CH215548A - 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
CH215548A
CH215548A CH215548DA CH215548A CH 215548 A CH215548 A CH 215548A CH 215548D A CH215548D A CH 215548DA CH 215548 A CH215548 A CH 215548A
Authority
CH
Switzerland
Prior art keywords
agent
preparation
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 CH215548A publication Critical patent/CH215548A/en

Links

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

  

      Yerfahren    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 4     4,5    -Testosteron -17     -          propionat    ein     acetylierendes        Mittel    einwirken  lässt.  



  Das so gewonnene     Enolacetat    des.     Testo-          steron    -     propionates    bildet Kristalle vom  F. 140-141  . 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>  0,2 Teile     Testosteronpropionat    und 0,4 Teile       wasserfreies        Natriumacetat    werden in 7 Tei  len     Essigsäureanhydrid    während etwa 40 Stun  den zum Sieden erhitzt. Nach     Abdestillieren     des     Essigsäureanhydrides    im Vakuum wird  der Rückstand mit verdünntem Alkohol zum         Kristallisieren    gebracht und hierauf durch       LTmlösen    aus Methanol gereinigt. Das so ge  wonnene     Enolacetat    des     Testosteronpropio-          nates    schmilzt bei 140-141  .  



  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     Testosteronpropionat,    zum  Beispiel mit     Acetylchlorid,    in einem orga  nischen Lösungsmittel, wie Benzin, bis zur  vollendeten     Reaktion.    Ferner kann     man    zur  Bildung der     entstehenden    Salzsäure zum Bei  spiel eine tertiäre Base, wie     Pyridin    und der  gleichen, zugeben.



      Process for the preparation of a new enol derivative containing the sterol core. The subject 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-propionate.



  The enol acetate of testosterone propionate obtained in this way forms crystals with a mp of 140-141. 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> 0.2 part testosterone propionate and 0.4 part anhydrous sodium acetate are heated to boiling in 7 parts acetic anhydride for about 40 hours. After the acetic anhydride has been distilled off in vacuo, the residue is made to crystallize with dilute alcohol and then purified by dissolving it from methanol. The enol acetate of testosterone propionate obtained in this way melts at 140-141.



  Another salt of acetic acid can also be used in place of sodium acetate or work can be carried out without the addition of one.



  The same end product is also obtained by boiling testosterone propionate, for example with acetyl chloride, in an organic solvent such as gasoline until the reaction is complete. Furthermore, for the formation of 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 d 4,5 _ Testosteron-17-propionat ein acetylierendes Mittel einwirken lässt. Das so gewonnene Enola.cetat des Testo- steron-propionates bildet Kristalle vom F. 140-141 . 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 allowed to act on d 4,5_ testosterone-17-propionate. The enol acetate of testosterone propionate obtained in this way forms crystals with a temperature of 140-141. With tetranitromethane it turns an intense brown. Das neue E.nolderivat sohl therapeutische Verwendung finden oder als Zwischenpro dukt zur Gewinnung therapeutisch wirksamer Verbindung dienen. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel Essigsäuxeanhydrid verwendet. 2. Verfahren nach Patentanspruch, .da durch gekennzeichnet, dass man als acetylie- rendes Mittel ein Halogenid der Essigsäure verwendet. 3. The new E.nolderivat should be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. <B> SUBClaims: </B> 1. Process according to patent claim, characterized in that acetic anhydride is used as the acetylating agent. 2. The method according to claim, .da characterized in that a halide of acetic acid is used as acetylie- rendes agent. 3. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den Mittels arbeitet. 4. Verfahren nach Patentansprueli und den Unteransprüchen \? und 3, dadurch ge kennzeichnet, dass man als säurebindendes 1littel eine tertiäre Base verwendet. 5. Verfahren nach Patentanspruch und den Unteranspriichen 2, 3 und 4, dadurch gekennzeichnet, 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. Method according to patent claims and the subclaims \? and 3, characterized in that a tertiary base is used as the acid-binding agent. 5. The method according to claim and dependent claims 2, 3 and 4, characterized in that pyridine is used as the acid-binding agent.
CH215548D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215548A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215548T 1936-05-18
CH211649T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215548A true CH215548A (en) 1941-06-30

Family

ID=25725032

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215548D CH215548A (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) CH215548A (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

Similar Documents

Publication Publication Date Title
CH215548A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH216106A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215549A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215556A (en) Process for the preparation of a new enol derivative containing the sterol core.
DE1593315C (en)
CH217936A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215554A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215550A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215552A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH217937A (en) Process for the preparation of a new enol derivative containing the sterol core.
DE432803C (en) Process for the preparation of derivatives of basic acidyloxyalkyl ethers
CH215555A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215553A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215557A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH215551A (en) Process for the preparation of a new enol derivative containing the sterol core.
AT229496B (en) Process for the preparation of the new nicotinic acid ester of dihydroxycodeinone
DE959189C (en) Process for the preparation of 17ª ‰ -acyloxy-20-keto-allopregnans and -pregnenes
AT159962B (en) Process for the preparation of esters of the adrenal cortical hormones or largely purified adrenal cortical hormones.
CH216104A (en) Process for the preparation of a new enol derivative containing the sterol core.
DE764747C (en) Process for the preparation of derivatives of androstediol-3, 17 and androstenediol-3, 17
AT222647B (en) Process for the preparation of new acyl compounds of 4-aminophenol
DE964596C (en) Process for the preparation of esters of the Allopregnan, Pregnan and Pregnan series
AT239968B (en) Process for the production of new nicotinic acid esters
CH215558A (en) Process for the preparation of a new enol derivative containing the sterol core.
CH214328A (en) Process for the preparation of a new enol derivative containing the sterol core.