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Diene tetrazole halobenzene series compound and preparation method and applications thereof

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

Active Publication Date: 2015-04-08
HONGGUAN BIO PHARMA 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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  • Diene tetrazole halobenzene series compound and preparation method and applications thereof
  • Diene tetrazole halobenzene series compound and preparation method and applications thereof
  • Diene tetrazole halobenzene series compound and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Take a 100mL round bottom flask, add 2.16g (10mmol) of compound II-1, dissolve in 20mL of dry THF, stir under ice-water bath cooling, add 0.44g (20mmol) LiBH in batches 4 Afterwards, stirring was continued overnight at room temperature. TLC showed 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 and extracted organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated on a rotary evaporator. The solvent was removed, and the obtained residue was purified by column chromatography to obtain product III-1, a white solid, ESI-MS, m / z=175 ([M+H] + ).

[0028] 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 was complete, the reaction mixture was stirred a...

Embodiment 2-10

[0031] Referring to the method of Example 1, the following compounds with general formula I were synthesized.

[0032]

[0033]

Embodiment 11

[0034] Example 11 In vitro platelet aggregation inhibition test

[0035] 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 added to the syringe in advance, and then 20 mL of blood from healthy volunteers was drawn in, centrifuged at 1500 g for 20 minutes, platelet-rich plasma (PRP) was separated and mixed with 1 μL of PGE1 solution (500 μg / mL ethanol solution) / mL PRP for treatment. 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 of PRP in 1 mL of Tyrode (120 mM NaCl, 2.6 mM KCl, 12 mM NaHCO 3 , 0.39mM NaH 2 PO 4 , 10 mM HEPES, 0.35% BSA, 5.5 mM glucose, pH=7.4), and ad...

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PUM

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Abstract

The invention relates to the field of drugs being relates to thrombotic diseases, in particular to PAR-1 (Protease Activated Acceptor-1) antagonist comprising a diene tetrazole halobenzene structure and a preparation method and applications thereof. A general formula is as the following, wherein R1 is selected from alkyl group of hydrogen and carbon 1 to carbon 5 and naphthenic base from carbon 3 to carbon 5; R2 is selected from halogen substituent.

Description

technical field [0001] The invention relates to the field of drugs related to thrombosis diseases. Specifically, the present invention relates to a class of PAR-1 antagonists containing a dienyl tetrazole halobenzene structure that has a therapeutic effect on thrombotic diseases, a preparation method thereof, a pharmaceutical composition containing them, and a therapeutic effect on thrombotic diseases. the use of. 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 from activating platelets, ...

Claims

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Application Information

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IPC IPC(8): C07D257/04A61P7/02
CPCC07D257/04
Inventor 蔡子洋
Owner HONGGUAN BIO PHARMA CO LTD
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