AT40963B - Process for the preparation of p-ethoxyphenylaminomethylsulphurous acid salts. - Google Patents
Process for the preparation of p-ethoxyphenylaminomethylsulphurous acid salts.Info
- Publication number
- AT40963B AT40963B AT40963DA AT40963B AT 40963 B AT40963 B AT 40963B AT 40963D A AT40963D A AT 40963DA AT 40963 B AT40963 B AT 40963B
- Authority
- AT
- Austria
- Prior art keywords
- acid salts
- preparation
- ethoxyphenylaminomethylsulphurous
- clinical trials
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- QMLLUTUQHWNQQS-UHFFFAOYSA-N CCOC(C=C1)=CC=C1NCS(O)(O)=O Chemical class CCOC(C=C1)=CC=C1NCS(O)(O)=O QMLLUTUQHWNQQS-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 p-ethoxyphenylaminomethylsulfuric acid salts Chemical class 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 229960003893 phenacetin Drugs 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
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EMI2.1
ist. Die p-äthoxyphenylaminomethylschwefligsauren Salze, die, wie erwähnt, noch nicht be- schrieben sind, zeichnen sich vorden bekannten #-Sulfomethylverbindungen primärer, aromatischer Amine durch ihre therapeutische Wirksamkeit aus. An eine therapeutische Verwendung der p-äthoxyphenylaminomethylschwefligsauren Salze konnte erst gedacht werden, nachdem Verfahren zu ihrer Herstellung in unzersetztem Zustande gefunden war. Die bisher stets beobachtete Gelbfärbung bei Anwendung der bekannten Arbeitsweise deutete auf das Auftreten. von Zersetzungen. Für therapeutische Zwecke können aber nur reine, von zufälligen, in ihren
EMI2.2
bindungen benutzt werden.
Die mit den nach dem vorliegenden Verfahren erhältlichen p-äthoxyphenyiaminomethyl- schwefligsauren Salzen angestellten klinischen Versuche haben ergeben, dass die Giftigkeit des p-Phenetidins in den neuen Verbindungen unter Beibehaltung der antineuralgischen und antipyretischen Eigenschaften der freien Base stark herabgemindert ist. Die therapeutische Wirksamkeit der p-äthoxyphenylaminometbylschwefligsauren Salze ist umso auffallender, als nach den bisherigen Beobachtungen der Eintritt einer Säuregruppe in das Molekül des Antifebrins und Phenazetins eine Vernichtung der fieberstillenden Eigenschaften herbeiführt (Fränkel, "Arzneimittel-Synthese", 2. Aufl., [1906], S. 275-276).
Die klinischen Versuche haben ergeben, dass die p-äthoxyphenylaminomethylschwefligsauren Salze im Vergleiche zum Phenazetin und Laktophenin wesentlich günstiger wirken. Auffallend ist auch, dass die Salze, wie die klinischen Versuche gezeigt haben, nicht giftig wirken.
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EMI1.1
EMI1.2
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is. The p-ethoxyphenylaminomethylsulfuric acid salts, which, as mentioned, have not yet been described, are distinguished from the known # -sulfomethyl compounds of primary aromatic amines by their therapeutic effectiveness. A therapeutic use of the p-ethoxyphenylaminomethylsulphurous acid salts could only be considered after a method for their preparation in the undecomposed state had been found. The yellow coloration that has always been observed so far when using the known procedure indicated the occurrence. of decomposition. For therapeutic purposes, however, only pure, accidental, in their
EMI2.2
bindings are used.
The clinical trials carried out with the p-ethoxyphenyiaminomethyl sulphurous acid salts obtained by the present process have shown that the toxicity of p-phenetidine in the new compounds is greatly reduced while maintaining the antineuralgic and antipyretic properties of the free base. The therapeutic effectiveness of the p-ethoxyphenylaminomethylsulfuric acid salts is all the more striking as, according to previous observations, the entry of an acid group into the molecule of antifebrin and phenacetine destroys the antipyretic properties (Fränkel, "Arzneimittel -ynthesis", 2nd ed., [1906 ], Pp. 275-276).
The clinical trials have shown that the p-ethoxyphenylaminomethylsulfurous acid salts have a much more favorable effect compared to phenacetine and lactophenine. It is also noticeable that, as clinical trials have shown, the salts are not toxic.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT40963T | 1908-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT40963B true AT40963B (en) | 1910-02-10 |
Family
ID=3559584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT40963D AT40963B (en) | 1908-09-25 | 1908-09-25 | Process for the preparation of p-ethoxyphenylaminomethylsulphurous acid salts. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT40963B (en) |
-
1908
- 1908-09-25 AT AT40963D patent/AT40963B/en active
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