JPS5953417A - Testosterone-5alpha-reductase inhibitor - Google Patents
Testosterone-5alpha-reductase inhibitorInfo
- Publication number
- JPS5953417A JPS5953417A JP16427582A JP16427582A JPS5953417A JP S5953417 A JPS5953417 A JP S5953417A JP 16427582 A JP16427582 A JP 16427582A JP 16427582 A JP16427582 A JP 16427582A JP S5953417 A JPS5953417 A JP S5953417A
- Authority
- JP
- Japan
- Prior art keywords
- testosterone
- 5alpha
- formula
- decen
- bicyclo
- 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.)
- Granted
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
- A61K8/33—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
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、新規なるテストステロン−5α−しダクター
ゼ阻害剤に関するものである。男性型の禿頭、粗毛症、
尋常性能jM、脂漏などの生理学1の徴候は、代謝系に
男性ホルモンが過剰にi f【1f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、G 、fl、!、皮脂腺をはしめい
くつかの器官において男性ホルモン活性の本体は、5α
−ジヒドロテストス〜ア■」ンでアリ、これは標的器官
においてテストステロンがデス1ステロンー5α−レダ
クターゼ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。その゛ため、男性ホルモン1テリ激
の増大に起因する男性型の禿頭・粗毛症、尋常性座癒、
脂漏などの徴候は、テストステロン−5α−レダクター
ゼを阻害することにより低減あるいは防11−すること
ができると考えられ、テストステロン−5α−しダクタ
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。例えば黄体ホルモンプロゲステロ
ンはテストステロン−5α−レダクターゼを大きく阻害
することが周知であるが、その反面、プロゲステロン自
身の持ツ女性ポルモン作用が発現し、乳房の肥大、澤丸
委縮、精力減退なとの好ましくない作用が現われてくる
。また、乍までに新規に合成された阻害剤は、ステロイ
1.’ jJI造あるいはステロイド類似構造を持って
おり、やは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。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel testosterone-5α-ductase inhibitor. Male pattern baldness, hair loss,
It is known that symptoms of Physiology 1, such as normal performance jM and seborrhea, are based on increased stimulation of androgens caused by excessive production of androgens in the metabolic system. Recently, G, fl,! , the main body of male hormone activity in several organs including the sebaceous glands is 5α
It is well known that dihydrotestosterone is produced by the reduction of testosterone by des1sterone-5α-reductase in the target organ. As a result, male-pattern baldness and coarse hair, acne vulgaris,
It is thought that symptoms such as seborrhea can be reduced or prevented by inhibiting testosterone-5α-reductase, and several inhibitors have been discovered that specifically inhibit testosterone-5α-reductase. is,
It has also been synthesized. For example, it is well known that progesterone, a progesterone, greatly inhibits testosterone-5α-reductase, but on the other hand, progesterone itself exhibits its own female pormon effect, which causes undesirable effects such as enlargement of the breasts, atrophy of the Sawa's circle, and decreased energy. Effects that were previously absent will appear. In addition, the newly synthesized inhibitors are steroid 1. It has a JI structure or a steroid-like structure, and it also has the disadvantage of having some undesirable hormone-like effects.
(以下全白)
本発明者らは、ホルモン様作用を全く持たないテストス
テロン−5α−レダクターゼ阻害剤について鋭意研究を
重ねた結果、5.6−シメチルー8 ” イア フoベ
ニル−ビンクロ(4,4,0:IV’セン−1−オン−
3がテストステロン−5α−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致った。即ち、
本発明は式(1)で表わされる5、6−シメチルー8−
インプロペニル−ビシクロ(4,4,0)デセン−1−
オン−3からなるテストステロン−5α−レダクターゼ
阻害剤である。(Hereinafter referred to as "all white") As a result of extensive research into a testosterone-5α-reductase inhibitor that has no hormone-like effects, the present inventors discovered that 5,6-cymethyl-8'' iafbenyl-binculo (4,4 ,0:IV'sen-1-one-
The present invention was completed by discovering that 3 inhibits testosterone-5α-reductase. That is, the present invention provides 5,6-cymethyl-8- represented by formula (1).
Impropenyl-bicyclo(4,4,0)decene-1-
It is a testosterone-5α-reductase inhibitor consisting of 1-3.
(以下余白)
5.6−シメチルー8−インプロペニル−ビシクロ(4
,4,0)デセン−1−オン−3はグレープフルーツオ
イル等に含有されているセスキテルペンケトンであって
、ホルモン作用は一切持たず、また他の好ましくない副
作用も有していない。(Left below) 5.6-dimethyl-8-impropenyl-bicyclo(4
, 4, 0) Decen-1-one-3 is a sesquiterpene ketone contained in grapefruit oil and the like, and has no hormonal effects or other undesirable side effects.
従って、本発明の5.6−シメチルー8−インプロペニ
ル−ビシクロ(4,4’、o)デセン−1−オン−3を
テストステロン−5α−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
すぐれた利点を有している。Therefore, even when the 5,6-dimethyl-8-impropenyl-bicyclo(4,4',o)decen-1-one-3 of the present invention is used as a testosterone-5α-reductase inhibitor, it does not exhibit any hormone-like effects. Moreover, it has the excellent advantage of being safe even when used externally for a long period of time.
次に、本発明の5〜6−ジメテルー8−イソプロペ1ル
ービシクロ(4,4,0)デセン−1−オン−3のテス
トステロン−5α−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。Next, an experimental example demonstrating the testosterone-5α-reductase inhibitory effect of 5-6-dimethe-8-isoprope-1-rubicyclo(4,4,0)decen-1-one-3 of the present invention will be specifically shown below. .
(以下余白)
高安らの方法(S、 Takayasu 、 K、 A
dachi 、ザ・ジャー9
ナル拳オブ傘クリニカル・エンドクルノロシー崇エント
メタボリズム(J、 01in 、 Endocrin
ol 、Metaへ、)。(Left below) Takayasu's method (S, Takayasu, K, A
dachi, The Jar 9 Naruken of Umbrella Clinical Endocrinology Entometabolism (J, 01in, Endocrin
ol, to Meta,).
第ヌ巻、第1098−1101項、1992年〕に従い
、人毛根を用い、テストステロンが5α−ジヒドロテス
トステロンに還元されるVi′rを測定し、5.6−シ
メチルー8−イソプロペミル−ビシクロ(4,4,0)
デセン−1−オン−3によるテストステロン−5α−レ
ダクターゼ阻害作用を検討し、表1に示した。Vol. 1, No. 1098-1101, 1992], using human hair roots, the Vi′r at which testosterone is reduced to 5α-dihydrotestosterone was measured, and 5,6-dimethyl-8-isopropemyl-bicyclo(4, 4,0)
The inhibitory effect of decen-1-one-3 on testosterone-5α-reductase was investigated and is shown in Table 1.
表1 人毛根テストステロンー5α−レダクタ−(以下
余白)
また、ハムスターの皮脂腺を用いる高安らの方法〔高安
進、板見 智、西日本皮膚利、第ぐ巻、第1.215
−121.7頁1981年〕に基づいて、皮脂腺のテス
トステロン−5α−レダクターゼを阻害する5、6−シ
メチルー8−インプロペペルービシクロ〔4,4,O)
デセン−1−オン−3の効果を表2に示した。BI4害
率0算出方法は表−1と同様である。Table 1 Human hair root testosterone-5α-reductor (blank below) Also, Takayasu's method using hamster sebaceous glands [Susumu Takayasu, Satoshi Itami, Nishinippon Dermatology, Vol. 2, No. 1.215
-121.7, 1981], 5,6-cymethyl-8-impropeperubicyclo[4,4,O] inhibits testosterone-5α-reductase in the sebaceous gland.
Table 2 shows the effects of decen-1-one-3. The method for calculating BI4 harm rate 0 is the same as in Table-1.
表2 ハムスター皮脂腺テストステロン−5α−前記表
1および表2において、人毛根・ハムスター皮脂腺にお
ける5、6−シメチルー8−インプロペヌル−ビシクロ
(4,4,0)デセン−1−オン−3のテストステロン
−5α−レダクターゼ阻害作用が明らかに認められた。Table 2 Hamster sebaceous gland Testosterone-5α - In Tables 1 and 2 above, Testosterone-5α of 5,6-dimethyl-8-impropenul-bicyclo(4,4,0)decen-1-one-3 in human hair roots and hamster sebaceous glands - Reductase inhibitory effect was clearly observed.
このように、5.6−シメチルー8−インプロペペルー
ビシクロ(4,4,0)デセン−1−オン−3はテスト
ステロン−5α−レダクターゼ阻害作用ヲ有するのみな
らず、ホルモン様作用は−uJもだ1″安全性も高いと
いうすぐれた特徴を有してOZ)。Thus, 5,6-cymethyl-8-impropeperubicyclo(4,4,0)decen-1-one-3 not only has an inhibitory effect on testosterone-5α-reductase, but also has a hormone-like effect on -uJ. It has the excellent feature of being highly safe (OZ).
特許出願人 株式会社 資 生 堂Patent applicant: Shiseido Co., Ltd.
Claims (1)
−インプロペニル−ピンクo(4,4,0)7’セン−
1−オン−3からなるテストステロン−5α−レダクタ
ーゼ阻害剤。 (以下余白)(1) 5,6-cymethyl-8 represented by formula (I)
-impropenyl-pink o(4,4,0)7'sen-
Testosterone-5α-reductase inhibitor consisting of 1-one-3. (Margin below)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16427582A JPS5953417A (en) | 1982-09-21 | 1982-09-21 | Testosterone-5alpha-reductase inhibitor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16427582A JPS5953417A (en) | 1982-09-21 | 1982-09-21 | Testosterone-5alpha-reductase inhibitor |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5953417A true JPS5953417A (en) | 1984-03-28 |
JPH0380769B2 JPH0380769B2 (en) | 1991-12-26 |
Family
ID=15789986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16427582A Granted JPS5953417A (en) | 1982-09-21 | 1982-09-21 | Testosterone-5alpha-reductase inhibitor |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5953417A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4937237A (en) * | 1988-12-23 | 1990-06-26 | Smithkline Beckman Corporation | Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase |
US4970205A (en) * | 1988-12-23 | 1990-11-13 | Smithkline Beecham Corporation | Sulfonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase |
EP0467660A2 (en) * | 1990-07-20 | 1992-01-22 | Yutaka Miyauchi | Use of d-limonenes as testosterone-5-alpha-reductase inhibitor and as hair grower |
-
1982
- 1982-09-21 JP JP16427582A patent/JPS5953417A/en active Granted
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4937237A (en) * | 1988-12-23 | 1990-06-26 | Smithkline Beckman Corporation | Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase |
US4970205A (en) * | 1988-12-23 | 1990-11-13 | Smithkline Beecham Corporation | Sulfonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase |
EP0467660A2 (en) * | 1990-07-20 | 1992-01-22 | Yutaka Miyauchi | Use of d-limonenes as testosterone-5-alpha-reductase inhibitor and as hair grower |
EP0467660A3 (en) * | 1990-07-20 | 1992-07-22 | Yutaka Miyauchi | Use of d-limonenes as testosterone-5-alpha-reductase inhibitor and as hair grower |
Also Published As
Publication number | Publication date |
---|---|
JPH0380769B2 (en) | 1991-12-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0641355A1 (en) | Steroid sulphatase inhibitors | |
JPH0517365A (en) | Testosterone 5alpha-reductase inhibitor | |
JPS6284021A (en) | Testosterone-5alpha-reductase inhibitor | |
JPS5953417A (en) | Testosterone-5alpha-reductase inhibitor | |
JPH0469620B2 (en) | ||
JP4628840B2 (en) | Testosterone-5α-reductase inhibitor | |
JPS644758B2 (en) | ||
RU95110751A (en) | NEW 17β-SUBSTITUTED DERIVATIVES OF 4-AZAANDROSTANE, PHARMACEUTICAL COMPOSITIONS CONTAINING THEREOF AND METHOD OF THEIR PREPARING | |
JP2000229857A (en) | Testosterone-5-alpha-reductase inhibitor | |
Rasmusson | Chemical control of androgen action | |
JPS5953418A (en) | Testosterone-5-alpha-reductase inhibitor | |
Korduba et al. | SCH 10595, an effective dopamine-β-hydroxylase inhibitor and a hypotensive agent | |
JP2753607B2 (en) | Testosterone 5α-reductase inhibitor | |
EP2101798B1 (en) | Topical treatment of acne with extracts of glycyrrhiza, foeniculum and atriplex, combined with minerals | |
JPS5953419A (en) | Testosterone-5alpha-reductase inhibitor | |
JPH02193920A (en) | 5alpha-reductase inhibitor | |
JPH0730001B2 (en) | Novel cinnamic acid amide derivative and pharmaceuticals containing the same | |
JPH0753334A (en) | Hair restoring and growing cosmetic | |
JPH013125A (en) | Testosterone 5α-reductase inhibitor | |
Kowalewski | Catabolic effect of dihydrotachysterol and anabolic action of 17-ethyl-19-nortestosterone on the uptake of radiosulphur in a healing fractured bone of the rat | |
JPS61148111A (en) | Trichogenic promoter | |
WO2003082233A1 (en) | Allyl-phenol compounds in androgenic disorders | |
JP4803698B2 (en) | Anti-aging agent, estrogenic agent, anti-androgen agent, hair restorer, testosterone 5α-reductase inhibitor, skin cosmetic and hair cosmetic | |
JPH11246413A (en) | Steroid 5-alpha-reductase ii-type-specific inhibitor | |
CA1112178A (en) | Quinonic or phenolic compounds as topical compositions |