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Amphiphilic anti-cancer drug compound modified by water-soluble vitamin E derivative, preparation, preparation method and application for compound

A technology of water-soluble vitamins and anti-cancer drugs, which is applied to compounds, chemical instruments and methods, and drug combinations of elements in group 5/15 of the periodic table, and can solve problems such as poor solubility

Inactive Publication Date: 2012-06-13
NANJING MEIXINING MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In order to improve the solubility of drugs, technologies such as emulsion (Emulsion) and micelles (micelle) are widely used in the preparation of poorly water-soluble or water-insoluble drugs, but so far there is no preparation technology that can be applied to camptothecin. Because of its poor solubility in water and organic solvents

Method used

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  • Amphiphilic anti-cancer drug compound modified by water-soluble vitamin E derivative, preparation, preparation method and application for compound
  • Amphiphilic anti-cancer drug compound modified by water-soluble vitamin E derivative, preparation, preparation method and application for compound
  • Amphiphilic anti-cancer drug compound modified by water-soluble vitamin E derivative, preparation, preparation method and application for compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1. 7-ethyl-10-hydroxycamptothecin R-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid methoxypolyethylene Synthesis of glycol ester-6-succinate

[0140] The synthesis of the amphiphilic anticancer drug compound includes the following steps:

[0141] 1) Synthesis of R-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid methoxyheptapolyethylene glycol ester

[0142] The reaction formula is as follows:

[0143]

[0144] Experimental steps:

[0145] In a 50mL reaction flask, add 978mg (8mmol) 4-dimethylaminopyridine, 1.022mg (4mmol) 2-chloro-1-methylpyridinium iodide and 1021mg (3mmol) heptaethylene glycol monomethyl ether, With electromagnetic stirring, 751 mg (3 mmol) of R-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxyl was slowly added dropwise to the reaction solution. acid and 10 mL of a solution of N,N-dimethylformamide. The reaction was carried out under the protection of nitrogen at room temperature for 12 h, filtered to remove s...

Embodiment 2

[0168] Example 2. 7-ethyl-10-hydroxycamptothecin (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid polyethylene glycol monomethyl ether Synthesis of Ester-6-Succinate

[0169] 1) Synthesis of (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid polyethylene glycol monomethyl ether ester (polyethylene glycol monomethyl ether) The average molecular weight of: Mn=550)

[0170] The reaction formula is

[0171]

[0172] Experimental steps:

[0173] In a 100mL reaction flask, add 2.20g (4mmol) polyethylene glycol monomethyl ether (average molecular weight is Mn=550), 1.45g (12mmol) 4-dimethylaminopyridine, 1.53g (6mmol) 2-chloro- 1-Methylpyridinium iodide and 30 mL of dioxane were stirred magnetically, and 1.00 g (4 mmol) of (±)-6-hydroxy-2,5,7,8-tetrakis was slowly added dropwise to the reaction solution. A solution of methylchroman-2-carboxylic acid and 30 mL dioxane. The reaction was carried out under the protection of nitrogen at room temperature for 12 h,...

Embodiment 3

[0196] Example 3. 7-ethyl-10-hydroxycamptothecin N-methoxyheptaethylene glycol amine R-(+)-6-hydroxy-2,5,7,8-tetramethylbenzodihydropyridine Synthesis of Pyran-2-carboxamide-6-succinate

[0197] The synthesis of the amphiphilic anticancer drug compound includes the following steps:

[0198] 1) Synthesis of N-methoxyheptapolyethylene glycol amine group R-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide

[0199] The reaction formula is as follows:

[0200]

[0201] Experimental steps:

[0202] In a 50mL reaction flask, add 825mg (4mmol) N,N'-dicyclohexylcarbodiimide (DCC), 1018mg (3mmol) methoxyheptapolyethylene glycol amine, 751mg (3mmol) R-(+ )-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid and 10 mL of N,N-dimethylformamide. Electromagnetic stirring, react for 12h at room temperature and under the protection of nitrogen, remove the solid material by filtering, concentrate the filtered solution to 10mL with a rotary evaporator, and separate the column laye...

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Abstract

The invention discloses an amphiphilic anti-cancer drug compound modified by a water-soluble vitamin E derivative. The amphiphilic anti-cancer drug compound has the structure of the following formula I or II. The anti-cancer drug active part camptothecin or camptothecin derivative, and amphiphilic part water-soluble vitamin E alkoxy polyethylene glycol ester or amide are covalently bonded by linking groups to form the amphiphilic anti-cancer drug compound. The invention further relates to a preparation, a preparation method and an application for the medicine compound.

Description

technical field [0001] The present invention relates to a novel anticancer drug compound, a preparation method and application thereof, in particular to an amphiphilic anticancer drug compound modified by a water-soluble vitamin E derivative, a preparation comprising the compound, a preparation method and an anticancer drug compound application of drugs. Background technique [0002] Many compounds with anticancer activity have become an obstacle to drug development due to their insolubility in water and / or other biocompatible solvents, or poor stability in water and biocompatible solvents, often resulting in delays in drug development time. It is estimated that as many as 40 percent of screened potentially valuable drug candidates are rejected from formulation research and development due to their poor water solubility, and 30 percent of existing drugs are poorly soluble. Several technologies are currently being researched and developed to address the poor solubility of ph...

Claims

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Application Information

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IPC IPC(8): C07D491/22C07F9/6561C08G65/48A61K31/4745A61K31/685A61K31/765A61K9/08A61K9/00A61P35/00
CPCA61K9/0019A61K47/48C08G65/48A61K9/08A61K9/00C07D491/22A61K9/1075A61K31/4745C07F9/6561C07F9/65522A61K47/48107A61K31/765A61K31/685A61K47/551A61P35/00C08G65/33396C08L2203/02
Inventor 张跃华
Owner NANJING MEIXINING MEDICAL TECH
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