WO2009150902A1 - 外用組成物 - Google Patents
外用組成物 Download PDFInfo
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- WO2009150902A1 WO2009150902A1 PCT/JP2009/058022 JP2009058022W WO2009150902A1 WO 2009150902 A1 WO2009150902 A1 WO 2009150902A1 JP 2009058022 W JP2009058022 W JP 2009058022W WO 2009150902 A1 WO2009150902 A1 WO 2009150902A1
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- oil
- composition
- component
- skin
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
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- A61K36/75—Rutaceae (Rue family)
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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
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- 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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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
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- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
Definitions
- the present invention relates to an external composition
- an external composition comprising an essential oil and a purine base and / or a salt thereof.
- Examples of the skin aging phenomenon include pigmentation such as spots, freckles, and liver spots, dullness, dryness, wrinkles and the like. Preventing such skin aging is a great health and beauty concern especially for women.
- Essential oils are known as organic compounds containing volatile aromatic substances contained in plants. In addition to its use as a perfume, essential oils are known for antibacterial and antifungal effects, periodontal disease prevention effects (see Patent Document 1), and the like. However, little is known about the effects of applying essential oils to the skin.
- O / W type compositions containing adenine and the like are known as means for improving skin aging (see Patent Documents 2 and 3).
- Purine bases are known to promote skin turnover by increasing intracellular ATP levels and to prevent pigmentation such as spots and liver spots.
- IGF-1 insulin-like growth factor-1
- purine bases are not known to promote IGF-1 secretion.
- the skin consists of the epidermis on the surface, the dermis in the deep layer, and the subcutaneous tissue.
- the outermost layer of the epidermis has a stratum corneum.
- the stratum corneum created by epidermal cells is a barrier that separates the external environment from the inside of the body, and the quality of the stratum corneum is an extremely important factor that determines the freshness of the skin.
- the stratum corneum contains intercellular lipids, natural moisturizing factor (NMF), etc., and not only prevents moisture transpiration from the inside of the skin, but also the stratum corneum itself retains moderate moisture, Maintains the softness and smoothness.
- NMF natural moisturizing factor
- the “stratum corneum water amount” representing the water retention ability of the stratum corneum or “transepidermal water loss (TEWL) which is the amount of water evaporated from the stratum corneum surface” Loss) "is used.
- TEWL transepidermal water loss
- the skin As the skin ages, the skin is characterized by atrophy of the epidermis, thickening of the stratum corneum, and disappearance of the granular layer present under the stratum corneum. Aged skin exhibiting such characteristics has a lower stratum corneum moisture content and lower TEWL than young skin. It is known that such aging skin causes the skin surface to become rough as the outside air dries, and is accompanied by shallow cracks and itching. With conventional skin creams, the amount of skin transpiration can be suppressed by protecting the stratum corneum surface, and a temporary increase in the amount of stratum corneum moisture can be expected, but the effect was immediately lost when the use was stopped.
- the main object of the present invention is to provide a composition for external use that can enhance the secretion promoting action of IGF-1. Moreover, the composition for external use which can increase the amount of skin stratum corneum moisture and can maintain the amount of transepidermal water loss in an appropriate state is also provided.
- the present invention provides the following external composition, method for producing the external composition, and method for promoting IGF-1 secretion in the skin.
- Item 1 External composition containing the following component (A) and component (B): (A) essential oil; (B) At least one selected from the group consisting of purine bases and salts thereof.
- the component (A) is at least one essential oil selected from the group consisting of Daiki Oyster Oil, Ohihiba Oil, Atlas Cider Oil, Labandula Hybrida Oil, Lime Oil, Pepper Oil, Scots Pine Oil, Rosemary Oil and Turpentine Oil Item 2.
- composition for external use according to Item 1 or 2 wherein the component (A) is at least one essential oil selected from the group consisting of Daiki Oka oil, Scots pine oil and Labandula hybrida oil.
- Item 4. The composition for external use according to any one of Items 1 to 3, wherein the component (A) is an essential oil comprising a mixture of Daiki Oka oil, Scots pine oil and Labandula hybrida oil.
- Item 5. is an essential oil comprising a mixture of Daiwyo Oil, Ohihiba Oil, Atlas Cider Oil, Labandula Hybrida Oil, Lime Oil, Pepper Oil, Red Pine Oil, Rosemary Oil and Turpentine Oil The external composition in any one.
- Item 6. Item 6.
- Item 7. The composition for external use according to any one of Items 1 to 6, wherein the component (B) is adenosine 5′-monophosphate or a salt thereof.
- Item 8. The composition for external use according to any one of Items 1 to 7, wherein the proportion of component (A) is 0.00001 to 40% by weight.
- Item 9. Item 9. The composition for external use according to any one of Items 1 to 8, wherein the blending ratio of the component (B) is 0.01 to 20% by weight.
- Item 10. Item 10.
- Item 11. The composition for external use according to any one of Items 1 to 10, which is for promoting IGF-1 secretion in the skin.
- Item 12. The composition for external use according to any one of Items 1 to 10, which is used to increase the amount of stratum corneum moisture in the skin.
- Item 14. Item 14.
- composition for external use according to any one of Items 1 to 13, which is in the form of cosmetics or quasi drugs.
- Item 15. The following (A) component and (B) component (A) essential oil; (B) A method for producing an external composition for promoting IGF-1 secretion, comprising at least one selected from the group consisting of purine bases and salts thereof.
- Item 16. Use of the following components (A) and (B) for producing a composition for promoting IGF-1 secretion in the skin: (A) essential oil; (B) At least one selected from the group consisting of purine bases and salts thereof.
- Item 19 An external composition containing capsaicin and at least one selected from the group consisting of purine bases and salts thereof.
- the capsaicin is selected from the group consisting of capsaicin ((6E) -N-[(4-Hydroxy-3-methoxyphenyl) methyl] -8-methylnon-6-enamide), nonyl acid vanillylamide (N-Vanillylnonanamide) and dihydrocapsiate Item 20.
- composition for external use of the present invention synergistically enhances the IGF-1 production-promoting action of essential oil by using a combination of essential oil and purine base and / or salt thereof, and remarkably promotes IGF-1 secretion in the skin.
- the composition for external use of the present invention has the effects of reducing pigmentation (decreasing melanin amount), increasing skin lightness (preventing dullness), promoting turnover, etc., and maintaining skin moisture, increasing flexibility, etc.
- the anti-aging effect can be effectively and multifaceted.
- the composition for external use of the present invention has an effect of increasing the moisture content of the stratum corneum and enhancing the softness and elasticity of the skin. Moreover, the composition for external use of this invention also has the effect
- TEWL transepidermal water loss
- the effect of improving the skin function can be expected by increasing the stratum corneum moisture content and increasing the lowered TEWL to keep the skin moisture content in an appropriate state. Can maintain skin. Therefore, the composition for external use of the present invention can also be used for the prevention / treatment of senile xeroderma.
- the composition for external use of the present invention it is possible to prevent itching, eczema, pimples and the like by suppressing the drying of the skin and maintaining the transepidermal water loss (TEWL) appropriately.
- TEWL transepidermal water loss
- the balance between the stratum corneum moisture amount and the transepidermal water loss amount can be adjusted to an appropriate state, the skin state is kept normal, and it is refreshing. Can keep skin. Adjustment here means to lead to a healthy skin condition by improving the state where the TEWL of the skin is reduced and maintaining it when it is in an appropriate state.
- the external composition for skin of the present invention contains the following essential oil (hereinafter sometimes referred to as component (A)) and purine base and / or a salt thereof (hereinafter sometimes referred to as component (B)). To do.
- component (A) essential oil
- component (B) purine base and / or a salt thereof
- essential oil used as component (A) in the present invention contains volatile and lipophilic aromatic substances obtained from plant flowers, leaves, fruits, roots, bark, etc. It refers to an extract, and preferably refers to an extract containing a volatile and lipophilic fragrance obtained from a plant leaf, fruit, root, bark or the like.
- the essential oil that can be used as the component (A) of the present invention is not particularly limited as long as the effect of the present invention is exhibited, and an essential oil obtained from each plant raw material can be used.
- Dailicou (Illicium verum) oil Foeniculum vulgare oil, Pimpinella anisum oil, Thuja occidentalis Linn. Oil, Cedrus atlantica Manetti oil, Labandula Hybirda oil, rant oil Mentha arvensis var. Etc.
- Daiwichi oil fennel oil, anise oil, scented oil, Atlas cedar oil, Labandula hybrida oil, lime oil, peppermint oil, pine oil, rosemary oil and turpentine oil
- Daiki Oyster Oil Fennel Oil, Anise Oil, Akamatsu Oil, and Labandula Hybrida Oil
- Daiki Oka Oil is particularly preferred.
- one type may be selected from the above essential oils, or two or more types may be arbitrarily selected and used.
- the mode of the combination is not particularly limited as long as the effect of the present invention is not impaired.
- preferable combinations include, for example, Daiwichi oil, fennel oil, anise oil, eucalyptus oil, Atlas cedar oil, Labandula hybrida oil, lime from the viewpoint of effect and aroma.
- a mixture of oil, mint oil, pine pine oil, rosemary oil and turpentine oil more preferably Daiwyo oil, scented oil, Atlas cedar oil, Labandula hybrida oil, lime oil, mint oil, pine pine oil, rosemary oil And a mixture of turpentine oils.
- the effect of the present invention is more remarkably achieved by using such a mixture of essential oils or an essential oil containing a mixture as the component (A).
- the parts of the various plant raw materials used when collecting the essential oil of the present invention are not particularly limited as long as a desired essential oil can be collected, and a part conventionally used according to the kind of plant is used. Can do.
- plant parts such as flowers, stems, leaves, tree branches, fruits, roots and the like of various plants, and the above-ground parts of the plants, and more preferably plant parts such as stems, leaves, tree branches, fruits, roots, etc. of each plant. , And above-ground parts of plants.
- an essential oil extracted from a fruit if it is a daikyo oil, a fennel oil and an anise oil.
- odorant oil it is preferably an essential oil extracted from branches and leaves.
- Atlas cedar oil it is preferably an essential oil extracted from the bark.
- Lavandula hybrida oil it is preferably an essential oil extracted from whole grass.
- lime oil it is preferably an essential oil extracted from fruits and peels.
- mint oil it is preferably an essential oil extracted from whole grass.
- pine oil it is preferably an essential oil extracted from leaves.
- it is rosemary oil it is preferable that it is the essential oil extracted from the leaf.
- turpentine oil it is preferably an essential oil extracted from Pinaceae trees.
- the essential oil used in the present invention can be collected according to a conventionally known method, and examples of the collecting method include a steam distillation method, an oil adsorption method, a solvent extraction method, and a pressing method. These essential oil collection methods can be appropriately selected based on the type of plant raw material used, the extraction site, and the nature of the essential oil to be obtained. In addition, various essential oils sold as commercial products can be obtained and used more easily, for example, from Ogi Pharmaceutical Co., Ltd., Shiseido Pharmaceutical Co., Ltd. it can.
- the blending ratio of the component (A) in the external composition of the present invention is not particularly limited as long as the effects of the present invention are exhibited.
- the total amount of the component (A) is 0.00001% by weight or more, preferably 0.00001 to 40% by weight. More preferred is 0.0001 to 30% by weight, and still more preferred is 0.0001 to 25% by weight.
- purine base and its salt As (B) component used in this invention, at least 1 sort (s) selected from the group which consists of a purine base and its salt is mentioned.
- the purine base refers to various derivatives having purine or purine nucleus as a skeleton (hereinafter referred to as purine base).
- the purine base used in the present invention is not particularly limited.
- adenine, guanine, hypoxanthine, xanthine, adenosine, guanosine, inosine adenosine phosphate [adenosine 2′-monophosphate, adenosine 3 ′ Monophosphate, adenosine 5′-monophosphate (AMP), cyclic adenosine 3 ′, 5′-monophosphate (cAMP), adenosine 5′-diphosphate (ADP), adenosine 5′-triphosphate (ATP)], phosphate ester of guanosine (guanosine 3′-monophosphate, guanosine 5′-monophosphate, guanosine 5′-diphosphate, guanosine 5′-triphosphate), adenylosuccinic acid, xanthine acid, Inosinic acid, flavin a
- adenosine monophosphate (adenosine 2′-monophosphate, adenosine 3′-monophosphate, AMP, cAMP) is preferable.
- AMP when used in combination with the component (A), has a more prominent effect on promoting the secretion of IGF-1, increases the stratum corneum water content, and further maintains the transepidermal loss water content appropriately.
- Preferred as the component (B) of the present invention Preferred as the component (B) of the present invention.
- the purine base salt used in the present invention is not particularly limited.
- salts of purine bases include salts with alkali metals such as sodium and potassium; alkaline earth metal salts such as calcium, magnesium and barium salts; salts with basic amino acids such as arginine and lysine; ammonium and tricyclohexyl Ammonium salts such as ammonium salts; salts with alkanolamines such as monoisopropanolamine, diisopropanolamine and triisopropanolamine; aliphatic dihydric alcohol derivatives such as aminomethylpropanol, aminomethylpropanediol and aminohydroxymethylpropanediol Can be mentioned. Of these, alkali metal salts are preferred.
- the component (B) used in the present invention is preferably adenosine monophosphate monosodium or adenosine monophosphate disodium.
- one type may be selected and used from the above component (B), or two or more types may be arbitrarily selected and used.
- the mode of the combination is not particularly limited as long as the effect of the present invention is not impaired.
- the blending ratio of the component (B) with respect to the total amount of the composition for external use of the present invention is, for example, 0.01% by weight or more, preferably 0.1 to 20% by weight, more preferably 0.1 to 10% by weight. Can be mentioned.
- the component (B) is a salt of a purine base
- the blending ratio is a value converted to the weight of the purine base.
- composition for external use of the present invention is not particularly limited as long as it contains the components (A) and (B), and there is no limitation on the mode of combination thereof.
- Component essential oil and (B) component: purine base and / or a salt thereof, for example, (A) component: Daiwichi oil, fennel oil, anise oil, scented oil, atlas seed (bark) oil, Laban Mixture of Dura hybrida oil, lime oil, peppermint oil, pine pine (leaf) oil, rosemary oil and turpentine oil and (B) component: adenosine phosphate ester or a salt thereof; (A) component: Daifenki oil, Essential oil obtained from at least one selected from the group consisting of fennel oil, anise oil, Scots pine oil and Labandula hybrida oil and component (B): a combination of AMP or a salt thereof ; (A) component: Daifyo oil, scented oil, Atlas cedar oil, Labandula hybrid
- the mixing ratio of the component (A) and the component (B) in the external composition of the present invention is not particularly limited, and the mixing ratio of the components (A) and (B) described above, the form of the composition, and the expectation It can set suitably according to the effect etc. which are carried out.
- the total amount of component (A) is 0.0000005 to 1000 parts by weight, preferably 0.000005 to 100 parts by weight, more preferably 0.000001 to 100 parts by weight, more preferably 1 part by weight of component (B)
- the range which becomes 0.0001-100 weight part can be mentioned.
- the component (B) is a salt of a purine base
- the blending ratio is a value converted to the weight of the purine base.
- composition for external use of the present invention is usually required to have a pH within a weakly acidic to neutral range, but is preferable from the viewpoint of hypoallergenicity to the skin and the effect of improving pigmentation. Is pH 5-7, more preferably pH 5.5-7.
- a pH adjuster can be blended with the external preparation for skin.
- the pH adjuster to be blended in this way is not particularly limited as long as it is weakly alkaline to alkaline and pharmaceutically or cosmetically acceptable. Examples include sodium hydroxide, L-arginine, aminomethylpropanediol, diisopropanolamine, triethanolamine and the like.
- composition for external use of the present invention in addition to the above components, various components or additives usually added to the preparation for external use as necessary, for example, surfactant, solubilizing component, fats and oils, polyhydric alcohol, thickening Agents, preservatives, bactericides, moisturizers, colorants, dispersants, antioxidants, metal sequestering agents, skin astringents, whitening agents, pigments, deodorants and fragrances can be blended.
- these components can be mix
- the external composition of the present invention is not particularly limited as long as it is prepared as a composition to be applied to the skin in an external form.
- the composition for external use of the present invention is blended with each of the above optional components as necessary, and further blended with other solvents and bases or carriers of commonly used external preparations as necessary, Prepare as external preparations in various desired forms such as paste, mousse, gel, liquid, emulsion, suspension, cream, ointment, sheet, stick, aerosol, spray, liniment, etc. be able to. These are prepared according to conventional methods in the art.
- the use of the external composition of the present invention is not particularly limited.
- the composition for external use of the present invention comprises: a skin external medicine; a skin external medicine; a makeup cosmetic such as a foundation, blusher, lip, mascara, eye shadow, eyeliner, white powder, sunscreen, emulsion, cream, Cosmetics such as basic cosmetics such as lotions, oils and packs; cleansing agents such as facial cleansers, cleansing and body cleaning agents; cleaning agents; detergents; bath preparations and other external preparations.
- the external composition of the present invention is used by applying to human skin.
- the amount and frequency of application of the external composition of the present invention For example, depending on the type / concentration of active ingredient, user's age, gender, symptom level, application form, expected level, etc. (Especially for pigmentation (stains); wrinkles); areas where skin dryness (such as elbows, knees, wrinkles, etc.); itching, eczema, pimples, etc. That's fine.
- an application part will not be specifically limited, It can apply to the whole body.
- the composition for external use of the present invention has an action of promoting IGF-1 secretion in the skin as shown in the test examples described below.
- IGF-1 insulin-like growth factor
- IGF-1 has a cell growth action in addition to an insulin-like effect (hypoglycemic action) and regulates cellular DNA synthesis. Therefore, by promoting the secretion of IGF-1 in the skin, the growth of skin cells is promoted, the diseases and symptoms of the skin epithelial layer are improved, and the healthy state of the skin is maintained.
- the external composition of the present invention can be used as an external composition for promoting IGF-1 secretion or a composition for promoting production of IGF-1.
- the composition for external use of the present invention can also be used as a composition for preventing skin aging, a composition for moisturizing, a composition for improving pigmentation, or a composition for whitening.
- the composition for external use of the present invention has an action of increasing the moisture content of the stratum corneum and softening the stratum corneum. Therefore, the external composition of the present invention can be used as an external composition for increasing the stratum corneum moisture content in the skin.
- the increase in the stratum corneum moisture content can be measured according to a conventionally known method.
- a measuring instrument such as SKICON-200 (manufactured by IBI S Co., Ltd.) can be used. According to such a measuring instrument, it is possible to evaluate the change in the stratum corneum moisture content using the electric conductivity ( ⁇ S) as an index.
- the composition for external use of the present invention has an action of appropriately maintaining the amount of transepidermal water loss.
- the transepidermal water loss represents the amount of water transferred from the inside of the skin to the outside of the body, and by keeping this moderate, it is possible to suppress dryness of the skin and prevent itching, eczema, pimples and the like.
- the composition for external use of the present invention in addition to the effect of increasing the stratum corneum moisture content, it has the effect of appropriately maintaining the transepidermal loss moisture content, so that the skin condition is kept normal, and the fresh skin Can be realized.
- the composition for external use of the present invention when applied to skin having a reduced transepidermal water loss (TEWL), the TEWL can be increased and maintained in an appropriate state. Moreover, when TEWL is in an appropriate state, maintaining it can lead to a healthy skin state. Therefore, the external composition of the present invention can be used as an external composition for increasing the amount of transepidermal water loss or an external composition for adjusting the amount of transepidermal water loss.
- the transepidermal water loss can be measured according to a conventionally known method. For example, a measuring instrument such as DermaLab (manufactured by Cortex Technology) can be used.
- the external composition of the present invention can also be used as an external composition for providing an appropriate amount of transepidermal water loss while maintaining a high stratum corneum water content.
- the composition for external use of this invention is useful for the function improvement of a stratum corneum based on such a function, and can keep a stratum corneum healthy.
- the composition for external use of the present invention is useful for improving the symptoms of aging skin (specifically, rough skin surface, shallow cracks, itching, etc.) in which the stratum corneum moisture content and transepidermal water loss have been reduced. In particular, it can be effectively applied to the prevention / treatment of diseases (for example, senile xerosis) caused by the stratum corneum having reduced water retention ability and barrier function.
- diseases for example, senile xerosis
- the present invention provides a method for promoting IGF-1 secretion in the skin, which comprises applying the above components (A) and (B) to the skin. Furthermore, the present invention provides a method for preventing / treating xeroderma senile based on the improvement effect of the moisture retention function of the skin by promoting the secretion of IGF-1.
- the application amount of each component in these methods can be appropriately set depending on the degree and range of symptoms, but is, for example, 1 to 5000 mg / day as the component (B) and divided into 2 to 3 times a day. It is preferable to apply.
- the present invention also provides a method for easily producing an external composition having an IGF-1 secretion promoting action by blending the above components (A) and (B) with other components as necessary.
- specific examples of each component, blending amounts, and the like are as described above.
- compositions of Other Embodiments As shown in the Examples below, the present inventors have demonstrated that IGF-1 secretion can be achieved by using capsaicins together with purine bases and / or salts thereof (component (B)). I found that it was promoted. Therefore, the present invention also provides an external composition containing the component (B) and capsaicins. However, the capsaicins described here are not included in the essential oil and are distinguished from each other because they do not have the scent and volatility that are characteristic of the essential oil.
- Capsaicins are known as hot pepper components, and include capsaicinoids (a general term for compounds in which a fatty acid is bonded to an acid amide in vanillylamine) and capsinoids (a general term for compounds in which a fatty acid is ester-bonded to vanillyl alcohol).
- capsaicinoids include capsaicin ((6E) -N-[(4-Hydroxy-3-methoxyphenyl) methyl] -8-methylnon-6-enamide), non-anilic acid vanillylamide (N-Vanillylnonanamide) which is a synthetic capsaicinoid. It is done.
- capsinoids include dihydrocapsiate.
- capsaicin and synthetic capsaicinoid are preferable. Capsaicin can be extracted from chili pepper as a raw material according to a known method, but more conveniently can be obtained commercially from Tokyo Chemical Industry Co., Ltd.
- the blending ratio of capsaicins with respect to the total amount of the composition for external use of the present invention is, for example, 0.000001% by weight or more, preferably 0.000001 to 0.01% by weight, and more preferably 0.000001 to 0.005% by weight.
- the above purine base and / or salt thereof can be used.
- the blending ratio of the component (B) and the capsaicins in the composition for external use of the present invention is not particularly limited as long as the effects of the present invention are exerted.
- the capsaicins are 0.00000005 to 1 weight per 1 part by weight of the component (B). Parts, preferably 0.00000005 to 0.1 parts by weight, more preferably 0.0000001 to 0.1 parts by weight.
- the component (B) is a salt of a purine base
- the blending ratio is a value converted to the weight of the purine base.
- composition for external use in the case of containing the component (B) and capsaicin
- form and application method of the composition are described in “1. It is as described in the column of “External Composition”.
- capsaicins are already known as IGF-1 secretion promoters
- the present invention achieves higher IGF-1 secretion promotion than that using capsaicins alone by using capsaicins and purine bases in combination. It is possible.
- the use concentration of capsaicins can be reduced.
- Test Example 1 IGF-1 secretion promoting effect by combination of essential oil and AMP (1)
- Test Example 1 400 ⁇ L of the test solution was applied to the back skin (3 cm ⁇ 5 cm) of a hairless mouse (Hos: HR-1, Nippon SLC Co., Ltd., female, 6-8 weeks old). After 30 minutes of application, the skin was collected, frozen and crushed, and the IGF-1 concentration in the skin was measured. Quantikine® Mouse IGF-1 Immunoassay (R & D Systems, Inc.) was used for the measurement of IGF-1 concentration.
- test group was as shown in Table 2 below, and the composition shown in Table 1 was used as the test solution.
- results are shown in FIG. 1a (mean value ⁇ standard error).
- Test 1-2 Secreted IGF-1 concentration was measured according to the method described in Test 1-1.
- the test groups were as shown in Table 3 below, and the compositions shown in Table 1 were used as test solutions.
- the results are shown in FIG. 1b (mean value ⁇ standard error).
- Test 1-3 Secreted IGF-1 concentration was measured according to the method described in Test 1-1.
- the test groups were as shown in Table 4 below, and the compositions shown in Table 1 were used as test solutions. The results are shown in FIG. 1c (mean value ⁇ standard error).
- AMP alone does not provide a sufficient IGF-1 secretion promoting effect, but in the compositions of Examples 1, 2 and 3, especially Examples 1 and 2, a remarkable secretion promoting action of IGF-1 It was shown to play.
- Dai fennel oil contains anethole as a main component.
- Anethole is also contained in fennel oil, anise oil, and the like, and therefore, even when fennel oil and anise oil are combined with AMP, excellent secretion promoting effect of IGF-1 is achieved as in the case of using daikyo oil. There is expected.
- Test Example 2 IGF-1 Secretion Promoting Effect by Combination of Nonyl Acid Warinylamide and AMP
- Example 1 shown in Table 1 above nonyl acid vanillylamide ((Tokyo Chemical Industry Co., Ltd.); concentration 0.001%) instead of essential oil
- a test solution was prepared in the same manner as in Test Example 1, and this was designated as Reference Example 1.
- the test liquid (Comparative Example 6) which does not contain nonylic acid valinylamide in Reference Example 1 and the test liquid (Comparative Example 7) which does not contain AMP in Reference Example 1 were used as controls.
- Test Example 3 IGF-1 secretion promoting effect by the combination of essential oil and AMP (2) 300 ⁇ L of the test solution was applied to the back skin (3 cm ⁇ 5 cm) of a hairless mouse (Hos: HR-1, Nippon SLC Co., Ltd., female, 7 weeks old). After 30 minutes of application, the skin was collected, frozen and crushed, and the IGF-1 concentration in the skin was measured. Quantikine® Mouse IGF-1 Immunoassay (R & D Systems, Inc.) was used for the measurement of IGF-1 concentration.
- test was a comparison between two groups with and without application.
- other test oils (Atlas cedar oil) had a favorable aroma as a preparation. )
- Essential oil mixture 0.03%
- AMP 1% a suitable general base material.
- Test Example 4 Effect on stratum corneum water content and transepidermal water loss (1)
- 9 healthy men and ages 30 to 55 years were used as subjects.
- a 5 ⁇ 8 cm region placed in front of the subject's left and right thighs was taken as the test site.
- the test solution was applied to one of the left and right test sites, and the other test site was not applied.
- the application amount is about 0.1g (2 drops of the used container) at a time, twice a day (AM / PM), and the application time is from 6:00 to 12:00.
- the afternoon application was after bathing from 18:00 to 24:00.
- skin milk having the composition shown in Table 7 below was used.
- the subject washed the measurement site (thigh) with a designated soap (Kao White; manufactured by Kao Corporation), and then marked the measurement site with an oil-based pen.
- a designated soap Kero White; manufactured by Kao Corporation
- the patient was rested for 20 minutes on his / her back on the bed. Thereafter, the stratum corneum water content and transepidermal water loss were measured. At this time, the uncoated portion was used as a control.
- the measurement was performed before the start of application, and after 4 weeks and 8 weeks after application. The results are shown in FIGS. 3a and 3b.
- the measurement of the stratum corneum water content, the measurement of transepidermal water loss, and data analysis were performed according to the following methods.
- ⁇ Corn layer moisture content> Using SKICON-200 (IBS Co., Ltd.), the electrical conductivity ( ⁇ S) was measured and used as an index of the stratum corneum moisture content. The measurement was carried out seven times, and the average value of the central five data was used as the measurement value.
- Transepidermal water loss (TEWL)> Measure transepidermal water loss (g / h ⁇ m 2 ) using DermaLab (Cortex Technology). The measurement was performed 5 times, and the average value was taken as the measured value.
- FIG. 3a From the results shown in FIG. 3a, it was shown that the stratum corneum water content increased significantly in 4 weeks and 8 weeks of application of the test solution. Moreover, FIG. 3b showed a significant increase in TEWL after 8 weeks of application of the composition for external use of the present invention, compared with no application.
- Flexibility and elasticity are measured using a Cutometer MPA580 (CK electronic GmbH). Measurements were performed by standard methods described in the instructions that came with the instrument. The measurement was performed 5 times, and the average value was taken as the measured value.
- the skin surface texture was evaluated by preparing a skin specimen sample.
- the skin specimen sample was evaluated using a replica analysis system ASA-03R (Asahi Biomed) for reflection, creating a replica of the skin surface form by the method described in the attached manual, photographing the image.
- ASA-03R Asahi Biomed
- Test Example 4 From the results of Test Example 4, it is shown that the combination of the above 9 kinds of essential oils and AMP is applied to the skin to keep the skin moisture content normal and to improve the flexibility and elasticity. It was done. In addition, by applying the composition for external use of the present invention to the skin, the skin surface became finer, and fresh and healthy skin was obtained.
- Test Example 5 Effect on stratum corneum water content and transepidermal water loss (2) In order to confirm that these effects were shown throughout the body, the following test was conducted. In this test example, 7 healthy men, age 39-57 years (average 49.0 years) were used as subjects. An area of 4 ⁇ 4 cm was placed on the left and right buttocks of the subject, and this was used as a test site. The test solution (cream formulation containing 0.5% AMP and 0.03% essential oil mixture) was applied to one of the left and right test sites, and the other test site was not applied. The application amount is about 0.2 g per application, twice a day (am / pm), and the application period is from 6:00 to 12:00 in the morning application and from 18:00 to 24 in the afternoon application period. After bathing until 0:00.
- the test solution cream formulation containing 0.5% AMP and 0.03% essential oil mixture
- Test Example 6 Effect on stratum corneum water content and transepidermal water loss (3)
- five healthy men, ages 47 to 57 years (average 53.2 years) were used as subjects.
- Two 4 ⁇ 4 cm regions were installed on the inner side of the left and right forearms of the subject, and these were used as test sites.
- Apply the test liquid skin milk used in Test Example 3 above
- commercially available general skin milk general preparation containing no adenosine monophosphate and essential oil in the other elbow side application part ) was applied.
- the application frequency was twice a day (am / pm), and the application time zone was from 6:00 to 12:00 in the morning application and after bathing from 18:00 to 24:00 in the afternoon application.
- the coating amount was about 0.05 g (one drop of the used container) at one time.
- the subject washed the measurement site (inner forearm) with a designated soap (Kao White; manufactured by Kao Corporation), then marked the measurement site with an oil-based pen, temperature 20 ° C, relative humidity In a room controlled to 50% RH, the patient was rested for 20 minutes on his / her back on the bed. Thereafter, the stratum corneum water content and transepidermal water loss (TEWL) were measured. The measurement was performed before the start of application and 4 weeks after application.
- a designated soap Kero White; manufactured by Kao Corporation
- test solution skin lotion
- general preparation skin lotion
- test solution skin lotion
- 2 is a graph showing the effects of essential oil (Daifenkou oil) and AMP on the amount of skin IGF-1 (in the figure, # represents P ⁇ 0.05).
- 2 is a graph showing the effects of essential oil (Acacia pine oil) and AMP on the amount of skin IGF-1 (in the figure, # represents P ⁇ 0.05).
- It is a graph which shows the effect
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Abstract
Description
項1.以下の(A)成分及び(B)成分を含有する外用組成物:
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種。
項2.(A)成分が、ダイウイキョウ油、ニオイヒバ油、アトラスシーダ油、ラバンデュラハイブリダ油、ライム油、ハッカ油、セイヨウアカマツ油、ローズマリー油及びテレビン油からなる群より選択される少なくとも1種の精油である、項1に記載の外用組成物。
項3.(A)成分が、ダイウイキョウ油、セイヨウアカマツ油及びラバンデュラハイブリダ油からなる群より選択される少なくとも1種の精油である、項1又は2に記載の外用組成物。
項4.(A)成分が、ダイウイキョウ油、セイヨウアカマツ油及びラバンデュラハイブリダ油の混合物を含む精油である、項1~3のいずれかに記載の外用組成物。
項5.(A)成分が、ダイウイキョウ油、ニオイヒバ油、アトラスシーダ油、ラバンデュラハイブリダ油、ライム油、ハッカ油、セイヨウアカマツ油、ローズマリー油及びテレビン油の混合物を含む精油である項1~4のいずれかに記載の外用組成物。
項6.(B)成分が、アデノシンのリン酸エステル又はその塩である、項1~5のいずれかに記載の外用組成物。
項7.(B)成分が、アデノシン5'-一リン酸又はその塩である、項1~6のいずれかに記載の外用組成物。
項8.(A)成分の配合割合が、0.00001~40重量%である、項1~7のいずれかに記載の外用組成物。
項9.(B)成分の配合割合が、0.01~20重量%である、項1~8のいずれかに記載の外用組成物。
項10.(B)成分1重量部に対する(A)成分の配合比率が、0.0000005~1000重量部である、項1~9のいずれかに記載の外用組成物。
項11.皮膚におけるIGF-1分泌促進用である、項1~10のいずれかに記載の外用組成物。
項12.皮膚における角層水分量増加用である、項1~10のいずれかに記載の外用組成物。
項13.皮膚における経表皮水分喪失量(TEWL)調節用である、項1~10のいずれかに記載の外用組成物。
項14.化粧料または医薬部外品の形態である、項1~13のいずれかに記載の外用組成物。
項15.下記(A)成分及び(B)成分
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種
を配合することを特徴とする、IGF-1分泌促進用外用組成物の製造方法。
項16.皮膚におけるIGF-1分泌促進用組成物の製造ための下記(A)成分及び(B)成分の使用:
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種。
項17.下記(A)成分及び(B)成分
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種
を皮膚に塗布することを特徴とする、皮膚におけるIGF-1分泌促進方法。
項18.下記(A)成分及び(B)成分
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種
を皮膚に塗布することを特徴とする、老人性乾皮症の予防/治療方法。
項19.カプサイシン類と、プリン塩基及びその塩からなる群より選択される少なくとも1種とを含有する外用組成物。
項20.カプサイシン類が、カプサイシン((6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide)、ノニル酸ワニリルアミド(N-Vanillylnonanamide)及びジヒドロカプシエイトからなる群より選択される少なくとも1種である、項19に記載の外用組成物。
本発明の皮膚外用組成物は、下記精油(以下(A)成分と表記することがある)及びプリン塩基及び/又はその塩(以下(B)成分と表記することがある)を含有する。以下、本発明の構成について詳述する。
本発明において(A)成分として使用される精油(エッセンシャル・オイル)とは、植物の花、葉、果実、根、樹皮等から得られる揮発性、親油性の芳香物質を含有する抽出液を指し、好ましくは植物の葉、果実、根、樹皮等から得られる揮発性、親油性の芳香物質を含有する抽出液を指す。
本発明において使用される(B)成分としては、プリン塩基及びその塩からなる群より選択される少なくとも1種が挙げられる。本発明においてプリン塩基とは、プリン又はプリン核を骨格とする各種の誘導体(以下、プリン塩基という)を指す。
本発明の外用組成物は、通常弱酸性~中性の範囲内のpHを備えていればよいが、皮膚に対する低刺激性、及び色素沈着改善効果の点からは、好ましくはpH5~7、更に好ましくはpH5.5~7である。本発明の外用組成物のpHを上記範囲に調整するために、該皮膚外用剤にpH調整剤を配合することができる。このように配合されるpH調整剤としては、弱アルカリ性~アルカリ性であって薬学的或いは香粧的に許容されるものであれば特に制限されない。一例として、水酸化ナトリウム、L-アルギニン、アミノメチルプロパンジオール、ジイソプロパノールアミン、トリエタノールアミン等を挙げることができる。
さらに本発明者らは、下記実施例において示されるように、カプサイシン類とプリン塩基及び/又はその塩((B)成分)とを併用することによってIGF-1の分泌が促進されることを見出した。従って、本発明は、上記(B)成分とカプサイシン類を含有する外用組成物をも提供する。ただし、ここで記すカプサイシン類とは、精油の特徴である香りや揮発性を有しないことから、精油には含まれず、区別されるものである。
皮膚におけるIGF-1分泌量に及ぼす精油の作用がAMPによりどのように影響されるかを検討するため、精油とAMPを含有する下記組成物(実施例1~3及び比較例1~5)を常法により調製した。各組成物のpHは、pH6.5~7.0になるようにNaOHで調整した。
[試験1-1]
ヘアレスマウス(Hos:HR-1,日本エスエルシー(株), 雌, 6~8週令)の背部皮膚(3 cm × 5 cm)に被験液を400μL塗布した。塗布30分後に皮膚を採取、凍結破砕した後、皮膚中IGF-1濃度を測定した。IGF-1濃度の測定にはQuantikine(登録商標) Mouse IGF-1 Immunoassay(R&D Systems, Inc.)を使用した。
試験1-1に記載の方法に従って、分泌されたIGF-1濃度を測定した。試験群は下記表3の通りとし、被験液には上記表1に示す組成物を用いた。結果を図1bに示す(平均値±標準誤差)。
試験1-1に記載の方法に従って、分泌されたIGF-1濃度を測定した。試験群は下記表4の通りとし、被験液には表1に示す組成物を用いた。結果を図1cに示す(平均値±標準誤差)。
上記表1に示される実施例1において精油の代わりに、ノニル酸ワニリルアミド((東京化成工業株式会社製);濃度0.001%)を用い、試験例1と同様に被験液を調製し、これを参考例1とした。また、参考例1においてノニル酸ワリニルアミドを含有しない被験液(比較例6)、参考例1においてAMPを含有しない被験液(比較例7)をそれぞれ対照として用いた。
ヘアレスマウス(Hos:HR-1,日本エスエルシー(株), 雌, 7週令)の背部皮膚(3 cm × 5 cm)に被験液を300μL塗布した。塗布30分後に皮膚を採取、凍結破砕した後、皮膚中IGF-1濃度を測定した。IGF-1濃度の測定にはQuantikine(登録商標) Mouse IGF-1 Immunoassay(R&D Systems, Inc.)を使用した。
本試験例は、健常男性9名、年齢30~55歳(平均45歳)を被験者として行われた。被験者の左右の大腿部正面に設置した5×8cmの領域を試験部位とした。左右一方の試験部位に試験液を塗布し、他方の試験部位は無塗布とした。塗布量は、1回につき約0.1g(使用した容器の2滴分)を、1日2回(午前・午後)とし、塗布時間帯は午前塗布を6:00から12:00までの間、午後塗布を18:00から24:00までの入浴後とした。試験液として、下記表7に示される組成のスキンミルクを用いた。
SKICON-200(アイ・ビイ・エス株式会社)を用いて電気伝導度(μS)を測定し角層水分量の指標とした。測定は7回実施し、中央の5データの平均値を測定値とした。
DermaLab(Cortex Technology)を用いて経表皮水分喪失量(g/ h・m2)を測定する。測定は5回実施し、その平均値を測定値とした。
有意差検定として、無塗布群に対する塗布群の差について、各測定日(塗布4週後、塗布8週後)での比較として対応のあるt検定を用いた。図中、#はP<0.05で有意差があったことを示す。
柔軟性及び弾力性はCutometer MPA580(CK electronic GmbH)を用いて測定する。測定は、機器に付属の説明書に記載される標準的な方法で実施した。測定は5回実施し、その平均値を測定値とした。
有意差検定として、無塗布群に対する塗布群の差について、各測定日(塗布4週後、塗布8週後)での比較として対応のあるt検定を用いた。図中、#はP<0.05で有意差があったことを示す。
皮膚表面きめの評価は、皮膚検体サンプルを作製して行った。皮膚検体サンプルは、反射用レプリカ解析システムASA-03R(アサヒバイオメッド)を用い、付属の説明書に記載される方法で皮膚表面形態のレプリカを作成し、画像撮影して評価した。
これらの効果が全身で示されることを確認する目的で、下記試験を実施した。本試験例は、健常男性7名、年齢39~57歳(平均49.0歳)を被験者として行われた。被験者の左右一方の踵部に4×4 cmの領域を設置し、これを試験部位とした。左右一方の試験部位に試験液(AMP0.5%と精油混合物0.03%を含むクリーム製剤)を塗布し、他方の試験部位は無塗布とした。塗布量は、1回につき約0.2gを、1日2回(午前・午後)とし、塗布時間帯は午前塗布を6:00から12:00までの間、午後塗布を18:00から24:00までの入浴後とした。
本試験例は、健常男性5名、年齢47~57歳(平均53.2歳)を被験者として行われた。被験者の左右の前腕内側部に4×4 cmの領域をそれぞれ2カ所ずつ(肘側と手首側)設置し、これを試験部位とした。左右一方の肘側塗布部位に試験液(上記試験例3で用いたスキンミルク)を塗布、他方の肘側塗布部にアデノシン一リン酸及び精油を含有しない市販の一般的なスキンミルク(一般製剤)を塗布した。塗布回数は1日2回(午前・午後)とし、塗布時間帯は午前塗布を6:00から12:00までの間、午後塗布を18:00から24:00までの入浴後とした。塗布量は1回につき約0.05g(使用した容器の1滴分)とした。
以下に本発明の外用組成物の処方例を示すが、本発明はこれらに限定されない。ローション、乳液及び美容液は、各処方例に示される組成に基づいて常法により調製することができる。なお、各処方例の合計量を100重量%として記載する。
Claims (13)
- 以下の(A)成分及び(B)成分を含有する外用組成物:
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種。 - (A)成分が、ダイウイキョウ油、ニオイヒバ油、アトラスシーダ油、ラバンデュラハイブリダ油、ライム油、ハッカ油、セイヨウアカマツ油、ローズマリー油及びテレビン油からなる群より選択される少なくとも1種の精油である、請求項1に記載の外用組成物。
- (A)成分が、ダイウイキョウ油、セイヨウアカマツ油及びラバンデュラハイブリダ油からなる群より選択される少なくとも1種の精油である、請求項1又は2に記載の外用組成物。
- (A)成分が、ダイウイキョウ油、セイヨウアカマツ油及びラバンデュラハイブリダ油の混合物を含む精油である、請求項1~3のいずれかに記載の外用組成物。
- (A)成分が、ダイウイキョウ油、ニオイヒバ油、アトラスシーダ油、ラバンデュラハイブリダ油、ライム油、ハッカ油、セイヨウアカマツ油、ローズマリー油及びテレビン油の混合物を含む精油である請求項1~4のいずれかに記載の外用組成物。
- (B)成分が、アデノシンのリン酸エステル又はその塩である、請求項1~5のいずれかに記載の外用組成物。
- (B)成分が、アデノシン5'-一リン酸又はその塩である、請求項1~6のいずれかに記載の外用組成物。
- (B)成分の配合割合が、0.01~20重量%である、請求項1~7のいずれかに記載の外用組成物。
- (B)成分1重量部に対する(A)成分の配合比率が、0.0000005~1000重量部である、請求項1~8のいずれかに記載の外用組成物。
- 化粧料、医薬部外品または医薬品の形態である、請求項1~9のいずれかに記載の外用組成物。
- 下記(A)成分及び(B)成分
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種
を配合することを特徴とする、皮膚におけるIGF-1分泌促進用外用組成物の製造方法。 - 皮膚におけるIGF-1分泌促進用組成物の製造ための下記(A)成分及び(B)成分の使用:
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種。 - 下記(A)成分及び(B)成分
(A)精油;
(B)プリン塩基及びその塩からなる群より選択される少なくとも1種
を皮膚に塗布することを特徴とする、皮膚におけるIGF-1分泌促進方法。
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- 2009-04-22 ES ES18150042T patent/ES2959848T3/es active Active
- 2009-04-22 KR KR1020097026200A patent/KR101746743B1/ko active IP Right Grant
- 2009-04-22 JP JP2009531683A patent/JP4403467B1/ja active Active
- 2009-04-22 CN CN2009801009462A patent/CN101854911B/zh active Active
- 2009-04-22 CN CN201210383098.4A patent/CN102885708B/zh active Active
- 2009-04-22 US US12/996,929 patent/US10966983B2/en active Active
- 2009-04-22 WO PCT/JP2009/058022 patent/WO2009150902A1/ja active Application Filing
- 2009-04-22 EP EP09762333.4A patent/EP2298275B1/en active Active
- 2009-04-22 CA CA2727272A patent/CA2727272A1/en not_active Abandoned
- 2009-04-22 ES ES09762333.4T patent/ES2671040T3/es active Active
- 2009-04-22 KR KR1020177003652A patent/KR101850405B1/ko active IP Right Grant
- 2009-04-22 EP EP18150042.2A patent/EP3335693B1/en active Active
- 2009-04-22 KR KR1020097022487A patent/KR101023503B1/ko active IP Right Grant
- 2009-04-23 TW TW102148294A patent/TWI507212B/zh active
- 2009-04-23 TW TW098113461A patent/TWI424855B/zh active
- 2009-10-01 JP JP2009229984A patent/JP5946234B2/ja active Active
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JP2012188399A (ja) * | 2011-03-11 | 2012-10-04 | Kao Corp | 皮膚保湿剤 |
Also Published As
Publication number | Publication date |
---|---|
TW200950815A (en) | 2009-12-16 |
EP2298275A4 (en) | 2013-12-18 |
KR20170019477A (ko) | 2017-02-21 |
JP5946234B2 (ja) | 2016-07-05 |
KR20110005628A (ko) | 2011-01-18 |
EP2298275A1 (en) | 2011-03-23 |
US10966983B2 (en) | 2021-04-06 |
KR101746743B1 (ko) | 2017-06-13 |
KR101850405B1 (ko) | 2018-04-19 |
TWI507212B (zh) | 2015-11-11 |
EP3335693B1 (en) | 2023-09-13 |
ES2959848T3 (es) | 2024-02-28 |
CN101854911B (zh) | 2012-11-28 |
TW201417837A (zh) | 2014-05-16 |
CN102885708B (zh) | 2015-03-18 |
KR101023503B1 (ko) | 2011-03-21 |
KR20100029741A (ko) | 2010-03-17 |
CA2727272A1 (en) | 2009-12-17 |
JPWO2009150902A1 (ja) | 2011-11-10 |
CN101854911A (zh) | 2010-10-06 |
HK1179514A1 (en) | 2013-10-04 |
EP3335693A1 (en) | 2018-06-20 |
US20110081429A1 (en) | 2011-04-07 |
JP2010077130A (ja) | 2010-04-08 |
TWI424855B (zh) | 2014-02-01 |
ES2671040T3 (es) | 2018-06-04 |
EP2298275B1 (en) | 2018-04-11 |
JP4403467B1 (ja) | 2010-01-27 |
CN102885708A (zh) | 2013-01-23 |
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