Ionizable lipids and compositions for nucleic acid delivery

A compound of Formula (I-1):

• or a pharmaceutically acceptable salt thereof, wherein
• m1, m2, m3, and m4 are the same, all of which are 1, 2, 3, 4, or 5;
• L1, L2, L3, and L4 are the same, all of which are selected from —CH(OH)—, —C(═O)—, {circumflex over ( )}—C(═O)O—{circumflex over ( )}{circumflex over ( )}, {circumflex over ( )}—OC(═O)—{circumflex over ( )}{circumflex over ( )}, {circumflex over ( )}—C(═O)NRa—{circumflex over ( )}{circumflex over ( )}, {circumflex over ( )}—NRaC(═O)—{circumflex over ( )}{circumflex over ( )}, or absent, wherein
• {circumflex over ( )}— represents the point which attaches to R1-4;
• —{circumflex over ( )}{circumflex over ( )}represents the point which attaches to —(CH2)m1-m4—;
• and
• each Ra is independently —H or optionally substituted C1-C6 alkyl;
• R1, R2, R3, and R4 are the same, all of which are selected from optionally substituted C6-C18 alkyl, or optionally substituted C6-C18 alkenyl;
• G1 and G2 are the same, and G3 and G4 are the same, when G1 and G2 are —Rc—, G3 and G4 are selected from —Rc—, *—RcC(═O)Rd—**, *—RcC(═O)ORd—**, *—RcOC(═O)Rd—**, *—RcC(═O)N(Rb)Rd—**, *—RN(Rb)C(═O)Rd—**, or absent;
• wherein
• *— represents the point which attaches to the —CH2— group next to the terminal tertiary amine atom as shown in Formula (I-1);
• —** represents the point which attaches to the —CH2— group next to the middle tertiary amine atom as shown in Formula (I-1);
• when G3 and G4 are —Rc—, G1 and G2 are selected from —Rc—, #—RcC(═O)Rd—##, #—RcC(═O)ORd—##, #—RcOC(═O)Rd—##, #—RcC(═O)N(Rb)Rd—##, #—RN(Rb)C(═O)Rd-##, #—RcN(Rb)C(═O)ORd—##, #—RcOC(═O)N(Rb)Rd—##, or absent;
• wherein
• #— represents the point which attaches to the —CH2— group next to the middle tertiary amine atom as shown in Formula (1-1);
• —## represents the point connecting G1 and G2;
• and
• 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 the same, both of which are selected from-H or optionally substituted C1-C4 alkyl.