Water-soluble prodrugs of chloramphenicol, thiamphenicol,...

C - Chemistry – Metallurgy – 07 – C

Patent

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Details

C07C 317/32 (2006.01) A61K 31/18 (2006.01) A61P 31/04 (2006.01) A61P 31/10 (2006.01) C07D 233/56 (2006.01)

Patent

CA 2672795

The present invention discloses prodrugs of chloramphenicol, thiamphenicol and their analogs, as well as pharmaceutically acceptable salts thereof, including nitrogen-containing esters of both alcohol groups. These prodrugs have the Formula (I), in which R, Aa, Ll, Mm, Xx, Y and R3 are as defined in the claims. In certain embodiments these prodrugs are sufficiently water-soluble to serve the functions needed of a prodrug of chloramphenicol, thiamphenicol and their analogs. In one embodiment, a certain subclass of the compounds also possess the hydrolytic stability needed to maintain the prodrug in solution in the subject's system until appropriate conditions exist when the prodrug can hydrolyze, releasing the active compound in question.

La présente invention concerne des promédicaments de chloramphénicol, de thiamphénicol et de leurs analogues, ainsi que des sels pharmaceutiquement acceptables de ceux-ci, y compris des esters contenant de l'azote des deux groupes alcool. Ces promédicaments sont représentés par la formule (I) dans laquelle R, Aa, Ll, Mm, Xx, Y and R3 sont tels que définis dans les revendications. Dans certains modes de réalisation, ces promédicaments sont suffisamment solubles dans l'eau pour garantir les fonctions nécessaires d'un promédicament de chloramphénicol, de thiamphénicol et de leurs analogues. Dans un mode de réalisation, une certaine sous-classe de composés présente également la stabilité hydrolytique nécessaire pour maintenir le promédicament en solution dans le système du sujet jusqu'à ce que se produisent les conditions adéquates pour que le promédicament puisse s'hydrolyser, libérant ainsi le composé actif en question.

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