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Details for Patent: 5,290,934

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Details for Patent: 5,290,934

Title: Benzoheterocyclic compounds
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.
Inventor(s): Ueda; Hiraki (Mishima, JP), Miyamoto; Hisashi (Tokushima, JP), Yamashita; Hiroshi (Tokushima, JP), Tone; Hitoshi (Tokushima, JP)
Assignee: Otsuka Pharmaceutical Company, Limited (Tokyo, JP)
Filing Date:Jun 04, 1991
Application Number:07/711,273
Claims:1. 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.

2. The compound according to claim 1, wherein R.sup.1 is a phenyl which is optionally substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkoxy group, a halogen atom and hydroxy group, or a C.sub.1 -C.sub.6 alkyl group which is optionally substituted by a halogen atom, a C.sub.2 -C.sub.6 alkanoyloxy group or hydroxy group, R.sup.14 is hydrogen atom, and X is fluorine atom or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1, wherein R.sup.1 is a C.sub.2 -C.sub.6 alkenyl group or thienyl group, R.sup.14 is hydrogen atom, and X is fluorine atom, or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1, wherein R.sup.1 is a cyclopropyl which is optionally unsubstituted or substituted by 1 to 3 of substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkyl and a halogen atom; a phenyl which is optionally unsubstituted or substituted by 1 to 3 of substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkoxy, a halogen atom and hydroxy; a C.sub.1 -C.sub.6 alkyl which is optionally unsubstituted or substituted by a halogen atom, a C.sub.2 -C.sub.6 alkanoyloxy or hydroxy; a C.sub.2 -C.sub.6 alkenyl; or thienyl,

R.sup.3 is a C.sub.1 -C.sub.6 alkyl,

R.sup.14 is hydrogen atom, a C.sub.1 -C.sub.6 alkyl, or a group of the formula: ##STR38## wherein R.sup.15 and R.sup.16 are each a C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 4, wherein R.sup.3 is methyl or ethyl, or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 5, wherein X is chlorine or fluorine atoms or a pharmaceutically acceptable salt thereof.

7. The compound according to claim 6, wherein R.sup.1 is unsubstituted cyclopropyl, or a pharmaceutically acceptable salt thereof.

8. The compound according to claim 6, wherein R.sup.1 is a phenyl which is optionally unsubstituted or substituted by 1 to 3 of substituents selected from the group consisting of a C.sub.1 -C.sub.6 alkoxy, a halogen atom and hydroxy; or a C.sub.1 -C.sub.6 alkyl which is optionally unsubstituted or substituted by a halogen atom, a C.sub.2 -C.sub.6 alkanoyloxy or hydroxy, or a pharmaceutically acceptable salt thereof.

9. The compound according to claim 6, wherein R.sup.1 is a C.sub.2 -C.sub.6 alkenyl or thienyl, or a pharmaceutically acceptable salt thereof.

10. The compound according to any one of claim 7, 8 or 9, wherein R.sup.14 is hydrogen atom, or a salt pharmaceutically acceptable thereof.

11. The compound according to any one of claim 7, 8 or 9, wherein R.sup.14 is a C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof.

12. The compound according to any one of claim 7, 8 or 9, wherein R.sup.14 is a group of the formula: ##STR39## wherein R.sup.15 and R.sup.16 are each a C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof.

13. Ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyl ate.

14. 1-Cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.

15. Ethyl 1-(4-fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-car boxylate.

16. 1-(4- Fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.

17. Ethyl 1-ethyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxylate.

18. 1-Ethyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxylic acid.

19. Ethyl 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinonline-3-carb oxylate.

20. 1-Cy clopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.

21. 1-C yclopropyl-6-fluoro-7-chloro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxy lic acid.

22. Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3 -carboxylate.

23. 1-(2,4-Di fluorophenyl)-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinonline-3-carboxyli c acid.

24. The compound according to claim 1, wherein R.sup.1 is unsubstituted cyclopropyl, R.sup.14 is hydrogen atom, X is fluorine atom and R.sup.3 is a methyl, or a pharmaceutically acceptable salt thereof.
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