Annual Activities Report 2011 - INCT-Inofar - UFRJ

Annual Report 2011 | INCT-INOFAR
35
Synthesis of
Sunitinib and
Synthesis of
Fluoxetine
Synthesis of fluoxetine hydrocloride
Eliezer J. Barreiro a , Luiz C. Dias b , Adriano S. Vieira b
a
Instituto Nacional de Ciência e Tecnologia de Fármacos e Medicamentos,
Universidade Federal do Rio de Janeiro, CCS, Rio de Janeiro-RJ.
b
Universidade Estadual de Campinas, Instituto de Química,
Departamento de Química Orgânica, Campinas-SP.
INTRODUCTION
The INCT-INOFAR leads projects that aim to
develop new and innovative synthetic routes of
generic drugs already available in the market as
well as for those that have patents about to expire.
These projects are in the area of incremental and
radical innovation, one of the important focus of
the INCT-INOFAR. In this part of the project
,the selected drug was fluoxetine hydrochloride.
Fluoxetine hydrochloride is an antidepressant of the
class of selective inhibitors of serotonin reuptake.
Its main indications are for use in moderate to
severe depression, obsessive compulsive disorder
(OCD) and nervous bulimia. It is marketed and
used as a racemic mixture.
RESULTS AND DISCUSSION
Initially, we carried out a literature search on
the synthetic routes of fluoxetine hydrochloride
described in patents and papers. We have developed
a very efficient synthetic strategy to prepare 2g of
fluoxetin hydrochloride.
The synthetic route developed is short, efficient and
uses inputs readily available commercially available in
the national market (only two inputs are imported)
at a relatively low cost. Moreover, the process
generates a lower environmental impact since some
of the employed solvents are from renewable sources.
This fact has a very positive impact on reducing the
cost of production of the active ingredient.
CONCLUSIONS
In summary, fluoxetine hydrochloride was obtained
in four steps in an overall yield of 51.5% after
recrystallization from acetonitrile at -20 °C.
In this process, we used incremental innovation to
propose an efficient synthetic route, not described
in prior patents of Fluoxetine, in which the drug
can be prepared in a practical way.