US 12,006,321 B2
Substituted pyrazolo[1,5-a]pyrimidines as apelin receptor agonists
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 May 12, 2022, as Appl. No. 17/742,977.
Application 17/742,977 is a continuation of application No. 16/637,652, granted, now 11,345,705, previously published as PCT/US2018/045837, filed on Aug. 8, 2018.
Claims priority of provisional application 62/543,265, filed on Aug. 9, 2017.
Prior Publication US 2023/0037225 A1, Feb. 2, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/519 (2006.01); C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) 21 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
R1 is H, halogen, CN, alkyl, C(O)N(R7)2, C(O)OH, C(O)OR6, NH2, O(alkyl), O(phenyl), or aryl, wherein the alkyl is optionally substituted with one or more substituents independently selected from the group consisting of OH and O(alkyl);
R2 is H, halogen, CN, alkyl, C(O)N(R7)2, C(O)OH, C(O)OR6, NH2, O(alkyl), O(phenyl), or aryl, wherein the alkyl is optionally substituted with one or more substituents independently selected from the group consisting of OH and O(alkyl);
R3 is alkyl;
R4 is alkyl, haloalkyl, or cycloalkyl;
R5 is C(O)N(R9)2, C(O)OH, or C(O)OR8;
each R6 is independently H, alkyl, haloalkyl, NH2, O(alkyl), O(haloalkyl), cycloalkyl, heterocycloalkyl, phenyl, or 5- or 6-membered heteroaryl;
each R7 is independently H, alkyl, haloalkyl, NH2, O(alkyl), O(haloalkyl), cycloalkyl, heterocycloalkyl, phenyl, or 5- or 6-membered heteroaryl;
R8 is H, alkyl, haloalkyl, NH2, O(alkyl), O(haloalkyl), cycloalkyl, heterocycloalkyl, phenyl, or 5- or 6-membered heteroaryl; and
each R9 is independently H, alkyl, haloalkyl, NH2, O(alkyl), O(haloalkyl), cycloalkyl, heterocycloalkyl, phenyl, or 5- or 6-membered heteroaryl.