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US 7,407,947 B2Granted
Amphoteric sterols and the use thereof
AssigneeNovosom AG
InventorsSteffen Panzner, Gerold Endert, Stefan Fankhaenel, Nasr El-Mokdad
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Abstract
An amphoteric compound based on a sterol skeleton, the 3-position of the sterol ring system being substituted by one or more amphoteric groups having an isoelectric point of between about 4 and 9, together with liposomes containing such compounds and their uses.
Claims24
A sterol derivative according to formula (1):
- Amphoteric substance -Y- spacer -X- sterol (1),
- wherein:
- said amphoteric substance comprises a first portion having a cationic charge with a pKa value between about 4 and about 8.5 and a second portion of anionic charge with a pKa value between about 3 and about 7;
- said first portion of said amphoteric substance is selected from the group consisting of piperazines, imidazoles, morpholines, purines, and pyrimidines;
- said second portion of said amphoteric substance comprises a carboxyl group;
- said spacer is a linear or branched C1-8 alkyl comprising 0-2 ethylenically unsaturated bonds;
- said linking group X is selected from the group consisting of —(C═O)—O—, —(C═O)—NH— and —NH—(C═O)—O—;
- said linking group Y is selected from the group consisting of —O—(C═O), —NH—(C═O), —(C═O)—O— and —(C═O)—NH—;
- said sterol is selected from the group consisting of cholesterol, sitosterol, campesterol, desmosterol, fucosterol, 22-ketosterol, 20-hydroxysterol, stigmasterol, 22-hydroxycholesterol, 25 -hydroxycholesterol, lanosterol, 7-dehydrocholesterol, dihydrocholesterol, 19-hydroxycholesterol, 5α-cholest-7-en-3β-ol, 7-hydroxycholesterol, epicholesterol, ergosterol, and dehydroergosterol;
- and
- said sterol derivative has an isoelectric point between about 4.5 and about 8.5.
8 more elements
Dependencies are inferred from the claim text.