Lipids and lipid compositions for the delivery of active agents

A compound according to formula (I):

• wherein:
• L is C1-6 alkylene, C2-6 alkenylene, C2-6 alkynylene, —(CH2)r—C3-7 cycloalkylene-(CH2)s—, —(CH2)s—C3-7 cycloalkenylene-(CH2)s—, —(CH2)s—C3-7 cycloalkynylene-(CH2)s—,
• *—C1-4 alkylene-L2-, *—C1-4 alkylene-L2-C1-4 alkylene-,
• wherein in the * denotes attachment of the moiety to the NR1R2 group;
• L2, attached in either direction, is —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —CONH—, S(O)2NH—, NHCONH— or —NHCSNH—;
• each s is independently 0, 1 or 2;
• each t is independently 0, 1, 2, 3, or 4;
• u is 0, 1, 2, 3, 4, 5, or 6;
• R1 and R2 are each independently optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C3-7 cycloalkyl-(CH2)s—, optionally substituted C3-7 cycloalkenyl-(CH2)s—, optionally substituted C3-7 cycloalkynyl-(CH2)s—, or optionally substituted phenyl-(CH2)s—;
• wherein said C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-7 cycloalkyl, C3-7 cycloalkenyl, C3-7 cycloalkynyl, and phenyl are optionally substituted with one or two substituents each independently selected from the group consisting of:
• OH, C1-3 alkoxy, COOH, and COO—C1-4 alkyl,
• or
• R1 and R2 are joined together forming an optionally substituted 4-12 membered heterocyclic ring, said heterocyclic ring being optionally substituted with one to three substituents each independently selected from the group consisting of:
• OH, halo, C1-3 alkyl, C1-3 alkoxy, dimethylamino, —OCO—C1-4 alkyl, phenyl, piperidinyl, and morpholinyl;
• R3 and R4 are each independently:
• (a) —Z1—Ra,
• (b) —Z1—Rb—Z2—Ra,
• (c) —Z1—Rb—Z2—Rb—Z3—Ra,
• (d) —Z1—Rb—Z2—Rb—Z3—Rb—Z4—Ra,
• (e) —Rb—Z1—Ra,
• (f) —Rb—Z1—Rb—Z2—Ra,
• (g) —Rb—Z1—Rb—Z2—Rb—Z3—Ra,
• (h) —Rb—Z1—Rb—Z2—Rb—Z3—Rb—Z4—Ra,
• (i) —Rc,
• (j) —Z1—Rb—Rc, or
• (k) —Rb—Z1—Rb—Rc;
• wherein Z1, Z2, Z3, and Z4, attached in either direction, are each independently —O—, —C(O)O—, —OC(O)O—, or —CONH—;
• Ra is C2-22 alkyl, C2-22 alkenyl, or C2-22 alkynyl;
• each Rb is independently C1-20 alkylene, C2-20 alkenylene, or C2-20 alkynylene;
• Rc is
• R is C5-22 alkyl, C5-22 alkenyl, or C5-22 alkynyl;
• n is 0-12;
• m, p, and q are each independently 0, 1, 2, 3 or 4;
• provided that chains (a)-(h) have 12-30 carbon atoms and chains (i)-(k) have 12-70 carbon atoms;
• X is CR6 or N;
• and
• R6 is H, halo, C1-6 alkyl, or R4;
• or a pharmaceutically acceptable salt thereof.