Indole and indoline derivatives as 5-HT6 selective ligands
AssigneeMerck Sharp & Dohme Corp.
InventorsJose Luis Castro Pineiro, George Mc Allister, Michael Geoffrey Neil Russel
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Abstract
Three classes of indole and indoline derivatives are disclosed as ligands selective for the 5-HT6 receptors, and hence of value in the treatment or prevention of CNS disorders, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression and anxiety. A particular class, 1-substituted-4-(ω-N,N-dialkyl-aminoalkyl)indoles, are claimed as novel compounds.
Claims19
A method for the treatment and/or prevention of a clinical condition for which selective agonism or antagonism of 5-HT6 receptors is indicated comprising administering to a patient in need of such treatment an effective amount of a compound, or a pharmaceutically acceptable salt or prodrug thereof, having a structure in accordance with Formula I or II:
- wherein
- n is 1 or 2;
- p is 0,1,2 or 3;
- q is 0,1,2,3 or 4;
- R1 and R2 independently represent hydrogen, C1-6 alkyl or aryl (C1-6)alkyl, or together represent the atoms necessary to complete a heterocycloalkyl group comprising the nitrogen atom to which R1 and R2 are attached;
- R3 represents hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl(C1-6)alkyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl or C1-6 alkylcarbonyl;
- R4 represents arylsulphonyl, heteroarylsulphonyl, C1-6 alkylsulphonyl, di(C1-6)alkylaminosulphonyl, arylcarbonyl, C1-6 alkylcarbonyl, heteroarylcarbonyl or C1-6 alkoxycarbonyl;
- each R5 independently represents hydroxy, C1-6 alkoxy, aryl(C1-6)alkoxy, nitrile or halogen;
- and
- -A-B- represents —C═C— or —CH—CH—.
A compound of Formula I:
- wherein
- n is 1 or 2;
- p is 0,1,2 or 3;
- R1 and R2 independently represent hydrogen, C1-6 alkyl or aryl (C1-6)alkyl, or together represent the atoms necessary to complete a heterocycloalkyl group comprising the nitrogen atom to which R1 and R2 are attached;
- R3 represents hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl(C1-6)alkyl, aryl, heteroaryl, arylcarbonyl, heteroarylcarbonyl or C1-6 alkylcarbonyl;
- R4 represents arylsulphonyl, heteroarylsulphonyl, C1-6 alkylsulphonyl, di(C1-6)alkylaminosulphonyl, arylcarbonyl, C1-6 alkylcarbonyl, heteroarylcarbonyl or C1-6 alkoxycarbonyl;
- and
- each R5 independently represents hydroxy, C1-6 alkoxy, aryl(C1-6)alkoxy, nitrile or halogen,
- or a pharmaceutically acceptable salt or prodrug thereof.
Dependencies are inferred from the claim text.