§
Luxuse
Patent Intelligence
Sign In
← Back to Patent Explorer
US4134904A Expired / Lapsed US ⏱️ 0.0 years remaining

Synthesis of steroids

Assignee: Individual
•
Filing: 1977-08-30
•
Granted: 1979-01-16
•
Expires: 1997-08-30
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The synthesis of 25-hydroxycholesterol from animal bile starting materials in which hyodeoxychloic acid or an ester thereof is converted to the 3β-hydroxy-5-cholenic acid alkyl ester, and then converted to 3β-hydroxy-25-cyano-5-cholene by a series of steps in which the sterol nucleus is stablized by use of a 3α,5α-bridge sometimes called an i-steroid configuration, and the carbon chain then extended 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 the 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 22:31
CPC Classifications
C; C07; C07J; C07J9/00; C07J31/00; C07J31/006; C07J41/00; C07J41/0033; C07J41/0094; C07J53/00

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 13 words
A steroid compound having the structure ##STR16## where P is an alkyl group.
Claim 2
Dependent Claim 13 words
A steroid compound having the structure ##STR16## where P is an alkyl group.
Claim 3
Dependent Claim 13 words
A steroid compound as set forth in claim 1 where P is methyl.
Claim 4
Dependent Claim 52 words
In a process for preparing 25-hydroxycholesterol the step of heating with a metal cyanide a compound having the structure: ##STR17## where P is an alkyl group and Q is an alkyl sulfonyl or aryl sulfonyl group, in dimethylformamide to obtain the compound having the structure: ##STR18## where P is an alkyl group.
Claim 5
Dependent Claim 52 words
In a process for preparing 25-hydroxycholesterol the step of heating with a metal cyanide a compound having the structure: ##STR17## where P is an alkyl group and Q is an alkyl sulfonyl or aryl sulfonyl group, in dimethylformamide to obtain the compound having the structure: ##STR18## where P is an alkyl group.
Claim 6
Dependent Claim 20 words
A process as set forth in claim 3 wherein P is a methyl group and Q is a p-toluenesulfonyl group.
Claim 7
Dependent Claim 41 words
In a process for preparing 25-hydroxycholesterol the step of heating a compound having the structure ##STR19## in aqueous alcohol, dioxane or tetrahydrofuran, containing p-toluenesulfonic acid, for a period until the reaction is complete, to obtain a compound having the structure ##STR20##
Claim 8
Dependent Claim 41 words
In a process for preparing 25-hydroxycholesterol the step of heating a compound having the structure ##STR19## in aqueous alcohol, dioxane or tetrahydrofuran, containing p-toluenesulfonic acid, for a period until the reaction is complete, to obtain a compound having the structure ##STR20##
Claim 9
Dependent Claim 30 words
In a process for preparing 25-hydroxycholesterol the step of heating a compound having the structure ##STR21## with a metal cyanide in dimethylformamide to obtain a compound having the structure ##STR22##
Claim 10
Dependent Claim 30 words
In a process for preparing 25-hydroxycholesterol the step of heating a compound having the structure ##STR21## with a metal cyanide in dimethylformamide to obtain a compound having the structure ##STR22##
Claim 11
Dependent Claim 44 words
A process as set forth in claim 6 including the step of heating the compound having the following structure: ##STR23## with a water-dioxane mixture containing p-toluenesulfonic acid for a period to complete the reaction and to obtain a compound having the following structure: ##STR24##

References Cited (Backward Citations)

US3152152A Cited
US3257384A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-01-15 1982-07-17 1983-01-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-01-15 1986-07-17 1987-01-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-01-15 1990-07-17 1991-01-16 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag