Disaccharide Synthetic Lipid Compounds and Uses Thereof

摘要

Essentially pure compounds of the formulas (I) to (XXV) are provided. Compositions and methods for enhancing or stimulating an immune response are also provided. The compounds, provided are advantageous in that the compounds are essentially pure and free from contaminants encountered when such compounds are purified from natural sources.

主权项

1. An essentially pure compound having the structure: or a pharmaceutically acceptable salt or prodrug thereof, wherein: X1, X2, X3, X4 and X5 are each independently selected from —O—, —NH— or —CH2—; Y1, Y2, Y3, Y4 and Y5 are each independently selected from H, C1-C4 alkyl, —CH2— or —C(═O)—, provided that at least 3 of Y1, Y2, Y3, Y4 and Y5 are a group other than H or C1-C4 alkyl and further provided that when one of Y1, Y2, Y3, Y4 and Y5 is H, then the groups which are linked, directly or indirectly, to the Y1, Y2, Y3, Y4 or Y5 are absent; D, E, G and F are each independently selected from —OH, —SH, —OC(═O)(CH2)m—CH3, OC(═O)(CH2)nC(═O)OH, —OC(═O)CH(NH2)(CH2)nC(═O)OH or —OC(═O)CH2CH(OH)(CH2)nCH3; J and B are each independently selected from OH, OR1, H, —OP(═O)(OH)2—, OP(═O)(OR2)2—, —OS(═O)(OH)2—, —OS(═O)(OR2)2—, —OS(OH)2—, —OS(OR2)2—, —C(═O)OH—, —C(═O)OR2— or an acidic group; A1, A2, and A4 are each independently selected from C6 to C18 substituted or unsubstituted alkyl or alkenyl; A3 and A5 are each independently selected from C7 to C19 substituted or unsubstituted alkyl or alkenyl; R1 is a substituted or unsubstituted C1-C4 alkyl; R2 is independently for each occurrence, H, alkyl, substituted alkyl or N-linked amino acid residue; and m and n are each independently an integer from 0 to 5.