US 12,071,414 B2
Apelin receptor agonists and methods of use thereof
Layton H. Smith, Orlando, FL (US); Anthony B. Pinkerton, Rancho Santa Fe, CA (US); Paul Hershberger, Satellite Beach, FL (US); Patrick Maloney, Orlando, FL (US); and Danielle McAnally, Gainesville, FL (US)
Assigned to SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE, La Jolla, CA (US)
Filed by Sanford Burnham Prebys Medical Discovery Institute, La Jolla, CA (US)
Filed on Apr. 28, 2023, as Appl. No. 18/309,634.
Application 18/309,634 is a continuation of application No. 16/869,307, filed on May 7, 2020, granted, now 11,673,873.
Application 16/869,307 is a continuation of application No. 15/568,208, granted, now 10,647,689, issued on May 12, 2020, previously published as PCT/US2016/029823, filed on Apr. 28, 2016.
Claims priority of provisional application 62/154,025, filed on Apr. 28, 2015.
Prior Publication US 2023/0339872 A1, Oct. 26, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 277/82 (2006.01); A61P 3/00 (2006.01); A61P 9/00 (2006.01); C07D 263/58 (2006.01); C07D 513/04 (2006.01)
CPC C07D 277/82 (2013.01) [A61P 3/00 (2018.01); A61P 9/00 (2018.01); C07D 263/58 (2013.01); C07D 513/04 (2013.01)] 20 Claims
 
1. A compound of formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
A is selected from the group consisting of substituted phenoxy and heteroaryl-oxy;
R2 and R3 are each independently selected from the group consisting of C1-C6 haloalkyl, C1-C6 haloalkoxy, optionally substituted C1-C6 alkyl, and optionally substituted C1-C6 alkoxy;
each R5-R7 is independently selected from the group consisting of hydrogen, halogen, —CN, —C(O)—N(R10)—R11, —C(O)—O—R12, —SO2R13, C1-C6 alkyl, C3-C8 cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
each R10-R12 is independently selected from the group consisting of hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, optionally substituted phenyl, optionally substituted amino, and optionally substituted 5- or 6-membered heteroaryl; and
R13 is optionally substituted C1-C6 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, optionally substituted phenyl, optionally substituted amino, or optionally substituted 5- or 6-membered heteroaryl.