Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 701

Losartan
potassium

Cozaar

Cl

Suzuki-
Miyaura
(same
coupling can
be employed
for
structurally
similar drugs
such as
candesartan,
irbesartan
and
valsartan)

10 Merck Angiotensin II

receptor
antagonist for
the treatment
of high blood
pressure

April 28,
1995

Generic
(August
2009)

N

OH

n -Bu

N
N

N

N

K

N

Eltrombopag
olamine

Promacta
(USA),
Revolade
(EU)

Suzuki-
Miyaura

11 GlaxoSmithKline Treatment of

idiopathic
thrombo-
cytopenia
(abnormally
low platelet
count)

November
20, 2008

December
2021 ￿2 NH 2 CH 2 CH 2 OH

O

N

OH

H
N

N

N CO 2 H

Rofecoxib Vioxx

Ceoxx
Ceeoxx

Suzuki-
Miyaura

12 Merck Non-steroidal

anti-
inflammatory

May 20,
1999

Withdrawn

MeO 2 S

O

O

Etoricoxib Arcoxia Suzuki-

Miyaura (two
instances)

13 Merck COX-II inhibitor

for the
treatment of
pain and
inflammation

Never
approved
in the US.
Approved
in over 70
countries
worldwide

Not
applicable

SO 2 Me

Cl

N

N