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Alkoxyphenyl-substituted trans-cyclohexane amides and uses

A technology of compounds and uses, applied in the field of drugs related to thrombosis diseases, can solve problems such as high bleeding risk

Inactive Publication Date: 2016-07-06
ZHEJIANG PHARMA COLLEGE
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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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  • Alkoxyphenyl-substituted trans-cyclohexane amides and uses
  • Alkoxyphenyl-substituted trans-cyclohexane amides and uses
  • Alkoxyphenyl-substituted trans-cyclohexane amides and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of Compound I-1

[0026]

[0027] Raw materials: commercially available or homemade.

[0028] In a 100mL round bottom flask, add 1.84g (10mmol) of compound II and 10mL of re-distilled SOCl 2 , And then heated to reflux with stirring for 3 hours.

[0029] The reaction mixture was distilled out of excess SOCl under reduced pressure 2 The residue II-C was dissolved in 20 mL of dry dichloromethane, the resulting mixture was stirred under cooling in an ice-water bath, and then 1.92 g (10 mmol) III-1 and 3.04 g (30 mmol) triethylamine were dissolved in 5 mL dry. The solution made of dichloromethane was continued to stir overnight at room temperature. TLC showed that the reaction was complete.

[0030] The reaction mixture was poured into ice water, stirred, and extracted with 50 mL×3 dichloromethane. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a rotary evaporator to obtain...

Embodiment 2-12

[0032] With reference to the methods of Examples 1 and 2, the following compounds with general formula I were synthesized.

[0033]

Embodiment 7

[0034] Example 7 In vitro platelet aggregation inhibition test

[0035] In a 96-well plate, the pharmacological test of the substance was performed in the platelet aggregation induced by TRAP (thrombin receptor activating peptide). 3.13% sodium citrate solution was added to the syringe in advance, and then 20mL of healthy volunteers’ blood was drawn, centrifuged at 1500g for 20 minutes, the platelet-rich plasma (PRP) was separated and used 1μLPGEl solution (500μg / mL ethanol Solution) / mLPRP. After incubating for 5 minutes at room temperature, it was centrifuged at 1200 g for 20 minutes to remove leukocytes. The white blood cell-free PRP was transferred to 15 mL PP tubes in batches of 5 mL / portion, and centrifuged at 3600 g to precipitate platelets. Then, the upper plasma was decanted, and the platelet pellet obtained from 5mLPRP was resuspended in 1mlLTyrode (120mMNaCl, 2.6mMKCl, 12mMNaHCO 3 , 0.39mMNaH 2 PO 4 , 10mMHEPES, 0.35% BSA, 5.5mM glucose, pH=7.4), and use Tyrode to adj...

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PUM

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Abstract

The invention relates to the field of thrombotic disease related medicines. Specifically, the invention relates to a terminal alkoxy phenyl substituted trans-cyclohexane amide structured PAR-1 antagonist, a preparation method thereof and application of the antagonist in preparation of medicines for treating thrombotic diseases, wherein R is selected from C1-C3 alkyl and C3-C5 cycloalkyl.

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 terminal alkoxyphenyl substituted trans-cyclohexane amide structure PAR-1 antagonists and preparation methods thereof, pharmaceutical compositions containing them and Use in medicine. 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 receptor to activate platelets, causing platelet aggregation to cause thrombosis and coagulation. Thrombus 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 arterial thrombosis, and can be used to treat acute coronary artery disea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185A61P7/02
CPCC07D295/185
Inventor 郭章华
Owner ZHEJIANG PHARMA COLLEGE
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