DE859470C - Process for the production of therapeutically active substances from theophylline - Google Patents
Process for the production of therapeutically active substances from theophyllineInfo
- Publication number
- DE859470C DE859470C DEB3252D DEB0003252D DE859470C DE 859470 C DE859470 C DE 859470C DE B3252 D DEB3252 D DE B3252D DE B0003252 D DEB0003252 D DE B0003252D DE 859470 C DE859470 C DE 859470C
- Authority
- DE
- Germany
- Prior art keywords
- theophylline
- production
- active substances
- therapeutically active
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Description
Verfahren zur Herstellung von therapeutisch wirksamen Stoffen ' aus Theophyllin Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Stoffen aus Theophyllin mit besonders wertvollen therapeutischen Eigenschaften.Process for the production of therapeutically active substances' from Theophylline The invention relates to a process for the production of new substances made from theophylline with particularly valuable therapeutic properties.
Theophyllin selbst findet bekanntlich als Herz- und Kreislaufmittel sowie als Diureticum in der Heilkunde weitgehende Anwendung, wobei es im allgemeinen nicht unmittelbar, sondern in Form von Salzen bzw. Doppelsalzen oder in Form von Gemischen mit anderen Stoffen angewandt wird.Theophylline itself is known to be used as a cardiovascular drug as well as extensive use as a diuretic in medicine, with it in general not directly, but in the form of salts or double salts or in the form of Mixing with other substances is used.
Hierbei bleibt, das Theophyllinmolekül unverändert erhalten.The theophylline molecule remains unchanged.
Es wurde nun festgestellt, daB die aus Theophyllin durch Einführung von Nitrogruppen entstehenden neuen, bisher unbekannten Nitrotheophyllinverbindungen therapeutische Eigenschaften besitzen. Neben einer verstärkten Theophyllinwirkung zeigt z. B. das Mononitroprodukt u. a. eine erheblich stärker blutdrucksenkende Wirkung als das Theophyllin selbst, die überraschenderweise viel länger anhält.It has now been established that those from theophylline, by introduction new, hitherto unknown nitrotheophylline compounds arising from nitro groups possess therapeutic properties. In addition to an increased theophylline effect shows e.g. B. the mononitro product, inter alia. a much more effective antihypertensive one Effect than the theophylline itself, which surprisingly lasts much longer.
Bei der therapeutischen Anwendung müssen mit Rücksicht auf die Schwerlöslichkeit in Wasser Amine zur Erhöhung der Löslichkeit zugesetzt werden. Ebenso können andere zur Löslichmachung von Theophyllin bekannte Zusätze verwendet werden.When used therapeutically, the poor solubility must be taken into account amines can be added to increase solubility in water. So can others known additives can be used to solubilize theophylline.
Beispiele: ioo Gewichtsteile Theophyllin werden mit etwa 28o Gewichtsteilen einer Salpetersäure vom spezifischen Gewicht D = 1,4 in einem offenen Gefäß unter mäßigem Rühren so lange erwärmt, bis eine lebhafte Entwicklung nitroser Gase eintritt. Hiernach wird mit dem Erwärmen aufgehört, da die Umsetzung selbsttätig zu Ende verläuft. Dia Reaktion ist gegebenenfalls durch Kühlung abzubremsen, und zwar muß die Kühlung so eingestellt werden, daß keine erhebliche Entwicklung von nitrosen Gasen eintritt. Es bildet sich eine gAbliche, dickflüssige brasse. Zur Gewinnung der entstandenen neuen Verbindung wird das Umsetzungsgemisch unter sorgfältigem Durchrühren vorsichtig mit wäßrigem Ammoniak neutralisiert. Hierbei entsteht eine rötlich gefärbte Lösung, aus der nach schwachem Ansäuern mit Salpetersäure die entstandene Nitroverbindung in Form gelber Kristalle ausgeschieden wird. Die Kristalle werden durch WVaschen mit Wasser von d?n anhaftenden Salzen befreit und vorsichtig an der Luft getrocknet. Die Verbindung enthält z N101 Kristallwasser.Examples: 100 parts by weight of theophylline become with about 28o parts by weight a nitric acid of the specific Weight D = 1.4 in an open Warm the vessel, stirring gently, until a vigorous development of nitrous Gas enters. After that, the heating is stopped because the implementation takes place automatically comes to an end. If necessary, the reaction can be slowed down by cooling, and Although the cooling must be adjusted so that no significant development of nitrous gases enter. A typical, viscous bream forms. To the Obtaining the resulting new compound is the implementation mixture under careful Stir carefully neutralized with aqueous ammonia. This creates a reddish colored solution, from which the resulting after weak acidification with nitric acid Nitro compound is precipitated in the form of yellow crystals. The crystals will be freed from adhering salts by washing with water and carefully removed from the Air dried. The compound contains z N101 crystal water.
Die Analyse der kristallwasserhaltigen Verbindung ist folgende: C = 32,5o %, H = 4,26 °/p, N = 26,2o °/,. Die Zusammensetzung entspricht der eines Mononitrotheophy llins.The analysis of the compound containing water of crystallization is as follows: C = 32.5o%, H = 4.26 ° / p, N = 26.2 ° / ,. The composition corresponds to that of one Mononitrotheophy llins.
Schmelzpunkt: Die Verbindung schmilzt unter Zersetzung bei etwa 28o°.Melting point: The compound melts with decomposition at about 280 °.
Löslichkeiten: Die Verbindung ist in Wasser schwer löslich, löst sich ganz ähnlich wie Theophyllin in wäßrigen Aminen.Solubilities: The compound is sparingly soluble in water, it dissolves much like theophylline in aqueous amines.
Mehrere Nitrogruppen können durch Anwendung schärferer Nitrierungsbedingungen eingeführt werden. Die therapeutische Anwendung geschieht in gl°icher Weise wie die des Theophyllins.Multiple nitro groups can be formed by applying more stringent nitration conditions to be introduced. The therapeutic application happens in the same way as that of theophylline.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB3252D DE859470C (en) | 1943-07-11 | 1943-07-11 | Process for the production of therapeutically active substances from theophylline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB3252D DE859470C (en) | 1943-07-11 | 1943-07-11 | Process for the production of therapeutically active substances from theophylline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE859470C true DE859470C (en) | 1952-12-15 |
Family
ID=6953119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB3252D Expired DE859470C (en) | 1943-07-11 | 1943-07-11 | Process for the production of therapeutically active substances from theophylline |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE859470C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE924085C (en) * | 1953-08-01 | 1955-02-24 | Sagitta Werk G M B H | Process for the preparation of nitric acid esters of oxyalkylxanthines |
-
1943
- 1943-07-11 DE DEB3252D patent/DE859470C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE924085C (en) * | 1953-08-01 | 1955-02-24 | Sagitta Werk G M B H | Process for the preparation of nitric acid esters of oxyalkylxanthines |
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