Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same
a technology of substituted alkylaminopyridazinone and alkylaminopyridazinone, which is applied in the direction of drug compositions, heterocyclic compound active ingredients, organic chemistry, etc., can solve the problems of low addictive potential, withdrawal symptoms, and major disadvantages of sedative and amnestic side effects of these drugs, so as to reduce blood pressure of test animals, improve retention of memory, and increase the effect of augmented latency
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example 1
Preparation of 5-{2-[4-(methoxytrifluoromethylphenyl)-piperazine-1-yl]-ethylamino}-2H-pyridazine-3-one trihydrochloride
3.7 g (0.0086 moles) of 4-chloro-5-{2-[4-(methoxy-trifluoromethyl-phenyl)piperazine-1-yl]ethylamino}-H-pyridazine-3-one, 370 cm3 of methanol, 3.2 cm3 (0,018 moles) of diisopropyl-ethylamine and 3.7 g of palladium on carbon catalyst consisting of 8% of Pd, 28% of C and 64% of H2O are transferred into an autoclave. The reaction mixture is stirred at room temperature and under a hydrogen pressure of 10 atm for 4 hours. Then, the excess hydrogen is let out from the autoclave, the reaction mixture is heated to reflux temperature and stirred at this temperature for 5 minutes, then filtered while hot, and the catalyst is washed three times using 33 cm3 of a 1:1 mixture of methanol and dichloromethane each time. The combined filtrates are evaporated under reduced pressure, and the residue is subjected to chromatography over a silica gel column using a 19:1 mixture of chl...
example 2
Preparation of 5-{2-[4-(2-fluorophenyl)piperazine-1-yl]ethyl-amino}-2H-pyridazine-3-one
2.5 g (0.0071 moles) of 4-chloro-5-{2-[4-(2-fluorophenyl)piperazine-1-yl]ethylamino}-2H-pyridazine-3-one, 400 cm3 of a 9:1 mixture of methanol and distilled water and 2.5 g of palladium on carbon catalyst consisting of 8% of Pd, 28% of C and 64% of H2O are weighed into an apparatus of 1000 cm3 volume equipped with a reflux condenser connected to a bubbling device. 1.4 cm3 of hydrazine hydrate are added, drop by drop, to the reaction mixture that is then stirred at reflux temperature for 1 hour. The mixture is filtered while hot, and the catalyst is washed three times using 33 cm3 of a 1:1 mixture of methanol and dichloromethane. The combined filtrates are evaporated, and the residue is dissolved in 25 cm3 of a 8:1 filtered, and the filtrate is evaporated to the fifth of the original volume. After cooling, the crystals separated are stirred for further half an hour under cooling with ice water, ...
example 3
Preparation of 5-{2-[4phenylpiperazine-1-yl]ethylamino}2H-pyridazine-3-one
3.3 g (0.01 moles) of 4-chloro-5-[2-(4-phenylpiperazine-1-yl)ethylamino]-2H-pyridazine-3-one, 500 cm3 of a 9:1 mixture of methanol and distilled water and 3.3 g of palladium on carbon catalyst consisting of 8% of Pd, 28% of C and 64% of H2O are weighed into an apparatus of 1000 cm3 volume equipped with a reflux condenser connected to a bubbling device. 2 cm3 of hydrazine hydrate are added, drop by drop, to the reaction mixture that is then stirred at reflux temperature for 3 hours. The mixture is filtered while hot, and the catalyst is washed three times using 33 cm3 of a 1:1 mixture of methanol and dichloromethane. The combined filtrates are evaporated, and the residue is dissolved in 15 cm3 of a 8:1 mixture of ethanol and water under heating, the solution is filtered, and the filtrate is evaporated to the fourth of the original volume. After cooling, the crystals separated are stirred for further half an ...
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