PROCESS FOR PRODUCING 7-SUBSTITUTED-2,3-DIHYDRO-BICYCLIC-PYRAZOLIDINON DERIVATIVES

摘要

7-Substituted-2,3-(dihydro) bicyclic pyrazolidinones are intermediates for 7-substituted pyrazolidinone antimicrobials. The intermediates have the formula wherein Z is a group of the formula or and wherein: R1 is hydrogen, an organic or inorganic cation, a carboxy-protecting group or a non-toxic, metabolically-labile, ester-forming group; R2 is hydrogen, halo, C1 to C6 alkyl, C1 to C6 substituted alkyl, perfluoro C2 to C4 alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl or cyano; a group of the formula -CX3 wherein X is fluoro, chloro, bromo or iodo; a group of the formula -@@@7 wherein z is 0, 1 or 2 and R7 is C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, or a heterocyclic ring; a group of the formula -COR8 wherein R8 is hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, perfluoro C2 to C4 alkyl, trihalomethyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, amino, (monosubstituted)amino or disubstituted amino; a group of the formula -COOR9 wherein R9 is hydrogen, an organic or inorganic cation, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl substituted phenyl, a carboxy-protecting group or a non-toxic metabolically-labile, ester-forming group. or a group of the formula -CH2-S-Heterocyclic ring; R3 and R4 are hydrogen or; either R3 or R4 is C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl or a group of the formula -COOR10 wherein R10 has the same definition as R9; and the other is hydrogen; R5 and R6 are 1) each hydrogen; or 2) taken together and form a phthalimido group; or 3) either R5 or R6 is hydrogen and the other is an amino-protecting group; and Y is C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, C7 to C12 arylalkyl or C7 to C12 substituted arylalkyl. or a pharmaceutically acceptable salt thereof h