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Injection of oligoethylene glycol-modified docetaxel derivative

A technology of oligoethylene glycol and docetaxel, which is applied in the field of injection of docetaxel derivatives, and can solve the problems of low drug loading, high toxicity, and poor stability

Active Publication Date: 2019-02-26
NANJING YOUYI MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The object of the present invention is to provide an injection of docetaxel derivatives modified by oligoethylene glycol, so as to overcome the shortcomings of docetaxel and docetaxel derivative preparations with low drug loading, poor stability, and high toxicity. , and improve the antitumor therapeutic effect of the drug

Method used

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  • Injection of oligoethylene glycol-modified docetaxel derivative
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  • Injection of oligoethylene glycol-modified docetaxel derivative

Examples

Experimental program
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Embodiment 1 8

[0081] Embodiment 1. the synthesis of octapolyethylene glycol monomethyl ether docetaxel-2'-diglycolate

[0082] The synthesis of the docetaxel derivative comprises the following steps:

[0083] 1) Synthesis of octapolyethylene glycol monomethyl ether diglycolate

[0084] The reaction formula is as follows:

[0085]

[0086] Experimental steps:

[0087] Method 1: In a 100mL round bottom flask, add 2.306g (6mmol) of dried octapolyethylene glycol monomethyl ether (1), 1.044g (9mmol) of diglycolic anhydride and 200mg of tin 2-ethylhexanoate, Add 30 mL of toluene, stir, and heat to reflux under nitrogen protection until the reaction is complete. After removing the toluene in the reaction solution with a rotary evaporator, add 20 mL of ethyl acetate, stir, and then add 10 mL of diethyl ether, a white solid precipitates, remove the solid matter by filtration, concentrate the filtrate to 10 mL with a rotary evaporator, and separate by column layer to obtain 2. 306g octapolyeth...

Embodiment 2

[0094] Embodiment 2. Synthesis of hexaethylene glycol monomethyl ether docetaxel-2'-diglycolate

[0095] The synthesis of the docetaxel derivative comprises the following steps:

[0096] 1) Synthesis of Hexaethylene Glycol Monomethyl Ether Diglycolate

[0097] The reaction formula is as follows:

[0098]

[0099] Experimental steps:

[0100] In a 100mL round bottom flask, add 1.7787g (6mmol) of dried hexapolyethylene glycol monomethyl ether (5), 1.044g (9mmol) of diglycolic anhydride and 200mg of tin 2-ethylhexanoate, and then add 30mL toluene, stirred, and heated to reflux under nitrogen protection until the reaction was complete. After removing the toluene in the reaction solution with a rotary evaporator, add 20 mL of ethyl acetate, stir, and then add 10 mL of diethyl ether, a white solid precipitates, remove the solid matter by filtration, concentrate the filtrate to 10 mL with a rotary evaporator, and separate by column layer to obtain 1.914g hexapolyethylene glyco...

Embodiment 3

[0106] Example 3. Synthesis of tetrapolyethylene glycol monomethyl ether docetaxel-2'-diglycolate

[0107] The synthesis of the docetaxel derivative comprises the following steps:

[0108] 1) Synthesis of tetrapolyethylene glycol monomethyl ether diglycolate

[0109] The reaction formula is as follows:

[0110]

[0111] Experimental steps:

[0112] In a 100mL round bottom flask, add 1.250g (6mmol) of dried tetrapolyethylene glycol monomethyl ether (9), 1.044g (9mmol) of diglycolic anhydride and 200mg of tin 2-ethylhexanoate, and then add 30mL toluene, stirred, and heated to reflux under nitrogen protection until the reaction was complete. After removing the toluene in the reaction solution with a rotary evaporator, add 20 mL of ethyl acetate, stir, and then add 10 mL of diethyl ether, a white solid precipitates, remove the solid matter by filtration, concentrate the filtrate to 10 mL with a rotary evaporator, and separate by column layer to obtain 1.650g tetrapolyethyle...

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Abstract

The invention discloses an injection of an oligoethylene glycol-modified docetaxel derivative having good anticancer effect, which contains the oligoethylene glycol-modified docetaxel derivative having a structure of a formula I, the oligoethylene glycol-modified docetaxel derivative is dissolved in a lipophilic medium, and dispersed in an aqueous phase through the action of a surfactant in termsof nanoparticles; or directly dispersed in the aqueous phase through the action of the surfactant in terms of nanoparticles; wherein R is an alkyl group of C1 to C5; and n = 1 to 10. The injection comprises a liposome agent, an emulsion and a micelle agent, and has the characteristics of low toxicity, drug loading and stability improvement, and targeted drug delivery, so that the anti-tumor therapeutic effect of the drug is improved, the toxicity is reduced, and the patient tolerance is increased.

Description

technical field [0001] The invention relates to a docetaxel anticancer drug compound preparation, in particular to an injection of a docetaxel derivative modified by oligoethylene glycol (polymerization degree n=1-10). Background technique [0002] Docetaxel (formula 1), also known as docetaxel, is a lipophilic taxane antineoplastic drug, belonging to the cytostatic class of drugs, by strengthening tubulin polymerization and inhibiting microtubule depolymerization The effect is to form stable non-functional microtubule bundles, thereby destroying the mitosis of tumor cells to achieve the anti-tumor effect. The intracellular concentration of docetaxel is 3 times higher than that of paclitaxel, and the intracellular residence time is longer, so it has stronger anti-tumor activity than paclitaxel. It is mainly used clinically for the treatment of advanced breast cancer, ovarian cancer, non-small cell lung cancer, head and neck cancer, and small cell lung cancer; it also has ce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/127A61K9/107A61K31/337A61P35/00
CPCA61K9/0019A61K9/107A61K9/1075A61K9/127A61K31/337
Inventor 张跃华赵梦尧
Owner NANJING YOUYI MEDICAL TECH CO LTD
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