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, previously known as neuroleptics and major tranquilizers, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), p ...

. 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, as well as aggressive and self-injurious behaviors associated with autism spectrum disorder. It is t ...

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 variously by hallucinations (typically, Auditory hallucination#Schizophrenia, hearing voices), delusions, thought disorder, disorganized thinking and behavior, and Reduced affect display, f ...

, ocaperidone produced an unacceptable amount of extrapyramidal side effects.

Synthesis

The last step requires attachment of the sidechain between 3-(2-bromoethyl)-2,9-dimethyl 4''H''-pyrido

,2-a The comma is a punctuation mark that appears in several variants in different languages. Some typefaces render it as a small line, slightly curved or straight, but inclined from the vertical; others give it the appearance of a miniature fille ...

yrimidin-4-one (1) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (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, a ...

of ocaperidone (3). Ocaperidone synthesis

References

{{Serotonergics 5-HT2 antagonists Abandoned drugs Antihistamines Antipsychotics Alpha blockers Benzisoxazoles D2 antagonists

Synthesis

See also

References