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Details for Patent: 5,416,096

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Details for Patent: 5,416,096

Title: 7-(1-pyrrolidinyl)-3-quinolone carboxylic acid derivatives as antibacterial agents and feed additives
Abstract:7-(1-Pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives as antibacterial agents and feed additives, of the formula ##STR1## in which X.sup.1 is halogen, X.sup.2 is hydrogen, halogen, amino or other radical, R.sup.1 is alkyl, cycloalkyl, optionally substituted phenyl or other radical, R.sup.2 is hydrogen, alkyl or a dioxolylmethyl radical, R.sup.3 is ##STR2## and A is N, CH, C-halogen, or the like, or forms a bridge with R.sup.1, and addition products thereof.
Inventor(s): Petersen; Uwe (Leverkusen, DE), Schenke; Thomas (Bergisch-Gladbach, DE), Krebs; Andreas (Odenthal-Holz, DE), Grohe; Klaus (Odenthal, DE), Schriewer; Michael (Odenthal, DE), Haller; Ingo (Wuppertal, DE), Metzger; Karl G. (Wuppertal, DE), Endermann; Rainer (Wuppertal, DE), Zeiler; Hans-Joachim (Velbert, DE)
Assignee: Bayer Aktiengesellschaft (Leverkusen, DE)
Filing Date:Jul 30, 1991
Application Number:07/737,631
Claims:1. A 7-(pyrrolidinyl)-3-quinolone carboxylic acid derivative of the formula ##STR382## in which X.sup.1 represents fluorine,

R.sup.1 represents cyclopropyl,

R.sup.2 represents hydrogen or alkyl having 1 to 2 carbon atoms,

R.sup.4 represents methyl,

R.sup.5 represents H or methyl,

R.sup.6 represents H or methyl,

Z represents O or S, and

R.sup.8 represents H or halogen, or, together with R.sup.1, forms a bridge having the structure ##STR383## or a pharmaceutically acceptable addition product thereof with water, an acid or an alkali.

2. A compound or addition product thereof according to claim 1, in which

X.sup.1 represents fluorine,

R.sup.2 represents cyclopropyl,

R.sup.2 represents hydrogen,

R.sup.4 represents methyl,

R.sup.5 represents H or methyl,

R.sup.6 represents H,

Z represents O or S, and

R.sup.8 represents H, fluorine or chlorine.

3. A compound according to claim 1, wherein such compound is 7-(3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-4-oxo-3-qu inolinecarboxylic acid of the formula ##STR384## or an addition product thereof with water, an acid or an alkali.

4. A compound according to claim 1, wherein such compound is 7-(3-amino-4-methylthio-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dih ydro-4-oxo-3-quinolinecarboxylic acid of the formula ##STR385## or an addition product thereof with water, an acid of an alkali.

5. An antibacterial composition comprising an antibacterially effective amount of a compound or addition product thereof according to claim 1 and a diluent.

6. A composition according to claim 5 in the form of a tablet, capsule or ampule.

7. A composition according to claim 5, wherein the diluent comprises an animal feed stock.

8. A method of combating bacteria in a patient in need thereof which comprises administering to such patient an antibacterially effective amount of a compound or addition product thereof according to claim 1.

9. The method according to claim 8, wherein such compound is

7-(3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-4-oxo-3-qui nolinecarboxylic acid,

7-(3-amino-4-methylthio-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihy dro-4-oxo-3-quinolinecarboxylic acid,

or an addition product thereof with water, an acid or an alkali.

10. A method of promoting the growth of an animal which comprises administering to said animal a growth promoting effective amount of a compound or addition product thereof according to claim 1.

11. The method according to claim 10, wherein such compound is

7-(3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-4-oxo-3-qui nolinecarboxylic acid,

7-(3-amino 4-methylthio-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo- 3-quinolinecarboxylic acid,

or an addition product thereof with water, an acid or an alkali.
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