US 12,391,673 B2
LANCL ligands
Josep Bassaganya-Riera, Blacksburg, VA (US); Andrew Leber, Blacksburg, VA (US); and Raquel Hontecillas, Blacksburg, VA (US)
Assigned to NImmune Biopharma, Inc., Blacksburg, VA (US)
Filed by NImmune Biopharma, Inc., Blacksburg, VA (US)
Filed on Aug. 22, 2022, as Appl. No. 17/892,463.
Application 17/892,463 is a continuation of application No. 17/506,453, filed on Oct. 20, 2021, granted, now 11,459,310.
Claims priority of provisional application 63/104,109, filed on Oct. 22, 2020.
Prior Publication US 2023/0167083 A1, Jun. 1, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/14 (2006.01); A61P 1/00 (2006.01); A61P 1/16 (2006.01); A61P 3/04 (2006.01); A61P 3/10 (2006.01); A61P 17/06 (2006.01); A61P 19/02 (2006.01); A61P 37/06 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/14 (2013.01) [A61P 1/00 (2018.01); A61P 1/16 (2018.01); A61P 3/04 (2018.01); A61P 3/10 (2018.01); A61P 17/06 (2018.01); A61P 19/02 (2018.01); A61P 37/06 (2018.01); C07D 413/14 (2013.01)] 26 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a salt or ester thereof, wherein:
A1 and A6 are each C;
A8 and A11 are each N;
A10, A12, A13, A20, A21, A22, A23, and A24 are each C(R2);
A14 and A15 are each C(O) or N(RL), with the proviso that A14 and A15 are not both C(O) and are not both N(RL);
A16, A17, A18, and A19 are each independently selected from O, N(R2), S, N, and C(R2), with the provisos that:
A17 is N, A18 is N(R2), or A17 is N and A18 is N(R2); and
one and only one of A16, A17, A18, and A19 is O, N(R2), or S;
A2, A3, A4, A5, A7, A9 are each independently Nor C(R2);
--- represents delocalized pi bonds;
R1 is hydroxyl or optionally substituted alkyloxy;
R2 and RL in each instance are independently hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, hydroxyl, carboxyl, optionally substituted alkyloxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted cycloalkyloxy, optionally substituted cycloalkenyloxy, thiol, optionally substituted alkylthio, optionally substituted alkenylthio, optionally substituted alkynylthio, optionally substituted alkylsulfinyl, optionally substituted alkylsulfonyl, optionally substituted alkylsulfonyloxy, optionally substituted cycloalkylthio, optionally substituted cycloalkylsulfinyl, optionally substituted cycloalkylsulfonyl, optionally substituted cycloalkylsulfonyloxy, optionally substituted cycloalkenylthio, optionally substituted cycloalkenylsulfinyl, optionally substituted cycloalkenylsulfonyl, optionally substituted cycloalkenylsulfonyloxy, optionally substituted amino, acyl, optionally substituted alkyloxycarbonyl, optionally substituted alkenyloxycarbonyl, optionally substituted alkynyloxycarbonyl, optionally substituted aryloxycarbonyl, optionally substituted carbamoyl, optionally substituted sulfamoyl, cyano, nitro, optionally substituted aryl, optionally substituted aryloxy, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl, optionally substituted arylsulfonyloxy, optionally substituted heteroaryl, optionally substituted heteroaryloxy, optionally substituted heteroarylthio, optionally substituted heteroarylsulfinyl, optionally substituted heteroarylsulfonyl, optionally substituted heteroarylsulfonyloxy, or an optionally substituted non-aromatic heterocyclic group.