CH97978A - Process for the preparation of diallyl xanthine. - Google Patents

Process for the preparation of diallyl xanthine.

Info

Publication number
CH97978A
CH97978A CH97978DA CH97978A CH 97978 A CH97978 A CH 97978A CH 97978D A CH97978D A CH 97978DA CH 97978 A CH97978 A CH 97978A
Authority
CH
Switzerland
Prior art keywords
diallyl
preparation
xanthine
diamino
alcohol
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH97978A publication Critical patent/CH97978A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3

Landscapes

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

Description

  

  Verfahren zur Darstellung von     Diallylganthin.       Es wurde gefunden, dass man zu dem bis  her unbekannten     Diallylxanthin    gelangen  kann, indem man die     Formylverbindung    des  1 .     3-Diallyl-4    .     5-diamino-2    .     6-dioxypyrimi-          dins    mit Alkalien, beispielsweise mit Natron  lauge, behandelt.  



  Die als     Ausgaugsstoff    dienende     Formyl-          verbindung    des     1.3-Diallyl-4.5-diamino-          2.6-dioxypyriinidins    kann in folgender  Weise erhalten werden: Man kondensiert       Diallylh.arnstoff    mit     Cyanessigsäure    oder       Cyanessigester    und     führt,das    Kondensations  produkt mit salpetriger Säure in     Diallyl-iso-          nitrosoaininodioxypyrimidin    über.

   Letzteres  wird zu     Diallyl-diamino-dioxypyrimidin    re  duziert und dieses durch Erhitzen mit Amei  sensäure     forinyliert.    Statt mit     Cyanessigsäure     k     -ann    man den     Diallylharnstoff    auch mit     Iso-          nitroso:cyanessigester    kondensieren, in wel  chem Falle man direkt zum     Isonitrosokörper     gelangt.  



  Die neue Verbindung soll zu therapeu  tischen     Zwecken    verwendet werden.  <I>Beispiel:</I>  1     Mol.    Formyl-1.3=diallyl-4.5-clia.mino-    2 . 6 .     ,clioxy-pyrimidin    wird mit 1     Mol.        n-Na-          tronlauge    während     1/4    Stunde auf dem Was  serbad erhitzt. Hierauf säuert man in der  Wärme mit Essigsäure an und lässt erkalten,  worauf das 1 . 3 .     Diallylxanthin    auskristalli  siert. Dasselbe bildet bei 155 bis 156   schmel  zende, in kaltem Wasser und kaltem Alkohol  sehr schwer, in warmem Wasser und war  mem Alkohol, ferner in Äther und Benzol  lösliche Kristalle.

           PATENTANSPRUCH:     Verfahren zur Darstellung von     Diallyl-          xanthin,    dadurch gekennzeichnet, dass man  die     Formylverbindung    des 1     .3-Diallyl-4.        5-          diamino-2.6-dioxypyrimidins    mit Alkalien  behandelt.  



  Das     Triallylxanthin    bildet bei 155 bis  <B>156'</B> schmelzende, in kaltem Wasser und  kaltem Alkohol sehr schwer, in warmem  Wasser und warmem Alkohol, ferner in  Äther     und    Benzol lösliche Kristalle.



  Process for the preparation of diallylganthin. It has been found that the hitherto unknown diallylxanthine can be obtained by using the formyl compound of 1. 3-diallyl-4. 5-diamino-2. 6-dioxypyrimidines with alkalis, for example with caustic soda, treated.



  The formyl compound of 1,3-diallyl-4,5-diamino-2,6-dioxypyriinidine which serves as the exhaust substance can be obtained in the following manner: Diallyl urea is condensed with cyanoacetic acid or cyanoacetate and the condensation product with nitrous acid is converted into diallyl isonitrosoaininodioxypyrimidine above.

   The latter is reduced to diallyl-diamino-dioxypyrimidine and this is forinylated by heating with formic acid. Instead of using cyanoacetic acid, the diallylurea can also be condensed with isonitroso: cyanoacetic ester, in which case the isonitroso body is obtained directly.



  The new compound is intended to be used for therapeutic purposes. <I> Example: </I> 1 mol. Formyl-1.3 = diallyl-4.5-clia.mino- 2. 6th , Clioxy-pyrimidine is heated with 1 mol. N-sodium hydroxide solution for 1/4 hour on the water bath. Then acidify with acetic acid in the warmth and let it cool, whereupon the 1st 3. Diallylxanthine crystallized out. At 155 to 156 it forms melting crystals, which are very difficult in cold water and cold alcohol, in warm water and were in alcohol, and also crystals soluble in ether and benzene.

           PATENT CLAIM: Process for the preparation of diallyl xanthine, characterized in that the formyl compound of 1 .3-diallyl-4. 5- diamino-2,6-dioxypyrimidines treated with alkalis.



  The triallyl xanthine forms at 155 to <B> 156 '</B> melting crystals, which are very difficult to dissolve in cold water and cold alcohol, and crystals which are soluble in warm water and warm alcohol, and also in ether and benzene.
CH97978D 1921-10-07 1921-10-07 Process for the preparation of diallyl xanthine. CH97978A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH97978T 1921-10-07

Publications (1)

Publication Number Publication Date
CH97978A true CH97978A (en) 1923-02-16

Family

ID=4355743

Family Applications (1)

Application Number Title Priority Date Filing Date
CH97978D CH97978A (en) 1921-10-07 1921-10-07 Process for the preparation of diallyl xanthine.

Country Status (1)

Country Link
CH (1) CH97978A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2420346A1 (en) * 1977-04-02 1979-10-19 Hoechst Ag MEDICINAL PRODUCTS CONTAINING ALCENYLXANTHINS AND THEIR PREPARATION PROCESS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2420346A1 (en) * 1977-04-02 1979-10-19 Hoechst Ag MEDICINAL PRODUCTS CONTAINING ALCENYLXANTHINS AND THEIR PREPARATION PROCESS

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