lower alkanoylamino, hydroxy or lower alkylcarbamoyl group;
• with an acid addition salt of the compound represented by the general formula (III)
• wherein Ar2p represents aryl which may be substituted, the substituent being selected from the group consisting of cyano, halogen atom, nitro, lower alkyl, halo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkenyl, di-lower alkylamino, lower alkoxy, halo(lower)alkoxy, aryloxy, heteroaryloxy, lower alkylthio, formyl, lower alkanoyl, lower alkoxycarbonyl, di-lower alkylcarbamoyl, lower alkylsulfonyl, arylsulfonyl, aryl, heteroaryl and an optionally protected, hydroxy(lower)alkyl, lower alkylamino, lower alkanoylamino, lower alkylsulfonylamino, arylsulfonylamino, hydroxy, carboxyl, carbamoyl, or lower alkylcarbamoyl group;
• R4 represents amino or lower alkoxy;
• to provide a compound of the general formula (IV):
• wherein Ar1p, Ar2p, R1p and R3p have the same meanings as described above;
• optionally followed by cleavage of a protecting group.

A method of treating bulimia, obesity or diabetes comprising administering to a patient in need thereof an effective amount of a compound of the general formula (I):

• wherein Ar1, Ar2 and Ar3 represent independently aryl which may be substituted, the substituent being selected from the group consisting of cyano halogen atom, nitro, lower alkyl, halo(lower)alkyl, hydroxy(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkenyl, lower alkylamino, di-lower alkylamino, lower alkanoylamino, lower alkylsulfonylamino, arylsulfonylamino, hydroxy, lower alkoxy, halo(lower)alkoxy, aryloxy, heteroaryloxy, lower alkylthio, carboxyl, formyl, lower alkanoyl, lower alkoxycarbonyl, carbamoyl, lower alkylcarbamoyl, di-lower alkylcarbamoyl, lower alkylsulfonyl, arylsulfonyl, aryl and heteroaryl;
• R1 represents a group represented by the formula of —Ar3;
• R2 and R3 represent independently hydrogen atom, cyclo(lower)alkyl, lower alkenyl or lower alkyl which may be substituted, the substituent being selected from the group consisting of halogen atom, lower alkylamino, di-lower alkylamino, lower alkanoylamino, hydroxy, lower alkoxy, formyl, lower alkoxycarbonyl, lower alkylcarbamoyl and di-lower alkylcarbamoyl;
• provided that when both R2 and R3 represent hydrogen atom, Ar1, Ar2 and R1 do not represent simultaneously an unsubstituted phenyl group;
• or a salt or pharmaceutically acceptable ester of a carboxyl group thereof.