Details for Patent: 4,990,517
✉ Email this page to a colleague
| Title: | 7-(1-pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic 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## 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: | Jun 30, 1989 |
| Application Number: | 07/375,434 |
| Claims: | 1. A 7-(pyrrolidinyl)-3-quinolone- or -naphthyridonecarboxylic 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.6 represents H, optionally hydroxyl-substituted C.sub.1 -C.sub.4 -alkyl, as well as phenyl, benzyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -acyl, (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, or C.sub.3 -C.sub.8 -cycloalkyl, R' represents H, CH.sub.3 or phenyl, R" represents H, CH.sub.3 or phenyl, R"' reprseents H or CH.sub.3, Y represents O, CH.sub.2 CH.sub.2 CH.sub.2 or CH.sub.2 --O, it being possible for the CH.sub.2 --O group to be linked to the nitrogen either via O or via CH.sub.2, 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 an addition product thereof with water, an acid or an alkali. 2. A compound or addition product thereof according 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, 2fluoroethyl, 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.6 represents H, optionally hydroxyl-substituted C.sub.1 -C.sub.3 -alkyl, as well as phenyl, benzyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.2 -acyl, (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, or C.sub.3 -C.sub.5 -cycloalkyl, R' represents H or CH.sub.3, R" represents H or CH.sub.3, R'" represents H or CH.sub.3, Y represents O, CH.sub.2 CH.sub.2 CH.sub.2 or CH.sub.2 --O, it being possible for the CH.sub.2 --O group to be linked to the nitrogen either via O or via CH.sub.2, 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.6 represents H, CH.sub.3, C.sub.2 H.sub.5, HOCH.sub.2 CH.sub.2, benzyl, C.sub.1-C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.2 -acyl, R' represents H or CH.sub.3, R" represents H or CH.sub.3, R'" represents H or CH.sub.3, Y represents O, CH.sub.2 CH.sub.2 CH.sub.2 or CH.sub.2 --O, it being possible for the CH.sub.2 --O group to be linked to the nitrogen either via O or via CH.sub.2, and Z represents O or S, and A represents N or C--Rhu 8, wherein R: represents H, fluorine or chlorine, or together with R.sup.1 also can form a bridge having the structure ##STR388## 4. A compound according to claim 1, wherein such compound is 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4-dihydro -4-oxo-3-quinolinecarboxylic acid of the formula ##STR389## or an addition product thereof with water, an acid or an alkali. 5. A compound according to claim 1, wherein such compound is 8-chloro-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-di hydro-4-oxo-3-quinolinecarboxylic acid of the formula ##STR390## or an addition product thereof with water, an acid or an alkali. 6. A compound according to claim 1, wherein such compound is 5-amino-1-cyclopropyl-7-(2,8diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4- dihydro-4-oxo-3-quinolinecarboxylic acid of the formula ##STR391## or an addition product thereof with water, an acid or an alkali. 7. A compound according to claim 1, wherein such compound is 1-cyclopropyl-7-(2,7-diazabicyclo [3.3.0]oct-7-yl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula ##STR392## or an addition product thereof with water, an acid or an alkali. 8. An antibacterial composition comprising an antibacterially effective amount of a compound or addition product thereof according to claim 1 and a diluent. 9. A composition according to claim 8 in the form of a tablet, capsule or ampule. 10. A composition according to claim 8, wherein the diluent comprises an animal feed stock. 11. 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. 12. 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. 13. The method according to claim 15, wherein such compound is 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4-dihydro- 4-oxo-3-quinolinecarboxylic acid, 8-chloro-1-cyclopropyl-3-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dih ydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4- dihydro-4-oxo-3-quinolinecarboxylic acid, or 1-cyclopropyl-7-(2,7-diazabicyclo[3.3.0]oct-7-yl)-6,8-difluoro-1,4-dihydro- 4-oxo-3-quinolinecarboxylic acid or an addition product thereof with water, an acid or an alkali. 14. The method according to claim 12, wherein such compound is 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4-dihydro- 4-oxo-3-quinolinecarboxylic acid, 8-chloro-1-cyclopropyl-3-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dih ydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4- dihydro-4-oxo-3-quinolinecarboxylic acid or 1-cyclopropyl-7-(2,7-diazabicyclo[3.3.0]oct-7-yl)-6,8-difluoro-1,4-dihydro- 4-oxo-3-quinolinecarboxylic acid or an addition product thereof with water, an acid or an alkali. |
