AT258923B - Process for the preparation of new 1,3-diazafluoranthene-1-oxides - Google Patents

Description

  

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  Process for the preparation of new 1,3-diazafluoranthene-l-oxides
The invention relates to a process for the preparation of new derivatives of 1-aminofluorenone.



   The compounds prepared according to the invention are the 1,3-diazafluoranthene-1-oxide of the general formula
 EMI1.1
 
 EMI1.2
 
 EMI1.3
 cyclic group which may be substituted e.g. B. a morpholino, piperidino, hexamethyleneimino, piperazino group or a substituted piperazino group.



   The following compounds and their hydrochlorides may be mentioned as examples of compounds of the formula (I)
 EMI1.4
 

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 EMI2.1
 
 EMI2.2
 

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 becomes. The hydrochloride separates out as a precipitate. After recrystallization from methanol, yellow microcrystals with a melting point of 223-2250 ° C. (decomp.) Are obtained.



   Example 5: Preparation of 6-chloro-2-morpholinomethyl-1,3-diazafluoranthene-1-oxide and its hydrochloride.



   600 mg (0.002 mol) of 6-chloro-2-chloromethyl-1,3-diazafluoranthene-1-oxide are stirred in the presence of 2 cm 3 of morpholine in 20 cm 3 of anhydrous methanol. The product is isolated in the usual way and purified by recrystallization from a mixture of benzene and petroleum ether. Yellow-orange needles with a melting point of 169-1700 ° C. are obtained in a yield of 910/0.



   The hydrochloride is prepared in the usual way. It melts at 217-2180 ° C. (decomp.) After recrystallization from a mixture of methanol and ether. (Yellow microcrystals.)
Many compounds of formula I have been tested to determine their pharmacological properties. These connections have an obvious impact on spontaneous motility, which in certain cases is greatly reduced. This sedating and sometimes hypnotic effect is demonstrated by special experiments, e.g. B. the torsion bar test and the Courvoisier tensile test, confirmed. The products also have a protective effect against electric shock and a hypothermic effect.



   Further experiments have shown that compounds of the formula I, namely 2-morpholinomethyl- - 1, 3-diazafluoranthene-1-oxide and 2 - piperidinomethyl - 1, 3 - diazafluoranthene-1-oxide have sedative, anticonvulsant, antiparkinsonian and antispasmodic effects to have.



   Under these circumstances, the compounds of the formula I prepared according to the invention can be used in particular in sedating or calming preparations, in sleeping pills or prenarcotic preparations and in anticonvulsant preparations, antiparkinsonian preparations or antispasmodic agents.



   The new compounds of the formula I can be administered orally in any known application form or intramuscularly or intravenously.

 

Claims (1)

PATENT CLAIM: EMI3.1 EMI3.2 EMI3.3 EMI3.4 EMI3.5 <Desc / Clms Page number 4> EMI4.1 in which R, and Rs are hydrogen or a lower alkyl group, such as methyl, and R4 is hydrogen or halogen, such as chlorine, where R is in position 4 or 6, and X is halogen, such as chlorine or bromine with morpholine in methanol or with a corresponding nitrogen-containing saturated heterocyclic compound such as piperidine, morpholine or hexamethyleneimine is reacted in tetrahydrofuran.