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: 4734407
    Abstract: Antibacterially active and animal growth-regulating novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical of the formula ##STR2## Z represents oxygen, sulphur or --N--R.sup.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: March 29, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4725595
    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, --CON< or --SO.sub.2 N<,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: January 8, 1987
    Date of Patent: February 16, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4716152
    Abstract: Compounds of the formula ##STR1## in which X is hydrogen or the radical CH.sub.2 OR.sup.5,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently is hydrogen or the radical ##STR2## Y is oxygen, sulphur, NH or CH.sub.2, and R.sup.1 and R.sup.6 each independently is an optionally substituted hydrocarbon radical having up to 50 carbon atoms, with the proviso that at least one of the radicals R.sup.1 and/or R.sup.6 contains between 9 to 50 carbon atoms,some of which are known, stimulate the immune system's response and antibody production.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: December 29, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Oswald Lockhoff, Karl G. Metzger, Hans-Georg Opitz, Klaus Schaller, Klaus G. Stunkel, Hans-Joachim Zeiler
  • Patent number: 4705788
    Abstract: Novel antibacterially active 7-amino-1-(substituted cyclopropyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula ##STR1## in which X.sup.1 and X.sup.2 can be identical or different and represent hydrogen or halogen,R.sub.1, R.sub.2 and R.sub.3 represent hydrogen, methyl, chlorine or fluorine, the radicals R.sub.1 -R.sub.3 never all being identical, andR.sup.4 and R.sup.5, together with the nitrogen atom to which they are bonded, form a 5-membered or 6-membered heterocyclic ring which may be substituted.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: November 10, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4703047
    Abstract: Novel antibacterially active 1-cyclopropyl-1,4-dihydro-4-oxo-7-[4-(2-oxo-1,3-dioxol-4-yl-methyl)-1-pipe razinyl]-3-quinolinecarboxyic acids of the formula in which ##STR1## R is hydrogen or, together with R.sup.1, forms an alkylene radical with 2 or 3 carbon atoms,R.sup.1 is hydrogen, alkyl with 1 to 4 carbon atom or phenyl,R.sup.2 and R.sup.3 each independently is hydrogen, methyl, ethyl, cyclohexyl, methylene-dioxphenyl, furyl, tetrahydrofuryl or thienyl; or phenyl which is optionally mono-, di or tri-substituted by fluorine, chlorine, bromine, methyl, phenyl, cyano, hydroxyl, ethoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro,X.sup.1 is hydrogen, halogen, or nitro, andX.sup.2 is hydrogen or halogen,or pharmaceutically acceptable hydrates, acid addition salts, alkali metal salts or alkaline earth metal salts thereof.
    Type: Grant
    Filed: January 27, 1986
    Date of Patent: October 27, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4699899
    Abstract: Novel compounds of the formula ##STR1## in which X is hydrogen or --CH.sub.2 --OR.sup.5,Z represents OR.sup.4, NH.sub.2 or ##STR2## R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently is hydrogen or ##STR3## at least one of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being ##STR4## Y and W each independently is oxygen, sulphur, NH or CH.sub.2, and R.sup.1, R.sup.6, R.sup.7 and R.sup.8 each independently is an optionally substituted hydrocarbon radical with up to 50 C atoms,stimulate the immune system.
    Type: Grant
    Filed: February 21, 1986
    Date of Patent: October 13, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Yutaka Hayauchi, Oswald Lockhoff, Peter Stadler, Karl G. Metzger, Klaus G. Stunkel, Hans-Joachim Zeiler
  • Patent number: 4686216
    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: May 6, 1985
    Date of Patent: August 11, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4670542
    Abstract: New antibiotics of the formula ##STR1## in which X is O or N--CO--NH.sub.2,R is the radical of an aminoacid other than serine, an oligopeptide other than HyoHyoHyoSer or a derivative thereof on the free amino group, or a radical from the group comprising HyoSer, HyoHyoSer, HyoHyoHyoAla, HyoHyoHyoThr, Hyo, HyoHyo or HyoHyoHyo, andHyo is N.sup.5 -acetyl-N.sup.5 -hydroxy-L-ornithine.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: June 2, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Benz, Karl G. Metzger, Jorg Pfitzner, Delf Schmidt, Hans-Joachim Zeiler
  • Patent number: 4670444
    Abstract: 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 invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: June 2, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4666920
    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,R.sup.
    Type: Grant
    Filed: March 15, 1985
    Date of Patent: May 19, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4659603
    Abstract: 1-Cyclopropylquinolone-3-carboxylic acids of the formula ##STR1## in which R.sup.1 is hydrogen, methyl, ethyl or .beta.-hydroxyethyl, andR.sup.2 is hydrogen, chlorine or fluorineor salts thereof stimulate the immune system, especially in conjunction with an antigen.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Volker Klimetzek, Karl G. Metzger, Klaus G. Stunkel, Hans-Joachim Zeiler
  • Patent number: 4632918
    Abstract: Novel .beta.-lactam antibiotics of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, denote a substituted or unsubstituted alkyl radical or a monocyclic or bicyclic, optionally substituted, carbocyclic or heterocyclic ring, orR.sup.1 represents an optionally substituted alkyl radical or a monocyclic or bicyclic, substituted or unsubstituted, carbocyclic or heterocyclic ring, andR.sup.2 and R.sup.3, together with the N.sup..sym. atom, form an optionally substituted monocyclic or polycyclic ring which can be saturated or unsaturated and can contain oxygen, sulphur and nitrogen as other hetero atoms, orR.sup.1, R.sup.2 and R.sup.3, together with the N.sup..sym. atom, form a bridged, optionally substituted polycyclic ring which can be saturated or unsaturated and can contain oxygen, sulphur and nitrogen as other hetero atoms, andR.sup.
    Type: Grant
    Filed: May 6, 1985
    Date of Patent: December 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4631275
    Abstract: 1-Oxadethiacephalosporin derivatives of the formula ##STR1## in which R.sup.1 denotes hydrogen or halogen,R.sup.2 denotes hydrogen or methoxy,A is a nitrogen-containing positively charged N-containing heterocyclic 5-membered to 7-membered ring which in total can contain up to 4 heteroatoms from the group of N, O and S, to which ring up to two further rings can be fused and which ring may optionally be substituted, the ring being bonded via N,B denotes optionally substituted alkoxy or amino, and the remaining radicals are more or less conventional,which are antibacterially active.
    Type: Grant
    Filed: January 30, 1985
    Date of Patent: December 23, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Hartwig, Dieter Habich, Karl G. Metzger, Hans-Joachim Zeiler
  • Patent number: 4631272
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 represents hydrogen or an optionally substituted, straight-chain or branched alkyl or mono- or poly-unsaturated alkenyl radical with in each case up to 30 C atoms,X represents CH.sub.2, O, S or NR,whereinR denotes hydrogen or an alkyl group with up to 20 C atoms, andR.sup.2 represents hydrogen or an optionally substituted, straight-chain or branched, saturated or mono- or poly-unsaturated hydrocarbon radical with up to 30 C atoms,or pharmaceutically acceptable salts thereof, stimulate the immune system and help fight infection.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: December 23, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Oswald Lockhoff, Bernd-Wieland Kruger, Peter Stadler, Karl G. Metzger, Hein-Peter Kroll, Klaus Schaller, Hans-Joachim Zeiler
  • Patent number: 4626525
    Abstract: New antibiotics of the formula ##STR1## in which X is O or N--CO--NH.sub.2,R is the radical of an aminoacid other than serine, an oligopeptide other than HyoHyoHyoSer or a derivative thereof on the free amino group, or a radical from the group comprising HyoSer, HyoHyoSer, HyoHyoHyoAla, HyoHyoHyoThr, Hyo, HyoHyo or HyoHyoHyo, andHyo is N.sup.5 -acetyl-N.sup.5 -hydroxy-L-ornithine.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: December 2, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Benz, Karl G. Metzger, Jorg Pfitzner, Delf Schmidt, Hans-Joachim Zeiler
  • Patent number: 4626535
    Abstract: Novel antibacterially active cephalosporins of the formula ##STR1## in which R.sup.1 denotes hydrogen, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, a polycyclic aromatic ring or an optionally substituted heterocyclic 5- or 6-member ring having 1-4 heteroatoms,R.sup.2 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkenyl, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, hydroxymethyl, formyloxymethyl, C.sub.1 -C.sub.4 -alkylcarbonyloxymethyl, aminocarbonyloxymethyl, pyridiniummethyl, 4-carbamoylpyridiniummethyl, 4-sulphonylethylpyridiniummethyl, 4-carboxylmethylpyridiniummethyl or heterocyclylthiomethyl, heterocyclyl representing a radical of the formula ##STR2## wherein R.sup.8 denotes hydrogen, methyl, 2-dimethylaminoethyl, carboxymethyl, sulphomethyl, carboxyethyl or sulphoethyl andR.sup.9 denotes hydrogen or methyl,or pharmaceutically tolerated salts or esters thereof.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: December 2, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Angerbauer, Michael Boberg, Gunther Kinast, Karl G. Metzger, Wilfried Schrock, Hans-Joachim Zeiler
  • Patent number: 4620007
    Abstract: 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 specifications. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.
    Type: Grant
    Filed: December 11, 1985
    Date of Patent: October 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4599334
    Abstract: Novel 1-cyclopropyl-4-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarb oxylic acid antibacterials of the formula ##STR1## in which R.sup.1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, amino, dimethylamino, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms,R.sup.2 is phenyl or cyclohexyl optionally substituted up to three times by halogen, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro, or is methylenedioxyphenyl, methylenedioxycyclohexyl, furyl, tetrahydrofuryl or thienyl, andX.sup.1 is hydrogen or fluorine,or pharmaceutically ultizable hydrates, acid addition salts, alkali metal salts or alkaline earth metal salts thereof.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: July 8, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4588726
    Abstract: Novel antibacterially active 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinoli necarboxylic acids of the formula ##STR1## in which R.sup.1 is hydrogen, methyl or ethyl, andR.sup.2 is hydrogen or fluorine,and pharmaceutically tolerable hydrates and salts thereof.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: May 13, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4574122
    Abstract: Compounds of the formula ##STR1## in which X is hydrogen or the radical --CH.sub.2 OR.sup.5,three of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently is hydrogen or ##STR2## and the fourth is ##STR3## Z each independently is oxygen, sulphur, NH or CH.sub.2, and R.sup.1, R.sup.6 and R.sup.7 each independently is an optionally substituted hydrocarbon radical having up to 50 carbon atoms,stimulate the immune system's response and antibody production.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: March 4, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Oswald Lockhoff, Peter Stadler, Karl G. Metzger, Hans-Georg Opitz, Klaus G. Stunkel, Hans-Joachim Zeiler