Ocaperidone (R 79598) is a

benzisoxazole 1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C7H5NO containing a benzene-fused isoxazole ring structure. The compound itself has no common applications; however, functionalized benzisoxazoles and benzisoxazoyls have ...

antipsychotic Antipsychotics, also known as neuroleptics, are a class of psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but also in a range of ...

. It was initially developed by Janssen, later licensed to French laboratory Neuro3D and then acquired in 2007 by German company

Evotec Evotec SE is a publicly listed drug discovery and development company headquartered in Hamburg, Germany. The company operates globally, largely through external alliances with pharmaceutical and biotechnology companies, academic institutions, ...

. It was found to be more potent than

risperidone Risperidone, sold under the brand name Risperdal among others, is an atypical antipsychotic used to treat schizophrenia and bipolar disorder. It is taken either by mouth or by injection (subcutaneous or intramuscular). The injectable versions ...

in animal studies, but its testing was abandoned in 2010 after unfavorable results in human Phase II trials, as while it was effective at controlling symptoms of

schizophrenia Schizophrenia is a mental disorder characterized by continuous or relapsing episodes of psychosis. Major symptoms include hallucinations (typically hearing voices), delusions, and disorganized thinking. Other symptoms include social wit ...

, ocaperidone produced an unacceptable amount of extrapyramidal side effects.Geerts H, Spiros A, Roberts P, Twyman R, Alphs L, Grace AA. Blinded prospective evaluation of computer-based mechanistic schizophrenia disease model for predicting drug response. ''PLoS One''. 2012;7(12):e49732.

Synthesis

The last step requires attachment of the sidechain between 3-(2-bromoethyl)-2,9-dimethyl 4H-pyrido ,2-ayrimidin-4-one
CID:18995805
(1) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole 4163-77-9(2) completing the

convergent synthesis In chemistry a convergent synthesis is a strategy that aims to improve the efficiency of multistep synthesis, most often in organic synthesis. In this type of synthesis several individual pieces of a complex molecule are synthesized in stage one, ...

of Ocaperidone (3)..

References

5-HT2 antagonists Abandoned drugs Antihistamines Antipsychotics Alpha blockers Benzisoxazoles D2 antagonists {{nervous-system-drug-stub

Synthesis

See also

References