Patents by Inventor Karl G. Metzger

Karl G. Metzger has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4902795
    Abstract: 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## or ##STR3## m and n are 0 or 1, and A, B, D and E are CH or substituted C or up to three of them are N,and physiologically acceptable salts thereof. Novel intermediates are described as well as processes for making the intermediates and end products.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: February 20, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Crohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4880795
    Abstract: 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 aliphatic or cycloaliphatic hydrocarbyl radical of up to 6 carbon atoms, but is not unsubstituted methyl,or pharmaceutically acceptable salts thereof, are effective antibacterially and promote the growth of animals.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: November 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4863916
    Abstract: 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## R.sup.3 is a COOH radical, or salt or ester thereof.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: September 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Wolfgang Hartwig, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4855283
    Abstract: 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 radical having up to 50 carbon atoms,R.sup.3, R.sup.4 and R.sup.5, independently of one another, denotes hydrogen or acyl--CO--R.sup.6, R.sup.6 being an alkyl radical having up to 10 carbon atoms,R.sup.7 denotes hydrogen, C.sub.1 -C.sub.7 -alkyl-, hydroxymethyl, 1-hydroxyethyl, mercaptomethyl, 2-(methylthio)-ethyl, 3-aminopropyl, 3-ureidopropyl, 3-guanidyl-propyl, 4-aminobutyl, carboxymethyl, carbamylmethyl, 2-carboxyethyl, 2-carbamoylethyl, benzyl, 4-hydroxybenzyl, 3-indolylmethyl or 4-imidazolylmethyl, andR.sup.8 represents hydrogen or methyl, andR.sup.9 represents hydrogen, acetyl, benzoyl, trichloroacetyl, trifluoroacetyl, methoxycarbonyl, t-butyloxycarbonyl or benzyloxycarbonyl andR.sup.7 and R.sup.8 together can denote --CH.
    Type: Grant
    Filed: June 16, 1986
    Date of Patent: August 8, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Oswald Lockhoff, Yutaka Hayauchi, Peter Stadler, Klaus G. Stunkel, Gert Streissle, Arnold Paessens, Volker Klimetzek, Hans-Joachim Zeiler, Karl G. Metzger, Hein-Peter Kroll, Helmut Brunner, Klaus Schaller
  • Patent number: 4847375
    Abstract: 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 others can have various meanings,and pharmaceutically acceptable hydrate, alkali metal, alkaline earth metal, silver or guanidinium salt or ester thereof.
    Type: Grant
    Filed: June 13, 1986
    Date of Patent: July 11, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4840954
    Abstract: 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 well as their usefulness as antibacterial agents.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4841059
    Abstract: 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## m and n are 0 or 1, andA, B, D, and E are CH or substituted C or up to three of them are N,and physiologically acceptable salts thereof. Novel intermediates are described as well as processes for making the intermediates and end products.
    Type: Grant
    Filed: October 15, 1987
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4840946
    Abstract: Antibiotically active benzazolylthio-carbapenems of the formula ##STR1## in which R.sup.1 represents hydrogen or a hydroxyl-protecting group,R.sup.2 represents hydrogen or a carboxyl-protecting group or an ester radical which can be cleaved off in vivo,R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.12 -aryl or C.sub.7 -C.sub.14 -aralkyl,R.sup.4 represents hydrogen or represents C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.12 -aryl or C.sub.7 -C.sub.14 aralkyl, or represents C.sub.1 -C.sub.10 -alkylsulphonyl, C.sub.6 -C.sub.12 -arylsulphonyl or C.sub.7 -C.sub.14 -aralkylsulphonyl, or represents an amino-protecting group, or represents a group of the formula ##STR2## in which R.sup.5, R.sup.6 and R.sup.8 are indentical or different and denote hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.12 -aryl or C.sub.7 -C.sub.14 -aralkyl,andX represents O, S, NH or NCH.sub.3,or salts thereof.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: June 20, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Habich, Wolfgang Hartwig, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4820716
    Abstract: 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, hydroxymethyl 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.sup.1 is hydroxy, A is not CF or N, or pharmaceutically acceptable hydrates, or salts thereof, are useful as antibacterials and animal feed utilization promoters.
    Type: Grant
    Filed: February 12, 1987
    Date of Patent: April 11, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4816451
    Abstract: Antibacterially effective 1,8-bridged 4-quinolone-3-carboxylic acids and derivatives of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.7 or an acid amide group --CONR.sup.8 R.sup.9,X.sup.1 represents hydrogen, nitro, alkyl with 1-3 carbon atoms, or halogen,X.sup.5 represents hydrogen, halogen or alkyl,R.sup.10 and R.sup.11 complete an optionally substituted ring, andn is 0 or 1,and pharmaceutically usable hydrates, salts and esters thereof.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: March 28, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Hermann Hagemann, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4808724
    Abstract: Antibiotically active penicillins and cephalosporins of the formula ##STR1## in which Z is hydrogen or lower alkoxy,n is 1 or 2,Y, in the form of the free acid, is ##STR2## X is --S--, --n--, --SO-- or --SO.sub.2 --, T is an organic radical, hydrogen or halogen,A is hydroxyl, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, an optionally substituted polycyclic aromatic ring, an optionally substituted 5-membered or 6-membered heterocyclic ring with nitrogen, oxygen and/or sulphur as hetero atoms in the ring, or an optionally substituted polycyclic heterocyclic ring,or non-toxic pharmaceutically tolerated salts thereof.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: February 28, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4806539
    Abstract: An antibacterial 1-cyclopropyl-6-fluoro-1,4- dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid of the formula ##STR1## in which R represents branched or straight-chain propyl or butyl which is optionally substituted by hydroxy or methoxy, unsubstituted tert.-butyl, 2-methylthioethyl, trifluoromethylthiomethyl, 2-trifluoromethylthioethyl, cycloalkyl with 3 to 6 carbon atoms, cycloalkenyl having 5 to 6 carbon atoms optionally substituted by hydroxyl, 1,1-dioxidotetrahydrothiophen-3-yl, cyclopropylmethyl, 1-phenethyl, furylmethyl, allyl or propargyl optionally substituted by phenyl and their pharmaceutically usable hydrates, acid addition salts, metal and guanidinium salts and prodrug forms.
    Type: Grant
    Filed: November 17, 1986
    Date of Patent: February 21, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4767754
    Abstract: Antibacterially effective cephalosporins of the formula ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.6 -alkyl, phenyl or halogen-substituted phenyl andA represents a nitrogen-containing, positively charged heterocyclic 5-membered to 7-membered ring which is bonded via N and can contain a total of up to 4 hetero-atoms from the group comprising N, O and S, and onto which up to two further rings can be fused, and which can optionally be substituted, with the proviso that, if the ring is a 6-membered ring, A does not represent an unsubstituted pyridine ring or a pyridine ring which is mono- or di-substituted by identical or different substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, chlorine, bromine, carbamoyl or N-C.sub.1 -C.sub.4 -alkylcarbamoyl, or pharmaceutically acceptable salts thereof or esters thereof which can be split under physiological conditions.
    Type: Grant
    Filed: October 30, 1986
    Date of Patent: August 30, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4762844
    Abstract: Alkyl-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula ##STR1## in which X.sup.1, X.sup.2 and X.sup.3 each independently is hydrogen, a nitro group, a halogen atom or an alkyl radical with 1 to 3 carbon atoms, with the proviso that at least one of them is an alkyl radical,or pharmaceutically acceptable salts or hydrates thereof, are antibacterially active and promote animal growth.
    Type: Grant
    Filed: November 5, 1985
    Date of Patent: August 9, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4757065
    Abstract: Antibacterially effective cephalosporins of the formula ##STR1## in which R.sup.1 denotes C.sub.1 -C.sub.6 -alkyl, phenyl or halogen-substituted phenyl andA represents a nitrogen-containing, positively charged heterocyclic 5-membered to 7-membered ring which is bonded via N and can contain a total of up to 4 hetero-atoms from the group comprising N, O and S, and onto which up to two further rings can be fused, and which can optionally be substituted, with the proviso that, if the ring is a 6-membered ring, A does not represent an unsubstituted pyridine ring or a pyridine ring which is mono- or di-substituted by identical or different substituents from the group comprising C.sub.1 -C.sub.4 -alkyl, chlorine, bromine, carbamoyl or N--C.sub.1 -C.sub.4 -alkylcarbamoyl,or pharmaceutically acceptable salts thereof or esters thereof which can be split under physiological conditions.
    Type: Grant
    Filed: November 20, 1984
    Date of Patent: July 12, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4753925
    Abstract: Antibacterially effective 1,7-diamino-1,4-dihydro-4-oxo-3-(aza)quinolinecarboxylic acids of the formula ##STR1## in which A is nitrogen or C--R.sup.1,R.sup.1 is nitro or halogen,R.sup.2 and R.sup.3 each independently is C.sub.1 -C.sub.3 -alkyl, or together with the nitrogen atom to which they are bonded, form a 5-membered or 6-membered heterocyclic ring, which can additionally contain the atoms or groups --O--, --S--, --SO--, --SO.sub.2 -- or .dbd.N--R.sup.4 as a ring member and can optionally be mono-, di- or tri-substituted on the carbon atoms by C.sub.1 -C.sub.3 -alkyl, hydroxyl, alkoxy with 1-3 carbon atoms, amino, methylamino or ethylamino, it being possible for a carbon atom in each case to carry only one substituent,R.sup.
    Type: Grant
    Filed: August 22, 1986
    Date of Patent: June 28, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4748163
    Abstract: 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 >C.dbd.O or >C.dbd.N--R.sup.7,Z representing O, S, or NR.sup.10, andR.sup.2 represents hydrogen or a protective group.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: May 31, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4737488
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, an optionally substituted aromatic hydrocarbon radical, an aralkyl radical or an optionally substituted aliphatic hydrocarbon radical having up to 45 C atoms,R.sup.2 is an optionally substituted aromatic hydrocarbon radical, an aralkyl radical or an optionally substituted aliphatic hydrocarbon radical having 5-50 C atoms,X is O, S, NH or NR, R being an alkyl radical having up to 20 C atoms, andZ is a glycosyl radical bonded via the anomeric carbon atom,or pharmaceutically acceptable salts thereof stimulate the immune system.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: April 12, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Oswald Lockhoff, Bernd-Wieland Kruger, Peter Stadler, Karl G. Metzger, Hans-Georg Opitz, Klaus Schaller, Klaus G. Stunkel, Hans-Joachim Zeiler
  • Patent number: 4735938
    Abstract: Antibiotically active penicillins and cephalosporins of the formula ##STR1## in which Z is hydrogen or lower alkoxy,n is 1 or 2,Y, in the form of the free acid, is ##STR2## X is --S--, --n--, --SO-- or --SO.sub.2 --, T is an organic radical, hydrogen or halogen,A is hydroxyl, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, an optionally substituted polycyclic aromatic ring, an optionally substituted 5-membered or 6-membered heterocyclic ring with nitrogen, oxygen and/or sulphur as hetero atoms in the ring, or an optionally substituted polycyclic heterocyclic ring,or non-toxic pharmaceutically tolerated salts thereof.
    Type: Grant
    Filed: July 10, 1986
    Date of Patent: April 5, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: RE32975
    Abstract: 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 antibacterial and/or antifungal agents or for animal growth promotion or improved feed utilization.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: July 4, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger