1,2,5-Thiazolidine Derivatives Useful for Treating Conditions Mediated by Protein Tyrosine Phosphatases (Ptpase)

A compound of the formula

• wherein
• R1 is hydrogen, —C(O)R5, —C(O)NR6R7 or —C(O)OR8 in which
• R5 and R6 are, independently from each other, hydrogen, cycloalkyl, aryl, heterocyclyl, aralkyl, heteroaralkyl or alkyl optionally substituted with one to four substituents selected from the group consisting of halogen, cycloalkyl, cycloalkoxy, alkoxy, alkyloxyalkoxy, amino, alkylamino, dialkylamino, aryl, aryloxy and heterocyclyl;
• R7 and R8 are, independently from each other, cycloalkyl, aryl, heterocyclyl, aralkyl, heteroaralkyl or alkyl optionally substituted with one to four substituents selected from the group consisting of halogen, cycloalkyl, cycloalkoxy, alkoxy, alkyloxyalkoxy, amino, alkylamino, dialkylamino, aryl, aryloxy and heterocyclyl;
• R2, R3 and R4 are, independently from each other, hydrogen, hydroxy, halogen, cyano, nitro, alkoxy, alkylthio, alkylthiono, sulfonyl, free or esterified carboxy, carbamoyl, sulfamoyl, optionally substituted amino, cycloalkyl, aryl, heterocyclyl, alkenyl, alkynyl or (C1-8)alkyl optionally substituted with one to four substituents selected from the group consisting of halogen, hydroxy, cycloalkyl, cycloalkoxy, acyl, acyloxy, alkoxy, alkyloxyalkoxy, amino, alkylamino, dialkylamino, acylamino, carbamoyl, thiol, alkylthio, alkylthiono, sulfonyl, sulfonamido, sulfamoyl, nitro, cyano, free or esterified carboxy, aryl, aryloxy, arylthio, alkenyl, alkynyl, aralkoxy, heteroaralkoxy, heterocyclyl and heterocyclyloxy;
• or
• R2 and R3 combined are alkylene which together with the ring atoms to which they are attached form a 5- to 7-membered fused ring provided R2 and R3 are attached to carbon atoms adjacent to each other;
• or
• R2 and R3 combined together with the carbon atom to which they are attached form a fused 5- to 6-membered aromatic or heteroaromatic ring provided R2 and R3 are attached to carbon atoms adjacent to each other;
• X is hydrogen, fluoro, cyano, or free or esterified carboxy;
• or
• X is —NR9C(O)R10—NR9C(O)OR11—NR9S(O)2R12—(CH2)mS(O)2R13—OS(O)2R14 or —ONC(O)NR15R16 in which
• R9 is hydrogen, lower alkyl, acyl, alkoxycarbonyl or sulfonyl;
• R10, R11, R12, R13 and R14 are, independently from each other, cycloalkyl, aryl, heterocyclyl, aralkyl, heteroaralkyl or (C1-8)alkyl optionally substituted with one to four substituents selected from the group consisting of halogen, hydroxy, cycloalkyl, cycloalkoxy, acyl, acyloxy, alkoxy, alkyloxyalkoxy, amino, alkylamino, dialkylamino, acylamino, carbamoyl, thiol, alkylthio, alkylthiono, sulfonyl, sulfonamido, sulfamoyl, nitro, cyano, free or esterified carboxy, aryl, aryloxy, arylthio, alkenyl, alkynyl, aralkoxy, heteroaralkoxy, heterocyclyl and heterocyclyloxy;
• or
• R10, R12 and R13 are, independently from each other, —NR17R18 in which
• R17 and R18 are, independently from each other, hydrogen, alkyl, cycloalkyl, aralkyl, aryl or heterocyclyl;
• or
• R17 and R18 combined are alkylene which together with the nitrogen atom to which they are attached form a 4- to 7-membered ring;
• R15 and R16 are, independently from each other, hydrogen, alkyl, cycloalkyl, aralkyl, aryl or heterocyclyl;
• or
• R15 and R16 combined are alkylene which together with the nitrogen atom to which they are attached form a 4- to 7-membered ring;
• m and n are, independently from each other, zero or an integer of 1;
• or
• C—X is replaced by nitrogen;
• Y is CH2, O or S;
• or a pharmaceutically acceptable salt thereof.