Synthesis and evaluation of the male antifertility properties of a series of N-unsubstituted sulfamates.

A series of six aliphatic and one carbocyclic N-unsubstituted sulfamates have been synthesized and evaluated as potential male antifertility agents. Three of the aliphatic sulfamates, 1,2-ethanediyl sulfamate (1), 1,3-propanediyl sulfamate (2), and 1,4-butanediyl sulfamate (3), when administered orally to male rats caused a decrease in the number of pregnant females and/or implantation coupled with increased embryonic and fetal resorption. The compounds were prepared by treating the appropriate glycol salt with sulfamoyl chloride or by the cleavage of a tert-butylsulfamate with trifluoroacetic acid.