The present invention is related to deuterated secnidazole, a prodrug thereof, a metabolite thereof, a hydrate thereof, a solvate thereof, a polymorph thereof, or a pharmaceutically acceptable salt thereof and its use for the treatment of bacterial vaginosis or trichomoniasis in a subject in need thereof. The present invention is also related to pharmaceutical compositions and methods and uses of treating bacterial vaginosis, trichomoniasis, amoebiasis, giardiasis, or a combination thereof. The present invention is also related to methods of screening deuterated forms of secnidazole to identify potent and high metabolic lifetime compounds for treating bacterial vaginosis or trichomoniasis.

The present invention is related to deuterated secnidazole, a prodrug thereof, a metabolite thereof, a hydrate thereof, a solvate thereof, a polymorph thereof, or a pharmaceutically acceptable salt thereof and its use for the treatment of bacterial vaginosis or trichomoniasis in a subject in need thereof. The present invention is also related to pharmaceutical compositions and methods and uses of treating bacterial vaginosis, trichomoniasis, amoebiasis, giardiasis, or a combination thereof. The present invention is also related to methods of screening deuterated forms of secnidazole to identify potent and high metabolic lifetime compounds for treating bacterial vaginosis or trichomoniasis.

Method of treating sexually transmitted infection in a subject in need thereof involving administering to the subject a therapeutically effective amount of secnidazole in a microgranule formulation, wherein the microgranule formulation comprises a plurality of microgranules having a volume-weighted particle size distribution within a microgranule population, wherein the volume-weighted particle size distribution as measured from a representative sample of the microgranule population comprises (a) 10% of the microgranule population having a volume-weighted particle size about no less than 470 micrometers; (b) 50% of the microgranule population having a volume-weighted particle size between about no less than 640 micrometers and about no more than 810 micrometers; (c) 90% of the microgranule population having a volume-weighted particle size about no more than 1170 micrometers; or (d) a combination thereof, which can include some or all of (a) through (c) above. Pharmaceutical compositions and uses thereof are included herein.

Method of treating sexually transmitted infection in a subject in need thereof involving administering to the subject a therapeutically effective amount of secnidazole in a microgranule formulation, wherein the microgranule formulation comprises a plurality of microgranules having a volume-weighted particle size distribution within a microgranule population, wherein the volume-weighted particle size distribution as measured from a representative sample of the microgranule population comprises (a) 10% of the microgranule population having a volume-weighted particle size about no less than 470 micrometers; (b) 50% of the microgranule population having a volume-weighted particle size between about no less than 640 micrometers and about no more than 810 micrometers; (c) 90% of the microgranule population having a volume-weighted particle size about no more than 1170 micrometers; or (d) a combination thereof, which can include some or all of (a) through (c) above. Pharmaceutical compositions and uses thereof are included herein.

Embodiments are directed to a secnidazole formulations and the use of a secnidazole formulation for the treatment of bacterial vaginosis (BV).

Embodiments are directed to a secnidazole formulations and the use of a secnidazole formulation for the treatment of bacterial vaginosis (BV).

This invention relates to the medical use of an antimicrobial agent, racemic Ornidazole, its (R) and (S) enantiomers, or pharmaceutically acceptable salts or esters thereof, and to methods of treatment which involve treating a subject with Ornidazole. The racemic (rac)-ornidazole, its enantiomers, or pharmaceutically acceptable salts or esters thereof, may be used in combination with other actives. The invention also relates to pharmaceutical formulations and compositions comprising (rac)-ornidazole, (R)-ornidazole, (S)-ornidazole, or pharmaceutically acceptable salts or esters thereof, and/or other actives as well as methods to stereoselectively manufacture the enantiomers.

This invention relates to the medical use of an antimicrobial agent, racemic Ornidazole, its (R) and (S) enantiomers, or pharmaceutically acceptable salts or esters thereof, and to methods of treatment which involve treating a subject with Ornidazole. The racemic (rac)-ornidazole, its enantiomers, or pharmaceutically acceptable salts or esters thereof, may be used in combination with other actives. The invention also relates to pharmaceutical formulations and compositions comprising (rac)-ornidazole, (R)-ornidazole, (S)-ornidazole, or pharmaceutically acceptable salts or esters thereof, and/or other actives as well as methods to stereoselectively manufacture the enantiomers.

Fexinidazole is prepared according to a method which comprises the following steps: a) reacting 1-methyl-2-hydroxymethyl-5-nitro-imidazole with methanesulfonyl chloride in the presence of a suspension of powdered alkaline carbonate in an anhydrous organic solvent suitable for performing nucleophile substitution reactions; b) adding to the resulting reaction medium a solution of 4-methyl-mercapto-phenol in the same organic solvent as referred to in step a); c) separating fexinidazole from the reaction mixture as its hydrochloride salt and d) converting said hydrochloride salt into fexinidazole and optionally, purifying the latter.

Fexinidazole is prepared according to a method which comprises the following steps: a) reacting 1-methyl-2-hydroxymethyl-5-nitro-imidazole with methanesulfonyl chloride in the presence of a suspension of powdered alkaline carbonate in an anhydrous organic solvent suitable for performing nucleophile substitution reactions; b) adding to the resulting reaction medium a solution of 4-methyl-mercapto-phenol in the same organic solvent as referred to in step a); c) separating fexinidazole from the reaction mixture as its hydrochloride salt and d) converting said hydrochloride salt into fexinidazole and optionally, purifying the latter.