CH204754A

CH204754A - Process for the preparation of a new therapeutically effective amidine.

Info

Publication number: CH204754A
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-          oxyaeetimidoäther    mit Ammoniak umsetzt.  



  Das so gewonnene     Chinolin-8-oxyäthenyl-          amidin    der Formel  
EMI0001.0011     
    bildet     ein        Hydrochlorid    vom F. 204', das  sich in Wasser leicht löst.  



  Die neue Verbindung soll     therapeutische     Verwendung finden.  



  <I>Beispiel:</I>  Man     leitet,Salzsäurega.s    in ein     ,gekühltes     Gemisch     äquimolarer    Mengen von Alkohol  und     Chinolin-8-oxyacetanitril    (F.     l292',    her  gestellt zum Beispiel durch Umsetzung von       Chloracetonitril    mit     8-Oxychinolin    in Gegen-    wart von säurebindenden Mitteln) ein und  verreibt .das     entstandene        Chinolin-8-oxyacet-          imidoäthyläther-hydrochlorid    mit einem in  differenten     Lösungsmittel,    wie     Petroläther,     Äther oder Benzol.

   Man erhält es so in Form  eines farblosen     Kristallpulvers.    30     Teile          Chinolin    - 8 -     oxyacetimidoäthyläther    -     hydro,          chlorid,    aus dem sich während der Umset  zung     Chinälin-8-oxyacetimidoäthyläther    bil  det,     werden;    mit     einer        alkoholischen        Lösung     von 4 Teilen Ammoniak geschüttelt.

   Sodann  wird der Alkohol     abdestilliert    und -der Rück  stand aus Aceton     umkristallisiert.    Man er  hält so .das     Chinolin    - 8 -     oxyäthenylamidin-          hydrochlorid    als farbloses     Kristallpulver,    aus  dem sich mittels Alkalien die freie Base ge  winnen lässt. .  



  Statt von     Chinolin=8-oxyacetimidoäthyl-          äther    kann man     ebensogut    auch von einem  andern Äther, wie z. B. vom     Methyl-,        Pro-          pyl-    oder     Butyläther,    ausgehen.  



  An Stelle des salzsauren Salzes. des     Chino-          lin-8-oxyacetimidoäthyläthens    kann auch die      freie Base selbst oder ein anderes Salz, wie  z. B. das     Hydrobromid    oder das schwefel  saure 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-oxyaeetimido ether with ammonia.



  The quinoline-8-oxyäthenyl- amidine of the formula obtained in this way
EMI0001.0011
    forms a hydrochloride of F. 204 ', which dissolves easily in water.



  The new compound should find therapeutic use.



  <I> Example: </I> Hydrochloric acid is poured into a cooled mixture of equimolar amounts of alcohol and quinoline-8-oxyacetanitrile (F. 1292 ', produced for example by reacting chloroacetonitrile with 8-oxyquinoline in counter - waited for acid-binding agents) and rubbed the quinoline-8-oxyacet- imidoethyl ether hydrochloride formed with a different solvent, such as petroleum ether, ether or benzene.

   It is obtained in the form of a colorless crystal powder. 30 parts of quinoline - 8 - oxyacetimido ethyl ether - hydro, chloride, from which quinoline 8-oxyacetimido ethyl ether is formed during the implementation; shaken with an alcoholic solution of 4 parts of ammonia.

   The alcohol is then distilled off and the residue is recrystallized from acetone. The quinoline-8-oxyethenylamidine hydrochloride is obtained as a colorless crystal powder from which the free base can be obtained by means of alkalis. .



  Instead of quinoline = 8-oxyacetimidoethyl ether, one can just as easily use another ether, such as e.g. B. from methyl, propyl or butyl ethers, start.



  Instead of the hydrochloric acid salt. of the quinoline-8-oxyacetimidoäthyläthens can also be 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-oxyacetimidoether is reacted with ammonia. Cliinolin-8-oxy-ethene-1-amidine of the formula obtained in this way EMI0002.0013 forms a Hydroehloild from F. '-) 04', which dissolves easily in water. The new compound should find therapeutic use. <B> SUBClaims </B> 1.

Process according to patent claim, da.durcli characterized in that quinoline-8-oxyaeetimidoethyl ether is used for the reaction. \ ?. Method according to claim, characterized in that aekennzeiclinet. that one uses a quinoline - 8 - oxvacetimidoether which was obtained from a salt of the same for the implementation.

a. - \ 'experienced according to patent claim, and sub-claims, characterized in that a quinoline-8-oxyacetimido ether is used for the implementation, which was obtained from a hydrohalide of the same.

.k. Method according to patent claim and the dependent claims \? and 3, characterized thereby. that a quinoline - 8 - oxyacetimidoether is used for the reaction, which was obtained from the hydrochloride of the same.

@. Process according to patent claim and sub-claims 1 to -1, characterized in that quinoline-8-oxyacetimidoethyl ether obtained from the hydrochloride of the same is used for the reaction.