Carbaxylosides of 4-ethyl-2-oxo-2H-benzopyran-7-yl as non-hydrolyzable, orally active venous antithrombotic agents

A (−)-conduritol F derivative was condensed with 4-ethyl-7-hydroxy-2H-1-benzopyran-2-one and converted into (+)-4-ethyl-7-[(1′R,2′S,3′S,4′R)-2′,3′,4′-trihydroxycyclohexyloxy]-2H-1-benzopyran-2-one ((+)− 2). Enantiomer (−)− 2 was obtained from a (+)-conduritol F derivative. The carbaxyloside (−)− 2 with the L-xylose configuration was more active than (+)− 2 in the Wessler's model. The carba-L-xyloside (−)- 2 is more active than its enantiomer (+)- 2 in the venous Wessler's model