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Karl G. Metzger Patents |
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Inventor: Metzger; Karl G.
Address: Wuppertal, DE
No. of patents: 121
Patents:
| Patent Number |
Title Of Patent |
Date Issued |
| RE33948 |
.beta.-lactam antibiotics |
June 2, 1992 |
| Antibacterially active and animal growth-promoting novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents the radical ##STR2## Y representing N or CR.sup.9, or Y--R.sup.7 representing ##STR3## Z representing O, S, or NR.sup.10, and R.sup.2 repre |
| RE32975 |
4-Pyridone-3-carboxylic acids and/or derivatives thereof |
July 4, 1989 |
| The invention provides 4-pyridone-3-carboxylic acids and derivatives thereof together with a method for their preparation. Also included in the invention are compositions containing said 4-pyridone-3-carboxylic acids and derivatives and the use of said compounds and compositions as a |
| RE31512 |
Pseudotrissaccharides, a process for their production and their use as medicaments |
January 31, 1984 |
| Pseudotrisaccharides of the sisomycin type are provided which are effective an antibacterial agents, particularly against gram-negative microorganisms. The invention also includes methods for the manufacture of the pseudotrisaccharides, compositions containing said pseudotrisaccharid |
| 5631291 |
Cyclopentane- and -pentene-.beta.-amino acids |
May 20, 1997 |
| The invention relates to cyclopentane- and -pentene-.beta.-amino acids, processes for their preparation and their use as medicaments. |
| 5621105 |
Preparation of 7-(aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl) quinolonecarboxylic and 7-(amino |
April 15, 1997 |
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| 5607942 |
7-(1-pyrrolidinyl)-3-quinolone- and - naphthyridone-carboxylic acid derivatives as antibacterial |
March 4, 1997 |
| 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 |
| 5605910 |
Quinolone-and naphthyridonecarboxylic acid derivatives |
February 25, 1997 |
| The invention relates to new quinolone- and naphthyridonecarboxylic acid derivatives which are substituted in the 7-position by a tricyclic amine radical, their salts, processes for their preparation and antibacterial compositions comprising these compounds. |
| 5574161 |
7-(aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)quinolonecarboxylic and 7-(aminomethyl-oxa-7-aza |
November 12, 1996 |
| The invention relates to novel derivatives of quinolone-carboxylic acid and naphthyridonecarboxylic acid which are substituted in the 7 position by a 1- (or 5-)amino-methyl-2- (or 3-)oxa-7-aza-bicyclo[3.3.0]oct-7-yl residue, their salts, processes for their preparation and antibacterial |
| 5571812 |
7-amino-1-cyclopropyl-6,8-dihalogeno- 1,4-dihydro-4-oxo-3-quinolinecarboxylic acid antibacterial |
November 5, 1996 |
| The invention is related to 7-amino-1-cyclopropyl-6,8- dihalogeno-1,4-dihydro-4-oxo-3-quinoline-carboxylic acids of the formula (I) ##STR1## in which X.sup.1, X.sup.2, R.sup.1 and R.sup.2 have the meaning as pointed out in the following specification. Moreover, the invention is r |
| 5556979 |
7-isoindolinyl-naphthyridone derivatives, compositions and anti-bacterial use thereof |
September 17, 1996 |
| The invention relates to novel quinolone derivatives and naphthyridone derivatives which are substituted in the 7-position by a partially hydrogenated isoindolinyl ring, to processes for their preparation and to antibacterial agents and feed additives containing them. |
| 5545642 |
Derivatives of 1-(2-fluorocyclopropyl)-quinolonecarboxylic acid and 1-(2-fluorocyclopropyl)-naph |
August 13, 1996 |
| The invention relates to novel derivatives of 1-(2-fluorocyclopropyl)-quinolonecarboxylic acid and 1-(2-fluorocyclopropyl)-naphthyridonecarboxylic acid which are substituted in the 7 position by a 2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-c]pyridin-2-yl or 1,2,3,4,5,6-hexahydropyrrolo[3,4 |
| 5508278 |
Pyrido[1,2,3-D,E] [1,3,4]benzoxadiazine derivatives |
April 16, 1996 |
| Novel bactericidal pyrido[1,2,3-d,e,][1,3,4]benzoxadiazine derivatives of the formula (I) ##STR1## in which R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl optionally substituted by hydroxyl or halogen,R.sup.2 independently of R.sup.1 is hydrogen or methyl,R.sup.3 is hydrogen or C.sub |
| 5468861 |
8-chloro-1-cyclopropyl-6,7-difluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl ester |
November 21, 1995 |
| The invention is related to 7-amino-1-cyclopropyl-6,8-dihalogeno-1,4-dihydro-4-oxo-3-quinoline-carboxy lic acids of the formula (I) ##STR1## in which X.sup.1, X.sup.2, R.sup.1 and R.sup.2 have the meaning as pointed out in the following specification. Moreover, the invention is re |
| 5468742 |
8-vinyl- and 9-ethinyl-quinolone-carboxylic acids |
November 21, 1995 |
| The invention relates to new 8-vinyl- and 8-ethinylquinolonecarboxylic acids, process for their preparation, and antibacterial agents and feed additives containing them. |
| 5453422 |
Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibact |
September 26, 1995 |
| An antibacterially active quinolone or naphthyridonecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 stands for various organic radical,R.sup.2 stands for hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl,R.sup.3 stands for hydro |
| 5416096 |
7-(1-pyrrolidinyl)-3-quinolone carboxylic acid derivatives as antibacterial agents and feed addi |
May 16, 1995 |
| 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 o |
| 5395944 |
7-(aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)quinolonecarboxylic and 7-(aminomethyl-oxa-7-aza |
March 7, 1995 |
| 7-(Aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)quinolonecarboxylic acid and 7-(aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)naphthyridonecarboxyli c acid derivatives The invention relates to novel derivatives of quinolonecarboxylic acid and naphthyridonecarboxylic acid which are subs |
| 5284855 |
7-(2,7-diazabicyclo[3.3.0]octyl)-3-quinolone-and-naphthyridonecarboxylic acid derivatives |
February 8, 1994 |
| The invention relates to new 7-(2,7-Diazabicyclo[3.3.0]octyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives, processes for their preparation, and anti-bacterial agents and feed additives containing them. |
| 5284842 |
Quinolone- and naphthridone carboxylic acid derivatives, process for their production, antibacte |
February 8, 1994 |
| An antibacterially active quinolone or naphthyridonecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 stands for various organic radical,R.sup.2 stands for hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,R.sup.3 stands for hydrog |
| 5276024 |
3-substituted cephalosporins, and their use as medicaments |
January 4, 1994 |
| The invention relates to new 3-substituted cephalosporins, to a process for their preparation and to their use as medicaments, in particular as medicaments having antibacterial activity.The invention relates to compounds of the general formula (I) ##STR1## in which X, Y, R.sup.1 and |
| 5252734 |
Antibacterial 5-alkylquinolonecarboxylic acids |
October 12, 1993 |
| Antibacterial 5-alkylquinolonecarboxylic acids of the formula ##STR1## in which R.sup.3 is C.sub.1 -C.sub.4 - alkyl,R.sup.1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl,R.sup.2 is hydrogen or optionally substituted a |
| 5237060 |
Process of preparing enantiomerically pure 1,8-bridged 4-quinolone-3-carboxylic acids |
August 17, 1993 |
| The invention relates to a process for the preparation of highly antibacterially active enantiomerically pure 1,8-bridged 4-quinolone-3-carboxylic acids and derivatives of the formula (I) ##STR1## in which 1) a compound of the formula ##STR2## is reacted with a compound of t |
| 5202337 |
7-(2,7-diazabicyclo[3.3.0]octyl)-3-quinoline- and -naphthyridone-carboxylic acid derivatives |
April 13, 1993 |
| The invention relates to new 7-(2,7-Diazabicyclo[3.3.0]octyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives, processes for their preparation, and antibacterial agents and feed additives containing them. |
| 5190955 |
Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
March 2, 1993 |
| Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxlyic acid derivatives of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.1 or an acid amide group --CONR.sup.2 R.sup.3,X.sup.1 represents hydrogen nitro, alk |
| 5173484 |
Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibact |
December 22, 1992 |
| An antibacterially active quinolone or naphthyridonecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 stands for various organic radical,R.sup.2 stands for hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,R.sup.3 stands for hydrog |
| 5171854 |
Substituted vinylcephalosporins |
December 15, 1992 |
| .beta.-Lactam compounds of the formula ##STR1## wherein R.sup.5 represent cyclopropyl or methyl, useful as antibiotics. |
| 5153204 |
7-(1-Pyrrolidinyl)-quinolonecarboxylic acid derivatives |
October 6, 1992 |
| 7-(1-Pyrrolidinyl)-3-quinolonecarboxylic acid derivatives of the formula ##STR1## in which A is CH, CCl, CF or N,R.sup.1 is hydroxyl, hydroymethyl or mercapto andR.sup.2 is hydrogen, alkyl, having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,with the proviso that, when R |
| 5145853 |
Bactericidal formulations for use in veterinary medicine |
September 8, 1992 |
| A method of treating livestock infected with, or protecting livestock against infection from, bacteria which comprises administering to such livestock an antibacterially effective amount of a quinolonecarboxylic acid or derivative of the formula ##STR1## in which A represents nit |
| 5140033 |
Antibacterial 5-alkylquinolonecarboxylic acids |
August 18, 1992 |
| Antibacterial 5-alkylquinolonecarboxylic acids of the formula ##STR1## in which R.sup.3 is C.sub.1 -C.sub.4 -alkyl,R.sup.1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl,R.sup.2 is hydrogen or optionally substituted al |
| 5108747 |
Stable oxpenem-3-carboxylic acids as beta-lactamase inhibitors |
April 28, 1992 |
| A pharmaceutical preparation comprising an antibiotic, a pharmaceutical excipient therefor, and in addition an oxapenem-3-carboxylic acid of the formula ##STR1## or a pharmaceutically acceptable salt, ester or amide in which R.sup.1 and R.sup.2 each independently is hydrogen or a |
| 5077429 |
7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline- and naphthyridine-3-carboxylic acids, process |
December 31, 1991 |
| 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 inventio |
| 5061712 |
Preparation of 7-(3-amino- and 3-amino-methyl-1-pyrrolidinyl)-3-quinolonecarboxylic acids and |
October 29, 1991 |
| Process for the preparation of antibacterial compounds of the formula ##STR1## comprises condensing an oxo compound of the formula ##STR2## with an amino compound of the formula ##STR3## to produce a compound of the formula ##STR4## reacting the compound of the formul |
| 5059597 |
7-(4-oxa or 4-thia-2,7-diazabicyclo[3.3.0]oct-2-en-3-yl)-3-quinolone-and-naphthyrido ne-carbo |
October 22, 1991 |
| 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 |
| 5051418 |
Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
September 24, 1991 |
| Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivatives of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.1 or an acid amide group --CONR.sup.2 R.sup.3,X.sup.1 represents hydrogen nitro, alk |
| 4990517 |
7-(1-pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives as antibacterial a |
February 5, 1991 |
| 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 o |
| 4988685 |
Cephalosporins derivatives |
January 29, 1991 |
| Novel cephalosporins of the formula ##STR1## in which R.sup.1 represents hydrogen or an amino-protecting groupandR.sup.2 represents alkyl, cycloalkyl or alkenyl. |
| 4981854 |
A-aryl-4-quinolone-3-carboxylic acids |
January 1, 1991 |
| Antibacterially active and animal growth promoting novel 1-aryl-4-quinolone-3-carboxylic acids of the formula ##STR1## in which X is halogen or nitro,X.sup.2 is halogen,R is optionally substituted phenyl, andA is halogen or optionally substituted piperazine or pyrrolidine,or pharmaceutic |
| 4980353 |
1-aryl-4-quinolone-3-carboxylic acids |
December 25, 1990 |
| Antibacterially active and animal growth promoting novel 1-aryl-4-quinolone-3-carboxylic acids of the formula ##STR1## in which X is halogen or nitro,X.sup.2 is halogen,R is optionally substituted phenyl, andA is halogen or optionally substituted piperazine or pyrrolidine,or pharmaceutic |
| 4980348 |
Carbacephem antibiotics |
December 25, 1990 |
| A heteroanellated phenylglycine-.beta.-lactam antibiotic of the formula ##STR1## in which R.sup.1 - stands for a radical of the formula ##STR2## |
| 4973685 |
Heteroannellated phenylglycine-.beta.-lactam antibiotics |
November 27, 1990 |
| Heteroannellated penicillins and cephalosporins of the formula ##STR1## in which R.sup.1 --stands for a radical of the formula ##STR2## |
| 4952695 |
Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, intermediate for anti |
August 28, 1990 |
| 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and ester as pharmaceutical intermediate. |
| 4943568 |
Cephalosporins |
July 24, 1990 |
| Antibacterially active novel cephalosporins of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkoxy, alkylthio, halogen, trifluoromethyl or trifluoromethoxy,R.sup.2 represents hydrogen or an organic radical,R.sup.3 represents hydrogen, alkyl, alkenyl, alkoxy, alkylthio |
| 4908366 |
Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
March 13, 1990 |
| Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivatives of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.1 or an acid amide group --CONR.sup.2 R.sup.3,X.sup.1 represents hydrogen nitro, alk |
| 4902795 |
Intermediates for 1,8-bridged 4-quinolone-3-carboxylic acid antibacterials |
February 20, 1990 |
| Antibacterially active new 1,8-bridged 4-quinolone-3-carboxylic acid derivatives of the formula ##STR1## in which Y is carboxyl or a derivative thereofR.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2 and X.sup.5 are H or various radicals,Z is O, NH, substituted NH, ##STR2## |
| 4880795 |
Cephalosporins |
November 14, 1989 |
| Novel cephalosporins of the formula ##STR1## in which R.sup.1 is an aliphatic or cycloaliphatic hydrocarbyl radical of up to 6 carbon atoms which is optionally substituted by a carboxyl group, ##STR2## R.sup.2 and R.sup.3 each independently is an optionally substituted alipha |
| 4863916 |
Substituted 6-hydroxymethyl-carbapenem antibiotics |
September 5, 1989 |
| Substituted 6-hydroxymethyl-carbapenem antibiotics of the formula ##STR1## in which R.sup.1 is --OR.sup.4, ##STR2## A is a direct bond, or an alkylene and/or cycloalkylene radical, R.sup.2 is a group of the formula ##STR3## an aryl or heterocyclic radical, ##STR4## |
| 4855283 |
Novel pharmaceutically active N-(2-aminoacylamido-2-deoxy-hexosyl)-amides, -carbamates and -urea |
August 8, 1989 |
| Compounds of the formula ##STR1## in which R.sup.1 denotes hydrogen or a saturated or singly or multiply unsaturated alkyl radical having up to 50 carbon atoms,X represents --CH.sub.2 --, --O-- or --NH--,R.sup.2 denotes hydrogen or a saturated or singly or multiply unsaturated alkyl |
| 4847375 |
Antibacterial 1,8-bridged 4-quinoline-3-carboxylic acids |
July 11, 1989 |
| As antibacterials and animal growth promoters, the compounds of the formula ##STR1## in which Y is --COOH, --COOR.sup.7 or --CONR.sup.8, R.sup.9,X.sup.1 is H, nitro, alkyl or halogen,R.sup.10 and R.sup.11 preferably complete a piperazine ring,Z is oxygen or NR.sup.15,n is 0 or 1, andthe othe |
| 4841059 |
Pyridine-enamines |
June 20, 1989 |
| Antibacterially active new 1,8-bridged 4-quinolone-3-carboxylic acid derivatives of the formula ##STR1## in which Y is carboxyl or a derivative thereofR.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1, X.sup.2 and X.sup.5 are H or various radicals,Z is O, NH, substituted NH, ##STR2## |
| 4840954 |
6,7-disubstituted 1-cycloproply-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids |
June 20, 1989 |
| New 6,7-disubstituted-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carb oxy lic acids of the formula (I) ##STR1## in which X represents halogen or nitro and A represents ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined hereinbelow are disclosed as |
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