1-phenyl-4-benzylpiperazines dopamine receptor subtype specific ligands
AssigneeNeurogen Corporation, A Corporation of the State of Delaware
InventorsAndrew Thurkauf, Xi Chen
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Abstract
Disclosed are compounds of the formula: 1 or the pharmaceutically acceptable addition salts thereof wherein: R1 is halogen or C1-C4 alkyl; and R2 and R3 are the same or different and represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, alkylthio, hydroxy, amino, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, or R2 and R3 together represent a 4 carbon alkenylene moiety that together with the phenyl ring to which they are attached form a naphthyl moiety, which compounds are useful in the treatment of neuropsycological diseases such as schizophrenia, psychotic depression and mania.
Claims35
A compounds of the formula:
- 12
- or the pharmaceutically acceptable acid salts thereof wherein:
- R1 is halogen or C1-C4 alkyl;
- R2 and R3 are the same or different and represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, alkylthio, hydroxy, amino, monoalkylamino or dialkylamino, with the proviso that R2 and R3 may not be 2-isopropoxyl and hydrogen respectively when R1 is bromo.
A compound of the formula:
- 13
- or the pharmaceutically acceptable salts thereof wherein
- Rx is fluorine, chlorine, bromine, or iodine;
- and
- R2 and R3 are the same or different and represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, alkylthio, hydroxy, amino, monoalkylamino or dialkylamino.
A compound of the formula:
- 15
- or the pharmaceutically acceptable salts thereof wherein
- Ra is C1-C4 alkyl;
- and
- R2 and R3 are the same or different and represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, alkylthio, hydroxy, amino, monoalkylamino or dialkylamino.
A compound of the formula:
- 17
- or the pharmaceutically acceptable salts thereof wherein:
- R1 is C1-C4 alkyl or halogen.
A method for treating or preventing neuropsychological disorders which comprises administering to a patient in need of such treatment a compound selected from the group consisting of
- (a) 1-(3-chlorophenyl)-4-(4-chlorobenzyl)piperazine;
- (b) 1-(2-chlorophenyl)-4-(4-chlorobenzyl)piperazine;
- (c) 1-(3,4-dichlorophenyl)-4-(4-chlorobenzyl)piperazine;
- (d) 1-(4-methylphenyl)-4-(4-chlorobenzyl)piperazine;
- (e) 1-(3-methylphenyl)-4-(4-chlorobenzyl)piperazine;
- (f) 1-(2-methylphenyl)-4-(4-chlorobenzyl)piperazine;
- (g) 1-(3,4-dimethylphenyl)-4-(4-chlorobenzyl)piperazine;
- (h) 1-(4-methoxyphenyl)-4-(4-chlorobenzyl)piperazine;
- (i) 1-(3-methoxyphenyl)-4-(4-chlorobenzyl)piperazine;
- (j) 1-(2-methoxyphenyl)-4-(4-chlorobenzyl)piperazine;
- (k) 1-(4-ethoxyphenyl)-4-(4-chlorobenzyl)piperazine,
- (l) 1-(2-ethoxyphenyl)-4-(4-chlorobenzyl)piperazine;
- (m) 1-phenyl-4-(4-chlorobenzyl)piperazine;
- (n) 1-(4-chlorophenyl)-4-(4-fluorobenzyl)piperazine;
- (o) 1-(4-chlorophenyl)-4-(4-methylbenzyl)piperazine;
- (p) 1-(3-chlorophenyl)-4-(4-methylbenzyl)piperazine;
- (q) 1-(4-chlorophenyl)-4-(4-methylbenzyl)piperazine;
- (r) 1-(3,4-dichlorophenyl)-4-(4-methylbenzyl)piperazine;
- (s) 1-(4-methylphenyl)-4-(4-methylbenzyl)piperazine;
- (t) 1-(2-methylphenyl)4(4-methylbenzyl)piperazine;
- (u) -methoxyphenyl)-4-(4-methylbenzyl)piperazine;
- (v) -methoxyphenyl)-4-(4-methylbenzyl)piperazine;
- (w) 1-(4-chlorophenyl)-4-(4-chlorobenzyl)piperazine dihydrochloride;
- and
- (x) 1-(2-isopropoxyphenyl)-4-(4-bromobenzyl)piperazine.
Dependencies are inferred from the claim text.