US 12,275,741 B2
Cardiac sarcomere inhibitors
Chihyuan Chuang, Millbrae, CA (US); Bradley P. Morgan, Oakland, CA (US); Mark Vanderwal, Oakland, CA (US); Luke W. Ashcraft, San Francisco, CA (US); and Kevin Lau, San Mateo, CA (US)
Assigned to Cytokinetics, Inc., South San Francisco, CA (US)
Filed by Cytokinetics, Inc., South San Francisco, CA (US)
Filed on Feb. 26, 2024, as Appl. No. 18/587,730.
Application 18/587,730 is a continuation of application No. 17/736,895, filed on May 4, 2022, granted, now 11,952,381.
Application 17/736,895 is a continuation of application No. 16/557,281, filed on Aug. 30, 2019, granted, now 11,414,424, issued on Aug. 16, 2022.
Claims priority of provisional application 62/726,162, filed on Aug. 31, 2018.
Prior Publication US 2024/0368172 A1, Nov. 7, 2024
Int. Cl. C07D 487/10 (2006.01); A61P 9/04 (2006.01); C07D 241/08 (2006.01); C07D 241/38 (2006.01); C07D 401/04 (2006.01); C07D 401/06 (2006.01); C07D 401/08 (2006.01); C07D 403/08 (2006.01); C07D 405/04 (2006.01); C07D 405/12 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/08 (2006.01); C07D 413/14 (2006.01); C07D 417/08 (2006.01); C07D 491/107 (2006.01)
CPC C07D 487/10 (2013.01) [A61P 9/04 (2018.01); C07D 241/08 (2013.01); C07D 241/38 (2013.01); C07D 401/04 (2013.01); C07D 401/06 (2013.01); C07D 401/08 (2013.01); C07D 403/08 (2013.01); C07D 405/04 (2013.01); C07D 405/12 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/08 (2013.01); C07D 413/14 (2013.01); C07D 417/08 (2013.01); C07D 491/107 (2013.01)] 13 Claims
 
1. A method of preparing a compound of formula (1a-7)

OG Complex Work Unit Chemistry
or a salt thereof, comprising:
(i) reacting a compound of formula (1a-1)

OG Complex Work Unit Chemistry
or a salt thereof, with a compound of formula (1a-2)

OG Complex Work Unit Chemistry
or a salt thereof, to form a compound of formula (1a-3)

OG Complex Work Unit Chemistry
or a salt thereof; and
(ii) converting the compound of formula (1a-3) or salt thereof to the compound of formula (1a-7) or salt thereof;
wherein:
R1a is selected from the group consisting of cyano, halo, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, and substituted or unsubstituted heterocyclyl;
R2A and R2B are defined by (i) or (ii):
(i) R2A is H or substituted or unsubstituted alkyl; and
R2B is substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl; or
(ii) R2A and R2B are taken together with the carbon atom to which they are attached to form G1, wherein G1 is a substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclyl ring, each of which is optionally fused to a phenyl ring;
Alk2 is C1-C6 alkyl; and
Alk is C1-C6 alkyl.