Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2000-10-10
2002-12-17
Barts, Samuel (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S025000, C514S456000, C536S008000, C549S406000
Reexamination Certificate
active
06495524
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an external agent for the skin and a novel compound that is applicable thereto. More particularly, the present invention relates to an external agent for the skin that contains a compound having an inhibitory activity against melanine synthesis, that is excellent in the prevention and amelioration of skin pigmentation and that is suitable for cosmetics for whitening, and a novel compound having an inhibitory activity against melanine synthesis used preferably thereto.
BACKGROUND ART
Skin pigmentation that causes blotches, freckles, and blackening of the skin after sunburnt is attributed to considerable sthenia of melanine synthesis, which is in turn due to activation of melanocytes in the skin. This is one of problems concerning the skin of middle- to high-aged persons. Accordingly, in order to prevent or ameliorate such a trouble on the skin pigmentation, there have been known external agents far the skin that contain ascorbic acids, aqueous hydrogen peroxide, glutathione, colloidal sulfur, hydroquinone, cathecol or the like.
However, for the prevention and amelioration of skin pigmentation as described above, ascorbic acids tend to be oxidized and thus are unstable and causes discoloration in systems that contain much moisture, such as water-contained cosmetics. Also, aqueous hydrogen peroxide has the problems of stability during storage and safety while glutathione and colloidal sulfur give strong undesirable odors so that their use in products is restricted. Further, those additives such as hydroquinone and cathecol may have the problems of safety, such as skin irritation and allergy. Therefore, there has been currently obtained no external agent for the skin which is satisfactory in the prevention and amelioration of skin pigmentation. That is, there has been a need for a novel external agent for the skin that is safe and has an excellent whitening activity.
On the other hand, among compounds represented by formula (1) used for the external agent for the skin of the present invention, those in which R is a hydrogen atom are known compounds which are described in U. S. Pat. Nos. 2,418,458/1947 and 2,418,459/1947, and the like. Further, it is also known that inulavosin among these compounds has fish toxin activity and antibacterial activity, for example, that for
Staphylococcus aureus, Pseudomonas aeruginosa
, and the like (Heterocycles, Vol. 41, No. 9, 1923-1926 (1995)). However, it has not been known that the compounds represented by formula (I) inclusive of the above compounds have an inhibitory activity against melanine synthesis in skin. Further, it has not been reported that the compounds represented by formula (I) are used for an external agent for the skin to prevent and ameliorate of skin pigmentation.
DISCLOSURE OF THE INVENTION
Under the circumstances, the present invention has been made and an object of the present invention is to provide an external agent for the skin that not only exhibits excellent effects of prevention and amelioration of skin pigmentation but also has no fear of giving adverse influences to the skin and can be used safely.
The term “external agent for the skin” as used herein refers to a composition of any type of formula that can be administered to the skin and be pooled there continuously, used in a broad concept including cosmetics, quasi-drugs, external medicines for the skin and the like.
As a result of intensive investigation with a view to achieve the above-described object, the present inventors have discovered that compounds represented by formula (I), below have strong inhibitory activity against the melanine synthesis by live melanocytes and further that they exhibit excellent effects of prevention and amelioration of skin pigmentation when they are contained in a basic formulation of external agents for the skin. Also, the present inventors have newly produced the compounds having the above-described activity. Based on these, the present invention has been completed.
That is, the present invention relates to an external agent for the skin comprising one or more compound(s) selected from compounds represented by formula (I) below:
(wherein R
1
, R
2
, R
3
, R
4
, and R
5
, independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and R represents a hydrogen atom, an acyl group, or a sugar residue).
In a preferred embodiment of the external agent for the skin of the present invention, content of one or more compound(s) selected from the compounds represented by formula (I) ranges in an amount from 0.0045 to 10% by weight based on the total weight of the external agent. The external agent for the skin of the present invention is used advantageously as an external agent for the skin for whitening the skin.
Also, the present invention relates to a compound represented by formula (III) below:
(wherein R
1
, R
2
, R
3
, R
4
, and R
5
, independently represent a hydrogen atom or an alkyl group having to 4 carbon atoms; and R
7
, represents an acyl group or a sugar residue).
Hereafter, the present invention will be described in detail.
(1) Compound represented by formula (I) that is an essential component of the external agent for the skin of the present invention
The external agent for the skin of the present invention contains one or more compounds represented by formula (I) above as an essential component. In formula (I), R
1
, R
2
, R
3
, R
4
, and R
5
, independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms may be either of a straight or branched chain and specifically includes a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, or a tert-butyl group, and the like. Among these, a methyl group is particularly preferred.
In formula (I), R represents a hydrogen atom of a hydroxyl group or a substituent of the hydrogen atom of a hydroxyl group, more specifically an acyl group or a sugar residue. Specifically, the acyl group includes an acyl group represented by R
6
—CO—, wherein R
6
represents an alkyl group having 1 to 17 carbon atoms or an alkenyl group having one or two double bonds and 3 to 17 carbon atoms, and mare specifically an acetyl group, a pentanoyl group, an isooctanoyl group, a stearoyl group, an isostearoyl group, an oleoyl group, an octadecadienoyl and the like. The above-described sugar residue is not limited particularly and includes any sugar residue having a glucoside linkage terminal, wherein the sugar is a monosaccharide or disachharide that can be connected through a glucoside linkage. Specific examples thereof include a glucose residue, a xylose residue, a fructose residue, an arabinose residue, a rhamnose residue, a galactose residue, a sucrose residue, a maltose residue, and the like.
Further, among the compounds represented by formula (I) above, those compounds preferably used for external agent for the skin of the present invention include compounds represented by formula (II) below:
(wherein R represents a hydrogen atom, an acyl group represented by R
6
—CO— or a sugar residue; in which R
6
represents an alkyl group having 1 to 17 carbon atoms or an alkenyl group having one or two double bonds and 3 to 17 carbon atoms).
The compounds represented by formula (II) above are compounds represented by formula (I) in which R
1
, R
2
, R
3
, R
4
, and R
5
are each a methyl group. Further, as the acyl group or sugar residue represented by R in formula (II), there may be cited the same acyl group or sugar residue in the compounds represented by formula (I) above.
Among the compounds represented by formula (I) above, those in which R is a hydrogen atom are known compounds. Methods for their synthesis are described in U. S. Pat. Nos. 2,418,458/1947 and 2,418,459/1947. The above-described compounds produced by such methods can be used in the present invention.
Further, among the compounds represented by formula (II) that are used advantageously in the present invention, the compound in which R is a hydrogen atom
Hattori Takao
Ito Hideyuki
Katagiri Takayuki
Kitada Yoshio
Yoshida Takashi
Barts Samuel
Henry Michael C.
Knobbe Martens Olson & Bear LLP
Pola Chemical Industries Inc.
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