CH196480A - Process for the preparation of the diacetyl ester of 17-methyloctahydrofollicle hormone. - Google Patents

Process for the preparation of the diacetyl ester of 17-methyloctahydrofollicle hormone.

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Publication number
CH196480A
CH196480A CH196480DA CH196480A CH 196480 A CH196480 A CH 196480A CH 196480D A CH196480D A CH 196480DA CH 196480 A CH196480 A CH 196480A
Authority
CH
Switzerland
Prior art keywords
sep
hormone
methyloctahydrofollicle
preparation
formula
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
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
Publication of CH196480A publication Critical patent/CH196480A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung des     Diacetylester    s von     17-Nethyloctahydrofollikelhor        mon.       Gegenstand vorliegenden     Patentes    ist ein  Verfahren zur     Darstellung    des.

       Diacetylesters     von     17-Methyloctahydrofodlikelhormon    der  Formel     C"H3202,    welches dadurch gekenn  zeichnet ist, dass man auf     17-Methylocta-          hydrofollikelhormon    .der     Formel        C"H"02    ein       acetylierend.es        Mittel    bis zur Bildung des     Di-          es.ters        einwirken        lässt.     



       Das:    als     Ausgangsmaterial    für     .das    vorlie  gende Verfahren dienende     17-Methylocta-          hydrofollikelhormon    der Formel     C1flH320_     kann zum Beispiel gemäss dem Verfahren des  Patentes: Nr. 194280 gewonnen werden.  



       Beispiel:     5(l0 mg     17-Methyloetahydrofollikelho@rmon     der Formel     C"H;202    werden in 30     cm'     trockenem     Benzal    gelöst, worauf' die Lösung  mit 2 am'     Acetylchlorid    versetzt wird. Nach       Zugabe    von 5 cm' trockenem     Pyridin    wird  .die Reaktionslösung 11/a :Stunden auf dem  Wasserbade zum :Sieden erhitzt. Nach dem  Erkalten wird     unter    Kühlung in verdünnte    Salzsäure eingegossen, mit Äther ausgeschüt  telt, .die ätherische Lösung mit Wasser neu  tral gewaschen, getrocknet und abgedampft.

    Es     hinterbleibt    als     Rückstand    ein gelb ge  färbtes Harz, der     Diaeetylester    des     17-112e-          thylo-ctahydrofollikelhormons.     



       Darr    Verfahrensprodukt ist neu, der Ester  besitzt die charakteristische Eigenschaft, dass  er ebenso wie der freie Alkohol     eine    dem  männlichen     Keimdrüsenhormon    ähnliche Wir  kung zeigt, aber im Gegensatz zu     diesem,    der  vom Organismus verhältnismässig rasch aus  geschieden wird, seine Wirkung über eine  längere Zeit hin     ausübt;    offenbar wird der       Ester    vom Organismus nur allmählich ge  spalten und bildet so     gewissermassen    ein       Hormond-epat    im     Organismus,    wodurch für  die Erreichung einer anhaltenden Wirkung  eine weniger häufige Zufuhr genügt.



  Method for the preparation of the diacetyl ester of 17-Nethyloctahydrofollikelhormon. The present patent is a method for the representation of.

       Diacetyl ester of 17-methyloctahydrofollicle hormone of the formula C "H3202, which is characterized in that an acetylating agent is allowed to act on 17-methyloctahydrofollicle hormone of the formula C" H "02 until the diester is formed.



       The 17-methyloctahydrofollicle hormone of the formula C1flH320_, which serves as the starting material for the present process, can be obtained, for example, according to the process of patent: No. 194280.



       Example: 5 (10 mg of 17-methyloetahydrofollicular hormone of the formula C "H; 202 are dissolved in 30 cm 'of dry benzal, whereupon 2 am of acetyl chloride is added to the solution. After addition of 5 cm of dry pyridine, the Reaction solution 11 / a: Heated to boiling on the water bath for hours After cooling, it is poured into dilute hydrochloric acid, extracted with ether, the ethereal solution washed neutral with water, dried and evaporated.

    A yellow colored resin remains as residue, the diethyl ester of 17-112-thylo-ctahydrofollicle hormone.



       The product of the process is new, the ester has the characteristic property that, like the free alcohol, it shows an effect similar to the male gonadal hormone, but in contrast to this, which is excreted relatively quickly by the organism, its effect over a longer period of time exercises; evidently the ester is only gradually cleaved by the organism and so to a certain extent forms a hormone epate in the organism, whereby a less frequent intake is sufficient to achieve a lasting effect.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des Diacetyl- esters, von 17-Methyloct.ahydrofollik.elhormon EMI0002.0001 der <SEP> Formel <SEP> dadureh <SEP> gekennzeieh net, <SEP> dass <SEP> man <SEP> a.uf <SEP> 17-1,Tetbvloetabvdrofollil;el hormon <SEP> der <SEP> Formel <SEP> C'1@,H.: PATENT CLAIM: Process for the preparation of the diacetyl ester, of 17-Methyloct.ahydrofollik.elhormon EMI0002.0001 the <SEP> formula <SEP> dadureh <SEP> marked net, <SEP> that <SEP> man <SEP> on <SEP> 17-1, Tetbvloetabvdrofollil; el hormon <SEP> of the <SEP> formula <SEP > C'1 @, H .: @n, <SEP> ein <SEP> acetylieren des <SEP> -Mittel <SEP> bis <SEP> zur <SEP> Bildung <SEP> des <SEP> Diesters <SEP> ein wirken <SEP> lässt. <tb> Das <SEP> neue, <SEP> in <SEP> Form <SEP> eines <SEP> gelb <SEP> gefüri@t@n <tb> Harzes <SEP> erhaltene <SEP> Produkt <SEP> zeigt <SEP> ebenso <SEP> -i < , EMI0002.0002 das <SEP> Ausgangsmaterial <SEP> eine <SEP> dem <SEP> männliehen <tb> H.eimdrü@senbormon <SEP> alinlielie <SEP> 'Wirkung. <SEP> übt <tb> <B>,</B> <SEP> Aer <SEP> im <SEP> Gegensatz <SEP> zu <SEP> dieseln <SEP> seine <SEP> Wirkurig <tb> l-i <SEP> -end <SEP> eines <tb> w <SEP> <B>*</B> <SEP> bi <SEP> <B>#7,</B> <SEP> ans. @n, <SEP> a <SEP> acetylating the <SEP> agent <SEP> to <SEP> for <SEP> formation <SEP> of the <SEP> diester <SEP> allows <SEP> to take effect. <tb> The <SEP> new, <SEP> in <SEP> form <SEP> of a <SEP> yellow <SEP> gefüri @ t @ n <tb> Resin <SEP> received <SEP> product <SEP> shows <SEP> as well as <SEP> -i <, EMI0002.0002 the <SEP> starting material <SEP> a <SEP> the <SEP> male <tb> H.eimdrü@senbormon <SEP> alinlielie <SEP> 'effect. <SEP> practices <tb> <B>, </B> <SEP> Aer <SEP> in the <SEP> contrast <SEP> to <SEP> diesels <SEP> its <SEP> effective <tb> l-i <SEP> -end <SEP> one <tb> w <SEP> <B> * </B> <SEP> to <SEP> <B> # 7, </B> <SEP> ans.
CH196480D 1934-02-22 1935-02-19 Process for the preparation of the diacetyl ester of 17-methyloctahydrofollicle hormone. CH196480A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE196480X 1934-02-22

Publications (1)

Publication Number Publication Date
CH196480A true CH196480A (en) 1938-03-15

Family

ID=5754920

Family Applications (1)

Application Number Title Priority Date Filing Date
CH196480D CH196480A (en) 1934-02-22 1935-02-19 Process for the preparation of the diacetyl ester of 17-methyloctahydrofollicle hormone.

Country Status (1)

Country Link
CH (1) CH196480A (en)

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