Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2001-12-27
2003-11-04
Dodson, Shelley A. (Department: 1773)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000
Reexamination Certificate
active
06641802
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Technical Field of the Invention
The present invention relates to novel amino acid compounds, to a process for the preparation thereof and to their use as photoprotecting UV screening agents, in particular when formulated as cosmetic compositions.
The present invention also relates to a regime/regimen employing the aforesaid novel compounds for the protection of the skin and/or hair against the deleterious effects of ultraviolet radiation and for the photoprotection of any other material or substrate which is sensitive to UV radiation (inorganic or organic glasses, plastics, foodstuffs, paints, etc.).
2. Description of the Prior Art
It is known to this art that light radiation of wavelengths of from 280 nm to 400 nm enables human skin to brown and that radiation of wavelengths of from 280 nm to 320 nm, known as UV-B radiation, causes erythemas and skin burns which can harm the development of natural tanning. For these reasons and also for aesthetic reasons, there exists a continual demand for means for controlling this natural tanning, for the purpose of thus controlling the color of the skin; it is thus advisable to screen out this UV-B radiation.
It is also known to this art that UV-A radiation, of wavelengths of from 320 nm to 400 nm, which causes the skin to brown, is apt to also effect a detrimental change therein, especially in the case of sensitive skin or skin which is continually exposed to solar radiation. In particular, UV-A radiation causes a loss of skin elasticity and the appearance of wrinkles, resulting in premature aging. It promotes the triggering of the erythemal reaction or accentuates this reaction in certain individuals and can even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and cosmetic reasons, such as preservation of the natural elasticity of the skin, for example, more and more individuals wish to control the effect of UV-A radiation on their skin. It is thus desirable to screen out the UV-A radiation as well.
Thus, for the purpose of providing protection of the skin and hair against all UV radiation which is as complete and as efficient as possible, sunscreen compositions are typically applied/administered that contain combinations of screening agents active in the UV-A region and screening agents active in the UV-B region.
Benzylidenecamphorsulfonamide compounds derived from amino acids are known to the prior art and, in particular, are described in U.S. Pat. No. 5,004,594 as UV screening agents, especially in the cosmetic field. Other sunscreens derived from amino acids, namely, amide compounds of para-methoxycinnamic acid and of urocanic acid, have also been described, in FR-2,579,461. These amino acid derivatives are capable of absorbing in the UV-B region and/or the UV-A region. They are soluble in those solvents conventionally employed in anti-sun/sunscreen formulations and, in particular, in oils. These exhibit no activity with regard to the scattering of light.
SUMMARY OF THE INVENTION
In the field of photoprotection, it has now surprisingly and unexpectedly been determined that certain amino acid compounds, insoluble or substantially insoluble in water and the conventional organic solvents, are capable both of absorbing and of scattering UV radiation in anti-sun/sunscreen formulations. Thus, the subject novel amino acid compounds in accordance with the invention provide a stronger photoprotection in comparison with the known amino acid derivatives.
The present invention thus features compositions well suited for photoprotecting a material/substrate sensitive to ultraviolet radiation, in particular to solar radiation, comprising an effective amount of at least one compound having the structural formula (I):
in which n is an integer ranging from 1 to 4; and R
1
is one of the following radicals of formula (1), (2), (3), (4), (5), (6) or (7):
in which p is an integer ranging from 1 to 3; R
2
is hydrogen, a C
1
-C
8
alkyl radical, a C
1
-C
8
O-alkyl radical, or a C
1
-C
8
O-acyl radical; R
3
and R
4
, which may be identical or different, are each H or halogen or C
1
-C
8
alkyl or alkoxy or a radical of the following formula (8):
R
5
is a hydrogen or halogen atom, a C
1
-C
8
alkyl or alkoxy radical, or a divalent radical:
R
6
is a hydrogen atom, a C
1
-C
8
alkyl radical or a divalent radical:
with the proviso that at least one of the two substituents R
5
and R
6
is the divalent radical:
R
7
is a C
1
-C
8
alkyl radical; and the acid or base salts thereof.
DETAILED DESCRIPTION OF BEST MODE AND SPECIFIC/PREFERRED EMBODIMENTS OF THE INVENTION
More particularly according to the present invention, when the sensitive material/substrate to be protected is human skin and/or hair, the subject compositions are provided in the form of cosmetic compositions comprising, formulated into a topically applicable, cosmetically acceptable vehicle, diluent or carrier therefor, an effective photoprotecting amount of at least one compound of formula (I).
The compounds of formula (I) in accordance with the invention can be provided in the form of a mixture of isomers or of a pure isomer (regio-, enantio- or geometric isomerism).
Exemplary preferred compounds of formula (I) are ornithine (n=3) derivatives and lysine (n=4) derivatives.
More particularly exemplary compounds of formula (I) in accordance with the invention are:
N
&egr;
-cinnamoyl-L-lysine;
N
&egr;
-(4-methoxycinnamoyl)-L-lysine;
N
&egr;
-[4-(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2ylidenemethyl) benzenesulfonyl]-L-lysine.
N
&egr;
-Cinnamoyl-L-lysine is described in the article “Syntheses of photosensitive poly(amino acids)”, Nasawa M. and Kamogawa H.,
Bulletin of the Chemical Society of Japan
, Vol. 48 (9), pages 2588-2591 (1975). 3-[(1-Oxo-3-phenyl-2-propenyl)amino]-L-alanine and its monohydrochloride have been described in the article “Structural determinants of inhibitory activity of N
3
(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid towards glucosamine-6-phosphate synthase”, Andruszkiewicz R.,
Polish J. Chem.,
67, pages 673-683 (1993).
Accordingly, this invention also features the novel amino acid compounds corresponding to the formula (I) as defined above, with the exception of N
&egr;
-cinnamoyl-L-lysine and of 3-[(1-oxo-3-phenyl-2propenyl)amino]-L-alanine and its monohydrochloride.
Too, the present invention features a process for the preparation of the novel compounds of formula (I) described above, comprising:
(a) in a first stage, complexing the NH
2
—CH(COOH)— moiety of an amino acid monohydrochloride having the following formula (II):
with a copper sulfate in a basic medium (for example, an aqueous sodium hydroxide solution) in the presence of a polar organic solvent (such as tetrahydrofuran, dimethylformamide or acetone);
(b) in a second stage, reacting, in the presence of a polar organic solvent, the copper complex thus obtained with an acid chloride R
1
COCl or a sulfonyl chloride R
1
SO
2
Cl, wherein R
1
is as defined above in the formula (I);
(c) in a third stage, recovering, by filtration, the precipitate obtained in stage (b); and
(d) decomplexing the product thus obtained with a sequestering agent (for example, ethylenediaminetetraacetic acid).
These amino acid derivatives are insoluble or substantially insoluble in water and in the conventional organic solvents usual in the cosmetics field, in particular oils.
By the term “insoluble or substantially insoluble compounds” are intended compounds having a solubility in water of less than 2% by weight, with a solubility in liquid petrolatum of less than 3% by weight and, finally, with a solubility in a mixture of triglyceride esters, such as “Miglyol 812”, marketed by Dynamit Nobel, of less than 5%, also by weight.
The amino acid compounds in accordance with the present invention can be reduced to a suitable particulate form by any ad hoc means, such as, in particular, dry milling or milling in a solvent medium, sieving, atomization, micronization or spraying. The mean size of the particles wil
Bordier Thierry
Philippe Michel
Burns Doane Swecker & Mathis L.L.P.
Dodson Shelley A.
Societe L'Oreal S.A.
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