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US 5,731,352 AGranted
Aryl(alkyl)propylamides
AssigneeAdir et Compagnie
InventorsDaniel Lesieur, Veronique Leclerc, Patrick Depreux, Philippe Delagrange, Pierre Renard
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Abstract
The invention relates to a compound selected from those of formula (I): ##STR1## in which A, R.sub.1, R'.sub.1, R.sub.2, R.sub.3 and n are as defined in the description, and medicinal product containing the same useful for treating a mammal afflicted with a disorder of the melatoninergic system.
Claims9
A compound selected from the group consisting of those of formula (I):
- ##STR64## in which:
- R.sub.1 represents hydrogen, hydroxyl, a radical R.sub.6, or a group --O--R.sub.6, R.sub.6 being selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, cycloalkylalkyl, substituted cycloalkylalkyl, alkenyl, alkynyl, cycloalkenyl, phenyl, substituted phenyl, phenylalkyl, substituted phenylalkyl, dicycloalkylalkyl, substituted dicycloalkylalkyl, diphenylalkyl, and substituted diphenylalkyl,
- R'.sub.1 is selected from the group consisting of hydrogen, halogen, R'.sub.6, --O--R'.sub.6, --OH, --CO--R.sub.7, --CH.sub.2 --R.sub.7, and --O--CO--R.sub.7,
- R'.sub.6 being selected from the group consisting of the same meanings as R.sub.6, which is as defined above, the radicals R.sub.6 and R'.sub.6 being identical or different,
- R.sub.7 represents a radical selected from the group consisting of (C.sub.1 -C.sub.5)alkyl, substituted (C.sub.1 -C.sub.5)alkyl, cycloalkyl, substituted cycloalkyl, cycloalkyl(C.sub.1 -C.sub.5)alkyl, substituted cycloalkyl(C.sub.1 -C.sub.5) alkyl, phenyl, substituted phenyl, phenyl(C.sub.1 -C.sub.5)alkyl, and substituted phenyl(C.sub.1 -C.sub.5)alkyl,
- A, with the benzene ring to which it is linked, forms a cyclic group selected from the group consisting of tetrahydronaphthalene, dihydronaphthalene, naphthalene, benzothiophene, 2,3-dihydrobenzothiophene, benzofuran, 2,3-dihydrobenzofuran, indole, and indoline,
- n represents zero, 1, 2, or 3,
- R.sub.2 represents hydrogen or alkyl,
- R.sub.3 represents:
- a group of formula (R.sub.31):
- ##STR65## with X representing sulfur or oxygen and R.sub.4 representing hydrogen or a radical selected from the group consisting of alkyl, substituted alkyl, alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkylalkyl, and substituted cycloalkylalkyl,
- it not being possible for the compound of formula (I) to represent N-3-(4-hydroxy-1-naphthyl)propyl!acetamide or N-3-(4-benzyloxy-1-naphthyl)propyl!acetamide, on the understanding that:
- when A, with the benzene ring to which it is linked, forms a benzothiophene group, R.sub.4 is an alkyl or vinyl radical, R.sub.1 is hydrogen or methyl and R'.sub.1 is hydrogen, then n is other than zero,
- when A, with the benzene ring to which it is linked, forms a benzothiophene or indole group, n is equal to zero, R.sub.2 represents hydrogen, R'.sub.1 represents hydrogen or a phenyl, methyl, or benzyl radical substituted on the nitrogen of the indole group formed by A, and R.sub.1 represents hydrogen or methyl, then R.sub.4 cannot be methyl or ethyl, its enantiomers and diastereoisomers,
- and an addition salt thereof with a pharmaceutically-acceptable base.
12 more elements
Dependencies are inferred from the claim text.