US 11,851,429 B2
AMPK activators
Iyassu Sebhat, Jersey City, NJ (US); Shuwen He, Fanwood, NJ (US); Ann Weber, Cranford, NJ (US); Nancy Thornberry, Westfield, NJ (US); Lisa Krug, New York, NY (US); Paul Richards, New York, NY (US); and Brett Lauring, New York, NY (US)
Assigned to KALLYOPE, INC., New York, NY (US)
Filed by Kallyope, Inc., New York, NY (US)
Filed on Jan. 26, 2022, as Appl. No. 17/584,831.
Application 17/584,831 is a continuation of application No. 17/502,474, filed on Oct. 15, 2021, granted, now 11,279,702.
Application 17/502,474 is a continuation of application No. PCT/US2021/032933, filed on May 18, 2021.
Claims priority of provisional application 63/141,169, filed on Jan. 25, 2021.
Claims priority of provisional application 63/111,837, filed on Nov. 10, 2020.
Claims priority of provisional application 63/027,231, filed on May 19, 2020.
Prior Publication US 2022/0227754 A1, Jul. 21, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01); A61P 1/04 (2006.01); A61P 1/12 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 1/04 (2018.01); A61P 1/12 (2018.01)] 20 Claims
 
1. A compound of Formula (III):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, solvate, stereoisomer, or prodrug thereof, wherein:
R2 is halogen, —CN, C1-C4 alkyl, or C1-C4 fluoroalkyl;
R3 and R4 are each independently hydrogen, C1-C4 alkyl, or C1-C4 fluoroalkyl;
G is —C(O)OR7, —P(O)(R8)OR7, —P(O)(OR7)2, or —S(O)2OR7;
each R7 is independently hydrogen or C1-C4 alkyl;
R8 is C1-C4 alkyl;
A is C3-C8 cycloalkyl, 3- to 8-membered heterocycloalkyl, C6-C10 aryl, or 5- to 10-membered heteroaryl, which is substituted with 1, 2, or 3 R12 groups;
each R12 is independently halogen, —CN, —OH, —OR13, —NR14R14, —C(═O)R13, —C(═O)OR14, —OC(═O)R14, —C(═O)NR14R14, —NR14C(═O)R14, —NR14C(═O)NR14R14, —OC(═O)NR14R14, —NR14C(═O)OR13, —OC(═O)OR13, —OSO2OR14, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 fluoroalkyl, C3-C6 cycloalkyl, 3- to 6-membered heterocycloalkyl, phenyl, or monocyclic heteroaryl;
each R13 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 fluoroalkyl, C3-C6 cycloalkyl, 3- to 6-membered heterocycloalkyl, phenyl, or monocyclic heteroaryl; and
each R14 is independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 fluoroalkyl, C3-C6 cycloalkyl, 3- to 6-membered heterocycloalkyl, phenyl, or monocyclic heteroaryl;
or two R14 on the same nitrogen atom are taken together with the nitrogen to which they are attached to form a 3- to 6-membered N-heterocycloalkyl.