DE338486C - Process for the preparation of a cholic acid compound - Google Patents

Process for the preparation of a cholic acid compound

Info

Publication number
DE338486C
DE338486C DE1914338486D DE338486DD DE338486C DE 338486 C DE338486 C DE 338486C DE 1914338486 D DE1914338486 D DE 1914338486D DE 338486D D DE338486D D DE 338486DD DE 338486 C DE338486 C DE 338486C
Authority
DE
Germany
Prior art keywords
cholic acid
preparation
acid compound
acid
formaldehyde
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DE1914338486D
Other languages
German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
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 Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Application granted granted Critical
Publication of DE338486C publication Critical patent/DE338486C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G8/00Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/18Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Darstellung einer Cholsäureverbindung. Eine Reihe von Erkrankun#gen der Gallen-Wege hat bekanntlich seine Ursache darin, daß sich in der Gallenblase zahlreiche pathogene Bakterien ansiedeln, die allen Desinfektionsversuchen widerstehen, weil es nicht gelingt, die desinfizierenden Substanzen bis an den Herd der Entzündung zu bringen.Process for the preparation of a cholic acid compound. A row of As is well known, diseases of the biliary tract are caused by the fact that the Gallbladder colonize numerous pathogenic bacteria, which all attempts to disinfect resist because it fails to get the disinfecting substances up to the stove to bring about inflammation.

Es wurde nun die bemerkenswerte Beobachtung gemacht, daß Cholsättre beim Erhitzen mit Formaldehyd eine neue Verbindung liefert, die den Formaldehyd relativ fest gebunden enthält. Das Produkt eignet sich im besonderen Maße für die Behandlung der Galle. Wahrscheinlich ist seine überraschende Wirkung nicht auf eine Desinfektion der ballenwege durch Formaldehydabspaltung zurückzuführen, sondern auf eine anregende Wirkung auf die Gallenabsonderung, wodurch gewissermaßen eine Ausspülung und Reinigung der Gallen-,vege stattfindet, die in ihrer Wirkung einer Desinfektion gleichkommt. Von den bisher gebräuchlichen Präparaten, wie z. B. den gallussauren Salzen, unterscheidet. sich das neue Präparat durch Geschmacklosigkeit und bessere Verträglichkeit. Beispiel i. looGewichtsfeile reine Cholsäure werden mit 50 Gewichtsteilen Paraformaldehyd innig verrieben und in einem offenen Gefäß 2 Stunden auf 17o bis igoo erhitzt, man läßt erkalten und löst die Reaktionsmasse in Alkohol, filtriert und läßt die Lösung in 2ooo Gewichtsteilen Eiswasser einlaufen, hierbei fällt die neue Verbindung als feines, weißes Pulver aus. Nach dem Auswaschen und Trocknen bildet sich ein weißes Pulver, das gegen 140 0 schmilzt und sich leicht in Alkohol und Eisessig löst, schwer dagegen in gebräuchlichen Koh#lenwasserstoffen. Löst man die Säure in verdünntem Ainmoniak und gibt Chlorbarium hinzu, so fällt das Bariumsalz als weißer Niederschlag aus, der abfiltriert und getrocknet wird. Aus ihm läßt sich mittels Salzsäure die Säure in reiner Form abscheiden. Beispiel 2.The remarkable observation has now been made that cholic saturation, when heated with formaldehyde, produces a new compound which contains the formaldehyde in relatively tightly bound form. The product is particularly suitable for the treatment of bile. Its surprising effect is probably not due to a disinfection of the ball passages by splitting off formaldehyde, but to a stimulating effect on the bile secretion, which in a sense rinses and cleans the bile, which is equivalent to disinfection in its effect. Of the previously used preparations such. B. the gallic acid salts. the new preparation is tasteless and better tolerated. Example i. 100 parts by weight of pure cholic acid are thoroughly triturated with 50 parts by weight of paraformaldehyde and heated in an open vessel to 17o to 10000 for 2 hours, allowed to cool and the reaction mass is dissolved in alcohol, filtered and the solution is poured into 2ooo parts by weight of ice water, the new compound falls as fine, white powder. After washing and drying, a white powder that melts at 140 0 and is readily soluble in alcohol and glacial acetic acid, hard contrast bons in common Koh # forms. If the acid is dissolved in dilute ammonia and chlorine barium is added, the barium salt separates out as a white precipitate, which is filtered off and dried. The acid can be separated from it in pure form using hydrochloric acid. Example 2.

ioo Gewichtsteile Cholsäure werden mit 5oo Gewichtsteilen Formaldehydlösung von 4o Prozent unter Druck 5 Stunden auf 170' erhitzt, man dekantiert das ölige Reaktionsprodukt mehrmals mit Wasser, nimmt in Alk-)hol auf und arbeitet die alkoholische Lösung wie im Beispiel i auf. Das so gewonnene Produkt zeigt die in Beispiel i angegebenen Eigenschaften. 100 parts by weight of cholic acid are heated to 170 ° for 5 hours with 500 parts by weight of formaldehyde solution of 40 percent under pressure, the oily reaction product is decanted several times with water, taken up in alcohol and the alcoholic solution is worked up as in Example i. The product obtained in this way shows the properties given in Example i.

Das Verfahren ist nicht an die in, den Beispielen angegebenen Mengenverhältnisse und Temperaturen gebunden.The process does not follow the proportions given in the examples and temperatures bound.

Claims (1)

PA TrXT- AN spizu c ii: Verfahren zur Darstellung einer Cholsäureverbindung, dadurch gekennzeichnet, daß man Cholsäure mit Formaldehyd oder seinen Polymeren in Reaktion bringt.PA TrXT- AN spizu c ii: Process for the preparation of a cholic acid compound, characterized in that one cholic acid with formaldehyde or its polymers brings in reaction.
DE1914338486D 1914-06-16 1914-06-16 Process for the preparation of a cholic acid compound Expired DE338486C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE338486T 1914-06-16

Publications (1)

Publication Number Publication Date
DE338486C true DE338486C (en) 1921-06-20

Family

ID=6222610

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1914338486D Expired DE338486C (en) 1914-06-16 1914-06-16 Process for the preparation of a cholic acid compound

Country Status (1)

Country Link
DE (1) DE338486C (en)

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