Patents by Inventor Gerardus Karel Maria Verzijl

Gerardus Karel Maria Verzijl 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).

  • Publication number: 20220235058
    Abstract: Disclosed is a process for the preparation of certain intermediates, e.g. process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, in an enantioenriched form, which intermediate and processes are useful in the preparation of a BTK inhibitor, such as ibrutinib.
    Type: Application
    Filed: May 20, 2020
    Publication date: July 28, 2022
    Inventors: Philip James PYE, Andras HORVATH, Laurent LEFORT, Bernardus KAPTEIN, Gerardus Karel Maria VERZIJL, Yuanyuan YUAN, Jinxiong SU
  • Patent number: 10047019
    Abstract: The present invention relates to a process of the asymmetric hydrogenation of an unsaturated ketone or aldehyde by molecular hydrogen in the presence of at least one chiral iridium complex and in the presence of at least one additive and a halogenated alcohol. This process yields chiral compounds in a very efficient way and is very advantageous in that the amount of iridium complex can be remarkably reduced.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: August 14, 2018
    Assignee: DSM IP ASSETS B.V.
    Inventors: Jonathan Alan Medlock, Gerardus Karel Maria Verzijl, Edwin Gerard Ijpeij, Andreas Hendrikus Maria De Vries
  • Patent number: 9611200
    Abstract: The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)-isomers of 6,10,14-trimethylpentadeca-5,9,13-trien-2-one or 6,10,14-trimethylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: April 4, 2017
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Johannes Tschumi, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Patent number: 9573872
    Abstract: The present invention relates to a process of manufacturing compound having stereogenic centers from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centers. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: February 21, 2017
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Patent number: 9561989
    Abstract: The present invention relates to a process of the asymmetric hydrogenation of a ketal of an unsaturated ketone or an acetal of an unsaturated aldehyde by molecular hydrogen in the presence of at least one chiral iridium complex. This process yields chiral compounds in a very efficient way and is very advantageous in that the amount of iridium complex can be remarkably reduced.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: February 7, 2017
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Patent number: 9458076
    Abstract: The present invention relates to a process of manufacturing compound having stereogenic centers from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centers. The process involves two asymmetric hydrogenation steps. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: October 4, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Patent number: 9452961
    Abstract: The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: September 27, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Johannes Tschumi, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
  • Publication number: 20160185702
    Abstract: The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
    Type: Application
    Filed: December 18, 2013
    Publication date: June 30, 2016
    Inventors: Werner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, René Tobias STEMMLER, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20160185683
    Abstract: The present invention relates to a process of the asymmetric hydrogenation of a ketal of an unsaturated ketone or an acetal of an unsaturated aldehyde by molecular hydrogen in the presence of at least one chiral iridium complex. This process yields chiral compounds in a very efficient way and is very advantageous in that the amount of iridium complex can be remarkably reduced.
    Type: Application
    Filed: December 18, 2013
    Publication date: June 30, 2016
    Inventors: Werner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20150329457
    Abstract: The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimetylpentadecan-2-one in a multistep synthesis from 6,10-dimetylundec-5-en-2-one or 6,10-dimetylundeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
    Type: Application
    Filed: December 18, 2013
    Publication date: November 19, 2015
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, René Tobias STEMMLER, Johannes TSCHUMI, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20150329456
    Abstract: The present invention relates to a process of manufacturing (6R,10R)-6,10,14-trimethylpentadecan-2-one in a multistep synthesis from a mixture of (5E,9E)-, (5E,9Z)-, (5Z,9E)- and (5Z.9Z)-isomers of 6,10,14-trimethylpentadeca-5,9,13-trien-2-one or 6,10,14-trimethylpentadeca-5,9-dien-2-one. The process is very advantageous in that it forms in an efficient way the desired chiral product from a mixture of stereoisomers of the starting product.
    Type: Application
    Filed: December 18, 2013
    Publication date: November 19, 2015
    Inventors: Werner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, René Tobias STEMMLER, Johannes TSCHUMI, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20150321971
    Abstract: The present invention relates to a process of the asymmetric hydrogenation of an unsaturated ketone or aldehyde by molecular hydrogen in the presence of at least one chiral iridium complex and in the presence of at least one additive and a halogenated alcohol. This process yields chiral compounds in a very efficient way and is very advantageous in that the amount of iridium complex can be remarkably reduced.
    Type: Application
    Filed: December 18, 2013
    Publication date: November 12, 2015
    Inventors: Jonathan Alan MEDLOCK, Gerardus Karel Maria VERZIJL, Edwin Gerard IJPEIJ, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20150321986
    Abstract: The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves two asymmetric hydrogenation steps. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.
    Type: Application
    Filed: December 18, 2013
    Publication date: November 12, 2015
    Inventors: Werner BONRATH, Thomas NETSCHER, Jonathan Alan MEDLOCK, René Tobias STEMMLER, Gerardus Karel Maria VERZIJL, Andreas Hendrikus Maria DE VRIES
  • Publication number: 20130252288
    Abstract: The invention relates to a process for the preparation of a chiral compound, comprising enantioselectively reducing a carbon-carbon double bond of an ?,?-unsaturated compound in a mixture comprising both an E isomer and a Z isomer of the ?,?-unsaturated compound, wherein both E isomer and Z isomer are converted in the presence of a hydrogenation catalyst.
    Type: Application
    Filed: July 11, 2008
    Publication date: September 26, 2013
    Inventors: Stefaan Marie André De Wildeman, Henricus Martinus Maria Straatman, Gerardus Karel Maria Verzijl, Linda M. Vermote, Andreas Hendrikus Maria De Vries
  • Patent number: 8314238
    Abstract: The present invention relates to a process for the preparation of the compound of formula (7) which process comprises the hydrogenation of the compound of formula (4) using bis[chloro-1,5-cyclooctadiene-iridium], (S)-i-dicyclohexylphosphino-2-[(S)-?-(dimethylamino)-2-(dicyclohexylphosphino)benzyl]-ferrocene as a catalyst.
    Type: Grant
    Filed: December 23, 2008
    Date of Patent: November 20, 2012
    Assignee: Actelion Pharmaceuticals Ltd.
    Inventors: Erhard Bappert, Andreas Hendrikus Maria De Vries, Doris Domin, Matthias Helms, Christoph Imboden, Zarghun Nazir, Wolfgang Skranc, Felix Spindler, Michael Stanek, Wilhelm Tschebull, Gerardus Karel Maria Verzijl
  • Patent number: 8088954
    Abstract: The invention relates to a compound according to Formula (IX) and salts thereof, wherein R1, R2 and R5 are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, or when the compound according to formula (IX) is a salt, R1 and/or R2 may be a cation, R3, and R4 each independently selected from hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, and wherein any two of R1, R2, R3, R4 and R5 are optionally linked together to form a ring structure. The invention further relates to the preparation of such a compound and to the use of such a compound for preparing a pharmaceutical compound, an agrochemical compound, an intermediate for a pharmaceutical compound or an intermediate for an agrochemical compound.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: January 3, 2012
    Assignee: DSM IP Assets B.V.
    Inventors: Gerardus Karel Maria Verzijl, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries, Lizette Schmieder, Jeroen Antonius Franciscus Boogers
  • Publication number: 20110294171
    Abstract: The invention relates to a compound according to Formula (IX) and salts thereof, wherein R1, R2 and R5 are each independently selected from H and hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, or when the compound according to formula (IX) is a salt, R1 and/or R2 may be a cation, R3, and R4 each independently selected from hydrocarbon moieties, which hydrocarbon moieties optionally comprise one or more heteroatoms, and which hydrocarbons optionally comprise substituents, and wherein any two of R1, R2, R3, R4 and R5 are optionally linked together to form a ring structure. The invention further relates to the preparation of such a compound and to the use of such a compound for preparing a pharmaceutical compound, an agrochemical compound, an intermediate for a pharmaceutical compound or an intermediate for an agrochemical compound.
    Type: Application
    Filed: August 8, 2011
    Publication date: December 1, 2011
    Applicant: DSM IP Assets B.V.
    Inventors: Gerardus Karel Maria Verzijl, Henricus Martinus Maria Gerardus Straatman, Andreas Hendrikus Maria De Vries, Lizette Schmieder, Jeroen Antonius Franciscus Boogers
  • Publication number: 20110244531
    Abstract: The invention relates to a process for the preparation of compounds that are important building blocks in convergent synthesis routes to 2(S),4(S),5(S),7(S)-2,7-dialkyl-4-hydroxy-5-amino-8-aryl-octanoyl amides or pharmaceutically acceptable salts thereof, such as the compound Aliskiren, and to a process for the preparation of these octanoyl amides, comprising reacting said building block.
    Type: Application
    Filed: July 23, 2009
    Publication date: October 6, 2011
    Inventors: Andreas Hendrikus Maria De Vries, Gerardus Karel Maria Verzijl, Petrus Johannes Hermsen, Anna Maria Cornelia Francisca Castelijns
  • Patent number: 7884223
    Abstract: The invention relates to an enantiomerically enriched chiral compound comprising a transition metal M, which comprises four, five or six coordinating groups of which at least one pair is linked together to form a bidentate ligand, in which M is directly bound via one single ?-bond to a carbon atom of an optionally substituted and/or optionally fused (hetero)aromatic ring of said bidentate ligand and in which M is directly bound to a nitrogen atom of a primary or secondary amino group of said bidentate ligand, thereby forming a metallacycle between said bidentate ligand and the metal M, said metal M being selected from the metals of groups 8 and 9 of the Periodic Table of the Elements, in particular iron, ruthenium, osmium, cobalt, rhodium, or iridium. The chiral compound can be used as a catalyst, preferably in an asymmetric transfer hydrogenation process.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: February 8, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Johannes Gerardus (Hans) De Vries, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries, Vincent Ritleng, Adeline Marie Joseèphe Voelklin
  • Publication number: 20100304451
    Abstract: The invention relates to a process for preparing an enantiomerically and/or diastereomerically enriched ester or thioester having at least two adjacent chiral centres, wherein a mixture of stereoisomers of a secondary alcohol or thiol having a structure comprising a first chiral center forming a secondary alcohol or secondary thiol moiety in the beta position relative to a second chiral center having one hydrogen substituent, is reacted with an acyl donor in the presence of an epimerisation catalyst and a stereoselective acylation catalyst.
    Type: Application
    Filed: October 15, 2008
    Publication date: December 2, 2010
    Inventors: Gerardus Karel Maria Verzijl, Peter Jan Leonard Mario Quaedflieg, Quirinus Bernardus Broxterman