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Dual brain-targeting prodrugs using organic amine-modified vitamin C as carrier

A technology of vitamins and organic amines, applied in the field of medicine, can solve problems such as low permeability, clinical application restrictions, and physical hazards

Active Publication Date: 2019-01-15
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low permeability of ibuprofen, the distribution in the CNS is limited, and the effective therapeutic concentration is low. In order to achieve a better therapeutic effect, the dose of the drug needs to be increased to make the drug reach a higher concentration in the body, but with At the same time, the drug concentration in other organs will also increase, and the toxic and side effects will also increase, which will cause greater harm to the body. Long-term use of these drugs will cause adverse reactions such as gastrointestinal discomfort, headache, dizziness, and even nephrotoxicity. , so the clinical application of ibuprofen is greatly limited

Method used

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  • Dual brain-targeting prodrugs using organic amine-modified vitamin C as carrier
  • Dual brain-targeting prodrugs using organic amine-modified vitamin C as carrier
  • Dual brain-targeting prodrugs using organic amine-modified vitamin C as carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of compound 1

[0020]

[0021] 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, and wash the filter cake with cold acetone , and dried the filter cake to obtain white solid 1 (18g), yield 73.3%. m.p.: 202-204°C.

Embodiment 2

[0023] Preparation of compound 2

[0024]

[0025] Xiang 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), with a yield of 44.1%.

Embodiment 3

[0027] Preparation of compound 3

[0028]

[0029] CH to 2 (4.85g, 12.23mmol) 3 CN (200ml) solution was added with HCl solution (20ml, 2mol / L), and the reaction was stirred at an external temperature of 30°C for 3h. The solvent was spun off, EA was added, washed twice with water, twice with saturated saline, and washed with anhydrous Na 2 SO 4 Drying and concentration gave yellow oil 3 (4.4 g), yield 100%, and then slowly solidified into a white solid. m.p.: 67-69°C.

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Abstract

The invention discloses a dual brain-targeted prodrug with an organic-amine-modified vitamin C being a carrier. The dual brain-targeted prodrug is a structure or pharmacy acceptable salt or water compound shown in the general formula (I), wherein X represents -(CH2)n-, -C(O)-(CH2)n-C(O)-or-(CH2)m-O-, -(CH2)m-NH-, -(CH2)m-C(O)-, -c(o)-(ch2)M-, -C(O)-(CH2)m0NH-, n represents 0-6, m represents 1-4, and Drug represents medicine acting on the central nervous system. The series of prodrug can improve brain-targeted performance of the medicine and increase the concentration of the central nervous system, in this way, the treatment effect of the medicine is improved, meanwhile, medicine distributed on peripheral organs is reduced, and toxic and side effects of the medicine are reduced.

Description

technical field [0001] The invention relates to a class of novel compounds, in particular to the design, preparation and preliminary targeting determination of a class of dual brain-targeting prodrugs with organic amine-modified vitamin C as a carrier. It belongs to the field of medical technology. 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 m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/54A61K31/192A61K45/00C07D307/62
CPCA61K31/192A61K45/00C07D307/62
Inventor 吴勇海俐刘莎邱淑兵屈博毅李晓岑靳秀秀吕光辉
Owner SICHUAN UNIV
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