.beta.-lactam compounds and process for their preparation

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 499/50 (2006.01) C07C 57/60 (2006.01) C07C 59/56 (2006.01) C07C 59/64 (2006.01) C07D 277/20 (2006.01) C07D 307/54 (2006.01) C07D 333/24 (2006.01) C07D 333/28 (2006.01) C07D 499/00 (2006.01) C07D 501/20 (2006.01)

Patent

CA 1178947

ABSTRACT OF THE DISCLOSURE The invention relates to a process for the preparation of a compound of formula Image (I) wherein R1 denotes an aromatic group, Z represents a group Image or Image (wherein R2 denotes hydrogen, a salt forming cation or a protective group for carboxylic acid, and R3 denotes hydro- gen or a residue of a nucleophilic compound) and X1 and X2 each represent hydrogen and halogen atom, provided that both X1 and X2 cannot represent hydrogen at the same time. This process is characterized in that it comprises either reacting a compound of formula Image (III) wherein R1, X1 and X2 have the above mentioned meanings, a reactive derivative thereof with respect to the carboxyl radical or a salt thereof, or reacting a compound of formula Image (IV) wherein R1, X1 and X2 have the above mentioned meanings and Y represents a hydroxyl group or a protective radical for the carboxylic acid, a reactive derivative thereof or a salt thereof, said compound of formula IV being obtained by either reacting a glyoxylic acid or acid derivative sub- stituted by an aromatic group with a Wittig reagent or reacting a 2-formylacetic acid or acid derivative substituted by an aromatic group with a halogenating agent; with a com- pound of formula Image (II) wherein Z has the above mentioned meaning, a reactive derivative thereof with respect to the amino radical or a salt thereof. The invention also relates to the so obtained compound of formula (I) which has a broad anti- bacterial spectrum and shows strong antibacterial activities against not only the gram-positive bacteria but also the gram negative bacteria, particularly the resistive gram- negative bacteria.

386380

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