Antibiotic oxazolidinone derivatives

A compound of formula (I):

• ##STR23## wherein:
• R.sup.1 is hydroxy, chloro, fluoro, (1-4C) alkanesulfonyloxy, amino, azido, (1-4C)alkoxy, (1-4C)alkylthio, (1-4C)alkylaminocarbonyloxy;
• or of the formula --NHC(.dbd.O)R.sup.b wherein R.sup.b is hydrogen, (1-4C)alkoxy, amino, chloromethyl, dichioromethyl, cyanomethyl, methoxyrnethyl, acetylmethyl, methylamino, dimethylamino or (1-4C)alkyl;
• or R.sup.1 is of the formula --NHS(O).sub.n (1-4C)alkyl wherein n is 0, 1 or 2;
• R.sup.2 and R.sup.3 are independently hydrogen or fluoro;
• D is NR.sup.7 ;
• R.sup.4 and R.sup.5 are independently, (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 R.sup.7 hereinbelow;
• R.sup.6 is hydrogen, (1-4C)alkyl, hydroxy, (1-4C)alkoxy or (2-4C)alkanoyloxy;
• >A--B-- is of the formula >C.dbd.C(R.sup.a)--, >CHCHR.sup.a -- or >C(OH)CHR.sup.a -- (>represents two single bonds) wherein R.sub.a is hydrogen or (1-4C)alkyl;
• and
• R.sup.7 is hydrogen, cyano, 2-((1-4C)alkoxycarbonyl)ethenyl, 2-cyanoethenyl, 2-cyano-2-(1-4C)alkyl)ethenyl, 2-((1-4C)alkylaminocarbonyl)ethenyl, AR (as defined hereinbelow) or a tetrazole 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 NR.sup.7 by a ring carbon atom;
• or R.sup.7 is of the formula R.sup.10 CO--, R.sup.10 SO.sub.2 -- or R.sup.10 CS-- wherein R.sup.10 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), (1-4C)alkoxycarbonyl, hydrogen, amino, trifluoromethyl, (1-4C)alkylamino, di((1-4C)alkyl)amino, 2,3-dihydro-5-oxothiazolo-[3,2-A]pyrimaidin-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 (1-4C)alkoxy, halo and cyano), 3,4-dihydropyran-2-yl, coumal-5-yl, 5-methoxy-4-oxopyran-2-yl, N-acetylpyrrolidin-2-yl, 5-oxo-tetrahydrofuran-2-yl, benzopyranone or (1-10C)alkyl;
• or R.sup.10 is of the formula R.sup.11 C(O)O(1-6C)alkyl wherein R.sup.11 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 R.sup.10 is of the formula R.sup.12 O-- wherein R.sup.12 is optionally substituted (1-6C)alkyl;
• or R.sup.7 is of the formula R.sup.d OC(R.sup.e).dbd.CH(C.dbd.O)--, R.sup.f C(.dbd.O)C(.dbd.O)--, R.sup.g N.dbd.C(R.sup.h)C(.dbd.O)-- or R.sup.i NHC(R.sup.j).dbd.CHC(.dbd.O)-- wherein R.sup.d is (1-6C)alkyl, R.sup.e is hydrogen or (1-6C)alkyl, or R.sup.d and R.sup.e together form a (3-4C)alkylene chain, R.sup.f 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, R.sup.g is (1-6C) alkyl, hydroxy or (1-6C)alkoxy, R.sup.h is hydrogen or (1-6C)alkyl, R.sup.i is hydrogen, (1-6C)alkyl, optionally substituted phenyl or an optionally substituted 5- or 6-membered heteroaryl and R.sup.j is hydrogen or (1-6C)alkyl;
• or R.sup.7 is of the formula R.sup.14 CH(R.sup.13)(CH.sub.2).sub.m -- wherein m is 0 or 1, R.sup.13 is fluoro, cyano, (1-4C)alkoxy, (1-4C)alkylsulfonyl, (1-4C)alkoxycarbonyl or hydroxy, (provided that when m is 0, R.sup.13 is not fluoro or hydroxy) and R.sup.14 is hydrogen or (1-4C)alkyl;
• wherein AR is optionally substituted phenyl, 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 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-benzodioxan-6-yl, sulfolan-3-yl, 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, (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;
• or an in-vivo-hydrolysable ester thereof.