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Claims for Patent: 4,670,444

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Claims for Patent: 4,670,444

Title: 7-amino-1-cyclopropyl-4-oxo-1, 4-dihydro-quinoline-and naphthyridine-3-carboxylic acids and antibacterial agents containing these compounds
Abstract:The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1, 4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specification. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.
Inventor(s): Grohe; Klaus (Odenthal, DE), Zeiler; Hans-Joachim (Velbert, DE), Metzger; Karl G. (Wuppertal, DE)
Assignee: Bayer Aktiengesellschaft (Leverkusen, DE)
Application Number:06/614,923
Patent Claims: 1. A compound which is a 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline- and -napthyridine-3-carboxylic acid of the formula ##STR32## or a pharmaceutically acceptable acid addition salt or an alkali or alkaline earth metal salt thereof,

in which A represents a nitrogen atom or CR.sup.3,

wherein R.sup.3 denotes a hydrogen, a nitro group or a halogen atom, or a carboxamide or carboxyl group, and

Z represents a nitrogen atom or C--H, and A and Z cannot simultaneously be nitrogen atoms, and R.sup.1 and R.sup.2 are identical or different and represent a hydrogen atom or a straight-chain or branched alkyl, alkenyl or alkinyl radical which has up to 12 carbon atoms and is optionally substituted by radical(s) selected from hydroxyl, alkoxy, alkylmercapto or dialkylamino with 1 to 3 carbon atoms in each alkyl radical, alkoxycarbonyl with 1 to 4 carbon atoms in the alcohol part, and mono- or bi-cyclic carbocyclic aryl, or furthermore represents a cycloalkyl radical with 3 to 6 carbon atoms, or, together with the nitrogen atom which they substituted or together with a further hetero-atom selected from the group consisting of N, O and S form a 3-membered to 7-membered ring which can be substituted by radical(s) selected from alkyl or alkenyl with 1 to 6 carbon atoms, hydroxyl, alkoxy or alkylmercapto with 1 to 3 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alcohol part, and mono- or bi-cyclic carbocyclic aryl.

2. A compound according to claim 1, in which A represent CR.sup.3 and R.sup.3 represents a fluorine or chlorine atom.

3. A compound according to claim 1 or 2, in which R.sup.1 and R.sup.2 together with the nitrogen atom which they substituted and oxygen, sulphur or R.sup.4 -substituted nitrogen as a further hetero-atom form a 3-membered or 7-membered ring which may be substituted by radical(s) selected from alkyl or alkenyl with up to 6 carbon atoms, hydroxyl, alkoxy or alkylmercapto with 1 to 3 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alcohol part, and mono- or bi-cyclic carboxylic aryl,

and in which R.sup.4 represents a hydrogen, or an unsubstituted branched or straight-chain alkyl group which has up to 6 carbon atoms or a branched or straight-chain alkyl which has up to 6 carbon atoms which is substituted by radicals(s) selected from hydroxyl, alkoxy, alkylmercapto or dialkylamino with 1 to 3 carbon atoms per alkyl radical, and alkoxycarbonyl with 1 to 4 carbon atoms in the alcohol part, or represents an phenylalkyl group which has up to 4 carbon atoms in the aliphatic part, or an optionally substituted phenyl or naphthyl group or pyridine, pyrimidine, thiazole or benzothiazole, or

R.sup.4 denotes an alkoxycarbonyl group which is optionally substituted by a mono- or bi-cyclic carbocyclic aryl radical and has 1 to 4 carbon atoms in a alcohol part an alkanoyl radical with 1 to 6 carbon atoms, a benzoyl or naphthoyl radical, an alkyl-, phenyl- or naphthyl-(thio) carbamoyl radical, an alkyl-, phenyl- or naphthyl-sulphonyl radical or an aminosulphonyl radical.

4. A compound according to claim 3, in which R.sup.4 represents a radical of pyridine, pyrimidine, thiazole or benzothiazole.

5. A 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino-quinoline-3-carboxyl ic acid of the formula ##STR33## or salts and/or hydrates thereof, in which R denotes hydrogen, methyl, ethyl or .beta.-hydroxyethyl.

6. A compound according to claim 1 which is 7-(4-methylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-car boxylic acid.

7. A compound according to claim 1 which is 7-piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.

8. A compound according to claim 1 which is 7-pyrrolidino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.

9. A compound according to claim 1 which is 7-(4-formylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-car boxylic acid.

10. A compound according to claim 1 which is 7-(4-hydroxyethylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine -3-carboxylic acid.

11. A compound according to claim 1 which is 7-piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-6-fluoro-quinoline-3-carboxyl ic acid.

12. A compound of claim 5 which is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazino-quinoline-3-carboxyl ic acid.

13. A compound of claim 5 which is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylpiperazino)-quinoline- 3-carboxylic acid.

14. A compound of claim 5 which is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-ethylpiperazino)-quinoline-3 -carboxylic acid.

15. A compound of claim 5 which is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-.beta.-hydroxyethyl-peperazi no)-quinoline-3-carboxylic acid.

16. A pharmaceutical composition containing as an active ingredient an antibacterially effective amount of a compound according to claim 1 in admixture with an inert pharmaceutical carrier.

17. A pharmaceutical composition according to claim 16 in the form of a sterile or physiologically isotonic aqueous solution.

18. A composition according to claim 16 or 17 containing from 0.5 to 95% by weight of the said active ingredient.

19. A medicament in dosage unit form comprising an antibacterially effective amount of a compound according to claim 1 together with an inert pharmaceutical carrier.

20. A medicament of claim 18 in the form of tablets, pills, dragees, capsules, ampoules, or suppositories.

21. A method of combating bacterial illnesses in warm-blood animals which comprises administering to the animals an antibacterially effective amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

22. An animal feed, food concentrate or drinking water comprising an active compound according to claim 1.
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