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Triazolo[4,5-d]pyrimidine compound and its synthesis method, application and composition

A compound, triazolo technology, applied in the field of triazolo[4,5-d]pyrimidine compound and its synthesis, can solve the problem of reducing competitive advantage, high cost of ticagrelor medication, complex structure of ticagrelor, etc. problem, to achieve the effect of simple structure

Active Publication Date: 2017-11-21
ZHUHAI UNITED LAB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ticagrelor has a complex structure with a molecular weight of more than 500 and six chiral centers. In comparison, the complexity is far more than that of clopidogrel and prasugrel.
This results in high drug costs for ticagrelor, reducing its competitive advantage

Method used

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  • Triazolo[4,5-d]pyrimidine compound and its synthesis method, application and composition
  • Triazolo[4,5-d]pyrimidine compound and its synthesis method, application and composition
  • Triazolo[4,5-d]pyrimidine compound and its synthesis method, application and composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] This example provides the compound (2S)-3-(7-((R)-1-phenylethylamine)-5-n-propylmercapto-3H-[1,2,3]triazolo[4,5- d] the synthesis of pyrimidin-3-yl)-1,2-propanediol is synthesized by the following route:

[0037]

[0038] Specific steps are as follows:

[0039] (1) Weigh the raw material (2S)-3-(5-amino-6-chloro-2-n-propylmercaptopyrimidine-4-amino)-1,2-propanediol (4.0g) into a 250mL three-necked bottle, add Ethyl acetate (80 mL), stirred to dissolve all the raw materials. After adding acetic acid (7.2 g), sodium nitrite aqueous solution (40 mL) with a concentration of 1.2 g / 40 mL was added dropwise at room temperature, keeping the temperature not exceeding 30°C. After the dropwise addition, continue to stir the reaction at room temperature for 1-4h;

[0040] (2) After the disappearance of the raw materials in the monitoring step (1), an aqueous solution (40 mL) of potassium carbonate having a concentration of 15.1 g / 40 mL was added dropwise. After the dropwise ...

Embodiment 2

[0045] This example provides the compound (2S)-3-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropylamino)-5-n-propylmercapto-3H-[1,2 ,3] Triazolo[4,5-d]pyrimidin-3-yl)-1,2-propanediol is synthesized by the following route:

[0046]

[0047] Specific steps are as follows:

[0048] (1) Weigh the raw material (2S)-3-(5-amino-6-chloro-2-n-propylmercapto-4-amino)-1,2-propanediol (2.87g) into a 250mL three-necked flask, add Add 40mL of ethyl acetate and 30mL of purified water, then add acetic acid (5.2g), stir, then add dropwise 30mL of an aqueous solution of 0.70g / 30mL sodium nitrite, control the temperature not to exceed 30°C, and continue stirring for 1 -4h;

[0049] (2) After the raw material of monitoring step (1) disappears, 30 mL of an aqueous solution of potassium carbonate with a concentration of 10.8 g / 30 mL is added dropwise. After the dropwise addition, the raw material (1R,2S)-3,4-difluorophenyl ring Propylamine (3.7g), continue to stir and react for 10-24h;

[0050] ...

Embodiment 3

[0054] This example provides the synthesis of the compound 2-(7-benzylamino-5-n-propylmercapto-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)ethanol, by The following paths are synthesized:

[0055]

[0056] Specific steps are as follows:

[0057] (1) Weigh the raw material 2-(5-amino-6-chloro-2-n-propylthiopyrimidine-4-amino)ethanol (4.0g) into a 250mL three-necked flask, add 40mL of purified water and 40mL of ethyl acetate, Then add acetic acid (6.3g), stir, then dropwise add 40mL of an aqueous solution of sodium nitrite with a concentration of 1.10g / 40mL, control the temperature not to exceed 30°C, and continue stirring for 1-3h after the dropwise addition;

[0058] (2) After the raw material of the monitoring step (1) disappeared, 40 mL of an aqueous solution of potassium carbonate with a concentration of 12.9 g / 40 mL was added dropwise. After the dropwise addition, benzylamine (2.1 g) was dropped into, and the stirring reaction was continued for 10-20 h;

[0059] (3) Monit...

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Abstract

The present invention provides a triazolo[4,5-d]pyrimidine compound, which is characterized in that it has the structure shown in formula (I), using the triazolo[4,5-d]pyrimidine compound provided by the present invention, the structure It is simple, has anti-platelet aggregation activity, and can be used for the prevention and treatment of cardiovascular and cerebrovascular diseases such as myocardial infarction, angina pectoris, and cerebral infarction.

Description

technical field [0001] The invention relates to a triazolo[4,5-d]pyrimidine compound and its synthesis method, application and composition. Background technique [0002] In the prior art, thrombosis is a very harmful cardiovascular and cerebrovascular disease. About 12 million people die from thrombosis every year in the world, which is close to a quarter of the total death toll. Common thrombotic diseases include coronary syndrome (myocardial infarction, unstable angina, etc.), cerebral infarction, and various venous thrombosis. The formation of thrombus is mainly due to blood coagulation and platelet adhesion and aggregation. The aggregation of platelets on the inner wall of blood vessels is an important cause of thrombus formation. By inhibiting the aggregation of platelets, the formation of thrombus can be effectively prevented. Antiplatelet aggregation drugs are the main antithrombotic drugs in clinical practice. According to IMS statistics, in 2009, the global marke...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P7/02A61P9/10
Inventor 刘斌左斌海许华锋柯兴斌邓培玲孙超
Owner ZHUHAI UNITED LAB