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Compound with aniline and diene fluoro adamantane structure and preparation method and application thereof

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

Active Publication Date: 2015-04-22
邳州市润宏实业有限公司
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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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  • Compound with aniline and diene fluoro adamantane structure and preparation method and application thereof
  • Compound with aniline and diene fluoro adamantane structure and preparation method and application thereof
  • Compound with aniline and diene fluoro adamantane structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] 2.46g (10mmol) compound II and 2.62g (10mmol) PPh 3 Dissolve in 20 mL of dry THF and reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, a white cloudy solution was obtained. Cooled to -78°C under nitrogen protection, slowly added 6.25mL (10mmol, 1.6M) n-BuLi n-hexane solution dropwise. After the dropwise addition was completed, stirring was continued for one hour, and a solution prepared by dissolving compound 1.28g (10mmol) III in 2mL of THF was added dropwise. After the dropwise addition was complete, the reaction mixture was slowly warmed to room temperature and then refluxed for 1 hour. The reaction mixture was poured into ice water, stirred, extracted with 50 mL×3 dichloromethane, the combined extracts were washed with brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, 0.50 g of iodine was added to the filtrate, and stirred overnight at room temperature....

Embodiment 2-4

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

[0034]

Embodiment 5

[0035] The preparation of embodiment 5 reference compound D1

[0036] In order to fully illustrate the beneficial effects of the compounds of the present invention, the applicant recorded the following compound D1 (unpublished) found during the experiment as a pharmacodynamic reference compound.

[0037]

[0038] The synthesis method is as follows:

[0039]

[0040] 2.47g (10mmol) compound II and 2.62g (10mmol) PPh 3 Dissolve in 20 mL of dry THF and reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, a white cloudy solution was obtained. Cooled to -78°C under nitrogen protection, slowly added 6.25mL (10mmol, 1.6M) n-BuLi n-hexane solution dropwise. After the dropwise addition was completed, stirring was continued for one hour, and a solution prepared by dissolving compound 1.28g (10mmol) III in 2mL of THF was added dropwise. After the dropwise addition was complete, the reaction mixture was slowly warmed to room temp...

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PUM

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Abstract

The invention relates to the field of drugs relevant to thrombotic diseases, in particular to a PAR-1 antagonist with an aniline and diene fluoro adamantane structure, a preparation method of the PAR-1 antagonist and the application of the PAR-1 antagonist. The structural general formula of the PAR-1 antagonist is specified in the specification, wherein R1 and R2 are selected from alkyl groups of H and C1-C5 respectively.

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 aniline and dienyl fluoroadamantane structures that have a therapeutic effect on thrombotic diseases, and their preparation methods, pharmaceutical compositions containing them and in the treatment of thrombotic diseases. Disease use. 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 Applications(China)
IPC IPC(8): C07D207/335A61K31/4015A61P7/02A61P9/10
CPCC07D207/335
Inventor 蔡子洋
Owner 邳州市润宏实业有限公司
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