Pyrroloquinoline and benzoquinolizine compounds and antimicrobial compositions

Claim 2

A benzoheterocyclic compound of the formula (I) ##STR15## wherein R 1 represents a hydrogen atom or a lower alkyl group; R 2 represents a hydrogen atom or a halogen atom; R 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 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 3

A compound as claimed in claim 1, wherein n is 2.

Claim 4

A compound as claimed in claim 1, wherein n is 1.

Claim 5

A compound as claimed in claim 2, wherein R 3 represents a group of the formula ##STR17## wherein Z, R and m have the same meanings as defined in claim 2.

Claim 6

A compound as claimed in claim 2, wherein R 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 7

A compound as claimed in claim 4, wherein R 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 4 and m have the same meanings as defined in claim 4, is attached is the 8-position.

Claim 8

A compound as claimed in claim 4, wherein R 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 4 and m have the same meanings as defined in claim 4, is attached is the 8-position.

Claim 9

A compound as claimed in claim 6, wherein R 2 represents a halogen atom.

Claim 10

A compound as claimed in claim 6, wherein R 2 represents a hydrogen atom.

Claim 11

A compound as claimed in claim 8, wherein R 2 represents a fluorine atom and the position at which the fluorine atom is attached is the 9-position.

Claim 12

A compound as claimed in claim 8, wherein R 2 represents a chlorine atom and the position at which the chlorine atom is attached is the 9-position.

Claim 13

A compound as claimed in claim 10, wherein R 1 represents a lower alkyl group.

Claim 14

A compound as claimed in claim 12, wherein R 1 represents a methyl group.

Claim 15

A compound as claimed in claim 11, wherein R 1 represents a methyl group.

Claim 16

A compound as claimed in claim 7, wherein R 2 represents a fluorine atom attached to the 9-position and R 1 represents a methyl group.

Claim 17

A compound as claimed in claim 5, wherein R 1 represents a methyl group, R 2 represents a fluorine atom attached to the 9-position and the position at which the group represented by R 3 is attached is the 8-position.

Claim 18

A compound as claimed in claim 3, wherein the position at which R 3 is attached is the 9-position.

Claim 19

A compound as claimed in claim 17, wherein R 1 represents a methyl group and R 2 represents a fluorine atom attached to the 8-position.

Claim 20

A compound as claimed in claim 17, wherein R 1 represents a methyl group and R 2 represents a chlorine atom attached to the 8-position.

Claim 21

9-Fluoro-8-(4-hydroxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as claimed in claim 1.

Claim 22

9-Fluoro-8-(4-acetoxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as claimed in claim 1.

Claim 23

9-Fluoro-8-morpholino-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as claimed in claim 1.

Claim 24

An antibacterial composition comprising an antibacterially effective amount of a benzoheterocyclic compound of the formula (I) ##STR20## wherein R 1 represents a hydrogen atom or a lower alkyl group; R 2 represents a hydrogen atom or a halogen atom; R 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 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.

Claim 25

An antibacterial composition comprising an antibacterially effective amount of a benzoheterocyclic compound of the formula (I) ##STR20## wherein R 1 represents a hydrogen atom or a lower alkyl group; R 2 represents a hydrogen atom or a halogen atom; R 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 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.