FORFARANDE FOR FRAMSTELLNING AV KARDENOLID-3-(2',3-DEDESOXI-2,'3'-OXIDO-GLYKOSIDER)

1323775 Cardial glycosides FARBWERKE HOECHST AG 1 Sept 1970 [29 Aug 1969(2)] 41722/70 Heading C2U The invention comprises compounds of formula where R is a steroid 3-yl radical of the 20(22)- cardenolide or 20,22-bufadienolide series; the two symbols R1 together represent an epoxy group, or, when R is a cardenolide radical, they each may alternatively represent a hydrogen atom; R2 is H or an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbyl or acyl group; and R3 is H, Me or CH 2 OR2. Preparation of compounds (I) is from compounds of formula by catalytic hydrogenation (for products wherein R1 = H) or by reaction with an organic peracid (for products wherein R1+R1 = epoxy). Subsequently any 41-acyloxy group may be hydrolysed, or any 41-hydroxy group esterified or etherified. Digitoxigenin 3 - (#2 - 2,3 - dideoxy - 4 - O- acetyl - D - arabinoside) is prepared by reacting digitoxigenin with di-O-acetyl-D-arabinal. The L-arabinoside isomer is prepared analogously and then hydrolysed to digitoxigenin 3-(#2- 2,3-dideoxy-L-arabinoside). Uzarigenin 3 - (#2 - 2,3 - dideoxy - 4 - O- acetyl-α-L-rhamnoside) is prepared by reacting uzarigenin with di-O-acetyl-L-rhamnal. Other starting materials of Formula II are prepared as described in Specfications 1,268,230, 1,282,019 and 1,323,148. The steroids of Formula (I) are stated to possess cardiotonic, diuretic and antidiarrhoeal activities, and may be made up with carriers into pharmaceutical compositions for oral or parenteral administration.