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Diene tetrazole aniline compound, its preparation method and use

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

Active Publication Date: 2016-03-30
肇庆市科至自动化设备有限公司
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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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  • Diene tetrazole aniline compound, its preparation method and use
  • Diene tetrazole aniline compound, its preparation method and use
  • Diene tetrazole aniline compound, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Take a 100mL round bottom flask, add 2.16g (10mmol) of compound II-1, dissolve it with 20mL of dry THF, stir under ice-water bath cooling, add 0.44g (20mmol) LiBH in batches 4 After that, continue to stir overnight at room temperature. TLC showed that the reaction was complete. The reaction mixture was poured into ice water, stirred, adjusted to pH=3 with concentrated hydrochloric acid, extracted with 50 mL×3 dichloromethane, combined the extracted organic phases, washed with saturated brine, dried with anhydrous sodium sulfate, and evaporated on a rotary evaporator The solvent was removed, and the obtained residue was purified by column chromatography to obtain the product III-1, a white solid, ESI-MS, m / z=175([M+H] + ).

[0027] Take a 100mL round bottom flask, add 1.39g (8mmol) compound III-1 and 10mL dichloromethane, stir under ice-water bath cooling, slowly add 5.41g (20mmol) PPBr 3 . After the addition, the reaction mixture was stirred at room temperature f...

Embodiment 2-6

[0030] According to the method of Example 1, the following compounds with general formula I were synthesized.

[0031]

[0032]

Embodiment 7

[0033] Example 7 In vitro platelet aggregation inhibition test

[0034] In a 96-well plate, the pharmacological test of the substance is performed in platelet aggregation induced by TRAP (thrombin receptor activating peptide). 3.13% sodium citrate solution was added to the syringe in advance, and then 20mL of healthy volunteers’ blood was drawn, centrifuged at 1500g for 20 minutes, the platelet-rich plasma (PRP) was separated and used 1μLPGE1 solution (500μg / mL ethanol Solution) / mLPRP. After incubating for 5 minutes at room temperature, it was centrifuged at 1200 g for 20 minutes to remove leukocytes. The white blood cell-free PRP was transferred to 15 mL PP tubes in batches of 5 mL / portion, and centrifuged at 3600 g to precipitate platelets. Then, the upper plasma was decanted, and the platelet pellet obtained from 5mLPRP was resuspended in 1mlLTyrode (120mMNaCl, 2.6mMKCl, 12mMNaHCO 3 , 0.39mMNaH 2 PO 4 , 10mMHEPES, 0.35% BSA, 5.5mM glucose, pH=7.4), and use Tyrode to adjust t...

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PUM

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Abstract

The invention relates to the field of medicine related to thrombotic diseases, in particular to a PAR-1 antagonist containing a diene tetrazole aniline structure and a preparation method and usage of the PAR-1 antagonist. According to the structural formula of the PAR-1 antagonist, R1 is selected from H, C1-C5 alkyl bases and C3-C5 naphthenic bases.

Description

Technical field [0001] The invention relates to the field of medicines related to thrombotic diseases. Specifically, the present invention relates to a class of PAR-1 antagonists containing a dienetetrazole aniline structure having a therapeutic effect on thrombotic diseases, and a preparation method thereof, a pharmaceutical composition containing them, and a therapeutic effect on thrombotic diseases use. Background technique [0002] Protease Activated Acceptor-1 (PAR-1) is a new target of antiplatelet antithrombotic drugs discovered recently. Protease activated receptor 1 is also called thrombin receptor. Thrombin is activated by the coagulation chain and acts on platelets through PAR-1 receptor to activate platelets, causing platelet aggregation to cause thrombus and coagulation. Thrombus caused by PAR-1 is rich in platelet components, which is the main cause of arterial thrombosis. PAR-1 antagonists can block thrombin from activating platelets, thereby blocking arterial t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D257/04A61P7/02
CPCC07D257/04
Inventor 蔡子洋
Owner 肇庆市科至自动化设备有限公司
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