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Warfarin-4-o-acetyl-yigsk, its synthesis, pharmacological activity and application

A technology of warfarin and acetyl, applied in the field of application of factor II antagonists

Inactive Publication Date: 2021-03-30
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Warfarin-4-o-acetyl-yigsk, its synthesis, pharmacological activity and application
  • Warfarin-4-o-acetyl-yigsk, its synthesis, pharmacological activity and application
  • Warfarin-4-o-acetyl-yigsk, its synthesis, pharmacological activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Preparation of warfarin-4-O-benzyl acetate

[0024] Put 3.31g (10.00mmol) of warfarin in a 100mL eggplant bottle, add about 40mL of acetone, but it cannot be completely dissolved, heat and stir in an oil bath at 45°C until the warfarin dissolves, add 1.73mL (11.00mmol) of bromine- 2-Benzyl acetate, continue to react in an oil bath at 45°C, and after about 1 hour, a white solid is found attached to the bottle wall. After 48 hours of reaction, the reaction progress was monitored by thin layer chromatography (TLC, petroleum ether / ethyl acetate=2:1), warfarin disappeared, and the colorless solid produced in the reaction was filtered off, and acetone was removed under reduced pressure to obtain a light yellow oil The product was purified by silica gel column chromatography (petroleum ether / ethyl acetate=8:1) to obtain 3.02 g (65%) of the title compound as a colorless solid. ESI-MS(m / e):457[M+H] + ; 1 H-NMR (300MHz, DMSO-d 6 )δ / ppm=7.89(dd,J 1 =3.0Hz,J 2 =9.0H...

Embodiment 2

[0025] Example 2 Preparation of warfarin-4-O-acetic acid

[0026] Dissolve 2.26g (4.95mmol) of warfarin-4-O-benzyl acetate in 20mL of methanol, add 220mg of palladium carbon (Pd / C), under stirring, pump out the air in the water pump, and pass in hydrogen, and repeat the operation Carry out 3 times, and stir at room temperature for 10 h by introducing hydrogen gas. The completion of the reaction was monitored by TLC, Pd / C was removed by filtration, the filtrate was concentrated under reduced pressure to remove the solvent, the residue was solidified with petroleum ether, and washed with anhydrous ether to obtain 1.72 g (93%) of the title compound as a colorless solid. ESI-MS(m / e):367[M+H] + ; 1 H-NMR (300MHz, DMSO-d 6 ):δ / ppm=12.86(s,1H),7.90(d,J=6.0Hz,1H),7.63(t,J=6.0Hz,1H),7.43~7.34(m,4H),7.27(t, J=9.0Hz, 2H), 7.17(t, J=9.0Hz, 1H), 4.99(t, J=9.0Hz, 1H), 4.75(q, J 1 =15.0Hz,J 2 =30.0Hz, 2H), 3.54~3.47(m, 2H), 2.14(s, 3H).

Embodiment 3

[0027] Example 3 Preparation of Boc-Ile-Gly-OBzl

[0028]Add 2.00g (8.65mmol) Boc-Ile into a 250mL eggplant bottle and dissolve it with 50mL anhydrous tetrahydrofuran, add 1.17g (8.66mmol) HOBt and 1.78g (8.69mmol) DCC in an ice bath (0°C), Activation for 30min. A large amount of DCU was precipitated. Dissolve 1.75g ​​(8.69mmol) of HCl Gly-OBzl in 50mL of anhydrous tetrahydrofuran, add it to the reaction solution under ice-cooling, adjust the pH value to 8-9 with N-methylmorpholine (NMM), and After stirring the reaction at room temperature for 4 h, TLC (dichloromethane / methanol=35:1) monitored the reaction progress, the raw material point disappeared, filtered off DCU, and the filtrate was decompressed to remove the solvent, the residue was dissolved in 100 mL of ethyl acetate, and the insoluble DCU, the filtrate was saturated Na 2 CO 3 solution (40mL×3), saturated NaCl solution (40mL×3), saturated KHSO 4 solution (40mL×3), saturated NaCl solution (40mL×3), saturated NaCl...

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Abstract

The present invention discloses warfarin-4-O-acetyl-Tyr-Ile-Gly-Ser-Lys, a preparation method, anti-arterial thrombus activity, anti-venous thrombosis activity, in vivo vitamin K content lowering activity, in vivo blood coagulation factor II content lowering activity, and platelet aggregation inhibition activity thereof, such that the invention discloses applications of warfarin-4-O-acetyl-Tyr-Ile-Gly-Ser-Lys in preparation of anti-arterial thrombus drugs, anti-venous thrombosis drugs, platelet aggregation inhibition drugs, vitamin K antagonists, and blood coagulation factor II antagonists.

Description

technical field [0001] The present invention relates to warfarin-4-O-acetyl-Tyr-Ile-Gly-Ser-Lys, to its preparation method, to its anti-arterial thrombosis activity, to their anti-venous thrombosis activity, to its reduction of vitamin The role of K content involves its function of reducing the content of coagulation factor II in the body, and its function of inhibiting platelet aggregation. Thus the present invention relates to its application in the preparation of anti-arterial thrombosis drugs, its application in the preparation of anti-venous thrombosis drugs, its application in the preparation of platelet aggregation inhibiting drugs, its application in the preparation of vitamin K antagonists and its use in the preparation of coagulation factor II Antagonist applications. The invention belongs to the field of biomedicine. Background technique [0002] Both arterial thrombosis and venous thrombosis have become diseases with high morbidity and mortality. Among them, v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/02A61K31/37A61K47/64A61P7/02
CPCA61K38/00C07K7/06
Inventor 彭师奇赵明吴建辉王玉记张薪
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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