3,7-disubstituted cephalosporins and preparation thereof

C - Chemistry – Metallurgy – 07 – D

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C07D 501/36 (2006.01) A61K 31/545 (2006.01)

Patent

CA 1102790

ABSTRACT OF THE DISCLOSURE: The present invention relates to a process for preparing new 3,7-disubstituted cephalosporins. More particularly it relates to 7-acylamino-3-pyrazinylthiomethyl-3-cephem-4- carboxylic acids are disclosed having the general formula: Image (I) wherein R is an alkyl having from 1 to 5 carbon atoms or Image R2-CH2-, R2-X-(CH2)n-, Image , and Image wherein Y=Y1=H Y=Y1=C1 Y=C1, Y1=F Y=H, Y1=C1 and in which n is an integer from 1 to 4, X is O or S, and R2 is thienyl, phenyl, 1,4-cyclohexadienyl, phenoxy, pyrazinyl and substituted phenyl, thienyl, pyrazinyl and phenoxy, the substituent being selected from the group consisting of hydroxy, chlorine, bromine, and alkyl and alkoxy having from 1 to 4 carbon atoms; R3 is alkali metal such as sodium or potassium, hydrogen, alkyl having from 1 to 4 carbon atoms, benzyl, trichloroethyl, methoxybenzyl, benzhydryl, pivaloyloxymethyl, and an alkaline earth metal; R1 may be a pyrazinyl of the general formulae: Abstract continued: Image or Image or Image (II) (III) (IV) in which R4, R5, R6 are equal or different and are selected from the group consisting of F, C1, Br, hydrogen, alkyl, phenyl, cyano, thiocyano, carboxyl, carboxyalkyl, carboxamido, thiocarboxamido, hydroxy, alkoxy, thiol, alkylthio, amino, alkylamino, phenylamino. By the terms alkyl, an alkyl having from 1 to 4 carbon atoms is intended. Processes for making them are also disclosed. The new cephalosporin derivatives of formula (I) exhibit a broad spectrum antibacterial activity and are useful as therapeutic agents in the treatment of infectious diseases caused by gram-negative and gram-positive bacteria.

278851

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