Syntheses and metabolism of selected antipsychotics
General synthesis of phenothiazine neuroleptics
NH R
1
S or SCl2
t°
N
H
S
R
1
+
N
H
S R
1
1. NaNH2
N
R
2
R3
X
N
S
R
1
N
R
2
R3
R1
: -Cl, -OCH3, -CN, -CF3
R2
, R3
: -CH3, or R2
+R3
=piperidine,
piperazine
Other approach to phenothiazine skeleton: synthesis of thioridazine
Br
SH
+
N
+
O
–
O
Cl
S
CH3
-HCl
Br
S
N
+
O
–
O
S
CH3
H2
Br
S
NH2
S
CH3
+ N
CH3
Cl
Br
S
NH
S
CH3
NCH3
-HBr
S
N S
CH3
N
CH3
Metabolism of chlorpromazine
Original synthesis of haloperidol
Metabolism of haloperidol
Synthesis of clozapine
Main methabolic pathways of clozapine
Synthesis of quetiapine
Sertindole synthesis
Other modification of sertindole synthesis
Synthesis of ziprasidone
Main metabolites of ziprasidone
Some other metabolites of ziprasidone
Synthesis of risperidone
3-(2-hydroxyethyl)-2-methyl-2,3-dihydro-4H-pyrido[1,2-a]pyrimidin-4-one
6-fluoro-3-(piperidin-4-yl)-1,2-benzoxazole
Main metabolic pathways of risperidone
paliperidone
Synthesis of paliperidone
Main metabolites of paliperidone
= paliperidone
Synthesis of sulpiride
Synthesis of levosulpiride
Synthesis of amisulpride