DE606941C - Process for the preparation of solutions of acridine salts - Google Patents

Process for the preparation of solutions of acridine salts

Info

Publication number
DE606941C
DE606941C DEI44454D DEI0044454D DE606941C DE 606941 C DE606941 C DE 606941C DE I44454 D DEI44454 D DE I44454D DE I0044454 D DEI0044454 D DE I0044454D DE 606941 C DE606941 C DE 606941C
Authority
DE
Germany
Prior art keywords
solution
salts
solutions
preparation
acridine
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
DEI44454D
Other languages
German (de)
Inventor
Dr Louis Benda
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI44454D priority Critical patent/DE606941C/en
Application granted granted Critical
Publication of DE606941C publication Critical patent/DE606941C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/08Nitrogen atoms
    • C07D219/10Nitrogen atoms attached in position 9
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/08Nitrogen atoms

Description

Verfahren zur Herstellung von Lösungen von Acridinsalzen Es wurde gefunden, daß man in Wasser schwer lösliche Verbindungen von Diaminoacridinbasen mit Arsinsäuren der Benzolreihe leicht in Lösung bringen kann, wenn man diese Verbindungen in Gegenwart leicht löslicher Salze von Aminoacridinbasen in Wasser auflöst. Man kann auf diese Weise die gewünschten Konzentrationen, wie sie für Injektionen und zur Lokalbehandlung gewisser Infektionen notwendig sind, leicht herstellen. Diese Lösungen gewähren daneben den weiteren Vorteil, daß die Diaminoacridine selbst, wie bekannt, stark baktericid wirken, ihre therapeutische Wirkung sich somit mit derjenigen der von ihnen in Lösung gehalten,en, obenerwähnten Salze vereinigt. Anstatt die betreffenden Salze von Arsinsäuren mit Acridinbasen abzutrennen und sie dann in den erwähnten Lösungen aufzulösen, kann man auch die Darstellung der arsinsauren Salze und die Herstellung der Lösung in einem Arbeitsgang vereinigen.Process for the preparation of solutions of acridine salts It has been found that there are compounds of diaminoacridine bases which are sparingly soluble in water with arsinic acids of the benzene series can easily be brought into solution if these compounds dissolves in the presence of readily soluble salts of aminoacridine bases in water. Man can in this way the desired concentrations as required for injections and are necessary for the local treatment of certain infections. These Solutions also provide the further advantage that the diaminoacridines themselves, as is known, have a strong bactericidal effect, thus their therapeutic effect is also associated of those of the salts mentioned above, kept in solution by them. Instead of to separate the relevant salts of arsinic acids with acridine bases and then them To dissolve in the solutions mentioned, one can also use the representation of the arsinic acid Combine salts and the preparation of the solution in one operation.

Die als Ausgangsstoffe verwendeten Verbindungen von Diaminoacridinen mit Arsinsäuren der Benzolreihe können beispielsweise nach dem durch das Patent 6o6 498 geschützten Verfahren hergestellt werden. An leicht löslichen Salzen von Acridinbasen kommen beispielsweise die Hydrochloride, Lactate, Acetate und Nitrate in Frage. Beispiele i. Die durch doppelte Umsetzung von salzsaurem 3, 6-Diaminoacridin mit dem Natriumsalz der p-Glykolylaminophenylarsinsäure erhaltene Verbindung löst sich in Wasser im Verhältnis i : 6oo. Eine i,5°/oige Lösung von 3, 6-Diamino-io-methylacridiniumchlorid nimmt dagegen die sechsfache Menge auf.The compounds of diaminoacridines with arsinic acids of the benzene series used as starting materials can be prepared, for example, by the process protected by patent 6o6 498. Easily soluble salts of acridine bases include, for example, the hydrochlorides, lactates, acetates and nitrates. Examples i. The compound obtained by double decomposition of a hydrochloric acid 3, 6-diaminoacridine with the sodium salt of p-Glykolylaminophenylarsinsäure dissolves in water in the ratio i: 6oo. A 1.5% solution of 3,6-diamino-io-methylacridinium chloride, on the other hand, takes up six times the amount.

2. Von ioo ccm einer i °/oigen Lösung von 3, 6-Diamino-io-m-ethylacridiniumchlorid wird leicht i g der aus i Mol 2-Äthoxy-6, 9-dig aminoacridinlactat mit i Mol p-glykolylaminophenylarsinsaurem Natrium entstehenden Verbindung aufgenommen. Diese Verbindung löst sich in Wasser nur im Verhältnis i : 4o0.2. From 100 cc of an i% solution of 3,6-diamino-io-m-ethylacridinium chloride easily i g of 1 mole of 2-ethoxy-6, 9-dig aminoacridine lactate with 1 mole of p-glycolylaminophenylarsinsaurem Sodium resulting compound was added. This compound dissolves in water only in the ratio i: 4o0.

3. In ioo ccm i1/2°/oiger Lösung von 2-Äthoxy-6, 9-diaminoacridinlactat kann i g der Verbindung aus dem Mononatriumsalz der 3-Acetylamino-4-oxyphenyl-i-arsinsäure mit 3, 6-Diasnäno-io-methylacridiniumchlorid gelöst werden, während sich diese Verbindung in Wasser nur im Verhältnis i : 4oo löst.3. In 100 cc of 1/2% solution of 2-ethoxy-6,9-diaminoacridine lactate can i g of the compound from the monosodium salt of 3-acetylamino-4-oxyphenyl-i-arsinic acid with 3, 6-diasnano-io-methylacridinium chloride to be dissolved while this compound dissolves in water only in a ratio of i: 400.

q.. Aus i Mol 3, 6-Diamino-io-methylacridiniumchlorid und i Mol des Natriumsalzes der p-Glylcolylaminophenylarsinsäure erhält man eine Verbindung, die sich in 4oo Teilen Wasser löst. In 2 °/oiger Lösung von 2-Äthoxy-6, 9-diaminoacridinlactat sowie in i1/2°foigerLösung von3, 6-Di,amino-io-methylacridiniumclilorid löst sie sich dagegen bereits im Verhältnis i : Zoo.q .. From i moles of 3, 6-diamino-io-methylacridinium chloride and i moles of des Sodium salt of p-glycolylaminophenylarsinic acid gives a compound which dissolves in 400 parts of water. In a 2% solution of 2-ethoxy-6,9-diaminoacridine lactate as well as in 1/2 ° solution of 3,6-di, amino-io-methylacridinium chloride solves on the other hand, they are already in the ratio i: zoo.

5. In ioo ccm Wasser von 30° löst man 475 g 3, 6-Diamino-io-methylacridiniumchlorid und dann 0,5 g p-glykolylaminophenylarsinsaures Natrium. Trotz ihres Gehaltes an Natriumchlorid bleibt die Lösung klar.5. 475 g of 3,6-diamino-io-methylacridinium chloride and then 0.5 g of sodium p-glycolylaminophenylarsinate are dissolved in 100 cc of water at 30 °. Despite its sodium chloride content, the solution remains clear.

. 6. i5o Teile i'/2°joige Lösung von 3, 6-Diamino-io-methylacridiniumacetat lösen i Teil der Verbindung aus äquivalenten Mengen von 3, 6-Diamino-i o-methylacri,diniumchlori.dund p-glykolylaminophenylarsins-aurem Natrium.. 6. 150 parts of a 1/2 ° solution of 3,6-diamino-io-methylacridinium acetate solve i part of the compound from equivalent amounts of 3, 6-diamino-i o-methylacri, diniumchlori.dund sodium p-glycolylaminophenylarsinic acid.

Eine i %ige Lösung von 3, 6-Diaminoio-methylacridiniumnitrat sowie eine 1/2°/oige Lösung der Verbindung aus äquivalenten Mengen von 3, 6-Diamino- i o-methylacridiniumchlorid und p-glykolylaminophenylarsinsaurem Natrium sind jede für sich nicht haltbar, sondern kristallisieren beim Abkühlen.An i% solution of 3, 6-Diaminoio-methylacridinium nitrate as well a 1/2% solution of the compound from equivalent amounts of 3,6-diamino- i o-methylacridinium chloride and sodium p-glycolylaminophenylarsinate are each Not durable by itself, but crystallize when cooling.

Löst man aber in Zoo Teilen einer i °foigen Lösung von 3, 6-Diamino-io-methylacridiniumnitrat i Teil der Verbindung aus i 142o1 p-glykolylaminophenylarsinsaurem Natrium mit I M01 3, 6-Diamino-io-methyl.acrid.iniumchlorid, so ist die Lösung haltbar.If, however, parts of a solution of 3,6-diamino-io-methylacridinium nitrate are dissolved in zoo i part of the compound from i 142o1 sodium p-glycolylaminophenylarsinate with I. M01 3, 6-diamino-io-methyl.acrid.iniumchlorid, the solution is stable.

Claims (1)

PATENTANSPRUCIi: Verfahren zur Herstellung von Lösungen von Acridinsalzen, dadurch gekennzeichnet, daß man Salze von Arsinsäuren der Benzolreihe mit Diaminoacridinbasen in wässerigen Lösungen von leichtlöslichen Salzen gleicher oder anderer Acridinbasen auflöst.PATENT CLAIMS: Process for the preparation of solutions of acridine salts, characterized in that salts of arsinic acids of the benzene series with diaminoacridine bases in aqueous solutions of easily soluble salts of the same or different acridine bases dissolves.
DEI44454D 1932-05-15 1932-05-15 Process for the preparation of solutions of acridine salts Expired DE606941C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI44454D DE606941C (en) 1932-05-15 1932-05-15 Process for the preparation of solutions of acridine salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI44454D DE606941C (en) 1932-05-15 1932-05-15 Process for the preparation of solutions of acridine salts

Publications (1)

Publication Number Publication Date
DE606941C true DE606941C (en) 1934-12-14

Family

ID=7191290

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI44454D Expired DE606941C (en) 1932-05-15 1932-05-15 Process for the preparation of solutions of acridine salts

Country Status (1)

Country Link
DE (1) DE606941C (en)

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