Thiazolyl- or thiadiazolyl-substituted pyridyl compounds useful as kinase inhibitors

Patent metadata

Field	Value
Publication number	US-9242976-B2
Application number	US-201314371463-A
Country	US
Kind code	B2
Filing date	Jan 11, 2013
Priority date	Jan 13, 2012
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

Compounds having the following formula (I) or an enantiomer, diastereomer or a pharmaceutically-acceptable salt thereof, wherein X is N or C—R 7 , are useful as kinase modulators, including IRAK-4 modulation.

First claim

What is claimed is:

1. A compound having the following formula:

or a stereoisomer or pharmaceutically-acceptable salt thereof, wherein
X is N;
R is —C(═O)—R 1 , —C(═O)O—R 1 or —C(═O)NR 11 —R 1 ;
R 1 is piperidinyl substituted with 0-3 R 1a ;
R 1a is hydrogen, —OCF 3 , —CN, —(CH 2 ) r OR b , —(CH 2 ) r C(O)R b , —(CH 2 ) r C(O)OR b , —(CH 2 ) r OC(O)R b , —(CH 2 ) r NR 11 R 11 , —(CH 2 ) r C(O)NR 11 R 11 , —(CH 2 ) r NR b C(O)R c , —(CH 2 ) r NR b C(O)OR c , —S(O) p NR 11 R11, —NR b S(O) p R c , —S(O) 2 R c , or C 1-6 alkyl substituted with 0-2 R a ;
R 2 is benzo[d]thiazolyl;
R 3 is propyl substituted with 0-3 R 3a ;
R 3a is —OH or phenyl;
R 11 at each occurrence is hydrogen;
R a is R d , F, Cl, Br, OCF 3 , CF 3 , CHF 2 , or CN;
R b is R e , C 1-6 alkyl, or C 1-6 haloalkyl;
R c is CH 3 ;
R d is hydrogen;
R e is hydrogen;
p is 0, 1, or 2; and
r is 0, 1, or 2.

2. The compound of claim 1 , or a stereoisomer or pharmaceutically-acceptable salt thereof, wherein R 2 is

3. The compound according to claim 1 , or a stereoisomer or pharmaceutically-acceptable salt thereof, wherein R 3 is —CH(CH 3 ) 2 .

4. The compound according to claim 1 , or a stereoisomer or pharmaceutically-acceptable salt thereof, wherein R 1a is —OH or —NH 2 .

5. The compound according to claim 1 or a stereoisomer or pharmaceutically acceptable salt thereof, wherein:
R is —C(═O)—R 1 ;
R 1 is piperidinyl substituted with 0-1 R 1a ; and
R 1a is hydrogen, —OH, or —NH 2 .

6. The compound according to claim 1 , or a stereoisomer or pharmaceutically-acceptable salt thereof, wherein said compound is selected from

7. A pharmaceutical composition comprising one or more compounds according to claim 1 and a pharmaceutically acceptable carrier or diluent.

Assignees

• Bristol Myers Squibb Co

Inventors

• Paidi Venkatram Reddy
• Kumar Sreekantha Ratna
• Banerjee Abhisek
• Sistla Ramesh
• Nair Satheesh Kesavan
• Pitts William J
• Hynes John

Classifications

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P35/04

  specific for metastasis · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P37/02

  Immunomodulators · CPC title

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title