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Paclitaxel modified by branched polyethylene glycol and preparation method of paclitaxel

A technology of polyethylene glycol and paclitaxel, which is applied in the directions of non-active ingredients medical preparations, medical preparations containing active ingredients, and pharmaceutical formulas, can solve problems such as unsatisfactory effects of improving water solubility and bioavailability, and achieves The effect of high bioavailability, improved solubility, and high application value

Inactive Publication Date: 2016-02-03
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Documents CN1283643, CN1895676 and CN101569747 disclose paclitaxel modified by linear polyethylene glycol, but their effects in improving water solubility and bioavailability are not satisfactory

Method used

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  • Paclitaxel modified by branched polyethylene glycol and preparation method of paclitaxel
  • Paclitaxel modified by branched polyethylene glycol and preparation method of paclitaxel
  • Paclitaxel modified by branched polyethylene glycol and preparation method of paclitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of compound I:

[0017]

[0018] In the above formula, the molecular weight of mPEG is 800.

[0019] Add II (1g) and PTX (0.5g) into dichloromethane (40ml), stir to dissolve, then add catalytic amounts of DMAP and DCC (0.13g) respectively, under argon protection, stir at room temperature for 24 hours, TLC plate detection The raw material PTX reacted completely. Filtrate, pour the filtrate into cold ether to obtain a white precipitate, filter, and vacuum-dry the filter cake to obtain a branched polyethylene glycol-modified paclitaxel compound (mPEG-PTX) white powder, re-dissolve the obtained solid in dichloromethane , then concentrated to 1ml, then added isopropanol to separate out a white solid (1.04g, yield 74%, paclitaxel content 32%), which is the target product I.

Embodiment 2

[0021] Preparation of compound I:

[0022]

[0023] In the above formula, the molecular weight of mPEG is 1600.

[0024] Add II (1g) and PTX (0.25g) into dichloromethane (30ml), stir to dissolve, then add catalytic amounts of DMAP and DCC (0.09g) respectively, under argon protection, stir at room temperature for 24 hours, TLC plate detection The raw material PTX reacted completely. Filtrate, pour the filtrate into cold ether to obtain a white precipitate, filter, and vacuum-dry the filter cake to obtain a branched polyethylene glycol-modified paclitaxel compound (mPEG-PTX) white powder, re-dissolve the obtained solid in dichloromethane , then concentrated to 1ml, then added isopropanol to separate out a white solid (0.81g, yield 64.8%, paclitaxel content 19.2%), which is the target product I.

[0025] Example 2

[0026] Preparation of compound I:

[0027]

[0028] In the above formula, the molecular weight of mPEG is 2000.

[0029] Add II (2g) and PTX (0.3g) into di...

Embodiment 3

[0031] Preparation of compound I:

[0032]

[0033] In the above formula, the molecular weight of mPEG is 2500.

[0034] Add II (2g) and PTX (0.32g) into dichloromethane (35ml), stir to dissolve, then add catalytic amounts of DMAP and DCC (0.10g) respectively, under argon protection, stir at room temperature for 24 hours, TLC plate detection The raw material PTX reacted completely. Filtrate, pour the filtrate into cold ether to obtain a white precipitate, filter, and vacuum-dry the filter cake to obtain a branched polyethylene glycol-modified paclitaxel compound (mPEG-PTX) white powder, re-dissolve the obtained solid in dichloromethane , then concentrated to 1ml, then added isopropanol to separate out a white solid (1.4g, yield 60.1%, paclitaxel content 11.7%), which is the target product I.

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PUM

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Abstract

The invention discloses paclitaxel modified by branched polyethylene glycol and a preparation method of paclitaxel, wherein the structure of the paclitaxel modified by branched polyethylene glycol is shown as the formula I. According to the preparation method, in a solvent, branched polyethylene glycol and paclitaxel formed by connecting two amino groups of lysine with polyethylene glycol respectively are taken as raw materials, 4-dimethylaminopyridine is taken as a catalyst, and N,N'-dicyclohexylcarbodiimide is taken as a condensating agent, and the branched methoxy polyethylene glycol paclitaxel compound is obtained through reaction. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a branched polyethylene glycol-modified paclitaxel and a preparation method thereof. Background technique [0002] Many drugs such as Paclitaxel (PTX) have good activity, but because of their extremely poor water solubility, they often lead to extremely low bioavailability or cannot be formulated into solutions for injection. In order to increase the bioavailability of such drugs, it is necessary to increase the solubility of these drugs in water. Conventional methods currently used to solubilize these poorly soluble drugs include mixed solvent method, solubilizer and solubilization method, solubilizer solubilization method, soluble salt method, solid dispersion or clathrate method, etc. Different solubilization methods are often selected for different drug characteristics. [0003] Paclitaxel has good antitumor activity, but its water solubility is extremely poor (about 0.25...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K31/337C08G65/48A61P35/00A61K47/60
Inventor 陈芳军
Owner 湖南华腾制药有限公司
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