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Phenyl triazole schiff base compound as well as preparation method and application thereof

A compound and alkyl technology, applied in the field of drugs related to thrombosis diseases, can solve problems such as high bleeding risk

Active Publication Date: 2014-10-15
南京药诚医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of these drugs is the greater risk of bleeding

Method used

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  • Phenyl triazole schiff base compound as well as preparation method and application thereof
  • Phenyl triazole schiff base compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] . Reaction raw materials: self-made, conventional method.

[0032] 1.66 g (10 mmol) compound II and 1.92g (10 mmol) of compound III-1 Dissolve in 20 mL of glacial acetic acid and heat to reflux overnight. After the reaction mixture was slightly cooled, it was poured into 200 mL of ice water, stirred, and the solid was collected by suction filtration, recrystallized from absolute ethanol, and vacuum-dried at room temperature to obtain the product IV-1 , white crystals. MS, m / z = 341([M+H] + ).

[0033] 1.70g (5 mmol) compound IV-1 , 1.85 g (5 mmol) compound V and 2.07 g (15 mmol) of solid potassium carbonate were stirred overnight in 15 mL of acetonitrile, and then heated to reflux for 3 hours. The reaction mixture was cooled slightly and poured into 200 mL ice water, stirred, adjusted to pH = 4 with concentrated hydrochloric acid, extracted with 50 mL × 3 dichloromethane, combined organic phases, washed with brine, dried over anhydrous sodium sul...

Embodiment 2-4

[0035] Referring to the method of Example 1, it is possible to synthesize I of the following compounds:

[0036] .

Embodiment 5

[0037] Example 5 In vitro platelet aggregation inhibition test

[0038] Pharmacological tests of substances were performed in TRAP (thrombin receptor activating peptide)-induced platelet aggregation in 96-well plates. 3.13% sodium citrate solution was pre-added in the syringe, and then 20 mL of blood from healthy volunteers was drawn in, at 1500 gPlatelet-rich plasma (PRP) was separated by centrifugation for 20 minutes and treated with 1 μL PGE1 solution (500 μg / mL in ethanol) / mL PRP. After incubation at room temperature for 5 minutes, they were centrifuged at 1200 g for 20 minutes to remove leukocytes. Transfer the leukocyte-free PRP to 15 mL PP tubes in batches at 5 mL / portion, and centrifuge at 3600 g to pellet the platelets. Then, decant the upper plasma layer and resuspend the platelet pellet from 5 mL PRP in 1 mL Tyrode (120 mM NaCl, 2.6 mM KCl, 12 mM NaHCO3, 0.39 mM NaH2PO4, 10 mM HEPES, 0.35% BSA, 5.5 mM Glucose, pH = 7.4) and adjusted to a platelet count of 3 × 1...

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PUM

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Abstract

The invention relates to the field of drugs related to thrombotic diseases. Specifically, the invention belongs to a triazole schiff base compound with a novel skeleton and a derivative thereof and particularly relates to a PAR-1 antagonist adopting the structure of the phenyl triazole schiff base, a preparation method for the PAR-1 antagonist, a pharmaceutical composition containing the PAR-1 antagonist and the application of the pharmaceutical composition in preparing drugs for treating thrombotic diseases; in the formula (I) (as shown in the specification), each replaced definition is as described in the specification.

Description

technical field [0001] The invention relates to the field of drugs related to thrombosis diseases. The present invention belongs to a class of triazole Schiff base compounds and their derivatives with a new skeleton, and specifically relates to a class of PAR-1 antagonists of phenyl triazole Schiff bases that have a therapeutic effect on thrombotic diseases and Preparation methods thereof, and pharmaceutical compositions containing them. Background technique [0002] Protease Activated Acceptor-1 (PAR-1) is a new target of anti-platelet antithrombotic drugs discovered recently. Protease-activated receptor 1 is also called thrombin receptor. After thrombin is activated by the coagulation chain, it acts on platelets through PAR-1 receptors to activate platelets, causing platelet aggregation and causing thrombus and coagulation. The thrombus induced by PAR-1 is rich in platelet components, which is the main cause of arterial thrombus. PAR-1 antagonists can block thrombin fro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12A61K31/5377A61P7/02
CPCC07D249/12
Inventor 张远强
Owner 南京药诚医药科技有限公司
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