Compound of methyl triazole Schiff base structure, and preparation method and applications of compound

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

Inactive Publication Date: 2014-11-12
任占勇
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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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  • Compound of methyl triazole Schiff base structure, and preparation method and applications of compound
  • Compound of methyl triazole Schiff base structure, and preparation method and applications of compound
  • Compound of methyl triazole Schiff base structure, and preparation method and applications of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] .

[0032] Reaction raw materials: self-made, conventional method.

[0033] 1.20 g (10 mmol) compound II and 1.30 g (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 = 247 ([M+H] + ).

[0034] 1.24 g (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.

[0035] 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 ...

Embodiment 2-8

[0038] Referring to the method of Example 1, it is possible to synthesize I of the following compounds:

[0039]

[0040] .

Embodiment 9

[0041] Example 9 In vitro Platelet Aggregation Inhibition Test

[0042] compound Inhibition of Platelet Aggregation IC50 (nM) Compound of Example 1 2.2 Compound of Example 2 2.9 Compound of Example 3 3.7 Compound of Example 4 1.6 Compound of Example 5 2.7 Compound of Example 6 3.5 Compound of Example 7 4.2 Compound of Example 8 5.9

[0043] It can be seen from the above table that the compound of the present invention exhibits obvious inhibitory effect in the platelet aggregation test.

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PUM

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Abstract

The invention relates to the field of medicines related to thrombotic diseases, belongs to a triazole Schiff base compound of a brand new framework and derivatives of the triazole Schiff base compound, and particularly relates to a methyl-substituted PAR-1 antagonist of a triazole Schiff base structure, a preparation method of the PAR-1 antagonist, medicine combinations containing the PAR-1 antagonist and applications of the medicine combinations to preparation of medicines for treating thrombotic diseases. A general formula is shown in the specification, wherein definitions of substitutes are shown 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 with a methyltriazole Schiff base structure that has 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 t...

Claims

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Application Information

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IPC IPC(8): C07D249/12A61K31/5377A61P7/02
CPCC07D249/12
Inventor 张远强
Owner 任占勇
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