1-methylcarbapenem derivatives

C - Chemistry – Metallurgy – 07 – D

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C07D 477/20 (2006.01) A61K 31/407 (2006.01) A61P 31/04 (2006.01)

Patent

CA 2429346

1-Methylcarbapenem compounds having excellent antimicrobial activity, or pharmacologically acceptable ester derivatives or salts thereof; pharmaceutical compositions (particularly antimicrobials) containing the same as the active ingredient; use of the compounds, the ester derivatives, or the salts in preparing the pharmaceutical compositions; and methods for prevention or treatment of diseases (particularly microbism) by administering the compounds, the ester derivatives, or the salts in pharmacologically effective doses to warm-blooded animals (particularly human beings). The compounds are represented by the general formula (|): (|) wherein R1 is COOR3 (wherein R3 is hydrogen, C1-6 alkyl, or the like), CONR4R5 (wherein R4 and R5 are each hydrogen, optionally substituted C1-6 alkyl, or the like), cyano, CH2OR6 (wherein R6 is hydrogen, C1-6 alkyl, or the like), or CH2NR7R8 (wherein R7 is hydrogen, C1-6 alkyl, or the like, and R8 is hydrogen, C1-6 alkyl, C1-6 alkanoyl, C1-6 alkoxycarbonyl, or the like); R2 is hydrogen or C1-6 alkyl; n is 1, 2, or 3; and X is sulfur or oxygen.

La présente invention concerne des composés à base de 1-méthylcarbapenem présentant une bonne activité antimicrobienne, ou certains de leurs dérivés ou sels d'esters pharmacologiquement admis. L'invention concerne également des compositions pharmaceutiques, en particulier des antimicrobiens, dont ces composés sont les principes activs. L'invention concerne aussi l'utilisation de ces composés, de leurs dérivés esters ou de leurs sels pour la préparation de compositions pharmaceutiques. L'invention concerne enfin des traitements prophylactiques et thérapeutiques d'affections, en particuliers microbiennes, par administration de doses pharmacologiquement efficaces de ces composés, dérivés esters ou sels, à des animaux à sang chaud, en particulier les humains. Ces composés sont représentés par la formule générale (I). Dans cette formule, R?1¿ est COOR?3¿ (auquel cas R?3¿ est hydrogène, C¿1-6? alkyle, ou analogue), CONR?4¿R?5¿ (auquel cas R?4¿ et R?5¿ sont chacun hydrogène, C¿1-6? alkyle éventuellement substitué, ou analogue), cyano, CH¿2?OR?6¿ (auquel cas R?6¿ est hydrogène, C¿1-6? alkyle, ou analogue), ou CH¿2?NR?7¿R?8¿ (auquel cas R?7¿ est hydrogène, C¿1-6? alkyle, ou analogue, et R?8¿ est hydrogène, C¿1-6? alkyle, C¿1-6? alcanoyle, C¿1-6? alcoxycarbonyle, ou analogue); R?2¿ est hydrogène ou C¿1-6? alkyle; n vaut 1, 2 ou 3; et X est soufre ou oxygène.

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