PURPOSE: To obtain a new GLA-60 analog, an endotoxic copponent of enteric bacteria, showing excellent inhibitory action on macrophage activity as a lipopolysaccharide antagonist, useful as an immunosuppressive agent, a therapeutic agent for autoimmune disease and an anti-febris septica agent.
CONSTITUTION: This new GLA-60 analog is shown by formula I [R1 and R2 are each a 6-20C alkanoyl or a 6-20C alkanoyl substituted with a substituent group comprising a group A of substituent groups; (group A) a halogen, a ketone, hydroxyl group, a 6-20C alkanoyloxy and a 6-20C alkenoyloxy], shows excellent inhibitory action on macrophage activity as a lipopolysaccharide(LPS) antagonist and is useful as an immunosuppressive agent, a therapeutic agent for autoimmune disease such as rheumatics and collagen disease and an anti- febris septica agent. The compound is obtained by cyanating the 1-position of an imidate 1 of formula II (Ac is acetyl), aminating the azide group at the 2-position by reduction, hydrolyzing the cyano group at the 1-position, deprotecting the hydroxyl group at the 3-position and acylating and deprotecting the hydroxyl group at the 4-position and phosphorylating.
UOORESU MATSUKINDOO
KURAKATA SHINICHI
TATSUTA TORU
OGAWA JUNKO
NISHIJIMA MASAHIRO