US 12,318,426 B2
Compositions and methods for the treatment of metabolic and liver disorders
Brian Lian, Rancho Santa Fe, CA (US); Geoffrey E. Barker, Carlsbad, CA (US); Maureen Barnes, San Diego, CA (US); Kader Yagiz, San Diego, CA (US); and Erland Stevens, Davidson, NC (US)
Assigned to Viking Therapeutics, Inc., San Diego, CA (US)
Filed by Viking Therapeutics, Inc., San Diego, CA (US)
Filed on Jul. 16, 2024, as Appl. No. 18/774,846.
Application 18/447,990 is a division of application No. 17/990,629, filed on Nov. 18, 2022, granted, now 11,744,873, issued on Sep. 5, 2023.
Application 18/774,846 is a continuation of application No. 18/447,990, filed on Aug. 10, 2023.
Application 17/990,629 is a continuation of application No. PCT/US2022/012807, filed on Jan. 18, 2022.
Claims priority of provisional application 63/139,676, filed on Jan. 20, 2021.
Prior Publication US 2024/0366714 A1, Nov. 7, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 38/16 (2006.01); A61P 43/00 (2006.01)
CPC A61K 38/16 (2013.01) [A61P 43/00 (2018.01)] 22 Claims
 
1. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound, or a pharmaceutically acceptable salt thereof, to a subject in need thereof, wherein the compound has the structure of formula I:

OG Complex Work Unit Chemistry
wherein:
“*” indicates a chiral carbon with “S” configuration or “R” configuration;
R1 is selected from the group consisting of —C(═O)(OZ1), —P(═O)(X)(Y) and a 5-10 membered heteroaryl containing 1-2 heteroatoms selected from N, O and S optionally substituted with 1-2 R7 independently selected from halogen, C1-6 alkyl, haloC1-6 alkyl, haloC1-6 alkoxy, —OR5, C3-10 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl and 5-10 membered heterocyclyl;
R2 is selected from the group consisting of —C(═O)(OZ2), —P(═O)(X)(Y) and a 5-10 membered heteroaryl containing 1-2 heteroatoms selected from N, O and S optionally substituted with 1-2 R7 independently selected from halogen, C1-6 alkyl, haloC1-6 alkyl, haloC1-6 alkoxy, —OR5, C3-10 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl and 5-10 membered heterocyclyl;
each R7 is independently selected from the group consisting of halogen, C1-6 alkyl, haloC1-6 alkyl, haloC1-6 alkoxy, C1-6 alkoxy, C3-10 cycloalkyl, C6-10 aryl, 5-10 membered heteroaryl and 5-10 membered heterocyclyl;
X and Y each are independently selected from the group consisting of —OR4, NR5R6, C1-6 alkyl and haloC1-6 alkyl;
each R4 is independently selected from the group consisting of hydrogen, C1-6 alkyl, haloC1-6 alkyl, C6-10 aryl and C6-10 aryl alkyl;
each R5 is independently hydrogen or C1-6 alkyl;
each R6 is independently hydrogen or C1-6 alkyl; and
Z1 and Z2 each are independently selected from the group consisting of hydrogen, C1-6 alkyl, haloC1-6 alkyl, C3-10 cycloalkyl, C6-10 aryl and (C6-10 aryl) C1-6 alkyl, wherein at least one of Z1 and Z2 is not hydrogen.