Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-bacterial agents

A compound having a formula selected from the group consisting of:

• wherein
• a) R′1 is selected from the group consisting of hydrogen, —CN, protected —COOH, —COOR″, —(CH2)n′—R′5, —CONR6R7 and —C(═NR6)NHR7, R″ is selected from the group consisting of alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl, —CH2-alkenyl of 3 to 9 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, the aryl and aralkyl optionally substituted on the aromatic ring by at least one member of the group consisting of —NO2, protected OH, protected —NH2, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and halogen;
• R′5 is selected from the group consisting of protected —OH, —CN, protected —NH2, —CO —NR6R7, protected —COOH, —COO′R″, —OR″, —OCOH, —OCOR″, OCOOR″, OCONH2, OCONHR″, protected NHR″, NHCOR″, NHSO2R″, —NHCOOR″, —NH—CO—NHR″ and —NH—CONH2;
• n′ is 1 or 2,
• R6 and R7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms;
• R′4 and R3 together form heterocyclic aromatic of 5 to 6 vertices with 1 to 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen optionally substituted by at least one R′;
• R′ is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms optionally substituted by at least one oxo, halo, nitro, cyano, alkenyl of 2 to 6 carbon atoms, halogen, amino, —OH, protected —OH, —OR, —NHCOH, —NHCOR″, —NHCOOR″, —COOH, —COOR″, —C(C6H5)3 and —CH2—CH2—S(O)m—R″;
• m is 0, 1 or 2;
• R′2 is selected from the group consisting of hydrogen, halogen, R″, —S(O)mR″, —OR″, —NHCOH, —NHCOR″, —NHCOOR″ and —NHSO2R″;
• m is 0, 1 or 2;
• n is 1 or 2;
• —ZH is selected from the group consisting of —(CH2)n″—OH, —NHR′8—(CH2)n″— and —O—NHR8;
• n″ is 0 or 1,
• R′8 is selected from the group consisting of hydrogen, R″, protected —OH, —OR″, —Y′, —OY′, —Y′1, —OY1′, —Y′2, —OY′2, —Y′3, —OCH2—CH2—S(O)m—R″, —SiRaRbRc and —OSiRaRbRc;
• Ra, Rb and Rc are individually alkyl of 1 to 6 carbon atoms or aryl 6 to 10 carbon atoms;
• m is defined above with the proviso that ZH is not —(CH2)n″—OH when R′1 is —(CH2)n′—R′5;
• Y′ is selected from the group consisting of —COH, —COR″, —COOR″, —CONH2, —CONHR″, —CONHSO2R″, —CH2COOR″, protected —CH2tetrazol, —CH2SO2R″, —CH2PO(OR″)2, protected —CONHOH, protected CH2COOH, protected CH2CONHOH, protected CH2SO3H, protected —CH2PO(OR), protected
• —CH2PO(R)(OH) and protected —CH2PO(OH)2;
• Y′1 is selected from the group consisting of —SO2R″, —SO2NHCOH,
• —SO2NHCOR″, —SO2NHCOOR″, —SO2NHCONH2, —SO2NHCONHR″ and protected —SO3H;
• Y′2 is selected from the group consisting of —PO(OR″)2, protected —PO(OH)2, protected —PO(OH)(OR) and protected —PO(OH)(R);
• Y′3 is selected from the group consisting of protected tetrazol, tetrazol substituted by R″, protected squarate, protected —NH-tetrazole, protected —NR″-tetrazol, protected —NH—, —NR″-tetrazole substituted by R″, —NHSO2R″ and —NSO2R″;
• A is hydrogen or a nitrogen protective group,
• and R9 is a leaving group and their acid addition salts.