Broad spectrum beta-lactamase inhibitors

A compound of formula:

• and pharmacologically acceptable salts thereof wherein:
• R is an acylamine group;
• R1 and R2, are independently selected from hydrogen, halogen, a (C1-C6) alkyl group, a (C1-C6) alkoxy group or a (C1-C6) —S-alkyl group;
• each of which groups is optionally substituted;
• Y is O—C+ or OR3, where R3 is hydrogen, an alkyl group or an aryl group, each of which groups is optionally substituted, and C+ is a pharmacologically acceptable cation;
• and M is selected from:
• where W is O and R6 and R7 are hydrogen, halogen or optionally substituted (C1-C6) alkyl groups;
• or
• where:
• each R8 is independently selected from hydrogen, halogen, or an optionally substituted (C1-C6) alkyl group;
• each R10 is independently selected from hydrogen, halogen, an optionally substituted (C1-C6) alkyl group, or a —CH2—X group;
• R12 is selected from hydrogen, an optionally substituted (C1-C6) alkyl group, or X;
• R13 and R14 are independently selected from hydrogen, an optionally substituted (C1-C6) alkyl group, or X;
• and
• X is a leaving group selected from halogen, a pyridinium, SC(O)R′, —OCOR′, —SH, —SR′, phenoxy, pentafluorophenoxy, tosyl, p-fluorotosyl, p-bromotosyl, p-nitrobenzyltosyl, or pentafluorotosyl group, where R′ is selected from optionally substituted alkyl and aryl groups;
• and
• wherein the compound contains one R2 and one M group, and formula B is substituted with at least one —CH2—X group and formulas E or F are substituted with at least one —CH2—X or X group.