CH204758A

CH204758A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204758A
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,     da.B    man zu einem  neuen therapeutisch     wirksamen        Amidin    ge  langen kann, wenn man einen     Phenoxyacet-          imidoäther    mit     ss-Phenyläthylamin    umsetzt.  



  Das so .gewonnene     Ph-enoxyäthenyl    -     ss        -          phenyläthyl-amidin    der Formel  
EMI0001.0013     
    bildet ein Hydrochlorid vom F. 2'01     bis   <B>2103',</B>       das    sich in     Wasser    löst.  



       Die    neue Verbindung soll     therapeutische          @Terwendung    finden.  



  <I>Beispiel:</I>  Man     leitet        Salzsäuregas    in eingekühltes  Gemisch     äquirnolarer    Mengen von Alkohol  und     Phenoxyacetonitril    ein und verreibt     das          entstandene        Phsnoxya@cetimidoäthyläther-hy-          drochlorid    mit einem     indifferenten    Lösungs  mittel, wie     Petroläther,    Äther oder Benzol.

      Man erhält es in Form eines farblosen, feuch  tigkeitsempfindlichen     Kristallpulvers.    21,5  Teile     Phenoxyacetimidoäthyläther=hydrochlo-          ri@d,    .aus dem sich während der     Umsetzung          Phenoxyacetimidoäthyläther    bildet, werden  mit     einer    alkoholischen     Lösung    von 12 Tei  len     ss-Phenyläthylamin    .geschüttelt.

       'Sodann          wird    der Alkohol     abdestilliert        und,der    Rück  stand aus     Aceton        umkristallisiert.    Man er  hält .so das     Ph@enoxyäthenyl-ss-phenyläthyl-          amidin-hydrochlord    als     farbloses        Kristall-          pulver,    aus dem sich     mittels    Alkalien die  freie Base gewinnen     läBt.     



       Matt    von     Phenoxyacetimidoäthyläther     kann man     ebensogut    auch von einem andern  Äther,     wie    z. B. vom     Methyl-,        Propyl-    oder       BLityläth,er,        ausgehen.     



  An     Stelle    des     salzsauren    Salzes ,des     Phen-          oxya,cetimidoäbhyläthers    kann auch die freie  Base selbst oder ein anderes Salz wie z. B.  .das     Hydrobromid    oder das     s.chwefel@saure     Salz     Verwendung    finden.



  Process for the preparation of a new therapeutically effective amidine. It was found that a new therapeutically effective amidine can be obtained by reacting a phenoxyacetimido ether with β-phenylethylamine.



  The so .gewonnene Ph-enoxyäthenyl - ss - phenylethyl-amidine of the formula
EMI0001.0013
    forms a hydrochloride from F. 2'01 to <B> 2103 ', </B> which dissolves in water.



       The new connection should find therapeutic application.



  <I> Example: </I> Hydrochloric acid gas is introduced into a cooled mixture of equimolar amounts of alcohol and phenoxyacetonitrile and the resulting Phsnoxya @ cetimidoethyl 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. 21.5 parts of phenoxyacetimidoethyl ether = hydrochloride, from which phenoxyacetimidoethyl ether is formed during the reaction, are shaken with an alcoholic solution of 12 parts of β-phenylethylamine.

       'Then the alcohol is distilled off and the residue was recrystallized from acetone. The phenoxyethenyl-β-phenylethylamine hydrochloride is obtained as a colorless crystal powder from which the free base can be obtained by means of alkalis.



       Matt from Phenoxyacetimidoäthyläther can just as well from another ether, such as z. B. from methyl, propyl or BLityläth, he, go out.



  Instead of the hydrochloric acid salt, the phenoxy, cetimidoäbhyläthers, the free base itself or another salt such as. B. the hydrobromide or the s.chwefel@saure Salz can be used.

Claims

PATENT CLAIM: Process for the production of a new therapeutically effective amidines, characterized by the fact that a Plienoxya.cet- imidoätlier is converted with ss-Pheny läthy lamm. The so obtained Plienoxyätheriyl - pheny läthyl-amidin of the formula EMI0002.0016 EMI0002.0017 forms <SEP> a <SEP> Hvdi-oclilorid <SEP> from <SEP>

F. <SEP> 201. <SEP> to <SEP>? 0.3 <SEP>, <tb> the <SEP> <SEP> dissolves in <SEP> water <SEP>. <tb> The <SEP> new <SEP> connection <SEP> should <SEP> therapeutic marriage <tb> Find use <SEP>. <tb> SUBClaims: <tb> 1. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> that <SEP> is used <SEP> for <SEP> Phenoxy <SEP> acetimido ethyl ether <SEP>. <tb> 2. <SEP> method <SEP> according to <SEP> patenta, nsprueh, <SEP> thereby <tb> gekennzeiolinet, <SEP> da.ss <SEP> one <SEP> uses a phenoxyacetimido ether for <SEP> conversion.

obtained from a salt thereof. a. Process according to patent to: spi-ucli und Un- ieransprueli ?, characterized in that a phenoxyacetimido ether is used for the reaction, which was obtained from a hydrohalide of the same. 4th

Method according to patent claim and the subclaims? and 3, characterized in that a Pbenoxyacetimido, ither is used for the reaction, which was obtained from the hydrochloride of the same.

Process according to patent claim and Unierarispriichen 1 to 4, characterized in that phenoxy, cetinidoethyl ether obtained from the hydrochloride of the same is used for the reaction.