US4435327A
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3β,7β,15α-Trihydroxy-5-androsten-17-one, its 3,15-dipivalate, and their preparation
Assignee: Bayer Pharma AG
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Filing: 1982-09-21
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Granted: 1984-03-06
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Expires: 2002-09-21
Abstract
Abstract A process for the preparation of 3β,7β,15α-trihydroxy-5-androsten-17-one and the 3,15-dipivalate thereof comprises epimerizing 3β,7α,15α-trihydroxy-5-androsten-17-one in the presence of a ketone with or without a solvent, with dilute mineral acid and subsequent treatment with an organic base, and optionally subsequently esterifying the 3β- and 15α-positions of the resultant 3β,7β,15α-triol with a reactive derivative of pivalic acid.
Inventors
- 👤 Karl Petzoldt
- 👤 Henry Laurent
- 👤 Rudolf Wiechert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 00:35
CPC Classifications
C; C12; C12P; C12P33/00; C12P33/12; A; A61; A61P; A61P5/00; A61P5/38; C07; C07J; C07J1/00; C07J1/0003; C07J1/0011; C07J53/00; C07J53/002; C07J53/004; C07J53/008; C07J71/00; C07J71/0005; C07J71/001; C12P33/06
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
34 words
A process for preparing 3β,7β,15α-trihydroxy-5-androsten-17-one, comprising acidifying 3β,7β,15α-trihydroxy-5-androsten-17-one with a dilute mineral acid or dilute strong organic acid in the presence of a ketone, and, then, reacting the resultant product with and organic base.
Claim 2
Dependent Claim
34 words
A process for preparing 3β,7β,15α-trihydroxy-5-androsten-17-one, comprising acidifying 3β,7β,15α-trihydroxy-5-androsten-17-one with a dilute mineral acid or dilute strong organic acid in the presence of a ketone, and, then, reacting the resultant product with and organic base.
Claim 3
Dependent Claim
16 words
A process of claim 1 wherein the acidification is conducted in the presence of a solvent.
Claim 4
Dependent Claim
26 words
A process of claim 1 wherein the acid is sulfuric acid, perchloric acid, hydrochloric acid, p-toluenesulfonic acid or trifluoroacetic acetic acid of 10-50 vol. % strength.
Claim 5
Dependent Claim
41 words
A process of claim 1 or 3 wherein the ketone is aliphatic and contains up to 6 carbon atoms and is contained in the reaction medium in an amount of 10-100 molar equivalents based on the amount of starting material employed.
Claim 6
Dependent Claim
12 words
A process of claim 1 or 3 wherein the base is pyridine.
Claim 7
Dependent Claim
10 words
A process of claim 4 wherein the base is pyridine.
Claim 8
Dependent Claim
32 words
A process of claim 1 for preparing the 3,15-dipivalate of the resultant 3β,7β,15α-triol, comprising esterifying the resultant 3β,7β, 15α-triol in the 3β- and 15α-positions with pivalic acid or a reactive derivative thereof.
Claim 9
Dependent Claim
30 words
A process of claim 3 wherein the acidification is conducted at 0°-50° C. for 1-24 hours and the subsequent treatment with base is conducted at 5°-50° C. for 2-48 hours.
Claim 10
Dependent Claim
30 words
A process of claim 4 wherein the acidification is conducted at 0°-50° C. for 1-24 hours and the subsequent treatment with base is conducted at 5°-50° C. for 2-48 hours.
Claim 11
Dependent Claim
39 words
A process for epimerizing an allyl-positioned 7α-hydroxy or 7α-o-acetoxy group in a Δ 5 -steroid to the corresponding 7β-group, comprising treating the 7α-steroid with a dilute mineral acid or dilute strong organic acid in the presence of a ketone.
Claim 12
Dependent Claim
39 words
A process for epimerizing an allyl-positioned 7α-hydroxy or 7α-o-acetoxy group in a Δ 5 -steroid to the corresponding 7β-group, comprising treating the 7α-steroid with a dilute mineral acid or dilute strong organic acid in the presence of a ketone.
Claim 13
Dependent Claim
17 words
A process of claim 10 further comprising adding a base to the product of said treatment step.
Claim 14
Dependent Claim
1 words
3β,7β,15α-Trihydroxy-5-androsten-17-one.
Claim 15
Dependent Claim
1 words
3β,7β,15α-Trihydroxy-5-androsten-17-one.
Claim 16
Dependent Claim
1 words
3β,15α-Dipivaloyoxy-7β-hydroxy-5-androsten-17-one.
Claim 17
Dependent Claim
1 words
3β,15α-Dipivaloyoxy-7β-hydroxy-5-androsten-17-one.
Claim 18
Dependent Claim
43 words
In a process for preparing 6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone from 7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one, the improvement wherein the latter compound is prepared by, carrying out the process of claim 7 in order to prepare the 3,15-dipivalate of 3β,7β,15α-trihydroxy-5-androsten-17-one, and methylenating the 15β,16β-position in the resultant compound to form 7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one.
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) | 1987-03-06 | 1987-09-05 | 1988-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-06 | 1991-09-05 | 1992-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-06 | 1995-09-05 | 1996-03-06 | $7700.00 | Window Closed / Lapsed |