Lipid compounds and lipid nanoparticle compositions

A compound of Formula (III):

• or a pharmaceutically acceptable salt, prodrug or stereoisomer thereof, wherein:
• R1 and R2 are each independently C5-C32 alkyl or C5-C32 alkenyl;
• R0 is C1-C12 alkyl, C2-C12 alkenyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C6-C10 aryl, or 4- to 8-membered heterocycloalkyl;
• G3 is C2-C12 alkylene or C2-C12 alkenylene;
• G4 is C2-C12 alkylene or C2-C12 alkenylene;
• R3 is-N(R4) R5 or —OR6;
• R4 is C1-C12 alkyl, C2-C12 alkenyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C6-C10 aryl, or 4- to 8-membered heterocycloalkyl;
• R5 is C1-C12 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C6-C10 aryl, 4- to 8-membered heterocycloalkyl, —(CH2)nQ, —(CH2)nCHQR, -CHQR, or -CQ(R)2, wherein Q is C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkynyl, 4- to 8-membered heterocyclyl, C6-C10 aryl, 5- to 10-membered heteroaryl, —OR, —O(CH2)pN(R)2, —C(O)OR, —OC(O)R, —CX3, —CX2H, —CXH2, —CN, —N(R)2, —C(O)N(R)2, —N(R)C(O)R, —N(R)S(O)2R, —N(R)C(O)N(R)2, —N(R)C(S)N(R)2, —N(R) R22, —O(CH2)pOR, —N(R)C(═NR23)N(R)2, —N(R)C(═CHR23)N(R)2, —OC(O)N(R)2, —N(R)C(O)OR, —N(OR)C(O)R, —N(OR)S(O)2R, —N(OR)C(O)OR, —N(OR)C(O)N(R)2, —N(OR)C(S)N(R)2, —N(OR)C(═NR23)N(R)2, —N(OR)C(═CHR23)N(R)2, —C(═NR23)N(R)2, —C(═NR23)R, —C(O)N(R)OR, or —C(R)N(R)2C(O)OR, and each p is independently 1, 2, 3, 4, or 5;
• R22 is C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkynyl, 4- to 8-membered heterocyclyl, C6-C10 aryl, or 5- to 10-membered heteroaryl;
• R23 is H, —CN, —NO2, C1-C6 alkyl, —OR, —S(O)2R, —S(O)2N(R)2, C2-C6 alkenyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkynyl, 4- to 8-membered heterocyclyl, C6-C10 aryl, or 5- to 10-membered heteroaryl;
• each R is independently H, C1-C3 alkyl, or C2-C3 alkenyl;
• or two R in a N(R)2 moiety together with the nitrogen to which they are attached form a cyclic moiety;
• and
• each X is independently F, Cl, Br, or I;
• or R4, R5, together with the nitrogen to which they are attached form a cyclic moiety;
• R6 is hydrogen, C1-C12 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C6-C10 aryl;
• and
• wherein, unless otherwise specified, each alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, heterocycloalkyl, aryl, heteroaryl, alkylene, alkenylene, and cyclic moiety is unsubstituted.