Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1.fwdarw.6)-glucosamine groups.

The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof. ##STR00001##

The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof. ##STR00001##

The present invention relates to new synthetic molecules with agonist activity of human Toll-like Receptor 4 (TLR4), compositions comprising them and uses thereof for the treatment of diseases in which it is useful to induce or increase an immune response. The compounds have general formula (1), wherein R.sub.1 is a saturated C.sub.8-C.sub.16 aliphatic chain having a =0 on C.sub.1, said chain being free from OH substituents on C.sub.3, wherein R.sub.2 is a saturated C.sub.8-C.sub.16 aliphatic chain having a O on C.sub.1, said chain being free from OH substituents on C.sub.3, wherein R.sub.3 is a saturated C.sub.8-C.sub.16 aliphatic chain having a O on C.sub.1, said chain being free from OH substituents on C.sub.3; wherein R.sub.4 is a hydrogen atom (H) or a phosphate group (PO.sub.4.sup.2).

The present invention relates to new synthetic molecules with agonist activity of human Toll-like Receptor 4 (TLR4), compositions comprising them and uses thereof for the treatment of diseases in which it is useful to induce or increase an immune response. The compounds have general formula (1), wherein R.sub.1 is a saturated C.sub.8-C.sub.16 aliphatic chain having a =0 on C.sub.1, said chain being free from OH substituents on C.sub.3, wherein R.sub.2 is a saturated C.sub.8-C.sub.16 aliphatic chain having a O on C.sub.1, said chain being free from OH substituents on C.sub.3, wherein R.sub.3 is a saturated C.sub.8-C.sub.16 aliphatic chain having a O on C.sub.1, said chain being free from OH substituents on C.sub.3; wherein R.sub.4 is a hydrogen atom (H) or a phosphate group (PO.sub.4.sup.2).

An object of the invention is to provide a method of uniformly and efficiently producing a saccharide having a sulfate group and/or a phosphate group in the molecule, or a compound containing the saccharide. [Solution] The present invention provides a method of producing a saccharide having a sulfate group and/or a phosphate group. The method comprises (a) a step of preparing a first saccharide having a non-protected sulfate group and/or a non-protected phosphate group and a second saccharide having a non-protected sulfate group and/or a non-protected phosphate group and (b) a step of condensing the first saccharide and the second saccharide prepared in the step (a) with each other.

An object of the invention is to provide a method of uniformly and efficiently producing a saccharide having a sulfate group and/or a phosphate group in the molecule, or a compound containing the saccharide. [Solution] The present invention provides a method of producing a saccharide having a sulfate group and/or a phosphate group. The method comprises (a) a step of preparing a first saccharide having a non-protected sulfate group and/or a non-protected phosphate group and a second saccharide having a non-protected sulfate group and/or a non-protected phosphate group and (b) a step of condensing the first saccharide and the second saccharide prepared in the step (a) with each other.

There are provided compounds of Formula (A) and pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions thereof, used for the prevention or treatment in a mammal of joint and bone disorders such as arthritis and osteoporosis.

##STR00001##

There are provided compounds of Formula (A) and pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions thereof, used for the prevention or treatment in a mammal of joint and bone disorders such as arthritis and osteoporosis.

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Toll-like receptor (TLR) ligands having an allose-based core are stable in aqueous formulation and are useful in treating, preventing, or reducing susceptibility to diseases or conditions mediated by TLRs, such as cancer, infectious disease, allergy, autoimmune disease, sepsis, and ischemia reperfusion.