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Single active functional group-containing Y-type polyethylene glycol and preparation method thereof

A technology of active functional groups and polyethylene glycol, which is applied in the preparation of carriers for biomedical preparations, Y-type polyethylene glycol and its preparation, can solve the problems of inability to perform specific reactions, instability, and low drug coupling efficiency

Inactive Publication Date: 2013-01-30
XIAMEN SINOPEG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Second, it is unstable under alkaline conditions
[0007] Third, the coupling efficiency with drugs is low
However, the end groups of each arm in these multi-armed PEGs often contain the same hydroxyl functional group, which cannot react specifically

Method used

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  • Single active functional group-containing Y-type polyethylene glycol and preparation method thereof
  • Single active functional group-containing Y-type polyethylene glycol and preparation method thereof
  • Single active functional group-containing Y-type polyethylene glycol and preparation method thereof

Examples

Experimental program
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Effect test

preparation example 1

[0039] Preparation Example 1: Preparation of Compound 1

[0040] Under a nitrogen atmosphere, potassium hydride (200 mg, 5.0 mmol), tetrahydrofuran solution (40 mL), and 2-benzyloxyethanol (0.76 g, 5 mmol) were successively added to a 100 mL dry and clean double-necked round-bottom flask. Stir for four hours. Subsequently, ethylene oxide (30 g, 682 mmol) was added through a constant pressure dropping funnel in an anhydrous and oxygen-free system and reacted at room temperature for 24 hours. Then add excess bromoacetone glycalol to capping active oxygen anion, continue to react at 50 DEG C for 24 hours. The generated salt was separated by centrifugation, and then the solvent of the supernatant was evaporated by rotary evaporation, and precipitated in diethyl ether, and the precipitate was dried in a vacuum oven at 45° C. for 12 hours to obtain compound 1. Compound 1 1 H NMR is: 1 H NMR (CDCl 3 )δ(ppm): 1.42(-C(CH 3 ) 2 ), 3.43-3.83 (-CH 2 CH 2 O-, glycidol, -OCHCH 2 O...

preparation example 2

[0041] Preparation Example 2: Preparation of Compound 2

[0042] Add about 18.8g (Mn=6,000g / mol, 3.13mmol) of compound 1 (polyethylene glycol with end group protection) into a clean 250mL round bottom flask, and add 150mL THF to dissolve it, then add 13mL concentrated hydrochloric acid (Concentration is 37wt%), after stirring at room temperature for 6 hours, slowly add potassium hydroxide to adjust the pH value to 7.0, filter and separate the salt generated, and precipitate the solvent evaporated in the filtrate twice in ether, and the precipitate is at 45 After vacuum drying at °C for 12 hours, polyethylene glycol (compound 2) with two "active" hydroxyl groups at the end was obtained. Compound 2 1 H NMR is: 1 H NMR (CDCl 3 )δ(ppm): 1.42(-C(CH 3 ) 2 ), 3.43-3.84 (-CH 2 CH 2 O-, glycidol, -OCHCH 2 O-), 5.01 (-OCH 2 Ph), 7.16-7.23 (-C 6 h 5 ). The number average molecular weight was 6000. The molecular weight distribution was 1.01.

preparation example 3

[0043] Preparation Example 3: Preparation of Compound 3

[0044] Under a nitrogen atmosphere, potassium hydride (201 mg, 5.3 mmol), tetrahydrofuran solution (125 mL), and compound 2 (15 g, 2.5 mmol) were successively added to a 250 mL dry and clean double-neck round bottom flask, and stirred at room temperature for four hours. Subsequently, ethylene oxide (30 g, 682 mmol) was added through a constant pressure dropping funnel in an anhydrous and oxygen-free system and reacted at room temperature for 36 hours. Add excessive methyl iodide then and active oxygen anion is capped, continue to react at 50 ℃ for 24 hours. The generated salt was separated by centrifugation, and then the solvent of the supernatant was evaporated by rotary evaporation, and precipitated in diethyl ether, and the precipitate was dried in a vacuum oven at 45° C. for 12 hours to obtain compound 3. Compound 3 1 H NMR is: 1 H NMR (CDCl 3 )δ(ppm): 1.43(-C(CH 3 ) 2 ), 3.43-3.86 (-CH 2 CH 2 O-, glycidol, ...

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Abstract

The invention relates to a single active functional group-containing Y-type polyethylene glycol and a preparation method thereof. The single active functional group-containing Y-type polyethylene glycol is shown in a general chemical structural formula (1), wherein in the general chemical structural formula (1), n1, n2 and n3 respectively represent polymerization degrees of branch chains; number-average molecular weight of polyethylene glycol chain segments is in a range of 5000 to 100000; X represents a terminal active functional group of polyethylene glycol; R represents the same or different the same or different alkyl groups from alcohol compounds; and polyethylene glycol molecular weight distribution is in a range of 1.01 to 1.1. The invention also relates to a use of the single active functional group-containing Y-type polyethylene glycol in preparation of carriers for a biological medicinal preparation.

Description

technical field [0001] The invention relates to a novel Y-type polyethylene glycol and a preparation method thereof, in particular to a Y-type polyethylene glycol modified with a functional group at an end group, which has a single active functional group and a narrow molecular weight distribution. In addition, it also relates to the use of the Y-type polyethylene glycol in the preparation of carriers for biomedical preparations. Background technique [0002] Functionalized polyethylene glycol (PEG) can use its active groups to interact with drug molecules (including protein drugs and organic small molecule drugs), peptides, sugars, lipids, oligonucleotides, affinity ligands, Cofactors, liposomes, and biological materials are chemically coupled, and drug molecules are modified with polyethylene glycol, that is, PEGylation. After PEGylation, many excellent properties of PEG, such as hydrophilicity, flexibility, anticoagulation, etc., will also be transferred to the conjugate...

Claims

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Application Information

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IPC IPC(8): C08G65/337C08G65/333C08G65/334C08G65/28C08G65/338A61K47/34A61K47/48A61K33/24A61P35/00
Inventor 刘超翁文桂
Owner XIAMEN SINOPEG BIOTECH
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