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).

  • Patent number: 4386210
    Abstract: 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: Grant
    Filed: May 4, 1981
    Date of Patent: May 31, 1983
    Assignee: Roussel Uclaf
    Inventor: Rene Heymes
  • Patent number: 4374834
    Abstract: 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: Grant
    Filed: March 26, 1981
    Date of Patent: February 22, 1983
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4328225
    Abstract: 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: Grant
    Filed: July 10, 1980
    Date of Patent: May 4, 1982
    Assignee: Roussel Uclaf
    Inventors: Michel Vignau, Rene Heymes
  • Patent number: 4307090
    Abstract: 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: Grant
    Filed: January 24, 1980
    Date of Patent: December 22, 1981
    Assignee: Roussel Uclaf
    Inventors: Michael Vignau, Rene Heymes
  • Patent number: 4297352
    Abstract: 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: Grant
    Filed: November 29, 1979
    Date of Patent: October 27, 1981
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4288434
    Abstract: 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: Grant
    Filed: March 14, 1978
    Date of Patent: September 8, 1981
    Assignee: Roussel Uclaf
    Inventor: Rene Heymes
  • Patent number: 4287193
    Abstract: 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: Grant
    Filed: April 3, 1979
    Date of Patent: September 1, 1981
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4283396
    Abstract: 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: Grant
    Filed: June 22, 1978
    Date of Patent: August 11, 1981
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4278793
    Abstract: 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: Grant
    Filed: July 21, 1980
    Date of Patent: July 14, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Durckheimer, Dieter Bormann, Eberhard Ehlers, Elmar Schrinner, Rene Heymes
  • Patent number: 4260747
    Abstract: 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: Grant
    Filed: November 29, 1978
    Date of Patent: April 7, 1981
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4202893
    Abstract: 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: Grant
    Filed: May 12, 1977
    Date of Patent: May 13, 1980
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4196205
    Abstract: 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: Grant
    Filed: June 30, 1978
    Date of Patent: April 1, 1980
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4152432
    Abstract: 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: Grant
    Filed: July 19, 1977
    Date of Patent: May 1, 1979
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4097595
    Abstract: 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: Grant
    Filed: January 12, 1977
    Date of Patent: June 27, 1978
    Assignee: Roussel Uclaf
    Inventor: Rene Heymes
  • Patent number: 4053597
    Abstract: 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: Grant
    Filed: November 25, 1975
    Date of Patent: October 11, 1977
    Assignee: Roussel-UCLAF
    Inventors: Jacques Martel, Rene Heymes, Andre Lutz
  • Patent number: 4047917
    Abstract: 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: Grant
    Filed: September 20, 1976
    Date of Patent: September 13, 1977
    Assignee: Saint-Gobain Industries
    Inventors: Pierre Rene Heymes, Rudolf Pelzer
  • Patent number: 4016158
    Abstract: 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: Grant
    Filed: January 2, 1975
    Date of Patent: April 5, 1977
    Assignee: Roussel-UCLAF
    Inventors: Jacques Martel, Rene Heymes
  • Patent number: 3990876
    Abstract: 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: Grant
    Filed: January 15, 1975
    Date of Patent: November 9, 1976
    Assignee: Saint-Gobain Industries
    Inventors: Pierre Rene Heymes, Rudolf Pelzer
  • Patent number: 3962223
    Abstract: 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: Grant
    Filed: January 2, 1973
    Date of Patent: June 8, 1976
    Assignee: Roussel-UCLAF
    Inventors: Jacques Martel, Rene Heymes
  • Patent number: 3940354
    Abstract: 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: Grant
    Filed: January 25, 1974
    Date of Patent: February 24, 1976
    Assignee: Roussel-UCLAF
    Inventors: Jacques Martel, Rene Heymes, Andre Lutz