Thursday, February 26, 2015

Zaleplon

Common name: Zaleplon; Sonata
Trademarks: Sonata; Starnoc; Andante
Molecular Formula: C17H15N5O
CAS Registry Number: 151319-34-5
CAS Name: N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide
Molecular Weight: 305.334
SMILES: CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N
InChI Key: HUNXMJYCHXQEGX-UHFFFAOYSA-N
InChI: InChI=1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3
Activity: GABA-A Receptor Agonists; Hypnotics and Sedatives;Ttreatment of Insomnia; Non-benzodiazepine Hypnotic; 
Status: Launched 1999
Originator: Wyeth

Zaleplon synthesis: US4626538

Zaleplon synthesis: Int J ChemTech Res 20102(1), 1-3 (High yields are reported)

References:
1. Dusza, J. P.; et. al. [7-(3-disubstituted amino)phenyl]pyrazolo[1,5-a]pyrimidines. US4626538
2. Thurairajah, P. Process improvement in the synthesis of N-[3-(3-cyanopyrazolo [1,5-a]pyrimidin-7-yl)phenyl]-N-ethyl-acetamide. EP0776898B1
3. Kankan, R. N.; et. al. Zaleplon synthesis. WO2005023813A1
4. Naik, A. M.; et. al. Novel process for the synthesis of Zaleplon. Int J ChemTech Res 2010, 2(1), 1-3.
5. Dooley, M.; et. al. Zaleplon: a review of its use in the treatment of insomnia. Drugs 2000, 60(2), 413-445. (activity)
6. Terzano, M. G.; et. al. New drugs for insomnia: comparative tolerability of zopiclone, zolpidem and zaleplon. Drug Saf 2003, 26(4), 261-282. (activity)