CH285020A - Process for the preparation of a pyrimidylaminoquinoline derivative. - Google Patents

Process for the preparation of a pyrimidylaminoquinoline derivative.

Info

Publication number
CH285020A
CH285020A CH285020DA CH285020A CH 285020 A CH285020 A CH 285020A CH 285020D A CH285020D A CH 285020DA CH 285020 A CH285020 A CH 285020A
Authority
CH
Switzerland
Prior art keywords
amino
quinaldine
preparation
pyrimidyl
methyl
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 CH285020A publication Critical patent/CH285020A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

  

      Verfahren    zur Herstellung eines     Pyrimidylaminochinolinderivates.       Gegenstand der vorliegenden Erfindung  ist ein Verfahren zur Herstellung von       4-Amino    - 6 - (2' -     amino    -     6'-methyl-pyrimidyl-4'-          amino)        -chinaldin-1,1.'-dimethobromid.     



  ES wurde     gefunden,    dass     dieses        4-Amino-          6-        (2'-ami        no-6'-metliyl-py        rimidyl-4'-amino)        -clii-          naldin-1.,1'-dimethobromid    wertvolle     trypano-          zide    Eigenschaften aufweist,

   insofern als bei  dessen subkutaner Verabreichung an mit     Try-          panosoma        congolense    infizierte Mäuse eine       100%ige        Heilung        der        Mäuse        von        der        Try-          panosomiasis    erzielt wird, ohne dass dabei ein  ernsthafter lokaler oder allgemeiner, soforti  ger oder verzögerter toxischer -Effekt. in     Er-          seheinimg    tritt.  



  Das erfindungsgemässe Verfahren zur Her  stellung von 4-Amino-6-(2'-amino-6'-methyl       pyrimidyl-4'-amino)-cliinaldin-1,1'-diniet.hobxo-          mid    ist dadurch gekennzeichnet, dass man       4-Ainino    - 6 -     (2'-        aniirio    -     6'-in.ethyl-pyrimidyl-4'-          amino)-eiiinaldin        finit        Methylbromid    zur Re  aktiori bringt.  



  Die Reaktion kann durch Erhitzen     der     vereinigten Reaktionskomponenten,     zweek-          mässigerweise    in einem Lösungsmittel, wie  z. B.     Athylalkohol,        Acetonitril    oder     Nitroben-          zol,        ausgeführt    werden.  



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



       Beispiel:     5,6 Teile     4-Amino-6-        (2'-amino-6'-methyl-          pyriinidyl-4'-aniino)-chinaldin,    5,7 Teile     l@le-          thylbromid    und 25 Teile Methylalkohol wer  den zusammen in einem     geschlossenen    Reak-         tionsgefäss    während acht     Stunden    bei 125 bis  130 C erhitzt. Nach Abkühlung wird das  Reaktionsgemisch filtriert und der feste  Rückstand in 500 Teilen Wasser gelöst.

   Man  stellt. die Lösung durch Zugabe von     Natrium-          earbonatlösung    gegen     Brilliantgelb    gerade al  kalisch und versetzt mit 20 Teilen N     atrium-          bromid.    Das ausgefällte feste Produkt wird  isoliert und aus 400 Teilen Wasser umkristal  lisiert, wobei     4-Amino-6-(2'-amino-6'-methyl-          pyriniiclyl-4'-ainino        )-eiiinaldin-1,l.'-dimethobro-          mid    in Form blass cremefarbener Nadeln vom       Sinp.        :316"    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'-amino-6'-methyl-pyrimidyl-4'-amino) -quinaldine-1,1'-dimethobromide.



  It has been found that this 4-amino-6- (2'-amino-6'-methyl-pyrimidyl-4'-amino) -clii- naldin-1,1'-dimethobromide has valuable trypanocidal properties ,

   insofar as when it is administered subcutaneously to mice infected with Trypanosoma congolense, a 100% cure of the mice from the Trypanosomiasis is achieved without a serious local or general, immediate or delayed toxic effect. comes into view.



  The process according to the invention for the preparation of 4-amino-6- (2'-amino-6'-methyl-pyrimidyl-4'-amino) -cliinaldine-1,1'-diniet.hobxomide is characterized in that 4 -Ainino-6 - (2'-aniirio-6'-yn.ethyl-pyrimidyl-4'-amino) -eiiinaldin finitely methyl bromide reactivates.



  The reaction can be carried out by heating the combined reaction components in a two-way manner in a solvent, such as. B. ethyl alcohol, acetonitrile or nitrobenzene are carried out.



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



       Example: 5.6 parts of 4-amino-6- (2'-amino-6'-methyl-pyriinidyl-4'-aniino) -quinaldine, 5.7 parts of ethyl bromide and 25 parts of methyl alcohol are used together in heated in a closed reaction vessel at 125 to 130 C for eight hours. After cooling, the reaction mixture is filtered and the solid residue is dissolved in 500 parts of water.

   One poses. the solution is just alkaline by adding sodium carbonate solution to brilliant yellow and mixed with 20 parts of atrium bromide. The precipitated solid product is isolated and recrystallized from 400 parts of water, 4-amino-6- (2'-amino-6'-methyl-pyriniiclyl-4'-ainino) -eiiinaldin-1, l .'- dimethobro- mid in the form of pale cream-colored needles from Sinp. : 316 "C (decomposition) is obtained.

Claims (1)

PATENTANSPRI?CH Verfahren zur Herstellung von 4 -Amino- 6- (2'-amino-6'-meth@#1-pyrimidyl-4'-amino) -chi- naldin-1,1'-dimetliobromid, dadurch gekenn zeichnet, dass man 4-Amino-6-(2'-amino-6'-me- thyl-pyrimidyl-4'-amino)-chinaldin mit. hle- thylbromid zur Reaktion bringt. PATENT APPLICATION Process for the preparation of 4-amino-6- (2'-amino-6'-meth @ # 1-pyrimidyl-4'-amino) -quinaldine-1,1'-dimetliobromide, characterized in that that 4-amino-6- (2'-amino-6'-methyl-pyrimidyl-4'-amino) -quinaldine with. brings halethyl bromide to the reaction. 4 - Amino - 6- (2'-ani ino-6'-nietliyl-pyr imidy 1- 4'-aniino)-chinaldin-1,1.'-diniethobromid ist ein blass cremefarbenes, kristallisiertes, festes Pro dukt vom Smp. 31.6" C (Zersetzung) 4 - Amino - 6- (2'-ani ino-6'-nietliyl-pyr imidy 1- 4'-aniino) -quinaldine-1,1 .'- diniethobromide is a pale cream-colored, crystallized, solid product of melting point. 31.6 "C (decomposition) . Es be sitzt wertvolle trypanozide Eigenschaften und bewirkt bei subkutaner Verabreichung an mit Try panosoma congolense infizierte Mäuse eine 100%ige Heilung der Mäuse von der Try- panosomiasis, wobei kein ernstlicher lokaler oder allgemeiner, sofortiger oder verzögerter toxischer Effekt in Erscheinung tritt. . . It has valuable trypanocidal properties and, when administered subcutaneously to mice infected with Trypanosoma congolense, causes 100% cure of the mice from Trypanosomiasis, with no serious local or general, immediate or delayed toxic effect. .
CH285020D 1947-08-22 1948-08-21 Process for the preparation of a pyrimidylaminoquinoline derivative. CH285020A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB285020X 1947-08-22
GB285026X 1947-08-22

Publications (1)

Publication Number Publication Date
CH285020A true CH285020A (en) 1952-08-15

Family

ID=32964136

Family Applications (1)

Application Number Title Priority Date Filing Date
CH285020D CH285020A (en) 1947-08-22 1948-08-21 Process for the preparation of a pyrimidylaminoquinoline derivative.

Country Status (1)

Country Link
CH (1) CH285020A (en)

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