Compounds and compositions for intracellular delivery of therapeutic agents

A compound of Formula (I):

• or salts or isomers thereof, wherein:
• R1 is —R″M′R′ or C5-20 alkenyl;
• R2 and R3 are each independently selected from C1-14 alkyl and C2-14 alkenyl;
• R4 is —(CH2)nQ, wherein Q is OH and n is selected from 1, 2, 3, 4, and 5;
• M and M′ are each independently —C(O)O— or —OC(O)—;
• R5, R6, and R7 are each H;
• R′ is a linear C1-12 alkyl, or C1-12 alkyl substituted with C6-9 alkyl;
• R″ is C6-14 alkyl;
• m is selected from 6, 7, 8, 9, 10, 11, 12, and 13.

A compound of Formula (IA):

• or a salt or isomer thereof, wherein
• l is selected from 1, 2, 3, 4, and 5;
• m is selected from 5, 6, 7, 8, and 9;
• M1 is a bond or M′;
• R4 is unsubstituted C1-3 alkyl, or —(CH2)nQ, in which Q is OH, —NHC(S)N(R)2, —NHC(O)N(R)2, —N(R)C(O)R, —N(R)S(O)2R, —N(R)R8, —NHC(═NR9)N(R)2, —NHC(═CHR9)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(═NR9)N(R)2, —N(OR)C(═CHR9)N(R)2, or heteroaryl, and each n is selected from 1, 2, 3, 4, or 5;
• M and M′ are independently selected
• from —C(O)O—, —OC(O)—, —C(O)N(R′)-, —P(O)(OR′)O-,
• —S—S—, an aryl group, and a heteroaryl group;
• and
• R2 and R3 are both C1-14 alkyl, or C2-14 alkenyl;
• R8 is selected from the group consisting of C3-6 carbocycle and heterocycle;
• R9 is selected from the group consisting of H, CN, NO2, C1-6 alkyl, —OR, —S(O)2R, —S(O)2N(R)2, C2-6 alkenyl, C3-6 carbocycle and heterocycle;
• each R is independently selected from the group consisting of C1-3 alkyl, C2-3 alkenyl, and H;
• and
• R′ is a linear alkenyl.