QS-21 adjuvant

US 5057540

expires 15 Oct 2008

Pure preparations of four different saponins from Q. saponaria and use of the saponins as adjuvants to enhance an immune response.

Substantially pure saponin purified from a crude Quillaja saponaria extract
wherein said pure saponin is characterized by a single predominant peak
which comprises 90% or more of the total area of all peaks of a chromatogram, excluding the solvent peak,
when analyzed on reverse phase-HPLC on a Vydac C4 column having 5 mu m particle size, 330.ANG. pore, 4.6 mm ID.times.25 cm L in a solvent of 40 mM acetic acid in methanol/water (58/42; v/v) at a flow rate of 1 ml/mixture, and
wherein said saponin has immune adjuvant activity and is less toxic when used as an adjuvant than said Quillaja saponaria extract.

US 5583112

expires 10 Dec 2013

Conjugates of saponin QS-21 and antigen, which are conjugated through a linker group.  Vaccines comprising the conjugates and uses of conjugates to enhance an immune response to the antigen.

A saponin/antigen covalent conjugate composition or a saponin alkaline hydrolysis product/antigen covalent conjugate composition comprising a substantially pure saponin selected from the group consisting of QA-21-V1 and QA-21-V2, or an alkaline hydrolysis product of a substantially pure saponin selected from the group consisting of QA-21-V1 and QA-21-V2, wherein said saponin or saponin alkaline hydrolysis product comprises a glucuronate carboxyl group, said saponin or said saponin alkaline hydrolysis product being linked at the glucuronate carboxyl group to an antigen either directly or through a linker group, wherein the linkage does not interfere with the ability of said substantially pure saponin or said alkaline hydrolysis product to stimulate an immune response in an animal.

EP 0 362 279 B

expired 31 May 2008

Pure preparations of three different saponins from Q. saponaria, pharmaceutical compositions comprising an antigen and one of the pure saponins.

A substantially pure saponin obtainable from a crude Quillaja saponaria extract, the saponin appearing as a peak on analysis of the extract by reverse phase-HPLC on a Vydac C4 column having 5 iim particle size, 330 A pore, 4.6mm ID x 25 cm L in a solvent of 40mM acetic acid in methanol/water (58/42; v/v) at a flow rate of 1 mI/minute, the saponin having immune adjuvant activity and being less toxic as an adjuvant that the Quillaja saponaria extract.

EP 0 606 317 B

expires 17 Sept 2012

Conjugates of one of four saponins with an antigen throug a bifunctional linker. Substantially pure QS-21 and saponins modified with an active chemical group.  Vaccines and pharmaceutical compositions.

A saponin/antigen covalent conjugate comprising a substantially pure saponin selected from QA-7, QA-17, QA-18, QA-21, QA-21-V1 and QA-21-V2, or an alkaline hydrolysis product thereof, which is linked to an antigen through a bifunctional linker group, wherein the linkage does not interfere with the ability of the substantially pure saponin or alkaline hydrolysis product to stimulate an immune response in an animal.