Terminal aldehyde polyoxyethylene-diethyl pentetic acid block polymer and its synthesizing method

A technology of diethylenetriaminepentaacetic acid block and aldehyde-terminated polyoxyethylene, which is applied in the fields of medical science and chemical synthesis, can solve the problems of long half-life and slow elimination speed, and achieve long half-life, prolonged residence time, biophase good capacitive effect

Inactive Publication Date: 2006-03-08
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Gadopentetate dimeglumine is not suitable for use in imaging of cardiac and vascular disease, usually so-called blood pool imaging contrast-enhancing agents, which require a very slow elimination rate, ie a long half-life

Method used

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  • Terminal aldehyde polyoxyethylene-diethyl pentetic acid block polymer and its synthesizing method
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  • Terminal aldehyde polyoxyethylene-diethyl pentetic acid block polymer and its synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The first step isocyanate-terminated polymer preparation

[0057] First, the raw material of the present invention, the hydroxyl-terminated poly Oxyethylene-diethylenetriaminepentaacetic acid block polymer (n=18, x=1, average molecular weight is 1960), other raw materials: diisocyanate is isophorone diisocyanate (IPDI), catalyst is dilauric acid Dibutyltin, the solvent is dichloromethane;

[0058] Then, the amount of polyoxyethylene-diethylenetriaminepentaacetic acid block polymer, isophorone diisocyanate, dibutyltin dilaurate and methylene chloride added in amounts of 3g, 0.68g, and 0.06g respectively And 40g, according to the polyoxyethylene-diethylenetriaminepentaacetic acid block polymer of terminal hydroxyl: isophorone diisocyanate: dibutyltin dilaurate: the weight ratio of dichloromethane is 1: 0.227: 0.02: 13.3 Measured, reacted at 40°C for 3 hours under stirring to obtain 3.68 g of isocyanate-terminated polymer;

[0059] Synthesis of crude product of terminal...

Embodiment 2

[0063] In the first step, n=18, x=1, and the average molecular weight of the polyoxyethylene-diethylenetriaminepentaacetic acid block polymer of the hydroxyl-terminated raw material synthesized according to Example 1 are 1160, and the other raw material diisocyanate is isophorone Diisocyanate (IPDI), the catalyst is dibutyltin dilaurate, the solvent is dichloromethane, hydroxyl-terminated polyoxyethylene-diethylenetriaminepentaacetic acid block polymer, isophorone diisocyanate (IPDI), dilauric acid The addition amount of dibutyltin dichloride and dichloromethane is respectively 3g, 0.57g, 0.06g and 12g, the polyoxyethylene-diethylenetriamine pentaacetic acid block polymer of terminal hydroxyl, isophorone diisocyanate, dilauric acid The weight ratio of dibutyltin to dichloromethane is 1: 0.19: 0.02: 4, and reacted for 3 hours at 40° C. with stirring to obtain 3.57 g of isocyanate-terminated polymer;

[0064] Synthesis of crude product of terminal aldehyde group polymer in the s...

Embodiment 3

[0068] In the first step, the polyoxyethylene-diethylenetriaminepentaacetic acid block polymer of the hydroxyl-terminated raw material synthesized according to Example 1 has n=45, x=1, an average molecular weight of 4350, and the diisocyanate is isophorone diisocyanate (IPDI), the catalyst is dibutyltin dilaurate, the solvent is dichloromethane, the addition of polyoxyethylene-diethylenetriaminepentaacetic acid block polymer, IPDI, dibutyltin dilaurate and dichloromethane Be respectively 13.06g, 1.39g, 0.06g and 150g, the weight ratio of polyoxyethylene-diethylenetriaminepentaacetic acid block polymer, IPDI, dibutyltin dilaurate and methylene chloride of terminal hydroxyl is 1: 0.106: 0.00459:11.49, reacted at 55°C for 5 hours under stirring to obtain 14.45 g of isocyanate-terminated polymer;

[0069] The second step hydroxy aldehyde compound is p-Hydroxybenzaldehyde, the polymer of terminal isocyanate group and the consumption of p-Hydroxybenzaldehyde are 14.45g and 0.7321g, ...

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Abstract

This invention relates to a chemical synthesis. It provides a polymer contrast agent for magnetic resonance imaging: end aldehyde group polyoxyethylene-diethylenetriamine pentaacetic acid block polymer. Its preparing process is: firstly, reacting diisocyanate and end hydroxy polyoxyethylene-diethylenetriamine pentaacetic acid to obtain end isocyanate group polyoxyethylene-diethylenetriamine pentaacetic acid block polymer; secondly, reacting said polymer and hydroxy aldehyde to obtain end aldehyde group polyoxyethylene-diethylenetriamine pentaacetic acid block polymer crude product; finally, purifying said end aldehyde group polyoxyethylene-diethylenetriamine pentaacetic acid block polymer. This has simple process and high yield; end aldehyde group polyoxyethylene-diethylenetriamine pentaacetic acid block polymer has amphipathy, innocuity, stable, low immunogenicity, good biocompatibility, multi-species, freely-soluble water, biodegradeable; it has advantanges high relaxation rate, freely-soluble water, clear imaging and little toxicity.

Description

technical field [0001] The present invention relates to a polyoxyethylene-diethylenetriaminepentaacetic acid block polymer containing aldehyde groups at the end, and the present invention further relates to the synthesis of the above-mentioned aldehyde-terminated polyoxyethylene-diethylenetriaminepentaacetic acid block polymer The method belongs to the fields of medical science and chemical synthesis technology. Background of the invention [0002] With the continuous development of medical science and technology, the use of magnetic resonance imaging to diagnose the location of lesions and determine the effect of treatment has become a method commonly used by doctors and acceptable to patients. But the problem it faces is how to improve the sensitivity of imaging and the definition of image. An effective way to solve this problem is to use MRI contrast agents, which need to be injected intravenously during MRI. Since the contrast agent directly ent...

Claims

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Application Information

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IPC IPC(8): C08G18/48C08G18/84C08G18/24
Inventor 宋春梅薛海丽庄小璐余亦华彭敏
Owner EAST CHINA NORMAL UNIV
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