US 12,264,155 B2
Compounds, pharmaceutical compositions, and methods of preparing compounds and of their use as ATR kinase inhibitors
Sheldon N. Crane, Pincourt (CA); Vouy Linh Truong, Pierrefonds (CA); Abbas Abdoli, Montreal (CA); Jean-François Truchon, Saint-Laurent (CA); Cameron Black, St-Laurent (CA); Stéphane Dorich, Pointe-Claire (CA); Lee Fader, Hawkesbury (CA); Stéphanie Lanoix, Mansfield (CA); Paul Jones, Verdun (CA); Miguel St-Onge, Vaudreuil-Dorion (CA); Audrey Picard, Mirabel (CA); and Cyrus M. Lacbay, Montreal (CA)
Assigned to Repare Therapeutics Inc., St-Laurent (CA)
Filed by Repare Therapeutics Inc., St-Laurent (CA)
Filed on Apr. 30, 2021, as Appl. No. 17/245,574.
Application 17/245,574 is a continuation of application No. PCT/CA2019/051539, filed on Oct. 30, 2019.
Claims priority of provisional application 62/877,177, filed on Jul. 22, 2019.
Claims priority of provisional application 62/752,873, filed on Oct. 30, 2018.
Prior Publication US 2021/0277002 A1, Sep. 9, 2021
Int. Cl. C07D 471/04 (2006.01); C07D 519/00 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 519/00 (2013.01); C07B 2200/05 (2013.01)] 23 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein
custom characteris a double bond, and each Y is independently N or CR4; custom character or is a single bond, and each Y is independently NRY, carbonyl, or C (RY)2; wherein each RY is independently H or optionally substituted C1-6 alkyl;
R1 is optionally substituted C1-6 alkyl or H;
R2 is optionally substituted C2-9 heterocyclyl, optionally substituted C1-6 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C2-9 heterocyclyl C1-6 alkyl, optionally substituted C6-10 aryl, optionally substituted C1-9 heteroaryl, optionally substituted C1-9 heteroaryl C1-6 alkyl, halogen, —N(R5)2, —OR5, —CON(R6)2, —SO2N(R6)2, —SO2R5A, or -Q-R5B;
R3 is optionally substituted C1-9 heteroaryl;
each R4 is independently hydrogen, halogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, or optionally substituted C2-6 alkynyl;
each R5 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted C6-10 aryl C1-6 alkyl, optionally substituted C6-10 aryl, optionally substituted C1-9 heteroaryl, or —SO2R5A; or both R5, together with the atom to which they are attached, combine to form an optionally substituted C2-9 heterocyclyl;
each R5A is independently optionally substituted C1-6 alkyl, optionally substituted C3-8 cycloalkyl, or optionally substituted C6-10 aryl;
R5B is hydroxyl, optionally substituted C1-6 alkyl, optionally substituted C6-10 aryl, optionally substituted C1-9 heteroaryl, —N(R5)2, —CON(R6)2, —SO2N(R6)2, —SO2R5A, or optionally substituted alkoxy;
each R6 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkoxyalkyl, optionally substituted C6-10 aryl C1-6 alkyl, optionally substituted C6-10 aryl, optionally substituted C3-8 cycloalkyl, or optionally substituted C1-9 heteroaryl; or both R6, together with the atom to which they are attached, combine to form an optionally substituted C2-9 heterocyclyl;
Q is optionally substituted C2-9 heterocyclylene, optionally substituted C3-8 cycloalkylene, optionally substituted C1-9 heteroarylene, or optionally substituted C6-10 arylene; and
X is hydrogen or halogen.