Claims
- 1. A compound of the Formula I: ##STR201## or a pharmaceutically acceptable salt or solvate thereof, wherein: R.sup.13 represents hydrogen, NH.sub.2, C.sub.1-4 alkyl, C.sub.1-4 alkylamino or di(C.sub.1-4)alkylamino-;
- Y represents CH or N;
- Y" represents (a) CR.sup.y 'R.sup.z ', with R.sub.y ' and R.sup.z ' independently representing H, C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl or C.sub.1-6 alkyl substituted with C.sub.3-8 cycloalkyl, or (b) N substituted with --OR.sup.14 with R.sup.14 representing H, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl substituted with COOH;
- Ar represents ##STR202## wherein X represents --O-- or --S(O).sub.x -- wherein x is equal to 0, 1 or 2;
- one of R.sup.1 and R.sup.2 represents hydrogen, W as defined below or one of the groups (a) through (d) below, and the other represents H or W with the proviso that each R.sup.1 group is considered independently; ##STR203## when one of R.sup.1 and R.sup.2 represents (a) ##STR204## A represents --(CR.sup.3 'R.sup.4 ').sub.r --Q--(CR.sup.3 'R.sup.4 ').sub.s --wherein r represents an integer of from 0-6, s represents an integer of from 1-6 and Q represents: a covalent bond, --O--, --S(O).sub.x -- with x equal to 0, 1 or 2, --NR.sup.3 '--, --SO.sub.2 NR.sup.3 '--, --NR.sup.3 'SO.sub.2 --, --C(O)NR.sup.3 '--, --NR.sup.3 'C(O)--, --CR.sup.3 '.dbd.CR.sup.4 '--, --C(O)-- or --OC(O)--;
- with R.sup.3 ' and R.sup.4 ' independently representing H or C.sub.1-4 lower alkyl, and (CR.sup.3 'R.sup.4 ').sub.s -- being attached to the ring nitrogen; ##STR205## represents a 5 or 6 membered mono-cyclic heterocycle or an 8-10 membered bicyclic heterocycle, bonded to A through the ring nitrogen and having a substituent group R.sup.d optionally attached to the ring nitrogen, and having 0-3 R.sup.c groups attached to other atoms of the heterocyclic group, said ring nitrogen being tertiary or quaternary by virtue of the ring bonds and R.sup.d which may be optionally attached, said heterocyclic group being saturated or unsaturated, aromatic, partially aromatic or non-aromatic,
- said heterocycle also containing 0-3 additional nitrogen atoms and 0-1 oxygen or sulfur atom;
- each R.sup.c independently represents W as defined below or NR.sup.y R.sup.z, wherein R.sup.y and R.sup.z independently represent H, C1 to C4 alkyl, C1 to C4 alkyl substituted with R.sup.q or R.sup.y and R.sup.z are taken together to represent either a 3- to 5-membered alkylidene radical to form a ring, optionally substituted with R.sup.q, or a 2- to 4-membered alkylidene radical interrupted by O or S(O).sub.x with x equal to 0, 1 or 2, to form a ring, said alkylidene being optionally substituted with R.sup.q as defined below;
- each R.sup.d independently represents hydrogen, NH.sub.2, O-- or C1 to C4 alkyl, optionally mono-substituted with R.sup.q as defined below;
- R.sup.q is selected from hydroxy, methoxy, cyano, --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, --S(O)CH.sub.3, --SO.sub.2 CH.sub.3, --F, --CF.sub.3, --SO.sub.3 M.sup.b with M.sup.b representing H or alkali metal, or --CO.sub.2 M.sup.a, where M.sup.a is H, 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 optionally mono-substituted by another R.sup.q group as defined above);
- when one R.sup.1 and R.sup.2 represents (b) ##STR206## A' represents --(CR.sup.3 'R.sup.4 ').sub.m '--Q--(CR.sup.3 'R.sup.4 ').sub.m '-- with each m' independently equal to 0-6, and Q, R.sup.3 ' and R.sup.4 ' are as defined above, except that when each m' is 0, Q is not a covalent bond, and --(CR.sup.3 'R.sup.4 ').sub.m ' is attached to the phenyl ring; ##STR207## represents a 5 or 6 membered mono-cyclic heterocycle or an 8-10 membered bicyclic heterocycle, said heterocycle being unsaturated and aromatic, partially aromatic or non-aromatic, bonded to A' through an atom other than the ring nitrogen, and optionally having 0-2 R.sup.d substituent groups attached to the ring nitrogen, said nitrogen in the heterocycle being tertiary or quaternary by virtue of the ring bonds and the optional R.sup.d groups which may be attached;
- said heterocycle may further contain 0-1 oxygen or sulfur atom and 0-2 additional nitrogen atoms therein:
- R.sup.c and R.sup.d are as defined above;
- when one of R.sup.1 and R.sup.2 represents (c) --A.sub.p --NR.sup.10 R.sup.11 R.sup.12.sub.(0-1) ;
- A is as defined above and p is an integer 0 or 1;
- R.sup.10, R.sup.11 and where present, R.sup.12, are independently H, C.sub.1-4 alkyl or C.sub.1-4 alkyl optionally mono-substituted with R.sup.q ;
- or R.sup.10, R.sup.11 and R.sup.12 may be taken in combination to represent a C4 to C10 alkanetriyl group, optionally substituted with tip to three W groups, with W as defined below;
- such that the nitrogen atom to which said R.sup.10, R.sup.11 and R.sup.12 groups are attached is tertiary or quaternary;
- when one of R.sup.1 and R.sup.2 represents (d) ##STR208## A, p, R.sup.c and R.sup.d are as previously defined, and ##STR209## represents a saturated 5 or 6 membered mono-cyclic heterocycle or an 8-10 membered bicyclic heterocycle, bonded to A' through an atom other than the ring nitrogen, and having one or two R.sup.d substituent groups attached to the ring nitrogen, said nitrogen in the heterocycle being tertiary or quaternary by virtue of the ring bonds and the R.sup.d groups which may be attached;
- W represents a member selected from the group consisting of:
- a) trifluoromethyl group: --CF3;
- b) a halogen atom: --Br, --C1, --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 as defined above;
- d) a hydroxy group: --OH;
- e) a carbonyloxy radical: --OC(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; --OC(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), or are taken together to represent a 3- to 5-membered alkylidene radical which forms a ring (optionally substituted with R.sup.q as defined above), or a 2- to 4-membered alkylidene radical interrupted by --O--, --S--, --S(O)-- or --S(O).sub.2 -- which forms a ring, said ring being optionally mono-substituted with R.sup.q as defined above;
- g) a sulfur radical: --S(O).sub.n --R.sup.s, where n.dbd.O--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(O)H, where R.sup.t is H or C.sub.1-4 alkyl, said alkyl group being optionally mono-substituted with R.sup.q as defined above;
- k) an alkylcarbonylamino radical: --N(R.sup.t)C(O)C1-4 alkyl, wherein R.sup.t is as defined above;
- l) an alkoxycarbonylamino radical: --N(R.sup.t)C(O)OC.sub.1-4 alkyl, where R.sup.t is 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 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) an alkylcarbonyl radical wherein the carbonyl is acetalized: --C(OCH.sub.3).sub.2 C1-C4 alkyl, where the alkyl is optionally mono-substituted by R.sup.q as defined above;
- r) a 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.y and R.sup.z are as defined above, except they may not be joined together to form a ring;
- t) an alkoxycarbonyl 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 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.a where Ma 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.a).sub.2 ]; alkylphosphono {P.dbd.O(OM.sup.a)-[O(C1-C4 alkyl)]}; alkylphosphinyl [P.dbd.O(OM.sup.a)--(C.sub.1 -C.sub.4 alkyl)]; phosphoramido [P.dbd.O(OM.sup.a)N(R.sup.y)R.sup.z and P.dbd.O(OM.sup.a)NHR.sup.x ]; sulfino (SO.sub.2 M.sup.a); sulfo (SO.sub.3 M.sup.a); acylsulfonamides selected from the structures SO.sub.2 NM.sup.a CON(R.sup.y)R.sup.z ; and SO.sub.2 NM.sup.a CN, where R.sup.x is phenyl or heteroaryl, where heteroaryl is a mono-cyclic, aromatic hydrocarbon group having 5 or 6 ring atoms, in which a carbon atom 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 or S, and from 1 to 2 additional carbon atoms are optionally replaced by nitrogen heteroatoms, and where the phenyl and heteroaryl are optionally mono-substituted by R.sup.q, said R.sup.q, M.sup.a, R.sup.y and R.sup.z being as defined above;
- ac) a 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 may be replaced by the 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) a C.sub.2 -C.sub.4 alkenyl radical, optionally mono-substituted by one of the substituents a) to ac) above and phenyl which is optionally substituted by R.sup.q as defined above;
- ae) a C.sub.2 -C.sub.4 alkynyl radical, optionally mono-substituted by one of the substituents a) to ac) above;
- af) a C.sub.1 -C.sub.4 alkyl radical;
- ag) a C.sub.1 -C.sub.4 alkyl group mono-substituted by one of the substituents a)-ac) above;
- ah) a C.sub.1 -C.sub.6 alkyl group substituted with up to 3 groups selected from oxime (.dbd.N--OR.sup.14), cycloalkyl, aryl, heterocycloalkyl, heteroaryl and C.sub.1-3 alkoxy groups;
- ai) 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 represents hydrogen, a negative charge, a biolabile ester forming group, a carboxyl protecting group or a pharmaceutically acceptable cation.
- 2. The compound of claim 1, wherein one R.sup.1 group is selected from: ##STR210## in which A and A' represent --CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 CH.sub.2 --; ##STR211## and the point of attachment to --A'-- is other than a nitrogen heteroatom.
- 3. A compound of claim 1, wherein X represents --O-- or --S(O).sub.x with x equal to 0, 1 or 2, and the group --A'-- represents --(CH.sub.2).sub.m --X--(CH.sub.2).sub.n -- having the value: --CH.sub.2 --O--; --CH.sub.2 CH.sub.2 --; --CH.sub.2 NH--; --CH.sub.2 SO.sub.2 --; --CH.sub.2 C(O)-- or --CH.sub.2 OC(O)--.
- 4. A compound of claim 2, wherein one R.sup.1 variable represents group (a) or (b), one represents hydrogen, and one represents a member selected from the group consisting of:
- H; --CF.sub.3 ; --Br; --I; --Cl; --F; --OC.sub.1-4 alkyl; --OC.sub.1-4 alkyl substituted with 1-3 R.sup.q groups, which are independently selected from --OH, --OCH.sub.3, --CN, --F, --CF.sub.3, and --COOM.sup.a, where M.sup.a is H, alkali metal or methyl; --OH; --S(O).sub.x R.sup.s with x=0 or 2 and R.sup.s .dbd.C1-4 alkyl; --C2-4 alkenyl; --C.sub.2-4 alkynyl; --C.sub.1-4 alkyl substituted with --CF.sub.3, --Br, --I, --F, Cl or --OCH.sub.3 ; and --C(O)--C.sub.1-4 alkyl.
- 5. A compound of claim 2, wherein one R1 variable represents group (c) or (d), one represents hydrogen and one represents a member selected from the group consisting of:
- H; --CF.sub.3 ; --Br; --I; --Cl; --F; --OC.sub.1-4 alkyl; --OC.sub.1-4 alkyl substituted with 1-3 R.sup.q groups, which are independently selected from --OH, --OCH.sub.3, --CN, --F, --CF.sub.3, and --COOM.sup.a, where M.sup.a is H, alkali metal or methyl; --OH; --S(O).sub.x R.sup.s with x=0 or 2 and R.sup.s .dbd.C.sub.1-4 alkyl; --C2-4 alkenyl; --C2-4 alkynyl; --C1-4 alkyl substituted with --CF.sub.3, --Br, --I, --F, Cl or --OCH.sub.3 ; and --C(O)--C.sub.1-4 alkyl.
- 6. A compound of claim 1, wherein one R.sup.1 variable represents a substituent selected from: ##STR212## in which W' is O, S, NR', N(O)R.sup.e, SO or SO.sub.2, and where A'p- and R.sup.c are shown to have an indefinite position, they may be attached to any carbon atom of the ring.
- 7. A compound of claim 1, wherein one R.sup.1 group represents a member selected from the group consisting of: ##STR213## and where R.sup.c and/or A' is shown to have an indefinite position, they may be attached to any carbon atom of the ring.
- 8. A compound of claim 7, Wherein the R.sup.c substituents attached to ring carbon atoms are 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).sub.2,
- and the R.sup.d substituents attached to ring nitrogen atoms are 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).
- 9. A compound of claim 8 wherein the R.sup.d substituents attached to the nitrogen atom are 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 C(O)NH.sub.2, --CH.sub.2 SO.sub.2 NH.sub.2, --CH.sub.2 SO.sub.3 M.sup.b, --NH.sub.2 and --O--.
- 10. 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 --, --SO.sub.2 NHCH.sub.2 CH.sub.2 --, --COCH.sub.2 --, --CH.dbd.CHCH.sub.2 -- and --CH.sub.2 --O--CH.sub.2 CH.sub.2 --.
- 11. A compound of claim 1, wherein --A'--, is selected from the group consisting of:
- --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 --, --SO.sub.2 NHCH.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 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 --, --SO.sub.2 NHCH.sub.2 CH.sub.2 --, --COCH.sub.2 --, --CH.dbd.CHCH.sub.2 -- and --CH.sub.2 --O--CH.sub.2 CH.sub.2 --.
- 12. A compound of claim 1, wherein one of the R.sup.1 groups represents one of (a) through (d) and the other R.sup.1 groups are independently selected from:
- ______________________________________--OCH.sub.3--OCH.sub.2 CH.sub.2 OH --OCH.sub.2 CO.sub.2 Me--F --CF.sub.3--Br --Cl--OH --I--OCONH.sub.2 --OCOCH.sub.3--SOCH.sub.3 --SCH.sub.3--SCH.sub.2 CH.sub.2 OH --SO.sub.2 CH.sub.3--SO.sub.2 NH.sub.2 --SOCH.sub.2 CH.sub.2 OH--NHCHO --SO.sub.2 N(CH.sub.3).sub.2--NHCO.sub.2 CH.sub.3 --NHCOCH.sub.3--CN --NHSO.sub.2 CH.sub.3--COCH.sub.3 --CHO--CH.dbd.NOH --COCH.sub.2 OH--CH.dbd.NOCH.sub.2 CO.sub.2 Me --CH.dbd.NOCH.sub.3--SO.sub.2 CH.sub.2 CH.sub.2 OH --CH.dbd.NOCMe.sub.2 CO.sub.2 Me--CH.dbd.NOCMe.sub.2 CO.sub.2 Me --CO.sub.2 CH.sub.2 CH.sub.2 OH--CONH.sub.2 --CONHCH.sub.3--CON(CH.sub.3).sub.2 --CONHCH.sub.2 CN--CONHCH.sub.2 CONH.sub.2 --CONHCH.sub.2 CO.sub.2 Me--CONHOH --CONHCH.sub.3--tetrazolyl --CO.sub.2 Me--SCF.sub.3 --PO.sub.3 HMe--CONHSO.sub.2 Ph --CONHSO.sub.2 NH.sub.2--SO.sub.3 Me --SO.sub.2 NHCN--SO.sub.2 NHCONH.sub.2 --CH.dbd.CHCN--CH.dbd.CHCONH.sub.2 --CH.dbd.CHCO.sub.2 Me--CH.tbd.C--CONH.sub.2 --C.tbd.C--CN--CH.sub.2 OH --CH.sub.2 N.sub.3--CH.sub.2 CO.sub.2 Me and --CH.sub.2 I.______________________________________
- 13. A compound according to claim 1, wherein M is Na.sup.+, K.sup.+ or a negative charge.
- 14. A pharmaceutical composition comprising a compound of claim 1 in combination with a pharmaceutically acceptable carrier.
- 15. A method of treating a bacterial infection in a mammal in need of such treatment, comprising administering to said mammal a compound of claim 1 in an amount effective to treat said bacterial infection.
- 16. A pharmaceutical composition comprising a compound of claim 1 and a DHP inhibitor in combination with a pharmaceutically acceptable carrier.
- 17. A pharmaceutical composition according to claim 16 wherein the DHP inhibitor is 7-(L-2-amino-2-carboxyethylthio)-2-(2,2-dimethylcyclopropanecarboxamide)-2-heptenoic acid.
- 18. A method of treating a bacterial infection in a mammal in need of such treatment, comprising administering to said mammal an antibacterially effective amount of a compound of claim 1 and an inhibitorily effective amount of a DHP inhibitor.
- 19. A method according to claim 18, wherein the DHP inhibitor is 7-(L-2-amino-2-carboxyethylthio)-2-(2,2-dimethylcyclopropanecarboxamide)-2-heptenoic acid.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a divisional application of U.S. application Ser. No. 08/102,439 filed on Aug. 5, 1993, now U.S. Pat. No. 5,455,239, priority of which is claimed hereunder.
US Referenced Citations (23)
Foreign Referenced Citations (1)
Number |
Date |
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560365A1 |
Sep 1993 |
EPX |
Divisions (1)
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Number |
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Parent |
102439 |
Aug 1993 |
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