Imidazo pyridine acyl-KRGDV, synthesis thereof, antithrombus activity and application

A technology of imidazopyridine and formyl, which is applied in the application field of antithrombotic drugs and can solve problems such as unsatisfactory antithrombotic activity

Active Publication Date: 2017-01-25
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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[0006] However, the inventors were not satisfied with

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  • Imidazo pyridine acyl-KRGDV, synthesis thereof, antithrombus activity and application
  • Imidazo pyridine acyl-KRGDV, synthesis thereof, antithrombus activity and application
  • Imidazo pyridine acyl-KRGDV, synthesis thereof, antithrombus activity and application

Examples

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Embodiment 1

[0027] Example 1 Preparation of 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (1)

[0028] Slowly add 0.8mL H 2 SO 4 , to dissolve completely. To this solution was added 6 mL of 40% aqueous formaldehyde. The ice bath was removed, and the reaction was carried out at 60° C. for 8 h. TLC (ethyl acetate: water: glacial acetic acid = 4:1:1) monitored the disappearance of the starting point. The reaction solution was cooled to room temperature, and the pH was adjusted to 6 with concentrated ammonia water in an ice bath, and a large amount of colorless solids were precipitated. filter. The filter residue was washed with water and acetone to afford 4.52 g (84%) of the title compound. ESI-MS(m / e): 168[M+H] + .

Embodiment 2

[0029] Example 2 Preparation of 3,5-di-Boc-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (2)

[0030] Add 40mL of 1,4 - 14.3 g (65.7 mmol) dissolved in dioxane (Boc) 2 O, adjust the pH to 8-9 with 4N NaOH solution, react at room temperature for 24 h, and monitor the disappearance of the raw material point by TLC (dichloromethane:methanol=15:1). The reaction solution was saturated KHSO 4 Adjust the pH of the solution to 7, evaporate 1,4-dioxane under reduced pressure, and then use saturated KHSO 4 The solution was adjusted to pH 2. It was extracted three times with ethyl acetate, and the ester layer was washed three times with saturated NaCl. Dry with anhydrous sodium sulfate for 30min and filter. The filtrate was evaporated to dryness under reduced pressure. Add a small amount of ethyl acetate to just dissolve it and let it stand. A solid precipitated and was filtered. Yield 1.2 g (11%) of the title compound as a colorless solid. ESI-MS(m / e): 368[M+H]...

Embodiment 3

[0031] Example 3 Preparation of 3,5-di-Boc-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-formyl-Lys(Boc)-OBzl(3)

[0032] 367mg (1mmol) of 3,5-di-Boc-4,5,6,7-anhydro-3H-imidazo[4,5-c]pyridine-6 ​​was dissolved in 20mL dry tetrahydrofuran (THF) under ice bath - Carboxylic acid dissolves. Add 142mg (1.05mmol) HOBt and 258mg (1.25mmol) DCC, stir and activate for 30min. Dissolve 558 mg (1.1 mmol) Tos·Lys(Boc)-OBzl in 10 mL of dry THF, adjust the pH to 8 with NMM, add the solution dropwise to the reaction solution, and finally adjust the pH of the reaction solution to 8 with NMM. After reacting at room temperature for 5 h, TLC (petroleum ether: acetone = 3:1) showed that the starting material disappeared. Dicyclohexylurea (DCU) was removed by filtration, the reaction solution was evaporated to dryness under reduced pressure, and the residue was dissolved in ethyl acetate, followed by saturated NaHCO 3 solution, saturated NaCl solution, 5% KHSO 4 solution, saturated NaCl soluti...

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Abstract

The invention discloses the following formula: 4, 5, 6, 7-tetralin-3H-imidazo [4, 5-c] pyridine-6-formyl-Lys-Arg-Gly-Asp-Val. The invention discloses a preparation method of the formula, the antithrombus activity of the formula, and application of the formula to antithrombus drugs.

Description

[0001] field of invention [0002] The present invention relates to 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-formyl-Lys-Arg-Gly-Asp-Val, to its preparation method, to their antithrombotic activity, and thus the present invention relates to its use as an antithrombotic drug. The invention belongs to the field of biomedicine. Background technique [0003] Coronary heart disease, stroke, and vasculitis are very common cardiovascular and cerebrovascular diseases. With the continuous improvement of people's living standards, the incidence of cardiovascular and cerebrovascular diseases is increasing year by year. Risk factors for cardiovascular and cerebrovascular diseases are prevalent, and the prevalence of cardiovascular and cerebrovascular diseases in my country continues to rise. According to statistics, 1 out of every 5 adults suffers from cardiovascular disease. Thrombosis is an important cause of cardiovascular and cerebrovascular diseases. Prevention of thrombosi...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/02A61K38/08A61P7/02
Inventor 赵明彭师奇吴建辉王玉记张凇
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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