Stable peptide-conjugated ascorbic acid derivative, method for preparing same, and cosmetic composition comprising same

Patent metadata

Field	Value
Publication number	US-10239902-B2
Application number	US-201715606628-A
Country	US
Kind code	B2
Filing date	May 26, 2017
Priority date	Nov 27, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The present invention provides a stable peptide-conjugated, ascorbic acid derivative, a method for preparing the same, and a cosmetic composition comprising the same as an active ingredient. The stable peptide-conjugated ascorbic acid derivative of the present invention has both the effect of whitening the skin by inhibiting melanin production and the effect of reducing skin wrinkles by activating collagen production, and may be used in a cosmetic composition.

First claim

The invention claimed is:

1. A peptide-conjugated ascorbic acid derivative represented by the following formula I or a cosmetically acceptable salt thereof:

wherein

represents a peptide in which the same or different amino acid residues selected from among natural or non-natural amino acid residues are bonded by amide bonds;
R 1 represents side chains of the amino acid residues;
X is hydrogen or carbonyl (C═O);
R 2 is null when X is hydrogen, or R 2 is palmityl, lauryl or stearyl when X is carbonyl; and
n is an integer ranging from 2 to 5.

2. The peptide-conjugated ascorbic acid derivative or cosmetically acceptable salt thereof according to claim 1 , wherein

represents a peptide in which the same or different amino acid residues selected from among valine, lysine, glycine, arginine, aspartic acid, threonine and serine are bonded by amide bonds.

3. The peptide-conjugated ascorbic acid derivative or cosmetically acceptable salt thereof according to claim 2 , wherein n is an integer ranging from 3 to 5.

4. The peptide-conjugated ascorbic acid derivative or cosmetically acceptable salt thereof according to claim 1 , wherein

is selected from among lysine-valine-lysine and arginine-glycine-aspartic acid.

5. The peptide-conjugated ascorbic acid derivative or cosmetically acceptable salt thereof according to claim 4 , which is selected from among the following compounds:
(6S,9S,12S)-6,12-bis(4-aminobutyl)-9-isopropyl-5,8,11,14-tetraoxo-4,7,10,13-tetraazanonacosyl (5-((S)-1,2-dihydroxyethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl) hydrogen phosphate (I-1); and
(3S)-3-(2-((S)-2-amino-5-((diaminomethylene)amino)pentanamido)acetamido)-4-((3-((((5-((S)-1,2-dihydroxyethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)oxy)(hydroxy)phosphoryl)oxy)propyl)amino)-4-oxobutanoic acid (I-2).

6. A method for preparing a peptide-conjugated ascorbic acid derivative represented by formula I, the method comprising a step of subjecting a compound of the following formula II to a condensation reaction with a compound of the following formula IV, and then subjecting a product of the condensation reaction to a deprotection reaction if a protecting group is present in the product:

wherein

represents a peptide in which the same or different amino acid residues selected from among natural or non-natural amino acid residues are bonded by amide bonds;
R 1 represents side chains of the amino acid residues;
R 1 ′ is equal to R 1 or is R 1 in which amino group or carboxyl group is protected;
X is hydrogen or carbonyl (C═O);
R 2 is null when X is hydrogen, or R 2 is palmityl, lauryl or stearyl when X is carbonyl;
n is an integer ranging from 2 to 5.

7. A cosmetic composition, comprising (i) a peptide-conjugated ascorbic acid derivative represented by the following formula I or a cosmetically acceptable salt thereof and (ii) cosmetically acceptable base:

wherein

represents a peptide in which the same or different amino acid residues selected from among natural or non-natural amino acid residues are bonded by amide bonds;
R 1 represents side chains of the amino acid residues;
X is hydrogen or carbonyl (C═O);
R 2 is null when X is hydrogen, or R 2 is palmityl, lauryl or stearyl when X is carbonyl; and
n is an integer ranging from 2 to 5.

8. The cosmetic composition of claim 7 , which is for use of reducing skin wrinkles and whitening the skin.

9. The cosmetic composition of claim 7 , wherein the compound of formula I is comprised in an amount of 0.0001 to 2 wt % based on the total weight of the cosmetic composition.

Assignees

• Celltrion Inc

Inventors

• Park Young Jun
• Kim Jung Yun
• Jeong Jin Kyo
• Kim Hyeong Mi
• Cho Eun Joo
• Lim Joo Hyuck
• Song Hyun Nam
• Park Seon Kyung
• Moon Won Kang
• Chang Shin Jae
• Hong Seung Suh

Classifications

• A61Q19/08

  Anti-ageing preparations · CPC title

• A61K9/0014 Primary

  Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00) · CPC title

• C07K5/0817

  the first amino acid being Arg · CPC title

• C07F9/65515

  the oxygen atom being part of a five-membered ring · CPC title

• A61K47/14

  Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters · CPC title