Ocaperidone

Chemical compound From Wikipedia, the free encyclopedia

Ocaperidone (R 79598) is a benzisoxazole antipsychotic.[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]

Quick facts Names, Identifiers ...
Ocaperidone
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
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).
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Synthesis

The last step requires attachment of the sidechain between 3-(2-bromoethyl)-2,9-dimethyl 4H-pyrido[1,2-a]pyrimidin-4-one (1) and 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2) completing the convergent synthesis of ocaperidone (3).

Patented method for the synthesis of ocaperidone[5]

See also

References

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