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Compound containing aniline and diene 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: 2015-03-25
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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  • Compound containing aniline and diene adamantane structure and preparation method and application thereof
  • Compound containing aniline and diene adamantane structure and preparation method and application thereof
  • Compound containing aniline and diene adamantane structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] 2.43g (10mmol) compound II and 2.62g (10mmol) PPh 3 Dissolve in 20mL dry THF, reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, a white turbid solution was obtained. Under the protection of nitrogen, it was cooled to -78°C, and 6.25 mL (10 mmol, 1.6M) n-BuLi in n-hexane was slowly added dropwise. After the addition is complete, continue to stir for one hour, and then add dropwise a solution of compound 1.28g (10mmol) III dissolved in 2mL THF. After the addition was completed, the reaction mixture was slowly warmed to room temperature, and then refluxed for 1 hour. The reaction mixture was poured into ice water, stirred, and 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 the mixture was stirred overnight at room temperature. The react...

Embodiment 2-4

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

[0031]

[0032]

Embodiment 5

[0033] Example 5 Preparation of reference compound D1

[0034] In order to fully illustrate the beneficial effects of the compounds of the present invention, the applicant recorded the compound D1 (unpublished) found during the experiment as a reference compound for pharmacodynamics.

[0035]

[0036] The synthesis method is as follows:

[0037]

[0038] 2.43g (10mmol) compound II and 2.62g (10mmol) PPh 3 Dissolve in 20mL dry THF, reflux overnight under nitrogen protection. After the reaction mixture was cooled to room temperature, a white turbid solution was obtained. Under the protection of nitrogen, it was cooled to -78°C, and 6.25 mL (10 mmol, 1.6M) n-BuLi in n-hexane was slowly added dropwise. After the addition is complete, continue to stir for one hour, and then add dropwise a solution of compound 1.28g (10mmol) III dissolved in 2mL THF. After the addition was completed, the reaction mixture was slowly warmed to room temperature, and then refluxed for 1 hour. The reaction ...

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PUM

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Abstract

The invention relates to the field of medicine relevant to thrombotic diseases, in particular to a PAR-1 antagonist containing an anilino group and a diene adamantane structure and a preparation method and application of the PAR-1 antagonist. According to the general formula (please see the specification), R<1> and R<2> are selected from an alkyl group of H and an alkyl group of C1-C5 respectively.

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 anilino and diene adamantane structures that have a therapeutic effect on thrombotic diseases, and a preparation method thereof, a pharmaceutical composition containing them, and the treatment of thrombotic diseases the use of. 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 receptors to activate platelets, causing platelet aggregation to cause thrombus and coagulation. Thrombosis 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/335A61K31/402A61P7/02A61P9/10
CPCC07D207/335
Inventor 蔡子洋
Owner HONGGUAN BIO PHARMA CO LTD
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