7-(2-Amino-4-thiazolyl)-acetamido cephalosporanic acids

Details 7-(2-Amino-4-thiazolyl)-acetamido cephalosporanic acids 7-(2-Amino-4-thiazolyl)-acetamido cephalosporanic acids

1982-01-27

1984-01-17

Coughlan, Jr., Paul M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

544 22, 544 28, 548194, 548195, 548196, C07D27740, C07D50156

Patent

active

044265190

ABSTRACT:
Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO-- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.2, A may further be selected from the group consisting of an equivalent of an alkali metal, an alkaline earth metal, magnesium, --NH.sub.4 and a non-toxic, pharmaceutically acceptable organic amine and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and a novel process and novel intermediates for their preparation.

REFERENCES:
patent: 4278793 (1981-07-01), Durckheimer et al.
patent: 4305937 (1981-12-01), Kamiya et al.

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