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Nitrile-grouping benzene diene tetrazole compound and preparation method and application thereof

A compound, alkyl 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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  • Nitrile-grouping benzene diene tetrazole compound and preparation method and application thereof
  • Nitrile-grouping benzene diene tetrazole compound and preparation method and application thereof
  • Nitrile-grouping benzene diene tetrazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Take a 100mL round bottom flask, add 2.27g (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=186 ([M+H] + ).

[0025] Take a 100mL round bottom flask, add 1.48g (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

[0028]

[0029] Take a 100mL round bottom flask, add 2.27g (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=186 ([M+H] + ).

[0030] Take a 100mL round bottom flask, add 1.48g (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 3-8

[0033] According to the method of Example 1, the following compounds with general formula I were synthesized.

[0034]

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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 nitrile-grouping benzene diene tetrazole structure and a preparation method and application of the antagonist. As shown in the description, R1 represents an alkyl group of H, C1-C3 and a naphthenic base of C3-C5.

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 nitrile-phenylenediene 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. Uses above. 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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