AT136002B - Process for the preparation of acylaminobenzenestibinic acids. - Google Patents
Process for the preparation of acylaminobenzenestibinic acids.Info
- Publication number
- AT136002B AT136002B AT136002DA AT136002B AT 136002 B AT136002 B AT 136002B AT 136002D A AT136002D A AT 136002DA AT 136002 B AT136002 B AT 136002B
- Authority
- AT
- Austria
- Prior art keywords
- acids
- preparation
- acylaminobenzenestibinic
- aminobenzenestibinic
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 12
- 150000007513 acids Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000005254 oxyacyl group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- AQTIRDJOWSATJB-UHFFFAOYSA-K antimonic acid Chemical group O[Sb](O)(O)=O AQTIRDJOWSATJB-UHFFFAOYSA-K 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 208000037972 tropical disease Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Aeylaminobenzolstibinsäuren.
In der Patentschrift Nr. 133895 ist ein Verfahren zur Darstellung von Acylaminobenzolstibin- säuren beschrieben, das darin besteht, dass man in Acylaminoanilinderivate, welche in einer o-Stellung zur primären Aminogruppe eine OH-, Oh3-, CH3-Gruppe oder Halogen enthalten, während die andere o-Stellung unbesetzt ist, und die im übrigen beliebig substituiert sein können, über den Diazoweg nach üblichen Methoden den Antimonsäurerest einführt.
Es wurde nun gefunden, dass man die gleichen Verbindungen, die eine hervorragende perorale
Wirkung bei Trypanosomenerkrankungen und andern Tropenkrankheiten aufweisen, durch Acylierung von Aminobenzolstibinsäuren. welche in einer o-Stellung zum Stibinsäurerest eine OH-, OCH3-, CH3-
Gruppe oder Halogen enthalten, während die andere o-Stellung unbesetzt ist, und die im übrigen beliebig substituiert sein können, mit den hiefür üblichen Aeylierungsmitteln, ausgenommen Oxyacylreste enthaltende (diesbezüglich s. Patentschrift Nr. 129770), erhalten kann.
Beispiel : 28 g 4-Amino-2-methylbenzolstibinsäure- (1), hergestellt durch Umsetzen von diazo- tiertem 4-Nitro-l-amino-2-methylbenzol mit Natriumantimonit und Reduktion der so erhaltenen4-Nitrr- 2-methylbenzolstibinsäure- (1), werden in Form des Natriumsalzes in 150 cm3 Wasser gelöst. Unter
Rühren lässt man bei Zimmertemperatur 15 g Essigsäureanhydrid zufliessen und rührt, bis die Temperatur wieder gefallen ist. Dann setzt man Salzsäure zu, bis die Lösung kongosauer ist, saugt ab und reinigt die so gewonnene Stibinsäure, indem man sie in Methylalkohol löst, vom Ungelösten absaugt und mit Äther fällt.
Man erhält die 4-Acetamino-2-methylbenzolstibinsäure-(1) als weisses, in verdünnten Alkalien leicht lösliches Pulver, das beim Erhitzen verkohlt, ohne zu schmelzen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of aeylaminobenzenesibinic acids.
Patent specification No. 133895 describes a process for the preparation of acylaminobenzolestibin acids which consists in converting into acylaminoaniline derivatives which contain an OH, Oh3, CH3 group or halogen in an o-position to the primary amino group the other o-position is unoccupied, and which can otherwise be substituted as desired, introduces the antimonic acid residue via the diazo route according to customary methods.
It has now been found that one can obtain the same compounds that produce an excellent peroral
Have an effect on trypanosomal diseases and other tropical diseases by acylating aminobenzenestibinic acids. which in an o-position to the stibic acid residue is an OH-, OCH3-, CH3-
Contain group or halogen, while the other o-position is unoccupied, and which can otherwise be substituted as desired, with the aylating agents customary for this purpose, with the exception of those containing oxyacyl radicals (in this regard see patent specification No. 129770).
Example: 28 g of 4-amino-2-methylbenzenestibinic acid (1), prepared by reacting diazo-tated 4-nitro-1-amino-2-methylbenzene with sodium antimonite and reducing the 4-nitrr-2-methylbenzenestibic acid (1 ), are dissolved in 150 cm3 of water in the form of the sodium salt. Under
15 g of acetic anhydride are allowed to flow in at room temperature and the mixture is stirred until the temperature has fallen again. Then hydrochloric acid is added until the solution is acidic to the Congo, and the stibic acid obtained in this way is filtered off and purified by dissolving it in methyl alcohol, sucking off the undissolved material and falling with ether.
The 4-acetamino-2-methylbenzenestibinic acid- (1) is obtained as a white powder which is easily soluble in dilute alkalis and which carbonizes on heating without melting.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE136002X | 1929-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT136002B true AT136002B (en) | 1933-12-27 |
Family
ID=29277928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT136002D AT136002B (en) | 1929-06-15 | 1930-05-15 | Process for the preparation of acylaminobenzenestibinic acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT136002B (en) |
-
1930
- 1930-05-15 AT AT136002D patent/AT136002B/en active
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