1.alpha.,24-dihydroxycholecalciferols, novel precursors...

Details 1.alpha.,24-dihydroxycholecalciferols, novel precursors... 1.alpha.,24-dihydroxycholecalciferols, novel precursors...

C - Chemistry, Metallurgy

07

C

260/645, 204/91.

C07C 35/21 (2006.01) A23K 1/16 (2006.01) C07C 43/18 (2006.01) C07J 9/00 (2006.01) C07J 71/00 (2006.01)

Patent

CA 1051442

ABSTRACT Novel 1.alpha., 24-dihydroxycholecalciferol and derivatives thereof which are useful with reduced side-effects for the treat- ment of abnormal metabolism of calcium and phosphorus caused by liver failure, renal failure, gastrointestinal tract failure and parathyroid failure, and related bone diseases. Preparation of the novel 1.alpha. , 24-dihydroxycholecalciferol and their derivatives starts from 1.alpha. , 24-dihydroxycholesterol prepared by reacting 1.alpha. , 2.alpha. -epoxy-24-keto-cholesta-4,6-dien-3-one with an alkali metal and a proton donor in the presence of liquid ammonia or a liquid amine. Reaction of the 1.alpha. , 24-dihydroxycholesterol with an allylic bromina- ting agent, followed by contacting with a dehydrobrominating agent, affords 1.alpha. , 3.beta. , 24-trihydroxycholesta-5,7-diene derivative, which can then be converted to 1.alpha., 24-dihydroxycholocalciferol by ultra- violet irradiation in an organic solvent, followed by isomerization. Processes are also provided for separating 1.alpha., 24-dihydroxychole- sterol into an (S)-epimer and an (R)-epimer, and also for separating at least one of 1.alpha., 3.beta., 24(S)- and 1.alpha., 3.beta., 24(R)-trihydroxycholesta- 5,7-dienes fromtrihydroxycholesta-4,6-diene. .

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