CH204752A

CH204752A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204752A
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-Methogy-6-          allylphenogyacetimidoäther    mit Ammoniak  umsetzt.  



  Das so gewonnene 2     --lbiethogy    - 6 -     allyl-          phenogyäthenylamidin    der Formel  
EMI0001.0012     
    bildet ein     Flydrochlorid    vom F.     135    bis 137  ,  das sich in Wasser leicht löst.  



  Die neue Verbindung soll therapeutische       @lerwendung    finden.  



  <I>Beispiel:</I>  Man leitet     Salzsäuregas    in ein     gekühltes          Gemisch        äquimolarer    Mengen von Alkohol    und 2 -     Methogy    - 6 -     allyl    -     phienoayacetonitril     (KP, 127 bis 130  , hergestellt z.

   B.     durch     Umsetzung von     Chloracetonitril    mit     2-Meth-          ogy-6-allyl-phenol    in Gegenwart von säure  bindenden Mitteln) ein und verreibt das ent  standene     2-Methozy    - 6 -     allyl-phenogyacet-          imidoäthyläther-hydrochlorid    mit einem in  differenten     Lösungsmittel    wie     Petroläther,     Äther oder Benzol.

   Man erhält es so in Form  eines farblosen     Kristallpulvers.    28,5 Teile       2-Methogy    - 6 -     allyl-phenogyacetimidoäthyl-          äther-hydrochlorid,    aus dem     sich    während  der Umsetzung     2-Methogy-6-allyl-phenogy-          acetimidoäthylätlier    bildet, werden mit     einer     alkoholischen Lösung von 2,

  2     Teilen    Ammo  niak     bis    zum     Verschwinden    des zunächst ent  stehenden     Ammonchlorids        geschüttelt.    So  dann wird der Alkohol     abdestilliert        und,der     Rückstand aus     Aceton        umkristallisiert.    Man  erhält so     das        2-Methogy-6-allyl-plhenogyäthe-          nyla-midin-,hydrochlorid    als farbloses Kristall  pulver, aus dem sich     mittels    Alkalien die  freie Base     ,gewinnen    lässt.

        Statt von     2-Metlioxy-6-ally        1-phenoxyacet-          imidoäthyläther    kann man     ebensob    t auch  von einem andern Äther,     wie    z. B. vom       Methyl-,        Propyl-    oder     Butylä.ther,    ausgehen.  



  An Stelle des salzsauren Salzes des 2  Methoxy - 6 -     allyl    -     phenoxyacetimidoätliyl        -          äthers    kann auch die frei Base selbst oder  ein anderes .Salz -wie z. B. das     Hydrobromid     oder das     schwefelsaure    Salz Verwendung fin  den.



  Process for the preparation of a new therapeutically effective amidine. It has been found that a new therapeutically effective amidine can be obtained if a 2-methogy-6-allylphenogyacetimido ether is reacted with ammonia.



  The 2 -lbiethogy-6-allyl-phenogyäthenylamidin of the formula obtained in this way
EMI0001.0012
    forms a flydrochloride with a temperature of 135 to 137, which dissolves easily in water.



  The new connection should find therapeutic application.



  <I> Example: </I> Hydrochloric acid gas is passed into a cooled mixture of equimolar amounts of alcohol and 2 - methogy - 6 - allyl - phienoayacetonitrile (KP, 127 to 130, produced e.g.

   B. by reacting chloroacetonitrile with 2-methogy-6-allyl-phenol in the presence of acid-binding agents) and rubs the 2-methozy-6 - allyl-phenogyacet- imidoethyl ether hydrochloride with a different solvent like Petroleum ether, ether or benzene.

   It is obtained in the form of a colorless crystal powder. 28.5 parts of 2-methogy-6-allyl-phenogyacetimidoethyl ether hydrochloride, from which 2-methogy-6-allyl-phenogyacetimidoethyl ether is formed during the reaction, are mixed with an alcoholic solution of 2,

  2 parts of ammonia are shaken until the ammonia chloride initially formed disappears. The alcohol is then distilled off and the residue is recrystallized from acetone. This gives the 2-methogy-6-allyl-plhenogyäthenyla-midin-, hydrochloride as a colorless crystal powder from which the free base can be obtained by means of alkalis.

        Instead of 2-Metlioxy-6-ally 1-phenoxyacet- imidoethylether one can also use another ether, such as e.g. B. from methyl, propyl or butyl ether, start.



  Instead of the hydrochloric acid salt of 2 methoxy - 6 - allyl - phenoxyacetimidoätliyl - ether can also be the free base itself or another .Salz - such as. B. the hydrobromide or the sulfuric acid salt use fin the.

Claims

PATENT CLAIM: Process for the production of a new therapeutically effective amidine, characterized in that a 2-112ethoxy-6-allyl-phenoxya.cetimidoether is reacted with ammonia. The 2-methoxy-6-al.lyl-phenoxyethenylamidine of the formula obtained in this way EMI0002.0021 forms a hydrochloride with a melting point of 135 to 137, which dissolves easily in water. The new compound should find therapeutic use. SUBClaims 1.

Method according to patent claim, characterized. da.ss to implement 2-lfethoxy -6-ally 1-phenoxyacetimidoethyl Ä.ther used. 2. The method according to claim, characterized in that a 2 - methoxy - 6 - allyl - plienoxyacet imido ether is used for the reaction, which was obtained from a salt thereof.

Ä. Method according to patent claim and Untera.nspruch?, characterized in that a 2-methoxy-6-allyl-plienoxy acetimido ether is used for the reaction. which was obtained from a Hydroha.lob nid of the same. 4th

Method according to claim and the dependent claims 2 and 3, characterized in that one? - Methoxy - 6 - allyl - phenoxyacet imidoätlier used, which was obtained from the hydrochloride of the same.

Process according to patent claim and the dependent claims 1 to 4, characterized in that for the reaction? -: @ fethoxy-6-allyl-plienoxyacetimidoethyl ether is used, which was obtained from the hydrochloride of the same.