2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids

C - Chemistry – Metallurgy – 07 – D

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C07D 477/00 (2006.01) A61K 31/40 (2006.01) C07D 477/22 (2006.01) C07F 9/547 (2006.01) C07F 9/6561 (2006.01)

Patent

CA 1297110

TITLE OF THE INVENTION 2-AZA-SUBSTITUTED 1-CARBADETHIAPEN-2-EM-3- CARBOXYLIC ACIDS ABSTRACT OF THE INVENTION Disclosed are 2-aza-substituted 1-car- badethiapen-2-em-3-carboxylic acids I, where the generic 2-aza group includes azido, acylamino, amino, alkylamino, dialkylamino, triazolyl, triazolinyl, aziridinyl, and their pharmaceutically acceptable salt, ester, anhydride and amide derivatives which are useful as antibiotics. Also disclosed are processes for the preparation of I from the known, appropriately substituted bicyclic keto ester II via the 2-azido central intermediate III: Image 0725P/0905A 2802P/0747A 16349Y Image II Image III wherein R16 is H or CH3, preferably beta-methyl; R6, and R7 are independently hydrogen, linear, branched or cyclic C1-C5alkyl, which can be substituted with fluoro, hydroxy, protected hydroxy, sulfoxy, amino, protected amino, wherein R6 and R7 taken together can also be C2-C4 alkylidene, similarly substituted; with the proviso that both R6 and R7 are not unsubstituted alkyl, R1 and R2 are, inter alia, hydrogen, alkyl, acyl, and can be joined to form a ring comprising 3 to 7 atoms; Ra is hydrogen, a salt cation, a removable protecting group, or a pharmaceutically acceptable ester moiety. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

510827

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