Benzoheterocyclic compounds
AssigneeOtsuka Pharmaceutical Co., Ltd.
InventorsHiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
Life of this patent
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Abstract
Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.
Claims24
A compound of the formula:
- ##STR36## wherein R.sup.1 is a cyclopropyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of a (lower) alkyl and a halogen atom, provided that when R.sup.1 is unsubstituted cyclopropyl R.sup.3 is methyl;
- a phenyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of a (lower) alkoxy, a halogen atom and hydroxy;
- a (lower) alkyl which is optionally substituted by a halogen atom, a (lower) alkanoyloxy or hydroxy;
- a (lower) alkenyl;
- or thienyl,
- R.sup.3 is a (lower) alkyl group,
- R.sup.14 is hydrogen atom, a lower alkyl group, or a group of the formula:
- ##STR37## wherein R.sup.15 and R.sup.16 are each a (lower) alkyl group, X is a halogen atom, and
- X.sup.4 is a halogen atom, or a pharmaceutically acceptable salt thereof.
Ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyl ate.
1-Cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.
Ethyl 1-(4-fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-car boxylate.
1-(4- Fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.
Ethyl 1-ethyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxylate.
1-Ethyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxylic acid.
Ethyl 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinonline-3-carb oxylate.
1-Cy clopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.
1-C yclopropyl-6-fluoro-7-chloro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxy lic acid.
Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3 -carboxylate.
1-(2,4-Di fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.
Dependencies are inferred from the claim text.