Amine Cationic Lipids and Uses Thereof

A compound having the formula:

• or a pharmaceutically acceptable salt thereof,
• wherein
• each R1 and R2 is, independently, optionally substituted C11-24 alkyl, optionally substituted C11-24 alkenyl, optionally substituted C11-24 alkynyl, optionally substituted C11-24 heteroalkyl, optionally substituted C11-24 heteroalkenyl, or optionally substituted C11-24 heteroalkynyl, wherein said R1 and R2 is not substituted with an oxo on the carbon adjacent to >CHNR3R4;
• R3 is H or optionally substituted C1-6 alkyl;
• and
• R4 is unsubstituted C1-6 alkyl that is substituted with —NR4aR4b, substituted C1-6 alkyl that is further substituted with —NR4aR4b, or optionally substituted C3-7 heterocyclyl, wherein each R4a and R4b is, independently, H, C(═NH)NH2, or optionally substituted C1-6 alkyl, or wherein R4a and R4b combine together to form optionally substituted C3-7 heterocyclyl;
• or
• R3 and R4 combine together to form an optionally substituted C3-7 heterocyclyl, or
• R3 and R4 do not combine together and form optionally substituted imidazolyl or optionally substituted benzimidazolyl or optionally substituted succinimidyl;
• wherein one, and only one, primary amine can be present on either R3 or R4 or no primary amine is present on either R3 or R4;
• and wherein neither R3 nor R4 is an optionally substituted amide;
• and wherein when R1 or R2 is saturated C11 alkyl or saturated C15 alkyl, R3 is not H;
• wherein when R1 or R2 is saturated C16 alkyl or saturated C17 alkyl, R1 and R2 is not substituted with hydroxy;
• wherein when R1 or R2 is saturated C17 alkyl, R3 or R4 is not substituted with hydroxy;
• and
• wherein when R1 or R2 is saturated C18 alkyl, R4 is not substituted with optionally substituted imidazolyl.