JPH11335244A - Hair growing and restoring agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a hair growing and restoring agent containing a specific compound, directly acting on the differentiation and multiplication of the mother cell of hair and having an excellent growing and restoring effect and an excellent effect on the prevention of loss of hair. SOLUTION: This hair growing and restoring agent is preparaed by including a compound of formula I (wherein, R<1> , R<3> and R<4> are each H, OH or a lower alkoxy; R<2> is H or a lower alkyl), (pref. a compound of formula II or formula III). It is pref. that the compound of formula I is included in a content of, 0.01-3 wt.%, and the hair growing and restoring agent is formulated with at least one of a circulation accelerator, an antibacterial agent, a keratolytic, an antiseborrheic, etc., and is dissolved in water or a mixed solvent of water-lower alcohol, etc., in the usage of the agent. The agent has a form of preparations selected from a group consisting of solution as a principal form, lotion, cream and jelly. The solution is included together with carbonic acid gas and the fluid property of the agent is pref. pH 4.5-6.5.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair-growing / hair-growing agent having an excellent hair-growing / hair-growing effect and an effect of preventing hair loss.

[0002]

BACKGROUND OF THE INVENTION Problems to be solved by the prior art and the invention
Synthetic drugs or natural product extracts having various effects are used in hair-growing medicines or cosmeceuticals,
All of these have the drawback that sufficient effects cannot be obtained with a small amount of addition, unpleasant irritation at the application site with a large amount of addition, and dermatitis occurs when used continuously. I have.

[0003] The above hair-growing and hair-growing agent is not a direct effect on the differentiation and proliferation of hair cells, but an indirect effect through the normalization of the condition of the scalp, and is not effective for human hair. No sufficient hair-growth / hair-growth effect was shown.

[0004] Hair growth and recovery, which directly act on the differentiation and proliferation of hair matrix cells and exhibit excellent hair growth and hair growth effects and hair loss prevention effects.
The development of a hair restorer has been desired.

[0005]

Means for Solving the Problems Accordingly, the present inventors have found that the compound represented by the following general formula (1) directly acts on the differentiation and proliferation of hair cells, and has an excellent hair-growth / hair-growth effect and prevention of hair loss. The inventors have found that the present invention has an effect, and completed the present invention.

That is, the present invention provides the following general formula (1)

[0007]

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Wherein R ¹ , R ³ and R ⁴ are the same or different and each represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R ² represents a hydrogen atom or a lower alkyl group; and R ³ and R ⁴ May together form an adjacent pyran ring which may be substituted with one or two methyl or oxo groups together with the adjacent carbon atoms at the 3- and 4-positions.)
And a hair-growth / hair-growth agent comprising the compound represented by the formula (1) as an active ingredient.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1), R ¹ , R
³ and R ⁴ are the same or different and represent a hydrogen atom, a hydroxyl group or a lower alkoxy group. The lower alkoxy group preferably has 1 to 6 carbon atoms. Among them, a hydrogen atom, a hydroxyl group and a methoxy group are particularly preferred. R ² represents a hydrogen atom or a lower alkyl group. The lower alkyl group preferably has 1 to 6 carbon atoms. Of these, a hydrogen atom and a methyl group are particularly preferred.

Further, R ³ and R ⁴ jointly form an adjacent 3
Together with the carbon atoms at the 4- and 4-positions, one or two methyl groups or oxo groups may form an optionally substituted pyran ring. The oxygen atom constituting the pyran ring is preferably adjacent to the carbon atom at the 4-position. The carbon atom which may be substituted by a methyl group or an oxo group is preferably a carbon atom adjacent to an oxygen atom constituting a pyran ring. It is preferable that two methyl groups are substituted.

Particularly preferred of these compounds are shown below.

[0012]

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[0013]

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Among the above compounds, compounds (a) to (p)
Can be synthesized by an existing method, for example, the method described in New Experimental Chemistry Course (Maruzen), Vol. 14, “Synthesis and Reaction of Organic Compounds”. Compound (q) may be, for example, Akane (Rubia)
Cordifolia) from Phytochemistr
y, Vol. 28, pp. 3465-3468 (1989). Compound (r) can be obtained, for example, from Akane (Rubia cordifolia) by Acta Pha
rmaceutica sinica, 27, 278
~ 282 (1992).

The compounds represented by the general formula (1) can be used as a mixture of one or more kinds. The compound represented by the general formula (1) is used in an amount of 0.001 to 10% by weight, particularly 0.01 to 10% by weight, in the hair growth and hair growth agent of the present invention, from the viewpoints of hair growth and hair growth effect and irritation to the scalp. It is preferred to contain 3% by weight.

The hair-growing / hair-growing agent of the present invention is used in order to further enhance the hair-growing / hair-growing effect, and is commonly used as a blood circulation promoting agent, an antibacterial agent, a keratolytic agent, an antiseborrheic agent, a local stimulant, an anti-inflammatory agent. , Humectant,
An antiandrogen, a hair follicle activator and the like can be added. It is preferable to use one or more of the above components as a mixture, and it is also preferable to use the components by dissolving them in water or a solvent such as water-lower alcohol. From the viewpoint of a synergistic effect with the compound represented by the general formula (1), the above components are incorporated in the hair growth and fostering agent of the present invention in an amount of 0.001 to 5% by weight, particularly 0.01 to 3% by weight. Is preferred.

The dosage form of the hair-growing / hair-growing agent of the present invention is mainly a liquid and is typically a lotion, but may be a cream or a gel. It is particularly preferable that the liquid preparation further contain carbon dioxide gas. Carbon dioxide is present as CO ₂ molecules in acidic solutions and exhibits vasodilatory effects. Therefore, the liquidity of the hair restorer / hair restorer of the present invention containing carbon dioxide is less than pH 7, especially pH 4.5.
-6.5 is preferred. As for the pH of the hair restorer / hair restorer, the acidity is further increased when carbon dioxide gas is injected and dissolved in the solution,
What is necessary is just to adjust so that final pH may be in the said range. This pH
Organic acids such as citric acid, tartaric acid and lactic acid or salts thereof, or phosphoric acid or salts thereof are suitable as regulators.

In addition to the above-mentioned components, the hair restorer / hair restorer of the present invention may contain, if necessary, an oily base, a gelling agent, various types of oily bases used in ordinary cosmetics as long as the effects of the present invention are not impaired. Emulsifiers, fragrances, antioxidants such as parahydroxybenzoic acid esters, and coloring agents such as dyes can be added and blended.

The hair restorer / hair restorer of the present invention can be produced by subjecting the compound represented by the general formula (1) and other components to operations such as mixing according to a conventional method.

[0020]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples.

Production Example 1 Production of Compounds (l) and (j) 2.0 g of 1,4-dihydroxy-2-naphthoic acid (compound (e), manufactured by Wako Pure Chemical Industries, Ltd.) was added in dimethylformamide in the presence of potassium carbonate. Then, methylation using iodomethane was carried out to obtain 1.9 g of compound (l). Further, 1.0 g of compound (l) was hydrolyzed with 2N-NaOH to obtain 0.8 g of compound (j).

Preparation Example 2 Preparation of Compounds (q) and (r) Root (Rubia cordifolia)
5 kg was extracted with 20 liters of methanol to obtain an extract. The extract was concentrated, and the organic phase obtained by partitioning with water-ethyl acetate was subjected to silica gel column chromatography (hexane-ethyl acetate system, hexane-chloroform system).
By recrystallization or ODS preparative HPLC, 2.9 g and 24.6 mg of compound (q) and (r), respectively.
Obtained.

Test Example 1 The hair follicles of SD newborn rats were surgically excised, and the compounds (a) to (r) were added to a medium at a concentration of 50 pg / ml, and organ culture was carried out. Was measured over time. Table 1 shows the results. As a comparative example, minoxidil was used in the same manner. The degree of hair elongation is a relative value when the hair elongation in only the culture solution (the group without addition) is 100.

[0024]

[Table 1]

From Table 1, it was confirmed that the compounds (a) to (r) had better hair-growth and hair-growth effects than the comparative compounds.

Test Example 2 Mouse Hair Growth Test A back hair of a group of 20 C3H / HeNCrj mice, 49 days old, was examined using an electric clipper and an electric shaver.
The hair was shaved over 2 × 4 cm ² without damaging the skin. Next, from the next day, a 0.1% by weight solution (50% ethanol) of the compounds c, k, n, q and the compound of the comparative example was applied to the shaved site once a day in 20 μl portions for 4 weeks. The group to which only the solvent (50% ethanol) was applied was used as a control. In order to observe the hair regeneration, the shaved area was photographed at a fixed magnification, and the daily change of the ratio of the regenerated hair area ((regenerated hair area / shaved area) × 100 (%)) was measured using an image analyzer. did. Table 2 shows the ratio of the regenerated hair area after 4 weeks.

[0027]

[Table 2]

From Table 2, it was confirmed that the compounds c, k, n, and q were significantly more excellent in the hair growth effect in mice than the compounds of the comparative examples.

Example 1 Hair-growing and hair-growing agents were prepared in the proportions shown in Table 3.

[0030]

[Table 3]

Example 2 Hair-growing / hair-growing agents were prepared in the proportions shown in Table 4.

[0032]

[Table 4]

[0033]

The hair restorer / hair restorer of the present invention has excellent hair restorer / hair restorer action over a long period of time.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Atsushi Ouchi 2606, Kabane-cho, Akaga-cho, Haga-gun, Tochigi Pref.

Claims (1)

[Claims] 1. The following general formula (1): (Wherein, R ¹ , R ³ and R ⁴ are the same or different and represent a hydrogen atom, a hydroxyl group or a lower alkoxy group. R ²
Represents a hydrogen atom or a lower alkyl group. R ³ and R
⁴ together with the adjacent 3 and 4 carbon atoms,
One or two methyl groups or oxo groups may form an optionally substituted pyran ring. A hair restorer / hair restorer comprising a compound represented by the formula (1) as an active ingredient.