Claims
- 1. A compound of the formula: ##STR36## wherein: R is H or CH.sub.3 ;
- P' is: a readily removable protecting group for hydroxy;
- R.sup.a and R.sup.b, are independently selected from the group consisting of hydrogen and the radicals set out below:
- 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, --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)R.sup.s, 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;
- 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)--, --S(O).sub.2 -- or --NR.sup.e --, to form a ring (where R.sup.e is hydrogen, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.4 alkyl mono-substituted with R.sup.q and the ring is optionally mono-substituted with 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 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(R.sup.t)(C.dbd.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) a (C.sub.1 -C.sub.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;
- l) 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.dbd.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 define 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(OM.sup.b)N(R.sup.y)R.sup.z) and P.dbd.O(OM.sup.b)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 NM.sup.b CON(R.sup.y)R.sup.z ; and SO.sub.2 NM.sup.b CN, where
- R.sup.x is phenyl; M.sup.b is as defined above; and R.sup.y and R.sup.z are as defined above;
- ac) C.sub.2 -C.sub.4 alkenyl radical, optionally mono-substituted by one of the substituents a) to ab) above and phenyl which is optionally substituted by R.sup.q as defined above;
- ad) C.sub.2 -C.sub.4 alkynyl radical, optionally mono-substituted by one of the substituents a) to ab) above;
- ae) C.sub.1 -C.sub.4 alkyl radical;
- af) C.sub.1 -C.sub.4 alkyl mono-substituted by one of the substituents a)-ab) above;
- ag) 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 af) above;
- R.sup.c is hydrogen, C.sub.1 -C.sub.6 alkyl or R.sup.q defined hereinabove;
- R.sup.d is hydrogen, NH.sub.2, O or C.sub.1 -C.sub.4 alkyl (where the alkyl group is optionally mono-substituted with R.sup.q as defined above);
- A is para (p) or meta (m) with respect to the point of attachment of the phenyl ring to the carbapenem nucleus, and is (CH.sub.2).sub.m --Q--(CH.sub.2).sub.n, where m is 1 to 2 and n is 0 to 2; and Q is O(C.dbd.O) or NR.sup.g ; where R.sup.g is hydrogen or C.sub.1 -C.sub.6 alkyl; ##STR37## is selected from the group consisting of: ##STR38## wherein R.sup.c and R.sup.d are as defined above; Y is --COOY' where Y' is readily removable protecting group for carboxy and --COOY' is not a pharmaceutically acceptable ester; and R.sup.a, R.sup.b, R.sup.c and R.sup.d are defined above.
- 2. The compound of claim 1 wherein R.sup.c is hydrogen and R.sup.d is hydrogen.
- 3. The compound of claim 1 wherein P' is selected from the group consisting of methoxy-t-butylphenylsilyl, t-butoxydiphenylsilyl, trimethylsilyl, triethylsilyl, o-nitrobenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, benzyloxycarbonyl, t-butyloxycarbonyl, 2,2,2-trichloroethyloxycarbonyl and allyloxycarbonyl.
Parent Case Info
This application is a continuation of Ser. No. 07/594,888, filed Oct. 9, 1990, now abandoned.
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Entry |
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Continuations (1)
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Number |
Date |
Country |
Parent |
594888 |
Oct 1990 |
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