Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 706

Exclusivity
expiration
date
(United
States)

Active
ingredient
name

Commercial
name(s)

Type of
coupling(s)

FDA approval
date

Structure Ref. Applicant Indication

Ponatinib
hydro-
chloride

Iclusig Sonogashira

(two
instances)

31 Ariad

Pharmaceu-
ticals

BCR-ABL
inhibitor for
the treatment
of chronic
myeloid
leukemia and
Ph+ acute
lymphoblastic
leukemia

December
14, 2012

December
2026

N

Me

N

N O

N

N

￿HCl

CF 3

N

Terbinafine
hydro-
chloride

Lamisil Sonogashira 32 Novartis Antifungal March 17,

2000

Generic
(June
2007)

Me

N

￿HCl

Rizatriptan
benzoate

Maxalt Sonogashira

followed by
Larock
indolization

33 Merck 5-HT 1D receptor

agonist for the
treatment of
migraine

June 29,
1998

Generic
(December
2012)

NMe 2

N
N

N

￿PhCO 2 H

H

Ezetimibe Zetia

Ezetrol

Negishi 34 Merck/Schering-

Plough

Cholesterol
absorption
inhibitor

October 25,
2002

September
2013

OH

O

N

F

O

F