US 12,091,402 B2
Potent ASGPR-binding compounds for the degradation of immunoglobulins and other proteins
Jason Allan Wiles, Madison, CT (US); Srinivasa Karra, Pembrooke, MA (US); Mark George Saulnier, Higganum, CT (US); Jesse Jingyang Chen, Lexington, MA (US); Kevin Tyler Sprott, Needham, MA (US); and Soumya Ray, Quincy, MA (US)
Assigned to Avilar Therapeutics, Inc., Waltham, MA (US)
Filed by Avilar Therapeutics, Inc., Waltham, MA (US)
Filed on Jul. 11, 2023, as Appl. No. 18/220,737.
Application 18/220,737 is a continuation of application No. PCT/US2022/027513, filed on May 3, 2022.
Claims priority of provisional application 63/331,592, filed on Apr. 15, 2022.
Claims priority of provisional application 63/293,447, filed on Dec. 23, 2021.
Claims priority of provisional application 63/228,067, filed on Jul. 31, 2021.
Claims priority of provisional application 63/183,450, filed on May 3, 2021.
Prior Publication US 2024/0101539 A1, Mar. 28, 2024
Int. Cl. C07D 405/12 (2006.01); C07D 405/14 (2006.01); C07D 417/12 (2006.01); C07H 17/00 (2006.01); C07H 17/02 (2006.01)
CPC C07D 405/12 (2013.01) [C07D 405/14 (2013.01); C07D 417/12 (2013.01); C07H 17/00 (2013.01); C07H 17/02 (2013.01)] 29 Claims
 
1. A compound of formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof;
wherein:
R1 and R5 are independently selected from hydrogen, C0-C6alkyl-cyano, alkyl, alkenyl, alkynyl, haloalkyl, F, Cl, Br, I, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycle, heterocycloalkyl, haloalkoxy, C0-C6alkyl-OR6, C0-C6alkyl-SR6, C0-C6alkyl-NR6R7, C0-C6alkyl-C(O)R3, C0-C6alkyl-S(O)R3, C0-C6alkyl-S(O)2R3, C0-C6alkyl-N(R8)—C(O)R3, C0-C6alkyl-O—C(O)R3, C0-C6alkylN3, and C0-C6alkyl-O—S(O)2R3;
R3 at each occurrence is independently selected from hydrogen, alkyl, haloalkyl, arylalkyl, heteroarylalkyl, alkynyl, aryl, heteroaryl, heterocycle, —OR8, and —NR8R9;
R6 and R7 are independently selected at each occurrence from hydrogen, alkyl, arylalkyl, heteroarylalkyl, alkynyl, aryl, haloalkyl, heteroaryl, heterocycle, -alkyl-OR8, and C(O)R3;
R8 and R9 are independently selected at each occurrence from hydrogen, heteroalkyl, alkyl, arylalkyl, heteroarylalkyl, alkenyl, alkynyl, aryl, heteroaryl, and heterocycle;
R10 is selected from hydrogen, alkyl, arylalkyl, heteroarylalkyl, aryl, heteroaryl, and heterocycle;
R65, R66, and R67 are independently selected from hydrogen, C0-C6alkyl-cyano, alkyl, haloalkyl, F, Cl, Br, I, C0-C6alkyl-OR6, C0-C6alkyl-NR6R7, C0-C6alkyl-C(O)R3, and C0-C6alkylN3;
R68, R69, and R70 are independently selected from hydrogen, alkyl, F, Cl, Br, I, C0-C6alkyl-OR6, C0-C6alkyl-NR6R7, C0-C6alkyl-C(O)R3, C0-C6alkyl-S(O)R3, C0-C6alkyl-N(R8)—C(O)R3, C0-C6alkylN3, heteroaryl, and aryl.