Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2000-10-24
2002-01-15
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C514S552000
Reexamination Certificate
active
06338854
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a photoaging inhibitor and a skin-care preparation and more particularly to a photoaging inhibitor comprising an aromatic compound derivative of triterpenoid and/or salts thereof and to a skin-care preparation which contains an aromatic compound derivative of triterpenoid and/or salts thereof and is excellent in the skin beautifying effect of preventing and ameliorating wrinkled skins.
BACKGROUND ART
Generally, by the term skin aging is meant a physiological phenomenon which involves a physiological aging with getting old and photoaging due to exposure to sunlight (ultraviolet rays) influencing each other. Currently, attention is being paid to relationship between the latter, i.e., photoaging, and wrinkled skin, rough skin, spots, and the like. That is, it has been known that continued exposure to sunlight (ultraviolet rays) increases deep wrinkles in the face or neck and further renders the skin dry and rough, and causes pigment deposition such as spots, freckles, and the like. Therefore, troubles in the skin due to photoaging has become an issue.
Hitherto, in order to prevent the damages to the skin due to ultraviolet rays, cosmetics (sun-screen or sun-protecting cosmetics) containing various ultraviolet absorbents, scattering or shielding agents, such as titanium oxide, zinc oxide, p-methoxycinnamic acid esters, p-aminobenzoic acid esters, and the like, have been developed and put into use. However, it is difficult to protect the skin from abundant exposure to sunlight despite the use of such cosmetics. Further, it has been known that external application of all trans-type retinoic acid is effective as a method of improving the above-described photoaging (see Methods in Enzymology, Vol. 190, p. 352-360 (1990)). However, use of this method is open only to doctors from the viewpoint of safety so that there has been demanded a development of a photoaging inhibitor and skin-care preparations which are highly effective and safe.
Accordingly, in order to meet the above-described demand, there have been used triterpenoids from plant origins, such as ursolic acid and oleanolic acid, or their derivatives such as esters, in photoaging ameliorating agents, cosmetics, externally applied skin agents and the like. However, triterpenes used as raw materials for these substances are very low in their content in plants so that there occur problems that blending them in amounts which assure sufficient effects is expensive and that it is difficult to assure a sufficient supply of them. Therefore, there has been a demand for the development of triterpenoid compounds that can exhibit sufficient effects in small amounts among the triterpenoid compounds which are highly safe, have photoaging preventing and ameliorating effect and are excellent in the skin beautifying effect.
DISCLOSURE OF THE INVENTION
The present invention has been completed from the above-described viewpoints and an object of the present invention is to provide a photoaging inhibitor comprising a triterpenoid compound which is highly safe and excellent in photoaging inhibiting effect and another object of the present invention is to provide a skin-care preparation which is excellent in the skin beautifying effect such as preventing and ameliorating wrinkled skin and the like.
As a result of intensive investigation with a view to solving the above-described problems, the present inventors have found that among triterpenoid derivatives which derived by substituting a functional group for a hydrogen atom in a carboxyl group at the 28-position and/or a hydrogen atom in a hydroxyl group bonded to a carbon atom at the 3-position of ursolic, oleanolic or betulic acid, those which derived by substituting a functional group having an aromatic ring for at least one of the above-described hydrogen atoms (hereafter, sometimes referred to as “aromatic compound derivative of triterpenoid”) and salts thereof have a physiological activity by at least 10 times as potent in the effect of inhibiting or ameliorating photoaging of skin as triterpenoids such as ursolic acid, oleanolic acid, and betulic acid, and their aliphatic acyl derivatives and aliphatic ester derivatives hitherto reported and further that skin-care preparations containing the above-described aromatic compound derivative of triterpenoid and/or salts thereof are excellent in the skin beautifying effect such as preventing and ameliorating wrinkled skin and the like, thus completing the present invention.
That is, the present invention provides a photoaging inhibitor comprising one or more compounds selected from triterpenoid derivatives and salts thereof, wherein the triterpenoid derivatives are derived by substituting a functional group for a hydrogen atom in a carboxyl group at the 28-position and/or a hydrogen atom in a hydroxyl group bonded to a carbon atom at the 3-position of ursolic, oleanolic or betulic acid, wherein at least one of the functional groups is a functional group having an aromatic ring.
As the compound which can be used as the photoaging inhibitor of the present invention is specifically those in which the functional group having an aromatic ring is a group represented by general formula (I) below when it is a substituent group for the hydrogen atom in the carboxyl group at the 28-position, or a group represented by general formula (I) or (II) below when it is a substituent group for the hydrogen atom in the hydroxyl group bonded to the carbon atom at the 3-position:
wherein, in the above formula (I), R
1
represents a substituted or unsubstituted aromatic ring , and R
2
represents a hydrogen atom or a substituted or unsubstituted aromatic ring,
wherein, in the above formula (II), R
3
represents a substituted or unsubstituted aromatic ring, and n represents 0 or an integer of up to 2.
More specific compounds include those triterpenoid derivatives and salts thereof, wherein in the general formula (I), the R
1
represents a phenyl group, a methoxyphenyl group, an ethoxyphenyl group, a butoxyphenyl group, a nitrophenyl group, a diphenyl group, or a naphthyl group and R
2
represents a hydrogen atom or a phenyl group, and the R
3
in the general formula (II) represents a phenyl group, a methoxyphenyl group, an ethoxyphenyl group, a butoxyphenyl group, a nitrophenyl group, a diphenyl group, or a naphthyl group.
Further, the present invention provides a skin-care preparation containing one or more compounds selected from triterpenoid derivatives and salts thereof, wherein the triterpenoid derivatives are derived by substituting a functional group for a hydrogen atom in a carboxyl group at the 28-position and/or a hydrogen atom in a hydroxyl group bonded to a carbon atom at the 3-position of ursolic, oleanolic or betulic acid, wherein at least one of the functional groups is a functional group having an aromatic ring. The aromatic compound derivative of the triterpenoids and/or salts thereof to be contained in the skin-care preparation specifically include compounds similar to the aromatic compound derivative of the triterpenoids and/or salts thereof that constitute the above-described photoaging inhibitor. A specific example of the content of the aromatic compound derivative of the triterpenoids and/or salts thereof in the skin-care preparation of the present invention is from 0.0001 to 10% by weight based on the total amount of the preparation.
Hereafter, the present invention will be described in detail. First, the photoaging inhibitor of the present invention will be explained.
(1) Photoaging Inhibitor of the Present Invention
The photoaging inhibitor of the present invention comprise one or more compounds selected from triterpenoid derivatives and salts thereof, wherein the triterpenoid derivatives are derived by substituting a functional group for a hydrogen atom in a carboxyl group at the 28-position and/or a hydrogen atom in a hydroxyl group bonded to a carbon atom at the 3-position of ursolic, oleanolic or betulic acid, wherein at least one of the functional groups is a functional group having an aromati
Fujiwara Norio
Kenjo Yukiko
Matsumoto Katsuo
Nishimori Yasutomo
Tsuruoka Hiroki
Dodson Shelley A.
Knobbe Martens Olson & Bear LLP
Pola Chemical Industries Inc.
Williamson Michael A.
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