Patents by Inventor Rene Heymes
Rene Heymes 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: 4386210Abstract: Novel syn isomers of 7-amino-thiazolyl-acetamido-3-acetoxymethyl-cephalosporanic acid derivatives of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of --CN, --CONH.sub.2 and --COOR.sub.1 ', R.sub.1 ' is selected from the group consisting of alkyl of 1 to 3 carbon atoms, hydrogen, alkali metal, alkaline earth metal, ammonium, magnesium and a non-toxic, pharmaceutically acceptable organic amine, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, ammonium, magnesium and a non-toxic, pharmaceutically acceptable organic amine, R' and R" are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms with the ##STR2## group in the syn position with the proviso that when R.sub.1 is --COOR.sub.1 ' and R.sub.1 ' is hydrogen, A is hydrogen and when R.sub.1 is --COOR.sub.1 ' and R.sub.Type: GrantFiled: May 4, 1981Date of Patent: May 31, 1983Assignee: Roussel UclafInventor: Rene Heymes
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Patent number: 4374834Abstract: Novel syn isomers of 7-[2-(2-amino-4-thiazolyl)-2-(carboxymethyloxyimino)-acetamido]-ceph-3-eme -4-carboxylic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 3 carbon atoms and --CH.sub.2 --S--R.sub.1, R.sub.1 is an optionally substituted heterocyclic of 5 to 6 chain components with 1 to 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an easily cleavable ester and a non-toxic, pharmaceutically acceptable organic amine, A.sub.1 is selected from the group consisting of alkyl of 1 to 3 carbon atoms, hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an easily cleavable ester and a non-toxic, pharmaceutically acceptable organic amine and non-toxic, pharmaceutically acceptable acid addition salts thereof having antibiotic activity and their preparation and intermediates therefor.Type: GrantFiled: March 26, 1981Date of Patent: February 22, 1983Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4328225Abstract: Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO.sup.- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.Type: GrantFiled: July 10, 1980Date of Patent: May 4, 1982Assignee: Roussel UclafInventors: Michel Vignau, Rene Heymes
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Patent number: 4307090Abstract: Novel oximes of the syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, acetoxymethyl, carbamoyloxymethyl, ##STR2## A1K is 1 to 4 carbon atoms, azidomethyl and --CH.sub.2 --S--R' and R' is selected from the group consisting of a nitrogen heterocycle optionally substituted, acyl of an alkanoic acid of 2 to 4 carbon atoms, 2-oxo-(3H)-thiazolin-4-yl-carbonyl and 3-methyl-1,2-oxazol-5-ylcarbonyl, n is an integer from 2 to 4, R.sub.1, R.sub.2 and R.sub.3 are individually alkyl of 1 to 4 carbon atoms or together taken with the nitrogen atom they are attached to form a group selected from the group consisting of 1,4-diazobicyclo (2,2,2)octan-1-ylium and 1,3,5,7-tetraazatricyclo(3,3,1,1.sup.Type: GrantFiled: January 24, 1980Date of Patent: December 22, 1981Assignee: Roussel UclafInventors: Michael Vignau, Rene Heymes
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Patent number: 4297352Abstract: Novel syn isomers of 3-substituted-7-amino-thiazolyl-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and --CH.sub.2 --S--R.sub.1, R.sub.1 is selected from the group consisting of 2-methyl-1,3,4-thiadiazolyl, 1-methyl tetrazolyl, acyl of an organic carboxylic acid of 2 to 4 carbon atoms and ##STR2## R.sub.2 is selected from the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms and A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium and a non-toxic, pharmaceutically acceptable organic amine having antibiotic activity and novel intermediates and process for their preparation.Type: GrantFiled: November 29, 1979Date of Patent: October 27, 1981Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4288434Abstract: Novel syn isomers of 7-amino-thiazolyl-acetamido-3-acetoxymethyl-cephalosporanic acid derivatives of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of --CN, --CONH.sub.2 and --COOR.sub.1 ', R.sub.1 ' is selected from the group consisting of alkyl of 1 to 3 carbon atoms, hydrogen, alkali metal, alkaline earth metal, ammonium, magnesium and a non-toxic, pharmaceutically acceptable organic amine, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, ammonium, magnesium and a non-toxic, pharmaceutically acceptable organic amine, R' and R" are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms with the ##STR2## group in the syn position with the proviso that when R.sub.1 is --COOR.sub.1 ' and R.sub.1 ' is hydrogen, A is hydrogen and when R.sub.1 is --COOR.sub.1 ' and R.sub.Type: GrantFiled: March 14, 1978Date of Patent: September 8, 1981Assignee: Roussel UclafInventor: Rene Heymes
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Patent number: 4287193Abstract: Novel syn isomers of 7-[2-(2-amino-4-thiazolyl)-2-(carboxymethyloxyimino)-acetamido]-ceph-3-eme -4-carboxylic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 3 carbon atoms and --CH.sub.2 --S--R.sub.1, R.sub.1 is an optionally substituted heterocyclic of 5 to 6 chain components with 1 to 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an easily cleavable ester and a non-toxic, pharmaceutically acceptable organic amine, A.sub.1 is selected from the group consisting of alkyl of 1 to 3 carbon atoms, hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an easily cleavable ester and a non-toxic, pharmaceutically acceptable organic amine and non-toxic, pharmaceutically acceptable acid addition salts thereof having antibiotic activity and their preparation and intermediates therefor.Type: GrantFiled: April 3, 1979Date of Patent: September 1, 1981Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4283396Abstract: Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.Type: GrantFiled: June 22, 1978Date of Patent: August 11, 1981Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4278793Abstract: Cephem derivatives of the general formula ##STR1## in which the R.sub.2 O group is in the syn-position, a process for their manufacture and pharmaceutical formulations which are active against bacterial infections and contain these compounds.Type: GrantFiled: July 21, 1980Date of Patent: July 14, 1981Assignee: Hoechst AktiengesellschaftInventors: Walter Durckheimer, Dieter Bormann, Eberhard Ehlers, Elmar Schrinner, Rene Heymes
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Patent number: 4260747Abstract: Novel syn isomers of 3-substituted-7-amino-thiazolyl-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and --CH.sub.2 --S--R.sub.1, R.sub.1 is selected from the group consisting of 2-methyl-1,3,4-thiadiazolyl, 1-methyl tetrazolyl, acyl of an organic carboxylic acid of 2 to 4 carbon atoms and ##STR2## R.sub.2 is selected from the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms and A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium and a non-toxic, pharmaceutically acceptable organic amine having antibiotic activity and novel intermediates and process for their preparation.Type: GrantFiled: November 29, 1978Date of Patent: April 7, 1981Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4202893Abstract: Novel alkyloximes of 7-amino-thiazolyl-acetamidocephalosporanic acids of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and --CH.sub.2 --SR', R' is selected from the group consisting of acyl of an alkanoic acid of 2 to 4 carbon atoms, 1-methyl-tetrazolyl and 2-methyl-1,3,4-thiadiazolyl, R.sub.1 is selected from the group consisting of hydrogen and a group easily removeable by acid hydrolysis or hydrogenolysis, R.sub.2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, an alkali metal cation, an equivalent of an alkaline earth metal or magnesium, an organic amine base cation and an ester group easily removeable by acid hydrolysis or hydrogenolysis with the proviso that when R.sub.1 is hydrogen, A is not an ester group easily removeable by hydrogenolysis or acid hydrolysis and the wavy line means that OR.Type: GrantFiled: May 12, 1977Date of Patent: May 13, 1980Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4196205Abstract: Compounds of the formula ##STR1## wherein R is hydrogen, R' is selected from the group consisting of alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base and the OR' group is in the syn position having antibiotic activity and process for their preparation.Type: GrantFiled: June 30, 1978Date of Patent: April 1, 1980Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4152432Abstract: Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.Type: GrantFiled: July 19, 1977Date of Patent: May 1, 1979Assignee: Roussel UclafInventors: Rene Heymes, Andre Lutz
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Patent number: 4097595Abstract: Novel 7-amino-thiazolyl-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and a group easily removable by acid hydrolysis or hydrogenolysis, R.sub.1 is selected from the group consisting of alkyl of 1 to 4 carbon atoms, a 5 member heterocyclic ring and a 5 member heterocyclic ring containing a ketone group and A is selected from the group consisting of hydrogen, alkali metal and equivalents of alkaline earth metals, magnesium and organic amine having antibiotic activity against gram negative and gram positive bacteria and their preparation and novel intermediates therefore.STATE OF THE ARTFrench Pat. No. 2,255,077 of Takeda describes antibacterial cephalosporins having a different substitutent in the 3-position.Type: GrantFiled: January 12, 1977Date of Patent: June 27, 1978Assignee: Roussel UclafInventor: Rene Heymes
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Patent number: 4053597Abstract: Cephalosporan compounds of the formula ##STR1## in the form of racemic mixtures or optically active isomers or in the form of their cis or trans isomers or mixtures thereof wherein R is selected from the group consisting of phenyl substituted with at least one hydroxyl and sydnone optionally substituted with phenyl, R' is selected from the group consisting of hydrogen and R", R" is an ester group easily removable by acid hydrolysis or hydrogenolysis, R.sub.1 and R.sub.2 are alkyl of 1 to 3 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of amino and Y', Y' is hydrogen and NHCOOZ, Z is straight or branched alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable addition salts with organic and inorganic acids and bases where appropriate with the proviso that when Y is amino, R' is hydrogen and when Y is amino or NHCOOZ, R is phenyl which have antibacterial activity and their preparation.Type: GrantFiled: November 25, 1975Date of Patent: October 11, 1977Assignee: Roussel-UCLAFInventors: Jacques Martel, Rene Heymes, Andre Lutz
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Patent number: 4047917Abstract: An apparatus for making films, sheets or plates of a transparent plastics material of high optical quality comprises means for depositing a solution, molten mass or reaction mixture which yields the solid plastics on drying or hardening on a moving glass ribbon having a smooth upper surface. The ribbon may be made by the float glass process. The plurality of plastics layer may be deposited one on another.Type: GrantFiled: September 20, 1976Date of Patent: September 13, 1977Assignee: Saint-Gobain IndustriesInventors: Pierre Rene Heymes, Rudolf Pelzer
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Patent number: 4016158Abstract: Novel desacetoxycephalosporin derivatives of the formula ##STR1## in racemic or optically active form or cis and trans forms and mixtures thereof wherein R is selected from the group consisting of aminophenyl and R', R' is selected from the group consisting of phenyl optionally substituted with at least one member of the group consisting of halogen and nitro and a 5 to 6 member heterocyclic group, Y is selected from the group consisting of amino, NHCOOR" where R" is alkyl of 1 to 5 carbon atoms, hydrogen and hydroxy, A is selected from the group consisting of ##STR2## in which at least 2 of R.sub.2, R.sub.3 and R.sub.4 are alkyl of 1 to 3 carbon atoms and the third is hydrogen or alkyl of 1 to 3 carbon atoms with the total number of carbon atoms being not greater than 5 and cycloalkyl of 3 to 7 carbon atoms optionally containing a heteroatom and R.sub.Type: GrantFiled: January 2, 1975Date of Patent: April 5, 1977Assignee: Roussel-UCLAFInventors: Jacques Martel, Rene Heymes
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Patent number: 3990876Abstract: An improved method of making films, sheets or plates of a transparent plastics material of high optical quality comprises depositing a solution, molten mass or reaction mixture which yields the solid plastics on drying or hardening on a moving glass ribbon having a smooth upper surfce. The ribbon may be made by the float glass process. The plurality of plastics layer may be deposited one on another.Type: GrantFiled: January 15, 1975Date of Patent: November 9, 1976Assignee: Saint-Gobain IndustriesInventors: Pierre Rene Heymes, Rudolf Pelzer
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Patent number: 3962223Abstract: Novel desacetoxycephalosporin derivatives of the formula ##EQU1## in racemic or optically active form or cis and trans forms and mixtures thereof wherein R is selected from the group consisting of aminophenyl and R', R' is selected from the group consisting of phenyl optionally substituted with at least one member of the group consisting of halogen and nitro and a 5 to 6 member heterocyclic group, Y is selected from the group consisting of amino, NHCOOR" where R" is alkyl of 1 to 5 carbon atoms, hydrogen and hydroxy, A is selected from the group consisting of alkyl of 2 to 5 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally containing a heteroatom and R.sub.1 is selected from the group consisting of hydrogen, easily acid hydrolyzable group and easily hydrogenolysis removable group, with the proviso that when R is aminophenyl Y is other than amino and NHCOOR" and R.sub.1 is hydrogen and when Y is amino, R.sub.Type: GrantFiled: January 2, 1973Date of Patent: June 8, 1976Assignee: Roussel-UCLAFInventors: Jacques Martel, Rene Heymes
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Patent number: 3940354Abstract: Cephalosporon compounds of the formula ##SPC1##In the form of racemic mixtures or optically active isomers or in the form of their cis or trans isomers or mixtures thereof wherein R is selected from the group consisting of phenyl substituted with at least one hydroxyl and sydnone optionally substituted with phenyl, R' is selected from the group consisting of hydrogen and R", R" is an ester group easily removable by acid hydrolysis or hydrogenolysis, R.sub.1 and R.sub.2 are alkyl of 1 to 3 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of amino and Y', Y' is hydrogen and NHCOOZ, Z is straight or branched alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable addition salts with organic and inorganic acids and bases where appropriate with the proviso that when Y is amino, R' is hydrogen and when Y is amino or NHCOOZ, R is phenyl which have antibacterial activity and their preparation.Type: GrantFiled: January 25, 1974Date of Patent: February 24, 1976Assignee: Roussel-UCLAFInventors: Jacques Martel, Rene Heymes, Andre Lutz