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Halogenated phenyl-containing trans-cyclohexane amide compound and application thereof

A compound and substituent technology, applied in the field of PAR-1 antagonists with trans-cyclohexane amide structure and their preparation, can solve the problems of high bleeding risk and the like

Inactive Publication Date: 2015-02-18
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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  • Halogenated phenyl-containing trans-cyclohexane amide compound and application thereof
  • Halogenated phenyl-containing trans-cyclohexane amide compound and application thereof
  • Halogenated phenyl-containing trans-cyclohexane amide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of Compound I-1

[0027]

[0028] Raw materials: commercially available or homemade.

[0029] In a 100mL round bottom flask, add 1.84g (10mmol) compound II and 10mL redistilled SOCl 2 , and then heated to reflux for 3 hours with stirring.

[0030] The reaction mixture was evaporated under reduced pressure to remove excess SOCl 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 slowly added dropwise from 1.80 g (10 mmol) III-1 and 3.04 g (30 mmol) of triethylamine dissolved in 5 mL of dry solution in dichloromethane and continued to stir overnight at room temperature. TLC showed the reaction was complete.

[0031] The reaction mixture was poured into ice water, stirred, extracted with 50mL×3 dichloromethane, combined and extracted organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a ro...

Embodiment 2

[0032] Example 2 Preparation of Compound I-2

[0033]

[0034] Raw materials: commercially available or homemade.

[0035] In a 100mL round bottom flask, add 1.84g (10mmol) compound II and 10mL redistilled SOCl 2 , and then heated to reflux for 3 hours with stirring.

[0036] The reaction mixture was evaporated under reduced pressure to remove excess SOCl 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 slowly added dropwise from 1.97 g (10 mmol) III-2 and 3.04 g (30 mmol) of triethylamine dissolved in 5 mL of dry solution in dichloromethane and continued to stir overnight at room temperature. TLC showed the reaction was complete.

[0037] The reaction mixture was poured into ice water, stirred, extracted with 50mL×3 dichloromethane, combined and extracted organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a ro...

Embodiment 3-12

[0039] Referring to the method of Examples 1 and 2, the following compounds with general formula I were synthesized.

[0040]

[0041]

[0042]

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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 trans-cyclohexane amide structured PAR-1 antagonist containing structures, such as halogenated phenyl and the like, a preparation method of the antagonist and application of the antagonist in preparation of medicines for treating thrombotic diseases, wherein R is selected from C1-C3 alkyl, C3-C5 cycloalkyl and halogen substituent.

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 with a trans-cyclohexaneamide structure containing a halogenated phenyl group and a preparation method thereof, a pharmaceutical composition containing them and a therapeutic effect on thrombotic diseases. Use in medicine. 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, thereby blocking art...

Claims

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Application Information

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IPC IPC(8): C07D295/185A61P7/02
CPCC07D295/185
Inventor 郭章华
Owner ZHEJIANG PHARMA COLLEGE
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