WO2005099682A1 - Préparations à usage externe - Google Patents

Préparations à usage externe Download PDF

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Publication number
WO2005099682A1
WO2005099682A1 PCT/JP2004/013315 JP2004013315W WO2005099682A1 WO 2005099682 A1 WO2005099682 A1 WO 2005099682A1 JP 2004013315 W JP2004013315 W JP 2004013315W WO 2005099682 A1 WO2005099682 A1 WO 2005099682A1
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WO
WIPO (PCT)
Prior art keywords
external
skin
blood circulation
lipolysis
vanillyl nonanoate
Prior art date
Application number
PCT/JP2004/013315
Other languages
English (en)
Japanese (ja)
Inventor
Ayako Inoki
Katsuyuki Fujimura
Original Assignee
Kobayashi Pharmaceutical 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
Priority claimed from JP2004099024A external-priority patent/JP3702393B2/ja
Application filed by Kobayashi Pharmaceutical Co., Ltd. filed Critical Kobayashi Pharmaceutical Co., Ltd.
Publication of WO2005099682A1 publication Critical patent/WO2005099682A1/fr

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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
    • A61K8/33—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
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • 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
    • A61Q19/005—Preparations for sensitive skin
    • 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
    • A61Q19/06—Preparations for care of the skin for countering cellulitis
    • 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
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to an external blood circulation promoter and an external lipolysis promoter. More specifically
  • the present invention also relates to an external blood circulation promoter and an external lipolysis promoter which cause less skin irritation. Furthermore, it relates to a composition for external use.
  • Patent Document 1 JP-A-57-9729
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2001-213717
  • Patent Document 3 JP 2001-316317 A
  • Patent Document 4 JP 2001-322931 A
  • Patent Document 5 JP-A-2002-114676
  • Patent Document 6 JP 2001-26538 A
  • Patent Document 7 JP-A-11-246478
  • vanillyl nonanoate a capsaicinoid-like compound
  • the vanillyl nonanoate has excellent blood circulation promoting effect and excellent lipolysis promoting effect in external use. It was found to be effective and less irritating to the skin.
  • the vanillyl nonanoate has been conventionally used as a food or oral drug based on its immunostimulatory activity, energy metabolic activity, obesity inhibitory effect, body fat accumulation inhibitory effect, adrenaline secretion promoting effect, blood dulose increasing effect, etc.
  • Patent Documents 5-7 the use for oral ingestion has been proposed (see, for example, Patent Documents 5-7), it has been confirmed that there is no known low irritation to the skin and no use as an external preparation. Was completed.
  • Item 1 An external blood circulation promoter containing vanillyl nonanoate as an active ingredient.
  • Item 2 An external lipolysis promoter containing vanillyl nonanoate as an active ingredient.
  • Item 3 An external composition containing the external blood circulation promoter according to Item 1.
  • Item 4 An external composition containing the external lipolysis accelerator according to Item 2.
  • Item 5 The external composition according to Item 3 or 4, which is a skin cosmetic, a scalp cosmetic, a bath preparation, an external preparation for medicine, or an eye drop.
  • the external blood circulation promoter of the present invention has the following formula: [0008] [Formula 1]
  • the vanillyl nonanoate is a known compound, and can be prepared according to a conventional method.
  • the vanillyl nonanoate thus obtained exerts a favorable blood circulation promoting effect when applied transdermally or transmucosally to the skin or mucous membranes, and furthermore, its irritation to the skin and the like is suppressed, If it does not feel irritating or is reduced, it has properties suitable as an external blood circulation promoter.
  • Such vanillyl nonanoate can be effectively used as an active ingredient of an external blood circulation promoter.
  • the topical blood flow promoter of the present invention does not prevent the inclusion of other components as long as the effect of the present invention is not impaired, as long as it contains vanillyl nonanoate as an active ingredient.
  • Examples of other powerful components include various plant extracts that have no skin irritation and have a blood circulation promoting effect, similar to the active ingredient of the present invention (Japanese Patent Application Laid-Open No. 9-268118). And JP-A-10-226621).
  • Specific examples of the plant extract include citron, linden, bodaige, Ichiyou, horse chestnut, butcher bloom and the like.
  • additives and diluents include alcohols such as polyhydric alcohols, oily components, inorganic powders, surfactants, pH adjusters, preservatives, fragrances, and pigments.
  • the proportion of vanillyl nonanoate contained in the topical blood circulation enhancer of the present invention depends on the effect of the present invention. There is no particular limitation as long as it plays, but for example, 0.1% by weight or more, preferably 1% by weight or more can be exemplified. In addition, since the topical blood circulation promoter of the present invention may be as strong as vanillyl nonanoate, the upper limit of the proportion of vanillyl nonanoate is 100% by weight.
  • the above vanillyl nonanoate also exerts a good lipolysis promoting effect when applied transdermally or transmucosally to the skin or mucous membranes, and furthermore, the irritation to the skin etc. is suppressed, and the skin feels irritation. It has a characteristic that is suitable as a weak or weak external lipolysis accelerator.
  • the lipolysis promoter of the present invention only needs to contain vanillyl nonanoate as an active ingredient, and may contain other components as long as the effects of the present invention are not impaired.
  • those having or enhancing lipolysis may be used as in vanillyl nonanoate.
  • examples of such components include xanthine derivatives, j8 adrenergic action enhancers, ⁇ - adrenergic action inhibitors and the like.
  • additives and diluents include xanthine derivatives, j8 adrenergic action enhancers, ⁇ - adrenergic action inhibitors and the like.
  • the ratio of vanillyl nonanoate contained in the lipolysis accelerator is not particularly limited as long as it exhibits a lipolysis promoting effect.
  • 0.1% by weight or more preferably 1% by weight or more can be exemplified.
  • topical lipolysis promoter of the present invention may be a shall such only from vanillyl nonanoic acid, thus the upper limit of the proportion of nonanoic acid vanillyl is 100 weight 0/0.
  • the above-mentioned vanillyl nonanoate can also be used as a component of an external composition for the purpose or action of promoting blood circulation.
  • the composition for external use here include various diseases such as, for example, moisturizing, chilling, numbness of the limbs, swelling, Reino disease, shoulder and neck stiffness, hair loss (hair), and the like due to peripheral blood circulation disorders.
  • Topical skin preparation for the improvement of obstructive diseases or conditions An external pharmaceutical composition such as an external preparation for the skin that promotes skin absorption and medicinal properties; an eye drop that has the effect of suppressing or improving redness and fatigue of eyes, or percutaneous absorption of active ingredients by promoting blood circulation in the eyes Eye drops that have the effect of promoting sex and drug efficacy; scalp cosmetics that have the effect of promoting blood circulation in the scalp, or scalp cosmetics that have the effect of promoting the blood circulation of the scalp to promote the absorption of active ingredients into the scalp; Examples thereof include skin cosmetics having an action of promoting warmth or metabolism, and skin dandruff cosmetics having an action of promoting blood circulation and promoting percutaneous absorption of an active ingredient.
  • the present invention provides an external composition containing vanillyl nonanoate.
  • composition for external use of the present invention may be prepared by separately mixing vanillyl nonanoate as an active ingredient separately, or the above-mentioned blood circulation promoting agent of the present invention containing vanillyl nonanoate as an active ingredient of the composition for external use It can also be prepared by blending as
  • compositions for external use include the above-mentioned skin cosmetics, scalp cosmetics, bath additives (bath preparations), external medicines, eye drops and the like.
  • topical drug include various ointments, creams, gels, lotions, aerosols, and the like, which may contain other active ingredients in addition to vanillyl nonanoate, as long as the objects and effects of the present invention are not hindered. Packing agents and the like can be mentioned.
  • an ointment it may be based on an oily base or an oil-in-water or water-in-oil emulsifying base, but it is suitable as an oily base even if it is misaligned.
  • examples include vegetable oils, animal oils, synthetic oils, fatty acids, esters, higher alcohols and natural or synthetic glycerides. These can be prepared according to conventional methods depending on the form of the preparation, and can be used according to conventional methods.
  • the medicinal ingredient is not particularly limited, for example, an analgesic anti-inflammatory agent, an antipruritic agent, a bactericidal antiseptic, an astringent, an emollient, a hormonal agent, a warming agent, a cooling agent, a humectant. Etc. can be used as needed.
  • Dermatological cosmetics or scalp cosmetics may be in various forms, for example, water-in-oil type or oil-in-water type emulsifying type (cream, emulsion), paste, diel, aerosol, solid, etc. Alternatively, it can be an aqueous cosmetic.
  • dermatological cosmetics include creams, emulsions, lotions, serums, lipsticks, foundations, lotions, massage agents, and skin cleansers ( Liquid stones and solid stones).
  • scalp cosmetics There are no particular restrictions on scalp cosmetics as long as they are applied to the scalp.For example, hair tonics, hair styling agents, hair styling agents, shampoos, hair treatments, hair conditioners, hair rinses, hair massaging agents, hair restoration agents And a hair restorer.
  • the bathing agent is not particularly limited as long as it can be applied by adding it to water or hot water.
  • a powdered or fine-grained bathing agent can be used, and a liquid (aqueous solution, oil) can be used.
  • a liquid aqueous solution, oil
  • Water-in-water or oil-in-water emulsification type bathing agents can also be used.
  • the eye drops may be in the form of a solution, or may be in the form of a paste such as a cream or a gel like an eye ointment.
  • these skin cosmetics, scalp cosmetics and eye drops can be prepared according to a conventional method according to the product form, and can be used according to a conventional method.
  • the content of the external blood circulation promoter in the external composition of the present invention is not particularly limited as long as the effects of the present invention are exerted.
  • the lower limit is usually 0.1% by weight, preferably 1% by weight, more preferably 10% by weight.
  • the upper limit is not particularly limited, and can be appropriately selected depending on the type and purpose of the composition for external use and the shape.
  • the ratio is usually 80% by weight or less, preferably 50% by weight or less.
  • the carrier blended in the external composition of the present invention is desirably a hydrophobic (non-polar) base or solvent from the viewpoint of compatibility with vanillyl nonanoate and stability.
  • bases or solvents include petrolatum (yellow petrolatum, white petrolatum), paraffin, liquid paraffin, plasma liquid paraffin, beeswax, salami beeswax, spermaceti, lard, beef tallow, lanolin (hydrolanolin, (Refined lanolin), olive oil, sesame oil, soybean oil, camellia oil, corn oil, rapeseed oil, laccase oil, castor oil, squalane, lauric acid, myristic acid, normitic acid, stearic acid, oleic acid, pendecilenic acid, isostearic acid , Lauryl anolecone, cetanol, stearyl alcohol, oleyl alcohol, lanolin alcohol, hexyldecan
  • Vanillyl nonanoate can also be used as a component of an external composition for the purpose or action of promoting lipolysis.
  • the topical composition as used herein includes an external pharmaceutical composition for promoting metabolism, ameliorating obesity, preventing or ameliorating hyperlipidemia, making the whole or part of the body thin, removing cellulite, and skin cosmetics. , Bath additives and the like can be exemplified.
  • Skin cosmetics include various forms, for example, oily or aqueous cosmetics such as water-in-oil or oil-in-water emulsified (tarime, emulsion), paste, diel, aerosol, and solid. Fees. More specifically, mention may be made of creams, emulsions, lotions, serums, lipsticks, foundations, lotions, massage agents, skin cleansers (liquid stones, solid stones) and the like.
  • the bathing agent is not particularly limited as long as it can be applied by adding it to water or hot water.For example, a powdered or fine-grained bathing agent can be used, and a liquid (aqueous solution, oil) can be used. Water-in-water or oil-in-water emulsification type bathing agents can also be used.
  • fat application can be promoted by applying, spraying, sticking, or the like on the thin, part or whole body of the external composition.
  • a higher lipolysis-promoting effect is obtained by rubbing into the skin, and when spraying, by rubbing the externally applied composition onto the skin after spraying.
  • when used as a skin cleanser it can promote the breakdown of fat while washing the body.
  • when used as a bath additive it can be thinned by using hot water. By applying massage while applying hot water, a higher lipolysis promoting effect can be obtained.
  • the content of vanillyl nonanoate in the external composition of the present invention is not particularly limited as long as the effects of the present invention are exhibited.
  • the lower limit is usually 0.1% by weight, preferably 1% by weight, more preferably 10% by weight.
  • the upper limit is not particularly limited, and can be appropriately selected depending on the type and purpose of the composition for external use and the shape.
  • the ratio is usually 80% by weight or less, preferably 50% by weight or less.
  • the same carrier as that described in the above (3) can be used as the carrier to be blended in the composition for external use of the present invention.
  • the topical blood circulation promoter of the present invention containing vanillyl nonanoate as an active ingredient, and the topical composition of the present invention containing valilyl nonanoate in a form in which the blood circulation promoting action is exerted are applied to the skin or eyes. It exerts a good blood circulation promoting effect when applied.
  • the external use lipolysis promoter of the present invention containing valilyl nonanoate as an active ingredient and the external use composition of the present invention containing vanillyl nonanoate in a form in which the lipolysis accelerating action is exerted are applied to the skin. In this case, a good lipolysis promoting effect is exhibited. Furthermore, it has excellent characteristics such as being less irritating to the skin and the like.
  • Vanillyl nonanoate was produced by the following method according to the description in the literature Journal of Medicinal Chemistry 1993, Vol. 36, No. 16 p.2337.
  • Test Example 1 The following test (Test Example 1) was performed using vanillyl nonanoate (99% or more) prepared above.
  • the effect of promoting blood circulation when vanillyl nonanoate was applied to the skin was evaluated using rats as described below.
  • the test sample used was vanillyl nonanoate (Example 1) prepared in Reference Example 1 as an example, and 0.1% by weight of noryl acid ⁇ -lylamide (manufactured by Toyo Pharma Co., Ltd. ⁇ 99% or more) as a comparative example.
  • a solution (Comparative Example 1) and an ethanol-Z water mixed solution (a mixture of equal amounts of l: 1 (w / w)) (Control 1) were used as a control.
  • ⁇ -rilamide noryl is a compound known to have a blood circulation promoting effect on the skin, and was used as a positive control.
  • the Nio, Te Roh - Rusanwa - 0.1 0/0 solution of Riruamido the equal amount mixture of ethanol Z water: a solution prepared in (l l (w / w) ).
  • Rats Male, 9 weeks old had their back hairs removed in advance using an electric shaver and a depilatory cream on the day before the test.
  • the rats were anesthetized with ether, and a laser Doppler blood flow meter was attached to the back, and the steady-state blood flow before application of the test sample was measured.
  • the blood flow probe was removed and the test sample was applied to the back at a rate of 10 L / cm 2 (each test sample was performed on 5 animals).
  • a blood flow probe was attached again to the application area on the back, and the blood flow was continuously measured. The average blood flow was determined from the blood flow 15-20 minutes after application, and the relative value (%) to the previously measured steady-state blood flow (100%) was determined.
  • Table 1 [Table 1]
  • the effect of promoting lipolysis when vanillyl nonanoate was applied to the skin was evaluated using rats as described below.
  • the test sample used was vanillyl nonanoate (Example 1) prepared in Reference Example 1 as an example, and a 2% by weight solution of aminophylline (ICN Cat. No. 190144) (Comparative Example 2) was used as a comparative example.
  • a mixed solution of ethanol and Z water a mixed solution of an equal volume of 1: 1 (W / W)
  • control 1 was used as a positive control.
  • aminophylline is a compound known to have a lipolytic effect when applied to the skin, and was used as a positive control.
  • the 2% by weight solution of aminophylline is a solution prepared with an equal mixture of ethanol / water (1: 1 (W / W)).
  • Rats Male, 11 weeks old had their abdominal hair removed on the day before the test using an electric shaver and a depilatory cream.
  • 250 l of the test sample was applied to the abdomen of the above-mentioned rats as widely as possible.
  • laparotomy was performed under ether anesthesia, and blood was collected from the abdominal vena cava (5 rats were tested for each test sample).
  • the serum was separated from the collected blood, and the amount of free fatty acids in the serum was measured by NEFA C-Test II Co. (Wako Pure Chemical Industries).
  • the relative value (%) to an ethanol / water mixed solution (1: 1 (W / W) equivalent mixed solution) (control) was determined. The results are shown in Table 2.
  • vanillyl nonanoate (Example 1) prepared in Reference Example 1 was used as an example, and 0.1% by weight of noryl acid ⁇ -lylamide (manufactured by Toyo Pharma Co., Ltd., 99% or more) was used as a comparative example.
  • a solution (Comparative Example 1) and an ethanol-Z water mixed solution (mixture of equal amounts of l: l (w / w)) (Control 1) were used as a control.
  • the rats Male, 10 weeks old had their axillary hairs removed in advance using an electric shaver and a depilatory cream on the day before the test.
  • 201 of each of the above test samples was applied to one of the axilla, and no treatment was applied to the other axilla.
  • the number of times of application to the axillary side and the untreated axillary side were measured, and the number of times of application side swinging was subtracted to obtain the numerical value obtained by subtracting the number of untreated side swinging times.
  • the results are shown in Table 3.
  • vanillyl nonanoate prepared in Reference Example 1 was purified from poly (nonyl acid) Luamide (manufactured by Toyo Pharmaceutical Co., Ltd.99% or more)
  • the blood circulation-promoting effect is almost the same as 0.1%, but the skin irritation is reduced to about 1/3, and the skin irritation is extremely low. That's half lj.
  • an ointment-like pharmaceutical composition for external use on the skin was prepared.
  • This ointment when applied to the skin, can be used as both a blood circulation promoter and a lipolysis promoter.
  • this skin care pill When applied to the skin, this skin care pill can be used as both a blood circulation promoter and a lipolysis promoter.
  • a liquid anti-inflammatory analgesic (skin external composition: liquid) was prepared according to the following formulation. This solution can be used as a more effective anti-inflammatory analgesic by applying it to the skin, or as an anti-inflammatory analgesic having a lipolysis promoting action.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Obesity (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

[PROBLÈMES] Fournir un accélérateur de circulation sanguine à usage externe qui ne provoque qu'une irritation réduite de la peau, ou un accélérateur de lipolyse à usage externe qui ne provoque qu'une irritation réduite de la peau et une préparation dermique à usage externe qui ne provoque qu'une irritation réduite de la peau et présente la fonction consistant à accélérer la circulation sanguine ou la lipolyse. [MOYENS POUR RÉSOUDRE LES PROBLÈMES] L'accélérateur de circulation sanguine à usage externe ou l'accélérateur de lipolyse à usage externe contient un nonanoate de vanillyle en tant qu'ingrédient actif. La composition à usage externe contient le nonanoate de vanillyle sous une forme telle qu'il produit l'effet d'accélérer la circulation sanguine ou la lipolyse.
PCT/JP2004/013315 2004-03-30 2004-09-13 Préparations à usage externe WO2005099682A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004099024A JP3702393B2 (ja) 2003-03-31 2004-03-30 外用剤
JP2004-099024 2004-03-30

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007145793A (ja) * 2005-02-01 2007-06-14 Ajinomoto Co Inc 血行促進外用剤及びこれを含有してなる皮膚毛髪用化粧料及び入浴剤
JP2008069121A (ja) * 2006-09-15 2008-03-27 Lion Corp 脂肪減少促進剤
US7981460B2 (en) 2006-06-29 2011-07-19 Ajinomoto Co., Inc. Substituted benzyl ester derivative and use thereof
US8212068B2 (en) 2006-03-24 2012-07-03 Ajinomoto Co., Inc. Ester derivative and use thereof

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JPS579729A (en) * 1980-06-18 1982-01-19 Takasago Corp Vanillyl alcohol derivative
JPH09268118A (ja) * 1996-04-01 1997-10-14 Kao Corp 肌色改善美容剤
JPH10226621A (ja) * 1996-12-12 1998-08-25 Kao Corp 化粧料
JPH11246478A (ja) * 1998-03-04 1999-09-14 Morinaga & Co Ltd エステル結合を有する新規なカプサイシノイド様物質
JP2000312598A (ja) * 1999-04-30 2000-11-14 Morinaga & Co Ltd 新規なカプサイシノイド様物質の合成法
JP2001026538A (ja) * 1999-07-13 2001-01-30 Morinaga & Co Ltd 新規なカプサイシノイド様物質を含有する食品及び医薬組成物
JP2001231717A (ja) * 2000-02-24 2001-08-28 Matsushita Electric Ind Co Ltd 体重計付便座
JP2001316317A (ja) * 2000-05-01 2001-11-13 Kao Corp 血行促進剤
JP2001322931A (ja) * 2000-05-15 2001-11-20 Kao Corp 血行促進剤
JP2002114676A (ja) * 2000-10-06 2002-04-16 Morinaga & Co Ltd 新規なカプサイシノイド様物質を含有する持久力向上用組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS579729A (en) * 1980-06-18 1982-01-19 Takasago Corp Vanillyl alcohol derivative
JPH09268118A (ja) * 1996-04-01 1997-10-14 Kao Corp 肌色改善美容剤
JPH10226621A (ja) * 1996-12-12 1998-08-25 Kao Corp 化粧料
JPH11246478A (ja) * 1998-03-04 1999-09-14 Morinaga & Co Ltd エステル結合を有する新規なカプサイシノイド様物質
JP2000312598A (ja) * 1999-04-30 2000-11-14 Morinaga & Co Ltd 新規なカプサイシノイド様物質の合成法
JP2001026538A (ja) * 1999-07-13 2001-01-30 Morinaga & Co Ltd 新規なカプサイシノイド様物質を含有する食品及び医薬組成物
JP2001231717A (ja) * 2000-02-24 2001-08-28 Matsushita Electric Ind Co Ltd 体重計付便座
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