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Process for preparing vitamin D-lactones
| Details |
Inventors: DeLuca, Hector F.; Schnoes, Heinrich K.; Paaren, Herbert E.; Wichmann, Joseph K.; Fivizzani, Mary A.;
Assignee: Wisconsin Alumni Research Foundation (Madison, WI)
Primary Examiner: Roberts; Elbert L.
Assistant Examiner:
Attorney, Agent or Firm: Bremer; Howard W.
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. |
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DETAILED DESCRIPTION Having thus described the invention what is claimed is: 1.
A process for preparing 25-hydroxyvitamin D.
sub.
3 -26,23-lactone, which comprises subjecting 3.
beta.
,23-dihydroxy-26-norcholesta-5,7-diene-25-one to treatment with an inorganic cyanide or organic cyanohydrin under basic conditions in an alcoholic solvent, followed by treatment with a mineral acid, to obtain 3.
beta.
,25-hydroxy-cholesta-5,7-diene-26,23-lactone, subjecting said lactone to actinic irradiation to obtain 25-hydroxy-previtamin D.
sub.
3 -26,23-lactone, and isomerizing said product by heating and recovering the desired 25-hydroxyvitamin D.
sub.
3 -26,23-lactone product.
2.
Compounds having the formula ##STR11## where X is selected from ##STR12## R.
sub.
1, R.
sub.
2 and R.
sub.
3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropryanyl and R.
sub.
4 is hydrogen or alkyl in all their isomeric forms.
3.
Compounds according to claim 2 wherein X is ##STR13## and each of R.
sub.
1 and R.
sub.
2, which may be the same or different, is selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl in all their isomeric forms.
4.
Compounds according to claim 2 where X is ##STR14## R.
sub.
1, R.
sub.
2 and R.
sub.
3 are hydrogen, and R.
sub.
4 is hydrogen or alkyl.
5.
The compounds of claim 2 wherein X is ##STR15## and R.
sub.
1 is selected from hydrogen, acyl, alkylsilyl and tetrahydropyranyl.
6.
Compounds having the formula ##STR16## where X is selected from ##STR17## R.
sub.
1, R.
sub.
2 and R.
sub.
3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R.
sub.
4 is hydrogen or alkyl in all their isomeric forms.
7.
Compounds according to claim 6 wherein X is ##STR18## and each of R.
sub.
1 and R.
sub.
2, which may be the same or different, is selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl in all their isomeric forms.
8.
Compounds according to claim 6 wherein X is ##STR19## and R.
sub.
1, R.
sub.
2, R.
sub.
3 and R
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Weight Loss and Supplements 
