WO2007046577A1 - External composition for hair growth - Google Patents
External composition for hair growth Download PDFInfo
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- WO2007046577A1 WO2007046577A1 PCT/KR2006/002412 KR2006002412W WO2007046577A1 WO 2007046577 A1 WO2007046577 A1 WO 2007046577A1 KR 2006002412 W KR2006002412 W KR 2006002412W WO 2007046577 A1 WO2007046577 A1 WO 2007046577A1
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- derivatives
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- oxide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/606—Nucleosides; Nucleotides; Nucleic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/673—Vitamin B group
- A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9794—Liliopsida [monocotyledons]
Definitions
- the present invention relates to a hair growth-promoting composition for external application, and more particularly to a hair growth-promoting composition for external application, which contains 4-pyrrolidine 2,6- diaminopyrimidine 1 -oxide and one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnico
- Human hairs are about 100,000-150,000 in number, and each individual hair grows and falls out through various cycles of the hair growth cycle. Hair undergoes three phases of growth: anagen, catagen and telogen.
- the anagen is a hair growth phase, and is followed by the catagen phase when the configuration of hair is maintained and, at the same time, the metabolic process thereof becomes slow.
- the telogen following the catagen is a phase when hair papilla becomes smaller and hair follicles become recessive, so that hair shafts are easy to shed out.
- This life cycle of hair can vary depending on various conditions, including nutritional status, medical history, heredity, physical constitution, hormone secretion and aging.
- minoxidil for external application approved by the USA FDA was reported to have, in addition to vasodilation function as the characteristic potassium channel opener thereof, activities to induce the anagen phase from the telogen phase of the hair cycle and to continuously maintain the induced anagen phase (British Journal of Dermatology. 2004; 150: 186-194).
- the prior patents relating to the hair growth effects of pyrimidine oxide derivatives encompass a broad range of derivative structures, including the structure of the previously known minoxidil drug, and the hair growth effect of each of the derivatives is considered general. Also, the prior patents do not disclose data on the hair growth effects (e.g., vasodilation) of minoxidil. [Disclosure] [Technical Problem]
- pyrimidine oxide derivatives a compound having pyrrolidine attached to position 6 of the basic chemical structure of pyrimidine oxide, described in the International Cosmetic Ingredient Dictionary to have a function of waving and straightening hair, has a potassium channel opening effect and the effect of promoting the proliferation of important dermal papillae cells that control the hair cycle.
- the present inventors applied the compound to mice in order to examine the hair growth effect of the compound and, as a result, found that 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide shows a potassium channel opening effect through antagonistic action against a potassium channel opening-inhibitory drug, and the effect of promoting the proliferation of dermal papillae cells, and has the effect of stimulating the transition from the telogen phase to the anagen phase of the hair cycle in mice having the telogen phase, thereby completing the present invention.
- 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide shows a potassium channel opening effect through antagonistic action against a potassium channel opening-inhibitory drug, and the effect of promoting the proliferation of dermal papillae cells, and has the effect of stimulating the transition from the telogen phase to the anagen phase of the hair cycle in mice having the telogen phase, thereby completing the present invention.
- the present invention provides a composition for external application, which contains 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide as an active ingredient, and thus inhibits general male-pattern or female-pattern hair loss and promotes hair growth. [Advantageous Effects]
- FIG. 1 is a graphic diagram showing the potassium channel opening effect of 4-pyrrolidine-2,6-diaminopyrimidine- 1 -oxide.
- FIG. 2 is a graphic diagram showing that 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide has the effect of promoting the proliferation of dermal papillae cells.
- FIG. 3 shows that 4-pynolidine-2,6-diaminopyrimidine-l -oxide has the effect of promoting hair growth in mice. [Best Mode]
- the present invention relates to a hair growth-promoting composition for external application, which contains 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide as an active ingredient, and thus has the effects of opening potassium channels and promoting the proliferation of hair follicle cells.
- 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide which is used in the present invention, is represented by Formula 1 below, belongs to pyrimidine oxide derivatives, and is used as a cosmetic component while the in vivo effect thereof is not known: [Formula 1]
- 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide When 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide according to the present invention is used for the promotion of hair growth, it can be used in an amount of 0.001-10 wt% based on the total weight of the composition depending on the intended use and formulation thereof.
- the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide is preferably used in an amount of 0.001-5 wt% in view of the solubility and formulation stability thereof.
- 4- pyrrolidine-2,6-diaminopyrimidine-l -oxide is not solubilized in a specific formulation or has a stability problem, it can aggregate crystals or can be modified, thus causing discoloration or odor variation.
- the composition for external application according to the present invention may contain, in addition to said 4-pyrrolidine-2,6-diaminopyrimidine- 1 -oxide, one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate.
- the content of this selective component in the composition is preferably 0.005-5 wt% based on the total weight of the composition
- the panthenol derivatives which can be used in the present invention, are generally pantothenic acid derivatives, and the pantothenic acid was found as an essential growth factor of yeast and is stable in a neutral solution, but has disadvantages in that it is destroyed in an acidic or alkaline solution and is particularly weak against heat.
- D-panthenol, D-ethylpanthenol or calcium D-pantothenate which are a vitamin precursor which are converted into vitamin B5 having a more stable structure, is used in the present invention.
- the effects of vitamin B5 are generally summarized based on D-panthenol, and the multiple effects thereof in the skin and hair are reported to result from the following three effects: 1) ability to penetrate relatively deep into the skin and hair; 2) ability to bind to the skin; and 3) conversion into pantothenic acid in the skin and hair to produce the effects of vitamin B5.
- D-panthenol When D-panthenol is used in an amount of 0.1-5% in the cosmetic field, it will be delivered deep into the dermis due to the high permeation ability thereof, and will have a moisturizing effect by influencing the water condition and distribution of the dermal layer due to the hygroscopic capacity thereof.
- panthenol is absorbed to be converted into pantothenic acid
- mice was treated with 10% D-panthenol as an ointment for 6 weeks and, as a result, hypochromia and hair loss were more effectively improved compared to the case of oral administration
- panthenol on skin epidermal cells in the healing of external wounds and burns were reported (Gartner F., Dtsch. Zahn GmbHl. Z, 1955, 10, 813-5, Cortesse J., G.M. de France, 1968, 75, 4171-4).
- the Thujae semen which can be used in the present invention, is the seed of Thuja orientalis (occidentalis) (Curpressaceae), is long oval or long cylindrical in shape, and has a length of 3-5 mm and a diameter of 2-3 mm.
- the Thujae semen has the effects of calming and nourishing the spirit, and smoothing the bowel movement (Introduction to Oriental Studies). It is known to contain a large amount of fatty oil.
- the Dong-Eui-Bo-Gam discloses that new hair grows when the mixture is applied on a bald portion, the mixture being prepared by powdering 20 g of each of Aconitum carmichaeli, Viticis Fructus and Thujae semen, mixing the powders in Korean black (Ogol) chicken oil, drying the mixture, storing the dried mixture in chinaware for 100 days in a sealed state, and taking out the stored mixture from the chinaware (Dong-Eui-Bo-Gam, Hair Section, Namsandang Publishing Co.). Also, Thujae semen shows 5 ⁇ - reductase inhibitory activity and also high hair growth activity in two animal models, and thus can be effectively used against hair loss by controlling androgen conversion (Journal of Dermatological Science (2003) 31, 91-98).
- the Swertia extract which can be used in the present invention, is an extract from Swertia japonica Makino, and is called “Senburi extract” in Japan. In Korea, it is called “Dang-yak” in the drug name, and “sseun-pul” of Swertia japonica Makino in the scientific name.
- This extract is a traditional drug which has been widely used in Japan against an abdominal pain, skin infection, insects and a cold.
- the Swertia extract usually contains 2- 4% swertiamarin, sertianolin, erythrocentaurin, swertianol, oleanolic acid and genitianine.
- the Swertia extract is known to contain glycosides, including swertiamarin, as main components, and is reported to increase skin temperature and promote hair growth, like cantharide and capsicum tincture, which are derived from animals and vegetables.
- the paper of Shuji Iwao (“about prospect of hair growth stimulants", Fragrance Journal (1996)) describes that the Swertia extract is a blood circulation promoter, which is the major component of commercial hair growth stimulants.
- components which can be contained in the inventive composition, include Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate.
- These compositions can be used without any special limitation as long as they have no safety problem. Also, the action mechanisms thereof have no problems.
- these components are used for the vasodilation function of commercial hair growth stimulants and the activation of hair follicle cells, and can be prepared using commercially available raw materials according to a known method.
- the external application composition containing 4-pyrrolidine-2,6- diaminopyridine-1 -oxide as an active ingredient can be formulated into hair tonic, scalp treatment, hair shampoo, hair cream, general ointment, skin lotion, milk lotion, eye cream, nourishing cream, massage cream, cleansing cream, cleansing foam or powder but the scope of the present invention is not limited thereto.
- Experimental Example 1> Potassium channel opening effect of 4-pyrrolidine- 2,6-diaminopyrimidine- 1 -oxide 5% bovine fetal serum and 100 IU penicillin were added to a DMEM medium containing phenol red, and the medium was added onto a 24-well multi- well culture plate. A mouse-derived fibroblast NIH3T3 cell line was dispensed onto the 24-well multi-well culture plate at a density of 10,000 cells/well.
- Potassium channel antagonist tolbutamide was added to the medium at a final concentration of 2.5 niM, and a 100-fold dilution of 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide (Proderma, Italy) was added to the medium at concentrations of 1 ⁇ M, 50 ⁇ M and 100 ⁇ M, and the medium was incubated at 37 ° C for 3 days. After the incubation, a solution of 0.2% MTT (3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) was added to the microtiter plate in an amount of 200 ⁇ i per well, and the culture medium was further incubated at 37 ° C for 3 days.
- MTT 3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide
- the produced formazane was dissolved in DMSO (dimethylsulfoxide).
- the absorbance of the dissolved formazane was measured at 570 nm using a microplate reader.
- the A- pyrrolidine-2,6-diaminopyrimidine-l -oxide suppressed the potassium channel- antagonistic action of the tolbutamide at each concentration to promote the proliferation of NIH3T3.
- the promotion results of the compound are shown in FIG. 1 in comparison with a control group (100%).
- the control group is a group untreated with potassium channel antagonist tolbutamide
- the negative control group is a group treated only with tolbutamide.
- the 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide did not show the hair growth-promoting effect resulting from the potassium channel opening effect as high as the level of the control group, but showed a high growth- promoting effect compared to the negative control group treated only with tolbutamide.
- Rat-derived dermal papillae cells cultured in DMEM (Dulbecco's)
- Modified Eagle's Media containing 2% bovine fetal serum were dispensed onto a 96-well multi-well culture plate at a density of 1,000 cells/well, and 10 ⁇ g/ml of each of minoxidil as a positive control group and 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide was the culture medium.
- the culture media were incubated at a temperature of 37 ° C for 48 hours. After the incubation, a solution of 0.2% MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-di ⁇ henyltetrazolium bromide) was added to the microtiter plate at a density of 50 ⁇ i per well, and the culture media were further incubated at 37°C for 4 hours.
- MTT 3-[4,5-dimethylthiazol-2-yl]-2,5-di ⁇ henyltetrazolium bromide
- the produced formazane was dissolved in DMSO (dimethylsulfoxide). The absorbance of the dissolved formazane was measured at 570 nm using a microplate reader.
- the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention showed a papillae cell proliferation capability equal to that of minoxidil, and the papillae cell proliferation capability of the group treated with the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide together with each of the sixteen components was higher than that of the group treated with the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide alone.
- the papillae cell proliferation capability of the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention was measured at varying concentrations of 0.1, 1 and 10 ppm in the same manner as described above, and the measurement results were compared with those of a control group (CTL) treated only with the DMSO solution to determine a relative difference in absorbance.
- CTL control group
- the measurement results are shown in FIG. 2.
- the papillae cell proliferation capability of the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide was increased in a dose-dependent manner.
- mice Test of hair growth effect of 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide in mice
- the dorsal hair of 47-53 -day-old mice (C57BL/6) was removed, and among the mice, mice having a clean back portion were selected.
- the selected mice were divided into 18 groups each consisting of 8 animals.
- the mouse groups were applied daily with 150 ⁇ H of each of the following substances for 21 days to test the hair growth effects of the substances: a negative control group consisting of water/ethanol/l,3-butyleneglycol (5/3/2); a composition obtained by dissolving 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide in the negative control vehicle to a concentration of 0.5 wt%; and a composition obtained by dissolving each of the following substances in said 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide-containing composition to a concentration of 1 wt%: Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), aden
- mice After 21 days, the mice were photographed to observe the growth of hair in the mice, and the weight of newly grown in the test groups was measured, and compared with that in the negative control group. The measurement results are shown in Table 2 and FIG. 3. [Table 2]
- the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention showed an increase of about 29 mg in hair weight compared to the group applied with the negative control group (water/ethanol/ 1,3 -bury leneglycol). Also, it could be observed that the group applied with the 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide together with each of the 16 kinds of components, which can be selectively used in the present invention, showed increased hair growth compared to the group treated with the 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide alone.
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Abstract
The present invention relates to a hair growth-promoting composition for external application. More particularly, it relates to a hair growth-promoting composition for external application, which contains 4-pyrrolidine 2,6- diaminopyrimidine 1 -oxide and one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate. Thus, the composition smoothly supplies nutrients necessary for hair growth through the vasodilation of blood vessels around hair follicles to promote the transition from the telogen phase to the anagen phase of the hair cycle and to maintain the anagen phase for a long period of time.
Description
[DESCRIPTION]
[Invention Title]
EXTERNAL COMPOSITION FOR HAIR GROWTH [Technical Field] The present invention relates to a hair growth-promoting composition for external application, and more particularly to a hair growth-promoting composition for external application, which contains 4-pyrrolidine 2,6- diaminopyrimidine 1 -oxide and one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate, so that the composition smoothly supplies nutrients necessary for hair growth through the vasodilation of blood vessels around hair follicles to promote the transition from the telogen phase to the anagen phase of the hair cycle and to maintain the anagen phase for a long period of time. [Background Art]
Various studies to treat hair loss and promote hair growth in men and women who suffer serious mental anguish due to genetic or environmental hair loss in the modern society attaching importance to beauty are being actively conducted worldwide.
Human hairs are about 100,000-150,000 in number, and each individual hair grows and falls out through various cycles of the hair growth cycle. Hair undergoes three phases of growth: anagen, catagen and telogen. The anagen is
a hair growth phase, and is followed by the catagen phase when the configuration of hair is maintained and, at the same time, the metabolic process thereof becomes slow. The telogen following the catagen is a phase when hair papilla becomes smaller and hair follicles become recessive, so that hair shafts are easy to shed out. This life cycle of hair can vary depending on various conditions, including nutritional status, medical history, heredity, physical constitution, hormone secretion and aging.
Among existing therapeutic agents for hair loss prevention, minoxidil for external application approved by the USA FDA was reported to have, in addition to vasodilation function as the characteristic potassium channel opener thereof, activities to induce the anagen phase from the telogen phase of the hair cycle and to continuously maintain the induced anagen phase (British Journal of Dermatology. 2004; 150: 186-194).
Also, an oral administration drug, called Finasteride (Propecia; MSD), which inhibits the action of 5-alpha-reductase to inhibit the production of dihydrotestosterone as potent male hormone, was approved by the USA FDA and is being marketed as a hair growth stimulant. However, the use thereof has been limited, because it is expensive and has been reported to have some side effects. Thus, there has been a continued demand for a drug, which shows hair growth promotion effects and has no side effects, compared to the two major drugs developed in the prior art.
The mechanism of hair growth promotion of minoxidil (2,4-diamino-6- piperidino-pyridine-3 -oxide), a pyrimidine derivative, is still not clearly established. This hair growth promotion effect of the compound is merely recognized to result from vasodilation resulting from a potassium channel opening effect found at the time of development of the drug.
Since then, the general potassium channel opening effects of various pyrimidine derivatives and novel compounds, and the resulting hair growth effects, have been reported (J Invest Dermatol 2005 124 (4):686-94), and technologies relating to the hair growth effects of various derivatives of pyrimidine oxide have been filed (e.g., US Patent Nos. 5,034,387 and 4,945,093). The prior patents relating to the hair growth effects of pyrimidine oxide derivatives encompass a broad range of derivative structures, including the structure of the previously known minoxidil drug, and the hair growth effect of each of the derivatives is considered general. Also, the prior patents do not disclose data on the hair growth effects (e.g., vasodilation) of minoxidil. [Disclosure] [Technical Problem]
Accordingly, the present inventors have found that, among pyrimidine oxide derivatives, a compound having pyrrolidine attached to position 6 of the basic chemical structure of pyrimidine oxide, described in the International Cosmetic Ingredient Dictionary to have a function of waving and straightening hair, has a potassium channel opening effect and the effect of promoting the proliferation of important dermal papillae cells that control the hair cycle. Thus, the present inventors applied the compound to mice in order to examine the hair growth effect of the compound and, as a result, found that 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide shows a potassium channel opening effect through antagonistic action against a potassium channel opening-inhibitory drug, and the effect of promoting the proliferation of dermal papillae cells, and has the effect of stimulating the transition from the telogen phase to the anagen phase of the hair cycle in mice having the telogen phase, thereby completing the present invention.
[Technical Solution]
The present invention provides a composition for external application, which contains 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide as an active ingredient, and thus inhibits general male-pattern or female-pattern hair loss and promotes hair growth. [Advantageous Effects]
4-pyrrolidine-2,6-diaminopyrimidine-l -oxide according to the present invention is used as an active ingredient in a preparation for external application and acts to promote hair growth. Thus, the composition for external application according to the present invention contains 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide as an active ingredient, and thus can have a potassium channel opening effect, leading to the effects of preventing hair loss and promoting hair growth. [Description of Drawings] FIG. 1 is a graphic diagram showing the potassium channel opening effect of 4-pyrrolidine-2,6-diaminopyrimidine- 1 -oxide.
FIG. 2 is a graphic diagram showing that 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide has the effect of promoting the proliferation of dermal papillae cells. FIG. 3 shows that 4-pynolidine-2,6-diaminopyrimidine-l -oxide has the effect of promoting hair growth in mice. [Best Mode]
The present invention relates to a hair growth-promoting composition for external application, which contains 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide as an active ingredient, and thus has the effects of opening potassium
channels and promoting the proliferation of hair follicle cells.
Hereinafter, the present invention will be described in further detail. 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide, which is used in the present invention, is represented by Formula 1 below, belongs to pyrimidine oxide derivatives, and is used as a cosmetic component while the in vivo effect thereof is not known: [Formula 1]
When 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide according to the present invention is used for the promotion of hair growth, it can be used in an amount of 0.001-10 wt% based on the total weight of the composition depending on the intended use and formulation thereof. The 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide is preferably used in an amount of 0.001-5 wt% in view of the solubility and formulation stability thereof. Generally, if 4- pyrrolidine-2,6-diaminopyrimidine-l -oxide is not solubilized in a specific formulation or has a stability problem, it can aggregate crystals or can be modified, thus causing discoloration or odor variation.
Also, the composition for external application according to the present invention may contain, in addition to said 4-pyrrolidine-2,6-diaminopyrimidine-
1 -oxide, one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate. The content of this selective component in the composition is preferably 0.005-5 wt% based on the total weight of the composition.
The panthenol derivatives, which can be used in the present invention, are generally pantothenic acid derivatives, and the pantothenic acid was found as an essential growth factor of yeast and is stable in a neutral solution, but has disadvantages in that it is destroyed in an acidic or alkaline solution and is particularly weak against heat. For this purpose, D-panthenol, D-ethylpanthenol or calcium D-pantothenate, which are a vitamin precursor which are converted into vitamin B5 having a more stable structure, is used in the present invention. The effects of vitamin B5 are generally summarized based on D-panthenol, and the multiple effects thereof in the skin and hair are reported to result from the following three effects: 1) ability to penetrate relatively deep into the skin and hair; 2) ability to bind to the skin; and 3) conversion into pantothenic acid in the skin and hair to produce the effects of vitamin B5. When D-panthenol is used in an amount of 0.1-5% in the cosmetic field, it will be delivered deep into the dermis due to the high permeation ability thereof, and will have a moisturizing effect by influencing the water condition and distribution of the dermal layer due to the hygroscopic capacity thereof. In the year 1943, H. Pfaltz indirectly found that panthenol is absorbed to be converted into pantothenic acid, and he reported that each of rats and mice was treated with 10% D-panthenol as an
ointment for 6 weeks and, as a result, hypochromia and hair loss were more effectively improved compared to the case of oral administration (Pfaltz H., Vitaminforschung, 1943, 13, 236-249). Also, the effects of panthenol on skin epidermal cells in the healing of external wounds and burns were reported (Gartner F., Dtsch. Zahnarztl. Z, 1955, 10, 813-5, Cortesse J., G.M. de France, 1968, 75, 4171-4). When panthenol is applied on hair, it will penetrate the hair shaft and the hair root, so that it will be present as an elastic film in the hair and be present as a thin layer surrounding the hair surface to retain water in the hair and to protect the hair from external drying. The Thujae semen, which can be used in the present invention, is the seed of Thuja orientalis (occidentalis) (Curpressaceae), is long oval or long cylindrical in shape, and has a length of 3-5 mm and a diameter of 2-3 mm. The Thujae semen has the effects of calming and nourishing the spirit, and smoothing the bowel movement (Introduction to Oriental Studies). It is known to contain a large amount of fatty oil. As described in the hair section of Dong- Eui-Bo-Gam (Korean traditional medical text), a mixture of Aconitum carmichaeli, Viticis Fructus and Thujae semen is known to grow a new moustache or hair. Specifically, the Dong-Eui-Bo-Gam discloses that new hair grows when the mixture is applied on a bald portion, the mixture being prepared by powdering 20 g of each of Aconitum carmichaeli, Viticis Fructus and Thujae semen, mixing the powders in Korean black (Ogol) chicken oil, drying the mixture, storing the dried mixture in chinaware for 100 days in a sealed state, and taking out the stored mixture from the chinaware (Dong-Eui-Bo-Gam, Hair Section, Namsandang Publishing Co.). Also, Thujae semen shows 5α- reductase inhibitory activity and also high hair growth activity in two animal models, and thus can be effectively used against hair loss by controlling
androgen conversion (Journal of Dermatological Science (2003) 31, 91-98).
Moreover, the Swertia extract, which can be used in the present invention, is an extract from Swertia japonica Makino, and is called "Senburi extract" in Japan. In Korea, it is called "Dang-yak" in the drug name, and "sseun-pul" of Swertia japonica Makino in the scientific name. This extract is a traditional drug which has been widely used in Japan against an abdominal pain, skin infection, insects and a cold. The Swertia extract usually contains 2- 4% swertiamarin, sertianolin, erythrocentaurin, swertianol, oleanolic acid and genitianine. The Swertia extract is known to contain glycosides, including swertiamarin, as main components, and is reported to increase skin temperature and promote hair growth, like cantharide and capsicum tincture, which are derived from animals and vegetables. The physical effect of skin temperature increase or the vasodilation of cholinergic drugs can stimulate blood flow for skin function. The paper of Shuji Iwao ("about prospect of hair growth stimulants", Fragrance Journal (1996)) describes that the Swertia extract is a blood circulation promoter, which is the major component of commercial hair growth stimulants.
In addition, components, which can be contained in the inventive composition, include Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate. These compositions can be used without any special limitation as long as they have no safety problem. Also, the action mechanisms thereof have no problems. However, these components are used for the vasodilation function of commercial hair growth stimulants and the activation of
hair follicle cells, and can be prepared using commercially available raw materials according to a known method.
The external application composition containing 4-pyrrolidine-2,6- diaminopyridine-1 -oxide as an active ingredient can be formulated into hair tonic, scalp treatment, hair shampoo, hair cream, general ointment, skin lotion, milk lotion, eye cream, nourishing cream, massage cream, cleansing cream, cleansing foam or powder but the scope of the present invention is not limited thereto.
For hair growth promotion resulting from vasodilation as described above, said 4-pyrrolidine-2,6-diaminopyrimidine-oxide can be suitably selected and used by a person skilled in the art without any particular difficulty. [Mode for Invention]
Hereinafter, the construction and effects of the present invention will be described in further detail with reference to Examples and Test Examples. It is to be understood, however, that these examples are illustrative only and the scope of the present invention is not limited thereto.
Experimental Example 1>: Potassium channel opening effect of 4-pyrrolidine- 2,6-diaminopyrimidine- 1 -oxide 5% bovine fetal serum and 100 IU penicillin were added to a DMEM medium containing phenol red, and the medium was added onto a 24-well multi- well culture plate. A mouse-derived fibroblast NIH3T3 cell line was dispensed onto the 24-well multi-well culture plate at a density of 10,000 cells/well. Potassium channel antagonist tolbutamide was added to the medium at a final concentration of 2.5 niM, and a 100-fold dilution of 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide (Proderma, Italy) was added to the medium at
concentrations of 1 μM, 50 μM and 100 μM, and the medium was incubated at 37 °C for 3 days. After the incubation, a solution of 0.2% MTT (3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) was added to the microtiter plate in an amount of 200 μi per well, and the culture medium was further incubated at 37 °C for 3 days. Then, the produced formazane was dissolved in DMSO (dimethylsulfoxide). The absorbance of the dissolved formazane was measured at 570 nm using a microplate reader. The A- pyrrolidine-2,6-diaminopyrimidine-l -oxide suppressed the potassium channel- antagonistic action of the tolbutamide at each concentration to promote the proliferation of NIH3T3. The promotion results of the compound are shown in FIG. 1 in comparison with a control group (100%). In FIG. 1, the control group is a group untreated with potassium channel antagonist tolbutamide, and the negative control group is a group treated only with tolbutamide. As can be seen in FIG. 1, the 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide did not show the hair growth-promoting effect resulting from the potassium channel opening effect as high as the level of the control group, but showed a high growth- promoting effect compared to the negative control group treated only with tolbutamide.
Experimental Example 2>: Test of effect on promotion of dermal papillae cells
Rat-derived dermal papillae cells cultured in DMEM (Dulbecco's
Modified Eagle's Media) containing 2% bovine fetal serum were dispensed onto a 96-well multi-well culture plate at a density of 1,000 cells/well, and 10 μg/ml of each of minoxidil as a positive control group and 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide was the culture medium. Also, each of 10 μg/ml
of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate was added to the culture medium together with said 4- pyrrolidine-2,6-diaminopyrimidine-l -oxide. Then, the culture media were incubated at a temperature of 37 °C for 48 hours. After the incubation, a solution of 0.2% MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diρhenyltetrazolium bromide) was added to the microtiter plate at a density of 50 βi per well, and the culture media were further incubated at 37°C for 4 hours. The produced formazane was dissolved in DMSO (dimethylsulfoxide). The absorbance of the dissolved formazane was measured at 570 nm using a microplate reader. The measurement results for the test groups were compared with a control group treated only with the DMSO solution to measure a difference in absorbance between the test groups containing the 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide, and the results are shown in Table 1 below. [Table 1 ]
As can be seen in Table 1 above, the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention showed a papillae cell proliferation capability equal to that of minoxidil, and the papillae cell proliferation capability of the group treated with the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide together with each of the sixteen components was higher than that of the group treated with the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide alone.
Also, the papillae cell proliferation capability of the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention was measured at varying concentrations of 0.1, 1 and 10 ppm in the same manner as described above, and the measurement results were compared with those of a control group (CTL) treated only with the DMSO solution to determine a relative difference in absorbance. The measurement results are shown in FIG. 2. As can be seen in FIG. 2, the papillae cell proliferation capability of the 4-pyrrolidine-2,6-
diaminopyrimidine-1 -oxide was increased in a dose-dependent manner.
Experimental Example 3>: Test of hair growth effect of 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide in mice The dorsal hair of 47-53 -day-old mice (C57BL/6) was removed, and among the mice, mice having a clean back portion were selected. The selected mice were divided into 18 groups each consisting of 8 animals. The mouse groups were applied daily with 150 μH of each of the following substances for 21 days to test the hair growth effects of the substances: a negative control group consisting of water/ethanol/l,3-butyleneglycol (5/3/2); a composition obtained by dissolving 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide in the negative control vehicle to a concentration of 0.5 wt%; and a composition obtained by dissolving each of the following substances in said 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide-containing composition to a concentration of 1 wt%: Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives (tocopherol acetate, etc.), adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate.
After 21 days, the mice were photographed to observe the growth of hair in the mice, and the weight of newly grown in the test groups was measured, and compared with that in the negative control group. The measurement results are shown in Table 2 and FIG. 3. [Table 2]
As can be seen in Table 2 above, the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention showed an increase of about 29 mg in hair weight compared to the group applied with the negative control group (water/ethanol/ 1,3 -bury leneglycol). Also, it could be observed that the group applied with the 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide together with each of the 16 kinds of components, which can be selectively used in the present invention, showed increased hair growth compared to the group treated with the 4-pyrrolidine-2,6-diaminopyrimidine-l- oxide alone.
From the results of Table 2, it could be seen that the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide according to the present invention acted on the mice in the telogen phase to stimulate the transition to the anagen phase of the hair cycle, thus promoting hair growth in the mice.
Hereinafter, various formulation examples will be given based on the results of said Test Examples. It will however be obvious to those skilled in the art that these formulation examples are presented to explain the present invention and are not to be construed to limit the scope of the present invention. <Formulation Example 1>: Hair tonic [Table 3]
<Formulation Example 2>: Hair lotion [Table 4]
<Formulation Example 3>: Hair nourishing lotion [Table 5]
<Formulation Example 4>: Skin lotion [Table 6]
<Formulation Example 5>: Milk lotion [Table 7]
<Formulation Example 7>: Massage cream [Table 9]
<Formulation Example 8>: Pack [Table 10]
Claims
[CLAIMS]
[Claim 1 ]
An external composition for hair growth-promoting, comprising as active ingredients 4-pyrrolidine-2,6-diaminopyrimidine-l -oxide and one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts (glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives, adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate. [Claim 2]
The composition of Claim 1, which is a potassium channel opening composition for the vasodilation of blood vessels and the promotion of blood circulation at the intracellular level. [Claim 3]
The composition of Claim 1, which is a composition for promoting the proliferation of hair follicle cells. [Claim 4]
The composition of Claim 1, wherein the 4-pyrrolidine-2,6- diaminopyrimidine-1 -oxide) is contained in an amount of 0.001-10 wt% based on the total weight of the composition. [Claim 5]
The composition of Claim 1 , wherein said one or more selected from the group consisting of Thujae semen, vitamin B5 derivatives (panthenol derivatives), Swertia extract (Swertiall), Coicis semen, Glycyrrhiza extracts
(glycyrrhizin and glycyrrhetic acid), nicotinamide (niacinamide), vitamin E derivatives, adenosine, glyceryl pentadecanoate (PDG), 6-benzyl aminopurine, eugenol, saw palmetto, dialkylmonoamine derivatives, isoflavone, hinokitiol and benzylnicotinate are contained in an amount of 0.005-5 wt% based on the total weight of the composition. [Claim 6]
The composition of Claim 1 , which is formulated into a form selected from the group consisting of hair tonic, scalp treatment, hair shampoo, hair cream, general ointment, skin lotion, milk lotion, eye cream, nourishing cream, massage cream, cleansing cream, cleansing foam and powder.
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WO2010054343A2 (en) * | 2008-11-10 | 2010-05-14 | The Procter & Gamble Company | Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair |
WO2010054343A3 (en) * | 2008-11-10 | 2011-06-09 | The Procter & Gamble Company | Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair |
ES2444273A1 (en) * | 2012-08-22 | 2014-02-24 | Lacer, S.A. | Topical pharmaceutical or cosmetic composition indicated to reduce or prevent hair loss and stimulate hair growth (Machine-translation by Google Translate, not legally binding) |
JP2015078134A (en) * | 2013-10-15 | 2015-04-23 | 株式会社プロテックス・ジャパン | Scalp and hair cosmetic compositions |
JP2015101557A (en) * | 2013-11-25 | 2015-06-04 | 株式会社 日本天然物研究所 | Hair tonic obtained by adding a percutaneous absorption improver into minoxidil derivative, and production method thereof, as well as hair restoration system |
WO2016046848A3 (en) * | 2014-09-26 | 2016-05-26 | Brillare Science Pvt Ltd. | Novel formulation of concentrated natural actives in oil-water microemulsion for hair fall prevention and increase in hair density |
WO2017021247A1 (en) * | 2015-07-31 | 2017-02-09 | Isdin, S.A. | Anti-hair loss lotion |
US20180311130A1 (en) * | 2015-07-31 | 2018-11-01 | Isdin, S.A. | Anti-hair loss lotion |
CN114177124A (en) * | 2022-01-11 | 2022-03-15 | 佛山市艾诗摩尔网络科技有限公司 | Formula of hair nourishing essence for promoting hair growth and preventing hair loss and storage and use methods thereof |
Also Published As
Publication number | Publication date |
---|---|
KR20070041890A (en) | 2007-04-20 |
KR100992565B1 (en) | 2010-11-08 |
CN101291651A (en) | 2008-10-22 |
CN101291651B (en) | 2011-05-18 |
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