US 4,362,721 A · Penicillanic and cephalosporanic derivatives, preparation thereof, and pharmaceutical compositions containing same

Abstract

There are disclosed penicillanic and cephalosporanic derivatives of the formula: ##STR1## wherein R is H or --OH; R.sub.1 is a carbohydrate hexose radical of 3-O-glucose, 6-O-galactose, 3-O-glucose acetals, 3-O-glucose ketals, 6-O-galactose acetals, and 6-O-galactose ketals, and R.sub.2 is: ##STR2## where R.sub.3 is H or an alkali or alkaline-earth metal. The preparation of the derivatives and pharmaceutical compositions containing same are also disclosed. A process according to the invention comprises reacting a compound of the formula ##STR3## with a hexose carbohydrate, in --OH protected form, in an aqueous medium, in the presence of a water-miscible organic solvent, in the presence of a base, the reaction product being optionally transformed into the derivative wherein R.sub.1 is a carbohydrate in the unprotected form by treatment with Lewis' acid or a hydrogen halide acid. The compounds according to the invention are used in pharmaceutical compositions useful for treatment of infections by gram-positive and gram-negative pathogenous bacteria.

Claims29

Dependent claims

A penicillanic and cephalosporanic derivative of the formula (I):

##STR9## wherein R is H or --OH;
R.sub.1 is a hexose carbohydrate radical selected from the group consisting of 3-O-glucose, 6-O-galactose, 3-O-glucose acetals, 3-O-glucose ketals, 6-O-galactose acetals, and 6-O-galactose ketals, R.sub.2 is a member selected from the group consisting of ##STR10## and R.sub.3 is H or an alkali or earth-alkaline metal.

Dependencies are inferred from the claim text.

Penicillanic and cephalosporanic derivatives, preparation thereof, and pharmaceutical compositions containing same

Life of this patent

Penicillanic and cephalosporanic derivatives, preparation thereof, and pharmaceutical compositions containing same

Life of this patent

Abstract

Claims29