Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-03-08
1996-06-25
Haley, Jacqueline
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548492, 548493, A61K 3140, C07D20912
Patent
active
055300197
DESCRIPTION:
BRIEF SUMMARY
This application is a National Stage application of PCT/JP94/00406, filed Mar. 14, 1994, which published as WO94/22821 on Oct. 13, 1994.
TECHNICAL FIELD
The present invention relates to novel indole derivatives and pharmaceutically acceptable salts thereof. More particularly, it relates to novel indole derivatives and pharmaceutically acceptable salts thereof, which have pharmacological activities such as inhibitory activity on testosterone 5.alpha.-reductase, to a process for the preparation thereof, to a pharmaceutical composition comprising the same, and to a use of the same as a medicament.
BACKGROUND ART
It has hitherto been known that indole derivatives are effective for testosterone 5.alpha.-reductase-mediated diseases. However, a testosterone 5.alpha.-reductase inhibitor with stronger effect has been demanded.
DISCLOSURE OF THE INVENTION
Accordingly, one object of the present invention is to provide novel indole derivatives and pharmaceutically acceptable salts thereof, which are useful as a testosterone 5.alpha.-reductase inhibitor.
Another object of the present invention is to provide a process for the preparation of said indole derivatives or salts thereof.
A further object of the present invention is to provide a pharmaceutical composition comprising, as an active ingredient, said indole derivative or a pharmaceutically acceptable salt thereof.
A still further object of the present invention is to provide use of said indole derivatives or pharmaceutically acceptable salts thereof as a medicament such as a testosterone 5.alpha.-reductase inhibitor useful for treating and/or preventing testosterone 5.alpha.-reductase-mediated diseases such as alopecia, acnes and prostatism in human being or animals.
Indole derivatives of the present invention are novel and can be represented by the formula (I): ##STR2## wherein R.sup.1 is an optionally protected carboxy(lower)alkyl, R.sup.2 is a hydrogen, an optionally substituted aryl or a carboxy, or an alkadienylene.
According to the present invention, the object compound (I) and a salt thereof can be prepared by the following processes. ##STR3## wherein each of R.sup.1, R.sup.2, X and Y is as defined above, R.sub.a.sup.1 is a protected carboxy(lower)alkyl,
Suitable salts of the compound (I) are conventional, nontoxic, pharmaceutically acceptable salts, and include salts with base or acid addition salts. There are exemplified salts with inorganic bases such as alkali metal salts (e.g. sodium salt, potassium salt, cesium salt), alkaline earth metal salts (e.g. calcium salt, magnesium salt) and ammonium salts; salts with organic bases such as organic amine salts (e.g. triethylamine salt, pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt); inorganic acid addition salts (e.g. hydrochloride, hydrobromide, sulfate, phosphate); organic carboxylic or sulfonic acid addition salts (e.g. formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, benzenesulfonate, p-toluenesulfonate); and salts with basic or acidic amino acids (e.g. arginine, aspartic acid, glutamic acid). The preferable salts are acid addition salts.
Suitable examples of the salts of the compounds (I-a), (I-b), (II), (III), (IV) and (V) in Processes 1 to 3 are to be referred to those as exemplified for the object compound (I).
In the above and subsequent descriptions of the present specification, suitable examples and illustrations of the various definitions which the present invention includes within the scope thereof are detailed as follows:
The term "lower" means that the number of carbon atoms is from 1 to 6, preferably 1 to 4, unless otherwise indicated.
Suitable "lower alkyl" includes straight or branched ones having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl and hexyl, preferable ones having 1 to 4 carbon atoms.
"Carboxy(lower)alkyl" means a lower alkyl as explained above, which is substituted by a carboxyl group at optional position(s). Example
Kuroda Akio
Okada Satoshi
Sawada Kozo
Tanaka Hirokazu
Watanabe Shinya
Fujisawa Pharmaceutical Co. Ltd.
Haley Jacqueline
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