Asymmetric branched-chain degradable polyethylene glycol derivative

A polyethylene glycol, decomposable technology, which is applied in non-active ingredients medical preparations, peptides, organic chemistry, etc., can solve the problem of not involving polyethylene glycol derivatives, etc., to reduce impurities and inhibit cell vacuoles. Effect

Pending Publication Date: 2022-04-29
NOF CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far in this field, there is no report on branched-chain polyethylene glycol derivatives that inhibit cell vacuoles

Method used

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  • Asymmetric branched-chain degradable polyethylene glycol derivative
  • Asymmetric branched-chain degradable polyethylene glycol derivative
  • Asymmetric branched-chain degradable polyethylene glycol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0267] [chem 29]

[0268]

Embodiment 1-1

[0270] [chem 30]

[0271]

[0272] Average molecular weight = 20,000, "SUNBRIGHT MEH-20T" manufactured by NOF Corporation) (10 g) was dissolved in toluene (40 g), and after reflux dehydration at 110° C. for 1 hour, it was cooled to 40° C., and triethylamine ( 80 mg), methanesulfonyl chloride (84 mg), and reacted at 40° C. for 3 hours. After completion|finish of reaction, after diluting with toluene (100g), hexane (100g) was added, and it stirred at room temperature for 30 minutes, and deposited the product. Suction filtration was performed using 5A filter paper, and after recovering a deposit, it was dissolved in ethyl acetate (200g), and hexane (100g) was added, and it stirred at room temperature for 15 minutes, and deposited the product. Suction filtration was performed using 5A filter paper, and the precipitate was collected, washed with hexane (100 g), suction filtered using 5A filter paper, and vacuum-dried to obtain compound (p1). The yield was 8.9g.

[0273] 1 H-...

Embodiment 1-2

[0275] [chem 31]

[0276]

[0277]Glycine hydrochloride (5 g) was dissolved in ion-exchanged water (50 g). NaOH (3.0 g) was added to the aforementioned glycine aqueous solution, and the pH was adjusted to 10.8. Thereafter, the compound (p1) (8 g) obtained in Example 1-1 was added to the aforementioned aqueous solution, and the solution was reacted at 40° C. for 72 hours. After the reaction, the pH of the reaction liquid was neutralized to about 7 with hydrochloric acid solution. After neutralization, chloroform (50g) was added, and after stirring at room temperature for 15 minutes, the organic layer was collect|recovered. The organic layer was concentrated and dissolved in ethyl acetate (100 g), and hexane (50 g) was added, followed by stirring at room temperature for 15 minutes to precipitate a product. Suction filtration was performed using 5A filter paper, and the precipitate was collected, washed with hexane (50 g), suction filtered using 5A filter paper, and vacuum-...

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Abstract

Provided is a high-molecular-weight branched-chain degradable polyethylene glycol derivative that does not cause cell vesicles. A branched degradable polyethylene glycol derivative represented by formula (1), the branched degradable polyethylene glycol derivative having an oligopeptide that breaks down in a cell in the molecule. (In the formula, k1 and k2 are each independently 1-12, j1 and j2 are each independently 45-950, R is a hydrogen atom, a substituted or unsubstituted alkyl group having 1-12 carbon atoms, a substituted aryl group, an aralkyl group, or a heteroalkyl group, Z is an oligopeptide that can be decomposed by an enzyme in a cell, X is a functional group that can react with a biologically related substance, and L1 and L2 are each independently a single bond or a divalent spacer group.

Description

technical field [0001] The present invention relates to an intracellularly decomposed branched decomposable polyethylene glycol derivative used for modifying biologically related substances. Background technique [0002] Drugs obtained by using bio-related substances such as hormones, cytokines, antibodies, and enzymes are usually administered into a living body, and are rapidly removed from the living body by glomerular filtration in the kidney, and phagocytosis by macrophages in the liver or spleen, etc. was discharged. Therefore, the blood half-life is short and it is often difficult to obtain sufficient pharmacological effects. In order to solve this problem, attempts have been made to chemically modify bio-related substances with sugar chains, hydrophilic polymers such as polyethylene glycol, albumin, and the like. As a result, the blood half-life of bio-related substances can be extended by increasing the molecular weight, forming water and layers, and the like. In ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/065C07K1/107A61K47/60A61K47/64C08G65/333C08G81/00
CPCC07K5/06078A61K47/60A61K47/64C08G65/333C08G81/00C08G83/003A61K47/65C08G65/33324C08G2230/00A61K47/641
Inventor 羽村健吉冈宏树大坂间顺规西山伸宏
Owner NOF CORP
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