JPS6388121A - Testosterone 5alpha-reductase inhibitor - Google Patents
Testosterone 5alpha-reductase inhibitorInfo
- Publication number
- JPS6388121A JPS6388121A JP23397386A JP23397386A JPS6388121A JP S6388121 A JPS6388121 A JP S6388121A JP 23397386 A JP23397386 A JP 23397386A JP 23397386 A JP23397386 A JP 23397386A JP S6388121 A JPS6388121 A JP S6388121A
- Authority
- JP
- Japan
- Prior art keywords
- musizin
- hexane
- mucidin
- rumex japonicus
- testosterone
- 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
- 102000001779 3-oxo-5-alpha-steroid 4-dehydrogenase Human genes 0.000 title claims description 8
- 108010029908 3-oxo-5-alpha-steroid 4-dehydrogenase Proteins 0.000 title claims description 8
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 title claims description 5
- 239000002677 5-alpha reductase inhibitor Substances 0.000 title claims description 5
- JSCQSBGXKRTPHZ-UHFFFAOYSA-N Mucidin Natural products COC=C(C(=O)OC)C(C)=CC=CC1=CC=CC=C1 JSCQSBGXKRTPHZ-UHFFFAOYSA-N 0.000 claims description 17
- JSCQSBGXKRTPHZ-WMSPMLHYSA-N Strobilurin A Natural products COC=C(/C(=C/C=C/c1ccccc1)/C)C(=O)OC JSCQSBGXKRTPHZ-WMSPMLHYSA-N 0.000 claims description 17
- JSCQSBGXKRTPHZ-SYKZHUKTSA-N mucidin Chemical compound CO\C=C(\C(=O)OC)/C(/C)=C\C=C\C1=CC=CC=C1 JSCQSBGXKRTPHZ-SYKZHUKTSA-N 0.000 claims description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003054 hormonal effect Effects 0.000 abstract description 6
- 244000189123 Rumex japonicus Species 0.000 abstract description 5
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 4
- 235000005247 Rumex japonicus Nutrition 0.000 abstract description 4
- 206010000496 acne Diseases 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000003208 petroleum Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- DMLHPCALHMPJHS-UHFFFAOYSA-N Nepodin Chemical compound C1=CC=C(O)C2=C(O)C(C(=O)C)=C(C)C=C21 DMLHPCALHMPJHS-UHFFFAOYSA-N 0.000 abstract 8
- 239000004480 active ingredient Substances 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000001256 tonic effect Effects 0.000 abstract 1
- 102000004316 Oxidoreductases Human genes 0.000 description 8
- 108090000854 Oxidoreductases Proteins 0.000 description 8
- 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
- 239000003112 inhibitor Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 210000001732 sebaceous gland Anatomy 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960003604 testosterone Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229940123934 Reductase inhibitor Drugs 0.000 description 2
- 206010039792 Seborrhoea Diseases 0.000 description 2
- 206010068168 androgenetic alopecia Diseases 0.000 description 2
- -1 butanol Chemical class 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 2
- 241000219050 Polygonaceae Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 229960003473 androstanolone Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229910001751 gemstone Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
- 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
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (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、新規にして、かつ安全なるテストステロン−
50−レダクターゼ阻害剤に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention provides a novel and safe method for producing testosterone.
50-reductase inhibitors.
[従来の技術]
男性型の禿頭、粗毛症、尋常性座痔、脂漏などの生理学
上の徴候は、代謝系に男性ホルモンが過剰に蓄積される
ことに起因する男性ホルモン刺激の増大に基づいている
ことが知られている。また最近、毛根、皮脂腺をはじめ
いくつかの器官において男性ホルモン活性の本体は、5
α−ジヒドロテストステロン(以下、5α−D HTと
略す。)であり、これは標的器官においてテストステロ
ンがテストステロン−5α−レダクターゼ(以下、レダ
クターゼと略す。)により還元されることによって生成
することが周知になっている。[Prior Art] Physiological symptoms such as male-pattern baldness, hair loss, acne vulgaris, and seborrhea are based on increased stimulation of androgenic hormones caused by excessive accumulation of male hormones in the metabolic system. It is known that Recently, it has been discovered that the main body of male hormone activity in several organs including hair roots and sebaceous glands is 5.
α-dihydrotestosterone (hereinafter abbreviated as 5α-D HT) is known to be produced when testosterone is reduced by testosterone-5α-reductase (hereinafter abbreviated as reductase) in target organs. It has become.
そのため、男性ホルモン刺激の増大に起因する男性型の
禿頭、粗毛症、尋常性座疹、脂漏などの徴候は、レダク
ターゼを阻害することにより低減あるいは防止すること
ができると考えられ、レダクターゼを特異的に阻害する
いくつかの阻害剤が見出され、また合成されてきた。し
かし、今までに新規に合成された阻害剤は、ステロイド
構造あるいはステロイド類似構造を持っており、好まし
くないホルモン様作用を多少なりとも有しているという
欠点があった。Therefore, it is thought that symptoms such as male-pattern baldness, coarse hair, acne vulgaris, and seborrhea caused by increased stimulation of androgens can be reduced or prevented by inhibiting reductase. Several inhibitors have been discovered and synthesized that inhibit However, the newly synthesized inhibitors to date have a steroid structure or a steroid-like structure, and have the drawback of having some degree of undesirable hormone-like action.
[発明が解決しようとする問題点]
本発明者らは、上記事情に鑑み、ホルモン様作用を全く
持たず、安全性にも優れた天然のレダクターゼ阻害剤に
ついて鋭意研究を重ねた結束、ムシジンレダクターゼを
阻害することを見出し本発明を完成するに至った。[Problems to be Solved by the Invention] In view of the above circumstances, the present inventors have conducted intensive research on natural reductase inhibitors that have no hormone-like effects and are excellent in safety. The present inventors have discovered that reductase can be inhibited and have completed the present invention.
[問題点を解決するための手段]
すなわち、本発明は、ムシジンからなるテストステロン
−5α−レダクターゼ阻害剤である。[Means for Solving the Problems] That is, the present invention is a testosterone-5α-reductase inhibitor consisting of mucidin.
以下、本発明の措成について詳述する。Hereinafter, the implementation of the present invention will be explained in detail.
本発明に用いられるムシジンは、例えばタデ科の多年生
草本で、学名は rtumex japonicus
H。Mucidin used in the present invention is, for example, a perennial herb of the Polygonaceae family, and its scientific name is Rtumex japonicus.
H.
utt、 といい、日本各地の湿地に自生する植物ギ
シギシから得られる。その根は漢名を羊蹄といい、水虫
などの皮膚病や、大賀の代用として緩下剤に用いること
もある生薬である。その成分の一つにムシジンも含まれ
ている。It is called utt, and it is obtained from the plant Gishigishi, which grows naturally in wetlands throughout Japan. The root's Chinese name is Yotei, and it is a herbal medicine that is sometimes used for skin diseases such as athlete's foot, and as a laxative as a substitute for Oga. Mucidin is also included as one of its components.
ムシジンの構造は下記に示す通りである。The structure of mucidin is shown below.
ムシジンは上記のように天然界にも存在するが、当然の
ことながら、本発明に用いるムシジンは合成のものでも
よい。Although mucidin exists in nature as described above, it goes without saying that the mucidin used in the present invention may be synthetic.
天然物から抽出して得る方法は、特に限定されないが以
下のような方法が好ましい。The method of extraction from natural products is not particularly limited, but the following methods are preferred.
乾燥したギシギシ(Rumex japonicus
Houtt、)の根部をジクロロメタンで加温抽出し、
抽出液からジクロロメタンを留去して得た粗結晶物質を
石油エーテルから再結晶して黄色針試結晶が得られる。Dry Rumex japonicus
Houtt,) was heated and extracted with dichloromethane,
The crude crystalline material obtained by distilling off dichloromethane from the extract is recrystallized from petroleum ether to obtain yellow needle test crystals.
この結晶は、ムシジンを90%以上含み、再結晶を繰返
すことによってさらに純度は向上する。This crystal contains 90% or more of mucidin, and the purity can be further improved by repeating recrystallization.
本旨を、テストステロン−5α−レダクターゼ阻害剤と
して用いてもよいが、以下のような方法で得られる抽出
液の形で使用することもできる。The substance may be used as a testosterone-5α-reductase inhibitor, but it can also be used in the form of an extract obtained by the following method.
乾燥したギシギシの相部をヘキサンで加温抽出し、抽出
液からヘキサンを完全に留去してから、得られたヘキサ
ン可溶部を、目的に合わせて各種の溶媒、例えば、メタ
ノール、エタノール、ブタノール等の低級アルコール、
エーテル、酢酸エチル、アセトン、クロロホルム、ベン
ゼン等の有機溶媒、又はトリエチルシトレート等の香料
調製剤やトリ(カプリル・カプリン酸)グリセリン、ス
クアラン、トリオクタン酸グリセリル等の化粧品原石で
加温抽出した溶液を、テストステロン−5α−レダクタ
ーゼ阻害剤として用いる。もちろんヘキサン溶液のまま
でも使用できる。これらの溶液にもムシジンが含まれて
いる。The dried squeaky phase is extracted under heating with hexane, the hexane is completely distilled off from the extract, and the resulting hexane-soluble portion is mixed with various solvents, such as methanol, ethanol, etc., depending on the purpose. lower alcohols such as butanol,
A solution extracted by heating with an organic solvent such as ether, ethyl acetate, acetone, chloroform, benzene, etc., or a fragrance preparation agent such as triethyl citrate, or a cosmetic gemstone such as tri(caprylic/capric) glycerin, squalane, glyceryl trioctanoate, etc. , used as a testosterone-5α-reductase inhibitor. Of course, it can also be used as a hexane solution. These solutions also contain mucidin.
ムシジンは、ホルモン様作用は一切持たず、また、他の
好ましくないIII作用も有していない。従って、本発
明のムシジンをレダクターゼ阻害剤として使用しても、
ホルモン様作用は全く持たず、しかも長期にわたり継続
的に外用しても、安全性には問題がないという優れた利
点を有している。Mucidin does not have any hormone-like effects or other undesirable III effects. Therefore, even if the mucidin of the present invention is used as a reductase inhibitor,
It has the excellent advantage of not having any hormone-like effects and is safe even when used externally for a long period of time.
[実施例]
次に、本発明のムシジンのレダクターゼ阻害作用を実証
する実験例を以下に具体的に示す。[Example] Next, an experimental example to demonstrate the reductase inhibitory effect of mucidin of the present invention will be specifically shown below.
高安らの方法(S 、 Takayasu、 K 、
Adachi、 J 。Takayasu's method (S, Takayasu, K,
Adachi, J.
Cl1n、Endocrinol、Metab、、 3
4.1098−1101(1972))に従い、大毛根
を用い、テストステロンが5α−D 11 Tに還元さ
れる量を測定し、ムシジンによるレダクターゼ阻害作用
を検討し、表1に示した。Cl1n, Endocrinol, Metab, 3
4.1098-1101 (1972)), the amount of testosterone reduced to 5α-D 11 T was measured using large hair roots, and the reductase inhibitory effect of mucidin was investigated, and the results are shown in Table 1.
表1 人=lB+ffテストステロン−5o−レダクタ
ーゼ阻害剤(%)
阻害剤を添加した時の
5α−D HT生成量
阻害¥(%)=1− X100
阻害剤を添加しない時の
5α−D HT生成量
::: 3X10 .3X10 重量%また、ハム
スターの皮脂線を用いる高安らの方法〔高安 進、板見
智、西日本皮膚科、 43.1215−1217 (
1981) )に舵づいて、皮脂綿のレダクターゼを阻
害するムシジンの効果を表2に示した。Table 1 Human = 1B + ff Testosterone-5o-reductase inhibitor (%) 5α-D HT production inhibition when inhibitor is added (%) = 1-X100
Amount of 5α-D HT produced when no inhibitor is added::: 3X10. 3X10% by weight Also, Takayasu's method using hamster sebaceous glands [Susumu Takayasu, Satoshi Itami, Nishinippon Dermatology, 43.1215-1217 (
Table 2 shows the effect of mucidin on inhibiting sebum reductase, based on the results of 1981).
表2 ハムスター皮脂腺テストステロンー5α−レダク
ターゼ阻害率(%)
*1 エタノール液
*2 トリオクタン酸グリセリル
*33X10 .3X10−3重量%
前記表1および表2において、人毛根、ハムスター皮脂
線におけるギシギシ抽出液およびムシジンのレダクター
ゼ阻害作用が明白に認められた。Table 2 Hamster sebaceous gland testosterone-5α-reductase inhibition rate (%) *1 Ethanol solution *2 Glyceryl trioctanoate *33X10. 3X10-3% by weight In Tables 1 and 2 above, the reductase inhibitory effects of the Gishigish extract and mucidin on human hair roots and hamster sebaceous glands were clearly observed.
なお、本発明に係るムシジンの毒性は低く、−般的な皮
膚−時刺戟試験のスコアはワセリンと同程度かやや高く
、トリグリセライド系の油脂の約1/2程度である。The toxicity of mucidin according to the present invention is low, and its score in a general skin irritation test is comparable to or slightly higher than that of vaseline, and about 1/2 that of triglyceride oils and fats.
[発明の効果]
このように、ギシギシ抽出液およびムシジンはテストス
テロン−5α−レダクターゼ阻害作用を有する安全性の
高い物質であり、長期かつ継続的に外用できるという傷
めて有用な特徴を有しているため、養毛料、尋常性座疹
治療剤などに応用することができよう。[Effects of the invention] As described above, Kishigish extract and Mucidin are highly safe substances that have a testosterone-5α-reductase inhibitory effect, and have the advantageous feature of being able to be used externally for a long period of time and continuously. Therefore, it could be applied to hair nourishing agents, acne vulgaris treatment agents, etc.
Claims (1)
ターゼ阻害剤。(1) Testosterone-5α-reductase inhibitor consisting of mucidin.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23397386A JPS6388121A (en) | 1986-10-01 | 1986-10-01 | Testosterone 5alpha-reductase inhibitor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23397386A JPS6388121A (en) | 1986-10-01 | 1986-10-01 | Testosterone 5alpha-reductase inhibitor |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6388121A true JPS6388121A (en) | 1988-04-19 |
Family
ID=16963539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23397386A Pending JPS6388121A (en) | 1986-10-01 | 1986-10-01 | Testosterone 5alpha-reductase inhibitor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6388121A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020032296A1 (en) * | 2018-08-10 | 2020-02-13 | 탑월드(주) | Functional composition |
-
1986
- 1986-10-01 JP JP23397386A patent/JPS6388121A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020032296A1 (en) * | 2018-08-10 | 2020-02-13 | 탑월드(주) | Functional composition |
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