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Live target adjuvant containing D-galactose and sterol or aliphatic alcohol and its preparation

A technology of galactose and excipients, applied in the field of medicine, can solve the problems of complex reaction and low yield, and achieve the effect of easy degradation and short reaction process

Inactive Publication Date: 2007-02-14
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] With galactose or lactose as the reaction raw material, the hydroxyl group needs to be activated first to increase the degree of reaction, and the unreacted hydroxyl group needs to be protected, so the reaction is more complicated and the yield is low

Method used

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  • Live target adjuvant containing D-galactose and sterol or aliphatic alcohol and its preparation
  • Live target adjuvant containing D-galactose and sterol or aliphatic alcohol and its preparation
  • Live target adjuvant containing D-galactose and sterol or aliphatic alcohol and its preparation

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of [(2-lactose amido) ethylamino] cholesteryl formate (CH-ED-LA)

[0036] By synthesizing (2-aminoethylamino)cholesteryl formate and then reacting with lactobionolactone to obtain the target compound [(2-lactose amido)ethylamino]cholesteryl formate (CH-ED-LA). See attached figure 1 .

[0037] 1. Synthesis of lactobionolactone

[0038] Take lactobionic acid and add methanol to dissolve, evaporate under reduced pressure at 50°C, remove methanol, repeat 3-4 times, put the solid in an oven at 70-80°C for 48 hours, and obtain lactobionolactone.

[0039] 2. (2-Aminoethylamino) cholesteryl formate (I)

[0040] Take 0.45g cholesteryl chloromethyl ester (1mmol), with 60mL CH 2 Cl 2 Dissolved, placed in the dropping funnel, slowly added to the solution containing 5.84g ethylenediamine (100mmol) CH 2 Cl 2 solution, stirred and reacted in an ice-water bath for 10 hr. Evaporate CH under reduced pressure 2 Cl 2 , add 20mL of water (to wash away t...

Embodiment 2

[0043] Embodiment 2: (2-lactosamido) ethylamino] cholesteryl formate (CH-ED-LA) synthetic

[0044] By synthesizing N-(lactosyloxy) diimide, and then reacting with (2-aminoethylamino) cholesteryl formate to obtain [(2-lactose amido) ethylamino] cholesteryl formate (CH-ED- LA).

[0045] 1. Synthesis of lactobionic acid active ester

[0046] Dissolve 1.80 g of lactobionic acid (5 mmol) in 30 mL of DMF, cool to -15°C to -20°C, add 3.10 g of N,N'-dicyclohexylcarbodiimide (15 mmol), and stir at -15°C for 20 minutes. Rise to -5°C for 15 min, then add 1.15 g of N-hydroxysuccinimide (10 mmol), stir the reaction at -5°C for 1 h, and then stir at room temperature for 25 h. Filter the reaction mixture to remove dicyclohexyl urea, evaporate the obtained filtrate to about 5 mL, add 20 mL of absolute ethanol, add diethyl ether dropwise after ultrasonic dispersion, and precipitate white flocs, then filter with suction, wash with 2 mL of diethyl ether, and dry in vacuo. Obtain white powder ...

Embodiment 3

[0050] Example 3: Synthesis of [(2-lactosamido)hexylamino]cholesteryl formate (CH-HD-LA)

[0051] By synthesizing (2-aminohexylamino) cholesteryl formate and then reacting with lactobionolactone to obtain [(2-lactose amido) hexylamino) cholesteryl formate (CH-HD-LA).

[0052] Take 0.45g cholesteryl chloromethyl ester (1mmol), with 60mL CH 2 Cl 2 Dissolved, placed in the dropping funnel, slowly added to the solution containing 11.6g hexamethylenediamine (100mmol) 2 Cl 2 solution, stirred and reacted in an ice-water bath for 10 hr. Evaporate CH under reduced pressure 2 Cl 2 , add 20mL of water (to wash away the unreacted hexamethylenediamine and its hydrochloride), mix well, and then use CH 2 Cl 2(15ml×2) for extraction, washed with deionized water (15ml×2), and an appropriate amount of anhydrous Na 2 SO 4 Let dry overnight. The solvent was distilled off under reduced pressure to obtain 0.43 g of a gray solid (82.1% yield), TLC (dichloromethane / methanol=9:1); R f = 0....

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Abstract

A synthesis of the liver-target formate derivative containing galactose structure and its preparation containing said derivative are disclosed. Said derivative is prepared through the esterifying reaction sterol or emtrol and the compound containing lactose structure by di-primary amine compound in organic solvent other than water. It can modify the liposome, emulsion, milimicron vesicle (particle) and micelles to improve the liver-targeting performance.

Description

Technical field: [0001] The invention relates to the technical field of medicine, in particular to a class of liver-targeting adjuvants containing D-galactose and sterols or fatty alcohols and preparations thereof. Background technique: [0002] Hepatocellular carcinoma (HCC) is the most common malignant primary liver tumor, and HCC is not prevalent in most populations in the United States and Europe. But in many Asian and African countries, it is one of the three deadliest cancers. my country is a high-incidence area of ​​viral hepatitis, with an average annual incidence rate of 120-140 / 100,000, and about 280,000 people die of hepatitis-related diseases every year. There are 130 million hepatitis B virus carriers in my country, and the hepatitis B virus (HBV) infection rate is as high as 57.63%, that is, at least 600 million people in the country have been infected with HBV. The positive rate of HBsAg is 9.75%, about 120 million people, accounting for 1 / 3 of the world; ab...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K47/26A61K45/00C07J9/00A61K47/54
Inventor 邓意辉吴红兵王绍宁周新羽
Owner SHENYANG PHARMA UNIVERSITY
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