CH146548A - Process for the preparation of benzimidazolone-5-stibic acid. - Google Patents
Process for the preparation of benzimidazolone-5-stibic acid.Info
- Publication number
- CH146548A CH146548A CH146548DA CH146548A CH 146548 A CH146548 A CH 146548A CH 146548D A CH146548D A CH 146548DA CH 146548 A CH146548 A CH 146548A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- stibic
- preparation
- benzimidazolone
- dihydride
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 244000008991 Curcuma longa Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von Benzimidazolon-6-stibinsäure. Es wurde gefunden, dass die bisher nicht bekannte Benzimidazolon-5-stibinsäure durch Umsetzung der Diazoverbindung des 5-Amino- 2-oxobenzimdazol-2.3-dihydrid mit anti- moniger Säure erhalten wird.
Sie zeigt hervorragende Wirkung gegen Protozoenerkrankungen. Zur therapeutischen Verwendung wird sie zweckmässig in ein lösliches Salz überführt.
<I>Beispiel:</I> 19 gr 5-Amino-2-oxo-benzimidazol-2. 3 - dihydrid-hydrochlorid (hergestellt z. B. nach Hager B. 17, S.2631) werden in 100 ums Wasser unter Zusatz von 16 cm' konzen trierter Salzsäure mit der berechneten Menge Natriumnitrit dianotiert.
Die Diazolösung wird in eine Antimonitlösung eingerührt, die zum Beispiel auf folgende Weise hergestellt werden kann: 16 gr Antimontrioxyd werden in 200 <B>cm'</B> Wasser, 50 cm3 Glycerin und 35' cm' Natronlauge (40 B6) unter Erwärmen gelöst. Zur Umsetzung wird die Lösung zweckmässig auf Zimmertemperatur abgekühlt.
Wenn die Stickstoffentwicklung beendet ist und die Lösung mit Resorcin nicht mehr kuppelt, wird sie zuerst mit Salzsäure und dann mit Kohlensäure soweit abgestumpft, dass sie auf Curcuma noch schwach alkalische Reaktion zeigt. Sie wird dann filtriert, mit Tierkohle geklärt und mit Salzsäure kongo sauer gemacht, wobei die 2-03obenzimidazol- 2.3-dihydrid-5-stibinsäure ausfällt. Sie ist ein weisses, in verdünnten Alkalien und organi schen Basen lösliches Pulver. Sie zeichnet sich durch hervorragende Wirkung gegen Protozoenerkrankungen aus.
Process for the preparation of benzimidazolone-6-stibic acid. It has been found that the previously unknown benzimidazolone-5-stibic acid is obtained by reacting the diazo compound of 5-amino-2-oxobenzimdazole-2,3-dihydride with antimony acid.
It shows excellent action against protozoal diseases. For therapeutic use, it is expediently converted into a soluble salt.
<I> Example: </I> 19 gr 5-amino-2-oxo-benzimidazole-2. 3 - dihydride hydrochloride (prepared for example according to Hager B. 17, p.2631) are dianotized with the calculated amount of sodium nitrite in 100 μm water with the addition of 16 cm 'concentrated hydrochloric acid.
The diazo solution is stirred into an antimonite solution, which can be prepared, for example, in the following way: 16 g of antimony trioxide are mixed with 200 cm of water, 50 cm3 of glycerine and 35 cm of sodium hydroxide solution (40 B6) while warming solved. For implementation, the solution is expediently cooled to room temperature.
When the development of nitrogen has ended and the solution no longer couples with resorcinol, it is first blunted with hydrochloric acid and then with carbonic acid to such an extent that it still shows a weakly alkaline reaction to turmeric. It is then filtered, clarified with animal charcoal and made Congo acidic with hydrochloric acid, whereby the 2-03obenzimidazole-2,3-dihydride-5-stibic acid precipitates. It is a white powder that is soluble in diluted alkalis and organic bases. It is characterized by its excellent action against protozoal diseases.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146548X | 1928-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146548A true CH146548A (en) | 1931-04-30 |
Family
ID=5671433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146548D CH146548A (en) | 1928-11-07 | 1929-10-18 | Process for the preparation of benzimidazolone-5-stibic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146548A (en) |
-
1929
- 1929-10-18 CH CH146548D patent/CH146548A/en unknown
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