US20080064664A1 - Skin Beautifier - Google Patents

Skin Beautifier Download PDF

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Publication number
US20080064664A1
US20080064664A1 US10/594,661 US59466105A US2008064664A1 US 20080064664 A1 US20080064664 A1 US 20080064664A1 US 59466105 A US59466105 A US 59466105A US 2008064664 A1 US2008064664 A1 US 2008064664A1
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US
United States
Prior art keywords
skin
sphingomyelin
effects
food
feed
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/594,661
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English (en)
Inventor
Ken Kato
Noriko Ueda
Susumu Miura
Toshimitsu Yoshioka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Snow Brand Milk Products Co Ltd
Original Assignee
Snow Brand Milk Products Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Snow Brand Milk Products Co Ltd filed Critical Snow Brand Milk Products Co Ltd
Publication of US20080064664A1 publication Critical patent/US20080064664A1/en
Assigned to SNOW BRAND MILK PRODUCTS CO., LTD. reassignment SNOW BRAND MILK PRODUCTS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MIURA, SUSUMU, YOSHIOKA, TOSHIMITSU, KATO, KEN, UEDA, NORIKO
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
    • A61K31/688—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols both hydroxy compounds having nitrogen atoms, e.g. sphingomyelins
    • 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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/92—Oral administration

Definitions

  • the present invention relates to a skin beautifier containing sphingomyelin as an effective ingredient and providing beauty effects, such as skin-moisturizing, skin-beautifying, skin-roughness-preventing, and wrinkle-preventing effects, by oral ingestion thereof, and relates to a skin-beautifying food/drink and a feed containing sphingomyelin.
  • the skin is an interface of an organism with the environment, prevents moisture loss from the body, and has a skin barrier function preventing the invasion of biotoxic substances, such as microorganisms and allergens, from the environment. Intercorneocyte lipids, ceramides in particular, and sebum in the stratum corneum are said to bear these functions. It is said that the stratum corneum must contain 10 to 20% moisture to function normally and maintain a healthy condition. The moisture is retained in the stratum corneum by the skin barrier function and flexibility and elasticity of the skin are thereby maintained.
  • TEWL transepidermal water loss
  • a healthy condition of the skin i.e., a beautified skin condition
  • a healthy condition of the skin can be achieved by increasing the moisture content of the skin or suppressing an increase in TEWL.
  • Ceramides are one of human skin components and have skin-moisturizing and protecting functions and skin-roughness-preventing and improving effects.
  • cosmetics utilizing ceramides skin cosmetic products containing a member of ceramide family, such as ceramides, glucosylceramides, and galactosylceramides, and diisopropylamine dichloroacetate or ⁇ -aminobutyric acid are known (Patent Document 1) .
  • Patent Document 1 there are problems such that ceramides applied to the skin cannot reach nor be absorbed in the skin due to a barrier of epidermal lipids and that cosmetic ingredients other than ceramides cause irritation and inflammation.
  • Patent Document 2 health foods containing ceramides composed of sphingosine, a fatty acid, and a sugar, as an effective ingredient are also known (Patent Document 2).
  • the raw materials for the ceramides composed of sphingosine, a fatty acid, and a sugar, those derived from Amorphophalus konjac and rice are commercially available.
  • these raw materials contain ceramides in a low amount less than 3%. Therefore, in order to achieve the effects by oral ingestion, it is necessary to blend a large amount of the raw materials.
  • the health foods are unsatisfactory. Therefore, materials which can be readily ingested from daily food are desired.
  • Sphingomyelin accounts for about 30% of phospholipids in milk and has a structure in which phosphocholine is bonded to a ceramide skeleton composed of sphingosine and a fatty acid. Sphingomyelin is known to be present in the brain and nerve tissues in large amounts (Non-Patent Document 1). It is also known that sphingomyelin is slightly contained in food such as yolk.
  • Non-Patent Document 2 It is reported that a sphingomyelin is absorbed through the small intestine in blood vessels when orally ingested.
  • Non-Patent Document 3 it is known that a sphingomyelin in the stratum glanulosum of the skin is hydrolyzed by sphingomyelinase into a ceramide to be supplied to the stratum corneum.
  • Patent Document 1 Japanese Patent Laid-Open No. Hei 01-22810
  • Patent Document 2 Japanese Patent Laid-Open No. Hei 11-113530
  • Non-Patent Document 1 Harper's Biochemistry, 24th Ed. 1997, 162.
  • Non-Patent Document 2 Schmelz, et al. J. Nutr. 1994, 124, 702-712.
  • Non-Patent Document 3 Uchida, et al. Seikagaku (The Journal of Japanese Biochemical Society) 2001, 73(4), 269-272.
  • a skin-beautifying food or feed which has beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, by oral ingestion thereof and which includes a safe raw material derived from food.
  • the present inventors have conducted intensive searching for a component which has beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, by oral ingestion thereof, and have found that beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, can be obtained by orally ingesting a sphingomyelin, which is a phospholipid.
  • the skin-beautifying feed in the present invention refers to the feed which exerts having skin-moisturizing and protecting effects in an animal to improve a skin condition thereof.
  • a skin beautifier containing a sphingomyelin as an effective ingredient and a skin-beautifying food or feed containing a sphingomyelin can be provided. Since the effective ingredient of the skin beautifier according to the present invention is derived from food, the skin beautifier is safe and can achieve the beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, by oral ingestion thereof.
  • the present invention is characterized by using a sphingomyelin, a phospholipid, as an effective ingredient.
  • Sphingomyelins which can be used in the present invention are derived from natural substances.
  • sphingomyelins derived from milk such as cow milk and goat milk and egg yolk of hens can be used.
  • an inexpensive sphingomyelin raw material derived from cow milk, which contains sphingomyelins in a high concentration of 25% or more, is available at a market. Such a raw material may be advantageously used.
  • the above-mentioned sphingomyelin may be used as a skin beautifier without modification or may be used as a nutrition composition by blending the sphingomyelin with raw materials, such as sugars, lipids, proteins, vitamins, minerals, and flavorings which are generally used in medicines, food, and feed.
  • the sphingomyelin may be formulated into powder, granules, tablets, capsules, or drink according to a known method.
  • other components having an effect on beauty for example, collagen which accelerates collagen production in the skin, vitamin C, or iron, can be used with the sphingomyelin.
  • the effective dose of the skin beautifier according to the present invention it was confirmed by an animal study using nude mice described below that the moisture content of the skin was increased and the transepidermal water loss (TEWL) through skin was decreased by oral administration of 2 mg or more, preferably 5 mg or more, of sphingomyelin per kg of mouse body weight. Therefore, generally, the beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, can be expected by administration of 2 mg or more, preferably 5 mg or more of sphingomyelin per day for an adult. Therefore, this amount may be necessarily ingested.
  • TEWL transepidermal water loss
  • sphingomyelin may be blended with general food, for example, yogurt, milk-based drink, wafers, or dessert.
  • general food for example, yogurt, milk-based drink, wafers, or dessert.
  • 100 g of the food preferably contains 0.1 to 400 mg of sphingomyelin in order to administer 2 mg or more of sphingomyelin per day for an adult.
  • sphingomyelin may be blended with general feed, for example, livestock feed or pet food.
  • general feed for example, livestock feed or pet food.
  • 100 g of the feed preferably contains 0.1 to 400 mg of sphingomyelin in order to administer 2 mg or more of sphingomyelin per day.
  • the method for blending the sphingomyelin is not specifically limited.
  • sphingomyelin when sphingomyelin is added to or blended in a solution, sphingomyelin may be used after prepared into a form of a medicine, food, or feed by suspending or dissolving a sphingomyelin raw material in deionized water and stirring and mixing the resulting mixture.
  • the stirring and mixing may be conducted under any conditions as long as sphingomyelin can be uniformly mixed, and may be conducted with an ultradisperser or a TK homomixer.
  • This sphingomyelin solution may be concentrated by using an RO membrane or may be dried by lyophilization, if necessary, in order to be readily used for a medicine, food, or feed.
  • sterilization procedures which are generally conducted in the manufacturing of a medicine, food, or feed can be employed. If a product is in a form of powder, dry-heat sterilization can be also employed. Therefore, according to the present invention, a medicine, food, and feed containing the sphingomyelin can be manufactured in various forms such as a solution, gel, powder, or granules.
  • a sphingomyelin raw material (Phospholac 500; manufactured by NZMP) containing 10% of sphingomyelins was dissolved in deionized water as shown in Table 1. The solution was heated to 50° C. and then mixed under stirring with an ultradisperser (ULTRA-TURRAXT-25; manufactured by IKA Japan) at 9500 rpm for 20 minutes to prepare Test Feeds 1 to 3.
  • mice Five-week old CD-1 (ICR)-nu/nu mice were divided into the following 4 test groups (10 mice in each group), namely, (Group A) a group receiving 10 g of physiological saline per kg of mouse body weight, (Group B) a group receiving 10 g of the Test Feed 1 per kg of mouse body weight, (Group C) a group receiving 10 g of the Test Feed 2 per kg of mouse body weight, and (Group D) a group receiving 10 g of the Test Feed 3 per kg of mouse body weight. Mice in all the groups were fed by orally administering the feed once daily by gavage feeding for 4 weeks. Moisture contents and transepidermal water losses in the tail skin of each mouse were measured at the start and the end of the feeding.
  • a reaction solution prepared by adding protease to an aqueous solution containing 10% of whey protein concentrate (WPC) was extracted with a solution of chloroform-methanol (2:1).
  • the extract was concentrated and then was further extracted with acetone to obtain a complex lipid fraction.
  • this complex lipid fraction was subjected to a florisil-column chromatography and eluted successively with chloroform-methanol solutions to obtain a fraction containing phospholipid.
  • This phospholipid fraction was subjected to a silica-gel chromatography and eluted successively with chloroform-methanol solutions to obtain a fraction phospholipid.
  • This fraction was lyophilized to obtain a sphingomyelin raw material.
  • This sphingomyelin raw material was developed on a thin-layer chromatography, followed by color development with the Dittmer reagent. The sphingomyelin content was measured by densitometry to be 95.2%.
  • This spingomyelin raw material can be used as a skin beautifier according to the present invention without modification.
  • Raw materials were mixed at the blending quantities shown in Table 3, and then were made into tablets each weighing 1 g by a known method to manufacture the skin beautifier according to the present invention.
  • sphingomyelin raw material ⁇ -Lipid; manufactured by NZMP
  • TK homomixer manufactured by Tokushu Kika Kogyo
  • This sphingomyelin solution (4.0 kg) was blended with 5.0 kg of casein, 5.0 kg of soy protein, 1.0 kg of fish oil, 3.0 kg of perilla oil, 18.0 kg of dextrin, 6.0 kg of mineral mixture, 1.95 kg of vitamin mixture, 2.0 kg of an emulsifier, 4.0 kg of a stabilizer, and 0.05 kg of flavoring, and the mixture was packed in 200-ml retort pouches. Then, sterilization by a retort sterilizer (First-class pressure vessel, TYPE: RCS-4CRTGN; manufactured by HISAKA WORKS) at 121° C. for 20 minutes was performed to manufacture 50 kg of a skin-beautifying liquid nutrition composition according to the present invention. In 100 g of this skin-beautifying liquid nutrition composition, 20 mg of sphingomyelin was contained.
  • TYPE First-class pressure vessel, TYPE: RCS-4CRTGN; manufactured by HISAKA WORKS
  • sphingomyelin raw material Phospholac 500; manufactured by NZMP
  • sphingomyelin raw material Phospholac 500; manufactured by NZMP
  • the solution was heated to 50° C. and then mixed under stirring with an ultradisperser (ULTRA-TURRAXT-25; manufactured by IKA Japan) at 9500 rpm for 30 minutes.
  • an ultradisperser ULTRA-TURRAXT-25; manufactured by IKA Japan
  • 40 g of sorbitol, 2 g of an acidifier, 2 g of flavoring, 5 g of pectin, 5 g of whey protein concentrate, 1 g of calcium lactate, and 235 g of deionized water were added.
  • the mixture was stirred and mixed and then was packed in 200-ml pouches with a screw cap. After the sterilization at 85° C. for 20 minutes, the packs were hermetically sealed to prepare 5 bags (each 200 g) of skin-beautifying gel-type food according to the present invention. No precipitate was observed and no abnormal flavor was detected in all thus obtained skin-beautifying gel-type food. In 100 g of this skin-beautifying gel-type food, 100 mg of sphingomyelin was contained.
  • the bottles were hermetically sealed to prepare 10 bottles (each 100 ml) of skin-beautifying drink according to the present invention. No precipitate was observed and no abnormal flavor was detected in all thus obtained skin-beautifying drink. In 100 g of this skin-beautifying drink, 250 mg of sphingomyelin was contained.
  • SM-4 sphingomyelin raw material
  • TK homomixer MLK II 160 type; manufactured by Kokusyu Kika Kogyo
  • This sphingomyelin solution (10 kg) was blended with 12 kg of soybean cake, 14 kg of skimmed milk powder, 4 kg of soybean oil, 2 kg of corn oil, 23.2 kg of palm oil, 14 kg of corn starch, 9 kg of flour, 2 kg of bran, 5 kg of a vitamin mixture, 2.8 kg of cellulose, and 2 kg of a mineral mixture.
  • the mixture was sterilized at 120° C. for 4 minutes to prepare 100 kg of skin-beautifying dog food according to the present invention. In 100 g of this skin-beautifying dog food, 8 mg of sphingomyelin was contained.
  • the skin beautifier according to the present invention is safe because the effective ingredient is derived from food, and provides beauty effects, such as skin-moisturizing and protecting effects, skin-roughness-preventing and improving effects, and a wrinkle-preventing effect, by oral ingestion thereof.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Birds (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Biophysics (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Fodder In General (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Non-Alcoholic Beverages (AREA)
US10/594,661 2004-03-30 2005-03-30 Skin Beautifier Abandoned US20080064664A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2004-101142 2004-03-30
JP2004101142A JP2005281257A (ja) 2004-03-30 2004-03-30 美肌剤
PCT/JP2005/006030 WO2005094839A1 (ja) 2004-03-30 2005-03-30 美肌剤

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/006030 A-371-Of-International WO2005094839A1 (ja) 2004-03-30 2005-03-30 美肌剤

Related Child Applications (1)

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US12/947,891 Division US8920822B2 (en) 2004-03-30 2010-11-17 Skin beautifier

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US20080064664A1 true US20080064664A1 (en) 2008-03-13

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US10/594,661 Abandoned US20080064664A1 (en) 2004-03-30 2005-03-30 Skin Beautifier
US12/947,891 Expired - Fee Related US8920822B2 (en) 2004-03-30 2010-11-17 Skin beautifier

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US12/947,891 Expired - Fee Related US8920822B2 (en) 2004-03-30 2010-11-17 Skin beautifier

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US (2) US20080064664A1 (pt)
EP (1) EP1736159B1 (pt)
JP (1) JP2005281257A (pt)
KR (1) KR101094693B1 (pt)
CN (1) CN1997376B (pt)
AU (1) AU2005228742B2 (pt)
CA (1) CA2561729C (pt)
DK (1) DK1736159T3 (pt)
ES (1) ES2402299T3 (pt)
HK (1) HK1105361A1 (pt)
NZ (1) NZ550269A (pt)
PT (1) PT1736159E (pt)
WO (1) WO2005094839A1 (pt)

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JP5208428B2 (ja) * 2007-01-30 2013-06-12 雪印メグミルク株式会社 美肌剤
JP5679966B2 (ja) * 2009-05-20 2015-03-04 よつ葉乳業株式会社 皮膚機能改善組成物
JP5922863B2 (ja) * 2010-02-03 2016-05-24 花王株式会社 運動機能改善剤
JP5922862B2 (ja) * 2010-02-03 2016-05-24 花王株式会社 ミトコンドリア機能向上剤
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JP6225199B2 (ja) * 2016-02-01 2017-11-01 花王株式会社 運動機能改善剤
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HK1105361A1 (en) 2008-02-15
KR101094693B1 (ko) 2011-12-20
EP1736159A4 (en) 2009-07-29
EP1736159A1 (en) 2006-12-27
AU2005228742B2 (en) 2011-07-28
KR20070002062A (ko) 2007-01-04
PT1736159E (pt) 2013-04-03
CN1997376A (zh) 2007-07-11
CN1997376B (zh) 2011-05-11
EP1736159B1 (en) 2013-01-09
WO2005094839A1 (ja) 2005-10-13
CA2561729C (en) 2013-10-15
US20110065670A1 (en) 2011-03-17
DK1736159T3 (da) 2013-02-11
ES2402299T3 (es) 2013-04-30
AU2005228742A1 (en) 2005-10-13
CA2561729A1 (en) 2005-10-13
US8920822B2 (en) 2014-12-30

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