Cosmetic Compositions Comprising at Least One Peptide with at Least One Immobilized Aromatic Cycle

• US 20110045036A1
• Filed: 05/04/2007
• Published: 02/24/2011
• Est. Priority Date: 05/05/2006
• Status: Active Grant

• Current Assignee: Sederma, Co.
• Original Assignee: Sederma, Co.
• Inventors: Lintner, Karl, Peschard, Olivier
• Granted Patent: US 8,507,649 B2
• Time in Patent Office: Days
• US Class Current: 424/401
• CPC Class Codes: A61K 38/08 Peptides having 5 to 11 amino acids A61K38/043 - A61K38/046 take precedence
• CPC Class Codes: A61K 8/64 Proteins; Peptides; Derivatives or degradation products thereof
• CPC Class Codes: A61P 17/16 Emollients or protectives, e.g. against radiation
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• 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 19/08 Anti-ageing preparations

Abstract

Topical cosmetic use as a whitening active ingredient of at least one peptide, comprising at least one blocked aromatic cycle and having the general formula (I): A-(Xa)m-Xc-(Xb)n-B. The invention also discloses a cosmetic composition comprising at least said peptide and a method of decreasing skin pigmentation, whitening or lightening human skin, comprising a topical application of said composition.

Claims

1-12. -12. (canceled)

13. A cosmetic composition comprising:

at least one peptide comprising at least one immobilized aromatic cycle of the formula (I);

A-(Xa)m-Xc-(Xb)n-B;

wherein

A is H, or an N-acyl group, selected from the group consisting of biotin or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or an alkoxy chain,

B is OR¹ or NR²R³, in which

R¹, R² and R³ are, independently of each other, H or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or alkoxy chain,

“

m” and

“

n”

are between 0 and 5 with the proviso that m+n≦

5,

(Xa) and (Xb) are amino acid residues, which may be the same or different, genetically encoded or not encoded, and (Xa)m and (Xb)n are chains from 0 to 5 amino acids (Xa1, Xa2, Xa3, Xa4, Xa5) (Xb1, Xb2, Xb3, Xb4, Xb5) which may be the same or different genetically encoded or not encoded, with the proviso that m+n≦

5,

Xc is an aromatic amino acid, wherein

if Xa1=His and n=0, then Xc is an amino acid residue selected from the group consisting of L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi, and Xa2 is not Ser, Ala, Phe or homoPhe;

if Xa1=L-Tyr, m≦

3 and n≦

1, then Xc is an amino acid residue selected among L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi; and

if Xa1 is not Tyr and not His, m+n≦

5, then Xc is an amino acid residue selected among L- or D-Tic, or L- or D-7-hydroxy-Tic, or L- or D-Tpi.

14. The cosmetic composition of claim 13, wherein if Xa1=His, then Xa2 is Leu.

15. The cosmetic composition of claim 13, wherein the peptide is selected from the group consisting of analogs or fragments of enkephalin or endothelin.

16. The cosmetic composition of claim 13, wherein the N-acyl group is selected from the group consisting of acetyl, palmitoyl, elaidoyl, myristoyl, biotinyl, and octanoyl.

17. A cosmetic composition comprising:

a dermatologically acceptable carrier, and

at least one peptide comprising at least one immobilized aromatic cycle of the formula (I);

A-(Xa)m-Xc-(Xb)n-B;

wherein

A is H, or an N-acyl group, selected from the group consisting of biotin or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or an alkoxy chain,

B is OR¹ or NR²R³, in which

R¹, R² and R³ are, independently of each other, H or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or alkoxy chain,

“

m” and

“

n”

are between 0 and 5 with the proviso that m+n≦

5,

(Xa) and (Xb) are amino acid residues, which may be the same or different, genetically encoded or not encoded, and (Xa)m and (Xb)n are chains from 0 to 5 amino acids (Xa1, Xa2, Xa3, Xa4, Xa5) (Xb1, Xb2, Xb3, Xb4, Xb5) which may be the same or different genetically encoded or not encoded, with the proviso that m+n≦

5,

Xc is an aromatic amino acid, wherein

if Xa1=His and n=0, then Xc is an amino acid residue selected from the group consisting of L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi, and Xa2 is not Ser, Ala, Phe or homoPhe;

if Xa1=L-Tyr, m≦

3 and n≦

1, then Xc is an amino acid residue selected among L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi; and

if Xa1 is not Tyr and not His, m+n≦

5, then Xc is an amino acid residue selected among L- or D-Tic, or L- or D-7-hydroxy-Tic, or L- or D-Tpi.

18. The cosmetic composition of claim 17, wherein said peptide is present at a concentration between 0.00001% (w/w) and 100% (w/w).

19. The cosmetic composition of claim 18, wherein said peptide is present at a concentration between 0.0001% (w/w) and 20% (w/w).

20. The cosmetic composition of claim 19, wherein said peptide is present at a concentration between 0.001% and 5% (w/w) by weight of the composition.

21. The cosmetic composition of claim 17, further comprising at least one skin care active or additional ingredient selected from the group consisting of skin depigmenting agent, skin whitening agent, lightening or bleaching agent, optical brightening agent, melanogenesis inhibitor agent, reducing pigmentation agent, keratolytic agent, desquamation agent, skin anti-aging agent, anti-wrinkle agent, anti-atrophy agent, anti-oxidant/radical scavenger, and mixtures thereof.

22. The cosmetic composition of claim 21, wherein the skin care active or additional ingredient is selected from the group consisting of a tyrosinase inhibitor, protein kinase A or C inhibitor, inhibitor of cellular calcium flux, inhibitor of adrenergic receptors α

or β

, hydroquinone, arbutin, kojic acid and its derivatives, vitamin C, vitamin E, vitamin A and their derivatives, boldine and its derivatives, licorice extract, citrus extract, bearberry extract, orange extract, lemon extract, cucumber extract, mulberry extract, rosemary extract, hops extract, mercaptosuccinic acid, mercaptodextran, glutathione, cysteine and its derivatives such as N-acetyl-L-cysteine, tocopherols, retinol, retinoic acid and retinaldehyde, and mixtures thereof.

23. The cosmetic composition of claim 17, which is in the form of a solution, dispersion, emulsion, paste, or powder, alone or in a premix;

in macrocapsules, microcapsules, or nanocapsules, macrospheres, microspheres or nanospheres, liposomes, oleosomes or chylomicrons, macroparticles, microparticles, or nanoparticles or macrosponges, microsponges or nanosponges;

or

adsorbed on organic polymer powders, talcs, bentonites, or other inorganic or organic supports.

24. The composition of claim 17, which is in the form of a cream, lotion, ointment, milk, gel, emulsion, dispersion, solution, suspension, cleanser, foundation, anhydrous preparation, body and bath oil, shower and bath gel, shampoo and scalp treatment lotion, cream or lotion for care of the skin or hair, sun-screen lotion, milk or cream, artificial suntan lotion, cream or milk, shaving cream or foam, aftershave lotion, make-up, mascara or nail varnish, lipstick, skin “

essence,”

serum, adhesive or absorbent material, transdermal patch, powder, emollient lotion, emollient milk, emollient cream, spray, foundation tint base, pomade, colloid, compact or solid suspension, pencil, sprayable formulation, or brossable.

25. A method of decreasing skin pigmentation, whitening or bleaching human skin, lightening skin complexion, attenuating senile lentigo, homogenizing skin color, preventing or reducing melanogenesis, reducing coloration on exposure to natural or artificial UV radiation, treating or preventing cutaneous hyperpigmentation, melasma, chloasma, or freckles comprising:

the step of applying to the skin of a human in need thereof, a safe and effective amount of at least one peptide comprising at least one immobilized aromatic cycle of the formula (I);

A-(Xa)m-Xc-(Xb)n-B;

wherein

A is H, or an N-acyl group, selected from the group consisting of biotin or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or an alkoxy chain,

B is OR¹ or NR²R³, in which

R¹, R² and R³ are, independently of each other, H or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or alkoxy chain,

“

m” and

“

n”

are between 0 and 5 with the proviso that m+n≦

5,

(Xa) and (Xb) are amino acid residues, which may be the same or different, genetically encoded or not encoded, and (Xa)m and (Xb)n are chains from 0 to 5 amino acids (Xa1, Xa2, Xa3, Xa4, Xa5) (Xb1, Xb2, Xb3, Xb4, Xb5) which may be the same or different genetically encoded or not encoded, with the proviso that m+n≦

5,

Xc is an aromatic amino acid, wherein

if Xa1=His and n=0, then Xc is an amino acid residue selected from the group consisting of L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi, and Xa2 is not Ser, Ala, Phe or homoPhe;

if Xa1=L-Tyr, m≦

3 and n≦

1, then Xc is an amino acid residue selected among L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi; and

if Xa1 is not Tyr and not His, m+n≦

5, then Xc is an amino acid residue selected among L- or D-Tic, or L- or D-7-hydroxy-Tic, or L- or D-Tpi.

26. The method of claim 25, wherein if Xa1=His, then Xa2 is Leu.

27. The method of claim 25, wherein the peptide is selected from the group consisting of analogs or fragments of enkephalin or endothelin.

28. The method of claim 25, wherein the N-acyl group is selected from the group consisting of acetyl, palmitoyl, elaidoyl, myristoyl, biotinyl, and octanoyl.

29. The method of claim 25, wherein said peptide is present at a concentration between 0.00001% (w/w) and 100% (w/w).

30. The method of claim 29, wherein said peptide is present at a concentration between 0.0001% (w/w) and 20% (w/w).

31. The method of claim 30, wherein said peptide is present at a concentration between 0.001% and 5% (w/w) by weight of the composition.

32. A method of reducing at least one sign of aging comprising the step of applying to a portion of human skin in need thereof, a safe and effective amount of at least one peptide comprising:

providing at least one peptide comprising at least one immobilized aromatic cycle of the formula (I);

A-(Xa)m-Xc-(Xb)n-B;

wherein

A is H, or an N-acyl group, selected from the group consisting of biotin or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or an alkoxy chain,

B is OR¹ or NR²R³, in which

R¹, R² and R³ are, independently of each other, H or an alkyl, aryl, aralkyl, acyl, alcohol, sulfonyl, sugar or alkoxy chain,

“

m” and

“

n”

are between 0 and 5 with the proviso that m+n≦

5,

(Xa) and (Xb) are amino acid residues, which may be the same or different, genetically encoded or not encoded, and (Xa)m and (Xb)n are chains from 0 to 5 amino acids (Xa1, Xa2, Xa3, Xa4, Xa5) (Xb1, Xb2, Xb3, Xb4, Xb5) which may be the same or different genetically encoded or not encoded, with the proviso that m+n≦

5,

Xc is an aromatic amino acid, wherein

if Xa1=His and n=0, then Xc is an amino acid residue selected from the group consisting of L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi, and Xa2 is not Ser, Ala, Phe or homoPhe;

if Xa1=L-Tyr, m≦

3 and n≦

1, then Xc is an amino acid residue selected among L- or D-Trp, L- or D-Phe, L- or D-Tyr, L- or D-Tic, L- or D-7-hydroxy-Tic, or L- or D-Tpi; and

if Xa1 is not Tyr and not His, m+n≦

5, then Xc is an amino acid residue selected among L- or D-Tic, or L- or D-7-hydroxy-Tic, or L- or D-Tpi; and

applying at least once a day for a period of time at least sufficient to provide a reduction in the visible signs of aging to the skin of a human in need thereof.

33. The method of claim 32, wherein if Xa1=His, then Xa2 is Leu.

34. The method of claim 32, wherein the peptide is selected from the group consisting of analogs or fragments of enkephalin or endothelin.

35. The method of claim 32, wherein the N-acyl group is selected from the group consisting of acetyl, palmitoyl, elaidoyl, myristoyl, biotinyl, and octanoyl.

36. The method of claim 32, wherein said peptide is present at a concentration between 0.00001% (w/w) and 1000 (w/w).

37. The method of claim 36, wherein said peptide is present at a concentration between 0.0001% (w/w) and 20% (w/w).

38. The method of claim 37, wherein said peptide is present at a concentration between 0.001% and 5% (w/w) by weight of the composition.