Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 707

Vismodegib Erivedge

Cl

O Cl

Negishi 35 Genentech SMO receptor

antagonist for
the treatment
of basal cell
carcinoma

January 30,
2012

November
2028

N

H

SO 2 Me

Tazarotene Tazorac

Avage
Zorac

Negishi 36 Allergan Topical retinoid

for the
treatment of
acne, psoriasis
and sun
damaged skin

June 13,
1997

June 2011
(no
generic
version
available)

CO 2 Et

N

S

Oseltamivir
phosphate

Tamiflu Carbonylation 37 Gilead Sciences/

F. Hoffmann-
La Roche

Neuraminidase
inhibitor for
the treatment
of influenza

October 27,
1999

December
2016

O CO 2 Et

AcHN

NH 2 ￿H 3 PO 4

Ibuprofen Motrin

Nurofen
Advil
Nuprin

Carbonylation 38 Hoechst-

Celanese

Non-steroidal
anti-
inflammatory

1961 Generic

CO 2 H

Diflunisal Dolobid Kumada-

Corriu

39 Merck Non-steroidal

anti-
inflammatory

April, 1982 April 1992

OH

F

CO 2 H

F

Varenicline Chantix

Champix

Carbonyl a-
arylation

40 Pfizer Smoking

cessation

May 11,
2006

November
2018

N

NH

N