CH204772A - Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol. - Google Patents

Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol.

Info

Publication number
CH204772A
CH204772A CH204772DA CH204772A CH 204772 A CH204772 A CH 204772A CH 204772D A CH204772D A CH 204772DA CH 204772 A CH204772 A CH 204772A
Authority
CH
Switzerland
Prior art keywords
estradiol
preparation
aromatic substituted
substituted ester
butyrate
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 CH204772A publication Critical patent/CH204772A/en

Links

Classifications

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

Description

  

  Verfahren zur Darstellung eines neuen     aliphatisch-aromatisch        substitaierten        Esters     des     Oestradiols.       Es wurde gefunden,     dass    man zu     einem     neuen     @aliphatisch    - aromatisch substituierten  Ester des     Oestradiels    mit ganz besonders     pro-          trahierter    Wirkung .gelangen kann, wenn  man auf     Oestradiol    - 8 - mono -n-     butyrat    ein       Benzoylierungsmittel        einwirken;

          läBt.     



  Als     geeignete        Benzoylierungsmittel    kom  men z. B.     Benzoesäureh@alogenäde,        -anhydrid,          -ester    oder die Säure     selbst    in Frage.  



  Das so gewonnene     Oestra@diol-3-n-butyrat-          17-benzoat    bildet Kristalle vom F. 141,5 bis  142  . Es soll therapeutische     Verwendung     finden.  



  <I>Beispiel:</I>  2,0     Teile        0±stradäol-3-mono-n-butyrat    vom  F. 98 bis     9'9      werden in 1-5 Teilen     Pyridin     gelöst und     unter    Umrühren 1,3 Teile     Benzoyl-          ühlorid    zugesetzt.

   Nach     12stündigem    Stehen  bei     Zimmertemperatur    werden 300 Teile  Wasser hinzugefügt und .das ausgeschiedene    01 in Äther     aufgenommen.    Die     abgetrennte     ätherische Lösung wird mit     Wasser,   
EMI0001.0037  
       -Soda.,          Wasser,   
EMI0001.0040  
   Schwefelsäure     und    nochmals mit  Wasser     gewaschen    und mit Natriumsulfat  -getrocknet.

   Nach .dem Entfernen :des Lösungs  mittels bleibt     Oestradiol-3-mono-n-butyrat-17-          benzoat    als kristalline Substanz zurück, die  aus     Aoeton-Alkoholwaeser        umkristallnsiert     werden kann. F. 141,5 bis 142'  .  



  An     Stelle    von     Benzoylchlorid    kann man  ebensogut auch ein anderes     Säurehalogenid,     wie z. B. .das     Bromid    verwenden.  



  Die     Reaktion    kann     auch    in Anwesenheit  anderer tertiärer Basen, wie z. B.     Dimethyl-          anilin,        Chinolin    und dergl. oder auch ohne  ,solche Basen     durchgeführt    werden.  



  Die .gleiche Verbindung erhält man auch  durch Behandeln von     Oestradiol    - 17 -     mono-          benzoat    mit einem     n-Butyryläerungsmittel.  



  Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol. It has been found that a new aliphatic-aromatic substituted ester of estradiol with a particularly pronounced effect can be obtained if a benzoylating agent is used on estradiol-8-mono-n-butyrate;

          lets.



  Suitable benzoylating agents come men z. B. Benzoesäureh @ alogenäde, anhydride, ester or the acid itself in question.



  The Oestra @ diol-3-n-butyrate-17-benzoate obtained in this way forms crystals with a melting point of 141.5 to 142. It should find therapeutic use.



  <I> Example: </I> 2.0 parts of 0 ± stradenol-3-mono-n-butyrate with a melting point of 98 to 9.9 are dissolved in 1-5 parts of pyridine and 1.3 parts of benzoyl chloride are dissolved with stirring added.

   After standing for 12 hours at room temperature, 300 parts of water are added and the precipitated oil is taken up in ether. The separated ethereal solution is mixed with water,
EMI0001.0037
       -Soda., Water,
EMI0001.0040
   Sulfuric acid and washed again with water and dried with sodium sulfate.

   After the removal of the solvent, oestradiol-3-mono-n-butyrate-17-benzoate remains as a crystalline substance which can be recrystallized from Aoeton alcohol. F. 141.5 to 142 '.



  Instead of benzoyl chloride, you can just as well use another acid halide, such as. B. Use the bromide.



  The reaction can also be carried out in the presence of other tertiary bases, such as e.g. B. dimethyl aniline, quinoline and the like. Or even without, such bases are carried out.



  The same compound is also obtained by treating oestradiol-17-monobenzoate with an n-butyryl acid detergent.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen aliphatisch -aromatischsubstituierten Esters des Oestradiols, dadurch gekennzeichnet, dass man auf Oestradiol - 3 - mono - n - butyrat ein Ben.zoylierungsmittel einwirken lässt. Das so gewonnene Oestradiol-3-n-butyrat- 17-benzoat bildet Kristalle vom F. 141,5 bis 142 . Es soll therapeutische Verwendung finden. UNTERANSPRüCHE 1. PATENT CLAIM: Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol, characterized in that a benzoylating agent is allowed to act on estradiol-3-mono-n-butyrate. The estradiol 3-n-butyrate-17-benzoate obtained in this way forms crystals with a melting point of 141.5 to 142. It should find therapeutic use. SUBCLAIMS 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Benzoylie- rungsmittel ein Benzoylhalogenid verwen det. 2. Verfahren nach Patentanspruch und Un teranspruch 1, .dadurch gekennzeichnet, dass man als Benzoylierungsmittel Benzoyl- chlorid verwendet. 3. Process according to claim, characterized in that a benzoyl halide is used as the benzoylating agent. 2. The method according to claim and sub-claim 1, characterized in that the benzoylating agent used is benzoyl chloride. 3. Verfahren nach Patentanspruch und Un teransprüchen 1 und 2, dadurch gekenn zeichnet, dass man in Gegenwart einer ter- tiären Base arbeitet. 4. Verfahren nach Patentanspruch und ,den Unteransprüchen 1 bis 3, dadurc-i gekenn zeichnet, da.ss man in Gegenwart von Pyri- din arbeitet. 5. Process according to patent claim and sub-claims 1 and 2, characterized in that one works in the presence of a tertiary base. 4. The method according to claim and, the dependent claims 1 to 3, dadurc-i marked is characterized da.ss one works in the presence of pyridine. 5. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Ben.zoylie- runbs@mittel Benzoe@säureanhydrid verwen det. Process according to patent claim, characterized in that benzoic acid anhydride is used as the Ben.zoylie- runbs @ agent.
CH204772D 1936-11-20 1936-12-16 Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol. CH204772A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH201115T 1936-11-20
CH204772T 1936-12-16

Publications (1)

Publication Number Publication Date
CH204772A true CH204772A (en) 1939-05-15

Family

ID=25723660

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204772D CH204772A (en) 1936-11-20 1936-12-16 Process for the preparation of a new aliphatic-aromatic substituted ester of estradiol.

Country Status (1)

Country Link
CH (1) CH204772A (en)

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