Ocinaplon

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Ocinaplon
Clinical data
ATC code
  • none
Identifiers
  • pyridin-2-yl-(7-pyridin-4-ylpyrazolo[1,5-a]pyrimidin-3-yl)methanone
JSmol)
  • O=C(c1cnn2c(ccnc12)c3ccncc3)c4ncccc4
  • InChI=1S/C17H11N5O/c23-16(14-3-1-2-7-19-14)13-11-21-22-15(6-10-20-17(13)22)12-4-8-18-9-5-12/h1-11H checkY
  • Key:OQJFBUOFGHPMSR-UHFFFAOYSA-N checkY
  (verify)

Ocinaplon is an anxiolytic drug in the pyrazolopyrimidine family of drugs. Other pyrazolopyrimidine drugs include zaleplon and indiplon.

Ocinaplon has a similar pharmacological profile to the

amnestic effect.[1]

Medical uses

A 2019 review found tentative evidence of benefit in anxiety.[2]

Mechanism of action

The mechanism of action by which ocinaplon produces its anxiolytic effects is by modulating GABAA receptors,[3] although ocinaplon is more subtype-selective than most benzodiazepines.[4]

Availability

Development of ocinaplon is discontinued due to liver complications that occurred in one of the Phase III subjects.[5]

Synthesis

Ocinaplon synthesis: U.S. patent 4,521,422 Further reading:[6][7]

Condensation of 4-Acetylpyridine[8] with N,N-Dimethylformamide dimethyl acetal (DMFDMA) gives the "enamide" (3). This is then condensed with (3-Amino-1H-pyrazol-4-yl)(2-pyridinyl)methanone (4) (96219-90-8).[9][10] This is the same intermediate as was used in the synthesis of zaleplon in which the nitrile is replaced by a 2-acetylpyridil moiety. This affords the anxiolytic agent ocinaplon (5).

References

  1. PMID 15870187
    .
  2. S2CID 72332967
    .
  3. S2CID 21913400
    .
  4. S2CID 22793644
    .
  5. ^ "DOV Pharmaceutical, Inc. Places Ocinaplon Phase III Clinical Trial On Hold". PR NewsWire. Archived from the original on 4 March 2016.
  6. PMID 24204439
    .
  7. ^ ARKIVOC 2010 (ii) 267-282
  8. doi:10.15227/orgsyn.064.0019
    .
  9. ^ U.S. patent 4,900,836
  10. ^ CA 1243029 
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