Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods

A compound of Formula I

• wherein:
• R is selected from the group consisting of OH, O-Aryl, O-Heteroaryl, N3, OR′, OSO2R″, —NR′″R″″, or
• wherein:
• (i) R′ is straight-chain or branched acyl having up to 6 carbon atoms or benzyl;
• (ii) R″ is straight-chain or branched alkyl, having up to 5 carbon atoms, phenyl or tolyl;
• and
• (iii) R′″ and R″″ are independently selected from the group consisting of H, cycloalkyl having 3 to 6 carbon atoms, phenyl or tert-butoxycarbonyl, fluorenyloxycarbonyl, benzyloxycarbonyl, straight-chain or branched alkyl having up to 6 carbon atoms which is optionally substituted by cyano or alkoxycarbonyl having up to 4 carbon atoms, —CO2—R1, —CO—R1, —CS—R1, and —SO2—R4, in which
• R1 is selected from the group consisting of H, cycloalkyl having 3 to 6 carbon atoms, trifluoromethyl or phenyl, benzyl or acyl having up to 5 carbon atoms, straight-chain or branched alkyl having up to 6 carbon atoms, said alkyl optionally substituted by straight-chain or branched alkoxycarbonyl having up to 5 carbon atoms, OH, cyano, up to 3 halogen atoms, and —NR5 R6 in which R5 and R6 are identical or different and are selected from H, phenyl or straight-chain or branched alkyl having up to 4 carbon atoms;
• R4 is selected from straight-chain or branched alkyl having up to 4 carbon atoms or phenyl and;
• R4a is CN, COR4c, COOR4c, CONHR4c, CO—NR4c R4d, SO2R4c, or NO2;
• R4b is H, alkyl, OR4c, SR4c, amino, NHR4c, NR4c, R4d;
• R4c and R4d are independently selected from H, alkyl, aryl, or in the case of any NR4cR4d group R4c and R4d taken together with the nitrogen atom to which they are attached form a unsubstituted or substituted pyrrolidinyl, piperidinyl or morpholinyl group;
• X is 0 to 4 members independently selected from the group consisting of halogen, OH, nitro, C1-8 alkoxy, C1-8 alkyl-amino, di(C1-8-alkyl-)amino, carboxy, alkoxycarbonyl, C1-8 alkyl-CO—O—, C1-8 alkyl-CO—NH—, carboxamide, CN, amine, C3-6 cycloalkyl, C1-8 alkyl optionally substituted with one or more members selected from the group consisting of F, Cl, OH;
• and
• Y is a radical of Formulae II or III:
• wherein
• R5, R6, R7, and R8 are each independently H, alkyl, CN, nitro, C1-8 alkyl, halo-C1-8-alkyl, formyl, carboxy, alkoxycarbonyl, carboxamide, or R5 and R6 and/or R7 and R8 together form an oxo group;
• R9, and R10 are each independently H, halogen, alkyl, OH, CN, nitro, C1-8 alkyl, halo-C1-8-alkyl, C1-8 alkoxyl, amino, C1-8-alkyl-amino, di(C1-8-alkyl)-amino, formyl, carboxy, alkoxycarbonyl, C1-8-alkyl-CO—O—, C1-8-alkyl-CO—NH—, carboxamide, or amine;
• is a fused phenyl ring or a five- or six-membered heteroaromatic ring having one to four members selected from the group consisting of S, O, and N;
• Z is halogen, alkyl, substituted-alkyl, aryl, substituted-aryl, heteroaryl, substituted-heteroaryl, CN, CHO, COalkyl, amino, alkoxy, HNCO—(C1-C8alkyl), allyl, propargyl, allenyl, or N-alkylthiocarbamoyl;
• and
• m is 0 or 1,
• and the pharmaceutically acceptable salts and esters thereof.