CH285028A - Process for the preparation of a pyrimidylaminoquinoline derivative. - Google Patents

Process for the preparation of a pyrimidylaminoquinoline derivative.

Info

Publication number
CH285028A
CH285028A CH285028DA CH285028A CH 285028 A CH285028 A CH 285028A CH 285028D A CH285028D A CH 285028DA CH 285028 A CH285028 A CH 285028A
Authority
CH
Switzerland
Prior art keywords
amino
pyrimidyl
preparation
aniino
pyrimidylaminoquinoline
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ici Ltd filed Critical Ici Ltd
Publication of CH285028A publication Critical patent/CH285028A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     Pyrimidylaminochinolinderivates.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Herstellung von       4-Amino-6-        (2'-aniino-pyrimidyl    -     4'-aniino)        -chi-          riolin-1,1'-dimethochlorid.     



  Es wurde gefunden, dass dieses     4-Aniino-          6-        (2'-äniino-pyriniid.yl-4'-aniino)    -     chinolin        -1,1'-          dimethoehlorid    wertvolle     try        panozide    Eigen  schaften aufweist,     insofern    als bei dessen sub  kutaner     Verabreiehung    an mit.

       Trypanosolna          congolense    infizierte     Mäuse    in einer Dosis von       1,25        mg        pro        kg        -Hausgewicht        eine        100        %        ige          1-leilunn-    der Mäuse von der     Trypariosomiasis     erzielt     wird,    ohne dass dabei ein ernstlicher  lokaler oder allgemeiner,

   sofortiger oder     ver-          zögerter    toxischer Effekt in Erscheinung tritt..  



       Das        erfindungsgemässe        Verfahren    zur Her  stellung von     4-Aniino-6-(2'-aniino-pyrimidyl-          4'-aniino)-eiiinolin-1,1'-diinethoelilorid    ist-     da-           < hircll    gekennzeichnet, dass     inan        4-Aiiiino-6-(2'-          ainino-pyriniidyl-4'-aniino)-chinolin    mit     Me-          tliyichlorid    zur Reaktion bringt.  



  Die Reaktion kann durch Erhitzen der     ver-          einigteli        Reaktionskomponenten,        zweckiuässi-          gerweise    in einem Lösungsmittel, wie z. B.       3thylalkohol,        Acetonit.ril    oder     Nitrobenzol,     a     asgeführt    werden.  



  Die     Erfindung    wird durch das folgende  Beispiel erläutert;      Teile     bezeichnen     Ge-          wiclitsteile.     



       Beispiel:     o Teile     4-Amino-6-(2'-aniilio-pyrimidyl-4'-          iiniino)-eliinolin,    1,2 Teile     Methylehlorid    und    18 Teile Methylalkohol werden zusammen in  einem geschlossenen Reaktionsgefäss während  24 Stunden bei 120 bis 130  C erhitzt. Das Ge  misch wird abgekühlt und filtriert.

   Der feste       Rückstand        wird        aus        50        %        igem        wässerigem          Ethanol    kristallisiert, wobei 4     Amino-6-(2'-          amino-pyrimidyl-4'-amino)        -chinolin-1,1'    -     dime-          thochlorid    in Form farbloser Nadeln vom       Smp.        34t7     C (Zersetzung) erhalten wird.



  Process for the preparation of a pyrimidylaminoquinoline derivative. The present invention relates to a process for the preparation of 4-amino-6- (2'-aniino-pyrimidyl-4'-aniino) -chiriolin-1,1'-dimethochloride.



  It has been found that this 4-aniino-6- (2'-aeniino-pyriniid.yl-4'-aniino) -quinoline -1,1'-dimethoehlorid has valuable try panozide properties, insofar as when it is administered subcutaneously on with.

       Trypanosolna congolense infected mice in a dose of 1.25 mg per kg -house weight a 100% 1-leilunn- the mice of the trypariosomiasis is achieved without a serious local or general,

   immediate or delayed toxic effect occurs.



       The process according to the invention for the preparation of 4-aniino-6- (2'-aniino-pyrimidyl-4'-aniino) -eiiinolin-1,1'-diinethoeliloride is characterized in that inan 4-aiiiino-6 - (2'-ainino-pyriniidyl-4'-aniino) -quinoline reacts with metal chloride.



  The reaction can be carried out by heating the combined reaction components, expediently in a solvent, e.g. B. 3thylalkohol, Acetonit.ril or Nitrobenzol, a as lead.



  The invention is illustrated by the following example; Parts refer to weight parts.



       Example: o parts of 4-amino-6- (2'-aniilio-pyrimidyl-4'-iiniino) -eliinoline, 1.2 parts of methyl chloride and 18 parts of methyl alcohol are heated together in a closed reaction vessel at 120 to 130 ° C. for 24 hours . The mixture is cooled and filtered.

   The solid residue is crystallized from 50% aqueous ethanol, with 4 amino-6- (2'-aminopyrimidyl-4'-amino) -quinoline-1,1'-dimethochloride in the form of colorless needles with a melting point of 34 ° 7 C (decomposition) is obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 4-Amino- 6- (2'-amino-pyrimidyl-4'-amino) - chinolin-1,1'- dimethochlorid, dadurch gekennzeichnet, dass man 4-Amino-6-(2'-amino-pyrimidyl-4'-amino)- ehinolin mit Methylchlorid zur Reaktion bringt. Claim: Process for the production of 4-amino-6- (2'-amino-pyrimidyl-4'-amino) -quinoline-1,1'-dimethochloride, characterized in that 4-amino-6- (2'- Amino-pyrimidyl-4'-amino) - ehinoline reacts with methyl chloride. 4-Amino - 6- (2'-amino-pyriniidyl-4'-amino) - ehinolin-1,1'-dim.ethochlorid ist ein farbloses, kristallisiertes, festes Produkt vom Smp. 340 C (Zersetzung). 4-Amino - 6- (2'-aminopyriniidyl-4'-amino) - ehinolin-1,1'-dim.ethochlorid is a colorless, crystallized, solid product with a melting point of 340 ° C. (decomposition). Es besitzt wertvolle try- panozide Eigenschaften und bewirkt bei sub kutaner Verabreichung an mit Trypanosoma eongolense infizierte Mäuse in einer Dosis von 1,25 mg pro kg Mausgewicht eine 1.OOo/oige Heilung der Mäuse von der Trypanosolniasis, wobei kein ernstlicher lokaler oder allgemeiner, sofortiger oder verzögerter toxischer Effekt in Erseheinung tritt. It has valuable trypanocidal properties and when administered subcutaneously to mice infected with Trypanosoma eongolense at a dose of 1.25 mg per kg mouse weight, the mice are cured from trypanosolniasis 1,000 times over, with no serious local or general, immediate or delayed toxic effect occurs.
CH285028D 1947-08-22 1948-08-21 Process for the preparation of a pyrimidylaminoquinoline derivative. CH285028A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB285028X 1947-08-22
GB285026X 1947-08-22

Publications (1)

Publication Number Publication Date
CH285028A true CH285028A (en) 1952-08-15

Family

ID=32964143

Family Applications (1)

Application Number Title Priority Date Filing Date
CH285028D CH285028A (en) 1947-08-22 1948-08-21 Process for the preparation of a pyrimidylaminoquinoline derivative.

Country Status (1)

Country Link
CH (1) CH285028A (en)

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