Method for producing chemical compounds

C - Chemistry – Metallurgy – 07 – D

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C07D 519/00 (2006.01) C07D 499/00 (2006.01) C07D 503/00 (2006.01)

Patent

CA 1230113

ABSTRACT OF THE DISCLOSURE Alternative, specifically recited processes are provided herein for producing hitherto unknown compounds of the general Formula I: Image I and salts of the compound of Formula I with pharmaceutically-acceptable, non-toxic acids or bases, the pure diastereomers of the compound of Formula I, mixtures of the diastereomers of the compound of Formula I, salts of the diastereomers of the compound of Formula I and salts of the mixtures of the diastereomers of the compound of Formula I, in which R1 represents a phenyl, 4-hydroxyphenyl, 1,4-cyclohexadienyl or a 3-thienyl group, R2 represents a primary amino or a carboxy group, R3 represents a hydrogen atom, or a lower alkyl, aryl or aralkyl radical, preferably a methyl, phenyl or benzyl group, and A represents a radical of a .beta. -lactamase inhibitor containing a .beta. -lactam ring as well as a carboxy group, A being connected via the carboxy group. In these Abstr? of the Disclosure - Page 2 compounds, A may be a radical of Formula II: Image II in which R4 represents a hydrogen or a halogen atom, and R5 represents a hydrogen atom or an amino or acylamino group, with the proviso that at least one of, but not both of, R4 and R5 must be hydrogen, A may alternatively be a radical of Formula III: Image III in which R6 represents a halogen atom, e.g. Br or I. A may further alternatively be a radical of Formula IV: Image IV Abstract of the Disclosure - page 3 in which R7 represents a hydroxy group, or one of the radicals of known clavulanic acid derivatives with .beta. -lactamase inhibitory activity. The novel compounds formed by the specifically recited processes are useful in the treatment of bacterial infections. In particular, the new compounds are strongly active against .beta. - lactamase-producing bacteria.

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