CH204764A

CH204764A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204764A
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     1-Naphtogy-          butyrimidoäther    mit     Ammoniak        umsetzt.     



  Das so gewonnene     1-Naphtogybutenyl-          amidin.    der Formel  
EMI0001.0013     
    bildet ein     Hydrochlorid    vom F. 1:80 bis<B>181',</B>  das sich in Wasser löst.  



  Die neue Verbindung soll therapeutische       Verwendung    finden.  



       Beispiel:     Man     leitet        Salzsäuregae    in ein gekühltes       Gemiscb.        ä.quimolarer    Mengen von Alkohol  und     1-Naphtogybutyronitril        (gp.        o,4,    188     bis     186  ;

   hergestellt zum Beispiel durch Erhit  zen von     a-Naphtol    und     y-Chlorbutyronitril,            in    Gegenwart von säurebindenden Mitteln)  ein und verreibt das entstandene     1-Naphtogy-          butyrimidoäthyläth-er-hydroehlorid    mit einem       indifferenten        Lösungsmittel    wie     Petroläther,     Äther oder Benzol.

   Man erhält es so in     Form     eines farblosen, feuchtigkeitsempfindlichen       Kristallpulvers.   <B>29,8</B> Teile     1-Naphtogybutyr-          imidoäthyläther-hy.droehlorid,        aus    dem sich  während der Umsetzung     1-Naphtogybutyr-          imidoäthyläther    bildet, werden mit einer  alkoholischen     Lösung    von 8 Teilen Ammo  niak bis zum     Verschwinden    :

  des     zunächst     entstehenden     Ammonchlorids        geschüttelt.    ,So  dann     wird    der Alkohol     ahdestilliert    und der  Rückstand aus Alkohol oder Wasser     umkri-          stallisiert.    Man erhält so das 1-     Naphtogy-          butenyl    -     :amidin    -     hydroehlorid    als farbloses       Kristallpulver,    aus dem sich     mittels    Alkalien  die freie Base gewinnen lässt.  



  Statt von 1 -     Naphtogybutyrimidoäthyl-          äther    kann man ebensogut auch von einem  andern Äther, wie z. B. vom     Methyl-,        Pro-          pyl-    oder     Butyläther,    ausgehen.      An Stelle des     salz@sa.uren    Salzes     des        1-          Naphtoxybutyrimidoäthyläthers    kann auch  die freie Base selbst oder ein anderes Salz,  wie z. B. das     Hydrobromid    oder das     schwe-          felsaure    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 1-naphthogybutyrimido ether with ammonia.



  The 1-naphtogybutenyl amidine obtained in this way. the formula
EMI0001.0013
    forms a hydrochloride with a ratio of 1:80 to <B> 181 ', </B> which dissolves in water.



  The new compound should find therapeutic use.



       Example: Hydrochloric acid gas is fed into a chilled mixture. Equimolar amounts of alcohol and 1-naphtogybutyronitrile (gp. o, 4, 188 to 186;

   produced, for example, by heating α-naphtol and γ-chlorobutyronitrile, in the presence of acid-binding agents) and rubs the resulting 1-naphtogy-butyrimidoethyl ether hydrochloride with an inert solvent such as petroleum ether, ether or benzene.

   It is thus obtained in the form of a colorless, moisture-sensitive crystal powder. <B> 29.8 </B> parts of 1-naphtogybutyrimidoethyl ether-hy.droehlorid, from which 1-naphtogybutyrimidoethyl ether is formed during the reaction, are mixed with an alcoholic solution of 8 parts of ammonia until it disappears:

  of the ammonium chloride formed initially. The alcohol is then distilled off and the residue is recrystallized from alcohol or water. This gives 1-naphtogy-butenyl -: amidine - hydrochloride as a colorless crystal powder from which the free base can be obtained by means of alkalis.



  Instead of 1-naphtogybutyrimidoethyl ether, one can just as easily use another ether, such as e.g. B. from methyl, propyl or butyl ethers, start. Instead of the salz@sa.uren salt of 1-Naphtoxybutyrimidoäthyläthers, 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 1-naphthoxy butyrimido ether is reacted with ammonia. The 1-naphthoxybutenyl amidine of the formula obtained in this way EMI0002.0017 forms a hydrochloride from F. 180 to <B> 181 ', </B> which dissolves in water. The new compound should find therapeutic use.

SUBSTITUTE SPRü CHE 1. Process according to claim, characterized in that 1-naphthoxybutyrimidoethyl ether is used for the reaction. 2. The method according to patent claim, characterized in that a 1 - Naphtoxybutyrimidoäther is used for the implementation, which was obtained from a salt thereof. 3.

Process according to patent claim and un teran claim 2, characterized in that a 1-naphthoxybuty rimido ether is used for the reaction, which was obtained from a hydrohalide thereof. 4. The method according to patent claim and .den subclaims 2 and 3, characterized in that a 1-naphtoxybutyrimidoether is used for the implementation, which was obtained from the same .dem hydrochloride. 5.

Process according to patent claim and the dependent claims 1 to 4, characterized in that 1-naphthoxybutyrimidoä.thylä.ther is used for the reaction, which was obtained from the hydrochloride of the same.