US 11,839,657 B2
Ionizable lipids and compositions for nucleic acid delivery
Xiangrong Song, Chengdu (CN); Xiawei Wei, Chengdu Tianfu International Bio-Town (CN); and Yuquan Wei, Chengdu Tianfu International Bio-Town (CN)
Assigned to WESTGENE BIOPHARMA CO., LTD, Chengdu (CN)
Filed by WESTGENE BIOPHARMA CO., LTD, Chengdu (CN)
Filed on Mar. 3, 2023, as Appl. No. 18/117,049.
Application 18/117,049 is a continuation of application No. PCT/CN2022/086310, filed on Apr. 12, 2022.
Claims priority of application No. 202110396368.4 (CN), filed on Apr. 13, 2021.
Prior Publication US 2023/0226192 A1, Jul. 20, 2023
Int. Cl. A61K 47/54 (2017.01); A61K 47/60 (2017.01); A61K 9/51 (2006.01); A61K 39/215 (2006.01); A61K 47/24 (2006.01); A61K 47/28 (2006.01); C07C 229/12 (2006.01); C07C 237/06 (2006.01); C07C 271/20 (2006.01); C07C 323/25 (2006.01); A61K 39/00 (2006.01)
CPC A61K 47/543 (2017.08) [A61K 9/5123 (2013.01); A61K 39/215 (2013.01); A61K 47/24 (2013.01); A61K 47/28 (2013.01); A61K 47/60 (2017.08); C07C 229/12 (2013.01); C07C 237/06 (2013.01); C07C 271/20 (2013.01); C07C 323/25 (2013.01); A61K 2039/6018 (2013.01)] 24 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
m1, m2, m3, and m4 are each independently selected from 1, 2, 3, 4, or 5;
L1, L2, L3, and L4 are each independently selected from —CH(OH)—, —C(═O)—, —C(═O)O—, —OC(═O)—, —C(═O)S—, —SC(═O)—, —C(═O)NRa—, —NRaC(═O)—, —NRaC(═O)O—, —OC(═O)NRa—, —O—, —O—O—, —S—, —S—S—, —S—S—S—, —CH(OH)CH2O—, —CH(OH)CH2S—, or absent, wherein
each Ra is independently —H or optionally substituted C1-C6 alkyl;
R1, R2, R3, and R4 are each independently selected from optionally substituted C6-C30 alkyl, optionally substituted C6-C30 alkenyl, or optionally substituted C6-C30 alkynyl;
G1, G2, G3 and G4 are each independently selected from —Rc—, —RcCH(OH)Rd—, —RcC(═O)Rd—, —RcC(═O)ORd—, —RcOC(═O)Rd—, —RcC(═O)SRd—, —RcSC(═O)Rd—, —RcC(═O)N(Rb)Rd—, —RcN(Rb)C(═O)Rd—, —RcN(Rb)C(═O)ORd—, —RcOC(═O)N(Rb)Rd—, —RcORd—, —Rc—O—O—Rd—, —RcSRd—, —Rc—S—S—Rd—, —Rc—S—S—S—Rd—, or absent; wherein
each Rb is independently —H or optionally substituted C1-C6 alkyl;
each Rc and Rd are independently —(CH2)n—, and n is 0, 1, 2, 3, or 4;
R5 and R6 are each independently selected from —H, —OH, or optionally substituted C1-C6 alkyl.