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WO2000045782A1 - INHIBITEURS DE LA TESTOSTERONE-5α-REDUCTASE, STIMULANT DE LA POUSSE DES CHEVEUX OU COMPOSITIONS CAPILLAIRES NUTRITIVES ET COMPOSITIONS POUR PRODUITS COSMETIQUES BLANCHISSANTS - Google Patents

INHIBITEURS DE LA TESTOSTERONE-5α-REDUCTASE, STIMULANT DE LA POUSSE DES CHEVEUX OU COMPOSITIONS CAPILLAIRES NUTRITIVES ET COMPOSITIONS POUR PRODUITS COSMETIQUES BLANCHISSANTS Download PDF

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Publication number
WO2000045782A1
WO2000045782A1 PCT/JP2000/000504 JP0000504W WO0045782A1 WO 2000045782 A1 WO2000045782 A1 WO 2000045782A1 JP 0000504 W JP0000504 W JP 0000504W WO 0045782 A1 WO0045782 A1 WO 0045782A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
compound
compositions
tsr
hair growth
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/JP2000/000504
Other languages
English (en)
Japanese (ja)
Inventor
Kokki Sakai
Ryuichiro Kondo
Kuniyoshi Shimizu
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.)
Kansai Koso KK
Original Assignee
Kansai Koso KK
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 Kansai Koso KK filed Critical Kansai Koso KK
Priority to AU23228/00A priority Critical patent/AU2322800A/en
Publication of WO2000045782A1 publication Critical patent/WO2000045782A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • 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
    • A61K8/31—Hydrocarbons
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention provides a testosterone -5H-reductase (hereinafter abbreviated as TSR) activity inhibitor which can be expected to have a hair-growth / hair-growing action, a sebum secretion inhibitory action, a whitening action, etc., and which can be added to various cosmetics and pharmaceuticals. And a composition for hair growth and hair growth and a composition for whitening cosmetics containing the TSR activity inhibitor.
  • TSR testosterone -5H-reductase
  • D ⁇ 5 -dihydrotestosterone
  • TSR 5 -dihydrotestosterone
  • This DHT is known to have several to several tens of times more potent androgenic effects than testosterone.
  • This DHT binds to an intracellular receptor and acts on hair mother cells to suppress cell division. It is believed that doing so hinders hair growth.
  • TSR is expressed in melanocytes in vitro, and it is suggested that inhibition of this TSR activity may suppress melanin production, and that whitening effects can be expected (" THE JOURNAL OF INVESTIGATIVE DERMATOLOGY "Vol.110'No.1, JANUAEY (1998)).
  • TSR activity inhibitors by inhibiting the TSR activity, a sebum secretion inhibitory effect and the like can be expected, and attempts have been made to blend TSR activity inhibitors into various cosmetics and pharmaceuticals, and some of them have been commercialized.
  • the object of the present invention is to provide various cosmetics and pharmaceuticals with various An object of the present invention is to provide a ⁇ SR activity inhibitor which can be expected to have a seed action, and a hair growth / hair restoration composition and a whitening cosmetic composition containing the TSR activity inhibitor.
  • a compound having a prenyl group has TSR activity inhibitory ability. Further, as such a compound, a compound having a prenyl group and a polar group such as a hydroxyl group is preferable, and in particular, a compound having a prenyl group contained in a thick timber of the genus Artocarpus is preferable. The inventors have found that they have inhibitory ability and completed the present invention.
  • a TSR activity inhibitor comprising a compound having a prenyl group.
  • composition for hair growth and hair growth comprising the TSR activity inhibitor.
  • composition for whitening cosmetics containing the TSR activity inhibitor.
  • the TSR activity inhibitor of the present invention contains a compound having a prenyl group as an active ingredient.
  • a compound having a prenyl group and a polar group such as a hydroxyl group is preferable.
  • a compound having a prenyl group included in Moraceae and a compound having a prenyl group included in a plant of the genus Aitocarims are preferable.
  • the molecular weight of these compounds is preferably from 100 to 100 in number average molecular weight.
  • Examples of the above-mentioned plants of the genus Grass include the genus Fig (Ficus), the genus Altocarpus (Artocarpusl genus iBroussonetia), and the genus Cucuria (Cudria). These fruits are used for food and medicine.
  • the altocarpus (A ocarpus) plant is an evergreen tree native to the tropics, and is eaten in the place of origin by growing its fruit or cooking it.
  • altocalcus A. incisus which contains a compound having a prenyl group, is toxic to cultured cells at 100 ppm. And low toxicity to the human body.
  • Examples of the compound having a prenyl group include compounds represented by the following structural formulas 1-192. However, in the formula, R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, an acyl group or a darkosyl group.
  • the TSR activity inhibitor of the present invention may contain a compound having a prenyl group capable of inhibiting TSR activity. Since this TSR activity inhibitor can be expected to have a hair-growing action, a hair-growing action, a whitening action, a sebum secretion-suppressing action, etc. Formulations, shampoos, rinses, hair tonics, conditioners, scalp treatments, foundations, bath preparations, body cleansers, lotions, facial cleansers, ishiken, nutritional creams, skin formulas and other cosmetics and pharmaceuticals Thereby, a desired effect can be exhibited.
  • the blending ratio and form of the TSR activity inhibitor in preparing a cosmetic can be appropriately selected depending on the type of the above-mentioned cosmetics and the like. It is preferably at least 1% by weight.
  • the composition for hair growth and hair growth according to the present invention contains the TSR activity inhibitor, and is used, for example, for hair growth, hair growth, hair lotion, hair packs, tonics, shampoos, and hair and scalp such as rinses. It can be incorporated into various cosmetics and the like to be used.
  • the compounding ratio of the TSR activity inhibitor It is only necessary that the content can be adjusted to 0.001% by weight or more when it is added to the ingredients.
  • the hair-growth / hair-growing composition of the present invention may contain various known materials, which are usually added to cosmetics that are expected to grow and grow hair, if necessary. For example, other hair-growth, hair-growing agents, antibacterial agents, cooling agents, humectants, or mixtures thereof.
  • hair restorers include, for example, vitamin B 6 , vitamin E and its derivatives, glycyrrhetinic acid and its derivatives, nicotinic esters such as benzyl nicotinate, cyclosporins, carpronium chloride, cepharanthin, oxen Delon, diazoxide, minoxidil, ethinyl estradiol, estradiol, animal and plant extracts containing these, and the like can be used, and they can be used alone or as a mixture.
  • vitamin B 6 vitamin E and its derivatives
  • glycyrrhetinic acid and its derivatives nicotinic esters
  • nicotinic esters such as benzyl nicotinate, cyclosporins, carpronium chloride, cepharanthin, oxen Delon, diazoxide, minoxidil, ethinyl estradiol, estradiol, animal and plant extracts
  • antibacterial agent examples include hinokitiol, pyrotatoolamine, pyrothione zinc, hexcloclofen, phenol, benzalkonium chloride, cetylpyridinium chloride, pendecylenic acid, trichlorocarbanilide, and mixtures thereof.
  • cooling agent examples include menthol and the like.
  • humectants include polyhydric alcohols such as glycerin, propylene glycol, 1,3-butylene glycol, sonorebitone, man-tonore, polyethylene glycol, zipper pyrendalcol; amine acids, sodium lactate, pyrrolidone NMF components such as sodium carboxylate; hyaluronic acid; collagen; elastin; chondroitin sulfate; fibronectin; ceramides; heparin-like substances; water-soluble high-molecular substances such as chitosan or mixtures thereof.
  • polyhydric alcohols such as glycerin, propylene glycol, 1,3-butylene glycol, sonorebitone, man-tonore, polyethylene glycol, zipper pyrendalcol
  • amine acids sodium lactate, pyrrolidone NMF components such as sodium carboxylate; hyaluronic acid; collagen; elastin; chondroitin sulfate; fibronectin;
  • the hair restoring / hair growing composition of the present invention may further contain various additives.
  • additives include fats and oils, surfactants, alcohols, fatty acids, preservatives, antioxidants, pigments, fragrances, ultraviolet absorbers, chelating agents, pH regulators, buffers, and purified water. The amount can be appropriately selected.
  • the composition for whitening cosmetics of the present invention contains a TSR activity inhibitor containing the compound having a prenyl group, and includes, for example, whitening agents, body lotions, emulsions, cosmetic waters, packs, foundations, and baths. , Body cleanser, face wash, stone cleaner, It can be blended with various cosmetics and the like used for skin such as creams and skin oils.
  • Examples of the compound having a prenyl group include the compounds listed in Structural Formulas 1 to 192, and examples of the whitening cosmetic composition include compounds represented by the Structural Formulas 1891 to 91.
  • the embodiment which does not include the compound to be used is exemplified.
  • the compounding ratio of the TSR activity inhibitor may be 0.0001% by weight or more when compounded with the above various cosmetics.
  • the composition for whitening cosmetics of the present invention may be blended with a known whitening agent, anti-wrinkle agent, humectant or a mixture thereof.
  • whitening agents examples include kojic acid, ascorbic acid, hydroquinone, thiol compounds, and mixtures thereof.
  • the whitening cosmetic composition of the present invention may contain, if necessary, fats and oils, surfactants, alcohols, fatty acids, preservatives, bactericides, thickeners, anti-inflammatory agents, antioxidants, and pigments. , Fragrance, water-soluble polymer, UV absorber, chelating agent, pH adjuster, buffer, purified water Other components can be appropriately blended.
  • the TSR activity inhibitor of the present invention contains a compound having a prenyl group as an active ingredient, and can be expected to exert various actions caused by TSR activity inhibition when blended in various cosmetics and pharmaceuticals.
  • the composition for hair growth and hair growth and the composition for whitening cosmetics of the present invention can be blended with various cosmetics in view of hair growth and hair growth or whitening.
  • the enzymatic activity using the microsomes (TSR) derived from female rat liver shown below was measured, and the TSR activity of each compound was measured. The inhibitory ability was measured.
  • TSR microsomes
  • the enzymatic activity was determined in a sodium phosphate buffer (pH 6.5) at a concentration of 100 mmol / L at a concentration of 150 zmol / L testosterone at the start of the enzymatic reaction.
  • / L dithiothreitol was added to each and pre-incubated at 37 ° C. After 10 minutes, add NADPH so that the concentration at the start of the enzymatic reaction is 1667 ⁇ 1 ZL, and then add the microsomal solution so that the added protein amount is 0.25 mg.
  • 3 Mo 1 ZL of NaOH solution was added to 1 Z30 volume of the reaction system to terminate the reaction. From this reaction system, dihydrotestosterone was extracted, the amount of reaction produced was measured by mass spectrometry (GC_mass spectrometry), and the enzyme reaction rate was determined.
  • the TSR activity inhibitory activity is measured by adding the compounds represented by Structural Formulas 1 to 192 in the above enzyme activity measurement before pre-incubation so that the concentration at the start of each reaction becomes 100 ppm.
  • the enzyme reaction rate was measured in the same manner as in the other conditions, and the enzyme reaction rate was measured when the above compound represented by the structural formulas 1-192 was not contained.
  • the inhibition rate was determined by calculation from the ratio with the enzyme reaction rate measured above. Tables 1 and 2 show the results.
  • TSR activity inhibitory ability of the compounds having no prenyl group represented by the following structural formulas A to E was measured in the same manner as in Example 1. Table 3 shows the results.
  • a compound having a prenyl group represented by the above formula (188) wherein R is a hydrogen atom can Extracted and purified from the world by conventional methods.
  • a pigmentation inhibition test shown below was performed using these test solutions to evaluate the whitening effect of each test solution. Table 4 shows the results.
  • This predetermined location was determined so that all the liquid could be applied separately to the back of the same guinea pig, and the location of the separation was varied depending on the guinea pig.
  • the evaluation of the pigmentation inhibitory effect was performed by visually observing the back of each guinea pig on the 15th, 22nd, 29th, and 35th days after the start of the application of the test solution, and by coloration. The evaluation was performed by using a color difference meter (manufactured by Minolta Co., Ltd., CR-100) to evaluate the change in the degree of blackening of the skin irradiated with ultraviolet rays.
  • the degree of pigmentation was divided into five levels, and the inhibition rate in each guinea pig on each evaluation day was determined, and the average value was used as the evaluation result.
  • the suppression rate was obtained from the measurement results at a predetermined location on each guinea pig on each evaluation day, and the average value was used as the evaluation result.
  • the reference for each measurement was based on the back of each guinea pig to which the test solution was not applied, which was irradiated with ultraviolet rays.
  • test solution of the present invention showed a whitening effect superior to kojic acid, which is known to have a whitening effect, in any of the evaluation methods.

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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)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Toxicology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des inhibiteurs de l'activité testostérone-5α-réductase, un stimulant de la pousse des cheveux ou des compositions capillaires nutritives et des compositions pour produits cosmétiques blanchissants. On attend de ces inhibiteurs qu'ils exercent divers effets imputables à l'inhibition de l'activité testostérone-5α-réductase. On se propose donc de les intégrer à divers produits cosmétiques et médicaments, et notamment des inhibiteurs de l'activité testostérone-5α-réductase, un stimulant de la pousse des cheveux ou des compositions capillaires nutritives et des compositions pour produits cosmétiques blanchissants, lesquels produits cosmétiques et médicaments contiennent des composés prénylés.
PCT/JP2000/000504 1999-02-02 2000-01-31 INHIBITEURS DE LA TESTOSTERONE-5α-REDUCTASE, STIMULANT DE LA POUSSE DES CHEVEUX OU COMPOSITIONS CAPILLAIRES NUTRITIVES ET COMPOSITIONS POUR PRODUITS COSMETIQUES BLANCHISSANTS Ceased WO2000045782A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU23228/00A AU2322800A (en) 1999-02-02 2000-01-31 Testosterone-5alpha-reductase inhibitors, hair growth stimulant/hair nourishmentcompositions and compositions for whitening cosmetics

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/25503 1999-02-02
JP2550399 1999-02-02

Publications (1)

Publication Number Publication Date
WO2000045782A1 true WO2000045782A1 (fr) 2000-08-10

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Country Status (2)

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AU (1) AU2322800A (fr)
WO (1) WO2000045782A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008020490A1 (fr) * 2006-08-17 2008-02-21 Kansai Koso Co., Ltd. Dérivé de l'artocarpine ou composé similaire à l'artocarpine et composition de pousse/repousse des cheveux, composition cosmétique de blanchiment de la peau, produit pharmaceutique servant d'agent anticancéreux, antiphlogistique/analgésique, antipyrétique ou antiallergique et
WO2008020491A1 (fr) * 2006-08-18 2008-02-21 Kansai Koso Co., Ltd. Agent thérapeutique pour lésion cutanée pigmentée
US7629375B2 (en) 2001-07-23 2009-12-08 Johnson & Johnson Consumer Companies, Inc. Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
JP2010515725A (ja) * 2007-01-11 2010-05-13 ビオスペクトルム，インコーポレイテッド アルテミシニンを含む皮膚美白用組成物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01313414A (ja) * 1988-05-27 1989-12-18 Beijin Riiyuen Riiyon Fuashiyue Guufuen Youshien Gonsuu 頭部化粧料
JPH03188019A (ja) * 1989-12-15 1991-08-16 Shiseido Co Ltd テストステロン―５α―レダクターゼ阻害剤
JPH03284612A (ja) * 1990-03-30 1991-12-16 Narisu Keshohin:Kk チロシナーゼ活性抑制剤、抗酸化剤
EP0540854A2 (fr) * 1991-09-10 1993-05-12 Sansho Seiyaku Co., Ltd. Préparation pour promouvoir la pousse de cheveux
JPH1017455A (ja) * 1996-07-03 1998-01-20 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
JPH1017456A (ja) * 1996-07-03 1998-01-20 Kansai Kouso Kk 細胞活性剤、化粧料及び養毛料
JPH1072330A (ja) * 1996-09-03 1998-03-17 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01313414A (ja) * 1988-05-27 1989-12-18 Beijin Riiyuen Riiyon Fuashiyue Guufuen Youshien Gonsuu 頭部化粧料
JPH03188019A (ja) * 1989-12-15 1991-08-16 Shiseido Co Ltd テストステロン―５α―レダクターゼ阻害剤
JPH03284612A (ja) * 1990-03-30 1991-12-16 Narisu Keshohin:Kk チロシナーゼ活性抑制剤、抗酸化剤
EP0540854A2 (fr) * 1991-09-10 1993-05-12 Sansho Seiyaku Co., Ltd. Préparation pour promouvoir la pousse de cheveux
JPH1017455A (ja) * 1996-07-03 1998-01-20 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
JPH1017456A (ja) * 1996-07-03 1998-01-20 Kansai Kouso Kk 細胞活性剤、化粧料及び養毛料
JPH1072330A (ja) * 1996-09-03 1998-03-17 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7629375B2 (en) 2001-07-23 2009-12-08 Johnson & Johnson Consumer Companies, Inc. Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
WO2008020490A1 (fr) * 2006-08-17 2008-02-21 Kansai Koso Co., Ltd. Dérivé de l'artocarpine ou composé similaire à l'artocarpine et composition de pousse/repousse des cheveux, composition cosmétique de blanchiment de la peau, produit pharmaceutique servant d'agent anticancéreux, antiphlogistique/analgésique, antipyrétique ou antiallergique et
WO2008020491A1 (fr) * 2006-08-18 2008-02-21 Kansai Koso Co., Ltd. Agent thérapeutique pour lésion cutanée pigmentée
JP2010515725A (ja) * 2007-01-11 2010-05-13 ビオスペクトルム，インコーポレイテッド アルテミシニンを含む皮膚美白用組成物

Also Published As

Publication number Publication date
AU2322800A (en) 2000-08-25

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