Patents by Inventor Klaus Grohe

Klaus Grohe 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: 5173484
    Abstract: 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 hydrogen or amino,R.sup.4 stands for a radical of the formula ##STR2## A stands for N or C-R.sup.5, whereinR.sup.5 stands for hydrogen, halogen methyl, cyano or nitro or else together with R.sup.1 can form a bridge of the structure ##STR3## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal salt, alkaline earth metal salt, silver salt or guanidinium salt of the carboxylic acid when R.sup.2 is hydrogen.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: December 22, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Schenke, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5153204
    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, 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.sup.1 is hydroxyl, 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: May 29, 1990
    Date of Patent: October 6, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 5145853
    Abstract: 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 nitrogen or .dbd.C--R.sup.4,R.sup.4 represents hydrogen, fluorine, chlorine, nitro or methyl,B represents ##STR2## and B also represents ##STR3## when R.sup.1 does not denote cyclopropyl, and R.sup.5 represents hydrogen, a branched or unbranched alkyl group which has 1 to 4 carbon atoms and which can optionally be substituted by a hydroxyl or methoxy group,R.sup.6 represents hydrogen, methyl or phenyl,R.sup.7 represents hydrogen or methyl,R.sup.8 represents amino, alkyl- or dialkylamino having 1 or 2 carbon atoms in the alkyl group, aminomethyl, alkyl- or dialkylaminomethyl having 1 or 2 carbon atoms in the alkyl group,R.sup.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl G. Metzger, Hans-Joachim Zeiler, Martin Scheer, Herbert Voege, Klaus Grohe
  • Patent number: 5140033
    Abstract: 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 alkyl,R.sup.4 is a nitrogen-containing heterocyclic radical, andA is hydrogen, halogen, methyl, cyano or nitro, or forms a bridge with R.sup.1.and hydrates and salts thereof.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: August 18, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Andreas Krebs, Uwe Petersen, Thomas Schenke, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5077429
    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: April 1, 1986
    Date of Patent: December 31, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 5072038
    Abstract: 2,3,4,5-trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 5061712
    Abstract: 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 formula (III) with a compound of the formula ##STR5## to give a compound of the formula ##STR6## and then eliminating the amino-protective group ##STR7##
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: October 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Andreas Krebs, Thomas Schenke, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5059597
    Abstract: 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 or other radical,R.sup.2 is hydrogen, alkyl or a dioxolylmethyl radical,R.sup.3 is ##STR2## and A is N, CH, C-halogen, or the like, or forms a bridge with R.sup.1,and addition products thereof.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Schenke, Andreas Krebs, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5051418
    Abstract: 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, alkyl or halogenX.sup.4 can be hydrogen or halogen, or alkyl,R.sup.4 and R.sup.5, together with the nitrogen atom to which they are bonded, form a 5- or 6-membered heterocyclic ring which can additionally contain the atoms or groups --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## as ring members or the group ##STR3## can also represent a ring system of the structure ##STR4## which can optionally be substituted on the ring carbons by methyl and pharmaceutically usable hydrates, salts or esters thereof.These compounds have a high antibacterial activity and are therefore suitable as active compounds for human and veterinary medicine.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: September 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Uwe Petersen, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 4990517
    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.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Schenke, Andreas Krebs, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 4990646
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 4990661
    Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.
    Type: Grant
    Filed: March 29, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
  • Patent number: 4981854
    Abstract: 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 pharmaceutically useable hydrates, acid additions salts, alkali metal, alkaline earth metal, silver or guanidinium salts thereof, and/or esters thereof.
    Type: Grant
    Filed: November 6, 1989
    Date of Patent: January 1, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4980353
    Abstract: 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 pharmaceutically useable hydrates, acid additions salts, alkali metal, alkaline earth metal, silver or guanidinium salts thereof, and/or esters thereof.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: December 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 4958045
    Abstract: A process for the preparation of a 1,8-bridged 4-quinolone-3-carboxylic acid of the formula ##STR1## comprising in a first reaction step reacting an enamine of the formula ##STR2## in an anhydrous, aprotic solvent with one equivalent of a base, at a temperature from 80.degree. C. to 180.degree. C., to give a 4-quinolone-3-carboxylic acid derivative of the formula ##STR3## and, in a second reaction step, reacting that with another equivalent of a base, to give the 1,8-bridged 4-quinolone-3-carboxylic acid derivative of the formula (I) and optionally converting the group Y into a carboxyl group or salt thereof. Both steps may be effected simultaneously in a one-pot process without intermediate isolation of the compound II. Some of the compounds are new. The old and new compounds are antibacterials and promote animal growth.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: September 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Michael Schriewer
  • Patent number: 4956465
    Abstract: As novel intermediates for antibacterials, the quinolone- and 1,8-naphthyridine-4-one-carboxylic acids which are C-bonded in the 7-position of the formula ##STR1## in which Y represents a carboxyl group, a nitrile group, an ester group --COOR.sup.3, or an acid amide group --CONR.sup.4 R.sup.5, where R.sup.3 stands for C.sub.1 -C.sub.4 -alkyl,X.sup.2 stands for hydrogen, nitro, alkyl having 1 to 3 carbon atoms and halogen, in particularR.sup.1 can be alkyl having 1-4 carbon atoms, vinyl, halogenoalkyl, hydroxyalkyl, cycloalkyl having 1-6 carbon atoms or optionally substituted phenyl,R.sup.2 stands for hydrogen, alkyl having 1-3 carbon atoms which is optionally substituted by halogen, alkoxy having 1-2 carbon atoms or nitro, phenyl and for a radical ##STR2## and Z.sup.1 and Z.sup.2 can each be hydrogen or various organic radicals or together form a ring,and salts and esters thereof.
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: September 11, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Uwe Petersen
  • Patent number: 4914228
    Type: Grant
    Filed: June 21, 1988
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 4908366
    Abstract: 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, alkyl or halogenX.sup.4 can be hydrogen or halogen, or alkyl,R.sup.4 and R.sup.5, together with the nitrogen atom to which they are bonded, form a 5- or 6-membered heterocyclic ring which can additionally contain the atoms or groups --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## as ring members or the group ##STR3## can also represent a ring system of the structure ##STR4## which can optionally be substituted on the ring carbons by methyl and pharmaceutically usable hydrates, salts or esters thereof.These compounds have a high antibacterial activity and are therefore suitable as active compounds for human and veterinary medicine.
    Type: Grant
    Filed: January 14, 1988
    Date of Patent: March 13, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Uwe Petersen, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: D324095
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 18, 1992
    Assignee: Hans Grohe GmbH & Co. KG
    Inventor: Klaus Grohe
  • Patent number: D329912
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: September 29, 1992
    Assignee: Hans Grohe GmbH & Co. KG
    Inventor: Klaus Grohe