Process for the production of penem compounds

Details Process for the production of penem compounds Process for the production of penem compounds

C - Chemistry, Metallurgy

07

D

260/111

C07D 499/00 (2006.01) C07D 205/09 (2006.01) C07D 233/54 (2006.01) C07D 409/12 (2006.01) C07D 499/88 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01)

Patent

CA 1226861

A B S T R A C T Penems of the formul a I Image I in which R is hydrogen or an organic radical, G is hydroxyloweralkyl and X is hydrogen, a pharmaceutically acceptable salt forming group or a metabolisable ester group, or a protecting group are disclosed. Process for their preparation involves reacting a compound II Image II - 2 - in which R1 and R2 are protected carboxy groups and Met is a thiophilic metal with a thiocarbonyl III S=C(Y)2 III in which Y is a leaving group, followed by removal of one of R1 and R2 to give a compound of formula I in which R is H together with its thione tautomer. Organic groups R can be introduced into the so-obtained compound by known methods. Alternatively the compound of formula I in which R is hydrogen can be made by intra-molecular cyclisation of the compound IV. Image IV G,Y and R2 being as previously defined. Various novel penems are also disclosed as well as three other processes for their preparation.

441887

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