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WO2006057375A1 - Preparation medicinale pour usage externe - Google Patents

Preparation medicinale pour usage externe Download PDF

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Publication number
WO2006057375A1
WO2006057375A1 PCT/JP2005/021754 JP2005021754W WO2006057375A1 WO 2006057375 A1 WO2006057375 A1 WO 2006057375A1 JP 2005021754 W JP2005021754 W JP 2005021754W WO 2006057375 A1 WO2006057375 A1 WO 2006057375A1
Authority
WO
WIPO (PCT)
Prior art keywords
diol
propane
methyl
external preparation
menthyloxy
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.)
Ceased
Application number
PCT/JP2005/021754
Other languages
English (en)
Japanese (ja)
Inventor
Ikuhiro Kakubari
Ken-Ichi Noguchi
Miyuki Ikeda
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.)
Saitama Daiichi Pharmaceutical Co Ltd
Original Assignee
Saitama Daiichi 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
Application filed by Saitama Daiichi Pharmaceutical Co Ltd filed Critical Saitama Daiichi Pharmaceutical Co Ltd
Publication of WO2006057375A1 publication Critical patent/WO2006057375A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208—Tissues; Wipes; Patches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Definitions

  • the present invention relates to an external preparation containing a medicinal component and a refreshing glaze that does not substantially affect the transdermal absorption rate of the medicinal component.
  • menthols such as 1 menthol and hat power oil have been generally used as a refreshing agent to be blended in external preparations.
  • Menthols and chimney oils are highly sublimable and have a odor and odor, so they emit a strong odor especially when formulated in patches such as poultices and tapes. Therefore, topical preparations in the form of patches containing menthols and power oils can cause problems such as stinking around and causing odors to stick to clothes and hair. have. Because of this problem, the patient himself / herself restricted the use of the patch, or peeled off the patch even though the treatment was not completed. Often there were serious situations.
  • the heartbeat odor possessed by menthols such as 1 menthol has the effect of reducing appetite and suppressing gastric juice secretion.
  • topical preparations such as a skin lotion
  • the user had a loss of appetite due to a pungent odor, sometimes causing nausea and vomiting.
  • menthols such as 1-menthol are solid at room temperature
  • crystals may form over time, or a cooling agent may be present uniformly in the preparation.
  • Oil and coconut oil contain about 50% menthol, and the same problem as above occurs when using Hatsu power oil as a cooling agent.
  • oil and coconut oil are natural products, there is another problem that the stability of the product standard is often lacking because the components are often non-uniform.
  • menthols such as heart force oil and 1 menthol have the effect of promoting the percutaneous absorption of drugs, as well as force 3-1 (menthoxypropane 1,2 diol). It has the effect of promoting percutaneous absorption of medicinal ingredients, and the cumulative permeation amount of medicinal ingredients in percutaneous absorption shows a significant increase depending on the concentration of the above substances. Therefore, in order to control the cumulative permeation amount of medicinal ingredients over a long period of time, the amount of 3-1- (menthoxypropane 1,2 diol) must be limited, which reduces the refreshing feeling, etc. There was a problem. For these reasons, there has been a strong demand to provide a preparation for external use that contains a strawberry refreshing agent that has reduced volatility and strong odor, and that does not substantially affect the transdermal absorption rate of medicinal ingredients. It was.
  • An object of the present invention is to provide an external preparation that solves the above-mentioned problems. More specifically, an irritating odor such as a heartbeat odor is suppressed, and a medicinal component is percutaneously absorbed.
  • the object is to provide an external preparation containing a refreshing agent that does not substantially affect the speed.
  • Means for solving the problem [0007] The present inventors diligently searched for a refreshing agent that has a suppressed strong odor and does not substantially affect the transdermal absorption rate of a medicinal component contained in an external preparation. It has been found that a group of refreshing agents represented by methyl 3- (1-menthyloxy) propane 1,2 diol or derivatives thereof has the desirable properties described above. Conventionally, the above
  • an external preparation in which (1) the medicinal component and (2) the heartbeat odor are suppressed, and the percutaneous absorption rate of the medicinal component is substantially affected.
  • An external preparation containing a refreshing agent that is not given is provided.
  • the refreshing agent is 2-methyl-3- (1 menthoxy) propane mono: L, 2-diol or a derivative thereof described above; the refreshing agent is 2-methyl- 3— (1 Menthyloxy) propane 1,2 diol as described above External preparation, wherein the amount of the refreshing agent is 0.001 to 20% by weight based on the total composition of the external preparation Formulation; the medicinal component is a non-steroidal anti-inflammatory agent, skeletal muscle relaxant, and vasodilator power
  • the refreshing agent contained in the external preparation of the present invention is excellent in that it does not substantially affect the percutaneous absorption rate of the medicinal component of the external preparation in addition to the suppression of the heartbeat odor. It has a nature. Therefore, in the preparation for external use of the present invention, the blending ratio of the above-mentioned refreshing agent with respect to the medicinal component can be greatly increased as compared with the conventional preparation for external use. In addition, it can be used as an external preparation excellent in refreshing feeling. In addition, since the percutaneous absorption rate of medicinal ingredients is not affected, formulation design is facilitated. Moreover, the preparation for external use of the present invention containing a large amount of the above-mentioned refreshing agent does not cause discomfort to the patient who has almost no irritating odor such as odor or cough odor.
  • the preparation for external use of the present invention comprises (1) a medicinal component, and (2) a refreshing agent that suppresses the heartbeat odor and does not substantially affect the transdermal absorption rate of the medicinal component. It is characterized by including.
  • the kind of the medicinal component in the external preparation of the present invention is not particularly limited.
  • Non-steroidal anti-inflammatory drugs such as piroxicam, meloxicam, diclofenac and its salts, loxoprofen and its salts, suprofen, zaltoprofen, thiaprofen, tenidap and their derivatives, antiallergic agents such as trast, ketotifen, azelastine and ibudilast , Skeletal muscle relaxants such as eperisone hydrochloride, tolperisone, tizarin and pridinol, antihistamines such as diphenhydramine and chlorfelamin, nitroglycerin, glass Vasodilators such as isosorbide, salt-carp mouthpiece, minoxidil, local anesthetics such as lidocaine, pro-in hydrochloride, benzocaine, antifungal agents such as miconazole, clotrimazole, butenafine hydrochloride, bifonazole, hydrochloric acid Examples include dysuria such as
  • a refreshing agent that suppresses the heartbeat odor and does not substantially affect the percutaneous absorption rate of medicinal ingredients for example, 2-methyl 3- (1-menthyloxy) propane-1
  • the ability to preferably use 2-diol or a derivative thereof is not limited to these specific substances.
  • V or any other refreshing agent may be used as long as it has a property that suppresses the heart odor and does not substantially affect the transdermal absorption rate of the medicinal component.
  • 2-Methyl-3- (1 menthyloxy) propane 1,2 diol derivative and Examples thereof include ester derivatives, alkyl derivatives, halogen derivatives, and the like. Particularly preferred is 2-methyl-3- (1-menthyloxy) propane 1,2-diol.
  • the refreshing effect of the refreshing agent used in the external preparation of the present invention is not particularly limited.
  • 1S For example, menthols, heart power oil, 3-1- (menthoxypropane-1,2 diol), or 2- It is desirable that the cooling effect is almost the same as that of conventionally known cooling agents such as methyl-3- (1 menthyloxy) propane 1,2 diol.
  • the cooling effect can be easily measured by those skilled in the art according to methods well known in the art.
  • the suppression of the heartbeat odor of the refreshing agent used in the external preparation of the present invention is, for example, tested using 2-methyl 3- (1-menthyloxy) propane 1,2-diol as a comparative control. What is necessary is just to confirm that the refreshing agent has the same or lower odor than the above substances. Such confirmation can be performed by a sensory test, for example.
  • the refreshing agent used in the external preparation of the present invention does not substantially affect the percutaneous absorption rate of the medicinal component is known to those skilled in the art by the method specifically described in the examples of the present specification. Easy to check. Although the percutaneous absorption profile differs depending on the type and dosage form of the medicinal ingredient, it cannot be generally stated.For example, in the presence of the test cooling agent, the rate of increase in the percutaneous absorption rate of the medicinal ingredient from the external preparation is increased. Less than 250 percent, preferably less than 200 percent, more preferably less than 100 percent, particularly preferably less than 50 percent, and most preferably less than 30 percent compared to the absence of the test refreshing agent.
  • the percutaneous absorption rate of a medicinal ingredient is the rate at which the medicinal ingredient contained in the external preparation per unit time is applied to the skin, mucous membrane, or scalp, etc. Is shown by the amount transmitted.
  • the unit is gZcm 2 Zhr, and it is evaluated as the transmission speed.
  • the amount of the refreshing agent blended in the external preparation of the present invention is not particularly limited, but the refreshing agent used in the external preparation of the present invention does not substantially affect the transdermal absorption rate of the medicinal component. Therefore, it is possible to increase the blending ratio of the cooling agent with respect to the medicinal ingredient compared with the conventional external preparation, thereby making the external preparation of the present invention a high refreshing feeling.
  • it contains a cooling agent
  • the amount can be selected from the viewpoint of the refreshing feeling perceived by humans and its sustainability, for example, 0.0001 to 20% by weight, preferably 0.01 to 10% by weight based on the total weight of the composition of the external preparation. %, Most preferably about 0.1 to 5% by weight.
  • the form of the external preparation of the present invention is not particularly limited, and is conventionally used as an external preparation, for example, a patch, a patch, a patch, a reservoir-type patch, a stick, etc.
  • an external preparation in the form of a solid preparation such as a gel, a semi-solid preparation such as a gel ointment, an ointment, or a time preparation, a liquid such as a lotion or liniment, or a spray such as an aerosol or non-gas spray.
  • a solid preparation such as a gel, a semi-solid preparation such as a gel ointment, an ointment, or a time preparation
  • a liquid such as a lotion or liniment
  • a spray such as an aerosol or non-gas spray.
  • the method for producing the external preparation of the present invention is not particularly limited, and a conventional production method known to those skilled in the art can be adopted depending on the form of the external preparation.
  • the ability to use one or more pharmaceutical additives The necessity and type thereof are appropriately selected by those skilled in the art depending on the form of the preparation. It is possible.
  • aqueous bases such as macrogol
  • oily bases such as petrolatum and liquid paraffin
  • Arabic gum gelatin
  • water-soluble polymers such as salt, polybulal alcohol and polybulurpyrrolidone
  • antioxidants such as erythorbic acid, sodium erythorbate, hydroxy-sol, anhydrous sodium sulfite
  • preservatives coloring agents
  • pH adjusters the present invention is not limited to these.
  • the above components were mixed in a kneader, spread on a polyester film that had been subjected to a release treatment, covered with a polyester woven fabric, and transferred by pressure bonding to obtain a tape agent.
  • the above components were mixed in a kneader, spread on a polyester film that had been subjected to a release treatment, covered with a polyester woven fabric, and transferred by pressure bonding to obtain a tape agent.
  • the above components were mixed with a kneader, spread evenly on a non-woven fabric, and pressure-bonded with a polyester film as a release liner to obtain a knocking agent.
  • the above ingredients were mixed with a mixer to obtain a lotion agent.
  • the above ingredients were mixed with a mixer to obtain a lotion agent.
  • the above components were mixed in a mixer, placed in a pressure vessel, filled with dimethyl ether, and used as an aerosol agent.
  • a gel ointment was prepared by the same formulation and production method as in Example 5 except that 2-methyl-3- (1 menthyloxy) propane 1,2 diol was not blended.
  • a gel ointment was prepared by the same formulation and production method as in Example 5, except that 1-menthol was blended instead of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • a gel ointment was prepared by the same formulation and production method as in Example 6 except that 1-menthol was blended in place of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • a gel ointment was prepared using the same formulation and production method as in Example 7, except that 1-menthol was added instead of 2-methyl-3- (1 menthyloxy) propane 1,2 diol. Made.
  • a gel ointment was prepared by the same formulation and production method as in Example 8, except that 2-methyl-3- (1 menthyloxy) propane 1,2 diol was not blended.
  • a gel ointment was prepared by the same formulation and production method as in Example 8, except that 1-menthol was blended in place of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • a gel ointment was prepared by the same formulation and production method as in Example 9, except that 1-menthol was blended in place of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • a gel ointment was prepared by the same formulation and production method as in Example 10, except that 1-menthol was blended instead of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • a cataplasm was prepared by the same formulation and production method as in Example 4 except that 1-menthol was blended instead of 2-methyl-3- (1-menthyloxy) propane 1,2 diol.
  • the gel ointment of Examples 5 to 10 and the gel ointment of Comparative Examples 1 to 8 were subjected to a hairless mouse skin permeation test.
  • hairless mouse-extracted skin was attached to a Franz-type cell, 0.5 mL of the preparation was applied to the donor cell, and 4 mL of phosphate buffered saline was applied to the receiver cell.
  • the experiment was performed at 32 ° C. A portion of the receiver solution was collected at regular intervals, and the amount of drug that permeated the receiver was quantified by HPLC.
  • Test results Table 1 shows the permeation rate and lag time of ketoprofen, and Table 2 shows the permeation rate and lag time of indomethacin. [0040] [Table 1]
  • ketoprofen is used as the medicinal component
  • the permeation rate of 14.8 (gZcm 2 Zhr) in Comparative Example 1 in which no refreshing agent is added is compared with 2-methyl 3- (1-menthylo) as the refreshing agent.
  • Example 5 Example 6, and Example 7 in which 0.5%, 1.0%, and 2.0% by weight of xy) propane 1,2 diol were blended, the rate of increase in permeation rate was 30%, 51 %, 84%, almost no influence on the transdermal absorption rate.
  • the permeation rate of Comparative Example 5 in which no refreshing agent is blended is 16.5 (g / cm 2 / hr), whereas the refreshing agent is 2-methyl 3— (The rate of increase in permeation rate in Examples 8, 9, and 10 containing 1-menthoxy) propane 1,2 diol was 0.5% by weight, 1.0% by weight, and 2.0% by weight, respectively. %, 61%, and 2 20%, almost no influence on the transdermal absorption rate.
  • Example 4 As is apparent from the above results, the external preparation of Example 4 containing 2-methyl-3- (1 menthyloxy) propane-1,2 diol as a refreshing agent was compared with 1 menthol. Compared to Example 9, while maintaining the same refreshing intensity, the odor intensity was about 1/6.
  • the external preparation of the present invention is an external preparation containing a refreshing agent that suppresses an irritating odor such as a heart odor and does not substantially affect the percutaneous absorption rate of a medicinal ingredient. It can be suitably used as, for example.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une préparation médicinale destinée à un usage externe qui comprend (1) un ingrédient médicinal et (2) un réfrigérant (par ex. le 2-méthyl-3-(1-menthyloxy)propane-1,2-diol ou un dérivé de celui-ci) dont l’odeur de menthe est réduite et qui n’exerce quasiment aucun effet sur le taux d’absorption percutanée de l’ingrédient médicinal.
PCT/JP2005/021754 2004-11-29 2005-11-28 Preparation medicinale pour usage externe Ceased WO2006057375A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-343301 2004-11-29
JP2004343301 2004-11-29

Publications (1)

Publication Number Publication Date
WO2006057375A1 true WO2006057375A1 (fr) 2006-06-01

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ID=36498108

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/021754 Ceased WO2006057375A1 (fr) 2004-11-29 2005-11-28 Preparation medicinale pour usage externe

Country Status (2)

Country Link
TW (1) TW200631596A (fr)
WO (1) WO2006057375A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013184936A (ja) * 2012-03-08 2013-09-19 Naris Cosmetics Co Ltd 化粧料
CN109589281A (zh) * 2018-12-25 2019-04-09 澳宝化妆品（惠州）有限公司 一种含薄荷叶油的衣物用清凉喷雾剂及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09217083A (ja) * 1996-02-08 1997-08-19 Takasago Internatl Corp 清涼感改善剤
JP2002179517A (ja) * 2000-12-12 2002-06-26 Takasago Internatl Corp 温感組成物
WO2003074622A1 (fr) * 2002-03-01 2003-09-12 Takasago International Corporation Compositions refrigerantes, compositions auxiliaires refrigerantes et leurs utilisations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09217083A (ja) * 1996-02-08 1997-08-19 Takasago Internatl Corp 清涼感改善剤
JP2002179517A (ja) * 2000-12-12 2002-06-26 Takasago Internatl Corp 温感組成物
WO2003074622A1 (fr) * 2002-03-01 2003-09-12 Takasago International Corporation Compositions refrigerantes, compositions auxiliaires refrigerantes et leurs utilisations

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013184936A (ja) * 2012-03-08 2013-09-19 Naris Cosmetics Co Ltd 化粧料
CN109589281A (zh) * 2018-12-25 2019-04-09 澳宝化妆品（惠州）有限公司 一种含薄荷叶油的衣物用清凉喷雾剂及其制备方法

Also Published As

Publication number Publication date
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