CH243026A - Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether. - Google Patents

Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether.

Info

Publication number
CH243026A
CH243026A CH243026DA CH243026A CH 243026 A CH243026 A CH 243026A CH 243026D A CH243026D A CH 243026DA CH 243026 A CH243026 A CH 243026A
Authority
CH
Switzerland
Prior art keywords
amidino
diphenyl ether
soluble salt
preparation
soluble
Prior art date
Application number
Other languages
German (de)
Inventor
Limited May Baker
Original Assignee
May & Baker 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 May & Baker Ltd filed Critical May & Baker Ltd
Publication of CH243026A publication Critical patent/CH243026A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/263—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings the aromatic rings being non-condensed

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     löslichen    Salzes des     4,4'-Di-amidino-diphenyläthers.       Es hat sich gezeigt, dass der     4,4'-Di-ami-          dino-diphenyläther    von beträchtlichem thera  peutischem     Interesse    ist, doch sind seine  Salze, wie das     Dichlorhydrat,    gleich wie bei  andern aromatischen     Di-amidinen,    in Wasser  nicht sehr gut löslich. Es ist jedoch gerade  in der Therapie von Vorteil, beständige, in  Wasser leicht lösliche Salze zur Verfügung  zu haben, und die vorliegende Erfindung be  fasst sich mit der Herstellung eines solchen  Salzes.

   In vielen Fällen ergaben, wie fest  gestellt wurde, therapeutisch wertvolle ba  sische Verbindungen mit     Methansulfonaten     äusserst lösliche Salze; im Falle des     4,4'-Di-          amidino-diphenyläthers    ist jedoch das     Di-          methansulfonat    nur wenig mehr löslich als  das     Di-chlorhydrat.     



  Gemäss dem Verfahren des vorliegenden  Patentes wird ein leicht lösliches Salz des       4,4'-Di-amidino-diphenyläthers,    das als     Di-          isäthionat    bezeichnet werden kann, dadurch  hergestellt, dass man     4,4'-Di-amidino-diphe-          nyläther    mit     ss-Oxyäthansulfonsäure    umsetzt.

    <I>Beispiel:</I>  67,2 g 4,4'     Di-amidino-diphenyläther    wur  den in einem geringen     tiberschuss    einer     wäss-.            rigen    8     N-Lösung    der     ss-Oxyäthansulfosäure     eingetragen und gerade genügend Wasser zu  gefügt, um vollständige Lösung in der Kälte  zu     bewirken.    Die Lösung war gerade lack  mussauer.

   Dann wurde etwa     1/.4    ihres Vo  lumens Alkohol und hierauf langsam und  unter Rühren Aceton zugegeben, so dass das       4,4'-Di-amidino-diphenyläther-di-ss-oxyäthan-          sulfonat        (Di-isäthionat)    kristallin ausgeschie  den     wurde.    Der     Acetonzusatz    wurde so lange  fortgesetzt, bis die Ausscheidung nahezu be  endet war. Dann wurde eine Zeitlang stehen  gelassen, die Kristalle     abfiltriert    und mit  Aceton gewaschen und getrocknet. Die Aus  beute betrug 130 g. Die Löslichkeit in Was  ser war etwa 1 in 1 bei 20  C.



  Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether. It has been shown that the 4,4'-di-amidino-diphenyl ether is of considerable therapeutic interest, but its salts, like the dichlorohydrate, like other aromatic di-amidines, are not very soluble in water . However, it is particularly advantageous in therapy to have stable salts readily available which are readily soluble in water, and the present invention is concerned with the production of such a salt.

   In many cases, as has been established, therapeutically valuable basic compounds with methanesulfonates resulted in extremely soluble salts; in the case of 4,4'-di-amidino-diphenyl ether, however, the dimethanesulfonate is only slightly more soluble than the di-chlorohydrate.



  According to the process of the present patent, a readily soluble salt of 4,4'-di-amidino-diphenyl ether, which can be referred to as di-isethionate, is prepared by adding 4,4'-di-amidino-diphenyl ether ss-Oxyäthansulfonsäure converts.

    <I> Example: </I> 67.2 g of 4,4'-di-amidino-diphenyl ether were used in a slight excess of an aqueous. Entered 8 N solution of ß-oxyethanesulfonic acid and added just enough water to bring about complete dissolution in the cold. Lack mussauer was the solution.

   Then about 1 / .4 of their volume alcohol and then slowly and with stirring acetone was added so that the 4,4'-di-amidino-diphenyl ether-di-ss-oxyethane sulfonate (di-isethionate) was precipitated in crystalline form . The addition of acetone was continued until the excretion almost ended. It was then left to stand for a while, and the crystals were filtered off, washed with acetone and dried. The yield was 130 g. The solubility in water was about 1 in 1 at 20 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines leicht löslichen Salzes des 4,4'-Di-amidino-diphenyl- äthers, dadurch gekennzeichnet, dass man 4,4'- Di - amidino - diphenyläther mit ss - Oxy- äthansulfonsäure umsetzt. Die neue Verbindung bildet Kristalle, die in Wasser bei 20 C etwa 1 in 1 löslich sind. PATENT CLAIM: Process for the production of a readily soluble salt of 4,4'-di-amidino-diphenyl ether, characterized in that 4,4'-di-amidino-diphenyl ether is reacted with β-oxyethanesulphonic acid. The new compound forms crystals that are approximately 1 in 1 soluble in water at 20 C.
CH243026D 1945-03-15 1945-07-23 Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether. CH243026A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH236875T 1945-03-15
CH243026T 1945-07-23

Publications (1)

Publication Number Publication Date
CH243026A true CH243026A (en) 1946-06-15

Family

ID=25728192

Family Applications (1)

Application Number Title Priority Date Filing Date
CH243026D CH243026A (en) 1945-03-15 1945-07-23 Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether.

Country Status (1)

Country Link
CH (1) CH243026A (en)

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