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Method for synthesizing target compound-ligustrazine derivant preventing cerebrovascular disease

A technology for cardiovascular and cerebrovascular diseases and compounds, applied in 2 fields

Inactive Publication Date: 2008-03-05
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the active design and structural modification of tetramethylpyrazine derivatives with targeting function have not been reported yet.

Method used

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  • Method for synthesizing target compound-ligustrazine derivant preventing cerebrovascular disease
  • Method for synthesizing target compound-ligustrazine derivant preventing cerebrovascular disease
  • Method for synthesizing target compound-ligustrazine derivant preventing cerebrovascular disease

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Experimental program
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preparation example Construction

[0012] 1. Preparation of intermediates

[0013] Ethyl chlorinated phosphate was dissolved in dichloromethane at a concentration of about 21mmoL, and this solution was added to a suspension of dichloromethane containing pyridine (about 20.8mmoL) to prepare a reaction solution, which was stirred continuously. The raw material 2,5-dimethylol-3,6-dimethylpyrazine was dissolved in tetrahydrofuran (about 6.1mmoL), and then the solution was added dropwise into the reaction solution at -30°C, heated to room temperature, and stirred for 18h .

[0014] Add N-(2-aminoethyl)aminomethyl polystyrene resin and dichloromethane, shake vigorously for 2h, and use the solution Filtrate through celite, elute with diethyl ether, and concentrate the filtrate in vacuo to ointment of orange-yellow phosphorylated intermediate.

[0015] 2. Preparation of 2,5-bis(phosphorylcholine)methyl-3,6-dimethylpyrazine

[0016] Dissolve the above orange-yellow phosphorylated intermediate ointment in anhydrous a...

Embodiment 1

[0018] Ethyl phosphate chloride (2mL, 21mmoL) was mixed with dichloromethane (40mL) containing pyridine (1.08mL, 20.8mmoL) to prepare a reaction solution, which was cooled to -30°C and kept stirring. 2,5-Hydroxymethyl-3,6-dimethylpyrazine (1 g, 6.1 mmoL) was dissolved in 10 mL of tetrahydrofuran, then added dropwise to the above reaction solution, heated to room temperature, and stirred for 18 h. Then add N-(2-aminoethyl) aminomethyl polystyrene resin (4.5g) and dichloromethane (10mL), shake for 2h, and the solution Filter with 2 g of diatomaceous earth, elute with diethyl ether, and concentrate the filtrate in vacuo to obtain 0.95 mg of an orange-yellow phosphorylated intermediate ointment.

[0019] Dissolve the above orange-yellow phosphorylated intermediate ointment in anhydrous acetonitrile (10 mL), then add trimethylamine (10 mL), seal the reaction solution and heat to 100° C. for 30 min with microwave. The supernatant was poured out, and the dark yellow residue was dis...

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Abstract

The present invention relates to one kind of compound and its preparation process. The compound is designed for inhibiting the function of C-reactive protein likely to cause atherosclerosis and myocardial infarction so as to prevent and treat cardiac vascular diseases. By using ligustrazine derivative 2, 5-dihydroxymethyl-3, 6-dimethyl pyrazine as precursor and through a series of reaction, compound 2, 5-bis(choline phosphate) methyl-3, 6-dimethyl pyrazine capable of inhibiting the activity of C-reactive protein is prepared.

Description

technical field [0001] The invention relates to a compound and a preparation method thereof, in particular to 2,5-bis(phosphorylcholine)methyl-3,6-dimethylpyrazine and a preparation method thereof. technical background [0002] Tetramethylpyrazine (Ligustrazine, Lig; Tetramethylpyrazine, TMP) is one of the main chemical components in the rhizomes of Umbelliferae Ligusticum Chuanxiong, Zingiberaceae Ezhu and Euphorbiae Jatropha. Ligustrazine has multiple effects such as dilating blood vessels, inhibiting platelet aggregation, preventing thrombosis, and improving cerebral ischemia. 7:661-663). Because ligustrazine has the characteristics of rapid absorption, wide distribution and rapid elimination mainly in the liver, fast metabolism in vivo, low bioavailability, and short half-life (t1 / 2=2.89h), in order to maintain effective drug treatment concentration, clinically Frequent administration is required, so it is easy to cause accumulation and poisoning, which limits its appl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6509A61K31/675A61P9/10A61P9/00
Inventor 于超何俊琳王应雄
Owner CHONGQING MEDICAL UNIVERSITY
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