Compositions and methods useful in administering nucleic acid based therapies, for example association complexes such as liposomes and lipoplexes are described.

Disclosed herein are polyketone triglyceride compositions containing 8 to 16 ketone carbonyl moieties per triglyceride unit and methods of making. Also disclosed are polyimine triglyceride compositions having has 8 to 16 nitrogen moieties per triglyceride unit and methods of making. Also disclosed are polyamine triglyceride compositions containing 8 to 16 nitrogen moieties per triglyceride unit and methods of making.

Amines and amine derivatives that improve the buffering range, and/or reduce the chelation and other negative interactions of the buffer and the system to be buffered. The reaction of amines or polyamines with various molecules to form polyamines with differing pKa's will extend the buffering range, derivatives that result in polyamines that have the same pKa yields a greater buffering capacity. Derivatives that result in zwitterionic buffers improve yield by allowing a greater range of stability.

Amines and amine derivatives that improve the buffering range, and/or reduce the chelation and other negative interactions of the buffer and the system to be buffered. The reaction of amines or polyamines with various molecules to form polyamines with differing pKa's will extend the buffering range, derivatives that result in polyamines that have the same pKa yields a greater buffering capacity. Derivatives that result in zwitterionic buffers improve yield by allowing a greater range of stability.

This invention provides for a compound of formula (I), or a pharmaceutically acceptable salt thereof, wherein R.sup.A, R.sup.B, R.sub.2 and R.sub.4 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.

##STR00001##

This invention provides for a compound of formula (I), or a pharmaceutically acceptable salt thereof, wherein R.sup.A, R.sup.B, R.sub.2 and R.sub.4 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.

##STR00001##

The present invention provides a method for producing a high quality cationic surfactant, which is prevented from smelling and coloring, and has favorable storage stability.

The production method includes the following step 1, step 2, step 3, and step 4: step 1: a step of obtaining an alkanolamine ester by reacting an alkanolamine with a fatty acid or a fatty acid alkyl ester without using hypophosphoric acid or a salt thereof; step 2: a step of obtaining a cationic surfactant by quaternizing the alkanolamine ester obtained in the step 1 with a dialkyl sulfate; step 3: a step of performing an oxidation treatment of the cationic surfactant obtained in the step 2; and step 4: a step of performing a reduction treatment of the cationic surfactant subjected to the oxidation treatment obtained in the step 3.

The present invention provides a method for producing a high quality cationic surfactant, which is prevented from smelling and coloring, and has favorable storage stability.

The production method includes the following step 1, step 2, step 3, and step 4: step 1: a step of obtaining an alkanolamine ester by reacting an alkanolamine with a fatty acid or a fatty acid alkyl ester without using hypophosphoric acid or a salt thereof; step 2: a step of obtaining a cationic surfactant by quaternizing the alkanolamine ester obtained in the step 1 with a dialkyl sulfate; step 3: a step of performing an oxidation treatment of the cationic surfactant obtained in the step 2; and step 4: a step of performing a reduction treatment of the cationic surfactant subjected to the oxidation treatment obtained in the step 3.

The present invention provides compositions and methods for stimulating an immune response using cationic lipids alone or in combination with antigens.

The present invention provides compositions and methods for stimulating an immune response using cationic lipids alone or in combination with antigens.