Amino sugar derivs. - useful as glycoside hydrolase inhibitors

摘要

Amino sugar derivs. of formula (I) are new. In the formula m = 0-8, n = 0-8, m+n = 0-8, X is OR, SH, SR, NH2, NHR or NRR1, R is opt. substd. alkylalkenyl, cycloalkyl, aralkyl, aryl or heterocyclyl, R1 is opt. substd. alkyl, cycloalkyl, aralkyl or aryl, or NRR1 is a heterocycle. Cpds. (I) are glycoside hydrolase inhibitors with higher activity than the corresp. cpds. where X = OH. They inhibit starch and sugar metabolism in vivo and are thus useful for treating diabetes, corpulence, hyperlipaemia, dental caries etc. They can also be used as animal feed additives, reducing the ratio of fat to lean meat and improving protein utilisation. In an example, (I, m = 0, n = 1, X = p-nitrophenoxy) was prepd. from dodeca-0-acetyl-0- 4,6-dideoxy-4- 1S-(1,4,6/5)-4,5,6-trihydroxy-3- -hydroxymethylcyclohex-2-en-1-ylamino -alpha-D-glucopyranosyl -(1 right arrow 4)-O-alpha-D-glucopyranosyl-(1 right arrow 4)-alpha-D-glucopyranosyl bromide and p-nitrophenol.