N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents

Article abstract of DOI:10.1021/jm00138a020

A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, <<2-cyano-3-(methylamino)phenyl>oxoacetic acid sodium salt (11a, Wy-41 195), has ED₅₀ value of 0.07 mg/kg po and has been selected for further evaluation.