Claims
- 1. The compound which is structurally represented by the formula (IA): ##STR4## and therapeutically acceptable salts thereof wherein R.sub.1 is hydrogen or hydroxyl;
- Y is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, a phenyl, or a substituted phenyl wherein the substituent on the phenyl group is one, two or three of C.sub.1 -CH.sub.10 alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C.sub.2 -C.sub.4 alkylene wherein each carbon atom may be substituted with fluorine;
- R.sub.3 is hydrogen, halogen amine or hydroxyl;
- A.sub.1, A.sub.2, A.sub.3, A.sub.4 are independently hydrogen, hydroxyl, halogen, C.sub.1 -C.sub.4 alkyl, ethenyl, ethynyl, C.sub.3 -C.sub.6 cycloalkyl, fluoromethyl, difluoromethyl, difluoroethyl, trifluoromethyl, hydroxymethyl, C.sub.1 -C.sub.18 alkoxy methyl, phenoxymethyl, C.sub.1 -C.sub.3 alkyl aminomethyl, C.sub.1 -C.sub.3 dialkyl aminomethyl;
- R.sub.8 is hydrogen, hydroxyl, amine, C.sub.1 -C.sub.4 alkoxy or aryloxy, --SH, C.sub.1 -C.sub.6 thioalkyl or thioaryl;
- R.sub.9 is C.sub.1 -C.sub.4 alkyl ,C.sub.6 -C.sub.12 aryl, alkylaryl, --(CH.sub.2).sub.n --CO.sub.2 -(CH.sub.2).sub.m --R.sub.11, wherein R.sub.11 is hydrogen, hydroxyl, methyl, alkyloxy, aryloxy or an amine, n is 0-4 and m is 0-4;
- R.sub.12 is hydrogen, CN, halogen, or R.sub.9 ;
- Z is a fluorine substituted carbon;
- X is a carbon substituted with hydrogen, hydroxyl, cyano, nitro, halogen, C.sub.1 -C.sub.4 alkyl, or an amine.
- 2. The compound of claim 1 wherein X is a fluorine substitute carbon atom.
- 3. The compound of claim 2 wherein R.sub.3 is fluorine.
- 4. The compound of claim 1 wherein R.sub.8 is methoxy and R.sub.9 is a carbomethoxy group.
- 5. The compound of claim 1 which is
- a) 2-(4-(1-cyclopropyl-3-carboxy-6,8-difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butenedioic acid, dimethyl ester;
- b) 2-(4-(1-ethyl-3-carboxy-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butenedioic acid, dimethyl ester;
- c) 2-(4-(1-cyclopropyl-3-carboxy-5,6,8-trifluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butenedioic acid, dimethyl ester;
- d) 2-(4-(1-cyclopropyl-3-carboxy-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butenedioic acid, dimethyl ester;
- e) 2-(4-(3-carboxy-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-pentenedioic acid-(E)-1,5-dimethyl ester;
- f) 2-(4-(5-amino-3-carboxy-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butenedioic acid, (E)-1,4-dimethyl ester;
- g) 2-(4-(3-carboxy-1-cyclobutyl-6,8-difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2butenedioic acid, (E)-1,4-dimethyl ester; or
- h) 2-(4-(3-carboxy-1-benzene(4-fluoro)-6,8-difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2butenedioic acid, (E)-1,4-dimethyl ester.
- 6. A pharmaceutical composition comprising an antibacterially effective amount of a compound of Formula IA according to claim 1 in a mixture with a pharmaceutical carrier.
- 7. A method of treating bacterial infections in warm-blooded animals comprising administering to said animals an antibacterially effective amount of a compound of Formula IA in claim 1.
Parent Case Info
This application is a continuation-in-part of PCT/US89/05213, filed Nov. 24, 1989, which was a continuation in part of three U.S. patent applications: U.S. Ser. No. 07/411,449, filed Sep. 25, 1989, abandoned, U.S. Ser. No. 07/355,016, filed May 22, 1989, abandoned and U.S. Ser. No. 07/335,163, filed Apr. 7, 1989, abandoned. U.S. Ser. No. 07/335,016 was a continuation in part of U.S. Ser. No. 07/326,907 filed Mar. 22, 1989 abandoned. U.S. Ser. No. 07/335,163 was a continuation in part of U.S. Ser. No. 07/280,603 filed Dec. 6, 1988 abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US89/05213 |
11/24/1989 |
|
|
6/3/1991 |
6/3/1991 |
US Referenced Citations (21)
Foreign Referenced Citations (7)
Number |
Date |
Country |
0132845 |
Feb 1985 |
EPX |
0153163 |
Aug 1985 |
EPX |
3420743 |
Dec 1985 |
DEX |
WO8802627 |
Apr 1988 |
WOX |
853954 |
May 1985 |
ZAX |
8504767 |
Jul 1985 |
ESX |
2160519 |
Dec 1985 |
GBX |
Non-Patent Literature Citations (11)
Entry |
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Poster Abstract #962. |
Poster Abstract #963. |
Related Publications (3)
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Number |
Date |
Country |
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355016 |
May 1989 |
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335163 |
Apr 1989 |
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280603 |
Dec 1988 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
411449 |
Sep 1989 |
|
Parent |
326907 |
Mar 1989 |
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