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Compounds with terminally-disubstituted triazole Schiff base structure as well as preparation methods and applications of compounds

The technology of a compound and general formula is applied in the fields of triazole Schiff base compounds and their derivatives, PAR-1 antagonists with triazole Schiff base structure and their preparation, which can solve the problems of high bleeding risk and other problems

Active Publication Date: 2014-10-08
JIANGSU BAIJIAN PHARMA TECH CO LTD
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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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  • Compounds with terminally-disubstituted triazole Schiff base structure as well as preparation methods and applications of compounds
  • Compounds with terminally-disubstituted triazole Schiff base structure as well as preparation methods and applications of compounds
  • Compounds with terminally-disubstituted triazole Schiff base structure as well as preparation methods and applications of compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] .

[0033] Reaction raw materials: self-made, conventional method.

[0034] 1.66 g (10 mmol) compound II and 1.16g (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 = 265 ([M+H] + ).

[0035] 1.33 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. The reaction mixture was cooled slightly and poured into 200 mL of 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 an...

Embodiment 2-4

[0037] Referring to the method of Example 1, it is possible to synthesize I of the following compounds:

[0038]

Embodiment 5

[0039] Example 5 In vitro platelet aggregation inhibition test

[0040] compound Inhibition of Platelet Aggregation IC50 (nM) Compound I-1 1.7 Compound I-2 3.9 Compound I-3 5.1 Compound I-4 3.7

[0041] 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 thrombotic disease related drugs, belongs to triazole Schiff base compounds with brand new structures and derivatives of the triazole Schiff base compounds and particularly relates to PAR (Protease Activated Receptor)-1 antagonists with terminally-disubstituted triazole Schiff base structures, preparation methods of the PAR-1 antagonists, pharmaceutical compositions containing the PAR-1 antagonists and applications of the PAR-1 antagonists to preparation of drugs for treating thrombotic diseases. All the substituent groups are defined as 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, in particular, it relates to a class of PAR-1 antagonistic triazole Schiff base structures with terminal double substitutions that have a therapeutic effect on thrombotic diseases Agents and their preparation methods, 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....

Claims

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Application Information

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IPC IPC(8): C07D249/12A61P7/02
CPCC07D249/12
Inventor 张远强
Owner JIANGSU BAIJIAN PHARMA TECH CO LTD
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