JPS6344511A - Hair tonic - Google Patents

Abstract

PURPOSE:To obtain a hair tonic having improved preventing effects on fallingout of hair, promoting effects on hair production and growing effects on hair, and containing N-(hydroxystyryl)benzamide as an active ingredient. CONSTITUTION:A hair tonic containing 0.01-5wt% compound shown by the formula. The hair tonic can be blended with a pharmaceutically acceptable antimicrobial agent, refreshing agent, drug, oily component, humectant, surface active agent, perfume, ultraviolet light absorber, etc., and can be used in any form such as lotion, milky lotion, cream, ointment, jelly, spray, etc. A percutaneous dose is preferably 0.001-2mg/day based on 1kg weight.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel hair nourishing agent containing N(hydroxystyryl)benzamide as an active ingredient.

[Prior Art] Traditionally, the causes of baldness and hair loss include activation of male hormones in organs such as hair roots and sebaceous glands, decreased blood flow to hair follicles, excessive secretion of sebum, production of peroxides, and bacterial growth. Scalp abnormalities due to breeding etc., genetic factors, neurosis due to stress, etc.
It is thought to be secondary to disease and aging.

For this reason, conventional hair growth agents generally contain compounds that have the effect of eliminating or alleviating the above-mentioned causes.

[Problems that the invention aims to solve]However, the mechanism of hair loss and hair growth (1 It is not possible to sufficiently prevent hair loss.

In view of the above circumstances, the present inventors have conducted intensive research to obtain a substance that has an effective preventive effect against hair loss, and as a result,
The inventors have discovered a novel fact that N-(hydroxystyryl)benzamide has an excellent hair-nourishing effect, and have completed the present invention based on this finding.

(The following is a blank space) [Means and effects for solving the problem, that is, the present invention is directed to N-(hydroxystyryl) represented by the following structural formula.
It is a hair tonic that contains benzamide as an active ingredient.

The heather civilization will be explained in more detail below.

The N-(hydroxystyryl)benzamide used in the present invention is a known substance [Shigehiko Sugazawa; Pharmaceutical Journal, Vol. 55, 22
pp. 4-233 (1935L A, Gearrad (A, Ga
1at): Journal Saibu American Chemical
Society (J, Amer, Chem, Soc
), Vol. 72, 4436-4439N (1950) 1. The existence of cis and trans structural isomers has been suggested.

The method for synthesizing this compound is described in the above-mentioned literature, but its pharmacological action has not been published so far, and it is of course not known that it has a hair-nourishing action.

As used herein, "hair nourishing effect" or "hair nourishing effect" means prevention of hair loss, promotion of hair growth, and hair growth.

The method for producing this compound is a known method (West German patent; 37
N-1:2-hydroxy-2- obtained by reacting 4-hydroxyphenylethanolamine hydrochloride (octobamine hydrochloride) obtained in 3,286) with benzoyl chloride
(4-hydroxyphenyl)ethyl]benzamide,
It can be produced by heating without a catalyst or in the presence of a catalyst.

Examples of manufacturing the compounds according to the present invention are shown below. Note that the present invention is not limited to this.

1 garden! 10. Octobamine hydrochloride in a 300 ml Erlenmeyer flask.
08, add 100 ml of pyridine and dissolve, then cool. Li benzoyl chloride with stirring 7.43 e
It was added dropwise little by little. After continuing stirring for 30 minutes after the completion of the dropwise addition, 100 ml of water was added to the reaction solution, and using a separating funnel)-
The mixture was extracted three times with 100 ml of chloroform. After distilling off the solvent of the extract, 9.28 N-[2-
Hydroxy-2-(4-hydroxyphenyl)ethyl]
Benzamide was obtained. 9.2 g of the N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]benzamide obtained here was placed in a 3000 ml three-necked flask, and 1500 ml of toluene and 3.0 g of aluminum oxide were added.
was added and refluxed for 40 hours. The reaction product was filtered to remove the residual solvent, separated by column chromatography using silica gel, and purified by recrystallization to obtain cis form (0.6 g) and trans form (<4.4 g) of N-( 4-Hydroxystyryl)benzamide was obtained.

Melting point: cis type 182℃, trans type 206℃ then N
The formulation of -(4-hydroxystyryl)benzamide for use as a hair tonic will be described.

The hair growth agent of the present invention can be used in the form of a mixture containing N-(4-hydroxystyryl)benzamide, as well as pharmaceutically acceptable additives and other drugs.

Examples of the additives include hinokitiol, hexachlorophene, phenol, benzalkonium chloride,
Antibacterial agents such as cetylpyridinium chloride, undecylenic acid, trichlorocarbanilide and bithionol, derivatives such as glycyrrhizinic acid and its ammonium salts, anti-inflammatory or cooling agents such as allantoin and menthol, salicylic acid, zinc and its compounds, lactic acid and its alkyl Drugs such as esters, animal and vegetable oils such as olive oil, macadamia nut oil, and squalane, hydrocarbon oils such as liquid paraffin, ester oils such as isopropyl myristate, cetyl isooctanoate, and 2-ethylhexyl palmitate, and beeswax. Waxes such as, higher fatty acids, oils such as higher alcohols, water, 334 substances such as lactic acid and its ethyl ester, polyethylene glycol, glycerin,
Examples include polyhydric alcohols such as sorbitol, lower alcohols such as ethanol, mucopolysaccharides, humectants such as lolidone carponate, surfactants, fragrances, antioxidants, ultraviolet absorbers, pigments, etc. 1 type or 2
Use by mixing more than one species.

The dosage form of the hair tonic of the present invention may be any form as long as it can be used externally, such as liquid preparations for external use such as lotions, liniments, and milky lotions, and semi-solid preparations for external use such as creams, ointments, pasta, jelly, and sprays. can be mentioned.

The hair growth agent of the present invention contains 0.001 to 10% by weight of N(4-hydroxystyryl)benzamide as an active ingredient.
, preferably in a range of 0.01 to 5% by weight.

The hair growth agent of the present invention is administered by transdermal administration, in which it is directly applied or sprayed onto the skin. In addition, the dosage of the hair tonic of the present invention cannot be clearly defined because it varies depending on age, individual differences, illness, etc., but in general, when it is administered to humans, N.
- (4-Hydroxystyryl)benzamide transdermal dosage is 0.0001 to 20 per kg body weight and per day
mg, preferably 0.001-2 m6, and this amount can be administered once a day or in 2-4 divided doses.

EXAMPLES The method for formulating the hair growth agent and the hair growth effect according to the present invention will be explained in detail with reference to Examples below. Note that the present invention is not limited to this.

Example 1゜ A lotion having the following composition was prepared.

(Weight%) 95% ethanol 80・0N-(4
-hydroxystyryl) 0.1 Benzamide hinokitiol 0.01 Ethylene oxide of hydrogenated castor oil 0.5 (40 mol) adduct Purified water 19.01'fj
Materials and dyes: N-(4-hydroxystyryl)benzamide in an appropriate amount of 95% ethanol;
Hinokitiol, hydrogenated castor oil ethylene oxide (4
Add the adduct (0 mol), fragrance and pigment and dissolve with stirring,
Next, add purified water and make the clear liquid test lotion 14.

Salmon - goshi An emulsion was prepared from Phase A and Phase B having the following composition.

(Phase A) (Weight%) Whale wax
0.5 cetanol
2.0 Vaseline
5.0 Squalane 10.
0 Polyoxyethylene (10 mol) 2.0 Monostearate Sorbitan monooleate 1.0 N-(4-hydroxystyryl) 0.5 Benzamide (Phase B) Glycerin 10.0 Purified water
69.0 Fragrance, pigment, and soundproofing agent Dissolve appropriate amounts of phase A and phase B by heating and keep at 80°C. Both phases were mixed and emulsified and cooled to room temperature while stirring to obtain a milky lotion.

Sent R @ 414 3゜ A cream was prepared from Phase A and Phase B having the following composition.

(Phase A) (% by weight) Liquid paraffin 5.0 Cetostearyl alcohol 5.5 Petrolatum
5.5 Glycerin monostearate 3.0 Polyoxyethylene (20 mol) 3.0 2-Octyldodecyl ether probylparaben 0.3 (Phase B) N-(4-hydroxystyryl) 0.1 Benzamide glycerin 7.0 Dipropylene glycol 20.0 Polyethylene glycol 4000 5.0 Sodium hexametaphosphate
0.005' Purified water Dissolve appropriate amount of phase A by heating and keep at 70°C. Separately, phase B is dissolved by heating and kept at 70°C. Phase B was added to the human phase and stirred, and the resulting emulsion was cooled to obtain Cree-1\.

[Effects of the Invention] Test Example of Hair Nurturing Effect In order to investigate the hair cultivating effect of the hair tonic of the present invention, a tricogram test and a hair conversion rate test were carried out.

In both studies, 20 male subjects were given 10
Divide the subjects into two groups, each with a different number of subjects in each group.
A test solution of seeds was given for comparison.

Two types of test solutions are shown in Table 1.

(Margin below) Table 1 applied to the scalp of a person.

(1) Trichogram Observe the removed hair roots with a microscope before and after using both test solutions, calculate the number of telogen hair roots from the morphology of the hair roots, and determine the growth rate of both test solutions by increasing or decreasing the ratio. The hair effect was compared. A telogen hair root is a hair root that has stopped growing. People who complain of hair loss have more telogen hair roots than normal people, so the hair-nourishing effect was evaluated based on the decrease in telogen hair roots. The application of each test solution to the scalp was continued for 3 months, and 60 hair roots were removed for each test subject immediately before and immediately after application 5 and examined. The results are shown in Table 2.

(2) Hair conversion rate test 3 downy hair areas on the head of each of 40 subjects with androgenetic alopecia
The conversion rate of downy hair to fluff was compared before and after application of each of the above test solutions.

Fluff refers to hair other than downy hair, that is, hair with a length of 14 mm or more, and the conversion from downy hair to downy hair means a hair-nourishing effect. Immediately after the application of each of the 9 test solutions and immediately after the completion of the 4-month application, the conversion rate was measured by taking a close-up photograph of the above-mentioned down hair region on the head. The conversion rate to fluff is expressed as a percentage of the average of the three locations.

The results are shown in Table 3.

As is clear from the above results, it was found that N-(4-hydroxystyryl)benzamide exhibits an excellent hair-nourishing effect.

Claims (1)

[Scope of Claims] A hair nourishing agent containing N-(hydroxystyryl)benzamide as an active ingredient represented by the following structural formula ▲ Numerical formula, chemical formula, table, etc. ▼.