Carbonyl lipids and lipid nanoparticle formulations for delivery of nucleic acids

A compound having the following structure (II):

• or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
• L1 is —O(C═O)R1, —(C═O)OR1, —C(═O)R1, —OR1, —S(O)xR1, —S—SR1, —C(═O)SR1, —SC(═O)R1, —NRaC(═O)R1, —C(═O)NRbRc, —NRaC(═O)NRbRc, —OC(═O)NRbRc or —NRaC(═O)OR1;
• L2 is —O(C═O)R2, —(C═O)OR2, —C(═O)R2, —OR2, —S(O)xR2, —S—SR2, —C(═O)SR2, —SC(═O)R2, —NRdC(═O)R2, —C(═O)NReRf, —NRdC(═O)NReRf, —OC(═O)NReRf, —NRdC(═O)OR2, or a direct bond to R2;
• G1b and G2b are each independently C1-C12 alkylene or C2-C12 alkenylene;
• G3 is C1-C24 alkylene, C2-C24 alkenylene, C3-C8 cycloalkylene or C3-C8 cycloalkenylene;
• Ra, Rb, Rd and Re are each independently H, C1-C12 alkyl or C2-C12 alkenyl;
• Rc and Rf are each independently C1-C12 alkyl or C2-C12 alkenyl;
• R1 and R2 each, independently, have the following structure:
• wherein:
• R7a and R7b are, at each occurrence, independently H or C1-C12 alkyl;
• and
• a is an integer from 2 to 12,
• wherein R7a, R7b and a are each selected such that R1 and R2 are each independently branched and independently comprise from 6 to 20 carbon atoms;
• R3b is —NR4bC(═O)R5b;
• R4b is H, C1-C12 alkyl or C2-C12 alkenyl;
• R5b is C2-C12 alkyl or C2-C12 alkenyl when R4b is H;
• or R5b is C1-C12 alkyl or C2-C12 alkenyl when R4b is C1-C12 alkyl or C2-C12 alkenyl;
• and
• x is 0, 1 or 2, and
• wherein each alkyl, alkenyl, alkylene, alkenylene, cycloalkylene, cycloalkenylene, aryl and aralkyl is independently substituted or unsubstituted.