CH99202A - 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
- CH99202A CH99202A CH99202DA CH99202A CH 99202 A CH99202 A CH 99202A CH 99202D A CH99202D A CH 99202DA CH 99202 A CH99202 A CH 99202A
- 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 9
- -1 acridinium compound Chemical class 0.000 title claims description 4
- 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 5
- 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
- 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
- 150000001875 compounds Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ADAOOVVYDLASGJ-UHFFFAOYSA-N 2,7,10-trimethylacridin-10-ium-3,6-diamine;chloride Chemical compound [Cl-].CC1=C(N)C=C2[N+](C)=C(C=C(C(C)=C3)N)C3=CC2=C1 ADAOOVVYDLASGJ-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 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 Akridiniumverbindung. Die bisher bekannten Salze von Akri- diniumverbindungen haben den Nachteil, in Ölen und Fetten unlöslich zu sein, wodurch ihre Verwendung 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 Um setzung mit 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 70 bis<B>80'</B> warme Lö sung lässt man unter Rühren einlaufen eine Lösung von 4 kg 2.7-Dimethyl-3.6-diamino- 10-methylakridiniumchlorid in 100 Liter Wasser. Der orangefarbene Niederschlag wird nach zvd'eistündigem Rühren abgesaugt, ge waschen und getrocknet.
Der neue Körper ist ein orangefarbenes Pulver, das in Wasser unlöslich ist, sich aber in Ölen, Fetten, Alkohol, Benzol und Chloro form löst.
Die angegebene Temperatur und die Mengenverhältnisse können innerhalb weiter Grenzen geändert werden.
Process for the preparation of an oil- and fat-soluble salt of an acridinium compound. The previously known salts of acridine compounds have the disadvantage of being insoluble in oils and fats, which makes their use for some purposes in dermatology difficult. 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 by reaction with salts of high molecular weight paraffin carboxylic acids and olefin carboxylic acids give the corresponding acridinium salts, and that the latter are insoluble in water, as they are soluble in oils and fats and the disadvantages mentioned above mineral acid salts do not exhibit.
<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 4 kg of 2,7-dimethyl-3,6-diamino-10-methylacridinium chloride in 100 liters of water is allowed to run into the 70 to 80 ° warm solution with stirring. The orange-colored precipitate is filtered off with suction after stirring for about an hour, washed and dried.
The new body is an orange powder that is insoluble in water but dissolves in oils, fats, alcohol, benzene and 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 |
|---|---|---|---|
| CH99202T | 1921-09-17 | ||
| CH98437T | 1921-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH99202A true CH99202A (en) | 1923-05-16 |
Family
ID=25705403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH99202D CH99202A (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) | CH99202A (en) |
-
1921
- 1921-09-17 CH CH99202D patent/CH99202A/en unknown
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