CH204762A

CH204762A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204762A
Authority: CH
Inventors: Gesellschaft Fuer Chemis Basel
Original assignee: Chem Ind Basel
Priority date: 1935-06-21
Filing date: 1935-06-21
Publication date: 1939-05-15

Description

  

      Verfahren    zur Herstellung eines neuen therapeutisch wirksamen     Amidines.       Es wurde gefunden, dass man zu     einem     neuen     therapeutisch        wirksamen        Amidin    ge  langen kann,     wenn    man     einen        2-Naphtogy-          acetimidoäther    mit Ammoniak umsetzt.  



       Das    so gewonnene 2 -     Naphtogyäthenyl-          amidin    .der Formel  
EMI0001.0014     
    bildet ein Hydrochlorid vom F. 211  ,     das     sieh in     Wasser    löst.  



  Die neue Verbindung soll     therapeutische          Verwendung    finden.  



       Beispiel:     Man     leitet        SalzsäuTegas    in ein     gekühltes     Gemisch     äquimolarer    Mengen von Alkohol  und     ),-Naphtogyacetonitril    ein und verreibt  das entstandene 2 -     Naphtogyacetimidoäthyl-          äther-hydrochlorid        mit        einem        indifferenten          Lösungsmittel    wie     Petroläther,    Äther oder  Benzol.

       Man    erhält es so in Form eines farb-         losen,        feuchtigkeitsempfindlichen        Kristall-          pulvers.    26,5 Teile 2 -     Naphtogyacetimido-          äthyläther-hydrochlorid,    aus dem sich wäh  rend der     Umsetzung    2 -     Naphtogyacetimido-          äthyläther    bildet,

   werden mit     einer    alkoholi  schen Lösung von     ä        Teilen        Ammoniak        bis     zum     Verschwinden    des     zunächst        entstehen-          .den        Ammonchloride        geschüttelt.    Sodann     wird     .der Alkohol     abdestilliert    und der     Rückstand     aus     wässrigem    Aceton     umkristallisiert.    Man  erhält so     .das    2 -     

  Naphtogyäthpnylamidiu-          hydrochlorid    als farbloses     Kristallpulver,    aus  dem sich     mittels        Alkalien,die    freie     Base    ge  winnen lässt.  



       Statt    von     2-Naphtogyacetimidoäthyläther     kann man ebensogut auch von einem     andern     Äther, wie z. B. vom     Methyl-,        Propyl-    oder       Butyl.äther,    ausgehen.  



  An Stelle des     salzsauren        Salzes        ,des        2-          1\Taphtogyacetimidoätbyläthers        kann    auch     die     freie Base selbst oder     ein    anderes Salz,     wie     z. B. das     Hydrobromid    oder das schwefel  saure     ,Salz        Verwendung    finden.



      Process for the preparation of a new therapeutically effective amidine. It has been found that a new therapeutically effective amidine can be obtained by reacting a 2-naphtogyacetimido ether with ammonia.



       The 2 - naphtogyäthenyl amidine obtained in this way. Of the formula
EMI0001.0014
    forms a hydrochloride of F. 211, which dissolves in water.



  The new compound should find therapeutic use.



       Example: Hydrochloric acid gas is introduced into a cooled mixture of equimolar amounts of alcohol and), - naphtogyacetonitrile and the resulting 2 - naphtogyacetimidoethyl ether hydrochloride is rubbed with an inert solvent such as petroleum ether, ether or benzene.

       It is obtained in the form of a colorless, moisture-sensitive crystal powder. 26.5 parts of 2 - naphtogyacetimido ethyl ether hydrochloride, from which during the reaction 2 - naphtogyacetimido ethyl ether is formed,

   are shaken with an alcoholic solution of parts of ammonia until the ammonia chloride initially formed disappears. The alcohol is then distilled off and the residue is recrystallized from aqueous acetone. So you get the 2 -

  Naphtogyäthpnylamidiu- hydrochloride as a colorless crystal powder from which the free base can be obtained by means of alkalis.



       Instead of 2-Naphtogyacetimidoäthyläther you can just as well from another ether, such as z. B. from the methyl, propyl or Butyl.äther, proceed.



  Instead of the hydrochloric acid salt, the 2- 1 \ Taphtogyacetimidoätbyläthers can also the free base itself or another salt, such as. B. the hydrobromide or the sulfuric acid, salt are used.

Claims

PATENT CLAIM: Process for the production of a new therapeutically effective amidine, characterized in that a 2-naphthoxy-aoetimidoether is reacted with ammonia. The 2 - naphthoxyethenyl amidine of the formula obtained in this way EMI0002.0010 forms a hydrochloride of F. 211 'which dissolves in water. The new compound should find therapeutic use.

SUBClaims 1. Process according to claim, characterized in that 2-naphthoxyacetimidoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a 2 - Naphtoxyacetimidoäther is used for the implementation, which was obtained from a salt thereof th.

a. Process according to patent claim and un teran claim 2, characterized in that a 2-naphthoxyacetimido ether is used for the reaction, which was obtained from a hydrohalide of the same. 4 .. Method according to claim and the dependent claims 2 and 3;

characterized by the fact that to implement a? - Naphtoxyaoetimidoäther used, which was obtained from the same hydrochloride. 5. The method according to claim and the dependent claims 1 to 4, characterized .gekenn that one uses naphtoxyacetimidoethyl ether for the implementation, which he was keeping from the hydrochloride of the same.