Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 700

Table 15.2 List of commercial drugs synthesized through transition metal-catalyzed couplings, with the arrows pointing to the bond(s) created.

Exclusivity
expiration
date
(United
States)

Active
ingredient
name

Commercial
name(s)

Type of
coupling(s)

FDA approval
date Structure Ref. Applicant Indication

Atazanavir
sulfate

Reyataz Suzuki-

Miyaura

7 Bristol-Myers

Squibb

Protease
inhibitor for
the treatment
of HIV

June 20,
2003

April 2017 N

O

H
N

N OMe

O H

N

O

MeO N

H

O

￿H 2 SO 4

Pitavastatin
calcium

Livalo Suzuki-

Miyaura

8 Kowa/Sankyo HMG-CoA

reductase
inhibitor for
the treatment
of high
cholesterol

August 3,
2009

May 2015

F

OH OH

CO 2

￿1/2Ca 2

N

Garenoxacin
mesylate
hydrate

Geninax Suzuki-

Miyaura

9 Astellas Pharma/

Taisho Toyama
Pharmaceutical
Co./Toyama
Chemical Co.

Quinolone
antibiotic for
the treatment
of Gram-
positive and
Gram-negative
bacterial
infections

Never
approved
in the US
or EU.
Approved
in Japan
(2007).

Not
applicable

O

CO 2 H

N

HN

￿CH 3 SO 3 H￿H 2 O

O

F F