Analogs of alpha galactosyceramide and uses thereof

US8039670B2 · kind B2 · utility

Assignees

• LUDWIG INSTITUTE FOR CANCER RESEARCH LTD · GB
• Chancellor Master and Scholars of the University of Oxford · GB
• The University of Birmingham · GB

Inventors

• Vincenzo Cerundolo · Woodstock, GB
• Richard Schmidt · Konstanz, DE
• Gopal Reddy · Stony Brook, US
• Rengarajan Balamurugan · Hyderabad, IN
• Gerd Ritter · New York, US
• Gurdyal S. Besra · Birmingham, GB
• Mariolina Salio · Felton, GB
• Jonathan Silk · Felton, GB

Key dates

• Filing date: Oct 25, 2006
• Grant date: Oct 18, 2011
• Expiry date: Jan 5, 2028

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P37/08
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

There are disclosed compound of formula I, in which R1 represents a hydrophobic moiety adapted to occupy the C′ channel of human CDId, R2 represents a hydrophobic moiety adapted to occupy the A′ channel of human CDId, such that R1 fills at least at least 30% of the occupied volume of the C′ channel compared to the volume occupied by the terminal nC14H29 of the sphingosine chain of α-galactosylceramide when bound to human CDId and R2 fills at least 30% of the occupied volume of the A′ channel compared to the volume occupied by the terminal nC25H51 of the acyl chain of α-galactosylceramide when bound to human CDId R3 represents hydrogen or OH, Ra and Rb each represent hydrogen and in addition, when R3 represents hydrogen, Ra and Rb together may form a single bond, X represents or —CHA(CHOH)nY or —P(=0)(0−)0CH2(CH0H)mY, in which Y represents CHB1B2, n represents an integer from 1 to 4, m represents 0 or 1, A årepresents hydrogen, one of B1 and B2 represents H, OH or phenyl, and the other represents hydrogen or one of B1 and B2 represents hydroxyl and the other represents phenyl, in addition, when n represents 4, then A together with one of B1 and B2 together forms a single bond and th…