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CH195775A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH195775A
CH195775A CH195775DA CH195775A CH 195775 A CH195775 A CH 195775A CH 195775D A CH195775D A CH 195775DA CH 195775 A CH195775 A CH 195775A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
new ester
new
marked
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 CH195775A publication Critical patent/CH195775A/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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C07J1/0025—Esters
    • 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 Esters.    Es wurde     gefunden,    dass man zu neuen       Estern    von     gesättigten        odeT        ungesättigten          Oxyketonen    vom     Typus    des     Androstanol-          (17)-on-(3)    gelangen kann, wenn man     diese          Oxyketone    mit solchen     acylierenden    Reagen  zien behandelt,

   die neben der zur     Acylierung     dienenden Gruppe noch eine     zur        Salzbildung          befähigte    oder eine hierin     überführbare     Gruppe enthalten.  



  Geeignete     acylierende        Reagenzien        sind    z. B.  Säurechloride,     Säureaahydride,wieBernstein-          eäureanhydrid,        Maleinsäureanhydrid,        Phthal-          säureanhydrid,        Chlorsulfonsäure,    Phosphor  oxyohlorid und      & ngleichen.       Als     Oxyketone    kommen     insbesondere        in.     Frage z.

   B.     Androstanol-(17)-on-(3),        17-Me-          thyl-androstanol-(17)-on-(3),        A4,5-Androste-          nol-(17)-on-(3),        04,5-17-Methyl-androstenol-          (17)-on-(3),    oder deren     Stereoäsomeren.     



       Gegenstand    des     vorliegenden        Patentes          bildet        ein    Verfahren zur     Darstellung    eines  neuen     Esters,    welches dadurch gekennzeich  net ist,     dass    man auf     A4,5-Androstenol-(17)-          on-(3)        ein        @Suocinylierungsmttel        einwirken          lässt.     



  Der so gewonnene     04,5-Andrastenol-(17)-          on    - (3) -     monobernssteine,äureester    der     Formel     
EMI0001.0057     
    weist     dimorphe        Kristallformen    auf von -den  Schmelzpunkten 182 bis 184' respektive<B>191</B>    bis<B>193'.</B> Er bildet,     namentlich        mit        Alka-          lien,    leicht     wasserlösliche        Salze.       
EMI0002.0001     
  
    Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> therapeutische
<tb>  Verwendung <SEP> finden.
<tb>  



  <I>Beispiel:</I>
<tb>  0,6 <SEP> g <SEP> A4,5-Androstenol-(17)-oii-(3) <SEP> wer  den <SEP> mit <SEP> 0,6g <SEP> Bernsteinsäureanhydrid <SEP> und
<tb>  <B>cm'</B> <SEP> absolutem <SEP> Pvridin <SEP> während <SEP> 5 <SEP> Stunden
<tb>  am <SEP> siedenden <SEP> Wasserbad <SEP> erwärmt. <SEP> Das <SEP> Reak  tionsgemisch <SEP> giesst <SEP> man <SEP> in <SEP> 2n-Sodalösung.
<tb>  zieht <SEP> diese <SEP> mit <SEP> Xther <SEP> aus <SEP> und <SEP> säuert <SEP> sie
<tb>  nachher <SEP> an, <SEP> wobei <SEP> Flocken <SEP> a.usfailen. <SEP> Diese
<tb>  werden <SEP> abgesaugt <SEP> und <SEP> nach <SEP> dem <SEP> Trocknen
<tb>  aus <SEP> Benzol <SEP> oder <SEP> 1,sopropy <SEP> läther <SEP> unikri8t#tlli  siert. <SEP> Der <SEP> so <SEP> rein <SEP> erhaltene <SEP> !'@45- <SEP> Andrast@nol-     
EMI0002.0002     
  
    (17)-on-(:

  3)-monobernst@-insäureester <SEP> weist <SEP> di  morphe <SEP> Kristallformen <SEP> auf <SEP> von <SEP> den <SEP> Schmelz  punkten <SEP> 18? <SEP> bis <SEP> 184' <SEP> respektive <SEP> 191. <SEP> bis <SEP> <B>193'.</B>
<tb>  



  Als <SEP> Succinylierungsmittel <SEP> kann <SEP> man <SEP> zum
<tb>  Beispiel <SEP> auch <SEP> Bernsteinsäure <SEP> verwenden.



  Process for the preparation of a new ester. It has been found that new esters of saturated or unsaturated oxyketones of the androstanol- (17) -one- (3) type can be obtained if these oxyketones are treated with such acylating reagents,

   which, in addition to the group used for acylation, also contain a group capable of salt formation or a group which can be converted therein.



  Suitable acylating reagents are, for. B. Acid chlorides, acid aahydrides, such as amber anhydride, maleic anhydride, phthalic anhydride, chlorosulfonic acid, phosphorus oxychloride and the like. Particularly suitable oxyketones are.

   B. Androstanol- (17) -one- (3), 17-methyl-androstanol- (17) -one- (3), A4,5-androstenol- (17) -one- (3), 04,5-17-methyl-androstenol- (17) -one- (3), or their stereoisomers.



       The subject of the present patent is a process for the preparation of a new ester, which is characterized in that a suocinylation agent is allowed to act on A4,5-androstenol- (17) -on- (3).



  The 04,5-Andrastenol- (17) - on - (3) - monobernstones obtained in this way, acid esters of the formula
EMI0001.0057
    has dimorphic crystal forms from melting points 182 to 184 'or <B> 191 </B> to <B> 193'. </B> It forms easily water-soluble salts, in particular with alkalies.
EMI0002.0001
  
    The <SEP> new <SEP> connection <SEP> should <SEP> therapeutic
<tb> Find use <SEP>.
<tb>



  <I> Example: </I>
<tb> 0.6 <SEP> g <SEP> A4,5-androstenol- (17) -oii- (3) <SEP> are the <SEP> with <SEP> 0.6g <SEP> succinic anhydride <SEP> and
<tb> <B> cm '</B> <SEP> absolute <SEP> Pvridin <SEP> during <SEP> 5 <SEP> hours
<tb> heated on the <SEP> boiling <SEP> water bath <SEP>. <SEP> The <SEP> reaction mixture <SEP> is poured <SEP> one <SEP> into <SEP> 2n soda solution.
<tb> <SEP> pulls this <SEP> with <SEP> Xther <SEP> from <SEP> and <SEP> acidifies <SEP> them
<tb> afterwards <SEP> on, <SEP> whereby <SEP> flakes <SEP> a.usfailen. <SEP> This
<tb> <SEP> are extracted <SEP> and <SEP> after <SEP> the <SEP> drying
<tb> made of <SEP> benzene <SEP> or <SEP> 1, sopropy <SEP> ether <SEP> unikri8t # tllized. <SEP> The <SEP> so <SEP> pure <SEP> received <SEP>! '@ 45- <SEP> Andrast @ nol-
EMI0002.0002
  
    (17) -on- (:

  3) -monobernst @ -insäureester <SEP> has <SEP> di morphic <SEP> crystal forms <SEP> <SEP> of <SEP> the <SEP> melting points <SEP> 18? <SEP> to <SEP> 184 '<SEP> or <SEP> 191. <SEP> to <SEP> <B> 193'. </B>
<tb>



  As a <SEP> succinylating agent <SEP> <SEP> can be used as <SEP> for
<tb> Example <SEP> also use <SEP> succinic acid <SEP>.

Claims (1)

EMI0002.0003 PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man auf A4,5-An,drostenol-(17)-on-(3) ein Succinylie- rurngsmittel einwirken läBt. Der so gewonnene A4,5-Androstenol-(17)- o i)-(' ) EMI0002.0003 PATENT CLAIM: A process for the preparation of a new ester, characterized in that a succinic agent is allowed to act on A4,5-an, drostenol- (17) -one- (3). The A4,5-androstenol- (17) - o i) - (') obtained in this way -monobernsteinsä.ureester der Formel EMI0002.0018 weist dimorphe Kristallformen auf von den Schmelzpunkten 182 bis 184' respektive 191 biee 193 . Er bildet, na,mentlicli mit Alkalien, leicht wasserlösliche Salze. Die neue Verbindung soll therapeutische Verwendung finden. -monosuccinic acid esters of the formula EMI0002.0018 has dimorphic crystal forms from melting points 182 to 184 'and 191 to 193, respectively. It forms, well, mentally with alkalis, easily water-soluble salts. The new compound should find therapeutic use. EMI0002.0027 UNTERANSPRüCHE <tb> 1. <SEP> Zerfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet. <SEP> dass <SEP> man <SEP> als <SEP> Suecinylie- EMI0002.0028 runpsmittel <SEP> Bern@steinsäureanhydrid <SEP> ver wendet. <tb> ?. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> da.ss <SEP> man <SEP> die <SEP> 'Succinylie rung <SEP> in <SEP> Gegenwart <SEP> tertiärer <SEP> Basen <SEP> aus führt. EMI0002.0027 SUBCLAIMS <tb> 1. <SEP> Disintegration <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked. <SEP> that <SEP> man <SEP> as <SEP> Suecinylie- EMI0002.0028 runps medium <SEP> ambersteinsäureanhydrid <SEP> is used. <tb>?. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> da.ss <SEP> one <SEP> executes the <SEP> 'succination <SEP> in <SEP> presence of <SEP> tertiary <SEP> bases <SEP>.
CH195775D 1935-08-02 1935-08-02 Process for the preparation of a new ester. CH195775A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH195775T 1935-08-02

Publications (1)

Publication Number Publication Date
CH195775A true CH195775A (en) 1938-02-15

Family

ID=4440098

Family Applications (1)

Application Number Title Priority Date Filing Date
CH195775D CH195775A (en) 1935-08-02 1935-08-02 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH195775A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708651A (en) * 1955-01-07 1955-05-17 Pfizer & Co C Water-soluble esters of pregnanolones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2708651A (en) * 1955-01-07 1955-05-17 Pfizer & Co C Water-soluble esters of pregnanolones

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