CH215557A - 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
CH215557A
CH215557A CH215557DA CH215557A CH 215557 A CH215557 A CH 215557A CH 215557D A CH215557D A CH 215557DA CH 215557 A CH215557 A CH 215557A
Authority
CH
Switzerland
Prior art keywords
agent
preparation
acid
derivative containing
new
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 CH215557A publication Critical patent/CH215557A/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     Enolderi-          vates,,    welches dadurch gekennzeichnet ist,  dass man auf 4     4,5-Testosteron-17-isobutyrat     ein     acetylierendes    Mittel     einwirken    lässt.  



  Das so gewonnene     Enolacetat    des     Testo-          steron-isobutyrates        bildet    Kristalle, vom  F.134     bis    186  . Mit     Tetranitromethan    färbt  es sich intensiv braun.  



  Das neue     Enolderivat    soll     therapeutische     Verwendung finden oder als Zwischenprodukt  zur Gewinnung therapeutisch wirksamer Ver  bindungen dienen.  



       Beispiel:     1 Teil     Testosteron-isobutyrat    wird mit  1 Teil wasserfreiem     Natriumaeetat    und mit  75 Teilen     Essigsäureanhydrid    während 42       Stunden    am     R.ückfluss    gekocht. Nachdem das       Essigsäureanhydrid    im Vakuum vollständig       entfernt    ist, löst man das     Natriumacetat    in  wenig Wasser und versetzt hierauf mit soviel    Äthanol, dass das ölige Reaktionsprodukt  heiss in Lösung geht.

   Beim Abkühlen scheidet  sich das     Enolacetat    des     Testosteron-n-buty-          rates    in Nadeln aus.     Aus    Methanol     umkristal-          lisiert    schmilzt es- bei 134 bis<B>136'</B> und gibt  mit     Tetranitromethan    intensive Braunfär  bung.  



  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-isobutyrat,     zum Beispiel mit     Acetylchlorid    in einem or  ganischen     Lösungsmittel,        wie    Benzin, bis zur  vollendeten Reaktion. Ferner kann man zur  Bindung der entstehenden Salzsäure zum Bei  spiel eine tertiäre Base, wie     Pyridin    und  dergleichen, zugeben.



  Process for the preparation of a new enol derivative containing the sterol core. The subject matter of the present invention is 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 4 4,5-testosterone-17-isobutyrate.



  The enol acetate of testosterone isobutyrate obtained in this way forms crystals, from F.134 to 186. With tetranitromethane it turns an intense brown.



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



       Example: 1 part testosterone isobutyrate is refluxed with 1 part anhydrous sodium acetate and 75 parts acetic anhydride for 42 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-butylate is deposited in needles. Recrystallized from methanol, it melts at 134 to 136 '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 obtained by boiling testosterone isobutyrate, 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 the like can be added.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen, .den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf A4,1- Testosteron-17-isobutyrat ein acetylierendes Mittel einwirken lässt. Das so .gewonnene Enolacetat des Testo- steron-isobutyrates bildet Kristalle vom F. 134 bis 136 . Mit Tetranitromethan färbt es sich intensiv braun. PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol nucleus, characterized in that an acetylating agent is allowed to act on A4,1-testosterone-17-isobutyrate. The enol acetate of testosterone isobutyrate obtained in this way forms crystals with a melting point of 134 to 136. With tetranitromethane it turns an intense brown. Das neue Enol.derivat soll therapeutische Verwendung finden oder als Zwischenprodukt zur Gewinnung therapeutisch wirksamer Ver bindungen dienen. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, da.ss man als acetylie- rendes Mittel Essigsäureanhydrid verwendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel ein Halogenid der Essigsäure verwendet. The new Enol.derivat is intended to be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. <B> SUBClaims: </B> 1. Method according to patent claim, characterized by the fact that acetic anhydride is used as the acetylating agent. 2. The method according to claim, characterized in that a halide of acetic acid is used as the acetylie- rendes agent. 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. 5. Verfahren nach Patentanspruch und den Unteransprüchen 2, 3 und 4"dadurch ge kennzeichnet. dass man als säurebindendes Mittel Pyridin verwendet. Method according to claim and dependent claim 2, characterized in that the agent is used 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. The method according to claim and the dependent claims 2, 3 and 4 "characterized in that pyridine is used as the acid-binding agent.
CH215557D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215557A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215557T 1936-05-18
CH211649T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215557A true CH215557A (en) 1941-06-30

Family

ID=25725041

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215557D CH215557A (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) CH215557A (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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