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: 4386089Abstract: .beta.-Lactam compounds of the formula ##STR1## in which B denotes an optionally substituted heterocyclic 5-membered or 6-membered ring or an optionally substituted phenyl ring,Z denotes a hydrogen atom or a C.sub.1 to C.sub.4 alkoxy group, ##STR2## Y, E.sub.1 and E.sub.2 independently of one another denote a divalent organic radical andR.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another denote a hydrogen atom or an alkyl, alkenyl, alkinyl, alkadienyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aryl or heterocyclyl radical, it also being possible for the above-mentioned radicals, with the exception of hydrogen, to be substituted, or an acyl radical,are antibacterial agents with a broad antibacterial spectrum and are useful as agents for promoting growth and for improving feed utilization in animals and as antioxidants.Type: GrantFiled: June 24, 1981Date of Patent: May 31, 1983Assignee: Bayer AktiengesellschaftInventors: Hans-Bodo Konig, Karl G. Metzger, Michael Preiss
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Patent number: 4344939Abstract: New penicillin 1,1-dioxides of the formula ##STR1## or a salt thereof, in which R.sub.1 denotes a hydrogen atom or an ester-forming radical,R.sub.2 denotes a hydrogen atom,R.sub.3 denotes a hydrogen atom,R.sub.4 denotes a hydrogen atom, an optionally substituted naphthyl radical or a radical of the general formula ##STR2## and the remaining variables can be various organic radicals.Type: GrantFiled: May 29, 1980Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Ekkehard Niemers, Hans-Bodo Konig, Wilfried Schrock, Karl G. Metzger
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Patent number: 4344955Abstract: Anti-bacterially active penicillin 1,1-dioxides of the formula ##STR1## or a salt thereof, in which R.sub.1 denotes a hydrogen atom or an ester-forming radical,R.sub.2 denotes a hydrogen atom or optionally substituted alkoxy group,R.sub.3 denotes a hydrogen atom, COR.sub.4, SO.sub.2 -alkyl, SO.sub.2 -aryl or an optionally substituted alkyl group, but R.sub.2 and R.sub.3 do not simultaneously denote hydrogen atoms, andR.sub.4 denotes a hydrogen atom or any of many possible organic radicals.The compounds are also inhibitors of .beta.-lactamases so they can be used in conjunction with .beta.-lactamase-susceptible antibiotics. They are useful in fighting bacterial infection, in promoting animal growth and in preserving various materials.Type: GrantFiled: June 12, 1980Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Ekkehard Niemers, Hans-Bodo Konig, Wilfried Schrock, Karl G. Metzger
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Patent number: 4338434Abstract: 2-Hetero-acetamido-penicillanates and cephalosporinates of the formula ##STR1## in which R is hydrogen or lower alkoxy,Z is ##STR2## R.sup.1 and R .sup.2 independently or together are various radicals, A is --CH.sub.2 --CH.sub.2 --,--CH.sub.2 --CH.sub.2 --CH.sub.2 -- or ##STR3## n is 1 or 2, X is S,O,SO,SO.sub.2 or --CH.sub.2 --,Y is the balance of a penicillin or cephalosporin moiety, andB is a heterocyclic radical, in the form of the acid, a hydrate thereof, a salt thereof or a salt of the hydrate, exhibit marked anti-bacterial properties rendering them suited for use as antibiotics and animal feed supplements.Type: GrantFiled: June 4, 1979Date of Patent: July 6, 1982Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Hans-Bodo Konig, Karl G. Metzger, Peter Feyen
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Patent number: 4335114Abstract: The invention relates to sisomicin derivatives defined below in Formula (I) and a process for the preparation of said derivatives. Also included in the invention are compositions containing said derivatives and methods for using said derivatives and compositions.Type: GrantFiled: June 20, 1980Date of Patent: June 15, 1982Assignee: Bayer AktiengesellschaftInventors: Eckart Voss, Karl G. Metzger, Hans-Joachim Zeiler, Uwe Petersen, Peter Stadler
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Patent number: 4312859Abstract: The invention relates to sesomycin derivatives of Formula I, infra as well as processes for preparing said sisomycin derivatives. Also included in the invention are compositions containing said sisomycin derivatives and methods for the use of said compounds and compositions. The sisomycon derivatives are useful as antibacterial agents of broad activity and reduced side effects.Type: GrantFiled: May 8, 1980Date of Patent: January 26, 1982Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Karl G. Metzger, Hans-Joachim Zeiler, Peter Stadler, Eckart Voss
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Patent number: 4294827Abstract: New .beta.-lactam antibiotics carrying a terminal -ylidene-2-pyrrolidinon-1-yl radical and of the formula ##STR1## in which A and A' represent hydrogen, optionally substituted alkyl, aryl or a group of the formula R.sub.1 --X'in whichX' denotes a --CO-- or --SO.sub.2 -- group andR.sub.1 denotes hydrogen, optionally substituted alkyl, aryl, thienyl, furyl, amino, monoalkylamino, dialkylamino, pyrrolidyl or piperidyl, it being furthermore possible for R.sub.1 to denote alkoxy if X' represents the --CO-- group;R represents H or OCH.sub.3B represents phenyl, methylphenyl, chlorophenyl, hydroxyphenyl, furyl or the radical ##STR2## X represents S, O, SO, SO.sub.2 or --CH.sub.2 --; and Y represents the group ##STR3## in which the carbon atom which carries the carboxyl group is bonded to the nitrogen atom of the .beta.Type: GrantFiled: December 20, 1977Date of Patent: October 13, 1981Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Karl G. Metzger
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Patent number: 4289771Abstract: The invention relates to 3-sulphonyl-benzo-1,2,4-triazines and their 1-oxides, useful as antibacterial and antifungal agents. Also included in the invention are methods for the preparation of said benzo-1,2,4-triazine compounds, pharmaceutical compositions containing said benzo-1,2,4-triazines and methods for the use of said compounds and compositions.Type: GrantFiled: February 29, 1980Date of Patent: September 15, 1981Assignee: Bayer AktiengesellschaftInventors: Klaus Sasse, Ingo Haller, Manfred Plempel, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4284629Abstract: 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: February 1, 1979Date of Patent: August 18, 1981Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4251524Abstract: Antibacterially active and animal feedstuff supplement .beta.-lactam antibiotics of the formula ##STR1## in which R is H or --UR',U is O or S,R' is optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl or cycloalkyl, ##STR2## R.sup.1 and R.sup.2 individually are hydrogen or, individually or together with the carbon atom to which they are bonded, are any of various radicals,A is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or ##STR3## B is optionally substituted phenyl or is cyclohexenyl or cyclohexadienyl; X is S, O, SO, SO.sub.2 or --CH.sub.Type: GrantFiled: June 29, 1979Date of Patent: February 17, 1981Assignee: Bayer AktiengesellschaftInventors: Peter Feyen, Michael Preiss, Karl G. Metzger
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Patent number: 4235774Abstract: New penicillin derivatives, or esters or salts thereof, of the formula ##STR1## in which R is H or alkoxy,B is a heterocyclic radical,A is an ethylene, trimethylene or o-phenylene radical,D is --co-- or a direct bond, andZ is a hydrogen atom, an optionally substituted alkyl or alkenyl group, an optionally substituted cycloalkyl, cycloalkenyl or cycloalkadienyl group, an optionally substituted aryl group, an optionally substituted hetercyclyl group or an acyl radical.Type: GrantFiled: February 12, 1979Date of Patent: November 25, 1980Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Hans-Bodo Konig, Karl G. Metzger, Gunter Schmidt
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Patent number: 4234572Abstract: The invention relates to 1-N-4,6-di-O-(aminoglycosyl)-1,3-diamino-cyclitol derivatives useful as antimicrobial agents. Also included in the invention are methods for preparing said derivatives, the provision of pharmaceutical compositions containing said derivatives and methods for the use of said derivatives and compositions.Type: GrantFiled: November 13, 1978Date of Patent: November 18, 1980Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Eckart Voss, Karl G. Metzger, Peter Stadler
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Patent number: 4224315Abstract: The invention includes, as novel compounds, aminoglycoside antibiotics of the 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols which are 3-N"-substituted. Also included in the invention are compositions containing said novel compounds and methods for the use of said compounds and compositions.Type: GrantFiled: August 7, 1978Date of Patent: September 23, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Stadler, Karl G. Metzger, Uwe Petersen, Eckart Voss
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Patent number: 4223037Abstract: New .beta.-lactam antibiotics of the formula ##STR1## in which A is hydrogen or methoxy,B is phenyl optionally substituted by hydroxyl, halogen, methoxy, --CN and/or CH.sub.3 --SO.sub.2 --; thienyl; cyclohexenyl; 1,4-cyclohexadien-1-yl; or furyl,E is oxygen or sulphur,n is an integer having a value of 1 or 2,Y is a group of the formula ##STR2## T is hydrogen, alkyl--CO--O--, hydroxyl, pyridinium, aminopyridinium, carbamoyloxy, azido, cyano, optionally N-substituted thiocarbamoylthio, optionally substituted-S-phenyl, or a --S--Het group in which Het represents an optionally substituted heterocyclic 5-membered or 6-membered ring,U is oxygen, sulphur or --CH.sub.2 --,Z is a group of the formula ##STR3## R.sup.1, R.sup.2 and R.sup.3 each is hydrogen or various organic radicals, i.e.Type: GrantFiled: April 26, 1978Date of Patent: September 16, 1980Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Karl G. Metzger
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Patent number: 4218451Abstract: New penicillins of the formula ##STR1## in which ##STR2## E is oxygen or sulphur, and R.sub.1 and R.sub.2 are hydrogen or various organic radicals with certain provisos,or salts thereof, are antibacterially ative and useful as antibiotics in pharmacy, as animal feed supplements for promoting growth, and as preservatives.Type: GrantFiled: June 29, 1978Date of Patent: August 19, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Feyen, Hans-Bodo Konig, Karl G. Metzger
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Patent number: 4215118Abstract: 2-Hetero-acetamido-penicillanates and cephalosporinates of the formula ##STR1## in which R is hydrogen or lower alkoxy,Z is ##STR2## R.sup.1 and R.sup.2 independently or together are various radicals, A is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or ##STR3## n is 1 or 2, X is S,O,SO,SO.sub.2 or --CH.sub.2 --,Y is the balance of a penicillin or cephalosporin moiety, andB is a heterocyclic radical, in the form of the acid, a hydrate thereof, a salt thereof or a salt of the hydrate, exhibit marked anti-bacterial properties rendering them suited for use as antibiotics and animal feed supplements.Type: GrantFiled: July 10, 1978Date of Patent: July 29, 1980Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Hans-bodo Konig, Karl G. Metzger, Peter Feyen
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Patent number: 4208412Abstract: .beta.-Lactam compounds of the formula ##STR1## in which A is hydrogen or methoxy,B is phenyl; phenyl substituted by at least one of hydroxyl, halogen, methoxy, -CN and CH.sub.3 -SO.sub.2 -; thienyl; cyclohexenyl; 1,4-cyclohexadien-1-yl; or furyl;E is oxygen or sulphur;n is 1 or 2,Y is ##STR2## or a salt thereof, in which the carbon atom which carries the carboxyl group is bonded to the nitrogen atom of the .beta.-lactam ring,T is hydrogen, alkyl-CO--O--, hydroxyl-, pyridinium, aminopyridinium, carbamoyloxy, azido, cyano, optionally N-substituted thiocarbamoylthio, optionally substituted S-phenyl, or a --S--Het group,Het is an optionally substituted heterocyclic 5-membered or 6-membered ring;U is oxygen, sulphur or --CH.sub.2 --; andZ is an optionally substituted aromatic or pseudoaromatic ring which contains at least one nitrogen atom via which it is bonded to the N.sub.3 of the imidazolidinone radical of the .beta.-lactam,are suitable as antibiotics, growth promoters for animals and preservatives.Type: GrantFiled: April 26, 1978Date of Patent: June 17, 1980Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Karl G. Metzger
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Patent number: 4200576Abstract: Antibacterially active and animal feedstuff supplement .beta.-lactam antibiotics of the formula ##STR1## in which R is H or --UR',U is O or S,R' is optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl or cycloalkyl,Z is ##STR2## R.sup.1 and R.sup.2 individually are hydrogen or, individually or together with the carbon atom to which they are bonded, are any of various radicals,A is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or ##STR3## B is optionally substituted phenyl or is cyclohexenyl or cyclohexadienyl; X is S, O, SO, SO.sub.2 or --CH.sub.Type: GrantFiled: December 20, 1977Date of Patent: April 29, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Feyen, Michael Preiss, Karl G. Metzger
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Patent number: 4190722Abstract: The invention includes selectively acylated or sulphenylated 4,6-O-(aminoglycosyl)-1,3-diaminocyclitols (and methods for their preparation). Also included in the invention are 1-N-acylated-derivatives, such as 1-N-formyl-sisomicin, useful because of the anti-bacterial effects (and methods for their procurement). The invention includes, furthermore, methods for the procurement of said 1-N-acylated or sulphenylated derivatives, compositions containing them and methods for their use.Type: GrantFiled: June 6, 1978Date of Patent: February 26, 1980Assignee: Bayer AktiengesellschaftInventors: Eckart Voss, Peter Stadler, Uwe Petersen, Hans-Joachim Kabbe, Karl G. Metzger
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Patent number: 4147693Abstract: 6-[.alpha.-(Imidazolidin-2-on-1-ylcarbonylamino)-substutited acetamido]penicillanic acids, and the correspondingly 7-substituted ceph-3-em-4-carboxylic acids, characterized by the presence of a methyleneamino or substituted methyleneamino group on the 3-nitrogen atom of the imidazolidine ring are antibacterial agents. The compounds, of which 6-[.alpha.-(3-benzaliminoimidazolidin-2-on-1-ylcarbonylamino)cyclohe xa-1,4-dien-1-ylacetamido]penicillanic acid and 7-[.alpha.-(3-furylideneaminoimidazolidin-2-on-1-ylcarbonylamino)phenylace tamido]-3-(3-methylthiadiazol-5-ylthiomethyl)ceph-3-em-4-carboxylic acid are typical examples, are prepared through acylation of an 6-[.alpha.-(amino)substituted acetamido]penicillanic acid or the corresponding 7-[.alpha.-(amino)substituted acetamido]ceph-3-em-4-carboxylic acid with a reactive nucleofugic derivative of a 3-methyleneaminoimidazolidin-2-on-1-carboxylic acid.Type: GrantFiled: November 13, 1975Date of Patent: April 3, 1979Assignee: Bayer AktiengesellschaftInventors: Hans-Bodo Konig, Karl G. Metzger, Michael Preiss, Wilfried Schrock