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Abandoned drugs
Ocaperidone
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    Ocaperidone

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    Ocaperidone
    Ocaperidone.svg
    Names
    Preferred IUPAC name
    3-{2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one
    Identifiers
    3D model (JSmol)
    ChemSpider
    KEGG
    MeSH C072259
    PubChem CID
    UNII
    • InChI=1S/C24H25FN4O2/c1-15-4-3-10-29-23(15)26-16(2)19(24(29)30)9-13-28-11-7-17(8-12-28)22-20-6-5-18(25)14-21(20)31-27-22/h3-6,10,14,17H,7-9,11-13H2,1-2H3
      Key: ZZQNEJILGNNOEP-UHFFFAOYSA-N
    • InChI=1/C24H25FN4O2/c1-15-4-3-10-29-23(15)26-16(2)19(24(29)30)9-13-28-11-7-17(8-12-28)22-20-6-5-18(25)14-21(20)31-27-22/h3-6,10,14,17H,7-9,11-13H2,1-2H3
      Key: ZZQNEJILGNNOEP-UHFFFAOYAT
    • CC1=CC=CN2C1=NC(=C(C2=O)CCN3CCC(CC3)C4=NOC5=C4C=CC(=C5)F)C
    Properties
    C24H25FN4O2
    Molar mass 420.488 g·mol−1
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    Ocaperidone (R 79598) is a benzisoxazole antipsychotic. 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, 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, ocaperidone produced an unacceptable amount of extrapyramidal side effects.

    Synthesis

    Synthesis according to patent (Ex4):

    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)..

    See also




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