26,26,26,27,27,27-Hexafluoro-1.alpha.,25-dihydroxycholecalciferol and process for preparing same
AssigneeWisconsin Alumni Research Foundation
InventorsHector F. DeLuca, Yoko Tanaka, Nobuo Ikekawa, Yoshiro Kobayashi
Life of this patent
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Abstract
This invention provides a new derivative of vitamin D, 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholecalciferol, a process for preparing the same, and novel intermediate compounds. The compound is characterized by vitamin D-like activity substantially greater than that exhibited by 1.alpha.,25-dihydroxycholecalciferol which is considered to be the active hormonal form of vitamin D. The compound would find ready application as a substitute for vitamin D and in the treatment of or prophylaxis for disease states evincing metabolic calcium and phosphorous deficiences or imbalances.
Claims9
Compounds having the formula ##STR2## wherein R R.sub.1 and R.sub.2 are selected from hydrogen or acyl having from 1 to about 4 carbon atoms.
26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholesterol.
26,26,26,27,27,27-hexafluoro-25-hydroxycholest-1,4-trien-3-one.
26,26,26,27,27,27-hexafluoro-25-hydroxy-1.alpha.,2.alpha.-epoxy cholest-4,6-dien-3-one.
26,26,26,27,27,27-he xafluoro-1.alpha.,3.beta.,25-trihydroxycholest-5,7-dien.
A method for preparing 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholecalciferol which comprises
- hydrolyzing 26,26,26,27,27,27-hexafluoro-25-hydroxycholesterol-3-tetrahydropyranyl ether
- oxidizing the resulting 26,26,26,27,27,27-hexafluoro-25-hydroxycholesterol
- treating the resulting 26,26,26,27,27,27-hexafluoro-25-hydroxycholest-1,4,6-trien-3-one with hydrogen peroxide to obtain 26,26,26,27,27,27-hexafluoro-25-hydroxy-1.alpha.,2.alpha.-epoxycholest-4,6 -dien-3-one
- reducing the said 1,2-epoxide with an alkali or alkaline earth metal in liquid ammonia or amine solvent to obtain 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholesterol
- acetylating said 1.alpha.,25-dihydroxycholesterol to 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholesterol triacetate
- converting said triacetate to 26,26,26,27,27,27-hexafluoro-1.alpha.,3.beta.,25-triacetoxycholest-5,7-die ne
- exposing said diene successively to ultraviolet radiation and thermal isomerization to obtain 26,26,26,27,27,27-hexafluoro-1.alpha.,25-dihydroxycholecalciferol triacetate
- hydrolyzing the said cholecalciferol triacetate to obtain 26,26,26,27,27,27-hexafluoro 1.alpha.,25-dihydroxycholecalciferol.
Dependencies are inferred from the claim text.