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Ferulate compound and preparation method thereof

A technology of ferulic acid ester and ferulic acid, applied in the field of medicine, can solve problems such as unsatisfactory effects of finished medicines, and achieve the effect of preventing angioneurotic headaches

Inactive Publication Date: 2015-05-06
杨安民
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] It can be seen that ferulic acid, gastrodin and tofu glucoside are difficult to pass through the defect of the blood-brain barrier, which leads to their unsatisfactory drug effect, which is the clinical treatment of the pharmaceutical composition / compound described in CN102793708A and CN104231013A biggest flaw

Method used

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  • Ferulate compound and preparation method thereof
  • Ferulate compound and preparation method thereof
  • Ferulate compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Preparation of Ferulic Acid-4-Hydroxymethylphenol Ester (C-1)

[0053] Add 45 mmol of 4-hydroxybenzyl alcohol, 18 mmol of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 145 mg of 4-dimethylaminopyridine and CH 2 Cl 2 - THF (1:1, v / v) 100ml, placed in an ice bath and stirred to dissolve. Ferulic acid 15mmol dissolved in CH 2 Cl 2 - 50ml of THF (1:1, v / v) was slowly added dropwise to the reaction system. After the dropwise addition, the temperature was raised to room temperature and the reaction was stirred for 12-24 h (the reaction progress was monitored by TLC, petroleum ether-ethyl acetate=2:1, v / v). After the reaction, the reaction solution was concentrated to a paste, dissolved in ethyl acetate and washed with 1% hydrochloric acid, the organic phase was concentrated and separated on a reversed-phase silica gel column (eluent: 30% to 50% ethanol, v / v) , to obtain ferulic acid-4-hydroxymethylphenol ester (yield 21%).

[0054] 4-hydroxym...

Embodiment 2

[0055] The preparation of embodiment 2 ferulic acid-4-hydroxybenzyl alcohol ester (C-2)

[0056] Add 20mmol of p-hydroxybenzyl alcohol, 200mg of 4-methylbenzenesulfonic acid and 50ml of THF into the reaction flask, stir and dissolve in an ice bath. 15 mmol of dicyclohexylcarbodiimide was dissolved in 15 ml of DMF and added dropwise to the reaction system. Dissolve 10 mmol of ferulic acid in CH 2 Cl 2 After 30ml, it was slowly added dropwise to the reaction system. After the dropwise addition, the temperature was raised to room temperature and the reaction was stirred for 48-72 hours (the reaction progress was monitored by TLC, petroleum ether-ethyl acetate=2:1, v / v). Suction filtration after completion of the reaction, the filtrate was concentrated to a paste, dissolved in ethyl acetate and filtered to remove insoluble matter, the filtrate was washed with 5% hydrochloric acid, the organic phase was concentrated and then purified on a silica gel column (eluent: petroleum e...

Embodiment 3

[0058] Example 3 Preparation of Ferulic Acid-4-Formylphenol Ester (C-3)

[0059] Add 60mmol of 4-hydroxybenzaldehyde, 50mmol of dicyclohexylcarbodiimide, 240mg of 4-dimethylaminopyridine and CH 2 Cl 2 - THF (1:1, v / v) 200ml, placed in an ice bath and stirred to dissolve. Ferulic acid 40mmol dissolved in CH 2 Cl 2 - 100ml of THF (1:1, v / v) was slowly added dropwise to the reaction system. After the dropwise addition, the temperature was raised to room temperature and the reaction was stirred for 10-24 h (the reaction progress was monitored by TLC, petroleum ether-ethyl acetate=2:1, v / v). Suction filtration after completion of the reaction, the filtrate was concentrated to a paste, dissolved in ethyl acetate and filtered to remove insoluble matter, the filtrate was washed with 5% hydrochloric acid, the organic phase was concentrated and then purified on a silica gel column (eluent: petroleum ether-ethyl acetate =3:1, v / v) to obtain ferulic acid-4-formylphenol ester (yield...

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Abstract

The invention relates to a ferulate compound as well as a preparation method thereof and application of the compound in preparing medicaments for treatment and / or prevention of angioneurotic headache, vertigo, neurasthenia, neurasthenia syndrome, traumatic brain syndrome and cerebrovascular diseases.

Description

technical field [0001] The invention relates to a ferulic acid ester compound and a preparation method thereof, in particular to a ferulic acid-gastrodin compound, which belongs to the field of medicine. Background technique [0002] Headache, dizziness, and neurasthenia are common clinical diseases with complex and diverse manifestations and pathogenic factors. It is generally believed that dysfunction of blood vessels and nerves is an important and interactive pathogenic factor. [0003] Vascular headache refers to the clinical syndrome caused by head vasomotor dysfunction and cerebral cortex dysfunction, or temporary changes of certain body fluid substances. It is characterized by paroxysmal pulsating throbbing pain, distending pain or drilling pain in one or both temporal regions, and may be accompanied by visual hallucinations, dizziness, photophobia, hemianopia, nausea and vomiting and other symptoms of vascular autonomic dysfunction. It includes migraine, cluster hea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734C07C67/08A61K31/216A61P25/00A61P9/00A61P1/08A61P25/06A61P25/04A61P27/16
CPCC07C67/08C07C69/734
Inventor 陈雏杜俊蓉吴燕
Owner 杨安民
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