CH215551A - Process for the preparation of a new enol derivative containing the sterol core. - Google Patents

Process for the preparation of a new enol derivative containing the sterol core.

Info

Publication number
CH215551A
CH215551A CH215551DA CH215551A CH 215551 A CH215551 A CH 215551A CH 215551D A CH215551D A CH 215551DA CH 215551 A CH215551 A CH 215551A
Authority
CH
Switzerland
Prior art keywords
preparation
agent
acid
new
derivative containing
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH215551A publication Critical patent/CH215551A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes 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 eines neuen, den     Sterinkern    enthaltenden     Enolderivates.       Gegenstand der vorliegenden Erfindung  bildet ein Verfahren zur Darstellung eines  neuen, den     Sterinkern    enthaltenden     Enol-          derivates,    welches dadurch gekennzeichnet       ist,    dass man auf d     4,5    -Testosteron -17     -          u-butyrat    ein     acetylierendes        Mittel    einwirken  lässt.  



  Das so gewonnene     Enolacetat        des        Testo-          steron    - n -     butyrates    bildet Kristalle vom  F. 96,5-98  . Mit     Tetranitromethan    färbt es  sich     intensiv    braun.  



  Das neue     Enolderivat    soll therapeutische  Verwendung finden oder als Zwischenpro  dukt zur Gewinnung     therapeutisch    wirksamer  Verbindungen dienen.  



  <I>Beispiel:</I>  1. Teil     Testosteron-n-butyrat    wird mit  1 Teil wasserfreiem     Natriuma.oetat    und mit  75 Teilen     Essigsäureanhydrid    während       4\?    Stunden am     Rückfluss    gekocht. Nachdem  das     Essigsäureanhydrid    im Vakuum vollstän  dig entfernt     ist,    löst man das     Natriumacetat       in wenig Wasser und versetzt hierauf mit  soviel     Äthanol,    dass das ölige Reaktionspro  dukt heiss in Lösung geht. Beim Abkühlen  scheidet sich das     Enolacetat    des Testosteron  n-butyrates in Nadeln aus.

   Aus Methanol       umkristallisiert    schmilzt es bei 96,5-98    und gibt mit     Tetranitromethan    intensive       Braunfärbung.     



  Man kann an Stelle von     Natriumacetat     auch ein anderes Salz der Essigsäure verwen  den oder ohne Zusatz eines solchen arbeiten.  



  Denselben     Endstoff    erhält man auch  durch Kochen von     Testosteron-n-butyrat,    zum  Beispiel     mit        Acetylchlorid,    in einem orga  nischen Lösungsmittel, wie Benzin, bis zur       vollendeten    Reaktion. Ferner kann man zur       Bindung    der entstehenden Salzsäure zum Bei  spiel eine tertiäre Base, wie     Pyridin        und,der-          zleichen,        zuzeben.  



  Process for the preparation of a new enol derivative containing the sterol core. The present invention relates to a process for the preparation of a new enol derivative containing the sterol nucleus, which is characterized in that an acetylating agent is allowed to act on d 4,5 -testosterone -17-u-butyrate.



  The enol acetate of testosterone-n-butyrate obtained in this way forms crystals with a melting point of 96.5-98. With tetranitromethane it turns an intense brown.



  The new enol derivative is intended to be used therapeutically or to serve as an intermediate product to obtain therapeutically effective compounds.



  <I> Example: </I> 1. Part testosterone n-butyrate is mixed with 1 part anhydrous sodium acetate and with 75 parts acetic anhydride for 4 \? Boiled under reflux for hours. After the acetic anhydride has been completely removed in vacuo, the sodium acetate is dissolved in a little water and so much ethanol is added that the oily reaction product dissolves hot. When it cools down, the enol acetate of testosterone n-butyrate is deposited in needles.

   Recrystallized from methanol, it melts at 96.5-98 and gives an intense brown color with tetranitromethane.



  Instead of sodium acetate, another salt of acetic acid can also be used, or work can be carried out without the addition of one.



  The same end product is also obtained by boiling testosterone n-butyrate, for example with acetyl chloride, in an organic solvent such as gasoline until the reaction is complete. Furthermore, to bind the hydrochloric acid formed, for example a tertiary base such as pyridine and similar can be added.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen, den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf d4,s- Testosteron-17-n-butyrat ein acetylierendes, Mittel einwirken. lässt. Das so gewonnene Enolacetat des Testo steron - n - butyrates bildet Kristalle vom F. 9ö,5-98 . Mit Tetranitromethan färbt es sich intensiv braun. PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol core, characterized in that an acetylating agent is used on d4, s-testosterone-17-n-butyrate. leaves. The enol acetate of testosterone-n-butyrate obtained in this way forms crystals of F. 9ö, 5-98. With tetranitromethane it turns an intense brown. Das neue E.nolderivat soll therapeutische Verwendung finden oder als Zwi.schenpro- dukt zur Gewinnung therapeutisch wirksamer Verbindung dienen. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel Essigsäureanhydrid verwendet. 2. The new E.nol derivative is intended to be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. SUBClaims: 1. Method according to claim, characterized in that acetic anhydride is used as the acetylie- rendes agent. 2. Verfahren nach -Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel ein Halogenid der Essigsäure verwendet. 3. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch. gekennzeichnet, dass man in Anwesenheit eines :säurebinden den Mittels arbeitet. 4. Verfahren nach Patentanspruch und den Unteransprüchen. 2 und 3, dadurch ge kennzeichnet, dass man als säurebindendes Mittel eine- tertiäre Base verwendet. Process according to patent claim, characterized in that a halide of acetic acid is used as the acetylie- rendes agent. 3. The method according to claim and dependent claim 2, characterized. characterized in that one works in the presence of an acid-binding agent. 4. The method according to claim and the subclaims. 2 and 3, characterized in that a tertiary base is used as the acid-binding agent. 5. Verfahren nach Patentanspruch und den Unteransprüchen ?, 3 und 4, dadurch gekennzeichnet, da,ss man als säurebindendes Mittel Pyridin verwendet. 5. The method according to claim and the sub-claims?, 3 and 4, characterized in that the acid-binding agent used is pyridine.
CH215551D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215551A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211649T 1936-05-18
CH215551T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215551A true CH215551A (en) 1941-06-30

Family

ID=25725035

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215551D CH215551A (en) 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core.

Country Status (1)

Country Link
CH (1) CH215551A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921696C (en) * 1952-07-06 1954-12-23 Schering Ag Process for the production of injection preparations from testosterone esters with a particularly pronounced protracted androgenic effect

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921696C (en) * 1952-07-06 1954-12-23 Schering Ag Process for the production of injection preparations from testosterone esters with a particularly pronounced protracted androgenic effect

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