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Zomebazam

Chemical compound

Zomebazam

Chemical compound

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Zomebazam produced by Hoechst is a pyrazolodiazepinone derivative drug with anxiolytic properties. It is structurally related to razobazam and zometapine.

Synthesis

The catalytic hydrogenation of N,2,5-trimethyl-4-phenyldiazenylpyrazol-3-amine (1) over Raney nickel gives 4-amino-1,3-dimethyl-5-methylaminopyrazole (2). Treatment with methyl malonyl chloride (3) gives 4-α-ethoxycarbonylacetylamino-1,3-dimethyl-5-methylaminopyrazole (4). Base-catalyzed lactamization gives (5). The Goldberg reaction completes the synthesis of zomebazam (6).{{cite journal | vauthors = Renger B | title = Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion. | journal = Synthesis | date = 1985 | volume = 1985 | issue = 9 | pages = 856–560 | doi = 10.1055/s-1985-31364

Synthesis of zomebazam

References

Notes

References

  1. "4-Aryl-5,6,7,8-tetrahydropyrazolo(3,4-B)-(1,5)diazepine-1H,4H-5,7-diones and medicaments containing same".
  2. (2003). "Zomebazam". psychotropics.dk.
  3. {{cite patent
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gabaa-receptor-positive-allosteric-modulators lactams pyrazolodiazepines
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