US 12,390,434 B2
Compositions and methods for reducing immune intolerance and treating autoimmune disorders
Anas M. Fathallah, Wakefield, MA (US); Scott D. Larsen, Gobles, MI (US); and Abdulraouf Ramadan, Malden, MA (US)
Assigned to Lapix Therapeutics, Inc., Cambridge, MA (US)
Filed by LAPIX Therapeutics, Inc., Boston, MA (US)
Filed on May 9, 2024, as Appl. No. 18/659,715.
Application 18/659,715 is a division of application No. 18/168,128, filed on Feb. 13, 2023, granted, now 12,016,836.
Application 18/168,128 is a continuation of application No. 17/886,926, filed on Aug. 12, 2022, granted, now 11,648,225, issued on May 16, 2023.
Claims priority of provisional application 63/233,039, filed on Aug. 13, 2021.
Prior Publication US 2024/0299327 A1, Sep. 12, 2024
Int. Cl. A61K 31/198 (2006.01); A61K 9/00 (2006.01); A61K 9/08 (2006.01); A61K 31/357 (2006.01); A61K 31/4184 (2006.01); A61K 31/44 (2006.01); A61K 31/472 (2006.01); A61K 47/40 (2006.01); A61P 25/28 (2006.01); A61P 37/06 (2006.01); C07C 235/34 (2006.01); C07D 213/65 (2006.01); C07D 217/02 (2006.01); C07D 235/06 (2006.01); C07D 319/18 (2006.01)
CPC A61K 31/198 (2013.01) [A61K 9/0053 (2013.01); A61K 9/08 (2013.01); A61K 31/357 (2013.01); A61K 31/4184 (2013.01); A61K 31/44 (2013.01); A61K 31/472 (2013.01); A61K 47/40 (2013.01); A61P 25/28 (2018.01); A61P 37/06 (2018.01); C07C 235/34 (2013.01); C07D 213/65 (2013.01); C07D 217/02 (2013.01); C07D 235/06 (2013.01); C07D 319/18 (2013.01)] 18 Claims
 
1. A method of treating an autoimmune disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of the following structural formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt of the foregoing, wherein:
Ring A is phenyl or (C5-C6)heteroaryl;
L is —(CH2)n—, —C(O)— or —C(OH)2—;
R1 is H or (C1-C5) alkyl;
each R2 is independently chloro or fluoro;
R3 is (C1-C3) alkyl substituted with one or more independently selected (C6-C15) aryl or (C5-C15) heteroaryl, wherein the (C6-C15) aryl and (C5-C15) heteroaryl are each independently substituted with —(R30)p;
each R30 is independently halo, (C1-C5) alkoxy, (C1-C5) haloalkoxy, (C1-C5) alkyl or (C1-C5) haloalkyl, or two R30 attached to adjacent ring atoms, taken together, form —(CH2)q— or —O(CH2)rO—;
n is 1, 2 or 3;
m is 0, 1, 2, 3 or 4;
each p is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
each q is independently 3, 4, 5 or 6; and
each r is independently 1, 2, 3 or 4.