US4267117A
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US
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Compounds and process
Assignee: Pharmacia and Upjohn Co
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Filing: 1979-06-14
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Granted: 1981-05-12
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Expires: 1999-06-14
Abstract
Abstract A process for preparing 1 alpha -hydroxylated calciferols is described. Intermediates used in the process are also provided.
Inventors
- 👤 William G. Salmond
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 21:48
CPC Classifications
C; C07; C07C; C07C401/00; C07C2601/00; C07C2601/12; C07C2601/14; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/24
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
190 words
A compound selected from the group consisting of compounds having the formula ##STR132## wherein R 1 is selected from the group consisting of hydrogen, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl wherein the aryl group is phenyl or substituted by a lower alkyl, lower alkoxy, halogen, nitro or a cyano group; R 2 is selected from the group consisting of ##STR133## wherein R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive and aryloxy; R 4 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, t-butyldimethylsilyloxy, phenyldimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, benzoyl, substituted benzoyl; and wherein R 3 and R 4 when taken together form a group selected from the group consisting of acetonide, carbonate and thiocarbonate; ##STR134## wherein R 5 is selected from the group consisting of hydrogen, methyl hydroxyl and lower alkoxyl of from 1 to 5 carbon atoms, inclusive; with the proviso that when R 2 is the group ##STR135## and R 3 is hydrogen or hydroxy R 1 cannot be hydrogen or acyloxy.
Claim 2
Dependent Claim
190 words
A compound selected from the group consisting of compounds having the formula ##STR132## wherein R 1 is selected from the group consisting of hydrogen, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl wherein the aryl group is phenyl or substituted by a lower alkyl, lower alkoxy, halogen, nitro or a cyano group; R 2 is selected from the group consisting of ##STR133## wherein R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive and aryloxy; R 4 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, t-butyldimethylsilyloxy, phenyldimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, benzoyl, substituted benzoyl; and wherein R 3 and R 4 when taken together form a group selected from the group consisting of acetonide, carbonate and thiocarbonate; ##STR134## wherein R 5 is selected from the group consisting of hydrogen, methyl hydroxyl and lower alkoxyl of from 1 to 5 carbon atoms, inclusive; with the proviso that when R 2 is the group ##STR135## and R 3 is hydrogen or hydroxy R 1 cannot be hydrogen or acyloxy.
Claim 3
Dependent Claim
31 words
Compounds according to claim 1 wherein R 2 is selected from the group consisting ##STR136## wherein R 1 , R 3 and R 4 are the same as in claim 1.
Claim 4
Dependent Claim
68 words
Compounds of claim 2 having the formula ##STR137## wherein R 1 and R 3 are the same as in claim 2, wherein R 1 is selected from the group consisting of hydroge, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl; R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, and aroyloxy.
Claim 5
Dependent Claim
42 words
A compound according to claim 3 wherein R 1 is selected from the group consisting of trimethylsilyl and aroyl and R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy and acyl of from 2 to 6 carbon atoms, inclusive.
Claim 6
Dependent Claim
24 words
A compound according to claim 4 wherein R 1 is benzoate and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1α,3β-diol, 3-benzoate.
Claim 7
Dependent Claim
24 words
A compound according to claim 4 wherein R 1 is trimethylsilyl and R 3 is trimethylsilyloxy so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1α,3β,25-triol, 3,25-bis-trimethylsilylether.
Claim 8
Dependent Claim
25 words
A compound according to claim 4 wherein R 1 is benzoate and R 3 is trimethylsilyloxy so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1α,3β-25-triol, 3-benzoate, 25-trimethylsilylether.
Claim 9
Dependent Claim
24 words
A compound according to claim 4 wherein R 1 is benzoate and R 3 is hydroxy so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1α,3β-25-triol, 3-benzoate.
Claim 10
Dependent Claim
25 words
A compound according to claim 4 wherein R 1 is benzoate and R 3 is acetoxy so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1α,3β-25-triol, 3-benzoate, 25-acetate.
Claim 11
Dependent Claim
76 words
Compounds of claim 2 having the formula ##STR138## wherein R 1 is selected from the group consisting of hydrogen, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl wherein the aryl group is phenyl or phenyl substituted by a lower alkyl, lower alkoxy, halogen, nitro or a cyano group; R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, and aroyloxy.
Claim 12
Dependent Claim
42 words
A compound according to claim 10 wherein R 1 is selected from the group consisting of trimethylsilyl and aroyl and R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy and acyloxy of from 2 to 6 carbon atoms, inclusive.
Claim 13
Dependent Claim
24 words
A compound according to claim 11 wherein R 1 is benzoate and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β-diol, 3-benzoate.
Claim 14
Dependent Claim
23 words
A compound according to claim 11 wherein R 1 is hydrogen and R 3 is hydroxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β,25-triol.
Claim 15
Dependent Claim
23 words
A compound according to claim 11 wherein R 1 is trimethylsilyl and R 3 is trimethylsilyloxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β,25-triol-3,25-bis-trimethylsilylether.
Claim 16
Dependent Claim
25 words
A compound according to claim 11 wherein R 1 is benzoate and R 3 is trimethylsilyloxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β,25-triol, 3-benzoate, 25-trimethylsilylether.
Claim 17
Dependent Claim
24 words
A compound according to claim 11 wherein R 1 is benzoate and R 3 is hydroxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β,25-triol, 3-benzoate.
Claim 18
Dependent Claim
25 words
A compound according to claim 11 wherein R 1 is benzoate and R 3 is acetoxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β-25-triol, 3-benzoate, 25-acetate.
Claim 19
Dependent Claim
77 words
A compound of claim 2 having the formula ##STR139## wherein R 1 is selected from the group consisting of hydrogen, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl wherein the aryl group is phenyl or phenyl substituted by a lower alkyl, lower alkoxy, halogen, nitro or a cyano group; R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, and aroyloxy.
Claim 20
Dependent Claim
42 words
A compound according to claim 18 wherein R 1 is selected from the group consisting of trimethylsilyloxy and aroyl and R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy and acyloxy of from 2 to 6 carbon atoms, inclusive.
Claim 21
Dependent Claim
24 words
A compound according to claim 19 wherein R 1 is benzoate and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5Z,7E,10(19)-triene-1β,3β-diol, 3-benzoate.
Claim 22
Dependent Claim
76 words
A compound of claim 2 having the formula ##STR140## wherein R 1 is selected from the group consisting of hydrogen, trimethylsilyl, t-butyldimethylsilyl, phenyldimethylsilyl, acyl of from 2 to 6 carbon atoms, and aroyl wherein the aryl group is phenyl or phenyl substituted by a lower alkyl, lower alkoxy, halogen, nitro or cyano group; R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy, acyloxy of from 2 to 6 carbon atoms, inclusive, and aroyloxy.
Claim 23
Dependent Claim
42 words
A compound according to claim 21 wherein R 1 is selected from the group consisting of trimethylsilyl and aroyl and R 3 is selected from the group consisting of hydrogen, hydroxy, trimethylsilyloxy and acyl of from 2 to 6 carbon atoms, inclusive.
Claim 24
Dependent Claim
24 words
A compound according to claim 22 wherein R 1 is benzoyl and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1β,3β-diol, 3-benzoate.
Claim 25
Dependent Claim
23 words
A compound according to claim 22 wherein R 1 is benzoyl and R 3 is hydroxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1β,3β,25-triol-3-benzoate.
Claim 26
Dependent Claim
25 words
A compound according to claim 22 wherein R 1 is benzoyl and R 3 is trimethylsilyloxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1β,3β-25-triol, 3-benzoate, 25-trimethylsilylether.
Claim 27
Dependent Claim
25 words
A compound according to claim 22 wherein R 1 is benzoyl and R 3 is acetoxy so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1β,3β-25-triol, 3-benzoate, 25-acetate.
Claim 28
Dependent Claim
23 words
A compound according to claim 11 wherein R 1 is tertiarybutyldimethylsilyl and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1α,3β-diol,3-tertiarybutyldimethylsilylether.
Claim 29
Dependent Claim
24 words
A compound according to claim 22 wherein R 1 is tertiarybutyldimethylsilyl and R 3 is hydrogen so that the specific embodiment is 9,10-secocholesta-5E,7E,10(19)-triene-1β, 3β-diol,3-tertiarybutyldimethylsilylether.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-11 | 1984-11-10 | 1985-05-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-11 | 1988-11-10 | 1989-05-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-11 | 1992-11-10 | 1993-05-12 | $7700.00 | Window Closed / Lapsed |