US 12,257,243 B2
5-hydroxy-7-oxabicyclo[2.2.1]heptane-2-carboxamide derivatives for inducing chondrogenesis for treating joint damage
James Paul Lajiness, San Diego, CA (US); and Andrew Valiere, Descanso, CA (US)
Assigned to NOVARTIS AG, Basel (CH)
Appl. No. 17/299,189
Filed by NOVARTIS AG, Basel (CH)
PCT Filed Dec. 4, 2019, PCT No. PCT/IB2019/060454
§ 371(c)(1), (2) Date Jun. 2, 2021,
PCT Pub. No. WO2020/115683, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/776,267, filed on Dec. 6, 2018.
Prior Publication US 2022/0071972 A1, Mar. 10, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/443 (2006.01); A61K 31/343 (2006.01); A61K 45/06 (2006.01); C07D 493/08 (2006.01)
CPC A61K 31/443 (2013.01) [A61K 31/343 (2013.01); A61K 45/06 (2013.01); C07D 493/08 (2013.01)] 22 Claims
 
1. A compound of Formula (1):

OG Complex Work Unit Chemistry
or an enantiomer, an enantiomeric mixture thereof or a pharmaceutically acceptable salt thereof; wherein
W is phenyl or pyridyl;
R1 is hydrogen or C1-6alkyl;
R2 is phenyl or a 5-6 membered heteroaryl having 1-2 heteroatoms selected from N, O and S; wherein R2 is substituted by 1-2 substituents independently selected from halo, C1-6 alkyl, C1-6 haloalkyl or C1-6 alkoxy;
R3 is independently selected from halo, cyano, C1-6alkyl, C1-6haloalkyl, C1-6alkoxy, C3-6 cycloalkyl and 5-6 membered heterocyclyl; and
n is 0-2;
provided said compound is not (1R,2R,3S,4R,5S)-5-hydroxy-3-(2-methylpyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)-7-oxabicyclo[2.2.1]heptane-2-carboxamide; or an enantiomer, enantiomeric mixture or a pharmaceutically acceptable salt thereof.