Flufenoxine Explained

Drug Name:	Flufenoxine
Width:	250px
Cas Number:	957202-15-2
Pubchem:	9817317
Chemspiderid:	7993067
Synonyms:	F-98214-TA
C:	18
H:	20
F:	1
N:	1
O:	1
Smiles:	C1CNCCC1C(C2=CC=CC=C2)OC3=CC(=CC=C3)F

Flufenoxine (F-98214-TA) is a Serotonin–norepinephrine reuptake inhibitor. It can be used to treat disorders of the central nervous system, particularly depression and anxiety. It was developed by a Spanish company at the beginning of the 21st century.^[1]

Flufenoxine derivatives have been patented for the treatment of Alzheimer's disease.^[2]

Analogues of Flufenoxine were reported containing a duloxetine-type thiophene surrogate ring moiety.^[3] Such agents possess the desired triple-mode of activity (serotonin-noradrenaline and dopamine) (c.f. SNDRI).

Synthesis

The synthesis of Flufenoxine was disclosed in a pair of patents:^{[4] [5]} Ex 1: The base catalyzed ether formation between tert-butyl 4-[hydroxy(phenyl)methyl]piperidine-1-carboxylate [269740-46-7] (1) and 1,3-difluorobenzene [372-18-9] (2) gave a racemic mixture of (3).

Notes and References

1. Artaiz I, Zazpe A, Innerárity A, Del Olmo E, Díaz A, Ruiz-Ortega JA, Castro E, Pena R, Labeaga L, Pazos A, Orjales A . Preclinical pharmacology of F-98214-TA, a novel potent serotonin and norepinephrine uptake inhibitor with antidepressant and anxiolytic properties . Psychopharmacology . 182 . 3 . 400–13 . November 2005 . 16032410 . 10.1007/s00213-005-0087-3 .
2. Francisco Ledo Gómez, et al. WO2011147780 (Fabrica Espanola de Productos Quimicos y Farmaceuticos FAES SA).
3. 郭强, et al. WO2015131814 (to WUHAN JIAYU TECHNOLOGY Co Ltd, Nhwa Pharmaceutical Corp).
4. Venero Aurelio Orjales, et al. EP1002794 (2000 to Fabrica Espanola de Productos Quimicos y Farmaceuticos FAES SA).
5. Aurelio Orjales Venero, Ramón MOSQUERA PESTAÑA, Mª Carmen PUMAR DURÁN, Antonio Toledo Avello, Gonzalo Canal Mori, Maravillas Bordell Martín, WO2007131846 (Fabrica Espanola de Productos Quimicos y Farmaceuticos FAES SA).