Sphingoglycolipid analogues

Disclosed herein are sphingoglycolipid analogues of formulas I, II, IV or V and formulations and uses thereof. The compounds are immune stimulators having a similar in vivo activity compared to α-GalCer with regard to activation of Invariant natural killer T cells (NKT). The compounds of the disclos...

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Hauptverfasser: ANDERSON REGAN JAMES, HAYMAN COLIN MALCOLM, PAINTER GAVIN FRANK, COMPTON BENJAMIN JASON, HERMANS IAN FRANCIS, LARSEN DAVID SAMUEL, JOHNSTON KAREN ANNE
Format: Patent
Sprache:eng
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Zusammenfassung:Disclosed herein are sphingoglycolipid analogues of formulas I, II, IV or V and formulations and uses thereof. The compounds are immune stimulators having a similar in vivo activity compared to α-GalCer with regard to activation of Invariant natural killer T cells (NKT). The compounds of the disclosure may be used to treat or prevent an infectious disease, an atopic disorder, an autoimmune disease, diabetes or cancer. Specific compounds of the disclosure include: Methyl 1-(((2S,3S,4R)-1-(6-Deoxy-)-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-dihydroxyoctadecandyl)-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74-tetracosaoxa-1,2-dithiaoctaheptacontan-77-oate, (2S,3S,4R)-1-(6-Deoxy-6-(N-ethylmaleimid-3-yl)thio)-α-Dgalactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol,2S,3S,4R)-1-(6-Deoxy-6-((4-iodo-N-(5-azidopentyl)-maleimid-3-yl)thio)-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol, (2S,3S,4R)-1-O-[6-Deoxy-6-(2-pyridyl)disulfanyl]-α-Dgalactopyranosyl)-2-hexacosanoylamino-3,4-octadecandiol, (2S,3S,4R)-1-(6-Deoxy-6-napthalen-2-ylthio-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol, (2S,3S,4R)-1-(6-Deoxy-6- ethylsulfinyl)-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol, and (2S,3S,4R)-1-(4,6-Anhydro-α-D-galactopyranosyloxy)-2-hexacosanoylamino-3,4-octadecandiol.