Compounds, in particular peptides, compositions comprising them and cosmetic and dermo-pharmaceutical uses

• US 8,697,656 B2
• Filed: 01/15/2010
• Issued: 04/15/2014
• Est. Priority Date: 01/16/2009
• Status: Active Grant

• Current Assignee: Sederma, Co.
• Original Assignee: Sederma, Co.
• Inventors: Fournial, Arnaud, Mondon, Philippe, Peschard, Olivier
• Primary Examiner(s): Ha, Julie
• Assistant Examiner(s): KOMATSU, LI N
• Application Number:
  US13/144,614
• Publication Number:
  US 20120014887A1
• Time in Patent Office: 1,551 Days
• US Class Current: 514/21.9
• CPC Class Codes: A61K 38/06 Tripeptides
• CPC Class Codes: A61K 8/64 Proteins; Peptides; Derivatives or degradation products thereof
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: A61Q 19/06 for countering cellulitis
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations
• CPC Class Codes: A61Q 5/006 Antidandruff preparations
• CPC Class Codes: A61Q 7/00 Preparations for affecting hair growth
• CPC Class Codes: C07K 5/0815 with the first amino acid being basic

Abstract

The present invention concerns a peptide of following formula I: R being a side chain having at least one heteroatom selected from sulfur, nitrogen and oxygen in a carbonyl form (C═O); R₁ being either H or a lipophilic chain; R² being either OH or a lipophilic chain. More particularly the present invention concerns a cosmetic composition comprising a peptide as recited above and a physiologically acceptable medium. Results on the activity of the compounds are obtained and on the general state of the skin and its appendages, in particular via the stimulation of extracellular matrix components.

Claims

1. A peptide of following formula I:

2. The peptide according to claim 1, wherein R₁ is an acyl or sulfonyl group selected from a biotinoyl group or a group having an alkyl, aryl, aralkyl, sugar or alkoxy 1 to 24 carbon atom chain, said chain being linear, branched or cyclic, saturated or unsaturated, hydroxylated or non-hydroxylated, sulfur-containing or non-sulfur-containing.

3. The peptide according to claim 1, wherein R₂ is a —

O—

R₇ group or a —

NR₈R₉ group, R₇, R₈ and R₉ being independently from each other a hydrogen, an alkyl, aryl, aralkyl, acyl, sulfonyl, sugar or alkoxy of 1 to 24 carbon atoms chain, said chain being linear, branched or cyclic, saturated or unsaturated, hydroxylated or non-hydroxylated, sulfur-containing or non-sulfur-containing.

4. The peptide according to claim 1, wherein R₁ is a lipophilic chain and R₂ is OH.

5. The peptide according to claim 4, having the formula Pal-KMO₂K-OH, the methionine having a di-oxidized sulfur, wherein R₁ is palmitoyl and R₂ is OH.

6. A composition comprising the peptide of claim 1 and a physiologically acceptable medium.

7. The composition of claim 6 wherein said peptide is Pal-KMO₂K-OH.

8. The composition according to claim 6 further comprising a Portulaca pilosa plant extract, and wherein said extract is obtained using a method comprising a fatty ester.

9. The composition according to claim 6, wherein the proportion of peptide comprises between 0.00001% and 15% with regard to the total weight of the composition.

10. The composition of claim 9 wherein the proportion of peptide comprises between 0.001% and 5%.

11. A method to improve the general state of the skin and skin appendages comprising topically applying an effective amount of the composition of claim 6.

12. The method according to claim 11, wherein said improvement comprises treating intrinsic and extrinsic signs of skin aging selected from the group consisting of wrinkles, fine lines, discontinuities and roughness of the skin, skin sagging, skin spots and loss of brightness of complexion.

13. The method according to claim 11, wherein said improvement comprises improving mechanical properties of the skin selected from the group consisting of skin tonicity, skin firmness and skin elasticity.

14. The method according to claim 11 wherein said improvement comprises improving density of the dermis and epidermis, and giving or restoring volume to the dermis and epidermis.

15. The method according to claim 11 wherein said improvement comprises treating skin dehydration.