US 11,952,381 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 May 4, 2022, as Appl. No. 17/736,895.
Application 17/736,895 is a continuation of application No. 16/557,281, filed on Aug. 30, 2019, granted, now 11,414,424.
Claims priority of provisional application 62/726,162, filed on Aug. 31, 2018.
Prior Publication US 2023/0090256 A1, Mar. 23, 2023
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)] 20 Claims
 
1. A method of preparing a compound of formula (1b-10)

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

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

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

OG Complex Work Unit Chemistry
or a salt thereof; and
(ii) converting the compound of formula (1b-3) or salt thereof to the compound of formula (1b-10) or salt thereof;
wherein:
R1 is selected from the group consisting of substituted or unsubstituted phenyl and substituted or unsubstituted pyridyl;
R2a is selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted aminoacyl, substituted or unsubstituted aminothionyl, substituted or unsubstituted acyl, substituted or unsubstituted aminosulfonyl, substituted or unsubstituted aminocarbonylamino, substituted or unsubstituted alkyl, substituted or unsubstituted pyridin-one-yl, substituted or unsubstituted pyridazin-one-yl, substituted or unsubstituted 9-membered bicyclic heterocyclyl, and hydroxyl;
R3 is selected from the group consisting of unsubstituted C2-C6 alkyl, alkyl substituted with alkoxy, cyano, or halo, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
R4 is H or unsubstituted alkyl;
R5 is H or substituted or unsubstituted alkyl;
n is 1 or 2; and
Alk1 is unsubstituted C1-C6 alkyl.