Claims
- 1. A compound of the formula: ##STR172## wherein: X is O or S(O).sub.0-2 ;
- R is H or CH.sub.3 ;
- R.sup.1 and R.sup.2 are independently H, CH.sub.3 --, CH.sub.3 CH.sub.2 --, (CH.sub.3).sub.2 CH--, HOCH.sub.2 --, CH.sub.2 CH(OH)--, (CH.sub.3).sub.2 C(OH)--, FCH.sub.2 CH(OH)--, F.sub.2 CHCH(OH)--, F.sub.3 CCH(OH)--, CH.sub.3 CH(F)--, CH.sub.3 CF.sub.2 --, or (CH.sub.3).sub.2 C(F)--;
- R.sup.a and R.sup.b are independently selected from the group consisting of hydrogen and the radicals set out below provided that one but not more than one of R.sup.a or R.sup.b is selected from Type I substituents and in total not more than three R.sup.a and R.sup.b radicals are other than hydrogen:
- I.
- b) ##STR173## where A is (CH.sub.2).sub.m --Q--(CH.sub.2).sub.n, where m is 0 to 6 and n is 1 to 6 and Q is a covalent bond, O, S, SO, SO.sub.2, NH, --SO.sub.2 NH--, --NHSO.sub.2 --, --CONH--, --NHCO--, --SO.sub.2 N(C.sub.1 -C.sub.4 alkyl)--, --N(C.sub.1 -C.sub.4 alkyl)SO.sub.2 --, --CON(C.sub.1 -C.sub.4 alkyl)--, --N(C.sub.1 -C.sub.4 alkyl)CO--, --CH.dbd.CH--, --CO--, --OC(O)--, --C(O)Q-- or N(C.sub.1 -C.sub.4 alkyl) and (CH.sub.2).sub.m is attached to the dibenzofuranyl or dibenzothienyl moiety; ##STR174## is a 5- or 6-membered monocyclic heterocycle or an 8-, 9- or 10-membered bicyclic heterocycle, the heterocycle containing a first nitrogen in an aromatic 5- or 6-membered first ring, with attachment of the heterocycle to A by way of said first nitrogen and said first nitrogen is quaternary by virtue of the attachment in addition to the ring bonds thereto, with the first ring containing 0 or 1 of either O or S, with the first ring containing 0 to 3 additional nitrogen atoms, with the first ring optionally fused to a 3- or 4-membered moiety to form the optional second ring, with the moiety containing at least one carbon atom, with the moiety containing 0 or 1 of either O or S, with the moiety containing 0 to 2 nitrogen atoms, and with the moiety being saturated or unsaturated and the second ring aromatic or non-aromatic;
- R.sup.c is R.sup.a as defined under II below, hydrogen, or --NR.sup.y R.sup.z (where R.sup.y and R.sup.z are defined in II below), but independently selected from R.sup.a and from each other if more than one R.sup.c is present, and is attached to a carbon ring atom or a nitrogen heteroatom the valency of which is not satisfied by the ring bonds;
- b) ##STR175## where ##STR176## is a 5- or 6-membered monocyclic heterocycle or an 8-, 9- or 10-membered bicyclic heterocycle, the heterocycle containing a first nitrogen in an aromatic 5- or 6-membered first ring, with said first nitrogen either quaternary by virtue of a substituent R.sup.d in addition to the ring bonds thereto or neutral in the absence of a substituent R.sup.d, with attachment of the heterocycle to A' by way of a carbon atom of a ring, with the first ring containing 0 or 1 of either O or S, with the first ring containing 0 to 2 additional nitrogen atoms, with the first ring optionally fused to a 3- or 4-membered moiety to form the optional second ring, with the moiety containing at least one carbon atom, with the moiety containing 0 or 1 of either O or S, with the moiety containing 0 to 2 nitrogen atoms, and with the moiety being saturated or unsaturated and the second ring aromatic or non-aromatic;
- R.sup.c is defined above;
- R.sup.d is hydrogen, NH.sub.2, O.sup.- or C.sub.1 -C.sub.4 alkyl (where the alkyl group is optionally mono-substituted with R.sup.q as defined under IIc below) with the proviso that R.sup.d is present and is not H when either 1) m and n in A' below are both zero and Q is --OC.dbd.O, S, SO, SO.sub.2, --NHSO.sub.2, --N(C.sub.1 -C.sub.4 alkyl)SO.sub.2, or --CO, or 2) m+n in A' below is equal to or less than 2 and Q is CH.dbd.CH and ##STR177## is pyridinium, quinolinium, or, isoquinolinium; A' is (CH.sub.2).sub.m --Q--(CH.sub.2).sub.n, where m is 0 to 6 and n is 0 to 6, Q is as given above, except that when m and n are both 0 then Q is not a covalent bond, and (CH.sub.2).sub.m is attached to the dibenzofuranyl or dibenzothienyl moiety;
- c) -A.sub.p -N.sup.+ R.sup.y (R.sup.w).sub.(0-1) (R.sup.z) where
- R.sup.y and R.sup.z are as defined under II below,
- R.sup.y and R.sup.z may further be together a C.sub.2 -C.sub.4 alkylidene radical to form a ring (optionally mono-substituted with R.sup.q as defined below) interrupted by N(O)R.sup.e or N.sup.+ (R.sup.e).sub.2 (where R.sup.e is hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkyl mono-substituted with R.sup.q as defined below),
- R.sup.w is hydrogen, C.sub.1-4 alkyl, O.sup.-, NH.sub.2, or absent in which case the nitrogen is neutral,
- R.sup.w, R.sup.y and R.sup.z may further together form a C.sub.5 -C.sub.10 tertiary alkylidene radical which with N.sup.+ forms a bicyclic ring, where the tertiary alkylidene radical is optionally mono-substituted with R.sup.q as defined below and where the tertiary carbon of the tertiary alkylidene radical is optionally replaced with nitrogen, N.sup.+ R.sup.e (where R.sup.e is defined above), or N.sup.+ --O.sup.-,
- p is 0 or 1, and
- A is as defined above;
- d) ##STR178## where ##STR179## is a 5- or 6-membered monocyclic heterocycle or an 8-, 9- or 10-membered bicyclic heterocycle, the heterocycle containing a first nitrogen in a first ring, with the first ring saturated or unsaturated and non-aromatic, with the first nitrogen either quaternary by virtue of one or two substituents R.sup.d in addition to the ring bonds thereto or neutral by virtue of 0 or 1 substituent R.sup.d in addition to the ring bonds thereto, with attachment of the heterocycle to A' by way of a carbon atom or non-quaternary nitrogen atom of a ring, with the first ring containing in addition to carbon and the first nitrogen 0 to 1 of a member selected from the group consisting of the non-quaternary nitrogen of attachment, O, S, S(O), S(O).sub.2 and NR.sup.e where R.sup.e is defined above, with the first ring optionally fused to a 2-, 3- or 4-membered moiety to form the optional second ring, with the moiety optionally containing in addition to carbon the non-quaternary nitrogen of attachment, and with the moiety saturated or unsaturated and the second ring non-aromatic;
- R.sup.d is as defined above except without the proviso and where more than one R.sup.d is present on a nitrogen, at least one R.sup.d is hydrogen or C.sub.1 -C.sub.4 alkyl;
- A' is defined above;
- p is defined above; and
- R.sup.q is defined below;
- II.
- a) a trifluoromethyl group: --CF.sub.3 ;
- b) a halogen atom: --Br, --Cl, --F, or --I;
- 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, --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 or phenyl), 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);
- d) a hydroxy group: --OH;
- e) a carbonyloxy radical: --OC(O)R.sup.s, where
- R.sup.s is C.sub.1-4 alkyl, phenyl, or heteroaryl, each of which is optionally mono-substituted by R.sup.q as defined above, and where heteroaryl is a monocyclic aromatic hydrocarbon group having 5 or 6 ring atoms, in which a carbon is the point of attachment, one of the carbon atoms has been replaced by a nitrogen atom, one additional carbon atom is optionally replaced by a heteroatom selected from O and S, and from 1 to 3 additional carbon atoms are optionally replaced by a nitrogen heteroatom;
- f) a carbamoyloxy radical: --O(O)CN(R.sup.y)R.sup.z, where
- R.sup.y and R.sup.z are independently H, C.sub.1-4 alkyl, together a 3- or 5-membered alkylidene radical to form a ring, or together a 2- to 4-membered alkylidene radical, interrupted by --O--, --S--, --S(O)-- or --S(O).sub.2 --, to form a ring, and where R.sup.y or R.sup.z or both are defined as alkyl, including where joined together to form a ring, the alkyl is optionally mono-substituted by R.sup.q, as defined above;
- g) a sulfur radical: --S(O).sub.n --R.sup.s where n=0-2, and R.sup.s is as 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 formylamino group: --N(R.sup.t)--C(O)H, where
- R.sup.t is H or C.sub.1-4 alkyl, and the alkyl thereof is optionally mono-substituted by R.sup.q as defined above;
- k) (C.sub.1 -C.sub.4 alkyl)carbonylamino radical: --N(R.sup.t)--C(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;
- l) a (C.sub.1 -C.sub.4 alkoxy) carbonylamino radical: --N(R.sup.t)--C(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(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 --C(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(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.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(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(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(O)--N(OR.sup.y)R.sup.z where R.sup.y and R.sup.z are as defined above, except that they may not be joined together to form a ring;
- w) a thiocarbamoyl group: --C(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 alkaly 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(OM.sup.b)N(R.sup.y)R.sup.z and P.dbd.O(OM.sup.b)NHR.sup.s ]; 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.s, CONM.sup.b SO.sub.2 N(R.sup.y)R.sup.z, SO.sub.2 NM.sup.b CON(R.sup.y)R.sup.z ; and SO.sub.2 NM.sup.b CN, where R.sup.s, M.sup.b, 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 mono-substituted by one of the substituents a) to ac) above, or pyridyl, phenyl, quinoline, or isoquinoline each of which is optionally substituted by R.sup.q as defined above;
- ae) C.sub.2 -C.sub.4 alkynyl radical, optionally mono-substituted 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 form S and NRt (where Rt is as defined above) and one of the saturated carbon atoms of the oxazolidinone ring is optionally mono-substituted by one of the substitutents a) to ag) above;
- M is selected from:
- i) hydrogen;
- ii) a pharmaceutically acceptable esterifying group or removable carboxyl protecting group;
- iii) an alkali metal or other pharmaceutically acceptable cation; or
- iv) a negative charge which is balanced by a positively charged group.
- 2. A compound of claim 1 wherein R.sup.2 is H and R.sup.1 is (R)--CH.sub.3 CH(OH)-- or (R)--CH.sub.3 CH(F)--.
- 3. A compound of claim 2 wherein Z is in the (A.) configuration.
- 4. A compound of claim 1 wherein R.sup.2 is H, R.sup.1 is (R)--CH.sub.3 CH(OH)--, one of R.sup.a or R.sup.b is a Type I substituent and one or two R.sup.a and R.sup.b substituents are independently selected from the group consisting of: --CH.sub.3, --CH.sub.2 CH.sub.3, --(CH.sub.2).sub.3 CH.sub.3, --OCH.sub.3, --SCH.sub.3, tetrazolyl, --COOH, --CH.sub.2 CONH.sub.2, --CH.sub.2 CH.sub.2 SO.sub.3 H, --CONH.sub.2, --SO.sub.2 NH.sub.2, --SO.sub.3 H, --CON(CH.sub.3).sub.2, --CN, --CH.sub.2 CN, --CH.sub.2 SCH.sub.3, --CH.sub.2 SO.sub.3 H, --CH.sub.2 SOCH.sub.3, --SO.sub.2 CH.sub.3, --SOCH.sub.3, --CH.sub.2 OCH.sub.3, --N.sub.3, --OCONH.sub.2, --OH, --CHO, --CH.sub.2 P(O)(OCH.sub.3)OH, --CF.sub.3, --CH.sub.2 OC(O)NH.sub.2, --CH.sub.2 SO.sub.2 NH.sub.2, --SCH.sub.2 CH.sub.2 CN, Br, Cl, F, --SCF.sub.3, --CH.sub.2 SCF.sub.3, --SCH.sub.2 CF.sub.3, --COCH.sub.3, --CH.dbd.NOH, --CONHOH, --C(S)NH.sub.2, --OCOCH.sub.3, --NHCOCH.sub.3, --NHCO.sub.2 CH.sub.3, --NHCONH.sub.2, --NHSO.sub.2 CH.sub.3, --SCN, --CH.dbd.CHCHO, --SCH.sub.2 CH.sub.2 OH, --CH.sub.2 OH, --CH.dbd.NOCH.sub.2 CO.sub.2 H, --CO.sub.2 CH.sub.2 CH.sub.2 OH, and --SO.sub.2 NHCH.sub.2 CONH.sub.2.
- 5. A compound of claim 2 wherein the Type I. a) substituents are selected from the group consisting of: ##STR180## where X=O, S, or NR.sup.c.
- 6. A compound of claim 2 wherein the Type I. b) substituents are selected from the group consisting of: ##STR181## where X=O, S, or NR.sup.c and X'=O or S.
- 7. A compound of claim 2 wherein the Type I. c) substituents are selected from the group consisting of: ##STR182## where W is O, S, NR.sup.e, N(O)R.sup.e, SO, SO.sub.2 or N.sup.+ (R.sup.e).sub.2 and W' is N.sup.+ R.sup.e or NO.
- 8. A compound of claim 2 wherein the Type I. d) substituents are selected from the group consisting of: ##STR183##
- 9. A compound of claim 2 wherein R.sup.c, where attached to a ring carbon atom, is selected from the group consisting of --NH.sub.2, --SCH.sub.3, --SOCH.sub.3, --CH.sub.2 OH, --(CH.sub.2).sub.2 OH, --OCH.sub.3, --COOM.sup.b, --CH.sub.2 COOM.sup.b, --CH.sub.2 CH.sub.2 COOM.sup.b, --CH.sub.2 SOCH.sub.3, --CH.sub.2 SCH.sub.3, --SO.sub.3 M.sup.b, --CH.sub.2 SO.sub.3 M.sup.b, --CH.sub.2 CH.sub.2 SO.sub.3 M.sup.b, --Br, --Cl, --F, --I, --CH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 CONH.sub.2 and CH.sub.2 CON(C.sub.1 -C.sub.4 alkyl) where M.sup.b is defined above.
- 10. A compound of claim 2 wherein R.sup.c, where attached to a neutral ring nitrogen atom, is selected from the group consisting of --CH.sub.2 OH, --(CH.sub.2).sub.2 OH, --CH.sub.2 COOM.sup.b, --CH.sub.2 CH.sub.2 COOM.sup.b, --CH.sub.2 SOCH.sub.3, --CH.sub.2 SCH.sub.3, --CH.sub.2 SO.sub.3 M.sup.b, --CH.sub.2 CH.sub.2 SO.sub.3 M.sup.b, --CH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 CONH.sub.2 and CH.sub.2 CON(C.sub.1 -C.sub.4 alkyl) where M.sup.b is defined above.
- 11. A compound of claim 2 wherein R.sup.d is selected from the group consisting of hydrogen, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 COOM.sup.b, --CH.sub.2 SO.sub.3 M.sup.b, --NH.sub.2 and O.sup.(-), where M.sup.b is defined above.
- 12. A compound of claim 2 wherein A is selected from the group consisting of --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 --, --SOCH.sub.2 --, --SO.sub.2 CH.sub.2 --, --SCH.sub.2 CH.sub.2 --, --SOCH.sub.2 CH.sub.2 --, --SO.sub.2 CH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 --, --N(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --, --CONHCH.sub.2 CH.sub.2 --, --SO.sub.2 NHCH.sub.2 CH.sub.2 --, --COCH.sub.2 --, --CH.dbd.CHCH.sub.2 -- and --CH.sub.2 OCH.sub.2 CH.sub.2 --.
- 13. A compound of claim 2 wherein A' is selected from the group consisting of --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --OCH.sub.2 CH.sub.2 --, --SOCH.sub.2 --, --SO.sub.2 CH.sub.2 --, --SCH.sub.2 CH.sub.2 --, --SOCH.sub.2 CH.sub.2 --, --SO.sub.2 CH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 --, --N(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 N(CH.sub.3)CH.sub.2 CH.sub.2 --, --CONHCH.sub.2 CH.sub.2 --, --SO.sub.2 NHCH.sub.2 CH.sub.2 --, --COCH.sub.2 --, --CH.dbd.CHCH.sub.2 -- and --CH.sub.2 OCH.sub.2 CH.sub.2 --, --O--, --S--, --NH--, --SO.sub.2 --, --SO.sub.2 NH--, --CONH--, --CH.dbd.CH--, --CH.sub.2 S--, --CH.sub.2 NH--, --CONHCH.sub.2 -- and --SO.sub.2 NHCH.sub.2 --.
- 14. A compound ##STR184## wherein two of R.sup.a or R.sup.b are H and the third is as shown:
- ______________________________________M R.sup.a or R.sup.b X______________________________________(-) ##STR185## O, SO(-) ##STR186## O, SO(-) ##STR187## O, SO(-) ##STR188## O, SO(-) ##STR189## O, SO(-) ##STR190## O, SO(-) ##STR191## O, SO(-) ##STR192## O, SO(-) ##STR193## O, SO(-) ##STR194## O, SO(-) ##STR195## O, S, SO, SO.sub.2(-) ##STR196## O, S, SO, SO.sub.2(-) ##STR197## O, S, SO, SO.sub.2(-) ##STR198## O, S, SO, SO.sub.2(-) ##STR199## O, S, SO, SO.sub.2(-) ##STR200## O, S, SO, SO.sub.2(-) ##STR201## O, S, SO, SO.sub.2(-) ##STR202## O, S, SO, SO.sub.2(-) ##STR203## O, S, SO, SO.sub.2(-) ##STR204## O, S, SO, SO.sub.2 ##STR205## O, S, SO, SO.sub.2K ##STR206## O, S, SO, SO.sub.2K ##STR207## O, S, SO, SO.sub.2K ##STR208## O, S, SO, SO.sub.2(-) ##STR209## O, S, SO, SO.sub.2(-) ##STR210## O, SO(-) ##STR211## O, SO(-) ##STR212## O, SO(-) ##STR213## O, SO(-) 6-CH.sub.2.sup.+NH(CH.sub.3).sub.2 O, SO(-) 1-CO.sub.2 CH.sub.2 CH.sub.2.sup.+NH(CH.sub.3).sub.2 O, SO(-) ##STR214## O, SO(-) ##STR215## O, SO(-) ##STR216## O, SO(-) ##STR217## O, SO(-) ##STR218## O, SO(-) ##STR219## O, SO(-) ##STR220## O, SO(-) ##STR221## O, SO(-) ##STR222## O, SO(-) ##STR223## O, SO(-) ##STR224## O, SO(-) ##STR225## O, SO(-) ##STR226## O, SO(-) ##STR227## O, SO(-) ##STR228## O, SOH ##STR229## O, SO(-) ##STR230## O, SO(-) ##STR231## O, SO(-) ##STR232## O, SO(-) ##STR233## O, SO(-) ##STR234## O, SO(-) ##STR235## O, SOK ##STR236## O, SOK ##STR237## O, SO(-) ##STR238## O, SO(-) ##STR239## O, SO(-) ##STR240## O, SO(-) 8-CH.sub.2.sup.+N(CH.sub.3).sub.3 O, SO(-) ##STR241## O, SOK ##STR242## O, SOK ##STR243## O, SO(-) ##STR244## O, SO(-) ##STR245## O, SO(-) ##STR246## O, SOK ##STR247## O, S, SO, SO.sub.2K ##STR248## O, S, SO, SO.sub.2K ##STR249## O, S, SO, SO.sub.2K ##STR250## O, S, SO, SO.sub.2(-) ##STR251## O, SO______________________________________
- 15. A compound
- ______________________________________ ##STR252##M R.sup.a R.sup.b X______________________________________(--) CN ##STR253## O, S, SO, SO.sub.2(--) SOCH.sub.3 ##STR254## O, S, SO, SO.sub.2(--) CO.sub.2 K ##STR255## O, S, SO, SO.sub.2(--) CO.sub.2 K ##STR256## O, S, SO, SO.sub.2(--) ##STR257## ##STR258## O, S, SO, SO.sub.2(--) ##STR259## ##STR260## O, S, SO, SO.sub.2(--) SO.sub.3 K ##STR261## O, S, SO, SO.sub.2(--) CO.sub.2 K ##STR262## O, S, SO, SO.sub.2(--) SO.sub.3 K ##STR263## O, S, SO, SO.sub.2(--) SO.sub.3 K ##STR264## O, S, SO, SO.sub.2(--) CHO ##STR265## O, S, SO, SO.sub.2(--) CONH.sub.2 ##STR266## O, S, SO, SO.sub.2(--) SCH.sub.3 ##STR267## O, S, SO, SO.sub.2______________________________________
- 16. A pharmaceutical composition for antibacterial use comprising an antibacterially effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier therefor.
- 17. A method of treating bacterial infections in human or animal subjects in need of such treatment comprising administering to such subject an antibacterially effective amount of a compound of claim 1.
- 18. The combination of a compound of claim 1 and a DHP inhibitor.
- 19. The combination of a compound of claim 14 and the DHP inhibitor 7-(L-2-amino-2-carboxyethylthio)-2-(2,2-dimethylcyclopropanecarboxamide)-2-heptenoic acid.
- 20. The combination of a compound of claim 15 and the DHP inhibitor 7-(L-2-amino-2-carboxyethylthio)-2-(2,2-dimethylcyclopropanecarboxamide)-2-heptenoic acid.
- 21. A pharmaceutical composition for antibacterial use comprising an antibacterially effective amount of a compound of claim 1, an inhibitorily effective amount of a DHP inhibitor, and, optionally, a pharmaceutically acceptable carrier therefor.
- 22. A pharmaceutical composition according to claim 21 wherein the DHP inhibitor is 7-(L-2-amino-2-carboxyethylthio)-2-(2-dimethylcyclopropanecarboxyamide)-2-heptenoic acid.
- 23. A method of treating bacterial infections in human or animal subjects in need of such treatment comprising coadministering to such subject an antibacterially effective amount of a compound of claim 1 and an inhibitorily effective amount of a DHP inhibitor.
- 24. A method according to claim 23 wherein the DHP inhibitor is 7-(L-2-amino-2-carboxyethylthio)-2-(2,2-dimethylcyclopropanecarboxamide)-2-heptenoic acid.
Parent Case Info
This is a continuation of U.S. application Ser. No. 07/596,152, filed Oct. 11, 1990, now abandoned.
US Referenced Citations (4)
Continuations (1)
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Number |
Date |
Country |
Parent |
596152 |
Oct 1990 |
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