2-benzocoumarinyl carbapenems

A compound of the formula:

• ##STR39## wherein:
• R is H or CH.sub.3 ;
• X.sup.h is O or S;
• P' is a removable protecting group for hydroxy;
• R.sup.a are independently selected from the group consisting of hydrogen and the radicals set out below, provided that not more than four R.sup.a radicals are other than hydrogen:
• a) a trifluoromethyl group:
• --CF.sub.3 ;
• b) a halogen atom:
• --Br, --Cl, --F, or
• c) C.sub.1 -C.sub.4 alkoxy radical:
• --OC.sub.1-4 alkyl, wherein the alkyl is optionally mono-substituted by R.sup.q, where
• R.sup.q is a member selected from the group consisting of --OH, --OP', --OCH.sub.3, --CN, --C(O)NH.sub.2, --OC(O)NH.sub.2, CHO, --OC(O)N(CH.sub.3).sub.2, --SO.sub.2 NH.sub.2, --SO.sub.2 N(CH.sub.3).sub.2, --SOCH.sub.3, --SO.sub.2 CH.sub.3, --F, --CF.sub.3, --COOM.sup.a (where M.sup.a is hydrogen, alkali metal, methyl, phenyl or M defined below), tetrazolyl (where the point of attachment is the carbon atom of the tetrazole ring and one of the nitrogen atoms is mono-substituted by M.sup.a as defined above) and --SO.sub.3 M.sup.b (where M.sup.b is hydrogen or an alkali metal or M defined below);
• d) a hydroxy or protected hydroxy:
• --OH or --OP';
• e) a carbonyloxy radical:
• --O(C.dbd.O)Rs, where
• R.sup.s is C.sub.1-4 alkyl or phenyl, each of which is optionally mono-substituted by R.sup.q as defined above or tri-substituted with --F;
• f) a carbamoyloxy radical:
• --O(C.dbd.O)N(R.sup.y)R.sup.z where
• R.sup.y and R.sup.z are independently H, C.sub.1-4 alkyl (optionally mono-substituted by R.sup.q as defined above), together a 3- to 5-membered alkylidene radical to form a ring (optionally substituted with R.sup.q as defined above) or together a 2- to 4-membered alkylidene radical, interrupted by --O--, --S--, --S(O)-- or --S(O).sub.2 --, to form a ring (where the ring is optionally mono-substituted with R.sup.q as defined above);
• g) a sulfur radical:
• --S(O)n--Rs where n=0-2, and R.sup.s is defined above;
• h) a sulfamoyl group:
• --SO.sub.2 N(R.sup.y)R.sup.z where R.sup.y and R.sup.z are as defined above;
• i) azido:
• N.sub.3
• j) a formamido group:
• --N(Rt)(C.dbd.O)H, where
• R.sup.t is is H or C.sub.1-4 alkyl, and the alkyl thereof is optionally mono-substituted by R.sup.q as defined above;
• k) a (C.sub.1-4 alkyl)carbonylamino radical:
• --N(R.sup.t)(C.dbd.O)C.sub.1-4 alkyl where R.sup.t is as defined above, and the alkyl group is also optionally mono-substituted by R.sup.q as defined above;
• 1) a (C.sub.1 -C.sub.4 alkoxy) carbonylamino radical:
• --N(R.sup.t)(C.dbd.O)OC.sub.1-4 alkyl, where R.sup.t is as defined above, and the alkyl group is also optionally mono-substituted by R.sup.q as defined above;
• m) a ureido group:
• --N(R.sup.t)(C.dbd.O)N(R.sup.y)R.sup.z where R.sup.t, R.sup.y and R.sup.z are as defined above;
• n) a sulfonamido group:
• --N(R.sup.t)SO.sub.2 R.sup.s, where R.sup.s and R.sup.t are as defined above;
• o) a cyano group:
• --CN;
• p) a formyl or acetalized formyl radical:
• --(C=O)H or --CH(OCH.sub.3).sub.2 ;
• q) (C.sub.1 -C.sub.4 alkyl)carbonyl radical wherein the carbonyl is acetalized:
• --C(OCH.sub.3).sub.2 C.sub.1-4 alkyl, where the alkyl is optionally mono-substituted by R.sup.q as defined above;
• r) carbonyl radical:
• --(C.dbd.O)R.sup.s, where R.sup.s is as defined above;
• s) a hydroximinomethyl radical in which the oxygen or carbon atom is optionally substituted by a C.sub.1 -C.sub.4 alkyl group:
• --(C.dbd.NOR.sup.z)R.sup.y where R.sup.y and R.sup.z are as defined above, except they may not be joined together to form a ring;
• t) a (C.sub.1 -C.sub.4 alkoxy)carbonyl radical:
• --(C.dbd.O)OC.sub.1-4 alkyl, where the alkyl is optionally mono-substituted by R.sup.q as defined above;
• u) a carbamoyl radical:
• --(C.dbd.O)N(R.sup.y)R.sup.z where R.sup.y and R.sup.z are as defined above;
• v) an N-hydroxycarbamoyl or N(C.sub.1 -C.sub.4 alkoxy)carbamoyl radical in which the nitrogen atom may be additionally substituted by a C.sub.1 -C.sub.4 alkyl group:
• --(C.dbd.O)--N(OR.sup.y)R.sup.z where R.sup.y and R.sup.z are as defined above, except they may not be joined together to form a ring;
• w) a thiocarbamoyl group:
• --(C.dbd.S)N(R.sup.y)(R.sup.z) where R.sup.y and R.sup.z are as defined above;
• x) carboxyl:
• --COOM.sup.b, where M.sup.b is as defined above;
• y) thiocyanate:
• --SCN;
• z) trifluoromethylthio:
• --SCF.sub.3 ;
• aa) tetrazolyl, where the point of attachment is the carbon atom of the tetrazole ring and one of the nitrogen atoms is mono-substituted by hydrogen, an alkali metal or a C.sub.1 -C.sub.4 alkyl optionally substituted by R.sup.q as defined above;
• ab) an anionic function selected from the group consisting of:
• phosphono [P.dbd.O(OM.sup.b).sub.2 ];
• alkylphosphono {P.dbd.O(OM.sup.b)-[O(C.sub.1 -C.sub.4 alkyl)]};
• alkylphosphinyl [P.dbd.O(OM.sup.b)-(C.sub.1 -C.sub.4 alkyl)];
• phosphoramido [P.dbd.O(OMb)N(R.sup.y)R.sup.z and P.dbd.O(OMb)NHR.sup.x ];
• sulfino (SO.sub.2 M.sup.b);
• sulfo (SO.sub.3 M.sup.b);
• acylsulfonamides selected from the structures CONM.sup.b SO.sub.2 R.sup.x, CONM.sup.b SO.sub.2 N(R.sup.y)R.sup.z, SO.sub.2 .mu.LM.sup.b CON(R.sup.y)R.sup.z ;
• and SO.sub.2 NM.sup.b CN, where
• R.sup.x is phenyl or heteroaryl, where heteroaryl is a monocyclic aromatic hydrocarbon group having 5 or 6 ring atoms, in which a carbon atom is the point of attachment, in which one of the carbon atoms has been replaced by a nitrogen atom, in which one additional carbon atom is optionally replaced by a heteroatom selected from O or S, and in which from 1 to 2 additional carbon atoms are optionally replaced by a nitrogen heteroatom, and where the phenyl and heteroaryl are optionally mono-substituted by R.sup.q, as defined above;
• M.sup.b is as defined above;
• and R.sup.y and R.sup.z are as defined above;
• ac) C.sub.5 -C.sub.7 cycloalkyl group in which one of the carbon atoms in the ring is replaced by a heteroatom selected from O, S, NH or N(C.sub.1 -C.sub.4 alkyl) and in which one additional carbon atom may be replaced by NH or N(C.sub.1 -C.sub.4 alkyl), and in which at least one carbon atom adjacent to each nitrogen heteroatom has both of its attached hydrogen atoms replaced by one oxygen thus forming a carbonyl moiety and there are one or two carbonyl moieties present in the ring;
• ad) C.sub.2 -C.sub.4 alkenyl radical, optionally monosubstituted by one of the substituents a) to ac) above and phenyl which is optionally substituted by R.sup.q as defined above;
• ae) C.sub.2 -C.sub.4 alkynyl radical, optionally monosubstituted by one of the substituents a) to ac) above;
• af) C.sub.1 -C.sub.4 alkyl radical;
• ag) C.sub.1 -C.sub.4 alkyl mono-substituted by one of the substituents a)-ac) above;
• ah) a 2-oxazolidinonyl moiety in which the point of attachment is the nitrogen atom of the oxazolidinone ring, the ring oxygen atom is optionally replaced by a heteroatom selected from --S-- and NR.sup.t (where R.sup.t is as defined above) and one of the saturated carbon atoms of the oxazolidinone ring is optionally mono-substituted by one of the substituents a) to ag) above;
• and
• M is a removable protecting group for hydroxy.