Hyaluronic acid derivative and therapeutic thereof

A technology of hyaluronic acid and its derivatives, which is applied in the field of medicine, can solve the problems of compound-related uses that have not been seen in literature and patent reports, and achieve the effects of long duration of drug effect, long retention time, and enhanced therapeutic effect

Active Publication Date: 2015-04-08
SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The compounds of the present invention and the

Method used

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  • Hyaluronic acid derivative and therapeutic thereof
  • Hyaluronic acid derivative and therapeutic thereof
  • Hyaluronic acid derivative and therapeutic thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of sinomenine-glycine-hyaluronic acid derivatives by hyaluronic acid tetrabutylammonium salt

[0025] (1) Preparation of N-tert-butoxycarbonylglycine (Boc-Gly): 2.3 g of glycine was weighed and dissolved in 20 ml of methanol. Weigh 6.96 g of di-tert-butyl dicarbonate (Boc anhydride) and dissolve it in 4.5 ml of methanol. Add the Boc anhydride methanol solution dropwise to the glycine solution under an ice bath, and simultaneously add 7 ml of 4M sodium hydroxide solution dropwise, and react at room temperature for 2 ~5h. TCL detection reaction to complete. Add 10ml of toluene and 3ml of concentrated hydrochloric acid, add an appropriate amount of ethyl acetate for extraction, add an appropriate amount of saturated brine to the organic layer, wash twice, remove the organic solvent by rotary evaporation, and obtain a colorless oil, add ethyl acetate-toluene for recrystallization, and obtain white needles. The solid was 4.48g, and the yield was 83.6...

Embodiment 2

[0033] Example 2: Preparation of sinomenine-glycine hyaluronic acid derivatives from hyaluronic acid sodium salt

[0034] Gly-SN was prepared by the same method as (1) and (2) in Example 1. Dissolve 1.50g HA (30W) in 80ml of water completely, add 0.85g of intermediate Gly-SN, 0.85g of EDCI, 0.52g of NHS, stir to dissolve and keep the pH between 4.2-5, react at room temperature for 20h, transfer the reaction solution to the dialysis bag , 0.9% NaCl dialyzed overnight, 5 times ethanol precipitation of the dialysate to obtain a white powder. The molar ratio of the 2-sugar units of the product hyaluronic acid to the molar ratio of sinomenine is 10:1.

Embodiment 3

[0035] Example 3: Preparation of sinomenine-aspartic acid-hyaluronic acid derivatives by hyaluronic acid tetrabutylammonium salt

[0036] By a method similar to that of Example 1, substituting aspartic acid for glycine, 3.1 g of the target compound powder was obtained. The molar ratio of the 2-sugar units of the product hyaluronic acid to the molar ratio of sinomenine is 6:1.

[0037] The structure of the product is shown in the following formula.

[0038]

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PUM

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Abstract

The invention discloses a hyaluronic acid derivative and a preparation method thereof, wherein the hyaluronic acid derivative is obtained via covalent combination of a phenolic hydroxyl group-containing isoquinoline compound with hyaluronic acid via intracorporal degradable molecular bridges. The hyaluronic acid derivative can be used for preparing medicines used for nonoral administration, and especially used for preparing slow-release medicines which are used for treating related diseases via articular cavity and eye posterior segment topical administration; and is excellent in curative effect; and toxic and side effect is less.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a hyaluronic acid derivative formed by covalently combining a compound containing a phenolic hydroxyl group with hyaluronic acid through a molecular bridge degradable in vivo and an application thereof. Background technique [0002] In recent years, with the rise and scale of natural herbal medicines in the world, the depth and breadth of their research have been strengthened day by day. Many monomeric compounds with biological activity have been isolated and purified, and their pharmacological effects have been further confirmed through experiments. A variety of monomeric compounds extracted from plants have been developed as oral or topical drugs, and the purity of some monomeric compounds has reached the level of injection, which can be used for intramuscular, joint cavity or intravenous administration, such as paclitaxel, artemisinin, sinomenine, Gastrodin, ginkgolide B, andrographolide...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K47/48A61K31/4725A61K31/485A61K31/4741A61K31/365A61P29/00A61P37/06
Inventor 陈建英刘杰李大伟张新房凌沛学张建强
Owner SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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