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Halogenated phenyldiene tetrazole compound, its preparation method and use

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

Active Publication Date: 2016-04-13
铜陵易难信息科技有限公司
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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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  • Halogenated phenyldiene tetrazole compound, its preparation method and use
  • Halogenated phenyldiene tetrazole compound, its preparation method and use
  • Halogenated phenyldiene tetrazole compound, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Take a 100mL round bottom flask, add 2.20g (10mmol) of compound II, 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, a white solid, ESI-MS, m / z=179 ([M+H] + ).

[0028] Take a 100mL round bottom flask, add 1.42g (8mmol) compound III 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 at room...

Embodiment 2-14

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

[0032]

[0033]

Embodiment 15

[0034] Example 15 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. Add 3.13% sodium citrate solution to the syringe in advance, then draw 20mL of blood from healthy volunteers, centrifuge at 1500g for 20 minutes, separate the platelet-rich plasma (PRP) and wash it with 1μL PGE1 solution (500μg / mL ethanol solution) / mLPRP 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 adjusted to a platelet count...

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PUM

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Abstract

The invention relates to the field of medicine correlated to thrombotic diseases, in particular to a PAR-1 antagonist with a halobenzene diene tetrazole structure and a preparation method and application thereof. As shown in the description, R1 represents an alkyl group of H, C1-C3 and a naphthenic base of C3-C5, and R2 represents a halogen substituted base.

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 halogenated benzenediene tetrazole structure that has a therapeutic effect on thrombotic diseases, a preparation method thereof, a pharmaceutical composition containing them and a method for treating 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 platelet...

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 铜陵易难信息科技有限公司
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