1427211 Cephalosporins SMITHKLINE CORP 12 June 1973 [14 June 1972 15 Sept 1972 11 May 1973] 27795/73 Heading C2C Novel cephalosporins, having antibacterial activity, of Formula I wherein A is hydrogen, acetoxy, methoxy, methylthio or monocyclic heterocyclic thio, and pharmaceutically acceptable salts thereof, are prepared by acylating a compound of formula wherein A is as defined above, with p-hydroxymethylphenylglycine or an activated derivative thereof, the amino group being protected with a removable protecting group. Following acylation, the protective groups may be removed with trifluoroacetic acid and the resulting salt may be converted to the zwitterionic compound by means of basic ion exchange resin. The preparation of 7-(-amino-p-hydroxymethylphenylacetamido) cephalosporanic acid, 7-(- amino - p - hydroxymethylphenylacetamido)- 3 - desacetoxy cephalosporanic acid, 7 - (- amino - p - hydroxymethyl - phenylacetamido)- 3 - (1 - methyl - 1,2,3,4 - tetrazol - 5 - ylthiomethyl) - 3 - cephem - 4 - carboxylic acid, 7- ( - amino - p - hydroxymethylphenylacetamido) - 3 - (1,2,3 - triazol - 5 - ylthiomethyl)- 3 - cephem - 4 - carboxylic acid and 7 - (- amino - p - hydroxymethylphenylacetamido)- 3 - (5 - methyl - 1,3,4 - thiadiazol - 2 - ylthiomethyl) - 3 - cephem - 4 - carboxylic acid is described in the examples. Antibacterial compositions, suitable for injection or oral administration, comprise a compound of Formula I and a pharmaceutically acceptable carrier.
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