Topical composition

Abstract

This topical composition, characterized by containing one or more compounds selected from 5-deazaflavins represented by general formula (I), one or more compounds selected from glycyrrhizic acid and derivatives thereof, one or more compounds selected from panthenol and derivatives thereof, one or more compounds selected from allantoin and derivatives thereof, one or more compounds selected from β-glucan and derivatives thereof, one or more compounds selected from vitamin B3 and derivatives thereof, and γ-oryzanol, makes it possible to obtain cosmetics, drugs, quasi-drugs, and the like, intended for application to the skin, in which the effects of 5-deazaflavin compounds and the effects of specific compounds work synergistically. (In general formula (I): R1 represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, or a phenyl group; R2 represents an alkyl group, a cycloalkyl group, a phenyl-substituted lower alkyl group, a phenyl group, a phenyl group substituted with one of a halogen atom, a lower alkyl group, and a lower alkoxy group, or a lower alkyl di-substituted phenyl group; and R3 and R4 each represent a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a lower alkoxy group, a phenyl-substituted lower alkoxy, a lower alkylamino group, a phenyl-substituted lower alkylamino group, or a lower alkylsulfonyl group.)

Description

Skin external composition

[0001] This invention relates to a topical skin composition that is excellent in improving skin condition.

[0002] 5-Deazaflavins are a group of compounds that have a structure in which the nitrogen at the 5th position of the flavin skeleton is replaced with carbon. In the body, they act as coenzymes and are involved in a wide range of metabolic reactions, oxygen activation, and chemiluminescence, possessing diverse chemical properties.

[0003] The pharmacokinetics and chemical properties of 5-deazaflavin compounds are related to NAD (nicotinamide adenine dinucleotide). ＋ It is similar to FAD (flavin adenine dinucleotide) and activates intracellular energy production (ATP). Therefore, deazaflavin compounds are a key factor in the unique property of having a wide range of effects.

[0004] The present inventors have also found a 5-deazaflavin compound that is excellent in ATP activation in the mitochondrial complex and have filed a patent application (Patent Document 1).

[0005] Although this 5-deazaflavin compound has various effects and therefore has the potential to be applied to cosmetics, pharmaceuticals, quasi-drugs, etc., it has extremely low solubility, and there is a problem in that it is difficult to obtain the effects of the 5-deazaflavin compound even when it is incorporated into cosmetics, pharmaceuticals, quasi-drugs, etc. using conventional methods.

[0006] Therefore, there is a need for technologies that can fully obtain the effects of 5-deazaflavin compounds in cosmetics, pharmaceuticals, quasi-drugs, etc.

[0007] Patent No. 6717989

[0008] Therefore, the object of the present invention is to provide a technology that can fully obtain the effects of 5-deazaflavin compounds, particularly in cosmetics, pharmaceuticals, quasi-drugs, etc., for application to the skin.

[0009] As a result of diligent research to solve the above problems, the present inventors discovered that by combining a 5-deazaflavin compound with a specific compound, the effects of the 5-deazaflavin compound and the effects of the specific compound are synergistically exhibited, thus completing the present invention.

[0010] In other words, the present invention is as follows:

[0011] [1] The following general formula (I) (In the formula, R １ R represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, or a phenyl group. ２ R represents an alkyl group, a cycloalkyl group, a phenyl-substituted lower alkyl group, a phenyl group, a halogen atom, or a phenyl group substituted with one of a lower alkyl group or a lower alkoxy group, and a lower alkyldisubstituted phenyl group. ３ and R ４A topical skin composition characterized by containing one or more selected from 5-deazaflavin compounds represented by (wherein represents a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a lower alkoxy group, a phenyl-substituted lower alkoxy, a lower alkylamino group, a phenyl-substituted lower alkylamino group, or a lower alkylsulfonyl group), one or more selected from glycyrrhizic acid and its derivatives, one or more selected from panthenol and its derivatives, one or more selected from allantoin and its derivatives, one or more selected from β-glucan and its derivatives, one or more selected from vitamin B3 and its derivatives, and γ-oryzanol. [2] The topical skin composition according to [1] for improving skin condition. [3] The topical skin composition according to [1] or [2] which is an emulsified composition. [4] The topical skin composition according to [1] or [2] which is a liquid composition. [5] A skin external composition according to any one of [1] to [4], which is a gel-like composition. [6] A skin external composition according to any one of [1] to [4], which is an ointment-like composition. [7] A skin external composition according to any one of [1] to [4], which is a cream-like composition. [8] A skin external composition according to any one of [1] to [4], which is a powder-like composition. [9] A method for improving skin condition, characterized by applying a skin external composition according to any one of [1] to [8] to the skin.

[0012] The topical skin composition of the present invention, through a combination of a 5-deazaflavin compound and a specific compound, synergistically exhibits not only the effects of the 5-deazaflavin compound but also the effects of the specific compound.

[0013] Therefore, the topical skin composition of the present invention can be used to improve skin condition.

[0014] The topical skin composition of the present invention (hereinafter simply referred to as "the present invention composition") is the following general formula (I) (In the formula, R １ R represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, or a phenyl group. ２represents an alkyl group, a cycloalkyl group, a phenyl-substituted lower alkyl group, a phenyl group, a phenyl group substituted with one of a halogen atom, a lower alkyl group or a lower alkoxy group, or a lower alkyldisubstituted phenyl group, R ３ and R ４ represent a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a lower alkoxy group, a phenyl-substituted lower alkoxy, a lower alkylamino group, a phenyl-substituted lower alkylamino group, or a lower alkylsulfonyl group. A 5-deazaflavin (Pyrimido[4,5-b]quinoline-2,4(3H,10H)-diones) compound represented by the following formula: one or more selected from the group consisting of one or more selected from glycyrrhizic acid and its derivatives, one or more selected from panthenol and its derivatives, one or more selected from allantoin and its derivatives, one or more selected from β-glucan and its derivatives, one or more selected from niacinamide and its derivatives, and γ-oryzanol. In the present invention, the composition for external use on the skin refers to a composition applied to the skin. The method of applying to the skin is not particularly limited, and examples include methods of coating, spraying, and sticking.

[0015] In the composition of the present invention, one or more selected from 5-deazaflavin compounds can be used. Among the 5-deazaflavin compounds represented by the general formula (I), R １ is a methyl group, R ２ is an ethyl group, R ３ is a hydrogen atom, and R ４ is preferably a hydrogen atom (TND1128). This TND1128 is managed by Chemteras Co., Ltd. as TND1128JP and can be obtained from Chemteras Co., Ltd.

[0016] The content of one or more 5-deazaflavin compounds selected from the 5-deazaflavin compounds in the composition of the present invention is not particularly limited, but is, for example, 0.001 to 10% by mass (hereinafter simply referred to as "%"), preferably 0.005 to 5%, and more preferably 0.01 to 2%. In the composition of the present invention, the effect of the 5-deazaflavin compound begins to appear when the content of the 5-deazaflavin compound is greater than 0.001%, the effect of the 5-deazaflavin compound increases when the content is greater than 0.005%, and the effect of the 5-deazaflavin compound increases further when the content is greater than 0.01%.

[0017] One or more compounds selected from the above 5-deazaflavin compounds have effects such as regulating the oxidation-reduction state of the skin, maintaining an environment suitable for the expression of cellular functions, and improving the efficiency of skin function expression by participating in cellular metabolic activity and energy production.

[0018] The glycyrrhizic acid and its derivatives used in the composition of the present invention are not particularly limited, and examples include glycyrrhizic acid, dipotassium glycyrrhizate, trisodium glycyrrhizate, disodium glycyrrhizate, diammonium glycyrrhizate, and monoammonium glycyrrhizate. In the composition of the present invention, one or more selected from glycyrrhizic acid and its salts can be used, but the use of dipotassium glycyrrhizate is preferred.

[0019] The content of one or more glycyrrhizic acid derivatives selected from the composition of the present invention is not particularly limited, but is, for example, 0.001 to 5%, preferably 0.01 to 2%.

[0020] One or more of the above-mentioned glycyrrhizic acid and its derivatives have effects such as anti-inflammatory, redness suppression, and maintenance of skin condition.

[0021] Among the panthenol and its derivatives used in the composition of the present invention, panthenol is a precursor of D-pantothenic acid (vitamin B5). Examples of panthenol derivatives include pantothenic acid and pantothenyl ether. In the composition of the present invention, one or more selected from panthenol and its derivatives can be used, but the use of panthenol is preferred.

[0022] The content of one or more panthenol derivatives selected from the composition of the present invention is not particularly limited, but is, for example, 0.001 to 10%, preferably 0.01 to 4%.

[0023] The panthenol and its derivatives described above have moisturizing, anti-inflammatory, and skin function-supporting effects.

[0024] Among the allantoin and its derivatives used in the composition of the present invention, allantoin is C ４ H ６ N ４ O ３ It is a heterocyclic compound. Examples of allantoin derivatives include allantoin acetylmethionine and allantoin chlorohydroxyaluminum. In the composition of the present invention, one or more selected from allantoin and its derivatives can be used, but it is preferable to use allantoin.

[0025] The content of one or more allantoin derivatives selected from allantoin in the composition of the present invention is not particularly limited, but is, for example, 0.001 to 5%, preferably 0.01 to 2%.

[0026] The above-mentioned allantoin and its derivatives have effects such as anti-inflammatory, skin repair promotion, irritation relief, and protection.

[0027] Among the β-glucans and their derivatives used in the compositions of the present invention, β-glucans are polysaccharides linked in the β-form that are present in the cell walls of bacteria, fungi, and other fungi. These β-glucans can be obtained by known methods, commercially available products, etc., and are not particularly limited in their use. Examples of β-glucan derivatives include carboxymethyl-β-glucan sodium and phosphorylated β-glucan. In the compositions of the present invention, one or more of these β-glucans and their derivatives can be used, but the use of β-glucan is preferred.

[0028] The content of one or more β-glucans and their derivatives selected in the composition of the present invention is not particularly limited, but is, for example, 0.001 to 10%, preferably 0.01 to 2%.

[0029] The above-mentioned β-glucan and its derivatives have effects such as anti-inflammatory, moisturizing, repair-promoting, and maintenance of skin condition.

[0030] Among the vitamin B3 and its derivatives used in the composition of the present invention, examples of vitamin B3 include niacin and niacinamide. Examples of vitamin B3 derivatives include tocopherol nicotinate. In the composition of the present invention, one or more of vitamin B3 and its derivatives can be used, but it is preferable to use niacinamide.

[0031] The content of one or more vitamins selected from vitamin B3 and its derivatives in the composition of the present invention is not particularly limited, but is, for example, 0.001 to 20%, preferably 0.01 to 5%.

[0032] One or more of the above-mentioned vitamin B3 and its derivatives have effects such as improving the skin barrier, whitening the skin, and improving and maintaining the condition of the skin.

[0033] The γ-oryzanol used in the composition of the present invention is an antioxidant component derived from rice, and can be obtained by known methods, commercially available products, etc., without any particular limitations.

[0034] In the composition of the present invention, the content of γ-oryzanol is not particularly limited. For example, it is 0.001 to 5%, preferably 0.01 to 2%.

[0035] The above γ-oryzanol has effects such as suppressing oxidation and inflammation to protect the skin, whitening effect, and maintaining skin condition.

[0036] In the composition of the present invention, each component may be contained in the above content. However, for one or more selected from 5-deazaflavin compounds per mass 1, one or more selected from glycyrrhizic acid and its derivatives, one or more selected from panthenol and its derivatives, one or more selected from allantoin and its derivatives, one or more selected from β-glucan and its derivatives, one or more selected from vitamin B3 and its derivatives, and the total amount of γ-oryzanol, it is preferably 4 to 5500, more preferably 5 to 2000, and even more preferably 10 to 1000 from the viewpoint of effects.

[0037] By containing the above essential components, the composition of the present invention can improve the skin condition. Examples of the improvement of the skin condition include suppression of skin inflammation such as anti-inflammatory action and antioxidant action, protection action of the skin and improvement of its function, relaxation and protection from external stimuli, improvement of the skin barrier function such as an increase in the amount of moisture in the stratum corneum, prevention of rough skin, softening of the skin and cutin, improvement of sensitive skin, moisturization, relief and improvement of itching, anti-aging care of the skin, improvement of skin collagen production, improvement of skin metabolism, improvement of wound repair function, prevention and improvement of skin diseases such as acne and skin spots, alleviation of redness, improvement and enhancement of the color and texture of the skin, and the like. The composition of the present invention can be used for these uses to exhibit these effects.

[0038] In the above, the essential components in the composition of the present invention have been described. Needless to say, the effects can also be obtained by combining these components alone or in combination of 2 to 6 kinds with 5-deazaflavin compounds.

[0039] In addition to the essential components mentioned above, the composition of the present invention may contain other components as appropriate to suit various dosage forms, as long as the effects of the composition of the present invention are not impaired. The dosage forms that the composition of the present invention can take are not particularly limited and include, for example, liquid, gel, emulsion, semi-solid, solid, powder, aerosol, foam, and sheet forms. Specific dosage forms include emulsion compositions (W / O, O / W, O / W / O), liquid compositions, gel compositions, ointment compositions, cream compositions, powder compositions, as well as aerosol compositions (propellants, mists), foam compositions (mousse, foam), sheet compositions (face packs, etc.), wax compositions (wax), semi-solid compositions (balms, waxes, etc.), and solid compositions (sticks, bars, etc.).

[0040] When the composition of the present invention is used in the above dosage form, it can be manufactured according to conventionally known methods, except for the inclusion of the above-mentioned essential components.

[0041] The composition of the present invention may be used as a cosmetic, quasi-drug, pharmaceutical, etc., as appropriate. Note that some countries do not have a category equivalent to a quasi-drug. In such cases, it goes without saying that the category appropriate to that country will be applied.

[0042] The number of times the composition of the present invention is applied to the skin can be appropriately set according to the dosage form and purpose, but for example, if it is a liquid composition, 0.3 to 1.2 g, preferably 0.5 to 1.0 g, can be applied to the skin 1 to 4 times a day, preferably 2 to 3 times, preferably for several days to several months.

[0043] The present invention will be described in detail below with reference to examples of the present invention, but the present invention is not limited in any way to these examples.

[0044] Example 1 Preparation of topical skin composition: A topical skin composition was prepared according to the following formulation and manufacturing method. The numbers in the formulation indicate percentages.

[0045]

[0046] (Manufacturing method) After adjusting the particle size of 1 to 7, they were gradually added to 8 and mixed.

[0047] Test Example 1 Evaluation of Transepidermal Water Loss: Ten panelists applied 1 g of the topical skin composition of Example 1, Comparative Example 1, or Comparative Example 2 to the forearm skin twice a day, morning and evening, for two weeks. Transepidermal water loss (TEWL) was measured 30 minutes after the final application using a VAPOSCAN AS-VT200RS closed-chamber type water loss analyzer (Nippon Ash Co., Ltd.). The results are shown in Table 2.

[0048]

[0049] From the above results, the topical skin composition containing all of the following ingredients (Example 1: the amount of essential ingredients was half that of Comparative Examples 1 and 2) showed significantly reduced transepidermal water loss compared to the topical skin composition containing only the 5-deazaflavin compound (Comparative Example 1) and the topical skin composition containing dipotassium glycyrrhizate, panthenol, allantoin, β-glucan, niacinamide, and γ-oryzanol (Comparative Example 2).

[0050] Therefore, the topical skin composition of the present invention exhibits a remarkable barrier function improvement effect, suggesting a synergistic effect.

[0051] Test Example 2 Evaluation of Wound Healing Function: Tape stripping was performed 5 to 10 times on the forearms of three panelists using cellophane tape or keratin collection tape, and the redness and dryness of the forearms were visually checked immediately afterward. Subsequently, the topical skin composition of Example 1, Comparative Example 1, or Comparative Example 2 was applied to the forearm skin at a dose of 1 g twice a day, morning and evening, for two weeks. During the two weeks, the progress of wound recovery was observed, including redness, whitishness, roughness, wrinkles, and other visible signs of the wound on the forearms.

[0052] When Example 1 was applied, no redness was observed compared to when Comparative Examples 1 and 2 were applied, or when the area was untreated, and no white powdery discoloration was observed during the recovery process. On the other hand, when Comparative Examples 1 and 2 were applied, redness was present and a slight powdery discoloration was observed in each case.

[0053] Therefore, the topical skin composition of the present invention exhibits remarkable wound repair function, suggesting a synergistic effect.

[0054] Test Example 3: Evaluation of inflammation suppression: The right and left cheeks of three panelists were each divided into two fractions, for a total of four sections (upper right 1, upper left 2, lower right 3, lower left 4). Approximately 1 g of the topical skin composition of Example 1, Comparative Example 1, or Comparative Example 2 was applied to each section, and the progress of the subjects was observed.

[0055] The area in Example 1 showed less redness and fewer blemishes compared to the other areas (Comparative Example 1, Comparative Example 2, and untreated). The skin also felt smoother.

[0056] Therefore, the topical skin composition of the present invention exhibits a remarkable anti-inflammatory effect, suggesting a synergistic effect.

[0057] Example 2 Preparation of topical emulsified composition: A topical emulsified composition (O / W) was prepared according to the following formulation and manufacturing method.

[0058]

[0059] (Manufacturing method) Mix ingredients 7-9 together and gradually add them to ingredient 10 along with ingredients 1-6, then mix.

[0060] Example 3 Preparation of topical emulsified composition: A topical emulsified composition (W / O) was prepared according to the following formulation and manufacturing method.

[0061]

[0062] (Manufacturing method) Mix ingredients 1-6 and 9 and 10, then combine with 7 and mix into 8.

[0063] Example 4 Preparation of topical liquid composition: A topical liquid composition was prepared according to the following formulation and manufacturing method.

[0064]

[0065] (Manufacturing method) After adjusting the particle size of 1 to 7, they were gradually added to 8 and mixed.

[0066] Example 5 Preparation of topical gel composition: A topical gel composition was prepared according to the following formulation and manufacturing method.

[0067]

[0068] (Method) Dissolve ingredients 1-7 and 9 in ingredient 8 and mix.

[0069] Example 6 Preparation of topical ointment composition: A topical ointment composition was prepared according to the following formulation and manufacturing method.

[0070]

[0071] (Method) Mix ingredients 1-8 together by grinding them together.

[0072] Example 7 Preparation of topical cream composition: A topical cream composition was prepared according to the following formulation and manufacturing method.

[0073]

[0074] (Manufacturing method) Mix ingredients 9-11, then combine them with ingredients 1-7 and mix into ingredient 8.

[0075] Example 8 Preparation of topical powder composition: A topical powder composition was prepared according to the following formulation and manufacturing method.

[0076]

[0077] (Manufacturing method) 1 to 8 were mixed while adjusting the particle size.

[0078] The topical skin compositions prepared in Examples 2 to 8 all have the same effects as the topical skin composition prepared in Example 1.

[0079] The topical skin composition of the present invention can be used in cosmetics, pharmaceuticals, quasi-drugs, and the like.

Claims

1. The following general formula (I) (In the formula, R １ R represents a hydrogen atom, an alkyl group, a halogen-substituted alkyl group, a carboxy-substituted alkyl group, or a phenyl group. ２ R represents an alkyl group, a cycloalkyl group, a phenyl-substituted lower alkyl group, a phenyl group, a halogen atom, or a phenyl group substituted with one of a lower alkyl group or a lower alkoxy group, and a lower alkyldisubstituted phenyl group. ３ and R ４ A topical skin composition characterized by containing one or more 5-deazaflavin compounds represented by (where represents a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a lower alkoxy group, a phenyl-substituted lower alkoxy, a lower alkylamino group, a phenyl-substituted lower alkylamino group, or a lower alkylsulfonyl group), one or more selected from glycyrrhizic acid and its derivatives, one or more selected from panthenol and its derivatives, one or more selected from allantoin and its derivatives, one or more selected from β-glucan and its derivatives, one or more selected from vitamin B3 and its derivatives, and γ-oryzanol.

2. The topical skin composition according to claim 1, which is for improving skin condition.

3. The topical skin composition according to claim 1, which is an emulsified composition.

4. The topical skin composition according to claim 1, which is a liquid composition.

5. The topical skin composition according to claim 1, which is a gel-like composition.

6. The topical skin composition according to claim 1, which is an ointment-like composition.

7. The topical skin composition according to claim 1, which is a cream-like composition.

8. The topical skin composition according to claim 1, which is a powder composition.

9. A method for improving skin condition, characterized by applying a topical skin composition according to any one of claims 1 to 8 to the skin.

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