Lipid A analogs having immunoactivating and anti-tumor activity

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 184, 536117, 536119, 536122, C07H 502, C07H 1104, C07H 1302, C07H 1306

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active

057928401

ABSTRACT:
Compounds of formula (I): ##STR1## in which: R.sup.1 is hydroxy, protected hydroxy, fluorine, or --OP(O)(OH).sub.2 ; R.sup.2 and R.sup.3 are independently optionally substituted C.sub.6 -C.sub.20 aliphatic acyl; R.sup.4 is hydroxy, protected hydroxy, or --OP(O)(OH).sub.2, where at least one of R.sup.1 and R.sup.4 is --OP(O)(OH).sub.2 ; and R.sup.5 is hydroxy, protected hydroxy, or fluorine; provided that, except where at least one of R.sup.1 and R.sup.5 is fluorine, then at least one of R.sup.2 and R.sup.3 is a substituted C.sub.6 -C.sub.20 aliphatic acyl having (i) at least one halogen substituent and (ii) at least one substituent selected from the group consisting of halogen, hydroxy and C.sub.6 -C.sub.20 aliphatic acyloxy or at least one of R.sup.2 and R.sup.3 is a substituted C.sub.6 -C.sub.20 aliphatic acyl which is substituted by at least one halogen-substituted C.sub.6 -C.sub.20 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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Chemical Abstracts, vol. 103, No. 3, 22 Jul. 1985, (Columbus, Ohio, US) Kasai et al.: "In Vitro Antigenic Reactivity of Synthetic Lipid A Analogs as determined by Monoclonal and Conventional Antibodies", p. 436, abstract 20888u, Biochem. Biophys. Res. Comman.
Chemical Abstracts, vol. 97, No. 23, 6 Dec. 1982, (Columbus, Ohio, U.S.), Verret et al.: "Fatty Acyl Amidases from Dictyostelium Discoideum that Act on Lipopolysaccharide and Derivatives. II. Aspects of Substrate Specificity." p. 271, abstract 195017u, J. Biol. Chem. 1982, 157 (17), 10228-34.
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