Chemical compound
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Roluperidone (former developmental code names MIN-101, CYR-101, MT-210) is a [[5-HT2A receptor|5-HT2A]] and [[sigma-2 receptor|σ2 receptor]] [[receptor antagonist|antagonist]] under development by [[Minerva Neurosciences]] for the treatment of [[schizophrenia]]. One of its [[metabolite]]s also has some [[affinity (pharmacology)|affinity]] for the [[histamine H1 receptor|H1 receptor]]. Pre-clinical findings provide evidence of the effect of roluperidone on [[brain-derived neurotrophic factor]] ("BDNF"), which has been associated with neurogenesis, neuroplasticity, neuroprotection, synapse regulation, learning and memory.
As of May 2018, the drug was in [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s. In May 2020, the shares of Minerva Neurosciences plummeted 67% after the trial "failed to meet its primary endpoint of reduction in negative symptoms, and key secondary endpoints of improvement in personal and social performance measurements." However, in August 2022 Minerva submitted a New Drug Application (NDA) to the [[Food and Drug Administration]] (FDA) for the approval of roluperidone for the treatment of [[schizophrenia]]. The NDA submission in 2022 followed successful completion of a phase III clinical trial which was published in early 2022. Minerva believed that the findings of this second trial supported the claim that the drug was an effective agent for the treatment of negative symptoms in schizophrenia. However, in October 2022, FDA sent Minerva a refusal to file letter pertaining to the New Drug Application for roluperidone for treating negative symptoms in schizophrenia patients. 
Chemistry.
Synthesis.
[[File:Roluperidone synthesis.svg|thumb|center|500px|Patents: Precursor:]]
The Boc protection of 4-aminomethylpiperidine [7144-05-0] (1) gives tert-Butyl 4-aminomethylpiperidine-1-carboxylate hydrochloride [359629-16-6] (2). The free-radical halogenation of ethyl o-toluate [87-24-1] (3) led to ethyl 2-(bromomethyl)benzoate [7115-91-5] (4). The reaction between the two intermediates led to 2-[(1-tert-Butoxycarbonylpiperidin-4-yl)methyl]isoindolin-1-one [359629-19-9] (5). Deprotection yielded 2-(Piperidin-4-ylmethyl)-3H-isoindol-1-one;hydrochloride (6). Alkylation of the secondary nitrogen with 2-chloro-4'-fluoroacetophenone [700-35-6] (7) completed the synthesis of "Roluperidone" (8).
References.
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[[Category:5-HT2A antagonists]]
[[Category:Antipsychotics]]
[[Category:Isoindoles]]
[[Category:Ketones]]
[[Category:Organofluorides]]
[[Category:Piperidines]]
[[Category:Sigma antagonists]]
[[Category:Experimental drugs developed for schizophrenia]]