Antibiotic oxazolidinone derivatives

A compound of the formula (I),

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• wherein:
• T is of the formula (IA), (IB) or (IC);
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• wherein the R6 group in (IC) may be in the 2- or 6-position relative to the ring nitrogen atom);
• R1 is chloro, fluoro, (1-4C)alkanesulfonyloxy, azido, (1-4C)alkoxy, (1-4C)alkylthio, (1-4C)alkylaminocarbonyloxy, or of the formula —NHC(═O)Rb wherein Rb is hydrogen, (1-4C)alkoxy, amino, chloromethyl, dichloromethyl, cyanomethyl, methoxymethyl, acetylmethyl, methylamino, dimethylamino or (1-4C)alkyl, or of the formula —NHS(O)n(1-4C)alkyl wherein n is 0, 1 or 2;
• R2 and R3 are independently hydrogen or fluoro;
• >A—B— is >C═CH—, >C(R4)—CH2—, >CH—CH2—, >C═C(R4a)—, >C(R4)—CH(R4a)— or >CH—CH(R4a)—(wherein, herein and hereinafter, > represents two single bonds), provided that >A—B— is not >C═CH—, >C═C(R4a)—, >C(R4)—CH(R4a)— or >CH—CH(R4a)— when T is of the formula (IA);
• wherein R4 is hydrogen, hydroxy, halo, (1-4C)alkyl or (1-4C)alkanoyloxy;
• R4a is (1-4C)alkyl;
• m is 0 or 1;
• wherein when T is of the formula (IA) or (IB);
• R6 is (1-4C)alkyl, (1-4C)alkanoylamino-(1-4C)alkyl, hydroxy-(1-4C)alkyl, carboxy, (1-4C)alkoxycarbonyl, AR-oxymethyl, AR-thiomethyl (wherein AR is as defined hereinbelow) or independently as defined for R5 hereinbelow (excluding R5 as hydrogen);
• R5 is hydrogen, cyano, 2-((1-4C)alkoxycarbonyl)ethenyl, 2-cyanoethenyl, 2-cyano-2-((1-4C)alkyl)ethenyl, 2-((1-4C)alkylaminocarbonyl)ethenyl, trityl or AR (as defined hereinbelow);
• or R5 is of the formula R10CO—, R10SO2— or R10CS—
• wherein R10 is AR (as defined hereinbelow), cyclopentyl or cyclohexyl (wherein the last two-mentioned cycloalkyl rings are optionally mono- or disubstituted by substituents independently selected from (1-4C)alkyl (including geminal disubstitution), hydroxy, (1-4C)alkoxy, (1-4C)alkylthio, acetamido, (1-4C)alkanoyl, cyano and trifluoromethyl), benzyloxy, (1-4C)alkoxycarbonyl, hydrogen, amino, trifluoromethyl, (1-4C)alkylamino, di((1-4C)alkyl)amino, 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 (1-4C)alkoxy, halo and cyano), benzopyranone or (1-10C)alkyl [wherein (1-10C)alkyl is optionally substituted by hydroxy, benzyloxy, cyano, halo, (1-10C)alkoxy, trifluoromethyl, (1-4C)alkoxy-(1-4C)alkoxy, (1-4C)alkoxy-(1-4C)alkoxy-(1-4C)alkoxy, (1-4C)alkanoyl, (1-4C)alkoxycarbonyl, amino, (1-4C)alkylamino, di((1-4C)alkyl)amino, (1-6C)alkanoylamino, (1-4C)alkoxycarbonylamino, N-(1-4C)alkyl-N-(2-6C)alkanoylamino, (1-4C)alkylS(O)pNH—, (1-4C)alkylS(O)p((1-4C)alkyl)N—, fluoro(1-4C)alkylS(O)pNH—, fluoro(1-4C)alkylS(O)p((1-4C)alkyl)N—, phosphono, (1-4C)alkoxy(hydroxy)phosphoryl, di-(1-4C)alkoxyphosphoryl, (1-4C)alkylS(O)q—, phenylS(O)q— (wherein the phenyl group is optionally substituted by up to three substituents independently selected from (1-4C)alkoxy, halo and cyano), or CY (as defined hereinbelow), wherein p is 1 or 2 and q is 0, 1 or 2];
• or R10 is of the formula R11C(O)O(1-6C)alkyl wherein R11 is an optionally substituted 5- or 6-membered heteroaryl, optionally substituted phenyl, (1-4C)alkylamino, benzyloxy-(1-4C)alkyl or optionally substituted (1-10C)alkyl;
• or R10 is of the formula R12O— wherein R12 is optionally substituted (1-6C)alkyl;
• or R5 is of the formula RdOC(Re)═CH(C═O)—, RfC(═O)C(═O)—, RgN═C(Rh)C(O)— or RiNHC(Rj)═CHC(═O)— wherein Rd is (1-6C)alkyl, Re is hydrogen or (1-6C)alkyl, or Rd and Re together form a (3-4C)alkylene chain, Rf is hydrogen, (1-6C)alkyl, hydroxy(1-6C)alkyl, (1-6C)alkoxy(1-6C)alkyl, amino, (1-4C)alkylamino, di-(1-4C)alkylamino, (1-6C)alkoxy, (1-6C)alkoxy(1-6C)alkoxy, hydroxy(2-6C)alkoxy, (1-4C)alkylamino(2-6C)alkoxy, di-(1-4C)alkylamino(2-6C)alkoxy, Rg is (1-6C)alkyl, hydroxy or (1-6C)alkoxy, Rh is hydrogen or (1-6C)alkyl, Ri is hydrogen, (1-6C)alkyl, optionally substituted phenyl or an optionally substituted 5- or 6-membered heteroaryl and Rj is hydrogen or (1-6C)alkyl;
• or R5 is of the formula R14CH(R13)(CH2)m— wherein m is 0 or 1, R13 is fluoro, cyano, (1-4C)alkoxy, (1-4C)alkylsulfonyl, (1-4C)alkoxycarbonyl or hydroxy, (provided that when m is 0, R13 is not fluoro or hydroxy) and R14 is hydrogen or (1-4C)alkyl;
• or when T is of the formula (IA), (IB) or (IC) R5 is ethenyl, 2-(AR)ethenyl, 2-(1-4C)alkylethenyl or of the formula (ID)
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• wherein X is —OR15, —SR15, —NHR15 and —N(R15)2 wherein R15 is hydrogen (when X is —NHR15 and —N(R15)2), (1-4C)alkyl or AR (as defined hereinbelow, when X is —OR15, —SR15 and —NHR15);
• and R16 is cyano, nitro, (1-4C)alkylsulfonyl, (4-10C)cycloalkylsulfonyl, phenylsulfonyl, (1-4C)alkanoyl and (1-4C)alkoxycarbonyl;
• or when T is of the formula (IA), (IB) or (IC);
• R5 and R6 are linked to give a group of the formula (IE) to (IT) [in which the N-atom shown is linked to R5 in (IA) to (IC), and the adjacent carbon atom shown in (IE) to (IT) is linked to R6 in (IA) to (IC)] so that a 5- or 6-membered ring is formed which is fused to the ring shown in (IA), (IB) or (IC) so as to give a bicyclic ring structure:
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• wherein
• D is independently selected from >C(R7)(R8) [or ═C(R8)— when D is connected to a carbon-carbon double bond, wherein═represents a carbon-carbon double bond], S(O)p [wherein p is 0, 1 or 2] and —O— [when D is not connected to a carbon-carbon double bond] and —NR9 [or N when D is connected to a carbon-carbon double bond];
• is E independently selected from >C(R7)(R8) [or ═C(R8)— when E is connected to a carbon-carbon double bond], S(O)p [wherein p is 0, 1 or 2] and >C═O [when E is not connected to a carbon-carbon double bond];
• wherein R7 and R8 are independently selected from hydrogen, (1-4C)alkyl, (optionally substituted by hydroxy, trifluoromethyl, (1-4C)alkyl S(O)q— (wherein q is 0, 1 or 2), (1-4C)alkoxy, carboxy, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl, di(N-(1-4C)alkyl)carbamoyl, cyano, nitro, amino, N-(1-4C)alkylamino, di(N-(1-4C)alkyl)amino or (1-4C)alkanoylamino), hydroxy [when D and E are not connected to a carbon-carbon double bond], (1-4C)alkoxy, halo, trifluoromethyl, thiol, (1-4C)alkyl S(O)q (wherein q is 0, 1 or 2), carboxy, (1-4C)alkoxycarbonyl, (1-4C)alkanoyl, carbamoyl, N-(1-4C)alkylcarbamoyl, di(N-(1-4C)alkyl)carbamoyl, (2-4C)alkenyl (optionally substituted by carboxy or (1-4C)alkoxycarbonyl), cyano, (1-4C)alkanoylamino, amino, N-(1-4C)alkylamino, di(N-(1-4C)alkyl)amino or nitro;
• wherein R9 is hydrogen, AR, trifluoromethyl, hydroxy, cyano, ethenyl, 2-(AR)ethenyl, 2-(1-4C)alkyl)ethenyl, 2-((1-4C)alkoxycarbonyl)ethenyl, 2-cyanoethenyl, 2-cyano-2-((1-4C)alkyl)ethenyl, 2-((1-4C)alkylaminocarbonyl)ethenyl, benzopyranone or (1-10C)alkyl [wherein (1-10C)alkyl is optionally substituted by hydroxy, halo (provided that (1-10C)alkyl is not methyl when substituted by hydroxy or halo), cyano, (1-10C)alkoxy, trifluoromethyl, (1-4C)alkoxy-(1-4C)alkoxy, (1-4C)alkoxy-(1-4C)alkoxy-(1-4C)alkoxy, (1-4C)alkanoyl, (1-4C)alkoxycarbonyl, amino, (1-4C)alkylamino, di((1-4C)alkyl)amino, (1-6C)alkanoylamino, (1-4C)alkoxycarbonylamino, N-(1-4C)alkyl-N-(2-6C)alkanoylamino, (1-4C)alkylS(O)pNH—, (1-4C)alkylS(O)p((1-4C)alkyl)N—, fluoro(1-4C)alkylS(O)pNH—, fluoro(1-4C)alkylS(O)p((1-4C)alkyl)N—, phosphono, (1-4C)alkoxy(hydroxy)phosphoryl, di-(1-4C)alkoxyphosphoryl, (1-4C)alkylS(O)q—, phenylS(O)q— (wherein the phenyl group is optionally substituted by up to three substituents independently selected from (1-4C)alkoxy, halo and cyano), AR or CY (as defined hereinbelow), wherein p is 1 or 2 and q is 0, 1 or 2];
• or R9 is of the formula R11C(O)O(1-6C)alkyl wherein R11 is an optionally substituted 5- or 6-membered heteroaryl, optionally substituted phenyl, (1-4C)alkylamino, benzyloxy-(1-4C)alkyl or optionally substituted (1-10C)alkyl;
• or R9 is of the formula R12O— wherein R12 is optionally substituted (1-6C)alkyl;
• wherein AR is optionally substituted phenyl, phenylcarbonyl (when in AR-oxymethyl), optionally substituted phenyl (1-4C)alkyl, 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;
• wherein CY is a 4-, 5- or 6-membered cycloalkyl ring, or a 5- or 6-membered cycloalkenyl ring;
• wherein any of the afore-mentioned ring systems in CY may be optionally substituted by up to three substituents independently selected from halo, (1-4C)alkyl (including geminal disubstitution when CY is a cycloalkyl or cycloalkenyl ring), acyl, oxo and nitro-(1-4C)alkyl;
• or a pharmaceutically-acceptable salt thereof.