C - Chemistry – Metallurgy – 07 – J
Patent
C - Chemistry, Metallurgy
07
J
C07J 63/00 (2006.01) A61K 31/56 (2006.01) A61K 31/704 (2006.01) A61K 39/00 (2006.01) A61K 39/39 (2006.01) A61P 37/02 (2006.01) C07H 15/24 (2006.01)
Patent
CA 2290646
The present invention is directed to novel chemical compounds in which a lipophilic moiety such as a lipid, fatty acid, polyethylene glycol or terpene is covalently attached to a non-acylated or desacylated triterpene saponin via a carboxyl group present on the 3-O-glucuronic acid of the triterpene saponin. The attachment of a lipophile moiety to the 3-O-glucuronic acid of a saponin such as Quillaja desacylsaponin, lucyoside P, or saponin from Gypsophila, Saponaria and Acanthophyllum enhances their adjuvant effects on humoral and cell mediated immunity. Additionally, the attachment of a lipophile moiety to the 3-O-glucuronic acid residue of non- or des-acylsaponin yields a saponin analog that is easier to purify, less toxic, chemically more stable, and possesses equal or better adjuvant properties than the original saponin.
L'invention porte sur de nouveaux composés chimiques dans lesquels un fragment lipophile, tel qu'un lipide, un acide gras, du polyéthylène glycol ou du terpène, est lié par covalence à de la saponine triterpénique non acylée ou désacylée par l'intermédiaire d'un groupe carbonyle présent sur l'acide 3-O-glucuronique de la saponine triterpénique. La fixation d'un fragment lipophile à l'acide 3-O-glucuronique d'une saponine, telle que la Quillaja dés-acylsaponine, la lucyoside P, ou la saponine de la Gypsophila, de la Saponaria et de l'Acanthophyllum, renforce leurs effets d'adjuvants sur l'immunité induite par les humeurs et les cellules. De plus, la fixation d'un fragment lipophile au résidu acide 3-O-glucuronique de la non ou dés-acylsaponine donne un analogue de la saponine plus facile à purifier, moins toxique, plus stable chimiquement, et possédant des propriétés d'adjuvant égales ou supérieures à celles de la saponine originale.
Galenica Pharmaceuticals Inc.
Mbm Intellectual Property Law Llp
LandOfFree
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