PL148241B1 - Method of obtaining novel 5-/4-chlorophenyl/-3-methyl-6-trichloromethylisoxazolo-5,4-d-6,7-dihydro-7h-pyrimidin-4-one - Google Patents
Method of obtaining novel 5-/4-chlorophenyl/-3-methyl-6-trichloromethylisoxazolo-5,4-d-6,7-dihydro-7h-pyrimidin-4-one Download PDFInfo
- Publication number
- PL148241B1 PL148241B1 PL26438487A PL26438487A PL148241B1 PL 148241 B1 PL148241 B1 PL 148241B1 PL 26438487 A PL26438487 A PL 26438487A PL 26438487 A PL26438487 A PL 26438487A PL 148241 B1 PL148241 B1 PL 148241B1
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- PL
- Poland
- Prior art keywords
- methyl
- chlorophenyl
- pyrimidin
- dihydro
- trichloromethylisoxazolo
- Prior art date
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- CNZBKZVKOBKIOR-UHFFFAOYSA-N 5-amino-3-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(N)=C1C(O)=O CNZBKZVKOBKIOR-UHFFFAOYSA-N 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- -1 mcrfoline Chemical compound 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- FBYQIYSAUFWXQK-UHFFFAOYSA-N 3-methyl-5-phenyl-1,2-oxazole Chemical class O1N=C(C)C=C1C1=CC=CC=C1 FBYQIYSAUFWXQK-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- ZIEYWRMAWWXAHM-UHFFFAOYSA-N CC(C1(O)OC)=NOC1C(C=C1)=CC=C1Cl Chemical compound CC(C1(O)OC)=NOC1C(C=C1)=CC=C1Cl ZIEYWRMAWWXAHM-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowego 5-/4-chlorofenylo/-3-metylo- -6-trichlorometyloizoksazolo- /5,4- rze 1, stanowiacego pólprodukt do wytwarzania pochodnych wykazujacych wysoka aktywnosc przeciwdrgawkowa i przeciwbólowa.Wedlug wynalazku sposób wytwarzania nowego 5-/4-chlorofenyl^/-3-netylo-6-trichloro- metyloizoksazolo - ^5,4 - 4/ - 6,7 - dihydro - £l)tf - pirymidyn - 4-onu o wzorze 1 pole¬ ga na tym, ze podstawiony 4-fenyloamid kwasu 5-amino-3-metylc-4-izoksazolokarboksylowego cyklizuje sie za pomoca aldehydu trichlorooctowego* Wytworzony zwiazek poddany nastepnie acetalowaniu za pomoca metanolu prowadzi do powstania 5- /4-chlorofenylo/- 4-hydroksy - 4-metoksy - 3-metyloizoksazolo - /5,4 -d/ - 6,7-dihydro - fnj? - pirymidyny o wzorze 2, która poddana aminolizie hydroksyetyloamina, hydroksyetyloaminoetyloamina, dietyloaminoetyloamina, alliloamina, mcrfolina, hydroksy- etylopiperazyna lub benzyloamina prowadzi do wytworzenia nowych pochodnych 5-fenylo- 3-metyloizoksazolo -/54 - d7 - 6,7 - dihydro - /7ll/ - pirymidyn o wzorze ogólnym 3, w którym H oznacza grupe aminowa odpowiednia do wymienionych wyzej amin* Zwiazki o wzorze ogólnym 3 wykazuja aktywnosc przeciwdrgawkowa i przeciwbólowa. Aktyw¬ nosc przeciwdrgawkowa badano w tescie maksymalnego szoku elektrycznego i w tescie zno¬ szenia drgawek wywolanych pentetrazolem, osiagajac calkowite zniesienie objawów. Dziala¬ nie przeciwbólowe oceniono w tescie czolgania, który wykazal zmniejszenie reakcji na ból do okolo 60 %.Przedmiot wynalazku Jest przedstawiony w przykladzie wykonania.Przyklad. 12,6 g /0,05 mola/ p-chlorofenyloamidu kwasu 5-amino-3-oetylo-4-izoksazolokar- boksylowego ogrzewa sie przez 2 godziny na lesni wodnej z 11 g /0,075 mola/ aldehydu tri-2 148 241 chlorooctowego w 30 g benzenu* Po ochlodzeniu odsacza sie wydzielony osad. Otrzymuje sie 12 g produktu, z wydajnoscia równa 78 % wydajnosci teoretycznej, którego temperatura top¬ nienia wynosi 423-424 K.Zastrzezenie patentowe Sposób wytwarzania nowego 5-/4-chlorofenylo/-3-metylo-6-trichlorometyloizoksazolo- - /5,4-d/ - 6,7 - dlhydro - flYjf - pirymidyn -4-onu o wzorze 1, znamienny tym, te podstawiony 4-fenyloamid kwasu 5-amino-3-netylo-4-izoksazolokarboksylowego cyklizuje sie za pomoca aldehydu trichlorooctowego.Wzbr 1 Wzbr 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 400 zl PLThe subject of the invention is a process for the preparation of the new 5- (4-chlorophenyl) -3-methyl-6-trichloromethylisoxazole- (5,4-rhe 1), which is an intermediate for the production of derivatives showing high anticonvulsant and analgesic activity. (4-chlorophenyl) - 3-nethyl-6-trichloromethylisoxazole - (5,4 - 4) - 6,7 - dihydro - l) tf - pyrimidine - 4-one of the formula (I) consists of: that the substituted 5-amino-3-methylc-4-isoxazole carboxylic acid 4-phenylamide is cyclized with trichloroacetic aldehyde * The resulting compound, then acetalised with methanol, leads to the formation of 5- (4-chlorophenyl) - 4-hydroxy-4-methoxy - 3-methylisoxazole - (5,4-d) - 6,7-dihydro-fnj - pyrimidines of formula 2, which, when subjected to aminolysis, hydroxyethylamine, hydroxyethylaminoethylamine, diethylaminoethylamine, allylamine, mcrfoline, hydroxyethylpiperazine or benzylamine leads to the production of new 5-phenyl-3-methylisoxazole derivatives - / 54 - d7 - 6.7 - dihydro - pyrimidines of general formula III, in which H is an amino group suitable for the amines mentioned above. Compounds of general formula III have anticonvulsant and analgesic activity. The anticonvulsant activity was tested in the maximum electric shock test and in the pentetrazole-induced epilepsy relief test, achieving complete symptom relief. The analgesic effect was assessed in a traverse test, which showed a reduction in pain response to about 60%. The subject of the invention is illustrated in the example of the embodiment. 12.6 g (0.05 mole) of 5-amino-3-oethyl-4-isoxazole-carboxylic acid p-chlorophenylamide is heated for 2 hours in a water forest with 11 g (0.075 mole) of tri-2 148 241 chloroacetic aldehyde in 30 g of benzene * After cooling, the separated precipitate is filtered off. 12 g of the product are obtained with a yield equal to 78% of theoretical yield, the melting point of which is 423-424 K. Patent claim Process for the production of a new 5- (4-chlorophenyl) -3-methyl-6-trichloromethylisoxazole-5, 4-d / - 6,7-dlhydro-flYjf-pyrimidin-4-one of formula 1, characterized in that the substituted 5-amino-3-netyl-4-isoxazole carboxylic acid 4-phenylamide is cyclized with trichloroacetic aldehyde. 1 Wzbr 3 Printing House of the Polish People's Republic. Mintage 100 copies Price PLN 400 PL
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26438487A PL148241B1 (en) | 1987-03-02 | 1987-03-02 | Method of obtaining novel 5-/4-chlorophenyl/-3-methyl-6-trichloromethylisoxazolo-5,4-d-6,7-dihydro-7h-pyrimidin-4-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26438487A PL148241B1 (en) | 1987-03-02 | 1987-03-02 | Method of obtaining novel 5-/4-chlorophenyl/-3-methyl-6-trichloromethylisoxazolo-5,4-d-6,7-dihydro-7h-pyrimidin-4-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL264384A1 PL264384A1 (en) | 1988-09-15 |
| PL148241B1 true PL148241B1 (en) | 1989-09-30 |
Family
ID=20035226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL26438487A PL148241B1 (en) | 1987-03-02 | 1987-03-02 | Method of obtaining novel 5-/4-chlorophenyl/-3-methyl-6-trichloromethylisoxazolo-5,4-d-6,7-dihydro-7h-pyrimidin-4-one |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL148241B1 (en) |
-
1987
- 1987-03-02 PL PL26438487A patent/PL148241B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL264384A1 (en) | 1988-09-15 |
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