Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-11-08
1996-03-05
McKane, Joseph K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514414, 514419, 5142352, 514323, 514339, 514365, 514383, 514384, 514397, 548465, 548469, 548494, 548509, 548181, 5482664, 5483121, 546201, 546273, 544143, 544144, A61K 3140, C07D20904
Patent
active
054968445
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/SP93/0056 filed Apr. 28, 1993.
TECHNICAL FIELD
The present invention relates to novel indole derivatives.
PRIOR ART
The indole derivatives of the invention are novel compounds not yet described in the literature.
DISCLOSURE OF INVENTION
It is an object of the invention to provide compounds useful as drugs, as mentioned later herein.
According to the invention, indole derivatives of the general formula (1) shown below are provided. ##STR2##
In the above formula, R.sup.1 is a halogen atom, R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkanoyl group or a benzoyl group, R.sup.3 is a hydrogen atom, a lower alkyl group or a halogen atom, R.sup.4 is a thienyl group or a group of the formula ##STR3## (in which R.sup.6 is a lower alkyl group, a cycloalkyl group, a phenyl group which may optionally have a lower alkyl group as a substituent, a phenyl-lower alkyl group or a pyridyl group, R.sup.7 is a hydrogen atom or a lower alkyl group, Q is a sulfur or selenium atom and n is an integer of 0 to 2), A is an alkylene group, m is an integer of 0 to 1, R.sup.5 is a hydrogen atom, an alkyl group or a benzoyl group having a hydroxyl group or a group of the formula --O--B--R.sup.8 (in which B is a lower alkylene group and R.sup.8 is a phenyl, di-lower alkyl-amino, 1-pyrrolidinyl, piperidino, 1-imidazolyl or 1,2,4-triazol-1-yl group) as a substituent when m is 0 or, when m is 1, R.sup.5 is a lower alkoxycarbonyl group, a carboxyl group, a hydroxyl group, a group of the formula --C(.dbd.O)--N(R.sup.9)--R.sup.10 (in which R.sup.9 and R.sup.10 are the same or different and each is a hydrogen atom, a lower alkyl group, a cycloalkyl group which may optionally have a benzene ring condensed thereto, a phenyl group, a phenyl-lower alkyl group or a lower alkylsulfonyl group or R.sup.9 and R.sup.10 are bound to each other either directly or via an oxygen or sulfur atom to form, together with the adjacent nitrogen atom, a heterocyclic group which may optionally be substituted with a lower alkoxycarbonyl or carboxyl group), a group of the formula --CH.sub.2 --N(R.sup.11)--R.sup.12 (in which R.sup.11 and R.sup.12 are the same or different and each is a hydrogen atom, a lower alkyl group, a cycloalkyl group which may optionally have a benzene ring condensed thereto, a phenyl group, a phenyl-lower alkyl group or a lower alkanoyl group or R.sup.11 and R.sup.12 are bound to each other either directly or via an oxygen or sulfur atom to form, together with the adjacent nitrogen atom, a heterocyclic group which may optionally be substituted with a lower alkoxycarbonyl or carboxyl group), a group of the formula --OR.sup.13 (in which R.sup.13 is a lower alkylcarbamoylphenyl group, a lower alkylaminomethylphenyl group, a lower alkylaminomethylphenyl group, a 1-pyrrolidinylcarbonylphenyl group, a 1-pyrrolidinylmethylphenyl group, a 2-di-lower alkylaminoethyl group or a 2-hydroxyl-2-lower alkylaminoethyl group) or a phenyl group which may optionally have a hydroxyl, lower alkoxy, 1-pyrrolidinylcarbonyl or 1-pyrrolidinylmethyl group as a substituent, and x is an integer of 0 to 2.
As the groups appearing in the above general formula (1), there may be mentioned the following examples. The lower alkyl group includes straight or branched lower alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and hexyl. The alkyl group includes heptyl, octyl, nonyl, decyl and the like in addition to the lower alkyl groups mentioned above. The lower alkanoyl group includes, among others, acetyl, propionyl, butyryl, valeryl, pivaloyl, hexanoyl and heptanoyl.
As the cycloalkyl group, there may be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.
Thus, the cycloalkyl group which may optionally have a benzene ring condensed thereto includes, in addition to the cycloalkyl groups mentioned above, 1-indanyl, 2-indanyl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, etc.
The phenyl-lower alkyl group is, for example, benzyl
REFERENCES:
patent: 3564009 (1971-02-01), Yamamoto et al.
patent: 4543360 (1985-09-01), von Angerer et al.
patent: 4661511 (1987-04-01), von Angerer et al.
patent: 4943572 (1990-07-01), van Angerer
patent: 5023254 (1991-06-01), von Angerer
J. Med. Chem., 27, p. 1439 (1984), von Angerer et al., 2 Phenylindoles . . . , in the Rat.
Chemical Abstracts, vol. 99 (1983), Studies . . . aromatic amines., Tao et al., p. 570.
Inai Masatoshi
Kanaya Jun
Moritake Masako
Shibutani Tadanao
Tanaka Akie
McKane Joseph K.
Otsuka Pharmaceutical Factory Inc.
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