PL148243B1 - Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one - Google Patents

Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one Download PDF

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Publication number
PL148243B1
PL148243B1 PL26438187A PL26438187A PL148243B1 PL 148243 B1 PL148243 B1 PL 148243B1 PL 26438187 A PL26438187 A PL 26438187A PL 26438187 A PL26438187 A PL 26438187A PL 148243 B1 PL148243 B1 PL 148243B1
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Poland
Prior art keywords
dihydro
chlorofhenyl
methylisoxazolo
pyridin
obtaining novel
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PL26438187A
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Polish (pl)
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PL264381A1 (en
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Priority to PL26438187A priority Critical patent/PL148243B1/en
Publication of PL264381A1 publication Critical patent/PL264381A1/en
Publication of PL148243B1 publication Critical patent/PL148243B1/en

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Przedmiotem wynalazku jest sposób wytwarzania nowego 5-/4-chlorofenyl o/-3-metylo- izoksazolo- /5,4 - d/ - 6,7 - dihydro- /?*i/ - pirymidyn - 4-onu o wzorze 1, stanowiace¬ go pólprodukt do wytwarzania pochodnych wykazujacych wysoka aktywnosc przeciwdrgawkowa i przeciwbólowa.Wedlug wynalazku sposób wytwarzania nowego 5- /4-chlorofenylo/-3-metyloizoksazolo - ~/5|4-4/ - 6,7 - dihydro- /Te/ - pirymidyn - 4-onu o wzorze 1 polega na cyklizacji podsta¬ wionego 4-fenyloamidu kwasu 5-amino-3-metylo-4-izoksazolokarboksylowego za pomoca alde¬ hydu mrówkowego lab formamidu.Wytworzony zwiazek poddany nastepnie acetalowaniu ortomrowczasem trietylowym prowa¬ dzi do powstania 5-/4-chlorofenylo/-4-dietoksymetinoksy - 4-etoksy-3-metyloizoksazoloy - /5,4- ksyetylóamina, hydroksyetyloaminoetyloamina, dietyloaminoetyloamina, alliloamina, mor- folina, hydroksyetylopiperazyna lub benzyloamina prowadzi do wytworzenia nowych pochod¬ nych 5-fenylo-3-metyloizoksazolo- /5,4- ogólnym 3, w którym R oznacza grupe aminowa odpowiednia do wymienionych wyzej amin.Zwiazki o wzorze ogólnym 1 wykazuja aktywnosc przeciwdrgawkowa i przeciwbólowa.Aktywnosc przeciwdrgawkowa badano w tescie maksymalnego szoku elektrycznego i w tescie znoszenia drgawek wywolanych pentetrazolem, osiagajac calkowite zniesienie objawów.Dzialanie przeciwbólowe oceniono w tescia czolgania, który wykazal zmniejszenie reakcji na ból do okolo 60$.Przedmiot wynalazku jest przedstawiony w dwóch przykladach wykonania.2 148 243 Przyklad I* 2,5 g /0,01 mola/ -p-chloroanilidu kwa a a 5-amino-3-metylo- 4-izoksazolokarboksylowego ogrzewa sie przez 2 godziny w temperaturze 312-352 K w roz- 3 3 tworze 20 cm etanolu i 5 cm' formaldehydu, Boztwór poreakcyjny ochladza sie i odsa¬ cza wydzielony osad w ilosci 2,1 g, z wydajnoscia 80,8$ wydajnosci teoretycznej* Tem¬ peratura topnienia wytworzonego zwiazku wynosi 470 - 472 K* Przyklad II* 2,5 g /0,01 mola/ p-chloroanilidu kwasu 5-amino-3-metylo- 4-izokaazolokarboksylowego ogrzewa sie przez 2-3 godziny w temperaturze 373-390 K z 3 3 5 cm' formamidu* Mieszanine poreakcyjna miesza sie z 20 cm wody i odsacza wydzielony osad* Otrzymuje sie 2,3 g produktu, z wydajnoscia 85 % wydajnosci teoretycznej* Tempera¬ tura topnienia wytworzonego zwiazku wynosi 470-472 K* Zastrzezenie patentowe Sposób wytwarzania nowego 5- /4-chlorofenylo/-3-metyloizoksazolo- /5,4 - 47 - 6,7 - dihydro-/7H/-pirynidyn-4-onu o wzorze. 1, znamienny tym, ze pod¬ stawiony 4-fenyloamld kwasu 5-amino-3-metylo-4-izoksazolokarboksylowego cyklizuje sie za pomoca aldehydu mrówkowego lub formamidu* Wzbr3 Pracownia Poligraficzna UP PRL. Naklad 100 Cena 400 zl PLThe subject of the invention is a process for the preparation of a new 5- (4-chlorophenyl) -3-methyl-isoxazole- (5.4-d) - 6.7-dihydro- (α * and) -pyrimidin-4-one of the formula which is an intermediate for the preparation of derivatives exhibiting high anticonvulsant and analgesic activity. of the pyrimidine-4-one of the formula I consists in the cyclization of the substituted 4-phenylamide of 5-amino-3-methyl-4-isoxazole carboxylic acid with the formaldehyde lab formamide. The compound produced, then subjected to triethyl ortho acetalization, leads to the formation of 5- (4-chlorophenyl) -4-diethoxymethinoxy-4-ethoxy-3-methylisoxazole - (5,4-xyethylamine, hydroxyethylaminoethylamine, diethylaminoethylamine, allylamine, morpholine, hydroxyethylpiperazine or benzylamine leads to the production of new 5-phenyl derivatives -3-methylisoxazole- (5,4-general 3, wherein R is the group am Compounds of general formula I have anticonvulsant and analgesic activity. Anticonvulsant activity was tested in the maximal electric shock test and in the pentetrazole-induced seizure management test, achieving complete relief of symptoms. pain up to about 60 $. The subject of the invention is presented in two embodiments. 2 148 243 Example I * 2.5 g (0.01 mol) -p-chloroanilide of 5-amino-3-methyl-4-isoxazole carboxylic acid is heated for 2 hours at a temperature of 312-352 K in a solution of 20 cm of ethanol and 5 cm of formaldehyde, the reaction solution is cooled and the separated precipitate is filtered off in the amount of 2.1 g, with the theoretical yield of 80.8 The melting point of the compound formed is 470 - 472 K. EXAMPLE II 2.5 g (0.01 mol) of 5-amino-3-methyl-4-isocaazole carboxylic acid p-chloroanilide is heated for 2-3 hours. At a temperature of 373-390 K from 3 3 5 cm of formamide * The reaction mixture is mixed with 20 cm of water and the separated precipitate is filtered off * 2.3 g of the product are obtained, the yield of 85% of theoretical yield * The melting point of the compound produced is 470-472 K * Claim Process for the preparation of a new 5- (4-chlorophenyl) -3-methylisoxazole- (5.4-47-6.7-dihydro- (7H) -pyrinidin-4-one of the formula. The method of claim 1, characterized in that the substituted 4-phenylamide of 5-amino-3-methyl-4-isoxazole carboxylic acid is cyclized with formaldehyde or formamide. Wzbr3 Pracownia Poligraficzna UP PRL. Mintage 100 Price PLN 400 PL

Claims (5)

1. Zastrzezenie patentowe1. Patent claim 2. Sposób wytwarzania nowego 5- /4-chlorofenylo/-2. The method of producing new 5- (4-chlorophenyl) - 3. -metyloizoksazolo- /5,4 - 47 - 6,7 - dihydro-/7H/-pirynidyn-4-onu o wzorze. 1, znamienny tym, ze pod¬ stawiony3-methylisoxazole (5.4-47-6.7-dihydro (7H) -pyrinidin-4-one of the formula. As in claim 1, characterized in that 4. -fenyloamld kwasu4. Acid phenylamld 5. -amino-3-metylo-4-izoksazolokarboksylowego cyklizuje sie za pomoca aldehydu mrówkowego lub formamidu* Wzbr3 Pracownia Poligraficzna UP PRL. Naklad 100 Cena 400 zl PL5. -amino-3-methyl-4-isoxazole carboxylic is cyclized with formaldehyde or formamide * Wzbr3 Pracownia Poligraficzna UP PRL. Mintage 100 Price PLN 400 PL
PL26438187A 1987-03-02 1987-03-02 Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one PL148243B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL26438187A PL148243B1 (en) 1987-03-02 1987-03-02 Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL26438187A PL148243B1 (en) 1987-03-02 1987-03-02 Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one

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PL264381A1 PL264381A1 (en) 1988-09-15
PL148243B1 true PL148243B1 (en) 1989-09-30

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PL26438187A PL148243B1 (en) 1987-03-02 1987-03-02 Method of obtaining novel 5- 4-chlorofhenyl-3-methylisoxazolo-5,4-d-6,7-dihydro-7h-pyridin-4-one

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