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Process for the separation of 4-androsten-3,17-dione and 1,4-androstadien-3,17-dione

Assignee: Jenapharm GmbH and Co KG
•
Filing: 1983-03-10
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Granted: 1984-10-02
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Expires: 2003-03-10
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Abstract

Abstract A process is disclosed for the separation of 4-androsten-3,17-dione/1,4-androstadien-3,17-dione mixtures, which are produced, e.g., upon microbiological sterol-side chain decomposition, through conversion of said mixture into a mixture of 17β-cyano-17α-hydroxy-4-androsten-3-one/17β-cyano-17.alpha.-hydroxy-1,4-androstadien-3-one, from which the difficultly soluble 17β-cyano-17α-hydroxy-4-androsten-3-one is separated in crystalline form through filtration, and the 17β-cyano-17α-hydroxy-1,4-androstadiene remaining in the mother liquor is re-split, directly or after extraction with organic solvent, by treatment in alkaline medium, into 1,4-androstadien-3,17-dione, and isolated as such. The separation of the products follows in high yields, and in sufficient purity for further working-up in the synthesis of androstane and pregnane derivatives, as well as estratrienes.

Inventors

  • 👤 Gerhard Teichmuller
  • 👤 Joachim Rabe
  • 👤 Harry Henkel

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 21:11
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0003; C07J1/0011; C07J41/00; C07J41/0033; C07J41/0094

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 37 words
Process for the separation of 4-androsten-3,17-dione and 1,4-androstadien-3,17-dione mixtures, comprising reacting said 4-androsten-3,17-dione/1,4-androstadiene-3,17-dione mixture with HCN-yielding cyanide compound, into a mixture of 17β-cyano-17α-hydroxy-4-androsten-3-one and 17β-cyano-17α-hydroxy-1,4-androstadien-3-one, and separating from said product mixture the difficultly soluble 17β-cyano-17α-hydroxy-4-androsten-3-one through crystallization.
Claim 2
Dependent Claim 37 words
Process for the separation of 4-androsten-3,17-dione and 1,4-androstadien-3,17-dione mixtures, comprising reacting said 4-androsten-3,17-dione/1,4-androstadiene-3,17-dione mixture with HCN-yielding cyanide compound, into a mixture of 17β-cyano-17α-hydroxy-4-androsten-3-one and 17β-cyano-17α-hydroxy-1,4-androstadien-3-one, and separating from said product mixture the difficultly soluble 17β-cyano-17α-hydroxy-4-androsten-3-one through crystallization.
Claim 3
Dependent Claim 12 words
Process according to claim 1, further comprising re-splitting said 17β-cyano-17α-hydroxy-4-androsten-3-one into 4-androsten-3,17-dione.
Claim 4
Dependent Claim 29 words
Process according to claim 2, further comprising re-splitting the 17β-cyano-17α-hydroxy-1,4-androstadien-3-one remaining in said product solution, directly or after extraction with organic solvent into 1,4-androstadien-3,17-dione, and then isolating the same.
Claim 5
Dependent Claim 21 words
Process according to claim 1, wherein said HCN-yielding cyanide compound is selected from the group consisting of acetoncyanohydrine and alkali cyanide.
Claim 6
Dependent Claim 17 words
Process according to claim 2, wherein said re-splitting is performed by heating in alkaline solutions of alcohol.
Claim 7
Dependent Claim 19 words
Process according to claim 3, wherein said re-splitting of 17β-cyano-17α-hydroxy-1,4-androstaden-3-one is performed by heating in alkaline solutions of alcohol.

References Cited (Backward Citations)

US4144254A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-10-02 1988-04-02 1988-10-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-10-02 1992-04-02 1992-10-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-10-02 1996-04-02 1996-10-02 $7700.00 Window Closed / Lapsed

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