# US 5,703,081 A · Quinolonecarboxylic acid derivatives, their production and use

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- Number: US 5,703,081 A
- Document ID: US5703081A
- Status: Granted
- Kind: A
- Application number: 08/608,697
- Filed: 1996-02-29
- Granted: 1997-12-30
- Earliest claimed: 1993-03-09
- Assignees: Takeda Chemical Industries, Ltd.
- Inventors: Akio Miyake; Masahira Nakamura; Hideto Fukushi
- Web page: https://patentgrep.com/patent/US5703081A

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 215/56: with oxygen atoms in position 4
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 417/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 471/06: Peri-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A composition comprises a 1,7-disubstituted-4-oxo-3-quinolinecarboxylic acid or 1,7-disubstituted-4-oxo-3-naphthyridinecarboxylic acid derivative which is useful as a prophylactic and/or therapeutic agent for peripheral arterial obstruction, acute myocardial infarction, an antitumor agent, and as a prophylactic and/or therapeutic agent for osteoporosis.

## Claims

### Claim 1

A compound of the formula: ##STR197## wherein R.sup.1 is hydrogen or a carboxy protecting group; R.sup.3 is 4-(4-pyridyl)piperazin-1-yl group; 4-(4-piperidinyl)piperidin-1-yl group; or a group represented by the formula: ##STR198## wherein n.sup.3 is an integer of 1 to 4; n.sup.4 is 0 or 1; and n.sup.5 is a whole number 0 to 3; R.sup.14 and R.sup.15 are hydrogen or halogen; R.sup.17 is an optionally substituted phenyl group; or a salt thereof.

### Claim 2 (depends on 1)

A compound claimed in claim 1, wherein R.sup.3 is 4-(4-pyridyl)piperazin-1-yl group or 4-(4-piperidinyl)piperidin-1-yl group and R.sup.17 is a phenyl group which may be substituted with 1 to 3 substituents selected from hydroxy, lower alkoxy, halogen and trifluoromethyl.

### Claim 3

1-Benzyl-6,8-d ifluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

### Claim 4

1-(4-Chlorobenzyl)-6,8-difluoro-7-(1-piperazinyl)-1,4-dihydro-4-oxoq uinoline-3-carboxylic acid.

### Claim 5

6,8-Difluoro-1-(2-methox ybenzyl)-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

### Claim 6

1-(4-methoxybenzyl)-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carb oxylic acid or a salt thereof.

### Claim 7 (depends on 1)

A cell adhesion inhibitory composition which comprises a compound an claimed in claim 1 and a pharmaceutically acceptable carrier, diluent or excipient.

### Claim 8 (depends on 1)

A method for producing a compound as claimed in claim 1, which comprises reacting a compound of the formula: ##STR199## wherein R.sup.1 is hydrogen or a carboxyl protecting group; R.sup.14 and R.sup.15 are hydrogen or halogen; R.sup.17 is an optionally substituted phenyl group; and Y.sup.1 is halogen; or a salt thereof, with a compound of the formula:
R.sup.3 --H
wherein R.sup.3 is an organic group as defined in claim 1; or a salt thereof, to produce the compound as claimed in claim 1, or a salt thereof.