Antibacterial compounds related to capuramycin

摘要

The compounds of formula (I), (XI), (XII), (XIII), (XIV), (XV) and (XVI) where in formula (I): R1 is a methyl group, R2 is a methyl group, R4 is a hydroxy group and X is a methylene group, R1 is a methyl group, R2 is a hydrogen group, R4 is a hydroxy group and X is a methylene group, R1 is a methyl group, R2 is a methyl group, R4 is a hydrogen group and X is a methylene group, R1 is a hydrogen group, R2 is a hydrogen group, R4 is a hydroxy group and X is a methylene group or R1 is a methyl group, R2 is a methyl group, R4 is a hydroxy group and X is a sulfur group. Pharmaceutical compositions can comprise the compounds of formula (Ia), (XI), (XII), (XIII), (XIV), (XV) and (XVI) where in formula (Ia): R1 is hydrogen or methyl R2a is hydrogen, methyl or a protecting group for a hydroxy group R3 and R5 are hydrogen or a protecting group for a hydroxy group R4a is a hydroxy group, hydroxy or a protected hydroxy group and X is a methylene group or a sulfur atom. Provided that when X is a sulfur atom, R1 is methyl, R2a is methyl and R4a is hydroxy group or a protected hydroxy group; X is a methylene group, R1 is methyl, R2a is hydrogen and R4a is hydroxy group or a protected hydroxy group Or when X is a methylene group, R1 is hydrogen, R2a is methyl and R4a is hydroxy group or a protected hydroxy group. And that when X is a methylene group, R1 is hydrogen, R2a is methyl, R3 is hydrogen or a phenoxythiocarbonyl group R4a may not be a hydroxy group when R5 is a hydrogen and R4a and R5 may not together represent an oxyalkylene group; And that the compound is excluded when X is a methylene group, R1 is hydrogen, R2a is methyl, R3 is a pivaloyl group o R4a is an acetoxy group and R5 is an acetyl group. The compositions are useful in treating bacterial infections. Also described is the process for preparing the compounds of formula (XI), (XII), (XIV) and (XV) comprising cultivating the microorganism strain Streptomyces griseus (SANK 60196; FERM BP-5420) and isolating the compound form the cultivation products.