JPH02142717A - Hair nouring cosmetic - Google Patents
Hair nouring cosmeticInfo
- Publication number
- JPH02142717A JPH02142717A JP29532288A JP29532288A JPH02142717A JP H02142717 A JPH02142717 A JP H02142717A JP 29532288 A JP29532288 A JP 29532288A JP 29532288 A JP29532288 A JP 29532288A JP H02142717 A JPH02142717 A JP H02142717A
- Authority
- JP
- Japan
- Prior art keywords
- hair
- cosmetic
- nouring
- chalcone
- formula
- 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.)
- Pending
Links
- 210000004209 hair Anatomy 0.000 title claims abstract description 38
- 239000002537 cosmetic Substances 0.000 title claims abstract description 18
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000005513 chalcones Nutrition 0.000 claims abstract description 13
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims abstract description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 8
- 150000001788 chalcone derivatives Chemical class 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 27
- 230000003779 hair growth Effects 0.000 abstract description 19
- 239000000203 mixture Substances 0.000 abstract description 11
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 abstract description 8
- -1 methoxy, ethoxy Chemical group 0.000 abstract description 7
- 230000002265 prevention Effects 0.000 abstract description 7
- 239000006071 cream Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000004615 ingredient Substances 0.000 abstract description 5
- 230000001256 tonic effect Effects 0.000 abstract description 3
- 239000006210 lotion Substances 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 206010022998 Irritability Diseases 0.000 abstract 1
- 150000001789 chalcones Chemical class 0.000 abstract 1
- 230000035617 depilation Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 17
- GVSPXQVUXHMUMA-MDWZMJQESA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GVSPXQVUXHMUMA-MDWZMJQESA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000010998 test method Methods 0.000 description 8
- 208000001840 Dandruff Diseases 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- 229940088597 hormone Drugs 0.000 description 6
- 239000005556 hormone Substances 0.000 description 6
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 6
- 230000003658 preventing hair loss Effects 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 6
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 4
- 201000004384 Alopecia Diseases 0.000 description 4
- 235000002566 Capsicum Nutrition 0.000 description 4
- 240000008574 Capsicum frutescens Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229960003473 androstanolone Drugs 0.000 description 4
- 239000001390 capsicum minimum Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 210000004761 scalp Anatomy 0.000 description 4
- 229960003604 testosterone Drugs 0.000 description 4
- 229940098465 tincture Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 229960001238 methylnicotinate Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYKDOWJROLHYOT-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1O LYKDOWJROLHYOT-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 206010039792 Seborrhoea Diseases 0.000 description 2
- 206010068168 androgenetic alopecia Diseases 0.000 description 2
- 201000002996 androgenic alopecia Diseases 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003676 hair loss Effects 0.000 description 2
- 208000024963 hair loss Diseases 0.000 description 2
- 210000003128 head Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000015961 tonic Nutrition 0.000 description 2
- 229960000716 tonics Drugs 0.000 description 2
- MUMGGOZAMZWBJJ-WLRIMQDWSA-N (8r,9s,10r,13s,14s,17s)-10,13-dimethyl-17-oxidanyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=[14CH]1 MUMGGOZAMZWBJJ-WLRIMQDWSA-N 0.000 description 1
- UENLHUMCIOWYQN-UHFFFAOYSA-N 2'-Hydroxy-6'-methoxyacetophenone Chemical compound COC1=CC=CC(O)=C1C(C)=O UENLHUMCIOWYQN-UHFFFAOYSA-N 0.000 description 1
- UTIGWEHMQWYSCZ-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)C=CC1=CC=CC(O)=C1 UTIGWEHMQWYSCZ-UHFFFAOYSA-N 0.000 description 1
- PRFZEWJVEGPUJS-UHFFFAOYSA-N 4-ethoxy-2-methoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C(OC)=C1 PRFZEWJVEGPUJS-UHFFFAOYSA-N 0.000 description 1
- 208000019300 CLIPPERS Diseases 0.000 description 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 240000004371 Panax ginseng Species 0.000 description 1
- 235000002789 Panax ginseng Nutrition 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000021930 chronic lymphocytic inflammation with pontine perivascular enhancement responsive to steroids Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007102 metabolic function Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、カルコン又はカルコン誘導体の１種または２
種以上を含有してなる養毛化粧料に関して、詳しくは、
男性ホルモン（テストステロン）の活性化酵素である５
α−リダクターゼの活性阻害能を有し、育毛効果、脱毛
予防効果及びふけ防止効果に優れた養毛化粧料に関する
。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention provides one or two types of chalcone or chalcone derivatives.
For more information on hair nourishing cosmetics containing seeds or more, please see
5 is an enzyme that activates the male hormone (testosterone)
The present invention relates to a hair nourishing cosmetic that has the ability to inhibit α-reductase activity and is excellent in hair growth, hair loss prevention, and dandruff prevention effects.
〔従来の技術及び発明が解決しようとする課題〕従来よ
り、トウガラシチンキ、センブリエキス、朝鮮ニンジン
エキス、ニコチン酸、ニコチン酸メチル等の頭皮の血行
促進物質等を配合してなる養毛化粧料は知られている。[Prior art and problems to be solved by the invention] Hair nourishing cosmetics containing scalp blood circulation promoting substances such as capsicum tincture, Jasperia japonica extract, Korean ginseng extract, nicotinic acid, methyl nicotinate, etc. have conventionally been used. Are known.
しかし、育毛、脱毛防止、ふけ防止等の効果を充分に発
現する程に有効なる物質の発見にまでは至っていない。However, a substance that is effective enough to fully exhibit effects such as hair growth, hair loss prevention, and dandruff prevention has not yet been discovered.
近年、育毛に関し、ホルモンの関与が示唆されている。In recent years, hormones have been suggested to be involved in hair growth.
つまり、毛母細胞を含めた毛包において、男性ホルモン
（テストステロン）が、５α−リダクターゼ（△４−３
−ケトステロイド−５α−オキシドリダクターゼ）によ
り、活性型男性ホルモン（ジヒドロテストステロン）に
活性化され、さらに受容体と結合し、核に取り込まれ、
ＤＮＡレベルで情報を伝達する。伝達された情報により
、ケラチン合成に関連する酵素合成が調節され、毛髪ケ
ラチン合成を抑制し、最終的に脱毛を促進させる。した
がって、養毛剤開発にあたり、男性ホルモン活性化酵素
である５α−リダクターゼの活性阻害物質の検索が注目
されている。In other words, in hair follicles including hair matrix cells, male hormone (testosterone) is activated by 5α-reductase (△4-3
-Ketosteroid-5α-oxidoreductase) is activated to the active male hormone (dihydrotestosterone), which further binds to the receptor and is taken into the nucleus.
Transmits information at the DNA level. The transmitted information modulates enzyme synthesis related to keratin synthesis, inhibits hair keratin synthesis, and ultimately promotes hair loss. Therefore, in the development of hair tonics, the search for substances that inhibit the activity of 5α-reductase, which is an androgen activating enzyme, is attracting attention.
本発明は、男性ホルモンが活性化されるのを阻害し、育
毛、脱毛予防及びふけ防止等の効果に優れた養毛化粧料
を提供することを目的としている。An object of the present invention is to provide a hair-growth cosmetic that inhibits the activation of male hormones and has excellent effects on hair growth, hair loss prevention, and dandruff prevention.
本発明は、カルコン又はカルコン誘導体の１種または２
種以上を含有してなる養毛化粧料である。The present invention provides one or two chalcone or chalcone derivatives.
This is a hair nourishing cosmetic containing at least seeds.
下記の一般式（１）
（式中、Ｒ１〜Ｒ７は、水素原子、水酸基、メチル基、
メトキシ基、エトキシ基、イソプロピル基を示す。）
で示され、例えば３−ヒドロキシ−４′−メトキシカル
コン、２′−ヒドキシ−４−イソプロピル６′−メチル
カルコン、３．３’ −ジメチル２．２’、４’−）リ
ヒドロキシカルコン、２４′−ジメチル−２−メトキシ
カルコン、２−ヒドロキシ−３，２’、４’、５’−テ
トラメチルカルコン、３，４−ジェトキシ−４′−ヒド
ロキシ−３′−メトキシカルコン、４．２′ −ジメチ
ル−４′−ヒドロキシ−６−イソプロピルカルコン、２
．２’、５’ −トリメチルカルコン、４２’、６’
−トリヒドロキシ−２，３，４’ −トリメトキシカル
コン、２，４′ −ジヒドロキシ３．４．．２’−トリ
メトキシカルコン、３，２′ジヒドロキシ−４，３’
、６’ −１−リメチルカルコン、２．２′−ジヒドロ
キシ−４，３’−ジイソプロピルカルコン、４，４′−
ジメトキシ３．２’、５’−）リヒドロキシカルコン、
４４′−ジヒドロキシ−３′−イソプロピルカルコン、
３．２’ 、４’ ５’−テトラメトキシカルコン、
４，４′−ジヒドロキジー３．２／ ５／トリイソ
プロピルカルコン、４−工１・；トレー２′ヒドロキシ
−２−イソプロピル−４′−メトキシカルコン等が挙げ
られる。The following general formula (1) (wherein R1 to R7 are a hydrogen atom, a hydroxyl group, a methyl group,
Indicates methoxy group, ethoxy group, and isopropyl group. ), such as 3-hydroxy-4'-methoxychalcone, 2'-hydroxy-4-isopropyl 6'-methylchalcone, 3,3'-dimethyl 2,2',4'-)rihydroxychalcone, 24 '-dimethyl-2-methoxychalcone, 2-hydroxy-3,2',4',5'-tetramethylchalcone, 3,4-jethoxy-4'-hydroxy-3'-methoxychalcone, 4.2'- Dimethyl-4'-hydroxy-6-isopropyl chalcone, 2
．． 2', 5'-trimethylchalcone, 42', 6'
-trihydroxy-2,3,4'-trimethoxychalcone, 2,4'-dihydroxy3.4. ．． 2'-trimethoxychalcone, 3,2'dihydroxy-4,3'
, 6'-1-limethylchalcone, 2,2'-dihydroxy-4,3'-diisopropylchalcone, 4,4'-
dimethoxy 3.2',5'-)lihydroxychalcone,
44'-dihydroxy-3'-isopropyl chalcone,
3.2',4'5'-tetramethoxychalcone,
Examples include 4,4'-dihydroxy-3.2/5/triisopropylchalcone, 4-dihydroxy-2-isopropyl-4'-methoxychalcone, and the like.
本発明のカルコン又はカルコン誘導体は、次の式（２）
（式中、Ｒ２−Ｒ４は、水素原子、水酸基、メチル基、
メトキシ基、エトキシ基、イソプロピル基を示す。）
の化合物と式（３）
（式中、Ｒｗｒ ” Ｒｑ は、水素原子、水酸基、メ
チル基、メトキシ基、エトキシ基、イソプロピル基を示
す。）
の化合物を有機溶媒中、塩基を用いて縮合させて、本発
明に用いられるカルコン又はカルコン誘導体、即ち式（
１）
（式中、Ｒ，〜Ｒ９は、水素原子、水酸基、メチル基、
メトキシ基、エトキシ基、イソプロピル基を示す。）
の化合物を得る。The chalcone or chalcone derivative of the present invention has the following formula (2) (wherein R2-R4 are a hydrogen atom, a hydroxyl group, a methyl group,
Indicates methoxy group, ethoxy group, and isopropyl group. ) and the compound of formula (3) (wherein, Rwr '' Rq represents a hydrogen atom, a hydroxyl group, a methyl group, a methoxy group, an ethoxy group, or an isopropyl group) in an organic solvent using a base. Therefore, the chalcone or chalcone derivative used in the present invention, that is, the formula (
1) (wherein R, ~R9 are a hydrogen atom, a hydroxyl group, a methyl group,
Indicates methoxy group, ethoxy group, and isopropyl group. ) to obtain the compound.
具体的な例として、カルコン誘導体■〜■の製造法を下
記に示す。As specific examples, methods for producing chalcone derivatives (1) to (2) are shown below.
カルコン誘導体Ｉ
４−メトキシアセトフェノンｌ ５． Ｏｇと３−ヒド
ロキシヘンズアルデヒド１２．２ ｇをメタノール５０
ｍ ｊ＋に溶解させた後、０°Ｃに冷却し、飽和水酸
化カルシウム・エタノール溶液８０ｍｊ＋を加え、窒素
気流下、Ｏ′Ｃで３０分間、続いて室温で４日間撹拌し
た。反応終了後、冷却しながら、この反応液に３Ｎ塩酸
を加え、徐々に酸性にし、析出した沈澱物を濾取し、メ
タノールから再結晶を行い、黄色結晶として、３−ヒド
ロキシ−４′−メトキシカルコン１０．３ ｇを得た。Chalcone derivative I 4-methoxyacetophenone I 5. 12.2 g of Og and 3-hydroxyhenzaldehyde in 50 g of methanol
After dissolving in mj+, the mixture was cooled to 0°C, 80 mj+ of saturated calcium hydroxide in ethanol was added, and the mixture was stirred at O'C for 30 minutes under a nitrogen stream, then at room temperature for 4 days. After the reaction was completed, 3N hydrochloric acid was added to the reaction solution while cooling to make it gradually acidic. The precipitate was collected by filtration and recrystallized from methanol to give 3-hydroxy-4'-methoxy as yellow crystals. 10.3 g of chalcone was obtained.
（収率５２．１％）カルコン誘導体■
２−ヒドロキシ−６−メトキシアセトフェノン４．０ｇ
と４−イソプロピルヘンズアルデヒド５．４ｇをメタノ
ール３０ｍ６に溶解し、飽和水酸化ナトリウム・メタノ
ール溶液を加えて、室温で１日撹拌し反応させた。反応
終了後、反応混合物を希塩酸で注意深く中和し、酢酸エ
チル１．５ ｍ ｌで抽出し、酢酸エチル層を順次、水
洗（３００ｍｉ！ｘ４）、飽和食塩水と振！（３００ｍ
Ａｘ２）、無水硫酸す） ＩＪウムで乾燥、濾過、溶媒
留去して、黄色物質の２′−ヒドロキシ−４−イソプロ
ピル６′−メチルカルコン３．４ｇを得た。（収率４８
．０ ％）
カルコン誘導体■
４−ヒドロキシ−３−メトキシアセトフェノン７．２ｇ
と４−エトキシ−３−ヒドロキシヘンズアルデヒド６．
８ｇをメタノール４０ｍｊ！に溶解し、５％水酸化カリ
ウム溶液４０ｍ１を滴下し２分間撹拌した。３Ｎ塩酸に
て中和し、反応液をエーテルにて抽出した。このエーテ
ル層を水洗し、無水硫酸ナトリウムで乾燥、濾過、溶媒
留去した。さらに得られた残渣をヘキサンと酢酸エチル
の混合溶媒より再結晶し、黄色結晶の３．４′−ジヒド
ロキシ−４−エトキシ−３′−メトキシカルコンを得た
。（収率５６．０％）
カルコン誘導体■
２−ヒドロキシ−４−メチルアセトフェノン６．３と４
−エトキシ−２−メトキシベンズアルデヒド７．８ｇを
メタノール４０ｍ１に溶解し、飽和水酸化カリウム・エ
タノール溶液１００ｍＡを加え、２４時間撹拌し反応さ
せた。反応終了後、反応液を６Ｎ塩酸にてｐＨ５〜７に
調整し、析出した沈澱物を濾取し、水洗後乾燥して、黄
色針状晶４−エトキシ−２′−ヒドロキシ−６−メトキ
シ４′−メチルカルコン４．７ｇを得た。（収率６０．
０％）
カルコン誘導体Ｉ〜■の構造式を示す。(Yield 52.1%) Chalcone derivative■ 2-hydroxy-6-methoxyacetophenone 4.0g
and 5.4 g of 4-isopropylhenzaldehyde were dissolved in 30 m6 of methanol, a saturated sodium hydroxide/methanol solution was added, and the mixture was stirred at room temperature for one day to react. After the reaction, the reaction mixture was carefully neutralized with diluted hydrochloric acid, extracted with 1.5 ml of ethyl acetate, and the ethyl acetate layer was sequentially washed with water (300 mi! x 4) and shaken with saturated brine! (300m
Ax2), anhydrous sulfuric acid) was dried over IJum, filtered, and the solvent was distilled off to obtain 3.4 g of 2'-hydroxy-4-isopropyl 6'-methyl chalcone as a yellow substance. (Yield 48
．． 0%) Chalcone derivative■ 4-hydroxy-3-methoxyacetophenone 7.2g
and 4-ethoxy-3-hydroxyhenzaldehyde6.
8g to 40mj of methanol! 40 ml of 5% potassium hydroxide solution was added dropwise and stirred for 2 minutes. The reaction solution was neutralized with 3N hydrochloric acid and extracted with ether. This ether layer was washed with water, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off. The resulting residue was further recrystallized from a mixed solvent of hexane and ethyl acetate to obtain yellow crystals of 3,4'-dihydroxy-4-ethoxy-3'-methoxychalcone. (Yield 56.0%) Chalcone derivative ■ 2-hydroxy-4-methylacetophenone 6.3 and 4
-Ethoxy-2-methoxybenzaldehyde (7.8 g) was dissolved in methanol (40 ml), saturated potassium hydroxide/ethanol solution (100 mA) was added, and the mixture was stirred for 24 hours to react. After the reaction, the pH of the reaction solution was adjusted to 5 to 7 with 6N hydrochloric acid, and the precipitate was collected by filtration, washed with water, and dried to give yellow needle-like crystals of 4-ethoxy-2'-hydroxy-6-methoxy 4. 4.7 g of '-methylchalcone was obtained. (Yield 60.
0%) The structural formulas of chalcone derivatives I to ① are shown.
以上の様にして、カルコン誘導体を製造することができ
る。A chalcone derivative can be produced in the manner described above.
本発明の養毛化粧料に含有させるカルコン又はカルコン
誘導体は、適度な経皮吸収性を有する為、頭皮内におけ
る該薬物の有効濃度を持続するものであって、皮膚刺激
性も低く、５α−リダクターゼ活性阻害能を有するもの
である。この５α−リダクターゼ活性阻害能が、毛母細
胞における活性型男性ホルモン（ジヒドロテストステロ
ン）産生を抑制することにより、育毛、脱毛予防効果を
発現し、更には、頭皮代謝機能を正常化して、ふけ防止
効果を高めるものと推察される。Since the chalcone or chalcone derivative contained in the hair-growth cosmetic of the present invention has appropriate percutaneous absorption, it maintains the effective concentration of the drug in the scalp, has low skin irritation, and has 5α- It has the ability to inhibit reductase activity. This ability to inhibit 5α-reductase activity suppresses the production of active male hormone (dihydrotestosterone) in hair matrix cells, thereby promoting hair growth and preventing hair loss. Furthermore, it also normalizes scalp metabolic function and prevents dandruff. It is assumed that this increases the effectiveness.
カルコン又はカルコン誘導体の配合量は、本発明の養毛
化粧料の組成物の全重量に対して大略０．０５〜１．０
重量％（以下ｗｔ％と略記する。）であればよく、好ま
しくはＯ１１〜０．７ ｗ ｔ％である。配合量が０．
０５ ｗ ｔ％未満では、本発明の目的とする効果に充
分でなく、一方１．Ｑ ｗ ｔ％を超えても、その増加
分に見合った効果の向上は望めないものである。The amount of chalcone or chalcone derivative blended is approximately 0.05 to 1.0 based on the total weight of the hair nourishing cosmetic composition of the present invention.
It may be any weight% (hereinafter abbreviated as wt%), and preferably O11 to 0.7 wt%. The blending amount is 0.
If the amount is less than 0.05 wt%, it is not sufficient to achieve the desired effect of the present invention, and on the other hand, 1. Even if it exceeds Q w t%, it cannot be expected to improve the effect commensurate with the increase.
本発明の養毛化粧料は、常法に従って、ヘアートニック
、ヘアーローション、ヘアークリーム等の剤型にするこ
とが可能である。The hair nourishing cosmetic composition of the present invention can be formulated into hair tonics, hair lotions, hair creams, and the like according to conventional methods.
抗酸化剤等を本発明の目的を達成する範囲内で適宜配合
することができる。Antioxidants and the like may be added as appropriate within the range that achieves the purpose of the present invention.
以下、実施例及び比較例に基づいて本発明を詳説する。 Hereinafter, the present invention will be explained in detail based on Examples and Comparative Examples.
尚、実施例に記載の５α−リダクターゼ活性阻害試験法
、マウス毛成長促進効果試験法、ヒト頭皮毛成長促進効
果試験法及び実用試験法を下記に示す。The 5α-reductase activity inhibition test method, the mouse hair growth promoting effect test method, the human scalp hair growth promoting effect test method, and the practical test method described in the Examples are shown below.
（１）５α−リダクターゼ活性阻害試験法重量３５０〜
４００ｇの雄性ラットより摘出した前立腺（湿重量、約
４ｇ）に３倍量の０．２５ Ｍシュークロースを含む０
．１Ｍ Ｉ（ＥＰＥＳ （ｐＨ７，４）を加え、デフ
ｌコン製ボッター型ホモジナイザーを用いてホモジネー
トした。次いで３、ＯＯＯｒｐｍで１０分間遠心し、沈
渣を１０ｍ１の上記緩衝溶液に懸濁し、再び３．００Ｏ
ｒｐｍで１０分間遠心した。この沈渣に３ｍｆｆの上記
緩衝溶液を加えて再び懸濁し、これを酵素溶液として使
用した。(1) 5α-reductase activity inhibition test method Weight: 350~
The prostate (wet weight, approximately 4 g) extracted from a 400 g male rat contained 0.25 M sucrose, which was 3 times the amount.
．． 1M I (EPES (pH 7,4) was added and homogenized using a Deflcon Botter homogenizer. 3. Centrifuged at OOOrpm for 10 minutes, suspended the precipitate in 10ml of the above buffer solution, and heated again at 3.00O
Centrifuged at rpm for 10 minutes. 3 mff of the above buffer solution was added to this precipitate to suspend it again, and this was used as an enzyme solution.
酵素活性の測定は、［４−”Ｃ）−テストステロン（１
，５ｎｍｏｎ、１．５Ｘ１０５ ｃｐｍ）ＮＡＤＰＨ（
０，５、ｃｒｍｏ ７り 、上記酵素溶液（０，０３ｍ
ｎ ）及び各試料を含む全容０．１ ｍ Ｒの反応溶
液を３７℃で６０分間インキユヘートした（酵素反応は
基質の（４−１４Ｃ）−テストステロンを添加すること
により開始した）。酵素反応はクロロホルム／メタノー
ル（１： ２）のｌｎ 合７８ 媒０、４ ｍ ｌを混
和して停止し、その後２．０００ｒｐｍで３分間遠心分
離した。上清の０．０５ ｍｌをシリカゲルガラスプレ
ートに吸着させ、展開溶媒としてクロロホルム／メタノ
ール／酢酸（９９，２／ Ｏ１６／ ０．２ ）を用い
て室温で１５ｃｍ展開した６標準物質としてテストステ
ロン及びジヒドロテストステロンを同時に展開した。展
開終７後薄層プレートをクロマトスキャナーを用いて走
査し、酵素反応により生じたジヒドロテストステロンの
生成量を測定した。Measurement of enzyme activity was performed using [4-”C)-testosterone (1
,5nmon, 1.5X105 cpm)NADPH(
0.5, crmo 7ri, the above enzyme solution (0.03m
A total volume of 0.1 m R of the reaction solution containing n ) and each sample was incubated at 37° C. for 60 minutes (the enzyme reaction was started by adding the substrate (4-14C)-testosterone). The enzyme reaction was stopped by mixing 0.4 ml of a mixture of chloroform/methanol (1:2), followed by centrifugation at 2.000 rpm for 3 minutes. 0.05 ml of the supernatant was adsorbed onto a silica gel glass plate and developed for 15 cm at room temperature using chloroform/methanol/acetic acid (99,2/O16/0.2) as a developing solvent.6 Testosterone and dihydrotestosterone were used as standard substances. were developed at the same time. After 7 days of development, the thin layer plate was scanned using a chromatography scanner to measure the amount of dihydrotestosterone produced by the enzyme reaction.
（２） マウス毛成長促進効果試験法ｄｄＹ系白色マ
ウス（雄、６週齢、平均重量３５ｇ）の連部よりの背部
皮膚を電気バリカンで刈ったあと、脱毛クリームにより
完全脱毛し、翌日より実施例及び比較例の各試料を被験
部皮膚に毎日１回、−匹当り０．２ｍｌ塗布した。−試
料に対して動物−群１０匹を使用した。(2) Mouse hair growth promotion effect test method After cutting the back skin of a ddY white mouse (male, 6 weeks old, average weight 35 g) from the joint part with electric clippers, complete hair removal with hair removal cream, and the test was carried out from the next day. Each sample of Examples and Comparative Examples was applied to the skin of the test site once a day in an amount of 0.2 ml per animal. -A group of 10 animals were used for the samples.
養毛効果の判定は、下表に示す判定基準による肉眼評定
の評価点と、毛長、毛重量を対照群と比較することによ
り行なった。The hair growth effect was determined by comparing the visual evaluation score, hair length, and hair weight with the control group according to the criteria shown in the table below.
実験開始後１４日目に動物を層殺し判定基準により肉眼
評定し、その評価点を合計し、−匹当りの平均評価を求
めた。さらに、被験部の皮膚を除去し、直径１２ｍｍの
パンチで一定面積の皮膚を打ち抜き乾燥した後、毛の重
量を測定し、その中の２０本の毛の長さについても測定
し、各々の平均値を算出した。On the 14th day after the start of the experiment, the animals were visually evaluated according to the stratification criteria, and the evaluation scores were totaled to determine the average evaluation per animal. Furthermore, the skin of the test area was removed, a certain area of the skin was punched with a punch with a diameter of 12 mm, and after drying, the weight of the hair was measured, and the length of 20 hairs among them was also measured, and the average of each hair was measured. The value was calculated.
養毛効果の評価点の判定基準
（３） ヒト頭髪毛成長促進効果試験法男性型脱毛症
患者である被試験者１０名の頭部の耳の上５ｃｍの位置
の頭髪を左右５ｃｍの位置の頭髪を左右２カ所に於て直
径１ｃｍの円形状に刺毛した被験部位に、実施例または
比較例の試料を左側に毎日朝夕２回、約３ ｍ Ｒ塗布
し、無処置の右側と比較した。効果の判定は、試験開始
後２８日目に、左右の被験部位の毛髪各々２０本ずめて
評価した。Judgment criteria for hair growth effect evaluation score (3) Human hair growth promotion effect test method The hair of 10 test subjects who are patients with androgenetic alopecia was removed from the head at a position 5 cm above the ear, and at a position 5 cm from the left and right. A sample of an example or a comparative example was applied to the left side twice a day in the morning and evening for a radius of about 3 m to the test site where the hair was pricked in a circular shape with a diameter of 1 cm on the left and right sides, and compared with the untreated right side. . The effectiveness was evaluated by evaluating 20 hairs each from the left and right test sites on the 28th day after the start of the test.
判定結果は、被試験者１０名の（Ｂ）／ （Ａ）の平均
値で示した。The judgment results were shown as the average value of (B)/(A) for 10 test subjects.
（４） 実用試験法
男性型脱毛症患者である被試験者２０名の頭部に毎日朝
夕２回、連続６力月間塗布した後の効果を評価した。試
験結果は、育毛効果、脱毛予防効果、ふけ防止効果の各
項に対して、「生毛が剛毛化した或は生毛が増加した」
、［脱毛が少な（なった」、「ふけが少なくなった」と
回答した人数で示した。(4) Practical test method The effect was evaluated after applying the product to the heads of 20 test subjects who were patients with androgenetic alopecia twice a day in the morning and evening for 6 consecutive months. The test results showed that "grown hair became bristly or increased in number" for each of the hair growth effect, hair loss prevention effect, and dandruff prevention effect.
, [Indicated by the number of people who answered that their hair loss has decreased or that their dandruff has decreased.
実施例１〜４、比較例１〜４ （オイリーへアートニッ
ク）
下記の原料組成に於て、第１表に記載のごとく、各種毛
成長促進物質を配合して各々のへアートニックを調製し
、前記の諸試験を実施した。Examples 1 to 4, Comparative Examples 1 to 4 (Artonic for oily hair) Using the following raw material composition, various hair growth promoting substances were blended as shown in Table 1 to prepare each Artonic for oily hair. , conducted the various tests described above.
なお、実施例では前項で述べたカルコン又はカルコン誘
導体１〜■を、比較例としては従来より使われているニ
コチン酸、ニコチン酸メヂル、トウガラシチンキを毛成
長促進物質として配合した。In the Examples, chalcone or chalcone derivatives 1 to 1 described in the previous section were blended, and in comparative examples, conventionally used nicotinic acid, medyl nicotinate, and capsicum tincture were blended as hair growth promoting substances.
ｆｌｌ 組成
（２） 精製法
（Ｂ）成分中、ニコチン酸、ニコチン酸メチルは（Ａ）
成分に、トウガラシチンキ、カルコンス１ヨ力ルコン誘
導体は（Ｃ）成分に溶解し、（Ａ）。fll Composition (2) Purification method (B) Among the components, nicotinic acid and methyl nicotinate are (A)
In the ingredients, capsicum tincture and chalcone derivative are dissolved in ingredient (C), and (A).
（Ｂ）成分を各々均一に溶解した後、（Ａ）成分と（Ｂ
）成分を混合撹拌分散し、次いで容器に充填する。使用
時には内容物を均一に振盪分散して使用する。After each component (B) is uniformly dissolved, the components (A) and (B) are dissolved.
) The ingredients are mixed, stirred and dispersed, and then filled into a container. When using, shake and disperse the contents uniformly.
（３） 特性
各オイリーへアートリックの線試験を実施しまた結果を
第１表に記載した。(3) Characteristics Artric line tests were conducted on each oily and the results are listed in Table 1.
第１表に示すごとく、比較例１〜４は殆ど５αリダクタ
ーゼ活性阻害能を有しなかった。また、比較例２，３．
４は皮膚刺激があり、ヒト皮膚での試験は不可能であっ
た。As shown in Table 1, Comparative Examples 1 to 4 had almost no ability to inhibit 5α-reductase activity. Also, Comparative Examples 2 and 3.
Test No. 4 caused skin irritation, making it impossible to test on human skin.
実施例１〜４の本発明の養毛化粧料は線試験に総てに於
て明らかに良好な結果を示した。The hair nourishing cosmetics of Examples 1 to 4 of the present invention showed clearly good results in all line tests.
尚、実施例１〜４はヒト皮膚での線試験に於て皮膚刺激
は生しなかった。In Examples 1 to 4, no skin irritation occurred in the line test on human skin.
実施例５〜８、比較例５〜８ （ヘアークリーム）実施
例１と同様にして各々のへアークリームを調製して線試
験を実施し、その結果を第１表に記ｎ＋ Ｍｉ成
（２） 調製法
（Ｂ）成分中、ニコチン酸、ニコチン酸メチルは（Ａ）
成分中に、トウガラシチンキ、カルコン又はカルコン誘
導体は（Ｃ）成分に溶解し、（Ａ）（Ｃ）成分を各々温
度８０ ’ｃに加熱溶解したちのを混合した。次で撹拌
しつつ冷却して温度５０°Ｃになったところで（ｎ成分
を加え、更に温度３０°Ｃまで撹拌を続けて各ヘアーク
リームを調製した。Examples 5 to 8, Comparative Examples 5 to 8 (Hair cream) Each hair cream was prepared in the same manner as in Example 1 and a line test was conducted.The results are shown in Table 1. ) In the preparation method (B), nicotinic acid and methyl nicotinate are (A)
Among the ingredients, capsicum tincture, chalcone, or a chalcone derivative was dissolved in component (C), and components (A) and (C) were each heated and dissolved at a temperature of 80'C and then mixed. Next, the mixture was cooled while stirring, and when the temperature reached 50°C, component (n) was added, and stirring was continued until the temperature reached 30°C to prepare each hair cream.
（３） 特性
第１表に示すごとく、本発明の皮膚化粧料である実施例
５〜８の養毛化粧料は、比較例５〜８と比較して高い５
α−リダクターゼ活性阻害率を示〔発明の効果〕
以上記載のごとく、本発明は、５α−リダクターゼ活性
の阻害能を有し、育毛、脱毛予防及びふけ防止等の効果
に優れると共に、皮膚刺激性の低い養毛化粧料を提供す
ることは明らがである。(3) Properties As shown in Table 1, the hair nourishing cosmetics of Examples 5 to 8, which are skin cosmetics of the present invention, have a higher
[Effects of the Invention] As described above, the present invention has the ability to inhibit 5α-reductase activity, and has excellent effects such as hair growth, hair loss prevention, and dandruff prevention. It is obvious that the present invention provides a hair-nourishing cosmetic with low hair growth.
Claims (1)
基、メトキシ基、エトキシ基、イソプロピル基を示す。 ） で示されるカルコン又はカルコン誘導体の１種または２
種以上を含有してなる養毛化粧料。[Claims] The following general formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) (In the formula, R_1 to R_7 are hydrogen atoms, hydroxyl groups, methyl groups, methoxy groups, ethoxy or isopropyl group.) One or two of the chalcone or chalcone derivatives represented by
A hair nourishing cosmetic containing seeds or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29532288A JPH02142717A (en) | 1988-11-22 | 1988-11-22 | Hair nouring cosmetic |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29532288A JPH02142717A (en) | 1988-11-22 | 1988-11-22 | Hair nouring cosmetic |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02142717A true JPH02142717A (en) | 1990-05-31 |
Family
ID=17819116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29532288A Pending JPH02142717A (en) | 1988-11-22 | 1988-11-22 | Hair nouring cosmetic |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02142717A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07258042A (en) * | 1994-03-15 | 1995-10-09 | Sanwa Shiyouyaku Kk | Novel hair restoration and growth stimulant |
| WO2003029176A1 (en) * | 2001-10-03 | 2003-04-10 | Cancer Research Technology Limited | 4-(c2-6alkoxy)-substituted chalcones as therapeutic agents |
| US6787672B2 (en) | 2000-03-27 | 2004-09-07 | Cancer Research Technology Limited | Substituted chalcones as therapeutic compounds |
| WO2005027866A1 (en) * | 2003-09-12 | 2005-03-31 | Beiersdorf Ag | Use of licocalchone a or of an extract containing licocalchone a from radix glycyrrhizae inflatae against skin aging |
| JP2006347915A (en) * | 2005-06-14 | 2006-12-28 | Maruzen Pharmaceut Co Ltd | Hair tonic, antiandrogen agent and hair cosmetic |
| JP2009534334A (en) * | 2006-04-21 | 2009-09-24 | ディーエスエム アイピー アセッツ ビー．ブイ． | Use of opioid receptor antagonists |
| US7598294B2 (en) | 2001-10-03 | 2009-10-06 | Spear Therapeutics Limited | 3,4-methylenedioxy-substituted chalcones as therapeutic agents |
| US8143218B2 (en) | 1998-07-30 | 2012-03-27 | Regenerx Biopharmaceuticals, Inc. | Treatment of skin, and wound repair, with thymosin beta 4 |
| JP2012121913A (en) * | 2012-03-05 | 2012-06-28 | Maruzen Pharmaceut Co Ltd | Skin cosmetic and hair cosmetic |
| WO2017131954A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | Personal care composition comprising a hair restorative blend |
| WO2017131956A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | A method for treating the appearance of thinning hair |
| WO2017131957A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | A method for treating the appearance of thinning hair |
| WO2017131955A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | Personal care composition comprising a hair restorative blend |
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-
1988
- 1988-11-22 JP JP29532288A patent/JPH02142717A/en active Pending
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07258042A (en) * | 1994-03-15 | 1995-10-09 | Sanwa Shiyouyaku Kk | Novel hair restoration and growth stimulant |
| US8143218B2 (en) | 1998-07-30 | 2012-03-27 | Regenerx Biopharmaceuticals, Inc. | Treatment of skin, and wound repair, with thymosin beta 4 |
| US6787672B2 (en) | 2000-03-27 | 2004-09-07 | Cancer Research Technology Limited | Substituted chalcones as therapeutic compounds |
| WO2003029176A1 (en) * | 2001-10-03 | 2003-04-10 | Cancer Research Technology Limited | 4-(c2-6alkoxy)-substituted chalcones as therapeutic agents |
| US7112698B2 (en) | 2001-10-03 | 2006-09-26 | Spear Therapeutics Limited | 4-(c2-6alkoxy)-substituted chalcones as therapeutic agents |
| US7598294B2 (en) | 2001-10-03 | 2009-10-06 | Spear Therapeutics Limited | 3,4-methylenedioxy-substituted chalcones as therapeutic agents |
| WO2005027866A1 (en) * | 2003-09-12 | 2005-03-31 | Beiersdorf Ag | Use of licocalchone a or of an extract containing licocalchone a from radix glycyrrhizae inflatae against skin aging |
| JP2006347915A (en) * | 2005-06-14 | 2006-12-28 | Maruzen Pharmaceut Co Ltd | Hair tonic, antiandrogen agent and hair cosmetic |
| JP2009534334A (en) * | 2006-04-21 | 2009-09-24 | ディーエスエム アイピー アセッツ ビー．ブイ． | Use of opioid receptor antagonists |
| JP2012121913A (en) * | 2012-03-05 | 2012-06-28 | Maruzen Pharmaceut Co Ltd | Skin cosmetic and hair cosmetic |
| WO2017131954A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | Personal care composition comprising a hair restorative blend |
| WO2017131956A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | A method for treating the appearance of thinning hair |
| WO2017131957A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | A method for treating the appearance of thinning hair |
| WO2017131955A1 (en) * | 2016-01-27 | 2017-08-03 | Elc Management Llc | Personal care composition comprising a hair restorative blend |
| KR20180097781A (en) * | 2016-01-27 | 2018-08-31 | 이엘씨 매니지먼트 엘엘씨 | How to handle the appearance of tapered hair |
| KR20180099898A (en) * | 2016-01-27 | 2018-09-05 | 이엘씨 매니지먼트 엘엘씨 | A personal care composition comprising a hair recovery blend |
| CN108883042A (en) * | 2016-01-27 | 2018-11-23 | Elc 管理有限责任公司 | The method for handling sparse hair appearance |
| CN108883041A (en) * | 2016-01-27 | 2018-11-23 | Elc 管理有限责任公司 | The personal care composition of blend is repaired comprising hair |
| CN108883042B (en) * | 2016-01-27 | 2021-10-29 | Elc 管理有限责任公司 | Method of treating the appearance of open hair |
| US10029843B2 (en) | 2016-03-07 | 2018-07-24 | Elc Management Llc | False eyelash dispenser |
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