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).
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Patent number: 4902795Abstract: 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: GrantFiled: November 17, 1988Date of Patent: February 20, 1990Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Crohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4880795Abstract: 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: GrantFiled: March 3, 1987Date of Patent: November 14, 1989Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4863916Abstract: 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: GrantFiled: May 6, 1987Date of Patent: September 5, 1989Assignee: Bayer AktiengesellschaftInventors: Dieter Habich, Wolfgang Hartwig, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4855283Abstract: 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: GrantFiled: June 16, 1986Date of Patent: August 8, 1989Assignee: Bayer AktiengesellschaftInventors: 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
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Patent number: 4847375Abstract: 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: GrantFiled: June 13, 1986Date of Patent: July 11, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4840954Abstract: 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: GrantFiled: December 31, 1985Date of Patent: June 20, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4841059Abstract: 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: GrantFiled: October 15, 1987Date of Patent: June 20, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4840946Abstract: 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: GrantFiled: November 12, 1987Date of Patent: June 20, 1989Assignee: Bayer AktiengesellschaftInventors: Dieter Habich, Wolfgang Hartwig, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4820716Abstract: 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: GrantFiled: February 12, 1987Date of Patent: April 11, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4816451Abstract: 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: GrantFiled: June 29, 1987Date of Patent: March 28, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe, Hermann Hagemann, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4808724Abstract: 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: GrantFiled: September 30, 1987Date of Patent: February 28, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4806539Abstract: 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: GrantFiled: November 17, 1986Date of Patent: February 21, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4767754Abstract: 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: GrantFiled: October 30, 1986Date of Patent: August 30, 1988Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4762844Abstract: 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: GrantFiled: November 5, 1985Date of Patent: August 9, 1988Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4757065Abstract: 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: GrantFiled: November 20, 1984Date of Patent: July 12, 1988Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: 4753925Abstract: 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: GrantFiled: August 22, 1986Date of Patent: June 28, 1988Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4748163Abstract: 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: GrantFiled: February 21, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4737488Abstract: 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: GrantFiled: November 29, 1984Date of Patent: April 12, 1988Assignee: Bayer AktiengesellschaftInventors: Oswald Lockhoff, Bernd-Wieland Kruger, Peter Stadler, Karl G. Metzger, Hans-Georg Opitz, Klaus Schaller, Klaus G. Stunkel, Hans-Joachim Zeiler
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Patent number: 4735938Abstract: 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: GrantFiled: July 10, 1986Date of Patent: April 5, 1988Assignee: Bayer AktiengesellschaftInventors: Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
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Patent number: RE32975Abstract: 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: GrantFiled: May 14, 1985Date of Patent: July 4, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger