CH204766A

CH204766A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204766A
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-Oxy-phenoxy-          acetimidoäther    mit Ammoniak     umsetzt.     



       Das    so gewonnene     2-Oxy-phenoxyäthenyl-          amidin    der     Formel     
EMI0001.0014     
    bildet ein Hydrochlorid vom F. 190 bis<B>191',</B>       das        sich    in Wasser löst.  



  Die neue Verbindung soll     therapeutische          Verwendung    finden.  



  <I>Beispiel:</I>  Man leitet     Salzsäuregas    bei Zimmertem  peratur     in    ein Gemisch     äquimolarer    Mengen  von Alkohol und     2-Benzyloxy-phenoxyace-          tonitril    (F.

   92  , hergestellt zum Beispiel  durch Umsetzung von     Chloracetonitril    mit       Brenzeatechinmonobenzyläther,    in -Gegen-    wart von .säurebindenden     Mitteln)        ein    und  verreibt das entstandene     2-Oxyphenoxyacet-          imidoäthyläther-hydrochlorid    mit einem in  differenten     Lösungsmittel    wie     Petroläther,     Äther oder     Benzol.    Man erhält     :

  es    so in Form  eines farblosen,     feuchtigkeitsempfindlichen          Kristallpulvers.    23 Teile     2-Oxy-phenoxyacet-          imidoäthyläther-hydrochloräd,    aus dem sich  während der Umsetzung     2-Ogy-phenogya@cet-          imidoäthyläther    bildet, werden mit einer  alkoholischen Lösung von 2,2 Teilen Ammo  niak     bis    zum Verschwindendes     zunächst    ent  stehenden     Ammonebl:

  orids        .geschüttelt.    So  dann     wird    der Alkohol     abdestilliert    und der  Rückstand mit Aceton     anisgekocht,    wobei     das          2-0%y    -     phenoxyäthenylam@idin    -     hydrochlorid     als farbloses Kristallpulver e     rhalten    wird.  



  Statt von     2-Ogy-phenogyacetimidoäthyl-          äther    kann man     ebensöb,'ut    auch von     einem     andern     Äther,    wie z. B. vom     Methyl-,    Pro  pyl- oder     Butyläther,    ausgehen.  



  An Stelle     .des    salzsauren     @alzes.des        2-Oxy-          phenoxyacetimidoäthyläthers        kann    auch die      freie Base selbst oder ein anderes Salz wie  z. B. das     Hydrobromid    oder das schwefel  saure Salz     Verwendunb    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-oxy-phenoxy-acetimido ether with ammonia.



       The 2-oxy-phenoxyethenyl amidine of the formula obtained in this way
EMI0001.0014
    forms a hydrochloride from F. 190 to <B> 191 ', </B> which dissolves in water.



  The new compound should find therapeutic use.



  <I> Example: </I> Hydrochloric acid gas is passed at room temperature into a mixture of equimolar amounts of alcohol and 2-benzyloxyphenoxyacetonitrile (F.

   92, produced, for example, by reacting chloroacetonitrile with brenzeatechin monobenzyl ether, in the presence of acid-binding agents) and rubbed the 2-oxyphenoxyacetimidoethyl ether hydrochloride with a different solvent such as petroleum ether, ether or benzene. You get     :

  it is in the form of a colorless, moisture-sensitive crystal powder. 23 parts of 2-oxy-phenoxyacet- imidoäthyläther-hydrochlorad, from which 2-Ogy-phenogya @ cet- imidoäthyläther is formed during the reaction, are mixed with an alcoholic solution of 2.2 parts of ammonia until the ammonia initially formed disappears:

  orids .shaken. The alcohol is then distilled off and the residue is anise-boiled with acetone, the 2-0% γ-phenoxyethenylamine hydrochloride being obtained as a colorless crystal powder.



  Instead of 2-Ogy-phenogyacetimidoethyl ether one can also use another ether, such as B. from the methyl, propyl or butyl ether, proceed.



  Instead of .des hydrochloric acid @ alzes.des 2-Oxy- phenoxyacetimidoethyl ether, the free base itself or another salt such as. B. find the hydrobromide or the sulfuric acid salt use.

Claims

PATENT CLAIM: Process for the production of a new therapeutically effective Amidinee, characterized in that a 2-oxy-phenoxyacetimidoether is reacted with ammonia. The 2-oxy-phenoxyätlienyl- amidine of the formula obtained in this way EMI0002.0011 forms a hydrochloride from F. 190 to <B> 191 ', </B> which dissolves in water. The new compound should find therapeutic use.

UN TERAN SPRMHE 1. Process according to patent claims, characterized in that 2-oxy-phenoxyacetimidoethyl ether is used for the reaction. ?, Method according to claim, characterized in that

that a? -Oxy-plienoxyacetimidoä.ther is used for the implementation, which was obtained from a salt thereof. 3. Method according to patent claim and sub-claim? characterized in that a 2-Oxy- phenoxyacetimidoätlier is used for the reaction, which was obtained from a hydrohalide of the same. 4th

Process according to claim and the dependent claims 2 and 3, characterized in that a 2-oxy-plienoxyac.etimidoether is used for the reaction, which was obtained from the hydrochloride thereof ben. 5. The method according to claim and the dependent claims 1 to 4, characterized in that 9-Oxy- plieiioxyacetimidoii.tliylätlierus used for the implementation, which was obtained from the Hv droclilorid thereof.