US4336193A
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Process for preparing vitamin D-lactones
Assignee: Wisconsin Alumni Research Foundation
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Filing: 1981-01-26
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Granted: 1982-06-22
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Expires: 2001-01-26
Abstract
Abstract The invention provides methods for preparing the various isomeric forms of 25-hydroxyvitamin D 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 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 3 lactones. 25-Hydroxyvitamin D 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.
Inventors
- 👤 Hector F. DeLuca
- 👤 Heinrich K. Schnoes
- 👤 Herbert E. Paaren
- 👤 Joseph K. Wichmann
- 👤 Mary A. Fivizzani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:44
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/26; C07D307/30; C07D307/32; C07D307/33; A; A61; A61P; A61P3/00; A61P3/02; A61P3/12; A61P3/14; A61P43/00; C07J; C07J17/00; C07J9/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
65 words
A process for preparing 25-hydroxyvitamin D 3 -26,23-lactone, which comprises subjecting 3β,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 3β,25-hydroxy-cholesta-5,7-diene-26,23-lactone, subjecting said lactone to actinic irradiation to obtain 25-hydroxy-previtamin D 3 -26,23-lactone, and isomerizing said product by heating and recovering the desired 25-hydroxyvitamin D 3 -26,23-lactone product.
Claim 2
Dependent Claim
65 words
A process for preparing 25-hydroxyvitamin D 3 -26,23-lactone, which comprises subjecting 3β,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 3β,25-hydroxy-cholesta-5,7-diene-26,23-lactone, subjecting said lactone to actinic irradiation to obtain 25-hydroxy-previtamin D 3 -26,23-lactone, and isomerizing said product by heating and recovering the desired 25-hydroxyvitamin D 3 -26,23-lactone product.
Claim 3
Dependent Claim
43 words
Compounds having the formula ##STR11## where X is selected from ##STR12## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropryanyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 4
Dependent Claim
43 words
Compounds having the formula ##STR11## where X is selected from ##STR12## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropryanyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 5
Dependent Claim
42 words
Compounds according to claim 2 wherein X is ##STR13## and each of R 1 and R 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.
Claim 6
Dependent Claim
26 words
Compounds according to claim 2 where X is ##STR14## R 1 , R 2 and R 3 are hydrogen, and R 4 is hydrogen or alkyl.
Claim 7
Dependent Claim
20 words
The compounds of claim 2 wherein X is ##STR15## and R 1 is selected from hydrogen, acyl, alkylsilyl and tetrahydropyranyl.
Claim 8
Dependent Claim
43 words
Compounds having the formula ##STR16## where X is selected from ##STR17## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 9
Dependent Claim
43 words
Compounds having the formula ##STR16## where X is selected from ##STR17## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 10
Dependent Claim
42 words
Compounds according to claim 6 wherein X is ##STR18## and each of R 1 and R 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.
Claim 11
Dependent Claim
23 words
Compounds according to claim 6 wherein X is ##STR19## and R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 12
Dependent Claim
20 words
The compounds of claim 6 wherein X is ##STR20## and R 1 is selected from hydrogen, acyl, alkylsilyl and tetrahydropyranyl.
Claim 13
Dependent Claim
43 words
Compounds having the formula ##STR21## where X is selected from ##STR22## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 14
Dependent Claim
43 words
Compounds having the formula ##STR21## where X is selected from ##STR22## R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl in all their isomeric forms.
Claim 15
Dependent Claim
42 words
Compounds according to claim 10 wherein X is ##STR23## and each of R 1 and R 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.
Claim 16
Dependent Claim
26 words
Compounds according to claim 10 wherein X is ##STR24## R 1 , R 2 and R 3 are hydrogen and R 4 is hydrogen or alkyl.
Claim 17
Dependent Claim
67 words
The compounds having the formula ##STR25## wherein each of R 1 and R 2 , which may be the same or different, is selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl, except that, when the stereochemical configuration at carbon-23 and 25 is as it occurs in 25-hydroxyvitamin D 3 -26,23-lactone derived from natural sources, R 1 and R 2 may not both be hydrogen.
Claim 18
Dependent Claim
67 words
The compounds having the formula ##STR25## wherein each of R 1 and R 2 , which may be the same or different, is selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl, except that, when the stereochemical configuration at carbon-23 and 25 is as it occurs in 25-hydroxyvitamin D 3 -26,23-lactone derived from natural sources, R 1 and R 2 may not both be hydrogen.
Claim 19
Dependent Claim
33 words
Compounds having the formula ##STR26## where R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl.
Claim 20
Dependent Claim
33 words
Compounds having the formula ##STR26## where R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, acyl, alkylsilyl and tetrahydropyranyl and R 4 is hydrogen or alkyl.
Claim 21
Dependent Claim
19 words
The compounds of claim 14 wherein R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 22
Dependent Claim
21 words
The compounds of claim 14 wherein R 1 , R 2 and R 3 are hydrogen and R 4 is alkyl.
References Cited (Backward Citations)
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