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Warfarin-4-o-acetyl-ldv, its synthesis, activity and application

A technology of warfarin,-leu-asp-val, applied in warfarin-4-O-acetyl-LDV, its synthesis, activity and application field

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation Wafer Forest-4-O-Benzyl acetate

[0026] 3.31 g (10.00 mmol) of the Waylin Lin was placed in a 100ml of ketchprint, and about 40 ml of acetone was added, and it was not completely dissolved, and the oil bath was added to the gaw of the oil, and 1.73 ml (11.00 mmol) bromine was added. 2-benzyl acetate, continued to replace at 45 ° C oil bath, and the white solid was found to be attached to the wall after about 1 h. After 48 h, thin layer chromatography (TLC, petroleum ether / ethyl acetate = 2: 1) Monitor the reaction process, Hua Fi Lin disappeared, the reaction produced colorless solid was filtered, remove the acetone under reduced pressure, to obtain a light yellow oil Through silica gel column chromatography (petroleum ether / ethyl acetate = 8: 1), 3.02 g (65%) title compound was obtained 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 = 9.0Hz, 1H), 7.63 (DT, J 1 = 3.0Hz, J 2 = ...

Embodiment 2

[0027] 2.26 g (4.95 mmol) 华 法林 -4-O-acetate benzyl ester is dissolved in 20 mL of methanol, adding 220 mg of palladium carbon (PD / C), stirring to penetrate the air in the water pump, passing into hydrogen, and repeating Three times, stirring at a hydrogen room temperature for 10 h. The TLC was monitored, and PD / C was removed, and the filtrate was removed and the filtrate was concentrated to remove the solvent. The residue was solidified with petroleum ether, and washed with water to give 1.72 g (93%) title compound, which is 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 = 6.0 Hz, 1H), 7.63 (T, J = 6.0 Hz, 1H), 7.43 ~ 7.34 (M, 4H), 7.27 (T, J = 9.0Hz, 2H), 7.17 (T, J = 9.0 Hz, 1H), 4.99 (T, J = 9.0 Hz, 1H), 4.75 (Q, J 1 = 15.0 Hz, J 2 = 30.0Hz, 2H), 3.54 ~ 3.47 (m, 2H), 2.14 (s, 3h).

Embodiment 3

[0028] Example 3 Preparation Boc-ASP (Obzl) -Val-Obzl

[0029]10.21 g (31.61 mmol) of Boc-ASP (Obzl) was added to 500 ml of ketchprint, dissolved with 250 ml of anhydrous tetrahydrofuran, adding 4.18 g (30.97 mmol) HOBT and 7.65g (37.16) under ice bath (0 ° C). Mmol) DCC, activated 30 min. There is a large number of DCU precipitation. 11.73 g (30.94 mmol) TOS · VAL-OBZL was dissolved in 150 ml of anhydrous tetrahydrofuran, and it was added to the reaction solution under an ice bath, and the pH was adjusted with N-methyl morpholine (NMM) to 8 ~ 9, After stirring at room temperature for 6 h, TLC (dichloromethane / methanol = 30: 1) was monitored, and the material point disappeared, filtered off DCU, remove the solvent under reduced pressure, dissolved with 100 ml of ethyl acetate, filter it. DCU, filtrate separately with saturated NA 2 CO 3 Solution (40 ml × 3), saturated NaCl solution (40 ml × 3), saturated kHSO 4 Solution (40 ml × 3), saturated NaCl solution (40 ml × 3), saturated...

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Abstract

The invention discloses warfarin-4-O-acetyl-Leu-Asp-Val, a preparation method, anti-arterial thrombus activity, anti-venous thrombosis activity, in vivo platelet membrane glycoprotein IIb / IIIa (GPIIb / IIIa) content lowering 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-Leu-Asp-Val in preparation of anti-arterial thrombus drugs, anti-venous thrombosis drugs, platelet aggregation inhibition drugs, GPIIb / IIIa antagonists, vitamin K antagonists, and blood coagulation factor II antagonists.

Description

Technical field [0001] The present invention relates to warfarin-4-O-acetyl-deu-ASP-VAL, which relates to its preparation method involving its anti-pulse thrombin activity, involving their antiprotechnological activity, involving it to reduce GPIIB / IIIA in the body. The role involving it to reduce the content of vitamin K in the body, involving it to reduce the effect of intra-body coagulation factor II, involving it inhibiting the role of platelet aggregation. The present invention relates to the application of the preparation of the anti-arterial thrombus drug, in which the application inhibiting the use of platelet aggregation drugs is prepared in the preparation of the application of the HP IIIA antagonist in the preparation of the application of the Plate IIIA antagonist. Application in antagonists and applications in the preparation of coagulation factors II antagonists. The invention is within the field of biomedicine. Background technique [0002] The two conditions of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/083C07K1/02A61K38/06A61P7/02
CPCA61K38/00C07K5/0808
Inventor 彭师奇赵明吴建辉王玉记张薪
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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