Monday, March 16, 2015

Eletriptan

Common name: Eletriptan; UK-116044; Relpax; Eletriptan hydrobromide
Trademarks: Relpax
Molecular Formula: C22H26N2O2S
CAS Registry Number: 143322-58-1
CAS Name: 5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
Molecular Weight: 382.519
SMILES: CN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C2
InChI Key: PWVXXGRKLHYWKM-LJQANCHMSA-N
InChI: InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1
Activity: Anti-migraine Agents; Serotonin Antagonists; Serotonin Receptor Agonists;  5-Hydroxytryptamine 1B/1D Receptor Agonist; 5-HT1B Receptor Agonist
Status: Launched 2002
Originator: Pfizer

Eletriptan synthesis: US5545644A (oldest synthesis reference)
Eletriptan synthesis: US7288662B2 (improvement on the earlier synthesis, removes the problem due to dimerization in the above synthesis. Loved by Pfizer, not so by others !!!!)
Eletriptan synthesis: WO2005103035A1


References:
1. Macor, J. E.; et. al. Indole derivatives. US5545644A
2. Ogilvie, R. J. Process for the preparation of eletriptan. US7288662B2
3. Ashcroft, C.P. Modified fischer indole synthesis of eletriptan. WO2005103035A1

For more drugs and their synthesis: Synayurajan database