Patent DE-3677253-D1 (DE)
Inventor: JUNGHEIM LOUIS NICKOLAUS
IPC: C07F9/547
Filed: 1986-04-28
Granted: 1991-03-07
Abstract: 7-Substituted bicyclic pyrazolidinone compound as antimicrobials and the corresponding intermediates, are discussed or provided. The use of the antimicrobial compounds in pharmaceutical compositions and in methods for treating bacterial infections is set forth. The pyrazolidinone compounds are of the formula 
<CHEM>
 wherein one of R1 and 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, a heterocyclic ring, nitro or cyano;
 a group of the formula
 -CX3
 wherein X is fluoro, chloro, bromo or iodo; a group of the formula 
<CHEM>
 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;
 a group of the formula
 -PO3(R10)2
 wherein R10 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, or substituted phenyl;
 a group of the formula
 -CH2-@ IDENTICAL Q
 wherein -@ IDENTICAL Q is a quarternary ammonium group; or a group of the formula
 -CH2-S-Heterocyclic ring;
 a group of the formula
 -OR11
 wherein R11 is hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl or C1 to C7 acyl;
 or a group of the formula
 -NR12R13
 wherein R12 and R13 are the same or different and are hydrogen C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 arylalkyl, C7 to C12 substituted arylalkyl, phenyl, substituted phenyl, C1 to C7 acyl, or a group of the formula;
 @

 ORq
 wherein Rq is C1 to C6 alkyl, C7 to C12 arylalkyl or phenyl; and the other of R1 and R2 is a group of the formula
 -COOR14
 wherein R14 is hydrogen, an organic or inorganic cation, a carboxy-protecting group or a non-toxic, metabolically-labile ester forming group; and
 R3 and R4 are the same or different and are hydrogen, 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
 -COOR15
 wherein R15 has the same definition as R9;
 R5 and R6 are:
 1) each hydrogen, an amino protecting group; or acyl group derived from a C1 to C30 carboxylic acid;
 provided that at least one of R5 and R6 must be hydrogen; or
 2) taken together to form a phthalimido group;
 or a pharmaceutically-acceptable salt thereof.