JP2016008204A - External preparation for skin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide anti-inflammatory agents, moisturizing agents, therapeutic agents and external preparations for atopic dermatitis which contain a vitamin B6 derivative and give a sufficient effect to skin inflammation and dryness without causing skin irritation.SOLUTION: The invention relates to anti-inflammatory agents, moisturizing agents, therapeutic agents and external preparations for atopic dermatitis which contain the compound represented by formula (1), or a salt thereof. (Where, Rrepresents a glycosyl group, a phosphate group, or a cyclic phosphoric acid group bound to R; Rrepresents a -CHOH, -CHO, -CHNH, -CH-amino acid residue or -CH-OPOH; and Rrepresents a hydrogen atom or -POH.)

Description

  The present invention relates to an external preparation for skin.

  Pyridoxine, pyridoxal, and pyridoxamine are both substances having vitamin B6 action, together with pyridoxine 5'-phosphate, pyridoxal 5'-phosphate and pyridoxamine 5'-phosphate, which are phosphate esters at the 5 'positions, respectively. It is called vitamin B6 group. These compounds are metabolized in the body to pyridoxal 5'-phosphate and play an important role as a coenzyme for enzymes involved in amino acid metabolism.

  Pyridoxine and its hydrochloride are known to be very unstable to light, and pyridoxal, pyridoxamine and pyridoxal 5'-phosphate are also very unstable to light.

  On the other hand, vitamin B6 derivative having a specific structure obtained by glycosylation, phosphate esterification or sulfate esterification at the 3-position of vitamin B6 is excellent in stability, and in particular, the stability to light is remarkably improved. It became clear in recent years (refer patent document 1). Patent Document 2 discloses a cosmetic containing this vitamin B6 derivative and describes that it exhibits a whitening effect, an antiaging effect, a wrinkle suppressing effect, and the like.

Japanese Patent No. 4680775 Japanese Patent No. 4533415

  Vitamin B6 is a vitamin that plays an important role in the metabolism of proteins in the body, and also acts as a coenzyme in the metabolism of fat. If it is deficient, it causes skin inflammation, swelling, hair loss, etc. (Fragrance Journal, 17 (3) 96-100 (1986), JP 2002-265368 A). As an external preparation for skin, an external preparation containing a vitamin B6 derivative such as pyridoxine hydrochloride has been conventionally used for the treatment and prevention of skin irritations, acne, sunburn, hot flash caused by snow burn, itching due to inflammation, and dandruff due to dry seborrhea. Has been. However, conventionally used vitamin B6 derivatives have poor light stability and have problems such as skin irritation observed in their degradation products, and even when used in a skin external preparation, vitamin B6 There is a problem that sufficient effects cannot be obtained.

  In addition to the above-mentioned skin roughness and acne, shaving such as shaving and hair removal may cause skin irritation, dryness, and the like. Furthermore, when a steroid-based external preparation that has been conventionally used for the treatment of dermatitis is used, there is a problem that the skin dries. Therefore, an excellent moisturizing component that can be added to the external preparation is expected.

  The present invention has been made in view of the above circumstances, and contains an anti-inflammatory agent, a moisturizing agent, and atopy, which contains a vitamin B6 derivative, has no skin irritation, and has a sufficient effect on skin inflammation and drying. An object of the present invention is to provide a therapeutic agent for dermatitis and an external preparation.

  As a result of intensive studies to solve the above problems, the present inventors have newly found that the compound represented by the formula (1) which is a vitamin B6 derivative or a salt thereof suppresses inflammation and dryness of the skin. The headline and the present invention have been completed.

（式中、Ｒ^１はグリコシル基、リン酸基、又はＲ^２と結合した環状リン酸基を示し、Ｒ^２は−ＣＨ_２ＯＨ、−ＣＨＯ、−ＣＨ_２ＮＨ_２、−ＣＨ_２−アミノ酸残基、又は−ＣＨ_２−ＯＰＯ_２Ｈを示し、Ｒ^３は水素原子又は−ＰＯ_３Ｈ_２を示す。）
［２］髭剃り又は脱毛に起因する炎症に対する、［１］の抗炎症剤。
［３］式（１）で表される化合物がピリドキシン３，４’−環状リン酸である、［１］又は［２］の抗炎症剤。
［４］式（１）で表される化合物又はその塩を含有する保湿剤。

（式中、Ｒ^１はグリコシル基、リン酸基、又はＲ^２と結合した環状リン酸基を示し、Ｒ^２は−ＣＨ_２ＯＨ、−ＣＨＯ、−ＣＨ_２ＮＨ_２、−ＣＨ_２−アミノ酸残基、又は−ＣＨ_２−ＯＰＯ_２Ｈを示し、Ｒ^３は水素原子又は−ＰＯ_３Ｈ_２を示す。）
［５］髭剃り又は脱毛に起因する乾燥に対する、［４］の保湿剤。
［６］式（１）で表される化合物がピリドキシン３，４’−環状リン酸である、［４］又は［５］の保湿剤。
［７］式（１）で表される化合物又はその塩を含有するアトピー性皮膚炎の治療剤。

（式中、Ｒ^１はグリコシル基、リン酸基、又はＲ^２と結合した環状リン酸基を示し、Ｒ^２は−ＣＨ_２ＯＨ、−ＣＨＯ、−ＣＨ_２ＮＨ_２、−ＣＨ_２−アミノ酸残基、又は−ＣＨ_２−ＯＰＯ_２Ｈを示し、Ｒ^３は水素原子又は−ＰＯ_３Ｈ_２を示す。）
［８］式（１）で表される化合物がピリドキシン３，４’−環状リン酸である、［７］の治療剤。
［９］ステロイドと式（１）で表される化合物又はその塩とを含有する外用剤。

（式中、Ｒ^１はグリコシル基、リン酸基、又はＲ^２と結合した環状リン酸基を示し、Ｒ^２は−ＣＨ_２ＯＨ、−ＣＨＯ、−ＣＨ_２ＮＨ_２、−ＣＨ_２−アミノ酸残基、又は−ＣＨ_２−ＯＰＯ_２Ｈを示し、Ｒ^３は水素原子又は−ＰＯ_３Ｈ_２を示す。）
［１０］式（１）で表される化合物がピリドキシン３，４’−環状リン酸である、［９］の外用剤。 That is, the present invention provides the following [1] to [10].
[1] An anti-inflammatory agent comprising a compound represented by the formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )
[2] The anti-inflammatory agent of [1] against inflammation caused by shaving or hair loss.
[3] The anti-inflammatory agent according to [1] or [2], wherein the compound represented by the formula (1) is pyridoxine 3,4′-cyclic phosphate.
[4] A humectant containing the compound represented by the formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )
[5] The humectant according to [4] against drying due to shaving or hair removal.
[6] The humectant according to [4] or [5], wherein the compound represented by the formula (1) is pyridoxine 3,4′-cyclic phosphate.
[7] A therapeutic agent for atopic dermatitis containing a compound represented by the formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )
[8] The therapeutic agent according to [7], wherein the compound represented by the formula (1) is pyridoxine 3,4′-cyclic phosphate.
[9] An external preparation containing a steroid and a compound represented by the formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )
[10] The external preparation of [9], wherein the compound represented by the formula (1) is pyridoxine 3,4′-cyclic phosphate.

  According to the present invention, it is possible to provide an anti-inflammatory agent, a moisturizer, a therapeutic agent for atopic dermatitis and an external preparation containing a vitamin B6 derivative. The present invention can also provide an anti-inflammatory agent and a humectant containing a vitamin B6 derivative, which are used to prevent or ameliorate inflammation and dryness caused by shaving.

FIG. 1 is a diagram showing the change over time when scoring the degree of skin irritation due to shaving when the gel cream of Example 1 or Comparative Example 1 was used and when it was not treated. The section at the top of the figure shows the significant difference when comparing the score on the 10th day when the gel cream of Example 1 was applied and the score before the start of application or after the shaving on the 7th day (P <0. 001). Further, § on the right side of the figure shows, on the 10th day, a significant difference between the score obtained by applying the gel cream of Example 1 and the score obtained by applying the gel cream of Comparative Example 1 or the untreated score. (P <0.001). FIG. 2 is a diagram showing the change over time when scoring the degree of skin dryness by shaving when the gel cream of Example 1 or Comparative Example 1 is used and when it is not treated. The section at the top of the figure shows the significant difference when comparing the score on the 10th day when the gel cream of Example 1 was applied and the score before the start of application or after the shaving on the 7th day (P <0. 001). Further, § on the right side of the figure shows, on the 10th day, a significant difference between the score obtained by applying the gel cream of Example 1 and the score obtained by applying the gel cream of Comparative Example 1 or the untreated score. (P <0.001). FIG. 3 is a diagram showing the change over time when scoring the degree of moisture content in the skin when the gel cream of Example 1 or Comparative Example 1 was used and when it was not treated. The section at the top of the figure shows the significant difference when comparing the score on the 10th day when the gel cream of Example 1 was applied and the score before the start of application or after the shaving on the 7th day (P <0. 001). Further, § on the right side of the figure shows, on the 10th day, a significant difference between the score obtained by applying the gel cream of Example 1 and the score obtained by applying the gel cream of Comparative Example 1 or the untreated score. (P <0.001).

  Hereinafter, a mode for carrying out the present invention (hereinafter referred to as “the present embodiment”) will be described in detail. In addition, this invention is not limited to the following embodiment.

（式中、Ｒ^１はグリコシル基、リン酸基、又はＲ^２と結合した環状リン酸基を示し、Ｒ^２は−ＣＨ_２ＯＨ、−ＣＨＯ、−ＣＨ_２ＮＨ_２、−ＣＨ_２−アミノ酸残基、又は−ＣＨ_２−ＯＰＯ_２Ｈを示し、Ｒ^３は水素原子又は−ＰＯ_３Ｈ_２を示す。） The anti-inflammatory agent, moisturizing agent, therapeutic agent for atopic dermatitis and external preparation of this embodiment contain a compound represented by the formula (1) which is a vitamin B6 derivative or a salt thereof as an active ingredient.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )

R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ² . In the present specification, the “glycosyl group” means a residue obtained by removing the hydroxyl group at the 1-position (position 2 in the case of fructose) of a sugar compound. The anomeric form of the ether bond between the glycosyl group represented by R ¹ and the pyridine ring may be either α or β type, or a mixture of both. The type of sugar compound constituting the glycosyl group is not particularly limited, and may be any of monosaccharide, disaccharide, trisaccharide, or tetrasaccharide or higher oligosaccharide. With regard to the steric form of the sugar compound, it may be D- or L-, or a mixture. Examples of the sugar compound constituting the glycosyl group include D-glucose, L-glucose, D-galactose, L-galactose, D-mannose, L-mannose, D-fructose, L-fructose, D-ribose, L- Ribose, D-xylose, L-xylose, D-arabinose, L-arabinose, D-talose, L-talose, D-lyxose, L-lyxose, D-allose, L-allose, D-altrose, L-alt Loose, D-Growth, L-Growth, D-Idose, L-Idose, D-Quinobose, L-Quinobose, D-Rhamnose, L-Rhamnose, D-Fucose, L-Fucose, Maltose, Cellobiose, Lactose, Maltotri Oose and the like. Among these, as a sugar compound which comprises a glycosyl group, D-glucose or D-galactose is preferable.

The phosphoric acid group represented by R ¹ may be any of a chain ester such as monophosphoric acid, pyrophosphoric acid, and tripolyphosphoric acid, and a cyclic ester body with R ² such as monophosphoric acid, pyrophosphoric acid, and tripolyphosphoric acid, or a mixture of both. It may be.

R ² is _{-CH 2 OH, -CHO, -CH 2} NH 2, -CH 2 - shows the amino acid residue, or a _{-CH 2} -OPO 2 H. The —CH ₂ -amino acid residue represented by R ² means a group in which the amino terminus of an amino acid is bonded to —CH ₂ —. When an asymmetric carbon atom of an amino acid is present, it may be either an optically active substance or a racemate. Examples of amino acid compounds constituting the amino acid group include acidic amino acids such as glutamic acid, aspartic acid, cysteic acid, and homocysteic acid, glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, threonine, serine, homoserine, tyrosine, Examples include neutral amino acids such as cysteine, methionine, asparagine, and glutamine, and basic amino acids such as lysine, ornithine, arginine, and histidine. Of these, L-serine is preferred as the amino acid compound constituting the amino acid group.

  The compound represented by the formula (1) can form a salt. Examples of pharmacologically acceptable salts include mineral salts such as hydrochloride, hydrobromide, sulfate, nitrate, and phosphate, methanesulfonate, benzenesulfonate, and paratoluenesulfone. Acid salt, acetate salt, propionate salt, tartrate salt, fumarate salt, maleate salt, malate salt, oxalate salt, succinate salt, citrate salt, benzoate salt, mandelate salt, cinnamate salt, Examples include organic acid salts such as lactate. When an acidic group is present in the compound represented by the formula (1), for example, a metal salt such as lithium salt, sodium salt, potassium salt, magnesium salt, calcium salt, or ammonium salt, methylammonium salt, dimethylammonium Examples thereof include ammonium salts such as salts, trimethylammonium salts, and dicyclohexylammonium salts. The compound represented by the formula (1) may form a salt with an amino acid such as glycine.

  The compound represented by the formula (1) or a salt thereof may exist as a hydrate or a solvate. Since the compound represented by the formula (1) has one or more asymmetric carbons, it may exist as a stereoisomer such as an optically active substance or a diastereomer. Pure forms of stereoisomers, optical antipodes or any mixture of diastereomers, racemates and the like are all encompassed within the scope of the compound represented by formula (1).

As preferable examples of the compound represented by the formula (1), for example,
Pyridoxine 3-β-glucoside pyridoxine 3-α-glucoside pyridoxamine 3-β-glucoside pyridoxamine 3-α-glucoside pyridoxal 3-β-glucoside pyridoxal 3-α-glucoside pyridoxine 3-β-galactoside pyridoxine 3-α -Galactoside N- (4-pyridoxylmethylene) -L-serine 3-β-glucoside N- (4-pyridoxylmethylene) -L-serine 3-α-glucoside pyridoxine 3-phosphate pyridoxine 3,4'-cyclic Examples include phosphoric acid N- (4-pyridoxylmethylene) -L-serine 3-phosphate. Moreover, as an example of the compound represented by Formula (1), D-isomer of these compounds can also be mentioned. As an example of the compound represented by the formula (1), pyridoxine 3,4′-cyclic phosphoric acid represented by the formula (2) is most preferable. As a salt of pyridoxine 3,4′-cyclic phosphate, a sodium salt is preferable.

  The compound represented by the formula (1) or a salt thereof has an effect of suppressing skin inflammation when administered to the skin. Therefore, the compound represented by the formula (1) or a salt thereof can be used as an anti-inflammatory agent. Skin inflammation is so-called dermatitis, which has various symptoms such as erythema, papules, blisters, crusts and scales, and is a general term for skin diseases with itching. Causes of such inflammation include (1) when there is irritation to the skin, (2) when the protective function against irritation is reduced due to dry skin, and (3) causes an inflammatory reaction to allergic substances There is a case. Therefore, skin irritation is often caused mainly by skin irritation, irritation caused by shaving is also caused by skin irritation, and irritation is further increased for dry skin. Among these inflammations, the anti-inflammatory agent of the present embodiment exhibits an excellent inhibitory effect especially on inflammation caused by shaving. In the present specification, shaving means shaving or hair removal.

  In the anti-inflammatory agent of the present embodiment, the content of the compound represented by the formula (1) or a salt thereof is not particularly limited, and can be appropriately adjusted by those skilled in the art. As content rate of the compound represented by Formula (1) or its salt, 0.01-10 mass% is preferable with respect to the whole quantity of an anti-inflammatory agent, for example, 0.1-5 mass% is more preferable, 0 More preferably, it is 5-3 mass%. If the content rate of the compound represented by Formula (1) or its salt is in the said range, it is suitable from a viewpoint of the effect of suppressing skin inflammation.

  The compound represented by the formula (1) or a salt thereof has an effect of suppressing the drying of the skin and increasing the moisture content of the skin by being administered to the skin. Therefore, the compound represented by the formula (1) or a salt thereof can be used as a humectant. In particular, the moisturizing agent of the present embodiment exhibits an excellent inhibitory effect against drying due to shaving.

  In the humectant of the present embodiment, the content of the compound represented by the formula (1) or a salt thereof is not particularly limited and can be appropriately adjusted by those skilled in the art. As content rate of the compound or its salt represented by Formula (1), 0.001-10 mass% is preferable with respect to the whole quantity of a moisturizer, for example, 0.01-5 mass% is more preferable, and 0.0. 1-3 mass% is further more preferable. If the content rate of the compound represented by Formula (1) or its salt is in the said range, it is suitable from a viewpoint of the effect of suppressing dryness of the skin and increasing the moisture content of the skin.

  Moreover, since the compound represented by Formula (1) or its salt improves the inflammation and dryness of the skin, itching skin can be suppressed. Therefore, the compound represented by the formula (1) or a salt thereof can be used as a therapeutic agent for atopic dermatitis. In the present specification, the therapeutic agent for atopic dermatitis has a function as an antidiarrheal agent.

  In the therapeutic agent of the present embodiment, the content of the compound represented by the formula (1) or a salt thereof is not particularly limited, and can be appropriately adjusted by those skilled in the art. As content rate of the compound represented by Formula (1) or its salt, 0.01-10 mass% is preferable with respect to the whole quantity of a therapeutic agent, for example, 0.1-5 mass% is more preferable, and 0.1. 5-3 mass% is further more preferable. If the content rate of the compound represented by Formula (1) or its salt is in the said range, it is suitable from a viewpoint of the effect of suppressing itching by suppressing the inflammation and dryness of the skin by atopic dermatitis. is there.

  Furthermore, the compound represented by the formula (1) or a salt thereof can be used as an external preparation in combination with a steroid because it has an excellent moisturizing effect and an increase in the moisture content of the skin.

  In the external preparation of the present embodiment, the content of the compound represented by the formula (1) or a salt thereof is not particularly limited and can be appropriately adjusted by those skilled in the art. As content rate of the compound represented by Formula (1) or its salt, 0.001-10 mass% is preferable with respect to whole quantity of an external preparation, for example, 0.01-5 mass% is more preferable, and 0.0. 1-3 mass% is further more preferable. If the content rate of the compound or its salt represented by Formula (1) is in the said range, it is suitable from a viewpoint of the effect of suppressing the drying of the skin by a steroid type external preparation.

  Although the manufacturing method of the compound represented by Formula (1) is not specifically limited, For example, it can obtain by the method described in patent document 1 and 2.

  In the production of the anti-inflammatory agent, moisturizer, therapeutic agent and external preparation of the present embodiment, components that are usually used in preparations such as cosmetics, quasi-drugs, and external medicines, as long as the effects of the invention are not impaired. For example, water (purified water, hot spring water, deep layer water, etc.), oil agent, surfactant, metal soap, gelling agent, powder, alcohols, water-soluble polymer, film forming agent, resin, inclusion compound, antibacterial Agents, fragrances, deodorants, salts, pH adjusters, fresheners, extracts derived from plants, animals and microorganisms, active oxygen scavengers, blood circulation promoters, astringents, antiseborrheic agents, moisturizers, chelating agents, Keratolytic agents, enzymes, hormones, other vitamins, etc. can be added as needed.

  The forms of the anti-inflammatory agent, moisturizing agent, therapeutic agent and external preparation of this embodiment are not particularly limited as long as they can be administered to the skin, and examples thereof include ointments, lotions, gels, creams, milky lotions, essences, and beauty serums. It is done.

  Effective doses and administration schedules of the anti-inflammatory agent, moisturizer, therapeutic agent and external preparation of this embodiment can be appropriately determined by those skilled in the art depending on the administration method, symptoms, patient weight, age, etc. .

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated more concretely, this invention is not limited to these Examples.

Test Example: Skin Irritation and Drying Inhibition Effect due to Shaving (1) Sample Comparison Example 1: Placebo Gel Cream Example 1: Pyridoxine 3,4′-cyclic phosphate (PVP) with respect to the total mass of placebo gel cream Gel cream with 1% PVP prepared so as to be 1% by mass

(2) Measuring method In order to examine the effect of shaving on the skin, skin irritation and irritability (skin inflammation, dryness and inflammation of pores), skin color, The moisture content of the skin was evaluated. Shaving was performed with a razor on the left and right legs (range from knee to ankle). The gel cream of Comparative Example 1 or Example 1 was applied to the upper half of the shaved leg, and nothing was applied to the lower half of the leg. Various evaluation measurements were performed on the outer side surfaces of the leg part to which the gel cream of Comparative Example 1 or Example 1 was applied and the untreated leg part to which nothing was applied. In order to adjust the skin condition, a common pretreatment was performed on subjects from 3 days before the start of the test. Thereafter, various evaluation measurements, shaving and sample application were performed according to the schedule shown in Table 1.

(3) Evaluation method (3-1) Evaluation of skin irritation and hypersensitivity (skin irritation, dryness and inflammation of pores) Skin irritation, dryness and inflammation of pores were observed with a magnifying lamp on the subject's skin. Evaluation was made by observation. The degree of skin irritation and dryness was classified into the symptoms shown in Tables 2 and 3 and scored.

(3-2) Evaluation of skin color The skin color was measured using a color difference meter (Chromameter CRL 400, manufactured by Konica Minolta Co., Ltd.), and L ^* a ^* b ^* determined by the International Commission on Illumination (CIE) ^. Evaluation was based on color space.

(3-3) Evaluation of Skin Moisture Content (Keratin Moisture Content) Skin moisture content was measured using a Corneometer (registered trademark, Derma Unit SSC3, manufactured by Curage and Khazaka). The measured value indicates the capacitance. If the skin has a lot of moisture, the capacitance increases and the relative value is displayed large.

(4) Results (4-1) Evaluation of skin irritation and hypersensitivity (skin inflammation, dryness and pore inflammation) The test results of skin inflammation and dryness are shown in FIGS. Compared with the case where the gel cream of Comparative Example 1 was applied and when the gel cream of Example 1 was applied, the inflammation and drying of the skin on the 10th day after the start of application of the sample were remarkably suppressed. (Comparison between Example 1 and Comparative Example 1 and untreated on day 10 in FIGS. 1 and 2; §: P <0.001). In addition, when the gel cream of Example 1 was applied, the skin condition was 10 days after the start of application of the sample, compared to the skin condition before the start of application of the sample (day 0) and after 7 days after the start of application of the sample. Inflammation and desiccation were remarkably suppressed (Comparison between Example 10 of FIG. 1 and FIG. 2 before 10 days before application and after 7 days of shaving, §: P <0.001). Regarding the inflammation of the pores, in the case where the gel cream of Comparative Example 1 was applied and in the case where the gel cream was not treated, the number of subjects in which papules and cysts were observed increased on the 10th day after the start of the application of the sample as compared with before that. On the other hand, when the gel cream of Example 1 was applied, inflammation of pores was not observed on the 10th day after the start of application of the sample, and suppression of inflammation was observed.

(4-2) Evaluation of skin color No change was seen in the color of the skin when the gel creams of Comparative Example 1 and Example 1 were applied and when they were not treated.

(4-3) Evaluation of Skin Moisture Content (Keratin Moisture Content) FIG. 3 shows a test result of skin moisture content (keratin moisture content). Compared with the case where the gel cream of Comparative Example 1 was applied and the case where the gel cream of Example 1 was applied, the moisture content of the skin on the 10th day after the start of application of the sample was significantly increased ( Comparison between Example 1 and Comparative Example 1 and untreated on the 10th day of FIG. 3, §: P <0.001). In addition, when the gel cream of Example 1 was applied, the moisture content of the skin was significant on the 10th day after the start of application of the sample, comparing the skin condition before the start of application of the sample and after 7 days after the start of application of the sample. (Comparison between the 10th day of Example 1 in FIG. 3 and before and after 7 days of shaving, §: P <0.001).

Claims (10)

The anti-inflammatory agent containing the compound or its salt represented by Formula (1).

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )   The anti-inflammatory agent of Claim 1 with respect to the inflammation resulting from shaving or hair loss.   The anti-inflammatory agent according to claim 1 or 2, wherein the compound represented by the formula (1) is pyridoxine 3,4'-cyclic phosphate. A humectant containing the compound represented by formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )   The humectant according to claim 4 against drying due to shaving or hair removal.   The humectant according to claim 4 or 5, wherein the compound represented by the formula (1) is pyridoxine 3,4'-cyclic phosphoric acid. A therapeutic agent for atopic dermatitis comprising a compound represented by formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. )   The therapeutic agent according to claim 7, wherein the compound represented by the formula (1) is pyridoxine 3,4'-cyclic phosphate. An external preparation containing a steroid and a compound represented by the formula (1) or a salt thereof.

(In the formula, R ¹ represents a glycosyl group, a phosphate group, or a cyclic phosphate group bonded to R ^2, and R ² represents —CH ₂ OH, —CHO, —CH ₂ NH ₂ , —CH ₂ -amino acid residue. A group, or —CH ₂ —OPO ₂ H, and R ³ represents a hydrogen atom or —PO ₃ H _2. ) The external preparation according to claim 9, wherein the compound represented by the formula (1) is pyridoxine 3,4'-cyclic phosphoric acid.

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