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imidazopyridinecarboyl-k(k)-aa 1 -aa 2 -aa 3 -ak, its synthesis, activity and application

A technology of imidazopyridine, aa1-aa2-aa3-ala-lys, applied in imidazopyridineformyl-K(K)-AA1-AA2-AA3-AK, its synthesis, activity and application fields, can solve the problem of Issues such as effective drugs

Active Publication Date: 2020-01-14
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the clinical treatment of ischemic stroke faces the reality that there are no effective drugs, especially for patients with strokes lasting more than 4 hours, either dying or being disabled

Method used

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  • imidazopyridinecarboyl-k(k)-aa <sub>1</sub> -aa <sub>2</sub> -aa <sub>3</sub> -ak, its synthesis, activity and application
  • imidazopyridinecarboyl-k(k)-aa <sub>1</sub> -aa <sub>2</sub> -aa <sub>3</sub> -ak, its synthesis, activity and application
  • imidazopyridinecarboyl-k(k)-aa <sub>1</sub> -aa <sub>2</sub> -aa <sub>3</sub> -ak, its synthesis, activity and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Preparation of (6s)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (1)

[0068] Dissolve 10g (64.5mmol) L-His in 80mL distilled water and 20mL formaldehyde mixed solution, then add 1mL concentrated H 2 SO 4 , microwave reaction at 60°C for 5 hours, cooled to room temperature, and concentrated ammonia water was added dropwise to the reaction compound in an ice bath to adjust the pH to 7, and a large amount of precipitates precipitated out. Filtration afforded 10.5 g (97%) of the title compound as a colorless solid.

[0069] ESI-MS(m / z)167[M+H] + .

Embodiment 2

[0070] Example 2 Preparation of (6s)-3,5-di-Boc-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (2)

[0071] 1.67 g (10 mmol) of (6s)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid were dissolved in 5 ml of 2N aqueous sodium hydroxide solution under an ice bath. Add 5.23g (24mmol) (Boc) to the reaction solution 2 O with 10 mL of dioxane. Stirring at room temperature, TLC (CH 2 Cl 2 :MeOH=15:1) to monitor the disappearance of the reaction starting material point. After the reaction was completed, it was filtered, and the filtrate was concentrated under reduced pressure to remove dioxane. The remaining aqueous layer was washed with saturated KHSO 4 Acidify the aqueous solution to a pH value of 2, extract three times with ethyl acetate, combine the ethyl acetate layers, and backwash with a small amount of water, and wash the ethyl acetate layer with anhydrous Na 2 SO 4 Dry, filter, and concentrate under reduced pressure to obtain a pale yello...

Embodiment 3

[0072] Example 3 Preparation of (6s)-3,5-di-Boc-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-formyl-Lys-(Boc) -OBzl(3)

[0073] 3.67g (10.0mmol) (6s)-3,5-di-Boc-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxyl under ice bath and stirring Acid, 1.48g (11.0mmol) HOBt and 2.47g (12.0mmol) DCC were dissolved in 50ml anhydrous THF, and the reaction solution was activated for 30 minutes. Then, a suspension of 3.91 g (10.5 mmol) Tos·Lys(Boc)-OBzl and 50 mL of anhydrous THF adjusted to pH 9 with 1.0 mL of NMM was added dropwise to the activated reaction liquid. The ice bath was removed, stirred at room temperature for 12 hours, and dicyclohexylurea (DCU) was filtered off. The filtrate was concentrated to dryness under reduced pressure, the residue was dissolved in ethyl acetate, and DCU was filtered off. The filtrate layer was sequentially washed with saturated NaHCO 3 solution washed 3 times, saturated NaCl solution washed 3 times, saturated KHSO 4 solution washed 3 tim...

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Abstract

The invention discloses an imidazole-pyridine-formyl-K(K)-AA1-AA2-AA3-AK of formula I, their preparation methods, their antithrombotic activity, their thrombolytic activity, their effect on treating stroke rats and their applications in preparing antithrombotic drugs, thrombolysis drugs and ischemic stroke drugs.

Description

technical field [0001] The present invention relates to 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-formyl-Lys(Lys)-AA of formula I 1 -AA 2 -AA 3 -Ala-Lys, relate to their preparation method, relate to their antithrombotic activity, relate to their thrombolytic activity and relate to their effect of treating ischemic stroke, thus the present invention relates to their preparation antithrombotic drug, thrombolytic drug and Drug use in ischemic stroke. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Ischemic stroke is a relatively common and serious cerebrovascular disease, characterized by high incidence, high mortality, high disability rate and high recurrence rate. At present, the clinical treatment of ischemic stroke faces the reality that there is no effective drug, especially for patients with stroke lasting more than 4 hours, either dying or being disabled. It is an important clinical need to invent drugs that are eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K5/117C07K1/10C07K1/06A61P7/02A61P9/10
CPCY02P20/55
Inventor 彭师奇赵明王玉记吴建辉曹晔
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES