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Application of ascorbyl ibuprofenate in preparing brain-targeted preparation and preparation method thereof

A technology of ibuprofen axetil and vitamins, applied in the directions of anti-inflammatory agents, non-central analgesics, antipyretics, etc., can solve the problems of less distribution and limitation, and achieve low production cost, high targeting index and high yield high effect

Inactive Publication Date: 2012-11-14
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the difficulty of traditional ibuprofen preparations through the blood-brain barrier, the distribution in the brain is very small, which largely limits the use of ibuprofen as a neuroprotective agent for Alzheimer's disease (AD) and neurological disorders. Wide application in sexual diseases

Method used

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  • Application of ascorbyl ibuprofenate in preparing brain-targeted preparation and preparation method thereof
  • Application of ascorbyl ibuprofenate in preparing brain-targeted preparation and preparation method thereof
  • Application of ascorbyl ibuprofenate in preparing brain-targeted preparation and preparation method thereof

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Embodiment Construction

[0027] 1. Synthesis of vitamin C-ibuprofen ester.

[0028] 1. The 2 and 3 hydroxyl groups of vitamin C are protected.

[0029] Add vitamin C, potassium carbonate and dimethyl sulfoxide into an eggplant-shaped bottle filled with nitrogen, stir at room temperature to dissolve, add benzyl bromide and stir at room temperature for 4-5 hours. The molar ratio of vitamin C, potassium carbonate and benzyl bromide is 1:3.2:2.2. The reaction solution was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure and spun to obtain a brown-yellow viscous substance. The light yellow oil was separated by silica gel column chromatography (ethyl acetate-petroleum ether, volume ratio 1:1), which was detected as vitamin C protected by benzyl groups at the 2 and 3 positions. The synthetic route is as follows: figure 1 shown.

[0030] 2. 6-position esterification reaction.

[0031] Weigh i...

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Abstract

The invention discloses application of ascorbyl ibuprofenate in preparing a brain-targeted preparation and a preparation method thereof. The preparation method comprises the following steps: reaction of vitamin C and benzyl bromide to generate vitamin C2, 3- site hydroxy protective reaction, 6- site esterification reaction, and debenzylation reaction. The invention has the advantages of simple method, high yield, cheap and accessible reactants, low production cost and the like. The experiment proves that the ascorbyl ibuprofenate (IAA) is stable in plasma and can be quickly hydrolyzed into ibuprofen in brains. The mouse in-vivo distribution result indicates that after injecting the ascorbyl ibuprofenate via the caudal vein, the ibuprofen concentration in brains is obviously higher than the ibuprofen unit (IBU), and the AUC0-8h is twice as the IBU, which indicates strong brain targeting action.

Description

technical field [0001] The invention relates to the preparation and application of ibuprofen prodrugs, in particular to the application of vitamin C-ibuprofen ester in the preparation of brain targeting preparations and the preparation method thereof. Background technique [0002] Non-steroidal anti-inflammatory drugs (NSAIDs) are a class of widely used therapeutic drugs. In recent years, there has been a lot of evidence that NSAIDs can be used as neuroprotective agents for Alzheimer's disease (AD) and neuropathic Disease prevention and treatment. Therapeutic studies have shown that long-term use of NSAIDs can reduce the risk of AD. In vitro experiments have shown that NSAID can inhibit β-amyloid (Aβ) proliferation, reduce Aβ production, and limit the activity of microglia and astrocytes. Many NSAIDs have good curative effect on AD, such as ibuprofen, flurbiprofen and indomethacin, etc., but their distribution in the brain is very little. Mainly because the brain has obst...

Claims

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Application Information

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IPC IPC(8): A61K31/375A61K31/192C07D307/62A61P29/00
Inventor 胡海燕李玲庹珏朱文博颜光美
Owner SUN YAT SEN UNIV