Patents by Inventor Reinhard Karge

Reinhard Karge 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: 9108925
    Abstract: The present invention relates to a novel process for the manufacture of Grewe-diamine comprising the following step: hydrolyzing a compound of formula (II), wherein R is hydrogen or straight- or branched chain C1-4 alkyl, with an aqueous alkali or alkaline-earth metal hydroxide solution, characterized in that the hydrolysis is carried out in the presence of an organic solvent.
    Type: Grant
    Filed: January 24, 2006
    Date of Patent: August 18, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Jocelyn Fischesser, Lisa Giraudi, Reinhard Karge
  • Patent number: 8921605
    Abstract: Use of pure lanthanum oxide which is obtained by calcination of oxygen-containing lanthanum salts at temperatures of at least 700° C. as heterogeneous catalyst in the aldol condensation of citral and acetone to give pseudoionone, and process for the preparation of pseudoionone by aldol condensation of citral and acetone in the liquid phase using pure lanthanum oxide.
    Type: Grant
    Filed: July 19, 2011
    Date of Patent: December 30, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Wolfgang Hölderich, Verena Ritzerfeld, Bernhard Markus Ernst Russbüldt, Erhard Henning Fleischhauer, Werner Bonrath, Reinhard Karge, Jan Schütz
  • Patent number: 8802898
    Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.
    Type: Grant
    Filed: April 18, 2011
    Date of Patent: August 12, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
  • Patent number: 8658793
    Abstract: A process for the preparation of 5-substituted 4-amino-2-methylpyrimidines of the formula wherein R is CONH2 or CN, and of acid addition salts thereof, characterized in that a compound of formula H2N—CH?C(R) CN (II) is reacted with acetimidic acid methyl ester or an acid addition salt thereof and that, if desired, a compound of formula I is transferred into an acid addition salt, and the transformation of a compound of formula II wherein R is CONH2 into a compound of formula II wherein R is CN by treatment with POCl3.
    Type: Grant
    Filed: May 13, 2013
    Date of Patent: February 25, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Reinhard Karge, Jan Schultz
  • Publication number: 20130310607
    Abstract: Use of pure lanthanum oxide which is obtained by calcination of oxygen-containing lanthanum salts at temperatures of at least 700° C. as heterogeneous catalyst in the aldol condensation of citral and acetone to give pseudoionone, and process for the preparation of pseudoionone by aldol condensation of citral and acetone in the liquid phase using pure lanthanum oxide.
    Type: Application
    Filed: July 19, 2011
    Publication date: November 21, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Wolfgang Hölderich, Verena Ritzerfeld, Bernhard Markus Ernst Russbüldt, Erhard Henning Fleischhauer, Werner Bonrath, Reinhard Karge, Jan Schütz
  • Publication number: 20130245263
    Abstract: A process for the preparation of 5-substituted 4-amino-2-methylpyrimidines of the formula wherein R is CONH2 or CN, and of acid addition salts thereof, characterized in that a compound of formula H2N—CH?C(R) CN (II) is reacted with acetimidic acid methyl ester or an acid addition salt thereof and that, if desired, a compound of formula I is transferred into an acid addition salt, and the transformation of a compound of formula II wherein R is CONH2 into a compound of formula II wherein R is CN by treatment with POCl3.
    Type: Application
    Filed: May 13, 2013
    Publication date: September 19, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Reinhard KARGE, Jan SCHULTZ
  • Publication number: 20130197272
    Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.
    Type: Application
    Filed: April 18, 2011
    Publication date: August 1, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
  • Patent number: 8461168
    Abstract: A process for the preparation of 5-substituted 4-amino-2-methylpyrimidines of the formula (I) wherein R is CONH2 or CN, and of acid addition salts thereof, characterized in that a compound of formula H2N CH?C(R)CN (II) is reacted with acetimidic acid methyl ester or an acid addition salt thereof and that, if desired, a compound of formula (I) is transferred into an acid addition salt, and the transformation of a compound of formula (II) wherein R is CONH2 into a compound of formula (II) wherein R is CN by treatment with POCI3.
    Type: Grant
    Filed: April 8, 2010
    Date of Patent: June 11, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Reinhard Karge, Jan Schütz
  • Patent number: 8252927
    Abstract: The present invention is directed to a process for the manufacture of compounds of formula IV wherein R1 is an amino protecting group, and R2 is hydrogen or C1-10 alkyl, comprising a) reacting a compound of formula Ia, wherein M+ is a cation, preferably selected from the group consisting of Li+, Na+, K+, ½ Mg2+ and ½ Zn2+, (formula 1a) with an ammonium salt NH4+X?, wherein X? is an anion, preferably selected from the group consisting of chloride, bromide, sulfate and acetate, in a solvent to a compound of formula II b) reacting a compound of formula II with a nitrile R2—CN in the presence of a base to a compound of formula IV. The present invention is further directed to compounds of formula II and their use for the manufacture of vitamin B1.
    Type: Grant
    Filed: July 22, 2009
    Date of Patent: August 28, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Reinhard Karge, Ulla Letinois, Gerhard Shiefer
  • Publication number: 20120172617
    Abstract: A process for the preparation of 1-(3,5-diacetoxyphenyl)-ethanol by catalytic hydrogenation of 3,5-diacetoxy-acetophenone in the presence of a Ni-alloy as catalyst in a C1-3-carboxylic acid ester as solvent.
    Type: Application
    Filed: January 6, 2010
    Publication date: July 5, 2012
    Inventors: Werner Bonrath, Ulla Letinois, Reinhard Karge, Max Hugentobler
  • Patent number: 8198443
    Abstract: Process for the manufacture of a compound of the structure (I) with R1=hydrogen, alkyl (C1-C10, linear, cyclic or branched, aliphatic or aromatic), NR?R? (wherein R? and R? are independently selected from H, alkyl [C1-C10, linear, cyclic or branched, aliphatic or aromatic] and R2=CH2R3 wherein R3 is selected from NHR1?? (with R??=C(O)H, C(O)CH3, C(O)alkyl, CH2C6H2(OMe)3 or other saponifiable residues), alkyl (C1-C10, linear, cyclic or branched) aromatic residues, heteroaryl residues, substituted aryl residues, e.g. 3,4,5-trimethoxy-phenyl) wherein 1 equivalent of an ?-formyl-propionitrile salt is reacted with 0.75 to 2 equivalents of an acetamidine salt in the presence of a Lewis acid.
    Type: Grant
    Filed: January 7, 2008
    Date of Patent: June 12, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Ralph Haerter, Reinhard Karge, Ulla Letinois
  • Publication number: 20120095230
    Abstract: A process for the preparation of 5-substituted 4-amino-2-methylpyrimidines of the formula (I) wherein R is CONH2 or CN, and of acid addition salts thereof, characterized in that a compound of formula H2N CH?C(R) CN (II) is reacted with acetimidic acid methyl ester or an acid addition salt thereof and that, if desired, a compound of formula (I) is transferred into an acid addition salt, and the transformation of a compound of formula (II) wherein R is CONH2 into a compound of formula (II) wherein R is CN by treatment with POCI3.
    Type: Application
    Filed: April 8, 2010
    Publication date: April 19, 2012
    Inventors: Reinhard Karge, Jan Schutz
  • Patent number: 8110702
    Abstract: The invention relates to an improved process for the manufacture of substitute 2-cyanocinnamic esters. This novel economical process provides products in high purity and yields.
    Type: Grant
    Filed: September 24, 2010
    Date of Patent: February 7, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Jing Huang, Shuping Jing, Reinhard Karge, Ralf Proplesch
  • Patent number: 7985870
    Abstract: The invention relates to an improved process for the manufacture of substituted 2-cyanocinnamic esters. This novel economical process provides products in high purity and yields.
    Type: Grant
    Filed: January 18, 2008
    Date of Patent: July 26, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Jing Huang, Shuping Jing, Reinhard Karge, Ralf Proplesch
  • Publication number: 20110178300
    Abstract: The present invention is directed to a process for the manufacture of compounds of formula IV wherein R1 is an amino protecting group, and R2 is hydrogen or C1-10 alkyl, comprising a) reacting a compound of formula Ia, wherein M+ is a cation, preferably selected from the group consisting of Li+, Na+, K+, ms, ½ Mg2+ and ½ Zn2+, (formula 1a) with an ammonium salt NH4X?, wherein X? is an anion, preferably selected from the group consisting of chloride, bromide, sulfate and acetate, in a solvent to a compound of formula II b) reacting a compound of formula II with a nitrile R2—CN in the presence of a base to a compound of formula IV. The present invention is further directed to compounds of formula II and their use for the manufacture of vitamin B1.
    Type: Application
    Filed: July 22, 2009
    Publication date: July 21, 2011
    Inventors: Reinhard Karge, Ulla Letinois, Gerhard Shiefer
  • Patent number: 7935829
    Abstract: The present invention relates to a process for the manufacture of cyclic thio esters (thiolactones) and related compounds by hydrogenation of cyclic thioanhydrides in the presence of metal catalysts.
    Type: Grant
    Filed: April 12, 2006
    Date of Patent: May 3, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Felix Roessler
  • Publication number: 20110014140
    Abstract: The invention relates to an improved process for the manufacture of substitute 2-cyanocinnamic esters. This novel economical process provides products in high purity and yields.
    Type: Application
    Filed: September 24, 2010
    Publication date: January 20, 2011
    Inventors: Jing HUANG, Shuping Jing, Reinhard Karge, Ralf Proplesch
  • Patent number: 7803952
    Abstract: The present invention relates to a process for the manufacture of cyclic monocarboxylic esters (lactones) and related compounds by hydrogenation of cyclic dicarboxylic acid anhydrides in the presence of metal catalysts.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: September 28, 2010
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Reinhard Karge, Felix Roessler
  • Publication number: 20100048937
    Abstract: The invention relates to an improved process for the manufacture of substituted 2-cyanocinnamic esters. This novel economical process provides products in high purity and yields.
    Type: Application
    Filed: January 18, 2008
    Publication date: February 25, 2010
    Inventors: Jing Huang, Shuping Jing, Reinhard Karge, Ralf Proplesch
  • Publication number: 20100016591
    Abstract: Process for the manufacture of a compound of the structure (I) with R1=hydrogen, alkyl (C1-C10, linear, cyclic or branched, aliphatic or aromatic), NR?R? (wherein R? and R? are independently selected from H, alkyl [C1-C10, linear, cyclic or branched, aliphatic or aromatic] and R2=CH2R3 wherein R3 is selected from NHR1?? (with R??=C(O)H, C(O)CH3, C(O)alkyl, CH2C6H2(OMe)3 or other saponifiable residues), alkyl (C1-C10, linear, cyclic or branched) aromatic residues, heteroaryl residues, substituted aryl residues, e.g. 3,4,5-trimethoxy-phenyl) wherein 1 equivalent of an ?-formyl-propionitrile salt is reacted with 0.75 to 2 equivalents of an acetamidine salt in the presence of a Lewis acid.
    Type: Application
    Filed: January 17, 2008
    Publication date: January 21, 2010
    Inventors: Werner Bonrath, Ralph Haerter, Reinhard Karge, Ulla Letinois