US 12,258,332 B2
ASGPR cell surface receptor binding compounds and conjugates
Brett Bradley Busch, San Diego, CA (US); Justin Thomas Ernst, San Diego, CA (US); Garrick K. Packard, San Diego, CA (US); Jason G. Lewis, Castro Valley, CA (US); and Eric D. Turtle, Belmont, CA (US)
Assigned to Lycia Therapeutics, Inc., South San Francisco, CA (US)
Filed by Lycia Therapeutics, Inc., South San Francisco, CA (US)
Filed on Apr. 14, 2023, as Appl. No. 18/301,025.
Application 18/301,025 is a continuation of application No. PCT/US2022/037227, filed on Jul. 14, 2022.
Claims priority of provisional application 63/221,918, filed on Jul. 14, 2021.
Prior Publication US 2023/0250091 A1, Aug. 10, 2023
Int. Cl. C07D 405/04 (2006.01); C07D 405/12 (2006.01); C07D 405/14 (2006.01); C07D 493/08 (2006.01)
CPC C07D 405/04 (2013.01) [C07D 405/12 (2013.01); C07D 405/14 (2013.01); C07D 493/08 (2013.01)] 18 Claims
 
1. A compound of formula (I):
Xn-L-Y   (I)
or a prodrug thereof, or a salt thereof,
wherein:
Y is an antibody or antibody fragment that binds a target protein;
n is 1 to 500;
L is a linker; and
X is a moiety that binds to a cell surface asialoglycoprotein receptor (ASGPR) of formula:

OG Complex Work Unit Chemistry
wherein:
R1 is selected from —OH, —OC(O)R, —C(O)NHR, and triazole, where R is C1-6 alkyl or aryl;
R2 is selected from —NHCOCH3, —NHCOCF3, —NHCOCH2CF3, —OH, and triazole;
wherein “*” represents a point of attachment of Z1 to the linker (L);
R4 and R5 are H;
each Z1 is a linking moiety selected from Z11, Z11-heteroaryl, Z11-aryl, and alkyl;
Z11 is —C(R22)2—; and
each R22 is independently selected from H, halogen, and (C1-C6) alkyl.