Analogs of alpha galactosyceramide and uses thereof

Details Analogs of alpha galactosyceramide and uses thereof Analogs of alpha galactosyceramide and uses thereof

2006-10-25

2011-10-18

Davis, Brian J (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S208000, C558S030000, C558S170000, C514S076000, C514S114000, C514S517000, C514S625000, C514S627000

Reexamination Certificate

active

08039670

ABSTRACT:
There are disclosed compound of formula I, in which R1represents a hydrophobic moiety adapted to occupy the C′ channel of human CDId, R2represents a hydrophobic moiety adapted to occupy the A′ channel of human CDId, such that R1fills at least at least 30% of the occupied volume of the C′ channel compared to the volume occupied by the terminal nC14H29of the sphingosine chain of α-galactosylceramide when bound to human CDId and R2fills at least 30% of the occupied volume of the A′ channel compared to the volume occupied by the terminal nC25H51of the acyl chain of α-galactosylceramide when bound to human CDId R3represents hydrogen or OH, Raand Rbeach represent hydrogen and in addition, when R3represents hydrogen, Raand Rbtogether 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 B1and B2represents H, OH or phenyl, and the other represents hydrogen or one of B1and B2represents hydroxyl and the other represents phenyl, in addition, when n represents 4, then A together with one of B1and B2together forms a single bond and the other of B1and B2represents H, OH or OSO3H 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.

REFERENCES:
Tsunoda H. et al., “Synthesis of 5A-Carba-Beta-D-Glycosylceramide Analogs Linked by Imino, Ether and Sulfide Bridges,” Liebigs Annalen: Organic and Bioorganic Chemistry, VCH Publishers, US, pp. 267-277 (1995).
Bushnev, A. S., et al., “Synthesis of rac-ceramide-1-phosphoglycerol via rac-3-benzoylceramide phosphate,” Bioorganicheskaya Khimiya, 5:2:234-237 (1979).
Bushnev, A. S., et al., “Synthesis of rac-ceramide-1-phosphoglycerol via rac-3-benzoylceramide phosphate,” Chemical Abstracts Service, 90:167983 (1979).

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