IP Library Granted Patent US 9,586,948
Granted Patent B2
US 9,586,948 · App. 14/434,348 · Granted Mar 7, 2017

Inhibitors of IRAK4 activity

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Quick Facts
Patent No.
US 9,586,948
App. No.
14/434,348
Granted
Mar 7, 2017
Kind
B2
Abstract

The present invention relates to inhibitors of IRAK4 of Formula (I) and provides compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

Claims (19)

1. A compound of Formula III:

wherein:

X is CH;

a is 0 or 1; b is 0 or 1 m is 0, 1 or 2;

R 1 is selected from: H, oxo, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b -aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, halo, OH, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a NR 5 R 6 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m NR 5 R 6 , SH, and S(O) m -(C 1 -C 10 )alkyl, said alkyl, aryl, alkenyl, alkynyl, and cycloalkyl are optionally substituted with one or more substituents selected from R a ;

R 5 and R 6 are independently selected from: H, (C═O) a O b (C a -C 10 )alkyl, (C═O) a O b -aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a N(R a ) 2 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m N(R a ) 2 , SH, and S(O) m -(C 1 -C 10 )alkyl, said alkyl, aryl, alkenyl, alkynyl, and cycloalkyl are optionally substituted with one or more substituents selected from R a ;

R a is independently selected from R b , OH, (C 1 -C 6 )alkoxy, halogen, cyclopropyl, CO 2 H, CN, O a (C═O) b (C 1 -C 6 )alkyl, oxo, and N(R b ) 2 ; and

R b is independently selected from H and (C 1 -C 6 )alkyl;

or a pharmaceutically acceptable salt or a stereoisomer thereof.

2. A compound which is selected from:

N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-2′-((cyclopropylmethyl)amino)-[2,4′-bipyridine]-6-carboxamide;

tert-butyl(6-((3-carbamoyl-1 -methyl-1H-pyrazol-4-yl)carbamoyl)[2,4′-bipyridin]-2′-yl)carbamate;

2′-amino-N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)[2,4′-bipyridine]-6-carboxamide;

N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-2,4′-bipyridine-6-carboxamide;

N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-2′-((2-methoxyethyl)amino)-[2,4′-bipyridine]-6-carboxamide;

N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-2′-((2,2-difluoroethyl)amino)-[2,4′-bipyridine]-6-carboxamide; and

N-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)-2′-((2,2,2-trifluoroethyl)amino)-[2,4′-bipyridine]-6-carboxamide;

or a pharmaceutically acceptable salt or stereoisomer thereof.

3. A pharmaceutical composition comprising a pharmaceutical carrier, and dispersed therein, a therapeutically effective amount of a compound of claim 1 .

Assignments (2)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2016
From: SEGANISH, WILLIAM MICHAEL; HANISAK, JENNIFER; LI, GUOQING; ZHANG, RUI; TANG, HAIQUN
To: MERCK SHARP & DOHME CORP.
Reel/Frame 037579/0190 →