PL193279B1 - Novel leading structure of isoxazolotriazepinone derivative and method of obtaining same - Google Patents
Novel leading structure of isoxazolotriazepinone derivative and method of obtaining sameInfo
- Publication number
- PL193279B1 PL193279B1 PL343181A PL34318100A PL193279B1 PL 193279 B1 PL193279 B1 PL 193279B1 PL 343181 A PL343181 A PL 343181A PL 34318100 A PL34318100 A PL 34318100A PL 193279 B1 PL193279 B1 PL 193279B1
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- Prior art keywords
- isoxazolotriazepinone
- derivative
- obtaining same
- leading structure
- novel leading
- Prior art date
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
. Pochodna izoksazolotriazepinonu o nazwie 3,5-dimetylo-8H-izoksazolo[5,4-e][1,2,4]triazepu-4-on i wzorze przedstawionym na rysunku.. A derivative of isoxazole triazepinone called 3,5-dimethyl-8H-isoxazolo[5,4-e][1,2,4]triazep-4-one and with the formula shown in the figure.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowa pochodna izoksazolotriazepinonu o nazwie 3,5-dimetyIo-8H-izoksazolo[5,4-e][1,2,4]triazepin-4-on i wzorze przedstawionym na rysunku oraz sposób jej wytwarzania. Związek ten wykazuje działanie biologiczne o aktywności immunostymulującej, a także jest przeznaczony do otrzymywania nowych związków o aktywności immunomodulującej.The invention concerns a new isoxazole triazepinone derivative called 3,5-dimethyl-8H-isoxazolo[5,4-e][1,2,4]triazepin-4-one, with the formula shown in the figure, and a method for its preparation. This compound exhibits biological activity with immunostimulating activity and is also intended for the preparation of new compounds with immunomodulating activity.
Podobne związki wykazujące aktywność na ośrodkowy układ nerwowy ( OUN)1, oraz na system immunologiczny2 otrzymali inni twórcy, a mianowicie:Similar compounds showing activity on the central nervous system (CNS) 1 and on the immune system 2 were obtained by other authors, namely:
1. H. Śladowska, M. Bodetko, M. Sieklucka-Dziuba, G. Rajtar, D. Złółkowska, and Z. Kleinrok, Farmaco, 1997, 52(11), 657.1. H. Śladowska, M. Bodetko, M. Sieklucka-Dziuba, G. Rajtar, D. Złółkowska, and Z. Kleinrok, Farmaco, 1997, 52(11), 657.
2. Y. Yamamoto, M. Shindo, and T. Nakamura, PCT Int. Appl. WO 9747622 AI 18 Dec 1997.2. Y. Yamamoto, M. Shindo, and T. Nakamura, PCT Int. Appl. WO 9747622 AI 18 Dec 1997.
Nowy związek o wzorze przedstawionym na rysunku otrzymuje się w wyniku reakcji 1-metylohydrazydu kwasu 5-armno-3-metylo-4-izoksazolo-karboksylowego z ortomrówczanem trietylowym, przy ogrzewaniu w temperaturze wrzenia, w czasie 0,5 - 3 godzin, w roztworach alkoholowych od C-1 do C-4.The new compound with the formula shown in the figure is obtained by reacting 5-amino-3-methyl-4-isoxazole-carboxylic acid 1-methylhydrazide with triethyl orthoformate, heated at reflux for 0.5 - 3 hours, in C-1 to C-4 alcoholic solutions.
Podczas badań nieoczekiwanie okazało się, że nowy związek wykazuje aktywność immunostymulującą przewyższającą Lewamizol. Działanie to wykazane zostało w testach biologicznych przedstawionych w tabeli.During the research, it was unexpectedly revealed that the new compound exhibited immunostimulatory activity superior to that of levamisole. This effect was demonstrated in the biological tests presented in the table.
Przedmiot wynalazku jest przedstawiony na przykładzie wykonania.The subject of the invention is presented in an embodiment example.
Próbkę 3 mmoli metylohydrazydu kwasu 5-amino-3-metyloizoksazolo-4-karbo-ksylowego umieszcza się w kolbie okrągłodennej o pojemności 100 mL, zaopatrzonej w chłodnicę zwrotną i mieszadełko, a następnie dodaje się 50 mL etanolu i 10 mL ortomrówczanu trietylowego. Po osiągnięciu temperatury wrzenia mieszaniny, dodaje się 5 kropli stężonego kwasu solnego. Całość miesza się na mieszadle magnetycznym i ogrzewa w temperaturze wrzenia przez 10 minut. W miarę postępu reakcji mieszanina klaruje się. Po zakończeniu procesu, kontrolowanym na płytkach TLC, roztwór podgęszcza się pod zmniejszonym ciśnieniem do sucha. Do pozostałości dodaje się 50 mL tetrahydrofuranu (THF) i ogrzewa do wrzenia, a następnie ochładza, po czym odsącza. Surowy produkt przekrystalizowuje się z etanolu, otrzymując żółto-beżowy, krystaliczny produkt, z wydajnością 76% wydajności teoretycznej, o temperaturze topnienia 159-161 C.A 3 mmol sample of 5-amino-3-methylisoxazole-4-carboxylic acid methylhydrazide was placed in a 100 mL round-bottomed flask equipped with a reflux condenser and a stirrer bar. 50 mL of ethanol and 10 mL of triethyl orthoformate were added. After the mixture reached boiling point, 5 drops of concentrated hydrochloric acid were added. The mixture was stirred on a magnetic stirrer and heated at reflux for 10 minutes. As the reaction progressed, the mixture became clear. After completion of the reaction, as monitored by TLC plates, the solution was concentrated under reduced pressure to dryness. 50 mL of tetrahydrofuran (THF) was added to the residue and heated to boiling, then cooled and filtered. The crude product was recrystallized from ethanol to obtain a yellow-beige crystalline product with a yield of 76% of theory, melting point 159-161 C.
Tożsamość nowego związku udowodniono na drodze analizy instrumentalnej i spektralnej w sposób następujący:The identity of the new compound was proven by instrumental and spectral analysis as follows:
Temperatury topnienia oznaczono na aparacie Boethiusa i nie korygowano.Melting points were determined on the Boethius apparatus and are uncorrected.
Widma IR mierzono w KBr na aparacie Specord M-80.IR spectra were measured in KBr on a Specord M-80 instrument.
Widma 1H NMR oznaczono na aparacie Tesla 80 MHz. Przesunięcia chemiczne oznaczono wobec tetrametylosilanu (TMS) jako zewnętrznego standardu.1H NMR spectra were determined on an 80 MHz Tesla instrument. Chemical shifts were determined against tetramethylsilane (TMS) as an external standard.
Widma MS mierzono na spektrometrze LKB 9000.MS spectra were measured on an LKB 9000 spectrometer.
Wszystkie związki analizowano na zawartość (%) C, H, N. Różnice pomiędzy wartościami, obliczoną i znalezioną, nie przekraczały ± 0,3%. Wartości wyznaczone są następujące:All compounds were analyzed for the content (%) of C, H, and N. The differences between the calculated and found values did not exceed ±0.3%. The determined values are as follows:
IR (KBr)vc=ocm1 1667 1H NMR(DMSO-d6)/TMS d, J (Hz): 2,36 (s, 3H, CH3); 2,46 (s, 3H, CH3); 7,75 (s, H, XCH); 10,2 (s, H, NH) IR ( KBr ) 2 , 46 (p, 3H, CH 3 ); 7 , 75 (s, H, XCH ); 10 , 2 (s, H, NH)
MS (70 eV), m/z (%) 220,0.MS (70 eV), m/z (%) 220.0.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL343181A PL193279B1 (en) | 2000-10-11 | 2000-10-11 | Novel leading structure of isoxazolotriazepinone derivative and method of obtaining same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL343181A PL193279B1 (en) | 2000-10-11 | 2000-10-11 | Novel leading structure of isoxazolotriazepinone derivative and method of obtaining same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL343181A1 PL343181A1 (en) | 2002-04-22 |
| PL193279B1 true PL193279B1 (en) | 2007-01-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL343181A PL193279B1 (en) | 2000-10-11 | 2000-10-11 | Novel leading structure of isoxazolotriazepinone derivative and method of obtaining same |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL193279B1 (en) |
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- 2000-10-11 PL PL343181A patent/PL193279B1/en not_active IP Right Cessation
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| Publication number | Publication date |
|---|---|
| PL343181A1 (en) | 2002-04-22 |
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Legal Events
| Date | Code | Title | Description |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20081011 |