Wisconsin Alumni Research Foundation

Joseph K Wichmann

Hector Floyd Deluca

Heinrich K Schnoes

Yoko Tanaka

Herbert E Paaren

Mary A Fivizzani

A novel vitamin D.sub.3 compound, 23-dehydro-25-hydroxyvitamin D.sub.3, and hydroxy-protected derivatives thereof are provided. The new compound is a side-chain-desaturated analog of 25-hydroxycholecalciferol, and would find application as a substitute for such compound or for vitamin D.sub.3.

23-Dehydro-25-hydroxyvitamin D.sub.3

A novel side chain trihydroxylated vitamin D.sub.3 compound, namely 23,24,25-trihydroxyvitamin D.sub.3 and its acylated and alkylsilyated derivatives are provided. The new compounds are hydroxy analogs of the biologically-active 25-hydroxyvitamin D.sub.3 and would find application as substitutes for such compound or for vitamin D.sub.3.

Trihydroxyvitamin D.sub.3 compounds

The invention provides methods for preparing the various isomeric forms of 25-hydroxyvitamin D.sub.3 -26,23-lactone utilizing cyanohydrin formation with readily prepared steroid materials followed by actinic radiation of the products and recovery of the desired 25-hydroxyvitamin D.sub.3 -26,23-lactone. The invention also provides new intermediate compounds in their various isomeric forms derived during the process for preparing the said vitamin D.sub.3 lactones. 25-Hydroxyvitamin D.sub.3 -26,23-lactone is recognized as having vitamin D-like activity and is believed to play an important role in the regulation of calcium and phosphate levels in the animal and human organism. The present invention provides a convenient method for preparing the various isomeric forms of this compound.

Process for preparing vitamin D-lactones

The invention provides a new vitamin D compound, 1.alpha.,25-dihydroxy-vitamin D.sub.3 26,23-lactone. The compound is characterized by vitamin D-like activity.

Vitamin D-lactone derivative and process for preparing same

23,25-Dihydroxyvitamin D.sub.3 a new derivative of vitamin D.sub.3. The compound is the 23-hydroxylated analog of biologically potent 23-hydroxycholecalciferol and by virtue of such structural similarity should find application as a substitute for such compound or for vitamin D.sub.3.

23,25-Dihydroxyvitamin D.sub.3

The invention provides a new derivative of vitamin D, 25-hydroxycholecalciferol-26,23-lactone. The compound is characterized by vitamin D-like activity in its ability to increase serum calcium concentration by mobilizing bone and would find application in disease states requiring the elevation of serum calcium concentration.

Growing community of inventors

Madison, WI, United States of America

Joseph K Wichmann