Sulfamylurea hypoglycemic agents. 6. High-potency derivatives

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Abstract
Synthetic methods for a series of novel sulfamylurea derivatives were developed. The hypoglycemic activity of simple 1-piperidinosulfonylureas is greatly enhanced by attaching an acylaminoethyl function in the 4 position of the piperidine ring. Optimum activity is achieved in the rat when the acyl radical is 5-chloro-2-methoxybenzoyl, 2-methoxynicotinyl, 5-chloro-2-methoxynicotinyl, 1,2-dihydro-1-methyl-2-ketonicotinyl, 2,3-ethylenedioxybenzoyl, quinoline-8-carbonyl, or 6-chloroquinoline-8-carbonyl. Optimal substituents on the terminal urea N are cyclohexyl, bicycloheptenylmethyl, and in certain cases propyl, 7-oxabicycloheptanylmethyl and adamantyl. One of these compounds, gliamilide was well tolerated in man and it displayed a very short plasma half-life.

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