AT71175B - Process for the preparation of salizyloyl theobromine. - Google Patents
Process for the preparation of salizyloyl theobromine.Info
- Publication number
- AT71175B AT71175B AT71175DA AT71175B AT 71175 B AT71175 B AT 71175B AT 71175D A AT71175D A AT 71175DA AT 71175 B AT71175 B AT 71175B
- Authority
- AT
- Austria
- Prior art keywords
- theobromine
- salizyloyl
- preparation
- derivatives
- parent patent
- Prior art date
Links
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 title claims description 22
- 229960004559 theobromine Drugs 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000007127 saponification reaction Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
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Verfahren zur Darstellung von Salizyloyltheobromin.
Durch das Stammpatent Nr. 71174 ist ein Verfahren zur Darstellung von O-Azidylderivaten des Salizyloyltheobromins der allgemeinen Formel :
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geschützt. Die therapeutische Bedeutung, welche, wIe in dem Stammpatente dargelegt ist, den Salizyloylderivaten des Theobromins zukommt, liess es wünschenswert erscheinen, auch das freie Sa1izyloyltheobromin darzustellen, da zu erwarten war, dass diesem infolge der freien Phenolhydroxylgruppe eine noch schnellere therapeutische Wirkung zukommt.
Der Gedanke, das Salizyloyltheobromin nach Art seiner Azidylderivate durch Einwirkung von freiem Salizyloylchlorid auf Theobromin zu gewinnen, liess sich bis jetzt nicht durchführen, da die bei jenen Säurechloriden vorhandene Neigung zur Bildung innerer Anhydride in noch grösserem Masse vorhanden ist. Tatsächlich erhält man auch bei der Einwirkung von Satizyloyichlorid auf Theobromin oder dessen Salze in der Hauptsache stickstofffreie. sallzylidartige Verbindungen.
Es gelingt jedoch, zu dem bisher noch nicht bekannten Salizyloyltheobromin zu gelangen, wenn man die in dem Stammpatente beschriebenen O-Azidylderivate unter sehr vorsichtigen Bedingungen verseift. Dieser Reaktionsverlauf war nicht zu erwarten, da zu befürchten stand, dass verseifende Mittel sofort zu einem Zerfall in Theobromin und Salizyl- säure führen würden. Tatsächlich tritt dieser Reaktionsverlauf auch ein, wenn nicht unter besonderen Vorsichtsmassregeln gearbeitet \\ird.
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und Natriumkarbonat, etwas schwerer in Bikarbonat, mit der für N-Salizyloylverbindungen charakteristischen gelben Farbe. In alkoholischer Lösung geben sie mit Eisenchlorid eine tief blutrote Färbung.
B e i s p i e l 2 : Schüttelt man Azetsalizyloyitheobromin (Beispie) 1 und 2 des Stamm-
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**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
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Process for the preparation of salizyloyl theobromine.
The parent patent No. 71174 provides a process for the preparation of O-azidyl derivatives of salizyloyl theobromine of the general formula:
EMI1.1
protected. The therapeutic importance of the salizyloyl derivatives of theobromine, as stated in the parent patent, made it appear desirable to also present the free salicyloyl theobromine, since it was to be expected that this would have an even faster therapeutic effect due to the free phenolic hydroxyl group.
The idea of obtaining salizyloyl theobromine in the manner of its azidyl derivatives by the action of free salizyloyl chloride on theobromine could not be carried out until now, since the tendency of these acid chlorides to form internal anhydrides is even greater. In fact, the action of saticyloyichloride on theobromine or its salts mainly results in nitrogen-free. salzylid-like compounds.
However, it is possible to arrive at the hitherto unknown salizyloyl theobromine if the O-azidyl derivatives described in the parent patent are saponified under very careful conditions. This course of the reaction was not to be expected, since it was feared that saponifying agents would immediately break down into theobromine and salicylic acid. In fact, this course of reaction also occurs if special precautionary measures are not taken.
EMI1.2
and sodium carbonate, slightly heavier in bicarbonate, with the yellow color characteristic of N-salizyloyl compounds. In an alcoholic solution they give a deep blood-red color with ferric chloride.
Example 2: If you shake Acetsalizyloyitheobromin (Example) 1 and 2 of the parent
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** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT71174T | 1915-01-04 | ||
| AT71175T | 1915-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT71175B true AT71175B (en) | 1916-02-10 |
Family
ID=25603585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT71175D AT71175B (en) | 1915-01-04 | 1915-01-04 | Process for the preparation of salizyloyl theobromine. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT71175B (en) |
-
1915
- 1915-01-04 AT AT71175D patent/AT71175B/en active
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