Tuesday, March 10, 2015

Almotriptan

Common name: Almotriptan; LAS-31416; Axert; Almotriptan Malate
Trademarks: Axert; Almogran; Almotrex; Amignul
Molecular Formula: C17H25N3O2S
CAS Registry Number: 181183-52-8
CAS Name: dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
Molecular Weight: 335.464
SMILES: CN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C2
InChI Key: WKEMJKQOLOHJLZ-UHFFFAOYSA-N
InChI: InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3
Activity: Treatment of  Migraines; Serotonin Antagonists; Serotonin Receptor Agonists; Anti-migraine Agents
Status: Launched 2001
Originator: Almiral/Janssen

Almotriptan synthesis: Scheme 1 [Tetrahedron 2001, 57(6), 1041-1048 (also Ref. 2)]

Almotriptan synthesis: Scheme 2 (Tetrahedron 2001, 57(6), 1041-1048) 
Almotriptan synthesis: Scheme 3 (Tetrahedron 2001, 57(6), 1041-1048)

Almotriptan synthesis: US5565447A

Almotriptan synthesis: WO2006129190A1
References:
1. Bosch, J.; et. al. Synthesis of 5-(sulfamoylmethyl)indoles. Tetrahedron 2001, 57(6), 1041-1048.
2.  Fernandez, M.-D.; et. al. ES2084560B1
3.  Forner, D. F.; et. al. Almotriptan malate; treating headaches, movement disorders, depression, anxiety. US5565447A
4. Pradhan, N. S. C.; et. al. Process for the preparation of almotriptan. WO2006129190A1
5. Keam, S. J.; et. al. Almotriptan: a review of its use in migraine. Drugs 2002, 62(2), 387-414. (activity)
6. Pascual, J.; et. al. Almotriptan: a review of 10 years' clinical experience. Expert Rev Neurother 2010, 10(10), 1505-1517. (activity)
7. Gras, J.; et. al. Almotriptan, a new anti-migraine agent: a review. CNS Drug Rev 2002, 8(3), 217-234. (activity)

For more drugs and their synthesis: Synayurajan database