1-Substituted glycopyranosides
AssigneeMerck & Co., Inc.
InventorsMitree M. Ponpipom, Robert L. Bugianesi, Philippe L. Durette, Howard M. Katzen, Tsung-Ying Shen
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Abstract
The invention disclosed herein relates to novel 1-deoxy-glycopyranosides, preferably 1-deoxy-D-mannopyranosides, having in the 1-position of the pyranoside ring an .omega.-aminoalkylthio, .omega.-aminoalkyloxy or .omega.-aminoalkanoylamino substituent; and to novel processes for preparing these 1-substituted-1-deoxy-glycopyranosides starting with the corresponding tetra-O-acetyl-glycopyranosyl bromide or amine. These .omega.-amino(alkylthio, alkyloxy or alkanoylamino)-1-deoxy-glycopyranosides, and in particular 1-[(6'-aminohexyl)thio or oxy]-1-deoxy-D-mannopyranosides, possess insulin-like activity.
Claims5
A hypoglycemic compound selected from the group consisting of 1-[(.omega.-aminoalkyl)thio]-1-deoxy-glycopyranosides and 1-[(.omega.-aminoalkanoyl)amino]-1-deoxy-glycopyranosides, wherein said alkyl contains 2 to 8 carbon atoms and said alkanoyl contains 3 to 9 carbon atoms.
Dependencies are inferred from the claim text.