Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
2001-05-21
2004-09-28
Weber, Jon P. (Department: 1651)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C424S063000
Reexamination Certificate
active
06797697
ABSTRACT:
BACKGROUND OF THE INVENTION
The darkening of skin color is a concern for many individuals. Most people obtain darker skin through exposure to UV light (e.g., suntanning or UV lamps). UV exposure, however, results in accelerated skin aging and increased incidence of skin cancer. The ability to generate a tanned appearance without incurring photodamage, thus, is important to many individuals. Accordingly, alternative methods for “sunless tanning” have evolved.
One method is the use of products containing dihydroxy acetone (DHA). Some of these products, however, produce color that is too orange and unnatural to the user. Moreover, the DHA-produced skin color only minimally protects the user from UV irradiation. Products containing beta-carotene and cantaxanthin have also been used to darken the skin. These products, however, also result in unnatural skin color and reduced sun-protection as compared to naturally tanned skin. Thus, a product is desired that could enhance the body's natural pigment content, resulting in a desired skin color and enhanced photo-protection, without the need of UV exposure.
SUMMARY OF THE INVENTION
The present invention relates to compositions containing a peptide(s) and a pigment(s) and the use thereof in darkening the skin.
Other features and advantages of the present invention will be apparent from the detailed description of the invention and from the claims
DETAILED DESCRIPTION OF THE INVENTION
It is believed that one skilled in the art can, based upon the description herein, utilize the present invention to its fullest extent. The following specific embodiments are to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention belongs. Also, all publications, patent applications, patents, and other references mentioned herein are incorporated by reference. Unless otherwise indicated, a percentage refers to a percentage by weight (i.e., % (W/W)).
Definitions
What is meant by “darkening the skin” is darkening the appearance of the skin, including, but not limited to, tanning the skin.
As used herein, “topical applying” means directly laying on or spreading on outer skin using, e.g., by use of the hands or an applicator such as a wipe, roller, or spray.
As used herein, “cosmetically-acceptable” means that the peptides, pigments, or inert ingredients which the term describes are suitable for use in contact with tissues (e.g., the skin) without undue toxicity, incompatibility, instability, irritation, allergic response, and the like.
As used herein, “safe and effective amount” means an amount of the peptide or composition sufficient to induce a darkening of the skin, but low enough to avoid serious side effects. The safe and effective amount of the compound or composition will vary with the area being treated, the age and skin type of the end user, the duration and nature of the treatment, the specific compound or composition employed, the particular cosmetically-acceptable carrier utilized, and like factors.
Pigment
What is meant by a “pigment” is a compound(s) that can be taken up by epidermal cells in the presence of the peptides described below, resulting in visually darker look to the skin. Examples of such pigments include, but not limiting to, melanin and melanin derivatives (e.g, both melanin polymers and lower molecular weight water-soluble melanin derivatives); extracts from natural sources containing pigments (e.g., brown pigments from plants from the Hedychium genus or Bearberry genus or yellow, orange and red pigments, from plants containing carotenoids or canthaxanthins); or synthetic chemicals such as compounds containing copper (e.g., copper salts such as CuCl
2
) or synthetic carotenoids or canthaxantins. What is meant by an “extract” is a mixture of compounds isolated from a natural source (e.g., a plant). Examples of synthetic melanin derivatives are disclosed in U.S. Pat. Nos. 5,618,519, 5,384,116, and 5,227,459. Examples of soluble melanin derivatives are disclosed in U.S. Pat. Nos. 5,744,125, 5,225,435, 5,218,079, and 5,216,116. Examples of commercially available soluble melanin derivatives include Melasyn-100™ from San-mar laboratories, Inc. (Elmsford, N.Y.) and MelanZe™ from Zylepsis (Ashford, Kent, United Kingdom).
The amount of pigment present in the composition will depend on the type of pigment used. The pigment typically will be present in the composition in an amount from about 0.001% to about 20% by weight, in particular in an amount from about 0.005% to about 5% by weight.
Peptides
The composition of the present invention comprises a peptide of the formula I
R
1
>Val—Gly—Val—Ala—Pro—Gly—R
3
Formula I
R
2
wherein:
each R
1
and R
2
, independently, is H, C
1-12
alkyl, C
7-10
phenylalkyl, or C(═O)E
1
, where E
1
is C
1-20
alkyl, C
3-20
alkenyl, C
3-20
alkynyl, phenyl, 3,4-dihydroxyphenylalkyl, naphthyl, or C
7-10
phenylalkyl; provided that when either R
1
or R
2
is C(═O)E
1
, the other must be H; and
R
3
is OH, NH
2
, C
1-12
alkoxy, C
7-10
phenylalkoxy, C
11-20
naphthylalkoxy, C
1-12
alkylamino, C
7-10
phenylalkylamino, or C
11-20
naphthylalkylamino;
or a cosmetically acceptable salt thereof;
In one embodiment, R
1
and R
2
, which are bound to the N-terminus of the peptide, are both H. In another embodiment, R
1
is H and R
2
is C(═O)E
1
(e.g., palmitoyl, oleatoyl, or stearatoyl).
Examples of peptides of the present invention include, but are not limited to, H
2
—Val—Gly—Val—Ala—Pro—Gly—NH
2
(Peptide 1, SEQ ID NO:1), H
2
—Val—Gly—Val—Ala—Pro—Gly—OH (SEQ ID NO:2), Palmitoyl—Val—Gly—Val—Ala—Pro—Gly—NH
2
(Peptide 1, SEQ ID NO:3), Palmitoyl—Val—Gly—Val—Ala—Pro—Gly—OH (SEQ ID NO:4), Stearatoyl—Val—Gly—Val—Ala—Pro—Gly—NH
2
(SEQ ID NO:5), and Stearatoyl—Val—Gly—Val—Ala—Pro—Gly—OH (SEQ ID NO:6), or a cosmetically-acceptable salt thereof.
The symbol A
1
, A
2
, or the like used herein (e.g., in Figure 1) stands for the residue of an alpha-amino acid. Such symbols represent the general structure, —NH—CH(X)—CO— or ═N—CH(X)—CO— when it is at the N-terminus or —NH—CH(X)—CO— when it is not at the N-terminus, where X denotes the side chain (or identifying group) of the alpha-amino acid, e.g., X is —CH(CH
3
)
2
for Val. Note that the N-terminus is at the left and the C-terminus at the right in accordance with the conventional representation of a polypeptide chain. R
1
and R
2
are both bound to the free nitrogen atom N-terminal amino acid (e.g., Val) and the R
3
is bound to the free carboxy group of the C-terminal amino acid (e.g., Gly).
Furthermore, where the amino acid residue is optically active, it is the L-form configuration that is intended unless the D-form is expressly designated. An alkyl group, if not specified, contains 1-12 carbon atoms.
The peptide of the invention can be provided in the form of cosmetically acceptable salts. Examples of preferred salts are those with therapeutically acceptable organic acids, e.g., acetic, palmitic, oleic, stearic, lactic, maleic, citric, malic, ascorbic, succinic, benzoic, salicylic, methanesulfonic, or pamoic acid, as well as polymeric acids such as tannic acid or carboxymethyl cellulose, and salts with inorganic acids such as the hydrohalic acids (e.g., hydrochloric acid), sulfuric acid or phosphoric acid.
The amount of peptide present in the composition will depend on the peptide used. The peptide typically will be present in the composition in an amount from about 0.001% to about 10% by weight, in particular in an amount from about 0.005% to about 5% by weight.
The method for synthesizing peptides of the present invention are well documented and are within the ability of a person of ordinary skill in the art. See, e.g., Bodanszky M, Int J Pept Protein Res 25(5):449-74 (1985), Fmoc Solid Phase Peptide Synthesis, eds. Chan, W. & White, P. (Oxford University Press, 2000), and Chemial Approaches to
Seiberg Miri
Shapiro Stanley S.
Johnson & Johnson Consumer Companies Inc.
McGowan William E.
Weber Jon P.
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