Cephem Compounds with Latent Reactive Groups

A compound of formula:

• or salts, or solvates thereof,
• where M is:
• R is an acyl amino group (R1CO—NH—) or an alkyl group optionally substituted with a group selected from a halogen, a hydroxy group or a protected hydroxyl group;
• R2 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aryl, a pharmaceutically acceptable cation, when the CO2 group to which R2 is attached is negatively charged, or a carboxylate protecting group;
• R3 is hydrogen, a C1-C3-alkoxy group;
• —Z— is a linker between the two indicated atoms, which forms a 5- or 6-member carbocyclic or heterocyclic ring with the atoms to which it is linked;
• R16 is hydrogen, a C1-C3 alkyl group or a C1-C3 alkoxy group;
• R4, R5, R6, and R7 are independently selected from hydrogen, halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, amino, C1-C3 alkylamino, and C1-C3 dialkylamino;
• R11 and R12 are independently selected from hydrogen, hydroxyl, halogen, C1-C3 alkyl, cyano, and nitro groups,
• R13, if present, is selected from hydrogen, hydroxyl, halogen, C1-C3 alkyl, cyano, and nitro groups;
• A+ is a leaving group containing a positively charged nitrogen;
• L is an optional divalent linker moiety containing 1-6 carbon atoms and optionally one, two or three heteroatoms (N, S or O), where y is 1 or 0 to indicate presence or absence of the linker;
• wherein the phenyl ring of the styryl group is cis or trans or a mixture of is or trans with respect to the cepham ring;
• wherein the A+ group is bonded to the indicated phenyl ring of X through linker L or is a partially or fully unsaturated heterocyclic ring fused to the indicated phenyl ring, and
• wherein the indicated phenyl ring in X is a catechol having two hydroxyl group substituted on adjacent ring carbons.