Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 708

Table 15.2 (Continued)

Exclusivity
expiration
date
(United
States)

Active
ingredient
name

Commercial
name(s)

Type of
coupling(s)

FDA approval
date Structure Ref. Applicant Indication

Abacavir
sulfate

Ziagen Tsuji-Trost 41 Glaxo Wellcome Reverse

transcriptase
inhibitor for
the treatment
of HIV

December
18, 1998

Generic
(December
2009)

HN

N
N

N

N NH 2

￿1/2H 2 SO 4

HO

Aripiprazole Abilify

Aripiprex

C-N bond
formation

42 Otsuka

(marketed with
Bristol-Myers
Squibb)

Partial
dopamine
agonist for the
treatment of
schizophrenia,
bipolar
disorder and
clinical
depression

November
15, 2002

October
2014

N

O O

N

N

Cl

Cl

Eribulin
mesylate

Halaven Nozaki-

Hiyama-
Kishi
(asymmetric)

43 Eisai Mitotic inhibitor

for the
treatment of
cancer

November,
2010

June 2019

MeO

H

O O

HO
H 2 N

O

O

H

H

O

O

O

￿MsOH

O

H

O