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−).

##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−).

##STR00001##

The present invention relates to processes for preparing glucopyranosyl-substituted benzyl-benzene derivatives of general formula III,

##STR00001##

wherein R.sup.1, R.sup.2 and R′ are defined according to claim 1; and the use of such processes in the synthesis of SGLT2 inhibitors.

The present invention relates to processes for preparing glucopyranosyl-substituted benzyl-benzene derivatives of general formula III,

##STR00001##

wherein R.sup.1, R.sup.2 and R′ are defined according to claim 1; and the use of such processes in the synthesis of SGLT2 inhibitors.

It is provided i) an amorphous carbohydrate with improved chemical stability and/or physical features, ii) a method for producing an amorphous carbohydrate with improved chemical stability and/or physical features, and iii) a method for improving the chemical stability and/or the physical features of an amorphous carbohydrate.

It is provided i) an amorphous carbohydrate with improved chemical stability and/or physical features, ii) a method for producing an amorphous carbohydrate with improved chemical stability and/or physical features, and iii) a method for improving the chemical stability and/or the physical features of an amorphous carbohydrate.

The present invention provides an efficient process for preparing a nucleic acid oligomer, that is, a process for preparing a nucleic acid having a phosphate triester bond effectively by oxidizing a nucleic acid precursor having a phosphite triester bond. Specifically, the present invention provides a process for preparing a nucleic acid compound having at its 5′-terminus a nucleotide represented by formula (I) by a phosphoramidite method, which comprises a step of reacting a precursor having a phosphite triester bond represented by a formula (II) (the definitions of substituents of formulae (I) and (II) are described in the Description) with an oxidation solution subjected to a heat-treatment that contains iodine, pyridine and water.

##STR00001##

The present invention provides an efficient process for preparing a nucleic acid oligomer, that is, a process for preparing a nucleic acid having a phosphate triester bond effectively by oxidizing a nucleic acid precursor having a phosphite triester bond. Specifically, the present invention provides a process for preparing a nucleic acid compound having at its 5′-terminus a nucleotide represented by formula (I) by a phosphoramidite method, which comprises a step of reacting a precursor having a phosphite triester bond represented by a formula (II) (the definitions of substituents of formulae (I) and (II) are described in the Description) with an oxidation solution subjected to a heat-treatment that contains iodine, pyridine and water.

##STR00001##

An intermediate useful for the synthesis of an SGLT inhibitor and a method for preparing an SGLT inhibitor are provided. By employing an intermediate having Chemical Formula 5, the difficulty of purification with existing processes can be solved, the quality requirements for related substances can be achieved with only one purification step, and the quality control problem in each step can be solved by performing several steps in situ. A method for synthesizing a compound of Chemical Formula 1 by using a compound of Chemical Formula 5 enables purification in an earlier step, thereby solving the problems of existing synthesis processes, in which the quality requirements for related substances were difficult to control step-by-step due to a continuous process, thereby minimizing the amount of related substances in the final product. In addition, the yield of a diphenylmethane derivative according to Chemical Formula 1 is increased.

A method for producing a capped RNA which is an RNA having the 5′-end modified with a cap, the method including: reacting an activated capping compound represented by

##STR00001## with a monophosphate RNA having the 5′-end monophosphorylated, where, L represents a leaving group. The activated capping compound is preferably a compound represented by

##STR00002##