US 4,522,828 AGranted

Therapeutic agents

AssigneeThe Boots Company PLC

InventorsJames E. Jeffery, Antonin Kozlik, Eric C. Wilmshurst

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Abstract

Compounds of formula I ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, cycloalkylalkyl or optionally substituted phenyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, formyl, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring show therapeutic activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.

Claims29

Dependent claims

A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I ##STR36## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl group contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms and groups of formula II ##STR37## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms;
in which R.sub.3 ad R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbons atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;
in which R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring;
or a pharmaceutically acceptable salt thereof.

1 more element

A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III ##STR38## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl groups contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms, and groups of formula II ##STR39## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms;
in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;
in which R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring;
or a pharmaceutically acceptable salt thereof.

1 more element

A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV ##STR40## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl group contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms and groups of formula II ##STR41## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms;
in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;
in which R.sub.5 is selected from the group consisting of H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms and phenyl;
in which R.sub.6 is fluoro or methyl;
or a pharmaceutically acceptable salt thereof.

2 more elements

Dependencies are inferred from the claim text.