The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: ##STR00001## The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

A method of preparing an intermediate useful for the synthesis of a diphenylmethane derivative that can be used as an SGLT inhibitor is described. A method of synthesizing a compound of Formula 7 can address problems of existing synthesis processes requiring the synthesis of the Grignard reagent and management of related substances. In addition, the method can minimize the generation of related substances, and thus does not require reprocessing of reaction products, thereby simplifying the process. Accordingly, the production yield of a diphenylmethane derivative can be maximized.

Compounds and methods of using said compounds, singly or in combination with additional agents, and salts, crystalline forms, pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.

Compounds and methods of using said compounds, singly or in combination with additional agents, and salts, crystalline forms, pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.

Described herein are trehalose analogues. Also described herein are methods of making the trehalose analogues and uses of the analogues. For example, the disclosed trehalose analogues may be useful in the detection of bacteria.

Described herein are trehalose analogues. Also described herein are methods of making the trehalose analogues and uses of the analogues. For example, the disclosed trehalose analogues may be useful in the detection of bacteria.

The invention relates to a process to prepare a compound of the following formula (I):

##STR00001## in which P represents a protective group of a hydroxyl function which is a —COR.sup.1 group with R.sup.1 representing an aryl or a (C.sub.1-C.sub.6)alkyl, R represents a hydrogen atom or a protective group of a terminal alkyne, from mannose, comprising the following steps: (a) protecting the 5 hydroxyl groups of the mannose by a protective group P; (b) coupling the protected mannose obtained at step (a) with a compound of the following formula (II)

##STR00002##

The present invention also relates to a compound of formula (IIIa):

##STR00003## wherein R.sup.10 represents a hydrogen, a (C.sub.1-C.sub.6)alkyl, —SO.sub.2R.sup.6, —C(O)R.sup.6 or —C(O)OR.sup.6, with R.sup.6 being a hydrogen or a radical selected from a (C.sub.1-C.sub.6)alkyl, an aryl, a heteroaryl, a 3-8 membered ring cycloalkyl and a 3-8 membered ring heterocycloalkyl, said radical being optionally substituted by a (C.sub.1-C.sub.6) alkyl, an aryl, a heteroaryl, a 3-8 membered ring cycloalkyl or a 3-8 membered ring heterocycloalkyl, a halogen, —NR.sup.8R.sup.9, —CN, —C(O)OR.sup.8, —C(O)NR.sup.8R.sup.9 or —OR.sup.8, with R.sup.8 and R.sup.9 being independently a hydrogen atom or a (C.sub.1-C.sub.6) alkyl, or R.sup.8 and R.sup.9 form together with the nitrogen to which they are bound a 3-8 membered ring heterocycloalkyl, and R″ represents —COR.sup.1 group with R.sup.1 being an aryl or a (C.sub.1-C.sub.6)alkyl.

The invention relates to a process to prepare a compound of the following formula (I):

##STR00001## in which P represents a protective group of a hydroxyl function which is a —COR.sup.1 group with R.sup.1 representing an aryl or a (C.sub.1-C.sub.6)alkyl, R represents a hydrogen atom or a protective group of a terminal alkyne, from mannose, comprising the following steps: (a) protecting the 5 hydroxyl groups of the mannose by a protective group P; (b) coupling the protected mannose obtained at step (a) with a compound of the following formula (II)

##STR00002##

The present invention also relates to a compound of formula (IIIa):

##STR00003## wherein R.sup.10 represents a hydrogen, a (C.sub.1-C.sub.6)alkyl, —SO.sub.2R.sup.6, —C(O)R.sup.6 or —C(O)OR.sup.6, with R.sup.6 being a hydrogen or a radical selected from a (C.sub.1-C.sub.6)alkyl, an aryl, a heteroaryl, a 3-8 membered ring cycloalkyl and a 3-8 membered ring heterocycloalkyl, said radical being optionally substituted by a (C.sub.1-C.sub.6) alkyl, an aryl, a heteroaryl, a 3-8 membered ring cycloalkyl or a 3-8 membered ring heterocycloalkyl, a halogen, —NR.sup.8R.sup.9, —CN, —C(O)OR.sup.8, —C(O)NR.sup.8R.sup.9 or —OR.sup.8, with R.sup.8 and R.sup.9 being independently a hydrogen atom or a (C.sub.1-C.sub.6) alkyl, or R.sup.8 and R.sup.9 form together with the nitrogen to which they are bound a 3-8 membered ring heterocycloalkyl, and R″ represents —COR.sup.1 group with R.sup.1 being an aryl or a (C.sub.1-C.sub.6)alkyl.

The present invention relates to methods, compounds, and compositions for treating viral infections, including COVID-19 viral infections. In certain embodiments, the compositions comprise: i) a remdesivir analog, ii) remdesivir or a remdesivir analog, and a surfactant, a cyclodextrin, or a combination thereof, iii) nanoparticles comprising albumin and remdesivir or remdesivir analog, iv) liposomes comprising lipids and remdesivir or remdesivir analog; and/or v) microparticles comprising PLA and/or PLGA, and remdesivir or remdesivir analog. In certain embodiments, the compositions are aqueous (e.g., for intravenous administration). In other embodiments, the compositions are nebulized or in the form of a dry powder (e.g., for inhalation by an infected subject).

The present invention relates to methods, compounds, and compositions for treating viral infections, including COVID-19 viral infections. In certain embodiments, the compositions comprise: i) a remdesivir analog, ii) remdesivir or a remdesivir analog, and a surfactant, a cyclodextrin, or a combination thereof, iii) nanoparticles comprising albumin and remdesivir or remdesivir analog, iv) liposomes comprising lipids and remdesivir or remdesivir analog; and/or v) microparticles comprising PLA and/or PLGA, and remdesivir or remdesivir analog. In certain embodiments, the compositions are aqueous (e.g., for intravenous administration). In other embodiments, the compositions are nebulized or in the form of a dry powder (e.g., for inhalation by an infected subject).