AT219602B - Process for the preparation of new thioxanthene derivatives - Google Patents
Process for the preparation of new thioxanthene derivativesInfo
- Publication number
- AT219602B AT219602B AT822359A AT822359A AT219602B AT 219602 B AT219602 B AT 219602B AT 822359 A AT822359 A AT 822359A AT 822359 A AT822359 A AT 822359A AT 219602 B AT219602 B AT 219602B
- Authority
- AT
- Austria
- Prior art keywords
- thioxanthene
- preparation
- new
- atoms
- thioxanthene derivatives
- Prior art date
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Thioxanthen-Derivaten
Aus der österr. Patentschrift Nr. 205037 (Dr. A. Wander A. G.) ist ein Verfahren zur Herstellung eines therapeutisch wirksamen, basisch substituierten Thioxanthen-Derivats der Formel 1 :
EMI1.1
bekannt. Dabei wird Thioxanthen mit einer Alkalimetall übertragenden Verbindung und N-Methyl-3-ha- logenmethylpiperidin gleichzeitig oder anschliessend in einem inerten Lösungsmittel, das zur Gruppe der aromatischen Kohlenwasserstoffe gehört, umgesetzt.
Ferner ist auch ein Verfahren zur Herstellung therapeutisch wirksamer Thioxanthen-Derivate der For- mel H :
EMI1.2
worin R'einen Alkylrest mit 1-3 C-Atomen oder einen Alkoxyrest mit ebenfalls 1-3 C-Atomen bedeutet, bekannt. Dabei wird ein in 2-Stellung entsprechend substituiertes Thioxanthen mit einer Alkalimetall übertragenden Verbindung und einem Halogensäureester oder Arylsulfonsäureester von l-Methyl- piperidino-3-methanol gleichzeitig oder anschliessend in einem inerten Lösungsmittel umgesetzt.
Es wurde run gefunden, dass in analoger Weise erhaltene Thioxanthen-Derivate der Formel III :
EMI1.3
<Desc/Clms Page number 2>
worin R Wasserstoff ist oder die oben für R'genannte Bedeutung besitzt und R einen geraden oder verzweigtenAlkylrest mit 2-5 C-Atomen darstellt, ebenfalls therapeutisches Interesse besitzen. Diese neuen Thioxanthen-Derivate weisen, wie im Tierversuch festgestellt wurde, eine stimulerende Wirkung auf das Zentralnervensystem auf. Therapeutische Dosen hemmen zentrale spastische Effekte an der Muskulatur und besitzen eine starke Wirkung gegenüber parkinsonartigem Verhalten, d. h. starke Antitremorinwirkung. Diese Verbindungen können daher als Antiparkinson-Mittel und bei depressiven Zuständen therapeutische Verwendung finden.
Gegenstand der Erfindung ist somit ein Verfahren zur Herstellung von neuen Thioxanthen-Dertvaten der allgemeinenFornel (III) sowie von deren Salzen, welches dadurch gekennzeichnet ist, dass man Thioxanthen oder ein in 2-Stellung entsprechend substituiertes Thioxanthen mit einer Alkalimetallübertra- genden Verbindung und gleichzeitig oder nachfolgend mit einem Ester eines Alkylpiperidinomethanols der Formel IV :
EMI2.1
EMI2.2
<Desc / Clms Page number 1>
Process for the preparation of new thioxanthene derivatives
From the Austrian patent specification No. 205037 (Dr. A. Wander A. G.) a process for the preparation of a therapeutically effective, basic substituted thioxanthene derivative of the formula 1 is:
EMI1.1
known. Thioxanthene is reacted with an alkali metal-transferring compound and N-methyl-3-halomethylpiperidine at the same time or subsequently in an inert solvent belonging to the group of aromatic hydrocarbons.
Furthermore, there is also a process for the preparation of therapeutically effective thioxanthene derivatives of the formula H:
EMI1.2
in which R 'denotes an alkyl radical with 1-3 carbon atoms or an alkoxy radical likewise with 1-3 carbon atoms, are known. A thioxanthene correspondingly substituted in the 2-position is reacted with an alkali metal-transferring compound and a halogen acid ester or aryl sulfonic acid ester of 1-methyl-piperidino-3-methanol simultaneously or subsequently in an inert solvent.
It has been found that thioxanthene derivatives of the formula III obtained in an analogous manner:
EMI1.3
<Desc / Clms Page number 2>
in which R is hydrogen or has the meaning given above for R 'and R is a straight or branched alkyl radical having 2-5 carbon atoms, are also of therapeutic interest. As was found in animal experiments, these new thioxanthene derivatives have a stimulant effect on the central nervous system. Therapeutic doses inhibit central spastic effects on the muscles and have a strong effect on Parkinson-like behavior, i. H. strong antitremorin activity. These compounds can therefore find use as antiparkinsonian agents and therapeutic use in depressive states.
The invention thus provides a process for the preparation of new thioxanthene derivatives of the general formula (III) and their salts, which is characterized in that thioxanthene or a thioxanthene correspondingly substituted in the 2-position with an alkali metal transferring compound and simultaneously or below with an ester of an alkylpiperidinomethanol of the formula IV:
EMI2.1
EMI2.2
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT822359A AT219602B (en) | 1959-11-13 | 1959-11-13 | Process for the preparation of new thioxanthene derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT822359A AT219602B (en) | 1959-11-13 | 1959-11-13 | Process for the preparation of new thioxanthene derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
AT219602B true AT219602B (en) | 1962-02-12 |
Family
ID=3603603
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT822359A AT219602B (en) | 1959-11-13 | 1959-11-13 | Process for the preparation of new thioxanthene derivatives |
Country Status (1)
Country | Link |
---|---|
AT (1) | AT219602B (en) |
-
1959
- 1959-11-13 AT AT822359A patent/AT219602B/en active
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