Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 710

Exclusivity
expiration
date
(United
States)

Active
ingredient
name

Commercial
name(s)

Type of
coupling(s)

FDA approval
date

Structure Ref. Applicant Indication

Avanafil Stendra

Spedra

C-N bond
formation

49 Vivus PDE5 inhibitor

for the
treatment of
erectile
dysfunction

April 27,
2012

September
2020

MeO

Cl

HN N N

N

N

N

OH

N

O

Irbesartan Aprovel

Karvea
Avapro

Ullmann biaryl
synthesis

50 Sanofi-Aventis

(marketed with
Bristol-Myers
Squibb)

Angiotensin II
receptor
antagonist
for the
treatment of
hypertension

September
30, 1997

Generic
(March
2012)

N

O

N

N

N

N N

Carvedilol Carvil

Coreg
Dilatrend
Eucardic
Carloc

Ullmann
homo-
coupling

51 Wyeth Non-selective

b-blocker/a-1
blocker of
adrenergic
receptor for the
treatment of
congestive
heart failure

1995 Generic

(March 5,
2007)

O N

H

OMe

OH O

H