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Details for Patent: 5,059,597

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Details for Patent: 5,059,597

Title: 7-(4-oxa or 4-thia-2,7-diazabicyclo[3.3.0]oct-2-en-3-yl)-3-quinolone-and-naphthyrido ne-carboxylic acid derivatives as antibacterial agents and feed additives
Abstract:7-(1-Pyrrolidinyl)-3-quinolone- and -naphthyridone-carboxylic 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 (Bayerwerk, DE), Schenke; Thomas (Bayerwerk, DE), Krebs; Andreas (Bayerwerk, DE), Grohe; Klaus (Bayerwerk, DE), Schriewer; Michael (Bayerwerk, DE), Haller; Ingo (Wuppertal-Elberfeld, DE), Metzger; Karl G. (Wuppertal-Elberfeld, DE), Endermann; Rainer (Wuppertal-Elberfeld, DE), Zeiler; Hans-Joachim (Wuppertal-Elberfeld, DE)
Assignee: Bayer Aktiengesellschaft (Leverkusen, DE)
Filing Date:Sep 10, 1990
Application Number:07/580,906
Claims:1. A 7-(pyrrolidinly)-3-quinolone- or -naphthyridone- carboxylic acid derivative of the formula ##STR382## in which X.sup.1 represents halogen,

X.sup.2 represents hydrogen, amino, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 3 carbon atoms per alkyl group, hydroxyl, alkoxy having 1 to 4 carbon atoms, mercapto, alkylthio having 1 to 4 carbon atoms, arylthio or halogen,

R.sup.1 represents alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, 2-hydroxyethyl, 2-fluoroethyl, methoxy, amino, methylamino, ethylamino, dimethylamino or phenyl which is optionally substituted by 1 or 2 fluorine atoms,

R.sup.2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl,

R.sup.3 represents a radical of the structure ##STR383## wherein R.sup.7 represents H or C.sub.1 -C.sub.4 -alkyl,

R' represents H, CH.sub.3 or phenyl,

R" represents H, CH.sub.3 or phenyl, and

Z represents O or S, and

A represents N or C--R.sup.8, wherein

R.sup.8 represents H, halogen, methyl, cyano, nitro, hydroxyl or methoxy or, together with R.sup.1, forms a bridge having the structure ##STR384## or a pharmaceutically useable 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 or chlorine,

X.sup.2 represents hydrogen, amino, alkylamino having 1 or 2 carbon atoms, dimethylamino, hydroxyl, methoxy, mercapto, methylthio, phenylthio, fluorine or chlorine,

R.sup.1 represents alkyl having 1 to 3 carbon atoms, alkenyl having 2 or 3 carbon atoms, cycloalkyl having 3 to 5 carbon atoms, 2-hydroxyethyl, 2-fluoroethyl, methoxy, amino, methylamino, ethylamino, dimethylamino or phenyl which is optionally substituted by 1 or 2 fluorine atoms,

R.sup.2 represents hydrogen, alkyl having 1 to 3 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl,

R.sup.3 represents a radical having the structure ##STR385## wherein R.sup.7 represents H or C.sub.1 -C.sub.2 -alkyl,

R' represents H or CH.sub.3,

R" represents H or CH.sub.3, and

Z represents O or S, and

A represents N or C--R.sup.8, wherein

R.sup.8 represents H, fluorine, chlorine, bromine, methyl, nitro, hydroxyl or methoxy or together with R.sup.1 forms a bridge having the structure ##STR386##

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

X.sup.1 represents fluorine,

X.sup.2 represents hydrogen, amino, methylamino or fluorine,

R.sup.1 represents alkyl having 1 or 2 carbon atoms, vinyl, cyclopropyl, 2-hydroxyethyl, 2-fluoroethyl, methoxy, methylamino, 4-fluorophenyl or 2,4-difluorophenyl,

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

R.sup.3 represents a radical having the structure ##STR387## wherein R.sup.7 represents H or CH.sub.3,

R' represents H or CH.sub.3,

R" represents H or CH.sub.3, and

Z represents O or S, and

A represents N or C--R.sup.8, wherein

R.sup.8 represents H, fluorine or chlorine, or together with R.sup.1 also can form a bridge having the structure ##STR388##

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

5. A composition according to claim 4 in the form of a tablet, capsule or ampule.

6. A composition according to claim 4, wherein the diluent comprises an animal feed stock.

7. 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.

8. A method 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.
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