WO2013161978A1 - Hair growth agent - Google Patents

Hair growth agent Download PDF

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Publication number
WO2013161978A1
WO2013161978A1 PCT/JP2013/062332 JP2013062332W WO2013161978A1 WO 2013161978 A1 WO2013161978 A1 WO 2013161978A1 JP 2013062332 W JP2013062332 W JP 2013062332W WO 2013161978 A1 WO2013161978 A1 WO 2013161978A1
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group
hair
formula
hair growth
linear
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PCT/JP2013/062332
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French (fr)
Japanese (ja)
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室伏 きみ子
俊郎 諸星
茂行 今村
達郎 藤原
良彦 野方
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Sansho株式会社
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Publication of WO2013161978A1 publication Critical patent/WO2013161978A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/66Phosphorus compounds
    • A61K31/665Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q7/00Preparations for affecting hair growth

Abstract

The purpose of the present invention is to provide a hair growth agent having an excellent hair-nourishing/hair-growing effect. The present invention provides a hair growth agent comprising cyclic phosphatidic acid or carbacyclic phosphatidic acid as an active ingredient.

Description

Hair tonic

The present invention relates to a hair growth agent comprising as an active ingredient the cyclic phosphatidic acid or carba cyclic phosphatidic acid.

The alopecia, congenital, include the acquired, its pathogenesis have been made pathogenesis together many studies. But today, although the hair grower is exits in so many markets, at present, there are many unclear points.

Conventionally, in many upbringing hair dyes used in the prevention and treatment of alopecia, the medical component, assembly extract, vasodilators such as vitamin E acetate, stimulants such as capsicum tincture, pantothenic acid, biotin, etc. vitamins, further, hormonal agents, anti-inflammatory agents, disinfectants and the like are used. Further, it is also known to lysophosphatidic acid or phosphatidic acid derivative has custody bristles action (Patent Documents 1 and 2). Besides, nurturing hair agent containing hyaluronic acid synthesis promoting component is known (Patent Document 3).

However, the effect of these parenting hair dye is not necessarily high, there is a problem that does not give the results that always satisfactory to the user. Recently, with the advancement of technology, and nurturing hair dyes it is desired to further excellent rearing hair effect.

JP-B-63-41363 JP International Publication WO2001 / 012141 JP 2003-81778 JP

The present invention is to solve the problems in the prior art described above, the problem to be solved is to provide a hair growth agent exhibiting excellent hair tonic, hair growth effect.

The present inventors have found that cyclic phosphatidic acid and derivatives thereof, found to exhibit excellent hair tonic, hair growth effect, and have completed the present invention.

That is, according to the present invention, hair growth agent is provided which contains a compound represented by the following formula (1) as an active ingredient.

Figure JPOXMLDOC01-appb-C000002
(Wherein, R represents a linear or branched alkyl group having 1 to 30 carbon atoms, linear or branched alkenyl group having 2 to 30 carbon atoms, or C 2-30 linear or branched alkynyl group, each of these groups are good .X and Y also contain a cycloalkane ring or an aromatic ring independently represent an oxygen atom or a methylene group, X and Y is a methylene group at the same time no .M is a hydrogen atom or an alkali metal atom.)

Preferably, in formula (1), X and Y are oxygen atoms.
Preferably, in formula (1) is one oxygen atom of X or Y, the other is a methylene group.
Preferably, the compound of formula (1) is a compound having an acyl group consisting of fatty acids derived from soybean lecithin.

Further according to the present invention, a compound represented by the formula (1), comprising administering to a subject, hair growth method is provided.

Further according to the present invention, for the manufacture of a hair tonic, use of the compound represented by the formula (1) is provided.

According to the present invention, it is possible to provide a hair growth agent exhibiting excellent hair tonic, hair growth effect.

Figure 1 shows the change in hair growth score of the control group and NcPA administered group. Figure 2 shows a hair growth state of the administration 25 days in the control group. Figure 3 shows a hair growth state of the administration 25 days NcPA administration group.

Will be more specifically described the present invention.
Hair growth stimulant of the present invention can be used, for example in the treatment of male pattern baldness, comprising as active ingredient a cyclic phosphatidic acid or carba cyclic phosphatidic acid or their salts. As the cyclic phosphatidic acid or carba cyclic phosphatidic acid or salt thereof is not particularly limited as long as it shows the effects of the present invention can be preferably used a compound represented by the following formula (I).

Figure JPOXMLDOC01-appb-C000003

(Wherein, R represents a linear or branched alkyl group having 1 to 30 carbon atoms, linear or branched alkenyl group having 2 to 30 carbon atoms, or C 2-30 linear or branched alkynyl group, each of these groups are good .X and Y also contain a cycloalkane ring or an aromatic ring independently represent an oxygen atom or a methylene group, X and Y is a methylene group at the same time no .M is a hydrogen atom or an alkali metal atom.)

In the formula (I), specific examples of the linear or branched alkyl group substituents having 1 to 30 carbon atoms R exhibits, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group , heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group.

Specific examples of the linear or branched alkenyl group having 2 to 30 carbon atoms represented by the substituent R, for example, include an allyl group, a butenyl group, octenyl group, decenyl group, dodecadienyl group, such as hexamethylene tetradecatrienyl group is, more specifically, 8-decenyl, 8-undecenyl, 8-dodecenyl, 8-tridecenyl, 8-tetradecenyl, 8-pentadecenyl, 8-hexadecenyl, 8-heptadecenyl, 8 octadecenyl, 8-icosenyl, 8-docosenyl, heptadeca-8,11-dienyl group, heptadeca -8,11,14- trienyl group, nonadeca -4,7,10,13- tetraenyl group, nonadeca -4, 7,10,13,16- Pentaeniru groups, like Henikosa -3,6,9,12,15,18- Hekisaeniru based on It is.

Specific examples of the linear or branched alkynyl group having 2 to 30 carbon atoms represented by the substituent R, for example, 8-decynyl group, 8-undecynyl group, 8-dodecynyl group, 8-tridecynyl group, 8-tetradecynyl group, 8-pentadecynyl group, 8-hexadecynyl group, 8-Heputadeshiniru group, 8-octadecynyl group, 8-Ikoshiniru group, 8-Dokoshiniru groups, and heptadeca-8,11-diynyl group.

The above alkyl group, alkenyl group or Specific examples of the cycloalkane ring which may be contained in the alkynyl group, for example, cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, and a cyclooctane ring. Cycloalkane ring may contain one or more heteroatoms, as such an example, an oxetane ring, a tetrahydrofuran ring, such as N- methylprolidine ring.

The above alkyl group, specific examples of the aromatic ring alkenyl group which may be contained in the alkynyl group, for example, a benzene ring, a naphthalene ring, a pyridine ring, a furan ring, and a thiophene ring.

Therefore, specific examples of the case where the substituent R is an alkyl group substituted with a cycloalkane ring, e.g., cyclopropylmethyl group, a cyclohexylethyl group, 8,9-methanolate such pentadecyl group.

Specific examples of the case where the substituent R is an alkyl group substituted by an aromatic ring, a benzyl group, phenethyl group, etc. p- pentylphenyloctyl group.

R is preferably a linear or branched alkyl group having a carbon number of 9-17, linear or branched alkenyl group having a carbon number of 9-17, or a linear or branched alkynyl of a carbon number of 9-17 a group. R is more preferably a linear or branched alkyl group having a carbon number of 9, 11, 13, 15, or 17, or a linear or branched alkenyl group having a carbon number of 9, 11, 13, 15 or 17 is there. R is particularly preferably a linear or branched alkenyl group having a carbon number of 9, 11, 13, 15 or 17.

Each independently X and Y in the compound represented by the formula (1), an oxygen atom (-O-) or a methylene group (-CH 2 -) show, X and Y do not represent a methylene group at the same time . That is, the combination of X and Y are the following three.
(1) X is an oxygen atom, Y is an oxygen atom.
(2) X is an oxygen atom, Y is a methylene group.
(3) X is a methylene group, Y is an oxygen atom.

M in the cyclic phosphatidic acid derivative represented by the formula (I) is a hydrogen atom or an alkali metal atom. Examples of the alkali metal atom include lithium, sodium, and potassium and sodium is particularly preferred.

Specific examples of the compound represented by the formula used in the present invention (1), as 1-position acyl radical, R is stearoyl group having a carbon number of 17, oleoyl group, linoleoyl group, linolenoyl radical, R is the number of carbon atoms 15 palmitoyl groups, palmitoyl oleoyl group, or these fatty acids containing 2 or more, the cyclic phosphatidic acid derivatives with mixed fatty acid residues are preferred. Among them, cyclic phosphatidic acid derivative having an acyl group consisting of fatty acids derived from soybean lecithin is particularly preferable.

Compounds of formula (I) according to the type of the substituents, the position isomers, geometric isomers, tautomers, or in some cases such as optical isomers are present, all possible isomers, as well as mixtures comprising two or more of said different material elements in an arbitrary ratio are also within the scope of the present invention.

The compounds of formula (I) may exist in the form of water or adducts with various solvents (hydrates or solvates), these adducts also within the scope of the present invention is there. Furthermore, it is within the scope of any crystal form is also present invention compounds and salts thereof of formula (I).

Compounds X and Y are oxygen atoms among the compounds represented by formula (1) may, for example, JP-A 5-230088, JP-A No. 7-149772, JP-A No. 7-258278, JP-A No. 9 it can be chemically synthesized according to the method described in -25235 JP.

The compounds X and Y are oxygen atoms among the compounds represented by formula (1) is synthesized by the action of phospholipase D to lyso-type phospholipids according to the method described in JP-A-2001-178489 it is also possible to. Lyso phospholipid used herein is not particularly limited as long as lyso phospholipids which can act phospholipase D. Lyso-type phospholipids are known many types, those fatty species are different, are known and molecular species having an ether or vinyl ether bonds, which are available commercially. The phospholipase D, those and Streptomyces chromofuscus of from higher plants such as cabbage and peanut, but those derived from microorganisms such as Actinomadula sp. Are available as commercial reagents, very selectively by Actinomadula sp. No.362 enzyme from cyclic phosphatidic acid is synthesized manner (JP-a-11-367032 specification). Reaction of the lyso phospholipid and phospholipase D is the enzyme is not specifically limited insofar as the conditions capable of expressing activity, for example, under heating from room temperature in acetate buffer containing calcium chloride (about pH 5 ~ 6) (preferably about 37 ° C.) carried out by reacting about 1 to 5 hours at. The resulting cyclic phosphatidic acid derivatives, according to the conventional method, the extraction can be purified by, column chromatography, thin-layer chromatography (TLC).

Also, X is an oxygen atom among the compounds represented by formula (1), compound Y is a methylene group, methods described in the literature (Kobayashi, S., Other, Tetrahedron Letters 34,4047-4050 (1993) can be synthesized in accordance with), also can be synthesized by the method described in International Publication No. WO2002 / 094,286. An example of a specific synthesis route is shown below.

Figure JPOXMLDOC01-appb-C000004

In the above, first, commercially available (R) - benzyl glycidyl ether (1) was activated with BF 3 · Et 2 O, reacting a lithio body obtained by the action of n-BuLi in methylphosphonic acid dimethyl ester in to obtain the alcohol (2).
The resulting alcohol, obtained by reacting at 80 ° C. using a pyridinium salt of the excess p- toluenesulfonic acid in toluene, cyclized product (3). The cyclized by hydrogenolysis using 20% Pd (OH) 2 -C in a hydrogen atmosphere is performed debenzylation (4). Using 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride as a condensing agent, to obtain the coupling body (5) is reacted with a fatty acid. Next, using bromotrimethylsilane as a nucleophile, located selectively remove only the methyl group, to obtain the cyclic phosphonate (6). This crowded transferred to a separatory funnel using ether, was added dropwise an aqueous solution of sodium hydroxide of a small amount of 0.02 N, to carry out a liquid separation operation, the desired compound extracted and purified as sodium salt (7).

Also, X is a methylene group among the compounds represented by the general formula (1), compound Y is an oxygen atom, synthesized by the method described in JP-A-2004-010582 JP or WO WO03 / one hundred and four thousand two hundred forty-six can do.

The hair-growing agent dosage form of the present invention, a compound formulated may dosage form of the following formula (1) is not particularly limited as long as pharmaceutical form applied to skin, for example, a suitable cosmetic base or formulated with a pharmaceutical base liquid, emulsion-like, can be used as a semi-solid or solid-like hair tonic. For added absorption, microcapsules or may be included in the liposome.

Further, the form of the hair restorer of the present invention is arbitrary, hair liquid, hair tonic, hair lotion, ointment, hair creams, mousses, gels, shampoos, rinses and the like, used in the present invention each suitable base it is added a cyclic phosphatidic acid derivative can be prepared by a conventional method.

Content of the cyclic phosphatidic acid derivative in the hair-growing agent of the present invention varies depending on the kind of cyclic phosphatidic acid derivatives, usually 0.01 to 5.0 wt%, preferably 0.01 to 3.0 wt%, more preferably, 0.1 to 1.0 wt%.

Suitable bases in the liquid dosage form, those which are usually employed in hair-growing agents, such as purified water, ethanol, polyhydric alcohols, and the like, may be added an additive as necessary.
The polyhydric alcohols, glycerol, 1,3-butylene glycol, propylene glycol, and the like.
As the additives, surfactants, vitamins, anti-inflammatory agents, fungicides, hormonal agents, crude drug extracts, tinctures such, cooling agents, humectants, keratolytic agents, antioxidants, sequestering agents, perfumes and the like mentioned It is.

The surfactant is not particularly limited, non-ionic, anionic, can be used cationic, amphoteric surface active agents as appropriate.

The vitamins, benzyl nicotinate, nicotinamide, D- pantothenyl alcohol, pantothenyl ethyl ether, biotin, pyridoxine hydrochloride, riboflavin, and the like.

The anti-inflammatory agent, dipotassium glycyrrhizinate, beta-glycyrrhetinic acid, allantoin, diphenhydramine hydrochloride, guaiazulene, 1-menthol and the like.
The fungicide, trichloro hydroxy diphenyl ether, hinokitiol, triclosan, chlorhexidine gluconate, phenoxyethanol, resorcin, isopropyl methyl phenol, azulene, salicylic acid, zinc pyrithione, benzalkonium chloride, photosensitive element No. 301, sodium mononitroguayacol like .

The hormonal agents, ethinyl estradiol, estrone, estradiol and the like.
The herbal extract, assembly extract, garlic extract, ginseng extract, aloe extract, cinchona, and the like.
As tinctures such, capsicum tincture, ginger tincture, cantharides tincture, and the like.
The freshener, capsicum tincture, 1-menthol, camphor and the like.

Humectants, L- pyrrolidone carboxylic acid, sodium hyaluronate, chondroitin sulfate, Cordyceps sinensis extract, saffron extract, and the like.
As the antioxidant, butyl hydroxy anisole, isopropyl gallate, propyl gallate, and the like erythorbic acid.
The sequestering agent, ethylenediamine tetraacetate or a salt and the like.

The perfume, orange oil, lemon oil, bergamot oil, lime oil, lemongrass oil, natural flavors and menthol lavender oil, rose oxide, linalool, citral, synthetic perfumes such as linalyl acetate and the like.

When using the above liquid dosage forms as sprays may be used combustible gas, incombustible gas. The combustible gas, LPG (liquefied petroleum gas), dimethyl ether and the like, as the non-combustible gas, nitrogen gas, carbon dioxide gas and the like.
The semi-solid or solid dosage forms of the base include vaseline, solid paraffin, vegetable oils, mineral oil, lanolin, waxes, macrogol and the like, said additives if necessary, an emulsifier such as lecithin, ethyl alcohol , it may be added to a lower alcohol such as isopropyl alcohol.

The dose of the hair-growing agent of the present invention varies depending on the subject's symptoms and method of administration, and such, adult per person, at a time, 0.1 ~ 250 mg as the compound represented by the formula (1), preferably 1 mg ~ 100 mg but several times from once a day, is administered transdermally.

The following examples illustrate the present invention by, but the present invention is not limited by the examples.

Production Example 1:
native cPA used in this example (hereinafter, also referred to as NCPA) are those prepared as follows (see Examples 1, 3 and 5 of Japanese Patent Application No. 2011-126901).
Soybean phospholipids (lecithin content: 70%) of 10g was dissolved in 1M acetate buffer of 100ml containing 0.3M calcium chloride (pH 6.5), was added Streptomyces-derived phospholipase A2 6000 units and the reaction stirred for 18 hours at 40 ° C.. After adjusting the reaction solution to pH2.5 to inactivate the enzyme and chloroform 100 ml, was added methanol 50ml to extract sufficient stirring mixture lipid components. Collected chloroform layer was vacuum to dryness on a rotary evaporator. The solid precipitate the phospholipids of acetone was added 100ml to remove free fatty acids. The precipitate 5g dissolved in chloroform 40 ml, addition of 1M acetate buffer (pH 5.5) 10 ml, while performing the reaction stirred for a further 18 hours at the addition to 40 ° C. phospholipase D from Akuchinomajura genus 1500 units It was. 3M sodium chloride 20ml reaction solution was subjected to 1 hour stirring at the addition to 40 ° C. The 0.1 M EDTA solution 20ml. After further stirred sufficiently with adding methanol of 20 ml, 3000 rotation, to collect the chloroform layer was centrifuged for 5 minutes. The solution to obtain a cyclic phosphatidic acid sodium salt 3.8g was vacuum to dryness on a rotary evaporator. The yield was 54.3% because the cyclic phosphatidic acid Na was obtained 3.8g 70% lecithin content (7 g in 10 g). Purity analysis of cyclic phosphatidic acid sodium salt, using silica gel plate, chloroform: methanol: acetic acid: 5% sodium disulfite after deployment by (100: 40:: 12 5, V / V), 5% copper acetate: 8% phosphoric acid: after a short time immersed air-dried to 2% sulfuric acid mixture was heated to about 10 minutes at 180 ° C., the resulting spot was carried out by a scanner (manufactured by Atto) method. That is, standard (97% purity) as a control, the spot of the thin layer chromatography was measured by a densitometer, and quantified by area ratio. The purity of the product in the cyclic phosphatidic acid sodium salt obtained in the above step was 54%.

The above cyclic phosphatidic acid sodium salt 500mg was dissolved in chloroform containing 10% methanol 5 ml, applied to a silica gel column, developed with the same solvent, was further developed with chloroform containing 20% ​​methanol, was fractionated in fractions of 10 ml. Collect check Fractions containing cyclic phosphatidic acid sodium salt by the above TLC method to obtain a powder 320mg of cyclic phosphatidic acid sodium salt was vacuum to dryness on a rotary evaporator. The purity of the cyclic phosphatidic acid sodium salt of the sample was 95%.

The fatty acid composition of the high-purity cyclic sodium phosphatidic acid obtained in the above was analyzed by gas chromatography method. It was dissolved in methanolic hydrochloric acid so that the sample 20 mg / ml, warmed for 30 minutes at 65 ° C. After returning to room temperature, water master builder, then thoroughly stirred mixed with hexane master builder. 3000 revolutions, and centrifuged for 5 min and analyzed the constituent fatty injected hexane layer 2μl the capillary column. Analysis is as follows.
Fatty acid content (%)
Palmitic acid 23.9
Stearic acid 5.4
Oleic acid 8.6
Linoleic acid 53.4
Linolenic acid 4.9
Other fatty acid 3.8

Test Example 1:
Using NcPA produced in Production Example 1 was carried hair growth effect test in mice.

(1) administering the analyte controls; 50% ethanol (ethanol and physiological saline as prepared in equal amounts)
Test substance: the physiological saline to prepare a 1% aqueous solution of NCPA, a 1% aqueous solution of the NCPA was diluted with ethanol, to thereby prepare a 0.5% concentration.

(2) the test animals and breeding conditions test, male C3H / HeNCrlCrlj used (hereinafter, C3H, SPF, Japan Charles River Co., Ltd.) a (18.8g ~ 23.6g). Animals were shaved back from the neck of the mice grouped 3 days ago (47-48 weeks old) to the tail (the flank is not included) with a razor with shaving foam. Animals, set temperature 23 ° C., set humidity 55%, light and dark each 12 hours, were housed in animal room maintained at ventilation rate (12 times / hour). Feed solid material (MF, lot number: 111206, Oriental Yeast Co., Ltd.) ad libitum, and drinking water ad libitum tap water.

(3) administration route of administration, and transdermal administration. Administration sample (control or test substance), were administered to the dorsal skin of mice with a micropipette, yelling coated lightly with a finger (control group: 10 rats; ten and NcPA administered group). Dosing solution volume was 100 [mu] l / site. The frequency of administration was once a day. The administration period, the administration start date and 1 day administration, was 24 days.

(4) visual observation of the determination shaving unit, grouping day (administered daily), for administration 5,7,10,13,16,19,22 and 25 days, based on the criteria shown in Table 1 below scored with score and calculating the average value ± standard deviation for each group. In addition, it was photographed for each group to score observation day. Photo shoot and score observation was carried out prior to administration.

Figure JPOXMLDOC01-appb-T000005

(5) The results are shown in Table 2 and Figure 1 the results of the scores observed for hair growth status. Further, the results of the mouse photography in FIGS.

Figure JPOXMLDOC01-appb-T000006

Table 2 and as shown in FIG. 1, 1100Myueru / site / day NcPA group given 24-day dermal the NcPA of, as compared to the control group, high tendency (P <0.1 to 19 days and 25 days of administration ) it was observed, hair growth-promoting effect of NcPA has been confirmed.

Claims (4)

  1. Hair growth agent containing as an active ingredient a compound represented by the following formula (1).
    Figure JPOXMLDOC01-appb-C000001
    (Wherein, R represents a linear or branched alkyl group having 1 to 30 carbon atoms, linear or branched alkenyl group having 2 to 30 carbon atoms, or C 2-30 linear or branched alkynyl group, each of these groups are good .X and Y also contain a cycloalkane ring or an aromatic ring independently represent an oxygen atom or a methylene group, X and Y is a methylene group at the same time no .M is a hydrogen atom or an alkali metal atom.)
  2. In the formula (1), X and Y is an oxygen atom, hair-growing agent according to claim 1.
  3. In the formula (1), one of X or Y is an oxygen atom, the other is a methylene group, hair growth agent according to claim 1.
  4. Compounds of formula (1) is a compound having an acyl group consisting of fatty acids derived from soybean lecithin, hair-growing agent according to any one of claims 1 to 3.
PCT/JP2013/062332 2012-04-27 2013-04-26 Hair growth agent WO2013161978A1 (en)

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SG11201406911RA SG11201406911RA (en) 2012-04-27 2013-04-26 Hair-growing agent
CN201380022119.2A CN104254317B (en) 2012-04-27 2013-04-26 Hair restorer
KR1020147032100A KR20150006852A (en) 2012-04-27 2013-04-26 Hair Growth Agent
JP2014512699A JP6074411B2 (en) 2012-04-27 2013-04-26 Hair tonic
HK15105548.9A HK1204935A1 (en) 2012-04-27 2015-06-11 Hair growth agent

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002363081A (en) * 2001-06-06 2002-12-18 Nof Corp Hyaluronic acid production-reinforcing agent and its use
JP2003081778A (en) * 2001-09-13 2003-03-19 Lion Corp Hair growing agent
JP2004010582A (en) * 2002-06-11 2004-01-15 Gencom Co Carbacyclic phosphatidic acid derivative
WO2011065480A1 (en) * 2009-11-26 2011-06-03 国立大学法人お茶の水女子大学 Nerve cell death inhibitor

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6341363B2 (en) * 1982-08-10 1988-08-17 Lion Corp
CA2380640A1 (en) * 1999-08-18 2001-02-22 Kyowa Hakko Kogyo Co., Ltd. Hair-growing agent
EP2098237B1 (en) * 2006-12-28 2012-08-29 Ochanomizu University Analgesic agent comprising cyclic phosphatidic acid derivative
JP2008208058A (en) * 2007-02-26 2008-09-11 Nof Corp Promoter of focal adhesion formation, and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002363081A (en) * 2001-06-06 2002-12-18 Nof Corp Hyaluronic acid production-reinforcing agent and its use
JP2003081778A (en) * 2001-09-13 2003-03-19 Lion Corp Hair growing agent
JP2004010582A (en) * 2002-06-11 2004-01-15 Gencom Co Carbacyclic phosphatidic acid derivative
WO2011065480A1 (en) * 2009-11-26 2011-06-03 国立大学法人お茶の水女子大学 Nerve cell death inhibitor

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KR20150006852A (en) 2015-01-19
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