# US 2010/0168418 A1 · Novel nitrogenated heterocyclic compound and salt thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0168418 A1 - Document ID: US20100168418A1 - Status: Published application - Kind: A1 - Application number: 11/993,652 - Filed: 2006-06-22 - Published: 2010-07-01 - Earliest claimed: 2005-06-24 - Assignees: Toyama Chemical Co., Ltd.; Taisho Pharmaceutical Co., Ltd. - Inventors: Taro Kiyoto; Tadashi Tanaka; Yasuhiro Tsutsui; Junichi Ando; Mai Motono; Yasuko Kawaguchi; Toshiya Noguchi; Yasunobu Ushiki; Fumihito Ushiyama; Hiroki Urabe - Web page: https://patentgrep.com/patent/US20100168418A1 ## CPC - C07D 405/14: containing three or more hetero rings - A61P 31/04: Antibacterial agents - C07D 215/227: only one oxygen atom which is attached in position 2 - C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms - C07D 401/14: containing three or more hetero rings - C07D 405/12: linked by a chain containing hetero atoms as chain links - C07D 409/14: containing three or more hetero rings - C07D 413/14: containing three or more hetero rings - C07D 471/04: Ortho-condensed systems - C07D 491/04: Ortho-condensed systems - C07D 495/04: Ortho-condensed systems - C07D 513/04: Ortho-condensed systems - C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract A nitrogen-containing heterocyclic compound represented by the general formula: wherein the dashed line represents a single bond or a double bond; R1, R2, R3, R4 and R5 independently represent a hydrogen atom, halogen atom, a lower alkyl, aryl, lower alkoxy or monocyclic heterocyclic group which may be substituted or the like; R6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted; X1 represents a lower alkylene group or the like; X2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted; X3 represents an oxygen atom, sulfur atom, a sulfinyl group, sulfonyl group or the like; Y1 represents a bivalent cyclic group, containing a nitrogen, which may be substituted or the like; and Z1 represents a nitrogen atom, a carbon atom which may be substituted or the like, or a salt thereof. The compound or salt has a potent antibacterial activity and a high safety, and is therefore useful as an excellent antibacterial agent. ## Claims ### Claim 1 A compound represented by the general formula: wherein the dashed line represents a single bond or a double bond; R1, R2, R3, R4 and R5 are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a formyl group, an amino group which may be protected or substituted, a lower alkyl, cycloalkyl, aryl, lower alkoxy, cycloalkyloxy, aralkyloxy, alkanoyl, ureido or monocyclic heterocyclic group which may be substituted or a group represented by the general formula -Q1-CONR7R8, -Q1-CO2R9 or -Q1-CN (wherein R7 and R8 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R7 and R8, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R9 represents a hydrogen atom or a carboxyl protective group; Q1 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); R6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted; X1 represents a lower alkylene group which may be substituted with one or more groups selected from a hydroxyl and a carboxyl groups which may be protected, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxy group and an aryl group; X2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted; X3 represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a group represented by the general formula NR10 (wherein R10 represents a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group) or a bond; Y1 represents a group represented by the general formula (wherein R11, R11a, R24 and R24a are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, an amino, lower alkyl or lower alkoxy group which may be substituted, an oxo group or a group represented by the general formula -Q2-CONR14R15, -Q2-CO2R16 or -Q2-CN (wherein R14 and R15 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R14 and R15, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R16 represents a hydrogen atom or a carboxyl protective group; Q2 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); R12 and R12a are the same or different and represent a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group; R13 represents a halogen atom, a hydroxyl group, an amino, lower alkyl or lower alkoxy group which may be substituted, an oxo group or a group represented by the general formula -Q3-CONR17R18, -Q3-CO2R19 or -Q3-CN (wherein R17 and R18 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R17 and R18, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R19 represents a hydrogen atom or a carboxyl protective group; Q3 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); or R11 and R24 together and R12a and R24 together represent a lower alkylene group which may be substituted); Z1 represents (1) when the dashed line represents a double bond, a nitrogen atom or a group represented by the general formula CR20 (wherein R20 represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a formyl group, an amino group which may be protected or substituted, a lower alkyl, cycloalkyl, aryl, lower alkoxy, cycloalkyloxy, aralkyloxy, alkanoyl, ureido or monocyclic heterocyclic group which may be substituted or a group represented by the general formula -Q4-CONR21R22, -Q4-CO2R23 or -Q4-CN (wherein R21 and R22 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R21 and R22, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R23 represents a hydrogen atom or a carboxyl protective group; Q4 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond)); (2) when the dashed line represents a single bond, a group represented by the general formula NR40 (wherein R40 represents a hydrogen atom, a hydroxyl group, a lower alkyl, cycloalkyl, lower alkenyl, lower alkynyl, aryl, lower alkoxy, cycloalkyloxy or monocyclic heterocyclic group which may be substituted or an imino protective group) or a group represented by the general formula CHR20 (wherein R20 is as defined above), or a salt thereof. ### Claim 2 (depends on 1) The compound or a salt thereof according to claim 1, wherein the dashed line represents a double bond. ### Claim 3 (depends on 1, 2) The compound or a salt thereof according to any one of claims 1 to 2, wherein Y1 represents a group represented by the general formula wherein R11, R11a, R24 and R24a are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, an amino, lower alkyl or lower alkoxy group which may be substituted, an oxo group or a group represented by the general formula -Q2-CONR14R15, -Q2-CO2R16 or -Q2-CN (wherein R14 and R15 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R14 and R15, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R16 represents a hydrogen atom or a carboxyl protective group; Q2 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); R12 represents a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group; R13 represents a halogen atom, a hydroxyl group, an amino, lower alkyl or lower alkoxy group which may be substituted, an oxo group or a group represented by the general formula -Q3-CONR17R18, -Q3-CO2R19 or -Q3-CN (wherein R17 and R18 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R17 and R18, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R19 represents a hydrogen atom or a carboxyl protective group; Q3 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); or R11 and R24 together represent a lower alkylene group which may be substituted. ### Claim 4 (depends on 1, 2, 3) The compound or a salt thereof according to any one of claims 1 to 3, wherein Y1 represents a group represented by the general formula wherein R11b and R24b are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, an amino, lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q2-CONR14R15, -Q2-CO2R16 or -Q2-CN (wherein R14 and R15 are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl, aryl, lower alkoxy, alkanesulfonyl or monocyclic heterocyclic group which may be substituted, or R14 and R15, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R16 represents a hydrogen atom or a carboxyl protective group; Q2 represents a lower alkylene or lower alkenylene group which may be substituted, a lower oxyalkylene group which is attached to the ring via a terminal oxygen atom and which may be substituted or a bond); R12 represents a hydrogen atom, a lower alkyl or lower alkynyl group which may be substituted or an imino protective group; R13a represents a group represented by the general formula -Q3a-CONR17aR18a or -Q3a-CO2R19 (wherein R17a and R18a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R17a and R18a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R19 represents a hydrogen atom or a carboxyl protective group; Q3a represents a lower alkylene or lower alkenylene group which may be substituted or a bond). ### Claim 5 (depends on 1, 2, 3, 4) The compound or a salt thereof according to any one of claims 1 to 4, wherein the dashed line represents a double bond; R1, R2, R3, R4 and R5 are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an amino, lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q1a-CONR7aR8al or -Q1a-CO2R9 (wherein R7a and R8a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R7a and R8a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R9 represents a hydrogen atom or a carboxyl protective group; Q1a represents a lower alkylene or lower alkenylene group which may be substituted or a bond); R6 represents an aryl, monocyclic heterocyclic or bicyclic heterocyclic group which may be substituted; X2 represents a lower alkylene group which may be substituted; X3 represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, a group represented by the general formula NR10a (wherein R10a represents a hydrogen atom, a lower alkyl group which may be substituted or an imino protective group) or a bond; Y1 represents a group represented by the general formula (wherein R11c and R24c are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an amino, lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q2a-CONR14aR15a or -Q2a-CO2R16 (wherein R14a and R15a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R14a and R15a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R16 represents a hydrogen atom or a carboxyl protective group; Q2a represents a lower alkylene or lower alkenylene group which may be substituted or a bond); R12b represents a hydrogen atom, a lower alkyl group which may be substituted or an imino protective group; R13a represents a group represented by the general formula -Q3a-CONR17aR18a or -Q3a-CO2R19 (wherein R17a and R18a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R17a and R18a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R19 represents a hydrogen atom or a carboxyl protective group; Q3a represents a lower alkylene or lower alkenylene group which may be substituted or a bond)); Z1 represents a nitrogen atom or a group represented by the general formula CR20a (wherein R20a represents a hydrogen atom, a hydroxyl group, a cyano group, an amino, lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q4a-CONR21aR22a or -Q4a-CO2 R23 (wherein R21a and R22a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R21a and R22a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R23 represents a hydrogen atom or a carboxyl protective group; Q4a represents a lower alkylene or lower alkenylene group which may be substituted or a bond)). ### Claim 6 (depends on 1, 2, 3, 4, 5) The compound or a salt thereof according to any one of claims 1 to 5, wherein X1 represents a methylene group, an ethylene group or a propylene group; X2 represents a methylene, ethylene or propylene group which may be substituted. ### Claim 7 (depends on 1, 2, 3, 4, 5, 6) The compound or a salt thereof according to any one of claims 1 to 6, wherein R1, R2, R3, R4 and R5 are the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q1a-CONR7aR8a, wherein R7a and R8a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R7a and R8a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted represents a lower alkylene or lower alkenylene group which may be substituted or a bond. ### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7) The compound or a salt thereof according to any one of claims 1 to 7, wherein R1 represents a hydrogen atom or a lower alkyl group. ### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8) The compound or a salt thereof according to any one of claims 1 to 8, wherein R2, R3, R4 and R5 are the same or different and represent a hydrogen atom, a halogen atom or a lower alkoxy group which may be substituted. ### Claim 10 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9) The compound or a salt thereof according to any one of claims 1 to 9, wherein Y1 represents a group represented by the general formula wherein R11c and R24c are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an amino, lower alkyl or lower alkoxy group which may be substituted or a group represented by the general formula -Q2a-CONR14aR15a or -Q2a-CO2R16 (wherein R14a and R15a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R14a and R15a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R16 represents a hydrogen atom or a carboxyl protective group; Q2a represents a lower alkylene or lower alkenylene group which may be substituted or a bond); R12b represents a hydrogen atom, a lower alkyl group which may be substituted or an imino protective group; R13a represents a group represented by the general formula -Q3a-CONR17aR18a or -Q3a-CO2R19 (wherein R17a and R18a are the same or different and represent a hydrogen atom, a lower alkyl, cycloalkyl, aralkyl or aryl group which may be substituted, or R17a and R18a, together with the nitrogen atom to which they are attached, represent a cyclic amino group which may be substituted; R19 represents a hydrogen atom or a carboxyl protective group; Q3a represents a lower alkylene or lower alkenylene group which may be substituted or a bond). ### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10) The compound or a salt thereof according to any one of claims 1 to 10, wherein Y1 represents a group represented by the general formula wherein R11d represents a hydrogen atom, a halogen atom or a group represented by the general formula —CONR14bR15b or —CO2R16, wherein R14b and R15b are the same or different and represent a hydrogen atom or a lower alkyl group; R16 represents a hydrogen atom or a carboxyl protective group. ### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) The compound or a salt thereof according to any one of claims 1 to 11, wherein the dashed line represents a double bond; Z1 represents a nitrogen atom. ### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) An antibacterial agent comprising the compound or a salt thereof according to any one of claims 1 to 12.