Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 703

Valsartan Angiotan

Diovan

Suzuki-
Miyaura

18 Novartis Non-peptidic

angiotensin-II-
receptor
antagonist
for the
treatment of
hypertension

December
23, 1996

September
2012

CO 2 H

O

N

n -Bu

N
HN

N N

Perampanel Fycompa Suzuki-

Miyaura,
Stille, N-
arylation

19 Eisai AMPA receptor

antagonist for
the treatment
of epilepsy

October 22,
2012

June 2021

N-Arylation
(Cu-catalyzed)

Suzuki − Miyaura

or Stille

N O

CN

N

Suzuki − Miyaura

Lapatinib
ditosylate
hydrate

Tykerb Stille 20 SmithKline

Beecham
(now part of
GlaxoSmith-
Kline)

ErB-1 and ErB-2
dual kinase
inhibitor for
the treatment
of breast
cancer

March 13,
2007

July 2017

O

F

MeO 2 S

NH HN Cl

O

N (TsOH￿H 2 O) 2

N

Rilpivirine
hydro-
chloride

Edurant

N N

Heck 21 Janssen

Products
(originally
developed by
Tibotec)

Reverse
transcriptase
inhibitor for
the treatment
of HIV-1
infection

May 20,
2011

February
2021

￿HCl

N

N

NC CN

Nabumetone Relafen
Relifex
Gambaran
(Belgium,
Luxem-
bourg)

Heck 22 Hoechst-

Celanese
(originally
developed by
Beecham)

Non-steroidal
anti-
inflammatory

December
1991

Generic

O

MeO