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Pyrrolobenzoxazinone compound and its injection and application in antithrombotic

A technology of benzoxazinones and compounds, which is applied in the field of pyrrolobenzoxazinone compounds and their injections, and can solve the problems that pyrrolobenzoxazinone compounds have not been reported.

Inactive Publication Date: 2021-06-18
YANBIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because traditional anticoagulant drugs often require injection or monitoring, their practical application has been limited to varying degrees
Therefore, it is of great significance to find new antithrombotic drugs, especially drugs against platelet aggregation, and the research on the antithrombotic aspects of the pyrrolobenzoxazinone compounds mentioned in the present invention has not been reported so far

Method used

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  • Pyrrolobenzoxazinone compound and its injection and application in antithrombotic

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: the synthesis of compound 1

[0017] Add dimethyl 2-(2-(4-methoxyphenyl)-2-oxoethylethylene)malonate (0.25 mmoL), (Z)-methyl 2- (2-oxo-2H-benzo[b][1,4]oxazine-3(4H)-methylene)acetate (0.3mmoL) and dichloroethane (2 mL), after stirring well Add ferric chloride (0.25 mmol). The reaction solution was stirred at 80° C., monitored by TLC, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound 1. After structure confirmation, the synthesized compound 1 H-NMR and 13 C-NMR data and literature (FeCl3-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines ( J. Org. Chem. 2017, 82, 13617−13625)) consistent.

Embodiment 2

[0018] Embodiment 2: the synthesis of compound 2

[0019] Add 2-methyl-2-(2-oxo-2-(thien-2-yl)ethylene)malonate (0.25mmoL), (Z)-methyl 2-( 2-oxo-2H-benzo[b][1,4]oxazine-3(4H)-methylene)acetate (0.3 mmoL) and dichloroethane (2 mL), stirred well and added Ferric chloride (0.25 mmol). The reaction solution was stirred at 80° C., monitored by TLC, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound 2. After structure confirmation, the synthesized compound 1 H-NMR and 13 C-NMR data and literature (FeCl3-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines ( J. Org. Chem. 2017, 82, 13617−13625)) consistent.

Embodiment 3

[0020] Embodiment 3: the synthesis of compound 3

[0021] Add 2-(2-oxo-2-phenylethylidene) dimethyl malonate (0.25 mmoL), ((Z)-3-(2-methoxy-2-oxoethylene) to the reaction flask Ethyl)-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate (0.3mmoL) and dichloroethane (2 mL) , after stirring evenly, add ferric chloride (0.25 mmoL). The reaction solution was stirred at 80°C, and the reaction was monitored by TLC. After the reaction was complete, it was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound 3. The structure of the synthesized compound was confirmed. 1 H-NMR and 13 C-NMR data and literature (FeCl3-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines ( J. Org. Chem. 2017, 82, 13617−13625)) consistent.

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Abstract

The present invention discloses a pyrrolobenzoxazinone compound represented by compound 1 or a pharmaceutically acceptable salt thereof. Through the in vitro platelet aggregation test of the compound, the impact on the tail bleeding time of mice and the rat right carotid artery-venous bypass thrombosis test, it is found that the compound of the present invention can pass through collagen, adenosine diphosphate and blood coagulation. The enzymatic pathway inhibits platelet aggregation and inhibits thrombus formation.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a pyrrolobenzoxazinone compound, an injection thereof and an antithrombotic application. Background technique [0002] Cardiovascular and cerebrovascular diseases are collectively referred to as cardiovascular and cerebrovascular diseases. disease. Cardiovascular and cerebrovascular disease is a common disease that seriously threatens the health of human beings, especially middle-aged and elderly people over 50 years old. It has the characteristics of high prevalence, high disability rate and high mortality rate. However, there are still more than 50% of survivors of cerebrovascular accidents who cannot take care of themselves completely. The number of people who die from cardiovascular and cerebrovascular diseases in the world is as high as 15 million every year, ranking first among various causes of death. [0003] Thrombosis is the biggest cause of cardiovascular and cerebrovascular ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04A61P7/02A61K9/08A61K47/26
CPCA61K9/0019A61K9/08A61K47/26A61P7/02C07D498/04
Inventor 马娟左红香李明月吕烨
Owner YANBIAN UNIV