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Brain-targeting prodrug with vitamin C as carrier

A technology of vitamins and carriers, applied in pharmaceutical formulas, medical preparations of non-active ingredients, organic chemistry, etc., can solve problems such as toxic and side effects, and reduce the proportion of brain tissue distribution

Active Publication Date: 2013-03-27
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, long-term use of these drugs has varying degrees of gastrointestinal discomfort, headache, dizziness, and even adverse reactions such as nephrotoxicity
These adverse reactions are mainly caused by the distribution of drugs in the body. When the drug is distributed more in peripheral organs, it is easy to produce toxic side effects, and it will also reduce its distribution ratio in brain tissue.

Method used

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  • Brain-targeting prodrug with vitamin C as carrier
  • Brain-targeting prodrug with vitamin C as carrier
  • Brain-targeting prodrug with vitamin C as carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] compound 1 preparation of

[0023]

[0024] Add acetyl chloride (0.4mL, 5.7mmol) to a suspension of vitamin C (L-Ascorbic acid) (20g, 114mmol) in acetone (re-distilled, 150mL), stir at room temperature for 20h; filter the reaction solution, wash the filter cake with cold acetone , dry the filter cake to obtain a white solid 1 18g, yield 73.3%.

Embodiment 2

[0026] compound 2 preparation of

[0027]

[0028] Towards 1 (6g, 27.75mmol), K 2 CO 3 Add redistilled acetone (100mL) to the powder (11.3g, 81.5mmol), raise the temperature to reflux, add BnBr (8.74mL, 73.6mmol) to the suspension, after 4.5h, remove the solvent under reduced pressure, and add a small amount of water in turn , diethyl ether, a white solid was precipitated, filtered, and the filter cake was washed with cold water and cold diethyl ether; the filter cake was dried to obtain a white solid 2 4.85g, yield 44.1%.

Embodiment 3

[0030] compound 3 preparation of

[0031]

[0032] Towards 2 (4.85g, 12.23mmol) CH 3 CN (200mL) solution was added with HCl solution (20mL, 2mol / L), and stirred at an external temperature of 30°C for 3h. Spin off the solvent, add EA, followed by H 2 O×2, brine×2, anhydrous Na 2 SO 4 dried and concentrated to yellow oil 3 (4.4g), the yield was 100%, and slowly solidified into a white solid.

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PUM

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Abstract

The invention discloses a brain-targeting prodrug with vitamin C as a carrier, which is a structure shown in the general formula (I) or a pharmaceutically acceptable salt or hydrate thereof, wherein X is -(CH2)n-, -C(O)-(CH2)n-C(O)- or -O-(CH2)m-, -NH-(CH2)m-, -C(O)-(CH2)m- or -NH-(CH2)m-C(O)-, n is 0- 6, and m is 1-4; Y is -(CH2)a-, -C(O)-(CH2)a-C(O)- or -O-(CH2)b-, -NH-(CH2)b-, -C(O)-(CH2)b-, -NH-(CH2)b-C(O)-, a is 0-6, and b is 1-4; and drug1 and Drug2 represent independent different or same drugs acting on the central nervous system. The invention provides a series of drugs, which can improve the brain targeting property of drugs and the central concentration of the drugs, thereby enhancing the curative effects of the drugs; and meanwhile, the distribution of drugs on peripheral organs is reduced, and the toxic or side effect of the drugs is reduced.

Description

technical field [0001] The present invention relates to a class of novel compounds, in particular to the preparation, use and preliminary targeting determination of a class of brain-targeted prodrugs with vitamin C as a carrier. Background technique [0002] According to statistics, about 1 / 5 of the world's population suffers from various types and degrees of central nervous system (CNS) diseases, including brain tumors, acute or chronic pain syndrome, epilepsy, encephalitis, cerebral ischemia and neurodegeneration Diseases (e.g. Alzheimer's, Parkinson's, etc.). As the world's population ages, this trend will intensify and have serious implications for human health. The existence of the blood-brain barrier (BBB) ​​has a certain protective effect on the human central nervous system, but it also restricts many substances from entering the brain from the blood. Almost all macromolecules and 95% of small molecule drugs cannot effectively enter the brain and central nervous sys...

Claims

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Application Information

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IPC IPC(8): A61K47/48C07D307/62C07D407/04
Inventor 吴勇海俐李晓岑米洁尤静
Owner SICHUAN UNIV
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