14,15-beta-epoxycardenolides

Abstract

Abstract 14,15B-EPOXYCARDENOLIDES OF THE FORMULA 14,15-(-O-),17-(2-(O=)-2,5-DIHYDROFUR-4-YL)-ANDROSTANE WHERE C3 IS X WHEREIN C4 . . . C5 IS A SATURATED OR UNSATURATED CARBONCARBON BOND OR IS -C4<(-O-C5(-))AND WHEREIN X IS -CO-, -CH(-O-R)-, OR -CH(-O-R)- AND WHEREIN R IS HYDROGEN, ACYL, ALKYL, A TETRAHYDROPYRANYL RESIDUE OR A SUBSTITUTED TETRAHYDROPYRANYL RESIDUE. THE COMPOUNDS ARE MADE FROM THE CORRESPONDING STEROIDS WHICH, HOWEVER, HAVE AN UNSATURATED CARBONCARBON BOND IN THE 14,15-POSITION, WHICH BOND IS SUBJECTED TO EPOXIDATION. IF THERE IS A CARBON-CARBON DOUBLE BOND ALSO IN THE 4,5-POSITION, THIS BOND MAY BE REDUCED OR LIKEWISE EPOXIDIZED. A KETONE GROUP PRESENT IN THE MOLECLUE MAY BE REDUCED TO HYDROXYL OR A FREE 3-HYDROXYL GROUP MAY BE ACYLATED OR ACETALIZED OR ESTERFIED OR OXIDIZED TO A KETO GROUP. IF THE 3-HYDROXYL GROUP IS ESTERIFIED, ACETALIZED OR ETHERIFIED, IT MAY BE CONVERTED TO A FREE HYDROXYL GROUP. THE DRUGS ARE USEFUL AS HEART DRUGS OF A HIGH DEGREE OF ACTIVITY WITH COMPARATIVELY LOW TOXICITY AND IN PARTICULAR A DESIRABLY BROAD SPAN BETWEEN EFFECTIVE DOSE AND TOXIC DOSE.

Inventors

• 👤 H Lehmann
• 👤 G Zollner

Bibliographic Details