Medicine for treating ischemic brain injury stroke and sequela of ischemic brain injury stroke and preparation method for medicine

A technology of compounds and organic solvents, applied in the field of inventions involving the fields of chemistry and biological sciences

Active Publication Date: 2012-09-19
薪火炙药(北京)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few effective drugs in the early recovery stage of cerebral ischemia. It is of great significance to dev

Method used

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  • Medicine for treating ischemic brain injury stroke and sequela of ischemic brain injury stroke and preparation method for medicine
  • Medicine for treating ischemic brain injury stroke and sequela of ischemic brain injury stroke and preparation method for medicine
  • Medicine for treating ischemic brain injury stroke and sequela of ischemic brain injury stroke and preparation method for medicine

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0031] Preparation Example 1 The preparation of 2-bromomethyl-3,5,6-trimethylpyrazine intermediate

[0032] Dissolve dehydrated ligustrazine 10g in 60mlCCl4, then drop into NBS 9.17g according to the molar ratio ligustrazine: NBS=1: 0.7 (can add a small amount of benzoyl peroxide as a free radical initiator), under the irradiation of an incandescent lamp, reflux React for 10-12 hours, cool, concentrate, pump off excess ligustrazine under reduced pressure in a water bath at 60-70°C, and place the residue in a refrigerator. 7.75 g of a light red semi-oil was obtained, with a yield of 70%.

preparation Embodiment 2

[0033] Preparation Example 2 Synthesis of LQC-T1 (Compound 1)

[0034] Place 3.26mmol of 2-bromomethyl-3,5,6-trimethylpyrazine prepared in Example 1 and 3.40mmol of protocatechuic acid prepared in Example 1 into a 50ml round bottom flask, add 30ml xylene , after the mixture is dissolved, add 3mmol of triethylamine, heat and reflux for 12h, TLC monitors that the reaction raw materials disappear substantially, stop the reaction, add 30ml of ethyl acetate to the reaction solution, concentrate under reduced pressure, add 4ml of methanol to the residue to dissolve, add 2.0g of silica gel to reduce The mixed sample was evaporated to dryness, and the eluent was petroleum ether: acetone = 5:1, and 0.45 g of white powder was obtained, with a yield of 48.0%, and a melting point of 219.2 to 220.1° C.; the hydrogen spectrum and carbon spectrum data of compound 1 were as follows:

[0035] 1 HNMR (500MH z , DMSO-d 6 ): 7.353~6.802(m, 3H, Ar-H), 5.323(s, 2H, O-CH 2 ), 2.503(s, 3H, 6-CH ...

preparation Embodiment 3

[0037] Preparation Example 3 Synthesis of LQC-T2 (Compound 2)

[0038] Place 4.6mmol of 2-bromomethyl-3,5,6-trimethylpyrazine and 1.5mmol of protocatechuic acid prepared in Example 1 into a 25ml round bottom flask, add 14ml of DMF and wait for the mixture to dissolve, then add 10mmol of Potassium carbonate, N 2 Protected at 85°C and stirred for 1.5h, TLC monitored that the reaction raw materials basically disappeared, stopped the reaction, filtered to remove potassium carbonate, diluted the reaction solution with saturated aqueous sodium bicarbonate solution, extracted three times with ethyl acetate, evaporated the combined extracts to dryness, and redissolved the residue in a small amount of acetone. Add 3.0 g of silica gel and evaporate to dryness under reduced pressure to mix the sample. The eluent is petroleum ether: acetone = 6:1 to obtain 0.36 g of white powder with a yield of 43.1% and a melting point of 202.2-203.0°C.

[0039] The hydrogen spectrum and carbon spectrum...

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Abstract

The invention discloses a structural general formula of a compound LQC-T and the synthesis and the application of the compound LQC-T. Pharmacological experiments prove that the compound has an obvious effect of promoting new vessels of chick chorioallantoic membranes to grow; a compound LQC-T4 has an obvious medicinal effect of treating ischemic brain injury stroke and the sequela of the ischemic brain injury stroke; the maximal LQC-T4 single-day dose of mice is 5,400mg/kg; and the compound is extremely high in safety and can be used for preparing a medicine for treating the ischemic brain injury stroke and the sequela of the ischemic brain injury stroke after toxic responses do not occur after continuous observation within 1 to 4 days. According to the structural formula of the compound LQC-T, R is protocatechuic acid, protocatechuic aldehyde, vanillic acid, gallic acid, caffeic acid, ferulic acid and other aromatic organic acids or phenols or structural analogues of the organic acids or phenols.

Description

technical field [0001] The present invention relates to the fields of chemistry and biological sciences, in particular to the general structural formula of LQC-T and its synthesis and application. Pharmacological experiments have proved that this type of compound can significantly promote the growth of new blood vessels in the chicken embryo chorioallantoic membrane, wherein LQC-T4 is effective in the treatment of It has significant drug effects on ischemic brain injury, stroke and its sequelae. LQC-T4 mice were given a single-day maximum dose of 5400mg / kg, and no toxic reactions occurred within 14 days of continuous observation, indicating that the drug is very safe and available It is used in the preparation of drugs for the treatment of ischemic brain injury, stroke and its sequelae. [0002] [0003] R represents protocatechuic acid, protocatechualdehyde, vanillic acid, gallic acid, caffeic acid, ferulic acid and other aromatic organic acids or phenols or their structur...

Claims

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Application Information

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IPC IPC(8): C07D241/12A61K31/4965A61K31/497A61P25/00A61P9/10
CPCC07D241/12A61P9/10A61P25/00
Inventor 雷海民洪缨王鹏龙郝颖智李强蔡程科
Owner 薪火炙药(北京)科技有限公司
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