CH99204A - Process for the preparation of an oil- and fat-soluble salt of an acridinium compound. - Google Patents
Process for the preparation of an oil- and fat-soluble salt of an acridinium compound.Info
- Publication number
- CH99204A CH99204A CH99204DA CH99204A CH 99204 A CH99204 A CH 99204A CH 99204D A CH99204D A CH 99204DA CH 99204 A CH99204 A CH 99204A
- Authority
- CH
- Switzerland
- Prior art keywords
- fat
- oil
- preparation
- soluble salt
- acridinium compound
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 10
- -1 acridinium compound Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic 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
- C07D219/08—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines öl- und fettlöslichen Salzes einer Alzridiniumverbindung. Die bisher bekannten Salze von Akri- diniumverbindungen haben den Nachteil, in Ölen und Fetten unlöslich zu sein, wodurch ihre Versendung für manche Zwecke der Dermatologie erschwert wird. Auch die sub kutane und intraperitoneale Anwendung ist wegen der Reizwirkung wässeriger Lösungen der bekannten Akridiniumsalze nicht emp fehlenswert.
Es wurde nun gefunden, dass diese was serlöslichen, mineralsauren Salze durch Vm- setzung <B>mit</B> Salzen hochmolekularer Paraf- finkarbonsäuren und Olefinkarbonsäuren die entsprechenden Akridiniumsalze liefern, und dass diese letzteren in Wasser unlöslich, da gegen in Ölen und Fetten löslich sind und die oben erwähnten Nachteile der mineral sauren Salze nicht aufweisen.
<I>Beispiel:</I> 4 kg Palmitinsäure werden unter Zusatz der nötigen Menge Natronlauge in 800 Liter Wasser gelöst. In die etwa<B>80'</B> warme Lö sung lä,sst man unter ständigem Rühren ein laufen eine Lösung von 8 kg B . 6-Di/di- methylamino/-10-methyl-akridiniumnitrat in 500 Liter Wasser. Nachdem man unter Rüh ren hat abkühlen lassen, saugt man den Nie derschlag ab, wäscht nach und trocknet auf dem Wasserbad.
Das Salz ist ein braunrotes Pulver, un löslich in Wasser, ,dagegen löslich in Ölen, Fetten, Alkohol, Benzol, Chloroform.
Die angegebene Temperatur und die Mengenverhältnisse können innerhalb weiter Grenzen abgeändert werden.
Process for the preparation of an oil- and fat-soluble salt of an alzridinium compound. The previously known salts of acridinium compounds have the disadvantage that they are insoluble in oils and fats, which makes it difficult to send them for some dermatological purposes. Subcutaneous and intraperitoneal use is also not recommended because of the irritating effect of aqueous solutions of the known acridinium salts.
It has now been found that these water-soluble, mineral acid salts produce the corresponding acridinium salts by reaction with salts of high molecular weight paraffin carboxylic acids and olefin carboxylic acids, and that the latter are insoluble in water, as opposed to oils and fats are soluble and do not have the disadvantages of mineral acid salts mentioned above.
<I> Example: </I> 4 kg of palmitic acid are dissolved in 800 liters of water with the addition of the necessary amount of sodium hydroxide solution. A solution of 8 kg B is poured into the approximately <B> 80 '</B> warm solution with constant stirring. 6-di / dimethylamino / -10-methyl-acridinium nitrate in 500 liters of water. After it has been allowed to cool while stirring, the precipitate is vacuumed off, washed and dried on the water bath.
The salt is a brown-red powder, insoluble in water, but soluble in oils, fats, alcohol, benzene, chloroform.
The specified temperature and the proportions can be changed within wide limits.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH99204T | 1921-09-17 | ||
| CH98437T | 1921-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH99204A true CH99204A (en) | 1923-05-16 |
Family
ID=25705405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH99204D CH99204A (en) | 1921-09-17 | 1921-09-17 | Process for the preparation of an oil- and fat-soluble salt of an acridinium compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH99204A (en) |
-
1921
- 1921-09-17 CH CH99204D patent/CH99204A/en unknown
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