Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1998-12-04
2002-10-01
Hartley, Michael G. (Department: 1617)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C514S844000, C514S845000, C514S846000
Reexamination Certificate
active
06458371
ABSTRACT:
FIELD OF THE INVENTION
The invention refers to a cosmetic composition and a method for the prevention and/or reduction of the photoaging processes of the skin.
BACKGROUND OF THE INVENTION
Exposure of human skin to sunlight has several known unpleasant effects such as sunburn and carcinogenesis. Due to the ultraviolet radiation in sunlight, free radicals (e.g., hydroxy radicals or nascent oxygen) form in the skin. Such free radicals can injure the DNA of skin cells and contribute to photoaging of the skin.
Photoaging includes changes attributable to chronic sun exposure and results in dry skin, wrinkling, laxity or even a variety of benign neoplasms.
Free radicals having a powerful oxidizing effect can injure the membrane of cells by oxidizing the unsaturated fatty acid components of the membrane (peroxidization of lipids). Also, reactive aldehydes are formed during the oxidization. In the injury of the membrane, increased intake of calcium leads to cell death, and pathological processes are started due to the presence of the reactive aldehydes:
injury of DNA, resulting in mutation in both the cell nucleus and mitochondria;
changes in the properties of the interstitial proteins (i.e., elastin) owing to the formation of crosslinks.
It is known that the elastic structures of collagen proteins and elastin contain a lot of water. It is characteristic of the interstitial proteins that they are rich in lysine. The reactive aldehydes such as malondialdehyde result in condensation reactions with the protein side chains containing amino groups to yield crosslinks. Thus, the originally elastic structure of the skin becomes rigid and hydrophobic. During the above process, at first lipofuscin ceroids, then age pigments are formed.
The natural protective mechanisms against ultraviolet radiation include bronzing due to the formation of melanin, DNA repair mechanisms, etc. Deficiency of a protective mechanism such as DNA repair, with consequent loss of the correction of the DNA injuries caused by ultraviolet radiation leads to early photoaging of the skin. Xeroderma pigmentosum is a disease characterized by deficiency of DNA repair that can be accompanied by the development of a malignant tumor. Sunburn spots caused by bronzing in early childhood are photodamage that heals, leaving an extended scar that can result in spinocellular carcinoma or even in various malignant tumors (e.g., melanoma, cerato-acanthoma, basalioma, sarcoma).
Suntan compositions such as oils, creams or lotions containing UV light protective agents, if used, can eliminate sunburn. However, side effects like allergic contact dermatitis, photoallergic contact dermatitis, irritative dermatitis and photosensitivity are often experienced, especially on repeated use of the suntan compositions comprising a high amount of a UV light protective agent that either reflects or absorbs UV light. A further deficiency of the known suntan compositions is that they must be used before the UV exposure of the skin. After sunburn of an unprotected skin surface, the photodamage cannot be reduced by subsequent treatment of the exposed skin with the suntan composition.
Thus, there is an existing demand for a cosmetic composition that is efficient in both the prevention and the reduction of photoaging.
The hydroximic acid derivatives of Formula I below are known from Hungarian Patent No. 177 578 and its equivalent U.S. Pat. No. 4,308,399. The known compounds are suitable for the treatment of diabetic angiopathy.
Hungarian Patent No. 207 988 and its equivalent European Patent No. 417 210 and U.S. Pat. No. 5,296,606 describe related compounds, namely, hydroximic acid halides having a selective beta-blocking effect, thus being suitable for the treatment of diabetic angiopathy.
Hungarian Patent Application No. 2385/92 published under No. T/66350 describes further hydroximic acid derivatives. These known compounds can be used in the treatment of vascular deformations, mainly in the therapy of diabetes mellitus.
Only pharmaceutical compositions, for internal use, containing the hydroximic acid derivatives of Formula I have been described in the above literature.
Use of hydroximic acid compounds of Formula I for prevention or treatment of skin conditions is novel.
DESCRIPTION OF THE INVENTION
The invention refers to a cosmetic composition comprising a hydroximic acid derivative of the formula
wherein
R
1
is a hydrogen atom or a C
1-5
alkyl group;
R
2
is a hydrogen atom or a C
1-5
alkyl group, a C
5-7
cycloalkyl group or a phenyl group, optionally substituted by a hydroxy group; or
R
1
and R
2
together with the nitrogen atom to which they are attached form a 5 to 8 membered ring that optionally comprises one or more further nitrogen or oxygen atoms, wherein said ring can be optionally condensed with a benzene ring;
R
3
is a hydrogen atom, a phenyl group, a naphthyl group or a pyridyl group wherein said groups can optionally be substituted by one or more halo atoms or C
1-4
alkoxy groups;
A is a group of the formula
wherein
R
4
is a hydrogen atom or a phenyl group;
R
5
is a hydrogen atom or a phenyl group;
m has a value of 0, 1 or 2; and
n has a value of 0, 1 or 2; or a physiologically acceptable acid addition salt thereof as the active ingredient.
The aim of the invention is to provide a cosmetic composition and a method for the prevention and/or reduction of the photoaging processes of the skin.
“Prevention of the photoaging processes of the skin” means that practically no photodamage is experienced when, after treatment of the skin with a composition of the invention, the skin is exposed to UV light radiation of the usual intensity during sun-bathing.
“Reduction of the photoaging processes of the skin” means that a significantly lower rate of photodamage is observed on a skin surface treated with the composition of the invention after UV light exposure of the usual intensity during sun-bathing than on an untreated skin surface exposed to UV light of the same intensity.
It was found that the above aim is fulfilled by a cosmetic composition comprising a hydroximic acid derivative of the Formula I or a physiologically acceptable acid addition salt thereof as the active ingredient.
The term “composition” as used herein means a composition that is suitable for topical treatment and which is applied to the skin surface in a conventional manner.
The composition of the invention comprises a hydroximic acid derivative of Formula I or a physiologically acceptable acid addition salt thereof as the active ingredient in admixture with one or more conventional carriers of typical cosmetic compositions.
A C
1-5
alkyl group is, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl or n-pentyl group, preferably a methyl or an ethyl group.
A C
5-7
cycloalkyl group is a cyclopentyl, cyclohexyl, or cycloheptyl group, preferably a cyclopentyl or cyclohexyl group.
A 5 to 8 membered ring containing one or more heteroatoms can be, for example, a pyrrole, pyrazole, imidazole, oxazole, thiazole, pyridine, pyridazine, pyrimidine, piperidine, piperazine, morpholine, indole or quinoline ring.
A halo atom is, for example, a fluoro, chloro, bromo or iodo atom, preferably a chloro or a bromo atom.
The physiologically acceptable acid addition salts of the compounds of Formula I are the acid addition salts formed with physiologically acceptable inorganic acids, such as hydrochloric acid, sulfuric acid, etc., or with physiologically acceptable organic acids such as acetic acid, fumaric acid, lactic acid, etc.
A preferred subgroup of the compounds of Formula I consists of the hydroximic acid derivatives of Formula I wherein R
1
and R
2
together with the nitrogen atom to which they are attached for a piperidino group, R
3
is a pyridyl or a phenyl group and A represents a group of the formula b, wherein m and n have a value or 0. An especially preferred compound is the following: O-(3-piperidino-2-hydroxy-1-propyl)nicotinic amidoxime (Compound “A”).
The compounds of Formula I can be prepared by the processes known from Hungarian Patent No. 177 578 and its equivalen
Farkas Bea
Literati Nagy Peter
Vadasz Agnes
Vigh Laszlo
Birch & Stewart Kolasch & Birch, LLP
Hartley Michael G.
Medgene, Limited
Willis Michael A.
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