Elzasonan

Elzasonan (CP-448,187) is a selective 5-HT1B and 5-HT1D receptor antagonist that was under development by Pfizer for the treatment of depression but was discontinued, possibly due to poor efficacy.[1][2][3][4][5] By preferentially blocking 5-HT1B and 5-HT1D autoreceptors, elzasonan is thought to enhance serotonergic innervations originating from the raphe nucleus, thereby improving signaling to limbic regions like the hippocampus and prefrontal cortex and ultimately resulting in antidepressant effects.[3]

Elzasonan
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • 4-(3,4-dichlorophenyl)-2-[2-(4-methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H23Cl2N3OS
Molar mass448.41 g·mol−1
3D model (JSmol)
SMILES
  • Clc4c(Cl)cc(N1C(=O)C(\SCC1)=C\c3ccccc3N2CCN(C)CC2)cc4
InChI
  • InChI=1S/C22H23Cl2N3OS/c1-25-8-10-26(11-9-25)20-5-3-2-4-16(20)14-21-22(28)27(12-13-29-21)17-6-7-18(23)19(24)15-17/h2-7,14-15H,8-13H2,1H3/b21-14-
  • Key:LHYMPSWMHXUWSK-STZFKDTASA-N
  (verify)

Synthesis
Patent:[6]

The aldol condensation of 2-(4-Methylpiperazino)benzaldehyde [85803-62-9] (1) with 4-(3,4-dichlorophenyl)thiomorpholin-3-one [205683-35-8] (2) gives Elzasonsan (3).

See also

References
  1. Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. ISBN 978-3-527-31058-6.
  2. Stahl SM (2008). Stahl's essential psychopharmacology: neuroscientific basis and practical applications. Cambridge, UK: Cambridge University Press. ISBN 978-0-521-85702-4.
  3. Dawson LA, Bromidge SM (August 2008). "5-HT1 receptor augmentation strategies as enhanced efficacy: therapeutics for psychiatric disorders". Current Topics in Medicinal Chemistry. 8 (12): 1008–23. doi:10.2174/156802608785161439. PMID 18691129.
  4. Norman P (2002). "Pfizer, Inc.: analysis of patenting 1998 – 2001". Expert Opinion on Therapeutic Patents. 12 (5): 725–732. doi:10.1517/13543776.12.5.725. S2CID 84645020.
  5. Kirchhoff VD, Nguyen HT, Soczynska JK, Woldeyohannes H, McIntyre RS (October 2009). "Discontinued psychiatric drugs in 2008". Expert Opinion on Investigational Drugs. 18 (10): 1431–43. doi:10.1517/13543780903184591. PMID 19715445. S2CID 34201544.
  6. Joseph P. Rainville, Terry G. Sinay, Stanley W. Walinsky, U.S. Patent 6,608,195 (2003 to Pfizer Inc.).
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.