CH204755A

CH204755A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204755A
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     Chinolin-8-          oxy-n-butyrimidoäther    mit Ammoniak um  setzt.  



  Das so     gewonnene        Chinolin-8-oxy-n-bute-          nylamidin    der Formel  
EMI0001.0011     
    bildet     ein.    Hydrochlorid vom F. 248  , das       sieh    in Wasser leicht löst.  



  Die neue     Verbindung    soll therapeutische       Verwendung    finden.  



  <I>Beispiel:</I>  Man leitet     @Salzsäuregas        in    ein gekühltes  Gemisch     äquimolarer    Mengen von Alkohol  und     Chinolin-8-oxybutyronitril    (F. 66 bis  67  ,     hergestellt    zum Beispiel durch Umset-         zung    von y -     Chlorbutyronitril        mit    8 -     Oxy-          ohinolin    in Gegenwart von säurebindenden  Mitteln)

   ein und verreibt     das        entstandene          Chiolin        -8-oxy-n-butyrimidoäthyläther-hydro-          ohlorid    mit einem indifferenten     Lösungsmit-          tel,    wie     Petroläther,    Äther oder Benzol.

   Man  erhält es so in Form     eines    farblosen     Kristall-          pulvers.    33 Teile     Cbinolin-8-oxy-n-butyr-          imidoäthyläther-hy        drochlorid,        aus    dem sich       während    der Umsetzung     Chinolin-8-oxy-n-          butyrimidoäthyläther    bildet,

   werden mit  einer alkoholischen     Lösung    von 4     Teilen     Ammoniak     geschüttelt.        Sodann    wird der  Alkohol     abdestilliert        und    der     Rückstrand    aus  wenig     Wasser        umkristallisiert.    Man erhält so  das     Chinolin-8-oxy-n-butenylamidin-hydro-          ,chlorid    als farbloses Kristallpulver,     aus    dem  sich     mittels    Alkalien ,

  die freie     Base        .gewinnen          läBt.     



       Statt    von     Chinolin    - 8 -     oxy    - n -     butyrimido-          ätliyIäther    kann man ebensogut auch von  einem andern Äther,     wie    z. B. vom     Methyl-,          Propyl-    oder     Butyläthier"ausgehen.         An Stelle des     salzsauren        Salzes        des        Chino-          lin-8-oxy-n-butyrimidoäthyläthers    kann man  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 quinoline-8-oxy-n-butyrimido ether with ammonia.



  The quinoline-8-oxy-n-butenylamidine of the formula obtained in this way
EMI0001.0011
    forms a. Hydrochloride of F. 248, which easily dissolves in water.



  The new compound should find therapeutic use.



  <I> Example: </I> @ Hydrochloric acid gas is passed into a cooled mixture of equimolar amounts of alcohol and quinoline-8-oxybutyronitrile (F. 66 to 67, produced for example by the reaction of γ-chlorobutyronitrile with 8-oxy- ohinolin in the presence of acid-binding agents)

   and rub the resulting chiolin -8-oxy-n-butyrimidoethyl ether hydrochloride with an inert solvent such as petroleum ether, ether or benzene.

   It is obtained in the form of a colorless crystal powder. 33 parts of Cbinolin-8-oxy-n-butyr- imidoäthyläther-hydrochloride, from which quinoline-8-oxy-n-butyrimidoethylether is formed during the reaction,

   are shaken with an alcoholic solution of 4 parts of ammonia. The alcohol is then distilled off and the back beach is recrystallized from a little water. This gives the quinoline-8-oxy-n-butenylamidine hydrochloride as a colorless crystal powder, from which, by means of alkalis,

  the free base can be obtained.



       Instead of quinoline-8-oxy-n-butyrimido-ätliyIäther one can just as well also from another ether, such as z. B. from the methyl, propyl or butyl ethers "proceed. Instead of the hydrochloric acid salt of quinoline-8-oxy-n-butyrimido ethyl ether, 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 quinoline-8-oxy-n-butyrimidoether is crosslinked with ammonia. The quinoline - 8 - oxy - n-butenylamidine of the formula obtained in this way EMI0002.0022 forms a hydrochloride of F. 248, which dissolves easily in water. The new compound should find therapeutic use.

SUBClaims: 1. Process according to claim, characterized in that quinoline-8-oxy-n-buty rimido ethyl ether is used for the reaction. \ ?. Process according to patent claim, characterized in that a quinoline-8-oxy-n-butyrimidoether is used for the reaction, which was obtained from a salt thereof. 3.

Process according to patent claim and sub-claim 2), characterized in that a quinoline-8-oxy-n-butyrimido ether is used for the reaction, which was obtained from a hydrohalide thereof.

Process according to patent claim and the independent claims 2 and 3, characterized in that a quinoline-8-oxy-n-butyrimido ether obtained from the hydrochloride of the same is used for the reaction. 5.

Process according to patent claim and the dependent claims 1 to 4, characterized in that quinoline-8-oxy-n-butyrimidoethyl ether obtained from the hydrochloride of the same is used for the reaction.