CH210718A

CH210718A - Method for representing a connection of the adrenal cortex hormone series.

Info

Publication number: CH210718A
Authority: CH
Inventors: Gesellschaft Fuer Chemis Basel
Original assignee: Chem Ind Basel
Priority date: 1936-12-23
Filing date: 1936-12-23
Publication date: 1940-07-31

Description

  

  Verfahren zur Darstellung einer Verbindung der     Nebennierenrindenhormonreihe.       Gegenstand des vorliegenden Patentes bil  det ein Verfahren zur Herstellung einer Ver  bindung der     Nebennierenrindenhormonreihe,     das dadurch gekennzeichnet ist, dass man       Desogycorticosteron    mit einem     n-butyrylie-          renden    Mittel behandelt.

      Die auf diese Weise gewonnene Verbin  dung hat die Formel       C21IEI29O3-Co    .<B>CH.'</B> .     CHZ    .     CH,     und besitzt die Struktur:  
EMI0001.0009     
    Diese Verbindung bildet farblose Kri  stalle, die bei 110 bis 111   schmelzen; sie  lässt sich aus     Aceton-Petroläther        umkristalli-          sieren.     



  Zur     n-Butyrylierung    eignen sich die be  kannten     Veresterungsmethoden.    Nur solche  Methoden, bei denen stark alkalische     Rea-          gentien    (wie freie Alkalien) benötigt wer  den, sind     entweder    mit grosser Vorsicht zu  benutzen oder ganz auszuschliessen. Bei Ver-         wendung    von Methoden, bei denen freie     Xi-          neralsäure    (z.

   B.     Chlorwasserstoffsäure)    auf  tritt, arbeitet man zweckmässig mit säure  bindenden Mitteln (tertiäre Basen,     galium-          carbonat        ete.).    Auch durch     LTmesterung    kann  das     Desoxycorticosteronbutyrat    dargestellt  werden. Gegebenenfalls arbeitet man     in    Ge  genwart von     Verdünnungsmitteln,    wie Äther,  Benzol, Aceton usw. An Stelle von reinem       Desogycorticosteron        können    als Ausgangs-      Stoffe auch Rohprodukte, die dieses enthal  ten, verwendet werden.  



  Die neue Verbindung soll therapeutische  Verwendung finden oder als Zwischenpro  dukt zur Herstellung von, therapeutischen  wertvollen Verbindungen dienen.  



  <I>Beispiel:</I>  Zu einer Lösung von 0,5 Teilen     Desoxy-          corticosteron    in     2,5    Teilen     Pyridin    wird  1 Teil     n-Buttersäureanhydrid    zugefügt. Man  lässt hierauf das Gemisch während mehreren  Stunden bei Raumtemperatur stehen. Das  durch Wasserzusatz zuerst ölig ausfallende.  bald jedoch     kristallisierende    Reaktionspro  dukt wird auf der     Nutsche    mit Wasser und  stark verdünnter Salzsäure gewaschen.

   Man  gewinnt so 0,56 Teile Desoxycorticosteron-ii-         butyrat,    die nach Umkristallisation aus     Ace-          toii-Petroläther    bei 110 bis 111   schmelzen  und ein spezifisches     Drehungsvermögen    von  
EMI0002.0012     
  
    [al <SEP> # <SEP> + <SEP> 177 <SEP>   <SEP> (in <SEP> Chloroform) <SEP> besitzen.       Man kann auch ohne säurebindendes Mit  tel arbeiten oder an Stelle des     Säureanhy-          drides    das     n-Buttersäurechlorid    verwenden.



  Method for representing a connection of the adrenal cortex hormone series. The subject of the present patent forms a process for the production of a connection of the adrenal cortex hormone series, which is characterized in that desogycorticosterone is treated with an n-butyrylating agent.

      The compound obtained in this way has the formula C21IEI29O3-Co. <B> CH. '</B>. CHZ. CH, and has the structure:
EMI0001.0009
    This compound forms colorless crystals that melt at 110 to 111; it can be recrystallized from acetone petroleum ether.



  The known esterification methods are suitable for n-butyrylation. Only those methods that require strongly alkaline reagents (such as free alkalis) are either to be used with great caution or to be excluded entirely. When using methods in which free mineral acid (e.g.

   B. hydrochloric acid) occurs, it is advisable to work with acid-binding agents (tertiary bases, galium carbonate, etc.). Deoxycorticosterone butyrate can also be prepared by esterification. If necessary, you work in the presence of diluents such as ether, benzene, acetone, etc. Instead of pure desogycorticosterone, raw products containing this can also be used as starting materials.



  The new compound is intended to find therapeutic use or serve as an intermediate product for the preparation of therapeutically valuable compounds.



  <I> Example: </I> 1 part of n-butyric anhydride is added to a solution of 0.5 part of deoxycorticosterone in 2.5 parts of pyridine. The mixture is then left to stand at room temperature for several hours. That which initially precipitates oily from the addition of water. Soon, however, the reaction product crystallizing is washed on the suction filter with water and very dilute hydrochloric acid.

   This gives 0.56 part of deoxycorticosterone i-butyrate, which, after recrystallization from acetoy petroleum ether, melts at 110 to 111 and has a specific rotation capacity of
EMI0002.0012
  
    [al <SEP> # <SEP> + <SEP> 177 <SEP> <SEP> (in <SEP> chloroform) <SEP>. It is also possible to work without an acid-binding agent or to use n-butyric acid chloride in place of the acid anhydride.

Claims

PATENT CLAIM Process for the production of a connection of the adrenal cortex hormone series, characterized in that desogycorticosterone is treated with an n-butyrylating agent. The compound obtained in this way has the formula C_1HII03-CO. CH2. CHz. CH3 and has the structure: EMI0002.0027 It forms colorless crystals that melt at 110 to 111.

It can be recrystallized from acetone petroleum ether. The new compound is intended to find therapeutic use or serve as an intermediate for the preparation of therapeutically valuable compounds. SUB-CLAIMS 1. The method according to claim, characterized in that n-butyric anhydride is used as the n-butyrylating agent. 9.

Method according to claim. characterized in that the n-butyryl halide is used as the n-butyryl halide. 3. The method according to claim, characterized in that an n-butyric acid ester is used as the n-butyric agent. 4th

Process according to patent claim, characterized in that the starting material is not pure desogycorticosterone, but raw products containing it are treated with n-butyrylating agents. 5. The method according to claim, characterized in that the n-Butyrylie- tion in the presence. of thinners. 6. The method according to claim, characterized in that the n-butylation is carried out in the presence of acid-binding agents. 7th

Process according to patent claim and sub-claim 5, characterized in that the n-butyrylation is carried out in the presence of acetone. B. The method according to patent claim and Un teran claim 6, characterized in that the n-butyrylation is carried out in the presence of pyridine.