CH280072A - Process for the preparation of a substance which lowers the level of prothrombin in the blood. - Google Patents

Process for the preparation of a substance which lowers the level of prothrombin in the blood.

Info

Publication number
CH280072A
CH280072A CH280072DA CH280072A CH 280072 A CH280072 A CH 280072A CH 280072D A CH280072D A CH 280072DA CH 280072 A CH280072 A CH 280072A
Authority
CH
Switzerland
Prior art keywords
lowers
blood
substance
prothrombin
level
Prior art date
Application number
Other languages
German (de)
Inventor
Podnik Spojene Farmace Narodni
Original Assignee
Spojene Farmaceuticke Z Narodn
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 Spojene Farmaceuticke Z Narodn filed Critical Spojene Farmaceuticke Z Narodn
Priority claimed from GB3687646A external-priority patent/GB632805A/en
Publication of CH280072A publication Critical patent/CH280072A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
    • C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
    • C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
    • C07D311/48—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring with two such benzopyran radicals linked together by a carbon chain

Landscapes

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

Description

  

  Verfahren zur Herstellung einer das     Prothrombinniveau    im Blut herabsetzenden  Substanz.    Versuche haben gezeigt, dass der primäre       Isobutylester    der     Bis-(4-oxy-eumarinyl)-essig-          säure    therapeutisch ebenso wertvoll ist wie  der     Äthvlester.     



       (legenstand    des Patentes ist ein Verfah  ren zur     -Ierstellung    einer das     Prothrombin-          niveau    im Blut herabsetzenden Substanz, wel  ches dadurch gekennzeichnet ist, dass eine  Verbindung der Formel  
EMI0001.0010     
    mit einer Verbindung der Formel  
EMI0001.0011     
    wobei     Y        und    i' reaktionsfähige, bei der Reak  tion mit Ausnahme eines in einem von ihnen  enthaltenen Sauerstoffatoms sich abspaltende  Reste bedeuten, umgesetzt wird.

   Der so erhal  tene     Bis-(4-oxy-eumarinyl)-essigsättre-prim.-          isobutylester    bildet farblose, in Wasser unlös  liche Kristalle vom     Schmp.    1.70 bis 1.71  C.  



  Die Einführung der     Isobutylgruppe    in die       Carboxylgruppe    ohne gleichzeitige     Veräthe-          rung    der     Hydroxylgruppen    in den     Oxy        cuma-          rinresten    erfolgt zweckmässig durch Behand  lung der     Carbonsäure    mit. primärem Isobutyl-         alkohol    in Gegenwart eines wasserentziehen  den Mittels, wie trockenem Chlorwasserstoff  oder konzentrierter Schwefelsäure.  



  <I>Beispiel:</I>  <B>100</B> g Bis-     (4-oxy        -cumarinyl)        -essigsäure     wurden mit 450     cma        6n-Salzsäure-Lösung    in  primären     Isobutylalkohol    vermischt und die  Mischung unter ständigem Umrühren am       Rüekflusskühler    während 50 Stunden auf  75  C erhitzt. Nach dem Erkalten des Reak  tionsgutes wurde der auskristallisierte Ester       abfiltriert    und wiederholt mit warmem Me  thanol ausgewaschen. Ausbeute an Bis     -          oxyeumarinyl.)        -essigsäure-isobutylester    89 g.

    Schmelzpunkt<B>170</B> bis     177.     C.



  Process for the preparation of a substance which lowers the level of prothrombin in the blood. Experiments have shown that the primary isobutyl ester of bis (4-oxy-eumarinyl) acetic acid is just as therapeutically valuable as the ethereal ester.



       (The status of the patent is a process for the production of a substance which lowers the prothrombin level in the blood, which is characterized in that a compound of the formula
EMI0001.0010
    with a compound of the formula
EMI0001.0011
    where Y and i 'mean reactive radicals which split off in the reaction with the exception of an oxygen atom contained in one of them, is implemented.

   The bis- (4-oxy-eumarinyl) -acetic saturate primary isobutyl ester obtained in this way forms colorless, water-insoluble crystals with a melting point of 1.70 to 1.71 C.



  The introduction of the isobutyl group into the carboxyl group without simultaneous etherification of the hydroxyl groups in the oxycarine residues is expediently effected by treating the carboxylic acid with. primary isobutyl alcohol in the presence of a dehydrating agent such as dry hydrogen chloride or concentrated sulfuric acid.



  <I> Example: </I> <B> 100 </B> g of bis- (4-oxy-coumarinyl) -acetic acid were mixed with 450 cma 6N hydrochloric acid solution in primary isobutyl alcohol and the mixture was stirred continuously on the reflux condenser heated to 75 ° C. for 50 hours. After the reaction material had cooled down, the ester which had crystallized out was filtered off and washed repeatedly with warm methanol. Yield of bis-oxyeumarinyl.) -Acetic acid isobutyl ester 89 g.

    Melting point 170 to 177. C.

Claims (1)

PATEN TANSPRL?CH Verfahren zur Herstellung einer das Pro- thrombinniv eau im Blut herabsetzenden Sub stanz, dadurch gekennzeichnet, dass eine Ver bindung der Formel EMI0001.0043 mit einer Verbindung der Formel EMI0001.0044 wobei X und Y reaktionsfähige, bei der Reak tion mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sich abspaltende Reste bedeuten, umgesetzt wird. Der so erhal tene Bis-(4-oxy-ciimarinyl)-essigsäure-prim.- isobutylester bildet farblose, in Wasser unlös liche Kristalle vom Sehmp. 170 bis 7.71. C. PATEN TANSPRL? CH Process for the production of a substance which lowers the prothrombin level in the blood, characterized in that a compound of the formula EMI0001.0043 with a compound of the formula EMI0001.0044 wherein X and Y are reactive radicals which are split off in the reaction with the exception of an oxygen atom contained in them, is implemented. The bis (4-oxy-ciimarinyl) acetic acid primary isobutyl ester obtained in this way forms colorless, water-insoluble crystals of Sehmp. 170 to 7.71. C.
CH280072D 1946-08-31 1946-11-06 Process for the preparation of a substance which lowers the level of prothrombin in the blood. CH280072A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CS2482512X 1946-08-31
CH280072T 1946-11-06
GB3687646A GB632805A (en) 1946-12-13 1946-12-13 Process for the production of compounds reducing the prothrombin level in the blood

Publications (1)

Publication Number Publication Date
CH280072A true CH280072A (en) 1951-12-31

Family

ID=32233753

Family Applications (1)

Application Number Title Priority Date Filing Date
CH280072D CH280072A (en) 1946-08-31 1946-11-06 Process for the preparation of a substance which lowers the level of prothrombin in the blood.

Country Status (1)

Country Link
CH (1) CH280072A (en)

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