CH148338A - Process for the preparation of 1-ethyl-2-oxobenzimidazole-2,3-dihydride-5-stibic acid. - Google Patents
Process for the preparation of 1-ethyl-2-oxobenzimidazole-2,3-dihydride-5-stibic acid.Info
- Publication number
- CH148338A CH148338A CH148338DA CH148338A CH 148338 A CH148338 A CH 148338A CH 148338D A CH148338D A CH 148338DA CH 148338 A CH148338 A CH 148338A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- dihydride
- ethyl
- oxobenzimidazole
- stibic
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title 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
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 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 5
- 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
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 1-Äthyl-2-ogobenzimidazol-2,3-dihy drid-6-stibinsäure. In dem Hauptpatent wurde die Darstel lung der Benzimidazolon-5-stibinsäure durch Umsetzung von diazotiertem 5-Amino-2-oxo- benzimidazol-2,3-dihydrid mit antimoniger Säure beschrieben.
Es wurde nun gefunden, dass die thera peutisch ebenso wichtige bisher nicht bekannte 1-Äthyl- 2 - oxobenzimidazol - 2,3 - dihydrid - 5- stibinsäure durch Behandlung von dianotier tem 1-Äthyl-5-amino-2-oxobenzimidazol-2,3- diliydrid in analoger Weise entsteht.
Beispiel: 18,76 gr 1-Äthyl-5-amino-2-oxobenzimid- azol-2,3-dihydrid hydrochlorid werden in salz saurer Lösung diäzotiert. Die Diazolösung wird in eine Antimonitlösung eingerührt, die zum Beispiel auf folgende Weise hergestellt werden kann: 16 gr Antimontrioxyd werden in 200 cm' Wasser, 50 cm3 Glycerin und 35 em3 Natronlauge (40" Bö) unter Erwär men gelöst.
Zur Umsetzung wird die Lösung zweckmässig auf Zimmertemperatur abge kühlt. 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 1-Äthyl-2-oxobenz- imidazol-2,3-dihydrid-5-stibinsäure ausfällt. Diese Säure stellt ein in Alkalien leicht lösliches Pulver dar, das beim Erhitzen im Glührohr verkohlt, ohne zu schmelzen. Sie zeichnet sich durch hervorragende Wirkung bei Protozoenerkrankungen aus.
Process for the preparation of 1-ethyl-2-ogobenzimidazole-2,3-dihydride-6-stibic acid. In the main patent, the presen- tation of benzimidazolone-5-stibic acid was described by reacting diazotized 5-amino-2-oxo-benzimidazole-2,3-dihydride with antimony acid.
It has now been found that the therapeutically equally important hitherto unknown 1-ethyl-2-oxobenzimidazole-2,3-dihydride-5-stibic acid by treatment of dianotier tem 1-ethyl-5-amino-2-oxobenzimidazole-2, 3-dihydride is formed in an analogous manner.
Example: 18.76 g of 1-ethyl-5-amino-2-oxobenzimid-azole-2,3-dihydride hydrochloride are diacid in a salt-acid solution. The diazo solution is stirred into an antimonite solution, which can be prepared, for example, in the following way: 16 grams of antimony trioxide are dissolved in 200 cm3 of water, 50 cm3 of glycerine and 35 cubic meters of sodium hydroxide solution (40 "Bo) while heating.
For implementation, the solution is expediently cooled down 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 1-ethyl-2-oxobenzimidazole-2,3-dihydride-5-stibic acid precipitates. This acid is a powder that is easily soluble in alkalis and, when heated in the glow tube, carbonizes without melting. It is characterized by its excellent effect on protozoal diseases.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE148338X | 1928-11-07 | ||
| CH146548T | 1929-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH148338A true CH148338A (en) | 1931-07-15 |
Family
ID=25714878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148338D CH148338A (en) | 1928-11-07 | 1929-10-18 | Process for the preparation of 1-ethyl-2-oxobenzimidazole-2,3-dihydride-5-stibic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH148338A (en) |
-
1929
- 1929-10-18 CH CH148338D patent/CH148338A/en unknown
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