# US 5,707,987 A · Carbapenem derivatives > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,707,987 A - Document ID: US5707987A - Status: Granted - Kind: A - Application number: 08/696,910 - Filed: 1996-08-23 - Granted: 1998-01-13 - Earliest claimed: 1994-02-25 - Assignees: Banyu Pharmaceutical Co., Ltd. - Inventors: Susumu Nakagawa; Hiroshi Fukatsu; Ryosuke Ushijima - Web page: https://patentgrep.com/patent/US5707987A ## CPC - C07D 477/20: Sulfur atoms - A61P 31/04: Antibacterial agents - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract A compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is a hydrogen atom or a negative charge, R.sup.3 is a hydrogen atom or a lower alkyl group, Ar is a phenyl group, a naphthyl group or a group of: ##STR2## (wherein each of A.sub.4 and A.sub.5 is a single bond, --NHSO.sub.2 -- or the like, and Het is a pyrrolinyl group, a 1,4-diazabicyclo›2.2.2!octanyl group or the like which may be substituted with a hydroxyl group, a carbamoyl lower alkyl group or the like) which may be substituted with a lower alkyl group, a lower alkylsulfamoyl group or the like which may be substituted with a hydroxyl group, a di-lower alkylsulfonyl group or the like; a hydroxyl group; a di-lower alkylsulfamoyl group or the like, each of A.sub.1, A.sub.2 and A.sub.3 is a single bond or a lower alkylene group which may be substituted with a lower alkyl group, a lower alkylsulfamoyl group or the like which may be substituted with a hydroxyl group, a di-lower alkylsulfamoyl group or the like; a pyridyl group or a pyridino group; and W is a sulfur atom, a single bond; or a pharmaceutically acceptable salt or ester; a process for its production and an antibacterial agent containing it as an active ingredient. ## Claims ### Claim 1 A compound of the formula: ##STR327## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is a hydrogen atom or a negative charge, R.sup.3 is a hydrogen atom or a lower alkyl group, Ar is a phenyl group, a naphthyl group or a group of: ##STR328## (wherein each of A.sub.4 and A.sub.5, which may be the same or different, is a single bond, a methylene group, an ethylene group, an oxygen atom, an imino group, a sulfur atom, a sulfonyl group, --CONH-- or --NHSO.sub.2 --, and Het is a pyrrolinyl group, a pyrrolyl group, an imidazolyl group, an imidazolio group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyridinio group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a benzothiazolyl group, an isoindolyl group, a quinuclidinyl group, a quinuclidinio group, a benzothiazol-1,1-dioxo-6-yl group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents, selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group, a di-lower alkylsulfamoyl group, a lower alkyl group, a hydroxy lower alkyl group and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylamino group, a lower alkoxy group, an aryloxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a carbamoyl lower alkylamino group, an aroylamino group, an amino lower alkyl group, an amino lower alkylcarbonyl amino group, a pyridyl group, a pyridylcarbonylamino group, a pyridiniocarbonylamino group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a sulfo group, an aminosulfonyl group, a lower alkylsulfonyl group and a di-lower alkylsulfonyl group, and a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a di-lower alkylcarbamoyl group, an arylcarbamoyl group, a piperazinocarbonyl group, an amino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a sulfamino group, a lower alkanoylamino group, an aralkylamino group, an aroylamino group, an arylsulfonylamino group, an amino lower alkylcarbonylamino group, a sulfamoyl group and a di-lower alkylsulfamoyl group, each of A.sub.1, A.sub.2 and A.sub.3, which may be same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group, and a pyridyl group and a pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W is a sulfur atom, a group of N-X (wherein X is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 2 (depends on 1) The compound according to claim 1, wherein W is a sulfur atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 3 (depends on 1) The compound according to claim 1, wherein W is a group of N-X (wherein X is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 4 (depends on 3) The compound according to claim 3, wherein W is a group of N-X (wherein X is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group); or a pharmaceutically acceptable salt or ester thereof. ### Claim 5 (depends on 3) The compound according to claim 3, wherein W is an oxygen atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 6 (depends on 3) The compound according to claim 3, wherein W is a group of CH(OH); or a pharmaceutically acceptable salt or ester thereof. ### Claim 7 (depends on 3) The compound according to claim 3, wherein W is a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 8 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR329## wherein R.sup.1a is a lower alkyl group, R.sup.2a is a hydrogen atom or a negative charge, R.sup.3a is a hydrogen atom, Ar.sub.a is a phenyl group, a naphthyl group or a group of: ##STR330## (wherein each of A.sub.4a and A.sub.5a, which may be the same or different, is a single bond, a methylene group or an ethylene group, and Het.sup.a is an imidazolio group, a pyridinio group, a morpholinyl group, a quinuclidinio group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a lower alkyl group, a hydroxy lower alkyl group and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a carboxyl group, a carbamoyl group, an amino group and a lower alkylamino group, and a hydroxyl group, a halogen atom, a carboxyl group, a carbamoyl group, an amino group and a sulfamoyl group, each of A.sub.1a, A.sub.2a and A.sub.3a, which may be the same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a carbamoyl group, an amino group, a lower alkylamino group and a lower alkylthio group, and a pyridyl group and a pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W.sub.a is a sulfur atom, a group of N-X.sub.a (wherein X.sub.a is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutical acceptable salt or ester thereof. ### Claim 9 (depends on 8) The compound according to claim 8, wherein W.sub.a is a sulfur atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 10 (depends on 8) The compound according to claim 8, wherein W.sub.a is a group of N-X.sub.a (wherein X.sub.a is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 11 (depends on 10) The compound according to claim 10, wherein W.sub.a is a group of N-X.sub.a (wherein X.sub.a is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group); or a pharmaceutically acceptable salt or ester thereof. ### Claim 12 (depends on 10) The compound according to claim 10, wherein W.sub.a is an oxygen atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 13 (depends on 10) The compound according to claim 10, wherein W.sub.a is a group of CH(OH); or a pharmaceutically acceptable salt or ester thereof. ### Claim 14 (depends on 10) The compound according to claim 10, wherein W.sub.a is a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 15 (depends on 8) The compound according to claim 8, which is represented by the formula: ##STR331## wherein R.sup.1b is a lower alkyl group, R.sup.2b is a hydrogen atom or a negative charge, R.sup.3b is a hydrogen atom, Ar.sub.b is a phenyl group, a naphthyl group or a group of: ##STR332## (wherein each of A.sub.4b and A.sub.5b, which may be the same or different, is a single bond, a methylene group or an ethylene group, and Het.sup.b is an imidazolio group or a 1,4-diazabicyclo›2,2,2!octanyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxy lower alkyl group and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of an amino group and a lower alkylamino group, and a halogen atom, a carbamoyl group and a sulfamoyl group, each of A.sub.1b, A.sub.2b and A.sub.3b, which may be the same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a carbamoyl group, an amino group and a lower alkylamino group, and a pyridyl group and a pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W.sub.b is a sulfur atom, a group of N-X.sub.b (wherein X.sub.b is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutical acceptable salt or ester thereof. ### Claim 16 (depends on 15) The compound according to claim 15, wherein W.sub.b is a sulfur atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 17 (depends on 15) The compound according to claim 15, wherein W.sub.b is a group of N-X.sub.b (wherein X.sub.b is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 18 (depends on 17) The compound according to claim 17, wherein W.sub.b is a group of N-X.sub.b (wherein X.sub.b is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group); or a pharmaceutically acceptable salt or ester thereof. ### Claim 19 (depends on 17) The compound according to claim 17, wherein W.sub.b is an oxygen atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 20 (depends on 17) The compound according to claim 17, wherein W.sub.b is a group of CH(OH); or a pharmaceutically acceptable salt or ester thereof. ### Claim 21 (depends on 17) The compound according to claim 17, wherein W.sub.b is a single bond; or a pharmaceutically acceptable salt or ester thereof. ### Claim 22 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR333## wherein R.sup.1c is a hydrogen atom or a lower alkyl group, R.sup.2c is a hydrogen atom or a negative charge, R.sup.3c is a hydrogen atom or a lower alkyl group, Ar.sub.c is a phenyl group, a naphthyl group or a group of: ##STR334## (wherein each of A.sub.4c and A.sub.5c, which may be the same or different, is a single bond, a methylene group, an oxygen atom, an imino group, a sulfur atom, a sulfonyl group, --CONH-- or --NHSO.sub.2 --, and Het.sup.c is a pyrrolinyl group, a pyrrolyl group, an imidazolyl group, an imidazolio group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyridinio group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a benzothiazolyl group, an isoindolyl group, a quinuclidinyl group, a quinuclidinio group, a benzothiazol-1,1-dioxo-6-yl group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, an aryloxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a carbamoyl lower alkylamino group, an aroylamino group, an amino lower alkyl group, an amino lower alkylcarbonylamino group, a pyridyl group, a pyridylcarbonylamino group, a pyridiniocarbonylamino group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a sulfo group, an aminosulfonyl group, a lower alkylsulfonyl group and a di-lower alkylsulfonyl group, and a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a di-lower alkylcarbamoyl group, an arylcarbamoyl group, a piperazinocarbonyl group, an amino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a sulfamino group, a lower alkanoylamino group, an aralkylamino group, an aroylamino group, an arylsulfonylamino group, an amino lower alkylcarbonylamino group, a sulfamoyl group and a di-lower alkylsulfamoyl group, each of A.sub.1c, A.sub.2c and A.sub.3c, which may be same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group, and a pyridyl group (wherein the pyridyl group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W.sub.c is a sulfur atom; or a pharmaceutically acceptable salt or ester thereof. ### Claim 23 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR335## wherein R.sup.1d is a hydrogen atom or a lower alkyl group, R.sup.2d is a hydrogen atom, R.sup.3d is a hydrogen atom or a lower alkyl group, each of R.sup.4d and R.sup.5d, which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a carbamoyl group or a sulfamoyl group, X.sub.d is a hydrogen atom, a lower alkyl group, a formyl group or a lower alkanoyl group, either either Y.sub.d or Z.sub.d is a hydrogen atom, the other is a group (d): ##STR336## (wherein each of R.sup.6d and R.sup.7d, which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.6d and R.sup.7d form a C.sub.2-6 alkylene group, and P.sub.d is an integer of from 0 to 3), each of A.sub.d and B.sub.d, which may be the same or different, is a phenyl group or a naphthyl group (provided that R.sup.5d, B.sub.d and Z.sub.d may form a hydrogen atom), m.sub.d is 1 or 2, and n.sub.d is 0 or 1 (provided that when Y.sub.d or Z.sub.d is a hydrogen atom, Z.sub.d and R.sup.5d, or Y.sub.d and R.sup.4d may form a nitrogen-containing 5 to 7-membered heterocyclic ring); or a pharmaceutically acceptable salt or ester thereof. ### Claim 24 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR337## wherein R.sup.1e is a hydrogen atom or a lower alkyl group, R.sup.2e is a hydrogen atom, R.sup.3e is a hydrogen atom or a lower alkyl group, each of R.sup.4e and R.sup.5e, which may be the same or different, is a hydrogen atom, a carbamoyl group or a sulfamoyl group, either Y.sub.e or Z.sub.e is a hydrogen atom, the other is a group (e): ##STR338## (wherein each of R.sup.6e and R.sup.7e, which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.6e and R.sup.7e form a C.sub.2-6 alkylene group, and p.sub.e is an integer of from 0 to 3), each of A.sub.e and B.sub.e, which may be the same or different, is a phenyl group or a naphthyl group (provided that R.sup.5e, B.sub.e and Z.sub.e may form a hydrogen atom), m.sub.e is 1 or 2, and n.sub.e is 0 or 1 (provided that when Y.sub.e or Z.sub.e is a hydrogen atom, Z.sub.e and R.sup.5e, or Y.sub.e and R.sup.4e may form a nitrogen-containing 5 to 7-membered heterocyclic ring); or a pharmaceutically acceptable salt or ester thereof. ### Claim 25 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR339## wherein R.sup.1f is a hydrogen atom or a lower alkyl group, R.sup.2f is a hydrogen atom, R.sup.3f is a hydrogen atom, a lower alkyl group or a lower alkenyl group, each of R.sup.4f and R.sup.5f, which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a carbamoyl group or a sulfamoyl group, either Y.sub.f or Z.sub.f is a hydrogen atom, the other is a group (f): ##STR340## (wherein each of R.sup.6f and R.sup.7f, which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.6f and R.sup.7f form a C.sub.2-6 alkylene group, and p.sub.f is an integer of from 0 to 3), each of A.sub.f and B.sub.f, which may be the same or different, is a phenyl group or a naphthyl group (provided that R.sup.5f, B.sub.f and Z.sub.f may form a hydrogen atom), and n.sub.f is an integer of from 1 to 3 (provided that when Y.sub.f or Z.sub.f is a hydrogen atom, Z.sub.f and R.sup.5f, or Y.sub.f and R.sup.4f may form a nitrogen-containing 5 to 7-membered heterocyclic ring); or a pharmaceutically acceptable salt or ester thereof. ### Claim 26 (depends on 1) The compound according to claim 1, which is represented by the formula: ##STR341## wherein R.sup.1g is a hydrogen atom or a lower alkyl group, R.sup.2g is a hydrogen atom, R.sup.3g is a hydrogen atom or a lower alkyl group, each of R.sup.4g and R.sup.5g, which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a carbamoyl group or a sulfamoyl group, either Y.sub.g or Z.sub.g is a hydrogen atom, the other is a group (g): ##STR342## (wherein each of R.sup.6g and R.sup.7g, which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.6g and R.sup.7g may form a C.sub.2-6 alkylene group, and p.sub.g is an integer of from 0 to 3), R.sup.8g is a hydrogen atom, each of A.sub.g and B.sub.g, which may be the same or different, is a phenyl group or a naphthyl group (provided that R.sup.5g, B.sub.g and Z.sub.g may form a hydrogen atom), mg is an integer of 1 or 2, and n.sub.g is an integer of 0 or 1 (provided that when Y.sub.g or Z.sub.g is a hydrogen atom, Z.sub.g and R.sup.5g, or Y.sub.g and R.sup.4g may form a nitrogen-containing 5 to 7-membered heterocyclic ring); or a pharmaceutically acceptable salt or ester thereof. ### Claim 27 (depends on 1) The compound according to claim 1, which is: (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylthio)phenylthiomethyl!pyrrolidin-3- ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›(3-aminomethyl-4-chlorophenyl)thiomethyl!pyrrolidi n-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›(4-aminomethyl-2-sulfamoylphenyl)thiomethyl!pyrrol idin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylcarbamoyl)phenylthiomethyl!pyrrolid in-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-››4-(2-aminoethylcarbamoyl)-2-sulfamoylphenyl!thiom ethyl!pyrrolidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3 -carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethyloxy)phenylthiomethyl!pyrrolidin-3-y lthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(3-aminopropionylamino)phenylthiomethyl!pyrrolid in-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylsulfonylamino)phenylthiomethyl!pyrr olidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxyli c acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-aminomethylphenylthiomethyl!pyrrolidin-3-ylthio! -6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylsulfamoyl)phenylthiomethyl!pyrrolid in-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(8-aminomethyl-2-naphthylmethylthiomethyl)pyrrolidi n-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(3-aminomethyl-5-glycylamino-2-naphthylmethylthiome thyl)pyrrolidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3- carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›(3-aminoethylsulfonylaminoethyl)-2-naphthylmethylt hiomethyl)pyrrolidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2- em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(3-aminomethyl-5-glycylaminomethyl-2-naphthylmethyl thiomethyl)pyrrolidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2 -em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›6-(4-carbamoylmethyl-l,4-diazabicyclo›2.2.2!octane dium-1-ylmethyl)-2-naphthylmethylthiomethyl!pyrrolidin-3-ylthio!-6-›(1R)-hy droxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›3-(4-carbamoylmethyl-1,4-diazabicyclo›2.2.2!octane dium-1-ylmethyl)-2-naphthylmethylthiomethyl!pyrrolidin-3-ylthio!-6-›(1R)-hy droxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenylaminomethyl)pyrrolidin-3-ylthio !-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethyl-1-naphthylaminomethyl)pyrrolidin-3-y lthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenoxymethyl)pyrrolidin-3-ylthio!-6- ›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenylethyl)pyrrolidin-3-ylthio!-6-›( 1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylbenzyl)pyrrolidin-3-ylthio!-6-›(1R)-h ydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethyl-1-naphthylmethyl)pyrrolidin-3-ylthio !-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio!-6-›(1R)-h ydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›(4-aminomethyl-5-phenylphenyl)hydroxymethyl!pyrrol idin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›(4-aminomethyl-1-naphthylmethyl)hydroxymethyl!pyrr olidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxyli c acid, (1R,5S,6S)-2-›(3S,5S)-5-›(4-aminomethylphenyl)hydroxymethyl!pyrrolidin-3-yl thio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid or (1R,5S,6S)-2-›(3S,5S)-5-›(5-aminomethyl-2-fluorophenyl)hydroxymethyl!pyrrol idin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid; or a pharmaceutically acceptable salt or ester thereof. ### Claim 28 (depends on 1) The compound according to claim 1, which is: (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylthio)phenylthiomethyl!pyrrolidin-3- ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-aminomethyl-2-sulfamoylphenyl)thiomethyl!pyrroli din-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylcarbamoyl)phenylthiomethyl!pyrrolid in-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-››4-(2-aminoethylcarbamoyl)-2-sulfamoylphenyl!thiom ethyl!pyrrolidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3 -carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-››4-(3-aminopropionylamino)phenylthiomethyl!pyrroli din-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylsulfonylamino)phenylthiomethyl!pyrr olidin-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxyli c acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-aminomethylphenylthiomethyl!pyrrolidin-3-ylthio! -6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›4-(2-aminoethylsulfamoyl)phenylthiomethyl!pyrrolid in-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(8-aminomethyl-2-naphthylmethylthiomethyl)pyrrolidi n-3-ylthio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-›6-(4-carbamoylmethyl-1,4-diazobicyclo›2.2.2!octane dium-1-ylmethyl)-2-naphthylmethylthiomethyl!pyrrolidin-3-ylthio!-6-›(1R)-hy droxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenylaminomethyl)pyrrolidin-3-ylthio !-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylbenzyl)pyrrolidin-3-ylthio!-6-›(1R)-h ydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid, (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio!-6-›(1R)-h ydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid or (1R,5S,6S)-2-›(3S,5S)-5-(4-aminomethylphenyl)hydroxymethyl!pyrrolidin-3-ylt hio!-6-›(1R)-hydroxyethyl!-1-methyl-1-carbapen-2-em-3-carboxylic acid; or a pharmaceutically acceptable salt or ester thereof. ### Claim 29 A process for producing a compound of the formula: ##STR343## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is a hydrogen atom or a negative charge, R.sup.3 is a hydrogen atom or a lower alkyl group, Ar is a phenyl group, a naphthyl group or a group of: ##STR344## (wherein each of A.sub.4 and A.sub.5, which may be the same or different, is a single bond, a methylene group, an ethylene group, an oxygen atom, an imino group, a sulfur atom, a sulfonyl group, --CONH-- or --NHSO.sub.2 --, and Het is a pyrrolinyl group, a pyrrolyl group, an imidazolyl group, an imidazolio group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyridinio group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a benzothiazolyl group, an isoindolyl group, a quinuclidinyl group, a quinuclidinio group, a benzothiazol-1,1-dioxo-6-yl group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents, selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group, a di-lower alkylsulfamoyl group, a lower alkyl group, a hydroxy lower alkyl group and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylamino group, a lower alkoxy group, an aryloxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a carbamoyl lower alkylamino group, an aroylamino group, an amino lower alkyl group, an amino lower alkylcarbonylamino group, a pyridyl group, a pyridylcarbonylamino group, a pyridiniocarbonylamino group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a sulfo group, an aminosulfonyl group, a lower alkylsulfonyl group and a di-lower alkylsulfonyl group, and a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a di-lower alkylcarbamoyl group, an arylcarbamoyl group, a piperazinocarbonyl group, an amino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a sulfamino group, a lower alkanoylamino group, an aralkylamino group, an aroylamino group, an arylsulfonylamino group, an amino lower alkylcarbonylamino group, a sulfamoyl group and a di-lower alkylsulfamoyl group, each of A.sub.1, A.sub.2 and A.sub.3, which may be same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group, and a pyridyl group and a pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W is a sulfur atom, a group of N-X (wherein X is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof, which comprises reacting a compound of the formula: ##STR345## wherein R.sup.1 is as defined above, R.sup.10 is a hydrogen atom or a hydroxyl-protecting group, and R.sup.20 is a hydrogen atom or a carboxyl-protecting group, or a reactive derivative thereof, with a compound of the formula: ##STR346## wherein R.sup.30 is a hydrogen atom, a lower alkyl group or an imino-protecting group, Ar.sub.0 is a phenyl group, a naphthyl group or a group of: ##STR347## (wherein each of A.sub.40 and A.sub.50, which may be the same or different, is a single bond, a methylene group, an ethylene group, an oxygen atom, an imino group which may be protected, a sulfur atom, a sulfonyl group, --CONH-- or --NHSO.sub.2 --, and Het.sup.0 is a pyrrolinyl group, a pyrrolyl group, an imidazolyl group, an imidazolio group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyridinio group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a pyrrolidinyl group, a piperidyl group, piperazinyl group, a morpholinyl group, a benzothiazolyl group, an isoindolyl group, a quinuclidinyl group, a quinuclidinio group, a benzthiazol-1,1-dioxo-6-yl group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group which may be protected, a halogen atom, a cyano group, a carboxyl group which may be protected, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group which may be protected, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group, a di-lower alkylsulfamoyl group, a lower alkyl group, a hydroxy lower alkyl group which may be protected and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylamino group, a lower alkoxy group, an aryloxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group which may be protected, a halogen atom, a cyano group, a carboxyl group which may be protected, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group which may be protected, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a carbamoyl lower alkylamino group, an aroylamino group, an amino lower alkyl group which may be protected, an amino lower alkylcarbonylamino group which may be protected, a pyridyl group, a pyridylcarbonylamino group, a pyridiniocarbonylamino group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a sulfo group, an aminosulfonyl group, a lower alkylsulfonyl group and a di-lower alkylsulfonyl group, and a hydroxyl group which may be protected, a halogen atom, a cyano group, a carboxyl group which may be protected, a lower alkoxycarbonyl group, a carbamoyl group, a di-lower alkylcarbamoyl group, an arylcarbamoyl group, a piperazinocarbonyl group, an amino group which may be protected, a di-lower alkylamino group, a tri-lower alkylammonio group, a sulfamino group, a lower alkanoylamino group, an aralkylamino group, an aroylamino group, an arylsulfonylamino group, an amino lower alkylcarbonylamino group which may be protected, a sulfamoyl group and a di-lower alkylsulfamoyl group, each of A.sub.10, A.sub.20 and A.sub.30, which may be the same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxy group which may be protected, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group which may be protected, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group, and a pyridyl group and pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group which may be protected and a carbamoyl lower alkyl group), and W.sub.0 is a sulfur atom, a group of N-X.sub.0 (wherein X.sub.0 is a hydrogen atom, an amino-protecting group, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OR.sup.8) (wherein R.sup.8 is a hydrogen atom or a hydroxyl-protecting group) or a single bond, to obtain a compound of the formula: ##STR348## wherein R.sup.1, R.sup.5, R.sup.20, R.sup.30, A.sub.10, A.sub.20, A.sub.30, Ar.sub.0 and W.sub.0 are as defined above, then if necessary, removing any protecting groups of the compound of the formula ›IV!, and if necessary, converting the compound thus obtained into a pharmaceutically acceptable salt or non-toxic ester thereof. ### Claim 30 An antibacterial agent containing, as an active ingredient, a compound of the formula: ##STR349## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 is a hydrogen atom or a negative charge, R.sup.3 is a hydrogen atom or a lower alkyl group, Ar is a phenyl group, a naphthyl group or a group of: ##STR350## (wherein each of A.sub.4 and A.sub.5, which may be the same or different, is a single bond, a methylene group, an ethylene group, an oxygen atom, an imino group, a sulfur atom, a sulfonyl group, --CONH-- or --NHSO.sub.2 --, and Het is a pyrrolinyl group, a pyrrolyl group, an imidazolyl group, an imidazolio group, a pyrazolyl group, a thiazolyl group, a pyridyl group, a pyridinio group, a pyrazinyl group, a quinolyl group, an isoquinolyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a benzothiazolyl group, an isoindolyl group, a quinuclidinyl group, a quinuclidinio group, a benzothiazol-1,1-dioxo-6-yl group or a 1,4-diazabicyclo›2.2.2!octanyl group which may be substituted with the same or different one to three substituents, selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group, a di-lower alkylsulfamoyl group, a lower alkyl group, a hydroxy lower alkyl group and a carbamoyl lower alkyl group) which may be substituted with the same or different one to five substituents selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylsulfonylamino group, a lower alkylamino group, a lower alkoxy group, an aryloxy group, a lower alkylthio group, a lower alkylsulfonyl group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a carbamoyl lower alkylamino group, an aroylamino group, an amino lower alkyl group, an amino lower alkylcarbonylamino group, a pyridyl group, a pyridylcarbonylamino group, a pyridiniocarbonylamino group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a sulfo group, an aminosulfonyl group, a lower alkylsulfonyl group and a di-lower alkylsulfonyl group, and a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a di-lower alkylcarbamoyl group, an arylcarbamoyl group, a piperazinocarbonyl group, an amino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a sulfamino group, a lower alkanoylamino group, an aralkylamino group, an aroylamino group, an arylsulfonylamino group, an amino lower alkylcarbonylamino group, a sulfamoyl group and a di-lower alkylsulfamoyl group, each of A.sub.1, A.sub.2 and A.sub.3, which may be same or different, is a single bond or a lower alkylene group which may be substituted with a substituent selected from the group consisting of a lower alkyl group, a lower alkylcarbamoyl group, a lower alkylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkylsulfonylamino group and a lower alkylsulfamoyl group which may be substituted with the same or different one to three substituents selected from the group consisting of a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, a di-lower alkylcarbamoyl group, a carbamoyloxy group, an amino group, a lower alkylamino group, a di-lower alkylamino group, a tri-lower alkylammonio group, a formimidoylamino group, an acetimidoylamino group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a sulfo group, a sulfamoyl group, a lower alkylsulfamoyl group and a di-lower alkylsulfamoyl group, and a pyridyl group and a pyridinio group (wherein the pyridyl group and the pyridinio group may be substituted with a substituent selected from the group consisting of a lower alkyl group, a carboxy lower alkyl group and a carbamoyl lower alkyl group), and W is a sulfur atom, a group of N-X (wherein X is a hydrogen atom, a lower alkyl group, a formyl group, a lower alkanoyl group or a sulfamoyl group), an oxygen atom, a group of CH(OH) or a single bond; or a pharmaceutically acceptable salt or ester thereof.