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US 5,849,731 AGranted
Indole derivatives and medical application thereof
AssigneeToray Industries, Inc.
InventorsHiroshi Nagase, Koji Kawai, Takashi Endo, Shinya Ueno, Masayuki Maeda, Satoshi Sakami
Life of this patent
Estimating the term…
Abstract
The present invention relates to indole derivatives represented by the following compound 1 and the pharmacologically acceptable acid addition salt thereof. ##STR1## The compounds of the present invention were found to exhibit strong antitussive and analgesic actions as a result of pharmacological evaluation, and can be used in the pharmaceutical field as effective antitussives and analgesics.
Claims13
An indole derivative represented by the following general formula (I) or a pharmacologically acceptable acid addition salt thereof:
- ##STR19## wherein:
- R.sup.1 is hydrogen, an alkyl having 1 to 5 carbon atoms, a cycloalkylalkyl having 4 to 7 carbon atoms, a cycloalkenylalkyl having 5 to 7 carbon atoms, an aryl having 6 to 12 carbon atoms, an aralkyl having 7 to 13 carbon atoms, an alkenyl having 3 to 7 carbon atoms, a furan-2-yl-alkyl in which the alkyl has 1 to 5 carbon atoms, or a thiophene-2-yl-alkyl in which the alkyl has 1 to 5 carbon atoms;
- R.sup.2 is hydrogen, hydroxy, an alkoxy having 1 to 5 carbon atoms, or an alkanoyloxy having 1 to 5 carbon atoms;
- R.sup.3 is hydrogen, hydroxy, an alkoxy having 1 to 5 carbon atoms, an alkanoyloxy having 1 to 5 carbon atoms, or an aralkyloxy having 7 to 13 carbon atoms;
- --X-- is a crosslinkage comprising 2 to 5 carbon atoms in which at least one of the carbon atoms may be replaced with a nitrogen atom, an oxygen atom, or a sulfur atom;
- m is an integer from 0 to 3;
- n is an integer from 0 to 10;
- each of m R.sup.4 groups and n R.sup.5 groups is individually fluoro, chloro, bromo, iodo, nitro, an alkyl having 1 to 5 carbon atoms, an alkoxy having 1 to 5 carbon atoms, trifluoromethyl, trifluoromethoxy, cyano, phenyl, a hydroxyalkyl having 1 to 3 carbon atoms, isothiocyanato, SR.sup.6, SOR.sup.6, SO.sub.2 R.sup.6, (CH.sub.2).sub.p OR.sup.6, (CH.sub.2).sub.p CO.sub.2 R.sup.6, SO.sub.2 NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, (CH.sub.2).sub.p NR.sup.7 R.sup.8, or (CH.sub.2).sub.p N(R.sup.7)COR.sup.8, in which p is an integer from 0 to 5;
- R.sup.6 is an alkyl having 1 to 5 carbon atoms;
- each of R.sup.7 and R.sup.8 is individually hydrogen, an alkyl having 1 to 5 carbon atoms, or a cycloalkylalkyl having 4 to 7 carbon atoms;
- and among the above m R.sup.4 groups and n R.sup.5 groups, at least one pair of adjacent R.sup.4 groups, adjacent R.sup.5 groups, and one R.sup.4 and one R.sup.5 groups may be linked to form a benzene, pyridine, cyclopentane, cyclohexane, or cycloheptane condensed ring;
- R.sup.9 is hydrogen, alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an aralkyl having 7 to 13 carbon atoms, a hydroxyalkyl having 1 to 3 carbon atoms, (CH.sub.2).sub.p OR.sup.6, or (CH.sub.2).sub.p CO.sub.2 R.sup.6, in which definitions of p and R.sup.6 are the same as above;
- R.sup.10 and R.sup.11 are linked to form an --O--, --S--, or --CH.sub.2 -- group;
- or R.sup.10 is hydrogen while R.sup.11 is independently hydrogen, hydroxy, an alkoxy having 1 to 5 carbon atoms, or an alkanoyloxy having 1 to 5 carbon atoms;
- and
- the compound expressed by the general formula (I) may be a (+) form, a (-) form, or a (.+-.) form.
13 more elements
Dependencies are inferred from the claim text.