US4183852A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing 25-hydroxycholesterol
Assignee: Individual
•
Filing: 1977-07-18
•
Granted: 1980-01-15
•
Expires: 1997-07-18
Abstract
Abstract The synthesis of 25-hydroxycholesterol and 25-hydroxycholecalciferol from animal bile starting materials in which hyodeoxycholic acid or an ester thereof is converted to the 3β-hydroxy-5-cholenic acid alkyl ester, and this is converted to 3β-hydroxy-25-cyano-5-cholene by a series of steps by which the sterol nucleus is stabilized by placing a protecting group at the 3 position and then extending the chain from the carbon at the 24 position to a cyanide group at the 25 position. The compound so formed is subjected to a series of reactions by which it is transformed into 25-hydroxy-7-dehydrocholesterol which may then be irradiated with ultraviolet light to 25-hydroxycholecalciferol. The invention discloses new and improved processes for preparing these end products and also new compounds formed as intermediates and processes for preparing these intermediates.
Inventors
- 👤 Emil T. Kaiser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:37
CPC Classifications
C; C07; C07J; C07J17/00; C07J31/00; C07J31/006; C07J41/00; C07J41/0033; C07J41/0094; C07J9/00; C07J9/005; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
12 words
A steroid compound having the structure ##STR23## in which P is β-methoxyethoxymethyl.
Claim 2
Dependent Claim
12 words
A steroid compound having the structure ##STR23## in which P is β-methoxyethoxymethyl.
Claim 3
Dependent Claim
16 words
A steroid compound having the structure ##STR24## in which P is β-methoxyethoxymethyl and Ts is p-toluenesulfonyl.
Claim 4
Dependent Claim
16 words
A steroid compound having the structure ##STR24## in which P is β-methoxyethoxymethyl and Ts is p-toluenesulfonyl.
Claim 5
Dependent Claim
18 words
A steroid compound having the structure ##STR25## where X is chlorine, bromine or iodine and P is β-methoxyethoxymethyl.
Claim 6
Dependent Claim
18 words
A steroid compound having the structure ##STR25## where X is chlorine, bromine or iodine and P is β-methoxyethoxymethyl.
Claim 7
Dependent Claim
13 words
A steroid compound having the structure ##STR26## where P is 2-tetrahydropyranyl or β-methoxyethoxymethyl.
Claim 8
Dependent Claim
13 words
A steroid compound having the structure ##STR26## where P is 2-tetrahydropyranyl or β-methoxyethoxymethyl.
Claim 9
Dependent Claim
14 words
A steroid compound as set forth in claim 4 in which P is 2-tetrahydropyranyl.
Claim 10
Dependent Claim
14 words
A steroid compound as set forth in claim 4 in which P is β-methoxyethoxymethyl.
Claim 11
Dependent Claim
7 words
A steroid compound having the structure ##STR27##
Claim 12
Dependent Claim
7 words
A steroid compound having the structure ##STR27##
Claim 13
Dependent Claim
32 words
In a process for preparing 25-hydroxycholesterol, the step of refluxing ##STR28## in aqueous alcohol with p-toluenesulfonic acid for a period until the reaction is complete to prepare ##STR29## where P is tetrahydropyranyl.
Claim 14
Dependent Claim
32 words
In a process for preparing 25-hydroxycholesterol, the step of refluxing ##STR28## in aqueous alcohol with p-toluenesulfonic acid for a period until the reaction is complete to prepare ##STR29## where P is tetrahydropyranyl.
Claim 15
Dependent Claim
27 words
In a process for preparing 25-hydroxycholesterol, the step of mixing ##STR30## where P is β-methoxyethoxymethyl, with solid zinc bromide in methylene chloride to remove the β-methoxyethoxymethyl group.
Claim 16
Dependent Claim
27 words
In a process for preparing 25-hydroxycholesterol, the step of mixing ##STR30## where P is β-methoxyethoxymethyl, with solid zinc bromide in methylene chloride to remove the β-methoxyethoxymethyl group.
Claim 17
Dependent Claim
46 words
for preparing 25-hydroxycholesterol, the step of heating with a metal cyanide ##STR31## where P is a heterocyclic group having the pyran nucleus or a lower alkyl group or the β-methoxyethoxymethyl group and where Ts is the p-toluenesulfonyl group, in dimethyformamide to prepare the compound ##STR32## .
Claim 18
Dependent Claim
46 words
for preparing 25-hydroxycholesterol, the step of heating with a metal cyanide ##STR31## where P is a heterocyclic group having the pyran nucleus or a lower alkyl group or the β-methoxyethoxymethyl group and where Ts is the p-toluenesulfonyl group, in dimethyformamide to prepare the compound ##STR32## .
References Cited (Backward Citations)
US3257384A
Cited
US3833622A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-14 | 1983-07-16 | 1984-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-14 | 1987-07-16 | 1988-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-14 | 1991-07-16 | 1992-01-15 | $7700.00 | Window Closed / Lapsed |