US 9,809,590 B2
Substituted N-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide compounds as type III receptor tyrosine kinase inhibitors
Mark Laurence Boys, Boulder, CO (US); Robert Kirk DeLisle, Lyons, CO (US); Erik James Hicken, Boulder, CO (US); April L. Kennedy, Denver, CO (US); David A. Mareska, McMurray, PA (US); Fredrik P. Marmsater, Boulder, CO (US); Mark C. Munson, Acton, MA (US); Brad Newhouse, Boulder, CO (US); Bryson Rast, Westminster, CO (US); James P. Rizzi, Addison, TX (US); Martha E. Rodriguez, Lafayette, CO (US); George T. Topalov, Pittsburgh, PA (US); and Qian Zhao, El Cerrito, CA (US)
Assigned to Array BioPharma Inc., Boulder, CO (US)
Filed by Array BioPharma Inc., Boulder, CO (US)
Filed on Sep. 18, 2015, as Appl. No. 14/858,029.
Application 14/858,029 is a continuation of application No. 13/994,048, previously published as PCT/US2011/064549, filed on Dec. 13, 2011.
Claims priority of provisional application 61/422,547, filed on Dec. 13, 2010.
Prior Publication US 2016/0002232 A1, Jan. 7, 2016
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01); A61K 45/06 (2006.01); A61K 31/496 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 31/496 (2013.01); A61K 45/06 (2013.01)] 29 Claims
 
1. A compound having the general formula I

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
R1 is hetAr1(CH2)m—, hetAr2CH2— or hetAr3CH2;
hetAr1 is a 6-membered heteroaryl having 1-2 ring N atoms and optionally substituted with one or more substituents independently selected from (1-6C)alkyl, (1-4C)alkoxy, halogen, CF3, or (3-6C)cycloalkyl;
m is 0, 1 or 2;
hetAr2 is a 5-membered heteroaryl ring having 2-3 ring heteroatoms independently selected from N and S where at least one of said heteroatoms is N, wherein said ring is optionally substituted with one or more substituents independently selected from (1-6C)alkyl;
hetAr3 is a bicyclic 5,6-fused heteroaryl ring having two ring nitrogen atoms;
R2 is CH3;
R3 is H;
R4 is H;
R5 is hetCyc4(1-4C)alkoxy or hetCyc5(1-4C)alkoxy;
hetCyc4 is a 4-7 membered heterocycle having 1-2 ring heteroatoms independently selected from N, O and S, wherein one of said ring nitrogen atoms is optionally oxidized to N(O) and wherein said S ring atom is optionally oxidized to SO or SO2, wherein hetCyc4 is optionally substituted with one or more substituents independently selected from halogen, OH, (1-6C)alkyl, (1-4C alkoxy)(1-6C)alkyl, (1-4C)alkyl-OC(═O)— and (1-6C)alkoxy;
hetCyc5 is a spiro heterocycle having 2 ring heteroatoms independently selected from N and O, wherein hetCyc5 is optionally substituted with a group selected from (1-6C)alkyl; and
R6 is H.