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Method for producing polyethylene glycol having terminal carboxy group

A polyethylene glycol and production method technology, applied in the production field of polyethylene glycol with terminal carboxyl groups, to achieve the effect of inhibiting the increase of polydispersity

Active Publication Date: 2018-07-31
NOF CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in Jones oxidation, which is known as a typical oxidation method for alcohols, highly toxic chromium compounds are used
Therefore, in the case of producing a compound for a drug by Jones oxidation in order to remove a chromium compound, there is a problem that high-precision purification is required

Method used

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  • Method for producing polyethylene glycol having terminal carboxy group

Examples

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example

[0057] The present invention will be described more specifically with reference to examples. In addition, "%" hereinafter means "% by weight" unless otherwise specified.

[0058] The polydispersity and carboxylation rate of the polyethylene glycols obtained in Examples 1 to 2 and Comparative Examples 1 to 3 were calculated by using liquid chromatography (GPC and HPLC). As a system for liquid chromatography, Alliance manufactured by Waters Corp. was used.

[0059] The analysis conditions of GPC and HPLC are as follows.

[0060] GPC analysis

[0061] Detector: Differential refractometer

[0062] Columns: Ultrahydrogel 500 and Ultrahydrogel 250 (Waters Corp.)

[0063] Mobile phase: sodium acetate buffer (solvent: water, pH: 5.2)

[0064] Flow rate: 0.5ml / min

[0065] Sample volume: 5mg / mL, 20μL

[0066] Column temperature: 30°C

[0067] HPLC analysis

[0068] Detector: Differential refractometer

[0069] Column: Anion exchange column ES-502N (Asahipak)

[0070] Mobile ...

example 1

[0075] Sodium bicarbonate (0.27 g) was dissolved in ion-exchanged water (4.0 g) to obtain an aqueous sodium bicarbonate solution. Next, stir the double salt of potassium peroxymonosulfate, potassium bisulfate and potassium sulfate (0.25 g, content of potassium peroxymonosulfate=45% in the double salt, with respect to 1 mole of The amount of potassium persulfate of methoxypolyethylene glycol = 1.8 moles, produced by Tokyo Chemical Industry Co., Ltd.) and ethylenediaminetetraacetic acid (5.5 mg, 1.9 × 10 -5 Mole, manufactured by Kanto Chemical Co., Inc.). To the obtained suspension, an aqueous sodium bicarbonate solution was added dropwise to dissolve ethylenediaminetetraacetic acid, thereby obtaining an aqueous potassium peroxymonosulfate solution. Then, dissolve methoxypolyethylene glycol (2.0 g, 4.0×10 -4 Mole, weight average molecular weight = about 5,000, in formula (I), n = about 113, m = 2, SUNBRIGHT ME-050AL produced by NOF Corp.), obtained under a nitrogen atmosphere ...

example 2

[0080] Sodium bicarbonate (0.14 g) was dissolved in ion-exchanged water (2.0 g) to obtain an aqueous sodium bicarbonate solution. Next, stir the double salt (18 mg of potassium peroxymonosulfate, potassium bisulfate and potassium sulfate in ion-exchanged water (3.0 g), the content of potassium peroxymonosulfate=45% in the double salt, relative to 1 mole of Amount of potassium persulfate of methoxypolyethylene glycol = 1.6 mol, produced by Tokyo Chemical Industry Co., Ltd.) and ethylenediaminetetraacetic acid (0.4 mg, 1.3 x 10 -6 mole, produced by Kanto Chemical Co., Inc.). To the obtained suspension, an aqueous sodium bicarbonate solution was added dropwise to dissolve ethylenediaminetetraacetic acid, thereby obtaining an aqueous potassium peroxymonosulfate solution. Then, methoxypolyethylene glycol (1.0 g, 3.3×10 -5 Mole, weight average molecular weight=about 30,000, in formula (I), n=about 680, m=2, SUNBRIGHT ME-300AL produced by NOFCorp.), to the solution obtained under n...

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Abstract

Provided is a method for producing a polyethylene glycol having a terminal carboxy group without using an expensive reagent or a highly toxic heavy-metal compound and while suppressing an increase inpolydispersity. This method for producing a polyethylene glycol having a terminal carboxy group includes oxidizing, by using with potassium peroxymonosulfate, a polyethylene glycol represented by formula (I): CH3O(CH2CH2O)n(CH2)m-CHO at 5-40 DEG C in water of which the pH is adjusted to 6-8 using at least one selected from the group consisting of carbonates, phosphates, citrates, and acetates, toproduce a polyethylene glycol represented by formula (II): CH3O(CH2CH2O)n(CH2)m-COOH, wherein n represents a number of 10-1100, and m is 2 or 3.

Description

technical field [0001] The invention relates to a production method of polyethylene glycol with terminal carboxyl groups. Background technique [0002] In recent years, the development of pharmaceuticals using mediators such as hormones or physiologically active substances such as antibodies or enzymes as drugs has been actively carried out. When these substances are administered into the body, since they undergo phagocytosis by the reticuloendothelial system and excretion in the kidneys and are excreted from the body, retention in blood is low and sufficient drug effects cannot be obtained. Therefore, attempts have been made to improve drug retention in blood by modifying drugs with water-soluble polymers such as sugars or polyethylene glycol (PEG). It is known that modification with polyethylene glycol reduces the immunogenicity and antigenicity of the drug while maintaining the stability of the drug. In order to increase the uniformity of the drug (in particular, to sup...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/326
CPCC08G65/326C08G65/3322
Inventor 土井明子市川贵志竹花刚粒崎拓真
Owner NOF CORP
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