US 2006/0148815 A1 · 4-Phenyl-1-piperazinyl, -piperidinyl and-tetrahydropyridyl derivatives

Abstract

The present invention relates to substituted 4-phenyl-1-piperazinyl derivatives having the formula I wherein W is C, CH or N, and the dotted line emanating from W indicates a bond when W is C and no bond when W is N or CH; X is CH2, O, S, CO, CS, SO or SO2; and Q is a group of formula wherein Z is a chain of 3 to 4 chain members; wherein the chain members are selected from C, CH, CH2, CO, N and NH, provided that only one of the chain members may be N or NH, and said chain optionally containing one or two double bonds; provided that X is not O or S when the group Q is attached via an N atom; and any of its enantiomers and acid addition salts thereof. These compounds have high affinity for D4 receptors.

Claims16

Dependent claims

A compound of formula I

wherein
W is N;
R1 and R2 are independently halogen;
R3 is selected from hydrogen, halogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, trifluoromethyl, C1-6-alkoxy, aryloxy, aralkoxy, hydroxy, amino, C1-6-alkylamino, di(CI-6-alkyl)amino, nitro and cyano;
n is 2, 3, 4 or 5;
X is CH2, S, or C(O);
and
Q is a group of formula
R4, R5, R6, R7, R8 and R9 are independently selected from hydrogen, halogen, trifluoromethyl, nitro, cyano, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkoxy, C1-6-alkylthio, C1-6-alkylsulfonyl, hydroxy, hydroxy-C1-6 alkyl, amino, C1-6-alkylamino, di(C1-6-alkyl)amino, acyl, aminocarbonyl, C1-6-alkylaminocarbonyl and di(C1-6-alkyl)aminocarbonyl;
and any of its enantiomers and acid addition salts thereof.

7 more elements

A compound

4-[4-(2-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one,
4-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one,
1-{4-[4-(2-Chlorophenyl)piperazin-1-yl]butyl}-2,3-dihydro-1H-indole,
1-{4-[4-(3-Chlorophenyl)piperazin-1-yl]butyl}-2,3-dihydro-1H-indole,
6-Chloro-3-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethylsulfanyl}-1H-indole,
3-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-1H-indole,
3-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butyl}-1H-indole,
3-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-5-fluoro-1H-indole,
3-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butyl}-5-fluoro-1H-indole,
6-Chloro-3-{3-[4-(2,3-dichlorophenyl)piperazin-1-yl]propyl}-1H-indole,
3-[4-(2-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one,
5-[4-(2-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)pentan-1-one,
3-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one,
5-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)pentan-1-one,
3-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-1-one,
5-[4-(3-Chlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)pentan-1-one,
3-[4-(2-Chlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-1-one,
4-[4-(2-Chlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)butan-1-one,
1-(2,3-Dihydro-1H-indol-1-yl)-3-[4-(2-fluoro-phenyl)-piperazin-1-yl]-propan-1-one,
1-(2,3-Dihydro-1H-indol-1-yl)-4-[4-(2-fluoro-phenyl)-piperazin-1-yl]-butan-1-one,
1-(2,3-Dihydro-1H-indol-1-yl)-5-[4-(2-fluoro-phenyl)-piperazin-1-yl]-pentan-1-one,
1-(5-Fluoro-2,3-dihydro-1H-indol-1-yl)-3-[4-(2-fluoro-phenyl)-piperazin-1-yl]-propan-1-one,
1-(5-Fluoro-2,3-dihydro-1H-indol-1-yl)-4-[4-(2-fluoro-phenyl)-piperazin-1-yl]-butan-1-one,
1-(5-Fluoro-2,3-dihydro-1H-indol-1-yl)-5-[4-(2-fluoro-phenyl)-piperazin-1-yl]-pentan-1-one,
3-[4-(2,4-Difluoro-phenyl)-piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one,
4-[4-(2,4-Difluoro-phenyl)-piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one,
5-[4-(2,4-Difluoro-phenyl)-piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)pentan-1-one,
3-[4-(2,4-Difluoro-phenyl)-piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-1-one
3-[4-(3,4-Dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one,
4-[4-(3,4-Dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one,
3-[4-(3,4-Dichlorophenyl)piperazin-1-yl]-1-(5-fluoro-2,3-dihydro-1H-indol-1-yl)propan-1-one, or an enantiomer or acid addition salt thereof.

28 more elements

Dependencies are inferred from the claim text.

4-Phenyl-1-piperazinyl, -piperidinyl and-tetrahydropyridyl derivatives

Life of this patent

4-Phenyl-1-piperazinyl, -piperidinyl and-tetrahydropyridyl derivatives

Life of this patent

Abstract

Claims16