Antibiotic oxazolidinone derivatives

A compound of formula (I):

• wherein
• R1 is OH;
• R2 and R3 are each independently hydrogen or fluoro;
• R4 and R5 are each independently hydrogen, C1-4alkyl, carboxy, C1-4alkoxycarbonyl or independently R7;
• R6 is hydrogen, C1-4alkyl, hydroxy, C1-4alkoxy, or C2-4alkanoylalkoxy;
• D is a protected amine;
• R7 is hydrogen, cyano, 2-(C1-4alkoxycarbonyl)ethenyl, 2-cyanoethenyl, 2-cyano-2-(C1-4alkyl)ethenyl, 2-(C1-4alkylaminocarbonyl)ethenyl, AR or a tretrazole ring system, optionally mono-substituted in the 1- or 2-position of the tetrazole ring, wherein the tetrazole ring system is joined to the nitrogen in NR7 by a ring carbon atom;
• or
• R7 is of the formula R10C(═O)—, R10SO2— or R10C(═S)—;
• or
• R7 is of the formula RdOC(Re)═CHC(═O)—, RfC(═O)C(═O)—, RgN═C(Rh)C(═O)— or RiNHC(Rj)═CHC(═O)—;
• or
• R7 is of the formula R14CH(R13)(CH2)m—;
• R10 is AR, cyclopentyl or cyclohexyl, wherein the last two mentioned cycloalkyl rings are optionally mono- or di-substituted by substituents selected from C1-4alkyl, hydroxy, C1-4alkoxy, C1-4alkylthio, acetamido, C1-4alkanoyl, cyano and trifluoromethyl;
• or
• R10 is C1-4alkoxycarbonyl, hydrogen, amino, C1-4alkylamino, diC1-4alkalkylamino, 2,3-dihydro-5-oxothiazolo-[3,2-A]pyrimidin-6-yl, 2-(2-furyl)ethenyl, 2-(2-thienyl)ethenyl, 2-phenylethenyl, wherein the phenyl substituent is optionally substituted by up to three substituents independently selected from C1-4alkoxy, halo and cyano;
• or
• R10 is 3,4-dihydropyran-2-yl, coumal-5-yl, 5-methoxy-4-oxopyran-2-yl, N-acetylpyrrolidin-2-yl, 5-oxotetrahydrofuran-2-yl, benzopyranone or C1-10alkyl, wherein C1-10alkyl is optionally substituted by hydroxy, cyano, halo, C1-10alkoxy, trifluoromethyl, C1-4alkoxy-C1-4alkoxy, C1-4alkoxy-C1-4alkoxy-C1-4alkoxy, C1-4alkanoyl, C1-4alkoxycarbonyl, amino, C1-4alkylamino, diC1-4alkylamino, C1-6alkanoylamino, C1-4alkoxycarbonylamino, N—C1-4alkoyl-N—C2-6alkanoylamino, C1-4alkylS(═O)pNH—, C1-4alkS(═O)p(C1-4alkyl)N—, fluoroC1-4alkylS(═O)pNH—, fluoroC1-4alkS(═O)p(C1-4alkyl)N—, phosphono, C1-4alkoxy(hydroxy)phosphoryl, diC1-4alkoxyphosphoryl, C1-4alkylS(═O)q—, CY or phenylS(═O)q—, wherein the phenyl group is optionally substituted by up to three substituents independently selected from C1-4alkoxy, halo and cyano;
• or
• R10 is R11C(═O)OC1-6alkyl or R12O—;
• R11 is an optionally substituted 5- or 6-membered heteroaryl, optionally substituted phenyl, C1-4alkylamino, benyloxyC1-4alkalkyl, or optionally substituted C1-10alkyl;
• R12 is optionally substituted C1-6alkyl;
• R13 is fluoro, cyano, C1-4alkoxy, C1-4alkylsulfonyl, C1-4alkoxycarbonyl or hydroxy, provided that when m is 0, R13 is not fluoro or hydroxy;
• R14 is hydrogen or C1-4alkyl;
• >A—B is of the formula >C═C(Ra)—, >CHCHRa— or >C(OH)CHRa;
• > represents two single bonds
• Ra is hydrogen or C1-4alkyl;
• Rd is C1-6alkyl;
• Re is hydrogen or C1-6alkyl;
• or Rd and Re together form a C3-4alkylene chain;
• Rf is hydrogen, C1-6alkyl, hydroxylC1-6alkyl, C1-6alkoxyC1-6alkyl, amino, C1-4alkylamino, diC1-4alkylamino, C1-6alkoxy, C1-6alkoxyC1-6alkoxy, hydroxyC2-6alkoxy, C1-4alkylaminoC2-6alkoxy or diC1-4alkylaminoC2-6alkoxy;
• Rg is C1-6alkyl, hydroxy, or C1-6alkoxy;
• Rh is hydrogen or C1-6alkyl;
• Ri is hydrogen, C1-6alkyl, optionally substituted phenyl or an optionally substituted 5- or 6-membered heteroaryl;
• Rj is hydrogen or C1-6alkyl;
• AR is optionally substituted phenyl, optionally substituted phenylC1-4alkyl, optionally substituted 5- or 6-membered heteroaryl, optionally substituted naphthyl or an optionally substituted 5/6 or 6/6 bicyclic heteroaryl ring system, in which the bicyclic heteroaryl ring systems may be linked via an atom in either of the rings comprising the bicyclic system, and wherein the mono- and bicyclic heteroaryl ring systems are linked via a ring carbon atom;
• CY is 4-, 5- or 6-membered cycloalkyl ring, a 5- or 6-membered cycloalkenyl ring, naphthoxy, thiophen-2-yl, indol-1-yl, indol-3-yl, pyrimidin-2-ylthio, 1,4-benxoioxan-6-yl, sulfolan-3-yl or pyridin-2-yl, wherein any of the aforementioned ring systems in CY may be optionally substituted by up to three substituents independently selected from halo, C1-4alkyl, acyl, oxo and nitroC1-4alkyl,
• m is 0 or 1;
• p is 1 or 2;
• and
• q is 0, 1, or 2;
• or
• a pharmaceutically acceptable salt thereof.