Pegylated 7-dehydrocholesterol derivative

A technology of PEGylation and dehydrocholesterol, applied in steroids, cosmetics, food science, etc., can solve the stagnation of 7-dehydrocholesterol research, structural denaturation, and no stability involved in the synthesis of 7-dehydrocholesterol sexual issues

Inactive Publication Date: 2016-11-30
HUMEDIX
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the research on the stabilization of 7-dehydrocholesterol has stagnated. The reason is that 7-dehydrocholesterol is easily converted into other substances under the influence of ultraviolet rays and temperature, and there is a reaction with oxygen in the air to occur Structural degeneration
[0010] In addition, as mentioned above, the existing patents only disclose the pharmaceutical stability of 7-dehydrocholesterol or studies showing cholecalciferol as an active form, but do not disclose the synthetic stability of 7-dehydrocholesterol

Method used

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  • Pegylated 7-dehydrocholesterol derivative
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  • Pegylated 7-dehydrocholesterol derivative

Examples

Experimental program
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Embodiment 1

[0152] Example 1: Preparation of mPEG350-S-DHC ester (compound of formula (1A), wherein R is methyl, X is O, n is 7.25 (average value), and m is 1)

Embodiment 1-1

[0153] Example 1-1: Preparation of 7-dehydrocholesterol succinate (compound of formula (5), wherein m is 1)

[0154]Dissolve 7-dehydrocholesterol (DHC) (6.45g, 16.8mmol) (6.45g, 16.8mmol) of chemical formula (4) in 120ml dichloromethane, wherein add triethylamine (3.39g, 33.5mmol) and 4-dimethylaminopyridine (0.82g , 6.7mmol) to obtain a solution. Therein, succinic anhydride (compound of formula (3), wherein m is 1) (3.35 g, 33.5 mmol) was added, followed by stirring at room temperature for 12 hours. The reaction solution was washed successively with 3.5% HCl aqueous solution, saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. Then, the organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 7.2 g of the target compound.

[0155] 1 H NMR 400MHz (CDCl 3 )δ5.59(dd,1H),5.41(dd,1H),4.75...

Embodiment 1-2

[0156] Example 1-2: Preparation of mPEG350-S-DHC ester (compound of chemical formula (1A), wherein R is methyl, X is O, n is 7.25 (average value), and m is 1)

[0157] Dissolve the 7-dehydrocholesterol succinate of embodiment 1-1 (the compound of chemical formula (5), wherein m is 1) (1.1g, 2.30mmol) and mPEG350-OH (chemical formula (6) in 10ml of dichloromethane A compound wherein R is methyl, n is 7.25 (mean), and X is O) (0.8 g, 2.30 mmol), to which 4-dimethylaminopyridine (0.42 g, 3.44 mmol) was added. To this, N-(3-dimethylaminopropyl)-N'-ethyl-carbodiimide (0.88 g, 4.59 mmol) was slowly added, followed by stirring at room temperature for 12 hours. The reaction solution was washed successively with 1.0N aqueous HCl solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. Then, the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to obtain 1.77 g o...

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Abstract

The present invention relates to a PEGylated 7-dehydrocholesterol derivative, and a composition for wrinkle alleviation and antiaging, containing the same. The PEGylated 7-dehydrocholesterol derivative, according to the present invention, has improved water solubility and stability, and thus can be effectively used, as an excellent vitamin D source, in a cosmetic composition, a pharmaceutical composition, a dietary supplement and the like for wrinkle alleviation and antiaging.

Description

technical field [0001] The present invention relates to PEGylated 7-dehydrocholesterol derivatives (Pegylated 7-dehydrocholesterolderivatives). More particularly, the present invention relates to PEGylated 7-dehydrocholesterol derivatives which have improved stability and solubility and are hydrolyzed in vivo to provide vitamin D, and also relate to wrinkle reduction and anti-aging containing Compositions of said PEGylated 7-dehydrocholesterol derivatives. Background technique [0002] There are two types of vitamin D, vitamin D 2 (calciferol) and vitamin D 3 (cholecalciferol, compound B), these two substances are metabolized in the liver and kidneys to their active form (calcitriol, compound C). 7-Dehydrocholesterol (7-DHC, Compound A) as Vitamin D 3 The provitamin form, which is converted to vitamin D by sunlight 3 . [0003] [0004] Usually, vitamin D 3 Promotes calcium absorption to strengthen bone density, so it is used as a treatment for osteoporosis and as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/00C07J41/0055A61P17/00A23L33/10A61K8/63A61Q19/00C07J9/005A23V2002/00A23V2200/318A61Q19/08
Inventor 郑凤烈房成植刘民志金明洙郑珉旭郑仁和金用洙
Owner HUMEDIX
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