Lipid a analogs having immunoactivating and anti-tumor activity

C - Chemistry – Metallurgy – 07 – H

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C07H 13/04 (2006.01) A61K 31/70 (2006.01) C07H 13/06 (2006.01) C07H 13/12 (2006.01) C07H 15/10 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2019972

Compounds of formula (I): (see formula I) [in which: R1 is hydroxy, protected hydroxy, fluorine, or -OP(O)(OH)2; R2 and R3 are independently optionally substituted C6 - C20 aliphatic acyl; R4 is hydroxy, protected hydroxy, or -OP(O)(OH)2, where at leant one of R1 and R4 is -OP(O)(OH)2; and R5 is hydroxy, protected hydroxy, or fluorine; provided that, except where at least one of R1 and R5 is fluorine, then at least one of R2 and R3 is a substituted C6 - C20 aliphatic acyl having (i) at least one halogen substituent and (ii) at least one substituent selected from the group consisting of halogen, hydroxy and C6 - C20 aliphatic acyloxy or at least one of R and R is a substituted C6 - C20 aliphatic aryl which is substituted by at least one halogen-substituted C6 - C20 aliphatic carboxylic acyloxy]; have Lipid A-like activity and may be used for the treatment, prophylaxis, diagnosis and support of an animal suffering a disease or disorder arising from a deficiency in the immune system or from a tumor. They may be prepared by phosphorylation of corresponding compounds lacking a phosphoryl group.

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