Ocaperidone (R 79598) is a
benzisoxazoleantipsychotic.[1] It was initially developed by
Janssen, later licensed to French laboratory Neuro3D and then acquired in 2007 by German company
Evotec. It was found to be more potent than
risperidone in animal studies,[2] but its testing was abandoned in 2010 after unfavorable results in human Phase II trials,[3] as while it was effective at controlling symptoms of
schizophrenia, ocaperidone produced an unacceptable amount of
extrapyramidal side effects.[4]
Synthesis
The last step requires attachment of the sidechain between 3-(2-bromoethyl)-2,9-dimethyl 4H-pyrido[1,2-a]pyrimidin-4-one,
CID:18995805 (1) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole [84163-77-9] (2) completing the
convergent synthesis of Ocaperidone (3)..
^Leysen, JE; Janssen, PM; Gommeren, W; Wynants, J; Pauwels, PJ; Janssen, PA (1992). "In vitro and in vivo receptor binding and effects on monoamine turnover in rat brain regions of the novel antipsychotics risperidone and ocaperidone". Molecular Pharmacology. 41 (3): 494–508.
PMID1372084.
^Megens AA, Awouters FH, Meert TF, Schellekens KH, Niemegeers CJ, Janssen PA. Pharmacological profile of the new potent neuroleptic ocaperidone (R 79,598). J Pharmacol Exp Ther. 1992 Jan;260(1):146-59.
PMID1370538
^"Ocaperidone — AdisInsight". Adis Insight. Adis International Ltd, part of Springer Science+Business Media. Retrieved 10 December 2015.
^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.
doi:
10.1371/journal.pone.0049732PMID23251349
^Ludo E. J. Kennis, Jan Vandenberk, & Albertus H. M. T. Van Heertum, U.S. patent 5,482,943 (1996 to Janssen Pharmaceutica NV).
Ocaperidone (R 79598) is a
benzisoxazoleantipsychotic.[1] It was initially developed by
Janssen, later licensed to French laboratory Neuro3D and then acquired in 2007 by German company
Evotec. It was found to be more potent than
risperidone in animal studies,[2] but its testing was abandoned in 2010 after unfavorable results in human Phase II trials,[3] as while it was effective at controlling symptoms of
schizophrenia, ocaperidone produced an unacceptable amount of
extrapyramidal side effects.[4]
Synthesis
The last step requires attachment of the sidechain between 3-(2-bromoethyl)-2,9-dimethyl 4H-pyrido[1,2-a]pyrimidin-4-one,
CID:18995805 (1) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole [84163-77-9] (2) completing the
convergent synthesis of Ocaperidone (3)..
^Leysen, JE; Janssen, PM; Gommeren, W; Wynants, J; Pauwels, PJ; Janssen, PA (1992). "In vitro and in vivo receptor binding and effects on monoamine turnover in rat brain regions of the novel antipsychotics risperidone and ocaperidone". Molecular Pharmacology. 41 (3): 494–508.
PMID1372084.
^Megens AA, Awouters FH, Meert TF, Schellekens KH, Niemegeers CJ, Janssen PA. Pharmacological profile of the new potent neuroleptic ocaperidone (R 79,598). J Pharmacol Exp Ther. 1992 Jan;260(1):146-59.
PMID1370538
^"Ocaperidone — AdisInsight". Adis Insight. Adis International Ltd, part of Springer Science+Business Media. Retrieved 10 December 2015.
^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.
doi:
10.1371/journal.pone.0049732PMID23251349
^Ludo E. J. Kennis, Jan Vandenberk, & Albertus H. M. T. Van Heertum, U.S. patent 5,482,943 (1996 to Janssen Pharmaceutica NV).