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

1. 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″, —(CH 2 ) n ′—R′ 5 , —CONR 6 R 7 and —C(═NR 6 )NHR 7 , R″ is selected from the group consisting of alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl, —CH 2 -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 —NO 2 , protected OH, protected —NH 2 , 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 —NH 2 , —CO —NR 6 R 7 , protected —COOH, —COO′R″, —OR″, —OCOH, —OCOR″, OCOOR″, OCONH 2 , OCONHR″, protected NHR″, NHCOR″, NHSO 2 R″, —NHCOOR″, —NH—CO—NHR″ and —NH—CONH 2 ;

n′ is 1 or 2,

R 6 and R 7 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 R 3 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(C 6 H 5 ) 3 and —CH 2 —CH 2 —S(O) m —R″;

m is 0, 1 or 2;

R′ 2 is selected from the group consisting of hydrogen, halogen, R″, —S(O) m R″, —OR″, —NHCOH, —NHCOR″, —NHCOOR″ and —NHSO 2 R″;

m is 0, 1 or 2;

n is 1 or 2;

—ZH is selected from the group consisting of —(CH 2 ) n″ —OH, —NHR′ 8 —(CH 2 ) n″ — and —O—NHR 8 ;

n″ is 0 or 1,

R′ 8 is selected from the group consisting of hydrogen, R″, protected —OH, —OR″, —Y′, —OY′, —Y′ 1 , —OY 1 ′, —Y′ 2 , —OY′ 2 , —Y′ 3 , —OCH 2 —CH 2 —S(O) m —R″, —SiR a R b R c and —OSiR a R b R c ; R a , R b and R c 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 —(CH 2 ) n″ —OH when R′ 1 is —(CH 2 ) n′ —R′ 5 ;

Y′ is selected from the group consisting of —COH, —COR″, —COOR″, —CONH 2 , —CONHR″, —CONHSO 2 R″, —CH 2 COOR″, protected —CH 2 tetrazol, —CH 2 SO 2 R″, —CH 2 PO(OR″) 2 , protected —CONHOH, protected CH 2 COOH, protected CH 2 CONHOH, protected CH 2 SO 3 H, protected —CH 2 PO(OR), protected

—CH 2 PO(R)(OH) and protected —CH 2 PO(OH) 2 ;

Y′ 1 is selected from the group consisting of —SO 2 R″, —SO 2 NHCOH,

—SO 2 NHCOR″, —SO 2 NHCOOR″, —SO 2 NHCONH 2 , —SO 2 NHCONHR″ and protected —SO 3 H;

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″, —NHSO 2 R″ and —NSO 2 R″;

A is hydrogen or a nitrogen protective group,

and R9 is a leaving group and their acid addition salts.

2. A compound of the formula

wherein R′ 1 , R′ 2 , R′ 4 , n, A and R′ 8 have the definition of claim 1 and their acid addition salts.

3. A compound of the formula

wherein —ZH, R′ 1 , R′ 2 , R′ 4 and n have the definition of claim 1 .

4. A compound of a formula selected from the group consisting of

wherein R′ 1 , R′ 2 , R′ 4 , A and n are as defined in claim 1 and their acid addition salts.