JPH05132414A - Hair producing agent - Google Patents

Abstract

PURPOSE:To obtain a hair producing agent having extremely high trichogenic effects, comprising a quaternary ammonium compound as an active ingredient. CONSTITUTION:A hair producing agent comprising 0.05-30wt.%, preferably 0.5-5wt.% based on total amounts of preparation of a compound of the formula (R<1> is 6-25C unsaturated hydrocarbon monofunctional group; R to R are 1-4C alkyl; (n) us 2-4; X is anion) such as N-{3-(Z)-13-docoseneamido)propyl}-N,N,N- trimethylammonium iodide as an active ingredient. The agent can be prepared into a dosage form such as lotion, emulsion, cream, gel or aerosol and a proper amount of the agent is applied to scalp several times daily.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair growth agent containing a quaternary ammonium compound as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, carpronium chloride, estradiol, chelthiamarin, pentadecanoic acid glyceride, ginseng extract and the like have been used as hair nourishing agents, hair-growth agents and hair-growth agents. On the other hand, some of the compounds used in the present invention are disclosed in JP-A-56-73011 and 59-1014.
No. 48, U.S. Pat. No. 4,024,097, etc., but its hair growth action is not known.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a new type of hair growth agent having a remarkable hair growth effect.

[0004]

The present invention comprises:

[0005]

[Chemical 2]

(In the formula 2, R ¹ represents a monovalent group of an unsaturated hydrocarbon having 6 to 25 carbon atoms, and R ² , R ³ and R ⁴ are the same or different and have 1 to 4 carbon atoms. Is an alkyl group, n is an integer of 2 to 4, and X is an anion atom or atomic group).

In the present invention, the monovalent group of unsaturated hydrocarbon having 6 to 25 carbon atoms means hexenyl group, hexynyl group, heptenyl group, octenyl group, octynyl group, nonenyl group, decenyl group, decynyl group, Undecenyl group,
4,8-dimethyl-3,7-nonadienyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, 4,8,12-trimethyl-3,7,11-tridecatrienyl group, heptadecenyl group, Heptadecadienyl group, heptadecatrienyl group, octadecenyl group, octadecadiynyl group, nonadecenyl group, nonadecatetraenyl group, icosenyl group, icosadiynyl group, henicosenyl group, docosenyl group, tricosenyl group, tetracosenyl group, pentacosenyl group A monovalent group of a linear or branched unsaturated hydrocarbon containing at least one double bond or triple bond in the carbon chain.
In addition, the alkyl group having 1 to 4 carbon atoms refers to a linear or branched alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group. As the atom or atomic group to be an anion, a fluorine atom, a chlorine atom, a bromine atom,
Iodine atom, sulfate group, nitrate group, nitrite group, methyl sulfate group, ethyl sulfate group, dimethyl phosphate group, methanesulfonic acid group, benzenesulfonic acid group, p-toluenesulfonic acid group, acetic acid group, etc. can be used. it can.

The hair regrowth agent of the present invention may use one kind of the compound of Chemical formula 2 or two or more kinds thereof as an active ingredient. The dosage form may be a lotion, emulsion, cream, gel, aerosol or the like, which can be prepared according to a commonly used method (for example, the method defined in the 12th edition Japanese Pharmacopoeia). The amount of the active ingredient compounded is 0.05 to 30% by weight, preferably 0.5 to 5% by weight, based on the total amount of the preparation. The hair growing agent of the present invention is applied to the scalp in an appropriate amount several times a day.

In addition to the above-mentioned essential components, the hair regrowth agent of the present invention is a substance that is usually used as a hair nourishing agent, such as a solvent (ethyl alcohol, isopropyl alcohol, 1,3-butylene glycol, 1,4-butylene glycol, propylene glycol). , Dipropylene glycol, glycerin, diglycerin, polyethylene glycol, purified water, etc.),
Mucopolysaccharides (hyaluronic acid, chondroitin-4-sulfate, chondroitin-6-sulfate, dermatan sulfate, keratan sulfate, heparan sulfate, polysulfate of chondroitin sulfate, etc.), preservatives (paraben, benzoic acid, etc.), vitamins [Vitamin A, Vitamin B ₁ , Vitamin B ₂ , Vitamin B ₆ , Vitamin C, Vitamin D, Vitamin E and derivatives thereof (for example, vitamin E acetate ester)], oil (liquid paraffin, white petrolatum, solid paraffin, Ceresin, microcrystalline wax, cholesterol, squalane, olive oil,
Rosehip oil, mink oil, jojoba oil, hydrogenated castor oil,
Hardened coconut oil, isopropyl myristate, ethyl caprate, ethyl caprylate, palmitoleic acid, ethyl palmitoleate, ethyl linoleate, ethyl linolenate, oleic acid, stearic acid, linoleic acid, linolenic acid, palmitic acid, behenic acid, laurin Acid, stearyl alcohol, cetyl alcohol, lauryl alcohol, oleyl alcohol, cetyl isooctanoate), bactericide [sulfur, chlorhexidine gluconate, chlorhexidine hydrochloride, cetylpyridine hydrochloride, decalinium chloride, isopropylmethylphenol, quaternary ammonium salt (for example, , Benzalkonium chloride, etc.), hinokitiol, etc.], nonionic surfactant (polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sorby Fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyglycerin alkyl phenyl ether, polyoxyethylene hydrogenated castor oil, copolymer of polyoxyethylene and polypropylene glycol) , Anionic surfactants (N-acyl amino acid salt, N-acyl sarcosine salt, alkyl phosphate ester salt, acylmethyl taurine, etc.), cationic surfactants (alkyl trimethyl ammonium, alkyl-N, N-dialkyl) Aminoacetic acid ester, etc.), amphoteric surfactant (imidazoline, amine oxide, etc.), polymer surfactant (casein, etc.), silicone derivative (silicone oil, polyol-modified silicone) Silicone resin, etc.), thickeners (methylcellulose, polyvinylpyrrolidone, carboxymethyl cellulose, carboxyethyl cellulose, hydroxypropyl cellulose, etc. carboxyvinyl polymers), clay minerals (montmorillonite, saponite, etc. hectorite), pH
Regulators (diisopropanolamine, citric acid, etc.),
Antioxidants (dibutylhydroxytoluene, sodium bisulfite, catechin, glucnodeltalactone, etc.), whitening agents (arbutin, kojic acid, etc.), cooling agents (1-menthol, camphor, etc.), anti-inflammatory agents (glycyrrhetinic acid, Dipotassium glycyrrhizinate, berberine chloride, shikonin, guaiazulene, allantoin, δ-
Aminocaproic acid), peripheral vasodilators (methyl nicotinate, benzyl nicotinate, chelthiamarin, minoxidil, diazoxide, capsicum extract, capsaicin, carpronium chloride, etc.), adrenal cortex hormones (hydrocortisone acetate, betamethasone valerate, etc.), Antihistamines (diphenhydramine hydrochloride, isothipendyl hydrochloride, etc.), local anesthetics (dibucaine hydrochloride,
Lidocaine hydrochloride, etc.), keratolytic agent (urea, salicylic acid, etc.), keratinization regulator [vitamin A acid and its derivatives (eg 13-cis-retinoic acid, etretinate, etc.)], estrogen (17β-estradiol, ethinyl estradiol, Estrone, etc., luteinizing hormone (progesterone, 17α-hydroxyprogesterone acetate, etc.), antiandrogen (cyproterone acetate, 4-androsten-3-one-17β
-Carboxylic acid etc.), fragrance, sequestering agent, ultraviolet absorber, moisturizer (hechima extract, carrot extract, diisopropyl acetate, pyrrolidone carboxylic acid, polyglutamic acid, polyoxyalkylene alkyl glucoside ether, collagen, lecithin, ceramide , 2-aminoethanesulfonic acid, crocin, crocetin, etc.), herbal medicine extracts (kamushi extract, bamboo shoot ginseng extract, radish extract, saffron extract, etc.) can be added within a range that does not impair the effects of the present invention.

[0010]

EFFECTS OF THE INVENTION The present invention makes it possible to provide a hair-growth agent having a significantly high hair-growth effect.

[0011]

EXAMPLES The present invention will be described in more detail with reference to production examples, examples and test examples. (Production Example) N- {3-[(Z) -13-docosenamide] propyi
Ru} -N, N, N-trimethylammonium = iodide

[0012]

[Chemical 3]

(1) (Z) -13-docosenoic acid 10.0
g and N, N-dimethyl-1,3-diaminopropane 3.
6 g was refluxed in xylene for 5 hours while removing generated water. After distilling off xylene, the residue was recrystallized from xylene-n-hexane to give N- [3- (dimethylamino) propyl]-(Z) -13-docosenamide 5.8.
g was obtained. (2) 2.00 g of the compound obtained above and 1.
34 g was reacted in ethanol at room temperature for 3 days, and the product was recrystallized from ethanol to give the title compound 2.3.
8 g was obtained. m. p. 110 to 112 ° C. ¹ H-NMR (CDCl ₃ ) δ (ppm): 0.88
(3H, t, J = 6.5Hz), 1.26 (28H,
s), 1.52 to 1.70 (2H, m), 1.94 to
2.22 (6H, m), 2.31 (2H, t, J = 7.
5 Hz), 3.33 to 3.47 (11 H, m), 3.8
1-3.92 (2H, m), 5.34 (2H, t, J =
4.5 Hz), 7.16 (1H, t, J = 6.0 Hz) Of the compounds of Chemical formula 2, other novel compounds can be produced according to the above Production Examples. (Example 1)

[0014]

[Table 1]

A lotion was prepared by mixing and dissolving each component in purified water, propylene glycol and glycerin. (Example 2)

[0016]

[Table 2]

A lotion was prepared by mixing and dissolving each component in purified water, ethyl alcohol and 1,3-butylene glycol. (Example 3)

[0018]

[Table 3]

A lotion was prepared by mixing and dissolving each component in purified water, isopropyl alcohol, propylene glycol and dipropylene glycol. (Example 4)

[0020]

[Table 4]

The oil-soluble component and the surfactant were dissolved in the oil phase under heating to give N- {2-[(Z) -13-docosenamido] ethyl} -N, N, N-trimethylammonium = iodide and the water-soluble component. Add the aqueous phase that was dissolved by heating, emulsify,
Cooled to prepare cream. (Example 5)

[0022]

[Table 5]

A lotion was prepared by mixing and dissolving each component in ethyl alcohol. (Example 6)

[0024]

[Table 6]

The oil-soluble component and the surfactant were dissolved in the oil phase under heating to give N- {2-[(9Z, 12Z) -9,12-octadecadienamide] ethyl} -N, N, N-trimethyl. An aqueous solution prepared by heating and dissolving ammonium = iodide and a water-soluble component was added, and the mixture was emulsified and cooled to prepare an emulsion. (Example 7) Stock solution

[0026]

[Table 7]

Filler dimethyl ether A stock solution was prepared according to the method for producing the emulsion of Example 6, and the following aerosol was prepared by a usual filling method. Filling formulation Undiluted solution: 30% by weight, Filler: 70% by weight

(Test Example) Hair Growth Effect Test The hair growth effect test of the compound of the present invention was carried out using C3H mice (male,
(7 weeks old) 5 animals were used as one group, and their back hairs were hair-removed with hair clippers, and the area of the sample 0.
Apply 2 ml for 10 days, and then measure the degree of hair growth after 7
It was visually evaluated at the stage.

No hair growth is observed 0 points A slight amount of vellus hair is grown 1 point A slight amount of bristles is grown 2 points Bristles are grown on 25% of the hair removal site 3 points Bristles are dehaired 4 points on 50% of the site 5 points on which bristles grow on 75% of the hair removal site 5 points 6 points on which bristles grow on 100% of the hair removal site 6 points Evaluation of the results 42 days after application of the sample Table 9 is the average value of the points
Shown in.

[0030]

[Table 8]

[0031]

[Table 9]

Front page continuation (72) Inventor Masahiro Hasegawa 3-24-1 Takada, Toshima-ku, Tokyo Taisho Pharmaceutical Co., Ltd. (72) Inventor Katsuo Hatayama 3-24-1 Takada, Toshima-ku, Tokyo Taisho Pharmaceutical Co., Ltd. In the company

Claims (1)

[Claims] Claims: (In Chemical Formula ¹ , R ¹ represents a monovalent group of an unsaturated hydrocarbon having 6 to 25 carbon atoms, and R ² , R ³ and R ⁴ are the same or different and are alkyl groups having 1 to 4 carbon atoms. And n is 2 to
4 represents an integer of 4 and X represents an atom or an atomic group which becomes an anion. ) A hair growth agent containing a compound represented by the formula (1) as an active ingredient.