Ganglioside analogs

Details Ganglioside analogs Ganglioside analogs

C - Chemistry, Metallurgy

12

P

C12P 21/08 (2006.01) A61K 31/70 (2006.01) A61K 39/39 (2006.01) A61K 39/395 (2006.01) A61K 47/48 (2006.01) C07H 13/04 (2006.01) C07H 15/04 (2006.01) C07H 15/12 (2006.01) C07K 16/18 (2006.01) G01N 33/574 (2006.01)

Patent

CA 2123213

2123213 9310134 PCTABS00022 Ganglioside lactam analogue derivatives of general formula (I) in which A is a sialic acid residue of formula (II) which is bound via the dashed line in the 2-position; and in which Z1 is -OH or a group -NHX1, and Y30 is -CH3 or -CH2OH; X1 and Y1 together form a bond and Y2 is -OH or a group OR20, or X1 and Y2 together form a bond and Y1 is -OH or -NHAc; Y3 is -OH or a group -OR20; R1 is H or a sialic acid residue of formula (III) which is bound via the dashed line in the 2-position; and in which Z2 is -OH or a group -NHX2, and Y30 is as defined above; X2 and Y10 together form a bond and Y20 is -OH, or X2 and Y20 together form a bond and Y10 is -OH; with the provisos that when R1 is H, then Z1 is -NHX1, and that when R1 is a sialic acid residue of formula (III), then at least one of Z1 and Z2 is different from -OH; R10 is H, a carrier CA, or a group -(Sugar)n. The compounds are hydrolytically stable lactam analogs which spatially closely resemble the naturally occurring ganglioside lactones and are antigenic and able to induce the production of antibodies that cross-react with the corresponding ganglioside lactone.

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