Analogs of alpha galactosyceramide and uses thereof

Abstract

There are disclosed compound of formula I, in which Rrepresents a hydrophobic moiety adapted to occupy the C' channel of human CDId, Rrepresents a hydrophobic moiety adapted to occupy the A′ channel of human CDId, such that Rfills at least at least 30% of the occupied volume of the C′ channel compared to the volume occupied by the terminal nCHof the sphingosine chain of α-galactosylceramide when bound to human CDId and Rfills at least 30% of the occupied volume of the A′ channel compared to the volume occupied by the terminal nCHof the acyl chain of α-galactosylceramide when bound to human CDId Rrepresents hydrogen or OH, Rand Reach represent hydrogen and in addition, when Rrepresents hydrogen, Rand Rtogether may form a single bond, X represents or —CHA(CHOH)Y or —P(=0)(0)0CH(CH0H)Y, in which Y represents CHBB, n represents an integer from 1 to 4, m represents 0 or 1, A årepresents hydrogen, one of Band Brepresents H, OH or phenyl, and the other represents hydrogen or one of Band Brepresents hydroxyl and the other represents phenyl, in addition, when n represents 4, then A together with one of Band Btogether forms a single bond and the other of Band Brepresents H, OH or OSOH and pharmaceutically acceptable salts thereof; the compounds of formula I are indicted for use in the treatment of a virus, microbial infection, parasite, an autoimmune disease, cancer, allergy or asthma.