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DE576967C - Process for the preparation of derivatives of the male sex hormone - Google Patents

Process for the preparation of derivatives of the male sex hormone

Info

Publication number
DE576967C
DE576967C DE1930576967D DE576967DD DE576967C DE 576967 C DE576967 C DE 576967C DE 1930576967 D DE1930576967 D DE 1930576967D DE 576967D D DE576967D D DE 576967DD DE 576967 C DE576967 C DE 576967C
Authority
DE
Germany
Prior art keywords
male sex
derivatives
sex hormone
preparation
hormone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE1930576967D
Other languages
German (de)
Inventor
Dr Max Gehrke
Dr Walter Schoeller
Dr Erwin Schwenk
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Schering Kahlbaum AG
Original Assignee
Schering Kahlbaum AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Kahlbaum AG filed Critical Schering Kahlbaum AG
Application granted granted Critical
Publication of DE576967C publication Critical patent/DE576967C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Darstellung von Derivaten des männlichen Sexualhormons Es wurde*gefunden, daß man Derivate des männlichen Sexualhormons, die eine längere Wirksamkeit entfalten, erhalten kann, wenn man acylierende Mittel auf das männliche Sexualhormon zur Einwirkung bringt, einerlei, welchen Ursprungs das verwendete Hormonpräparat ist. Beispiel i Männliches Keimdrüsenhormon wird in Äther gelöst und im Schiitteltrichter mit einer ätherischen Lösung von Stearoylchlorid versetzt, worauf unter gutem Schütteln und allmählicher Zugabe von Natronlauge in kleinen Anteilen die Acylierung vollbracht wird. Das Reaktionsgemisch muß dauernd alkalisch bleiben. Nach Vertreiben des Äthers säuert man an und extrahiert mit z. B. Petroläther, der nach dem Verdampfen das Stearoylderivat des Hormons hinterläßt. Beispiel 2 Verfährt man nach Beispiel i unter Verwendung von Benzoylchlorid an Stelle des Stearylchlorids, so läßt sich das Benzoylderi-" vat des männlichen Sexualhormons gewinnen. Beispiel 3 5 g eines aus Männerharn gewonnenen Hormonpräparats werden mit 25 ccm Essigsäureanhydrid t Stunde am Rückflußkühler erhitzt, wobei das Hormon völlig in Lösung geht. Man destilliert -das überschüssige Essigsäureanhydrid ab und fraktioniert den Rückstand im Hochvakuum. Bei o,oi mm Druck geht zwischen 8o bis 140' ein. gelbliches 01 über, das das acetylierte männliche Hormon enthält.Process for the preparation of derivatives of the male sex hormone It has been found that derivatives of the male sex hormone which display a longer activity can be obtained if acylating agents are brought into action on the male sex hormone, regardless of the origin of the hormone preparation used. EXAMPLE i Male gonadal hormone is dissolved in ether and an ethereal solution of stearoyl chloride is added in the Schiittel funnel, whereupon the acylation is carried out with good shaking and the gradual addition of caustic soda in small portions. The reaction mixture must remain alkaline at all times. After expelling the ether, it is acidified and extracted with z. B. petroleum ether, which leaves the stearoyl derivative of the hormone after evaporation. EXAMPLE 2 If one proceeds according to Example 1 using benzoyl chloride instead of stearyl chloride, the benzoyl derivative of the male sex hormone can be obtained the hormone is completely in solution. distillation -the excess acetic anhydride and the residue is fractionated in a high vacuum. at o, oi mm pressure is between 8o to 140 'a. yellowish about 01, which contains the acetylated male hormone.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Derivaten des männlichen Sexualhormons, dadurch gekennzeichnet, daß man das männliche Sexualhormon mit acylierenden Mitteln behandelt. PATENT CLAIM: Process for the preparation of derivatives of the male sex hormone, characterized in that the male sex hormone is treated with acylating agents.
DE1930576967D 1930-07-10 1930-07-10 Process for the preparation of derivatives of the male sex hormone Expired DE576967C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE576967T 1930-07-10

Publications (1)

Publication Number Publication Date
DE576967C true DE576967C (en) 1933-05-19

Family

ID=6570094

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1930576967D Expired DE576967C (en) 1930-07-10 1930-07-10 Process for the preparation of derivatives of the male sex hormone

Country Status (1)

Country Link
DE (1) DE576967C (en)

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