CH139404A - Process for the preparation of 2-ethoxy-6,9-diaminoakridine cholate. - Google Patents
Process for the preparation of 2-ethoxy-6,9-diaminoakridine cholate.Info
- Publication number
- CH139404A CH139404A CH139404DA CH139404A CH 139404 A CH139404 A CH 139404A CH 139404D A CH139404D A CH 139404DA CH 139404 A CH139404 A CH 139404A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethoxy
- diaminoakridine
- cholate
- preparation
- water
- Prior art date
Links
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 title claims description 6
- 229940099352 cholate Drugs 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004380 Cholic acid Substances 0.000 claims description 3
- 229960002471 cholic acid Drugs 0.000 claims description 3
- 235000019416 cholic acid Nutrition 0.000 claims description 3
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 2
- VNDXKMITHCJCOL-UHFFFAOYSA-N acridine-1,2-diamine Chemical compound C1=CC=CC2=CC3=C(N)C(N)=CC=C3N=C21 VNDXKMITHCJCOL-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal 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
- C07J9/005—Normal 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 containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung von 2-Äthoxy-6,9-diaminoakridineholat. Es wurde gefunden, dass man zu einer wertvollen neuen Verbbindung gelangen kann, wenn mian 2-Äthoxy-6,9-,diaminoakridin und Cholsäure aufeinander einwirken lässt.
Die Salzbildung vollzieht sich leicht, wenn man die beiden Komponenten in einem Lösungsmittel vereinigt. Das Salz kann auch durch doppelten Umsatz von Salzen der Aus- gangsmaterialien ,gewonnen werden, wobei sich zunächst freie Ch@olsäure und das freie Akrzdiinderivat bilden, welche Verbindungen dann zu,demSalz zusammentreten.
Wie Versuche gezeigt haben, besitzt das neue Salz gegenüber Mikroorganismen stärker abtötende Eigenschaften als bekannte Salze des 2-tlthoxy-6,9-diaminoakridins; es soll da her therapeutische Verwendung finden.
Beispiel 5,9 gr 2-Äthoxy-6,9:diaminoakridinium- liydrochlorid werden in 400 cm' Wasserge- löst und mit einer Lösung von 9,5 gr Natriumcholat in 100 cm' Wasser ver einigt. Dass 2-Äthoxy-6,9-.diaminoakridincho- lat scheidet sich als gelbes, mikrokristallines Pulver ab. Es ist in Alkohol und Methyl alkohol löslich, in Äther und Wasser nahezu unlöslich.
Process for the preparation of 2-ethoxy-6,9-diaminoakridine holate. It has been found that a valuable new compound can be obtained if 2-ethoxy-6,9-, diaminoacridine and cholic acid are allowed to act on one another.
Salt formation takes place easily when the two components are combined in a solvent. The salt can also be obtained by double conversion of salts of the starting materials, in which case free cholic acid and the free acridine derivative are initially formed, which compounds then combine to form the salt.
As tests have shown, the new salt has stronger killing properties against microorganisms than known salts of 2-thoxy-6,9-diaminoacridine; it should therefore find therapeutic use.
Example 5.9 g of 2-ethoxy-6.9: diaminoakridinium liydrochlorid are dissolved in 400 cm 'of water and combined with a solution of 9.5 g of sodium cholate in 100 cm' of water. The 2-ethoxy-6,9-diaminoakridine cholate separates out as a yellow, microcrystalline powder. It is soluble in alcohol and methyl alcohol, and almost insoluble in ether and water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH126678T | 1928-10-22 | ||
| CH139404T | 1928-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139404A true CH139404A (en) | 1930-04-15 |
Family
ID=25710715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139404D CH139404A (en) | 1928-10-22 | 1928-10-22 | Process for the preparation of 2-ethoxy-6,9-diaminoakridine cholate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139404A (en) |
-
1928
- 1928-10-22 CH CH139404D patent/CH139404A/en unknown
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