# US 4,399,134 A · Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,399,134 A - Document ID: US4399134A - Status: Granted - Kind: A - Application number: 06/320,027 - Filed: 1981-11-10 - Granted: 1983-08-16 - Earliest claimed: 1980-11-10 - Assignees: Otsuka Pharmaceutical Co., Ltd. - Inventors: Hiroshi Ishikawa; Testuyuki Uno; Masanobu Kano; Kazuyuki Nakagawa - Web page: https://patentgrep.com/patent/US4399134A ## CPC - C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide - A61P 31/04: Antibacterial agents - C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring - C07D 209/30: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring - C07D 211/46: having a hydrogen atom as the second substituent in position 4 - C07D 215/18: Halogen atoms or nitro radicals - C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18) - C07D 295/24: Oxygen atoms - C07D 455/04: containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine - C07D 471/06: Peri-condensed systems - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract A benzoheterocyclic compound of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and n are as defined, and its pharmaceutically acceptable salts, processes for preparing same and antibacterial composition containing the benzoheterocyclic compound as an active ingredient and a pharmaceutically acceptable carrier are disclosed. ## Claims ### Claim 1 A benzoheterocyclic compound of the formula (I) ##STR15## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a hydrogen atom or a halogen atom; R.sup.3 represents a 1-pyrrolidinyl group which may be substituted with a hydroxymethyl group, a 1,2,5,6-tetrahydro-1-pyridyl group, or a group of the formula ##STR16## where R.sup.4 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a phenyl-lower alkyl group, a lower alkanoyloxy group, an amino group which may be substituted with a lower alkyl group or a lower alkanoyl group, an oxo group, or a carbamoyl group; Z represents an oxygen atom, a sulfur atom or a methylene group; and m is 1 or 2; and n is an integer of 1 or 2; or its pharmaceutically acceptable salt. ### Claim 2 (depends on 1) A compound as claimed in claim 1, wherein n is 2. ### Claim 3 (depends on 1) A compound as claimed in claim 1, wherein n is 1. ### Claim 4 (depends on 2) A compound as claimed in claim 2, wherein R.sup.3 represents a group of the formula ##STR17## wherein Z, R and m have the same meanings as defined in claim 2. ### Claim 5 (depends on 2) A compound as claimed in claim 2, wherein R.sup.3 represents a 1-pyrrolidinyl group which may be substituted with a hydroxymethyl group or a 1,2,5,6-tetrahydro-1-pyridyl group. ### Claim 6 (depends on 4) A compound as claimed in claim 4, wherein R.sup.4 represents a hydrogen atom, a hydroxy group or a lower alkanoyloxy group and the position at which the group of the formula ##STR18## wherein Z, R.sup.4 and m have the same meanings as defined in claim 4, is attached is the 8-position. ### Claim 7 (depends on 4) A compound as claimed in claim 4, wherein R.sup.4 represents a lower alkyl group, a lower alkoxy group, a phenyl-lower alkyl group, an amino group which may be substituted with a lower alkyl group or a lower alkanoyl group, an oxo group, a carbamoyl group, and the position at which the group of the formula ##STR19## wherein Z, R.sup.4 and m have the same meanings as defined in claim 4, is attached is the 8-position. ### Claim 8 (depends on 6) A compound as claimed in claim 6, wherein R.sup.2 represents a halogen atom. ### Claim 9 (depends on 6) A compound as claimed in claim 6, wherein R.sup.2 represents a hydrogen atom. ### Claim 10 (depends on 8) A compound as claimed in claim 8, wherein R.sup.2 represents a fluorine atom and the position at which the fluorine atom is attached is the 9-position. ### Claim 11 (depends on 8) A compound as claimed in claim 8, wherein R.sup.2 represents a chlorine atom and the position at which the chlorine atom is attached is the 9-position. ### Claim 12 (depends on 10) A compound as claimed in claim 10, wherein R.sup.1 represents a lower alkyl group. ### Claim 13 (depends on 12) A compound as claimed in claim 12, wherein R.sup.1 represents a methyl group. ### Claim 14 (depends on 11) A compound as claimed in claim 11, wherein R.sup.1 represents a methyl group. ### Claim 15 (depends on 7) A compound as claimed in claim 7, wherein R.sup.2 represents a fluorine atom attached to the 9-position and R.sup.1 represents a methyl group. ### Claim 16 (depends on 5) A compound as claimed in claim 5, wherein R.sup.1 represents a methyl group, R.sup.2 represents a fluorine atom attached to the 9-position and the position at which the group represented by R.sup.3 is attached is the 8-position. ### Claim 17 (depends on 3) A compound as claimed in claim 3, wherein the position at which R.sup.3 is attached is the 9-position. ### Claim 18 (depends on 17) A compound as claimed in claim 17, wherein R.sup.1 represents a methyl group and R.sup.2 represents a fluorine atom attached to the 8-position. ### Claim 19 (depends on 17) A compound as claimed in claim 17, wherein R.sup.1 represents a methyl group and R.sup.2 represents a chlorine atom attached to the 8-position. ### Claim 20 (depends on 1) 9-Fluoro-8-(4-hydroxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-ben zo[ij]quinolizine-2-carboxylic acid as claimed in claim 1. ### Claim 21 (depends on 1) 9-Fluoro-8-(4-acetoxy-1-piperidyl)-5-methyl-6,7-dihydr o-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as claimed in claim 1. ### Claim 22 (depends on 1) 9-Fluoro-8-morpholino-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinoli zine-2-carboxylic acid as claimed in claim 1. ### Claim 23 An antibacterial composition comprising an antibacterially effective amount of a benzoheterocyclic compound of the formula (I) ##STR20## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a hydrogen atom or a halogen atom; R.sup.3 represents a 1-pyrrolidinyl group which may be substituted with a hydroxymethyl group, a 1,2,5,6-tetrahydro-1-pyridyl group, or a group of the formula ##STR21## where R.sup.4 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a phenyl-lower alkyl group, a lower alkanoyloxy group, an amino group which may be substituted with a lower alkyl group or a lower alkanoyl group, an oxo group, or a carbamoyl group; Z represents an oxygen atom, a sulfur atom or a methylene group; and m is 1 or 2; and n is an integer of 1 or 2; or its pharmaceutically acceptable salt, as an active ingredient and a pharmaceutically acceptable carrier.