Patents by Inventor Ryan HEESBEEN

Ryan HEESBEEN 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: 11957763
    Abstract: The invention relates to a novel linker for use in bioconjugates such as antibody-drug-conjugates. The linker according to the invention is represented by formula: wherein: BM is a branching moiety; E is a capping group; SG is a sulfamide group; b, c, d, e, g, i, k, l are independently 0 or 1; f is an integer in the range of 1 to 10; Sp1, Sp2, Sp3, Sp4, Sp5 and Sp6 are a spacer moieties; Z1 and Z2 are connecting groups. The linker according to the invention is useful in the preparation of linker-conjugates and bioconjugates, and can be used for (a) improving conjugation efficiency in the preparation of the bioconjugate, (b) reducing aggregation during the preparation of the bioconjugate and/or of the bioconjugate, (c) increasing stability of the bioconjugate, and/or (d) increasing therapeutic index of the bioconjugate.
    Type: Grant
    Filed: December 28, 2020
    Date of Patent: April 16, 2024
    Assignee: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan Van Berkel, Ryan Heesbeen, Jorge Merijn Mathieu Verkade, Maria Antonia Wijdeven, Floris Louis Van Delft
  • Publication number: 20230127659
    Abstract: The present invention concerns novel and improved antibody-conjugates for targeting HER2. The inventors found that when antibody-conjugates were prepared using a specific mode of conjugation, they exhibit an improved therapeutic index.
    Type: Application
    Filed: May 20, 2022
    Publication date: April 27, 2023
    Applicant: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan VAN BERKEL, Jorge Merijn Mathieu VERKADE, Maria Antonia WIJDEVEN, Ryan HEESBEEN, Petrus Josephus Jacobus Maria VAN DE SANDE, Remon VAN GEEL, Brian Maria Gerardus JANSSEN, Inge Catharina Josephina HURKMANS, Floris Louis VAN DELFT
  • Patent number: 11590239
    Abstract: The present invention concerns novel and improved antibody-conjugates for targeting CD30. The inventors found that when antibody-conjugates were prepared using a specific mode of conjugation, they exhibit an improved therapeutic index.
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: February 28, 2023
    Assignee: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan Van Berkel, Jorge Merijn Mathieu Verkade, Maria Antonia Wijdeven, Ryan Heesbeen, Petrus Josephus Jacobus Maria Van De Sande, Remon Gvan Eel, Brian Maria Gerardus Janssen, Inge Catharina Josephina Hurkmans, Floris Louis Van Delft
  • Patent number: 11338043
    Abstract: The present invention concerns novel and improved antibody-conjugates for targeting HER2. The inventors found N that when antibody-conjugates were prepared using a specific mode of conjugation, they exhibit an improved therapeutic index.
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: May 24, 2022
    Assignee: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan Van Berkel, Jorge Merijn Mathieu Verkade, Maria Antonia Wijdeven, Ryan Heesbeen, Petrus Josephus Jacobus Maria Van De Sande, Remon Van Geel, Brian Maria Gerardus Janssen, Inge Catharina Josephina Hurkmans, Floris Louis Van Delft
  • Publication number: 20210353766
    Abstract: The invention relates to a novel linker for use in bioconjugates such as antibody-drug-conjugates. The linker according to the invention is represented by formula: wherein: BM is a branching moiety; E is a capping group; SG is a sulfamide group; b, c, d, e, g, i, k, l are independently 0 or 1; f is an integer in the range of 1 to 10; Sp1, Sp2, Sp3, Sp4, Sp5 and Sp6 are a spacer moieties; Z1 and Z2 are connecting groups. The linker according to the invention is useful in the preparation of linker-conjugates and bioconjugates, and can be used for (a) improving conjugation efficiency in the preparation of the bioconjugate, (b) reducing aggregation during the preparation of the bioconjugate and/or of the bioconjugate, (c) increasing stability of the bioconjugate, and/or (d) increasing therapeutic index of the bioconjugate.
    Type: Application
    Filed: December 28, 2020
    Publication date: November 18, 2021
    Applicant: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan VAN BERKEL, Ryan HEESBEEN, Jorge Merijn Mathieu VERKADE, Maria Antonia WIJDEVEN, Floris Louis VAN DELFT
  • Patent number: 10874746
    Abstract: The invention relates to a novel linker for use in bioconjugates such as antibody-drug-conjugates. The linker according to the invention is represented by formula: (I) wherein: —BM is a branching moiety; —E is a capping group; —SG is a sulfamide group; —b, c, d, e, g, i, k, l are independently 0 or 1; —f is an integer in the range of 1 to 10; —Sp1, Sp2, Sp3, Sp4, Sp5 and Sp6 are a spacer moieties; —Z1 and Z2 are connecting groups. The linker according to the invention is useful in the preparation of linker-conjugates and bioconjugates, and can be used for (a) improving conjugation efficiency in the preparation of the bioconjugate, (b) reducing aggregation during the preparation of the bioconjugate and/or of the bioconjugate, (c) increasing stability of the bioconjugate, and/or (d) increasing therapeutic index of the bioconjugate.
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: December 29, 2020
    Assignee: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan Van Berkel, Ryan Heesbeen, Jorge Merijn Mathieu Verkade, Maria Antonia Wijdeven, Floris Louis Van Delft
  • Publication number: 20190262466
    Abstract: The present invention concerns novel and improved antibody-conjugates for targeting HER2. The inventors found N that when antibody-conjugates were prepared using a specific mode of conjugation, they exhibit an improved therapeutic index.
    Type: Application
    Filed: February 8, 2017
    Publication date: August 29, 2019
    Applicant: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan VAN BERKEL, Jorge Merijn Mathieu VERKADE, Maria Antonia WIJDEVEN, Ryan HEESBEEN, Petrus Josephus Jacobus Maria VAN DE SANDE, Remon VAN GEEL, Brian Maria Gerardus JANSSEN, Inge Catharina Josephina HURKMANS, Floris Louis VAN DELFT
  • Publication number: 20190262468
    Abstract: The present invention concerns novel and improved antibody-conjugates for targeting CD30. The inventors found that when antibody-conjugates were prepared using a specific mode of conjugation, they exhibit an improved therapeutic index.
    Type: Application
    Filed: February 8, 2017
    Publication date: August 29, 2019
    Inventors: Sander Sebastiaan VAN BERKEL, Jorge Merijn Mathieu VERKADE, Maria Antonia WIJDEVEN, Ryan HEESBEEN, Petrus Josephus Jacobus Maria VAN DE SANDE, Remon GVAN EEL, Brian Maria Gerardus JANSSEN, Inge Catharina Josephina HURKMANS, Floris Louis VAN DELFT
  • Publication number: 20190225706
    Abstract: The invention relates to a glycoprotein comprising an optionally fucosylated glycan according to formula (105) or (106), wherein Su(A)x is a modified sugar moiety comprising one or more functional groups A. Functional group A is independently selected from the group consisting of a thiol group, a halogen, a sulfonyloxy group, a halogenated acetamido group, a mercaptoacetamido group and a sulfonated hydroxyacetamido group. The invention also relates to a glycoprotein-conjugate wherein a glycoprotein according to the invention is conjugated to a molecule of interest. Said molecule of interest may for example be an active substance. The invention further relates to a process for the preparation of a modified glycoprotein, and to a method for the preparation of a glycoprotein-conjugate. The invention particularly relates to modified antibodies, antibody-conjugates, antibody-drug conjugates and methods for the preparation thereof.
    Type: Application
    Filed: August 28, 2018
    Publication date: July 25, 2019
    Applicant: SynAffix B.V.
    Inventors: Floris Louis VAN DELFT, Remon VAN GEEL, Maria Antonia WIJDEVEN, Jorge Merijn Mathieu VERKADE, Ryan HEESBEEN
  • Patent number: 10266502
    Abstract: The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (hetero)cyclooctyne. The invention also relates to the cycloaddition products obtainable by the process according to the invention. The invention further relates to halogenated aliphatic 1,3-dipole compounds, in particular to halogenated aliphatic 1,3-dipole compounds comprising N-acetylgalactosamine-UDP (GalNAc-UDP), and to halogenated 1,3-dipole compounds comprising (peracylated) N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), N-acetylmannosamine (ManNAc) and N-acetyl neuraminic acid (NeuNAc).
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: April 23, 2019
    Assignee: SYNAFFIX B.V.
    Inventors: Floris Louis Van Delft, Remon Van Geel, Maria Antonia Wijdeven, Ryan Heesbeen
  • Publication number: 20190038765
    Abstract: The invention relates to a novel linker for use in bioconjugates such as antibody-drug-conjugates. The linker according to the invention is represented by formula: (I) wherein: —BM is a branching moiety; —E is a capping group; —SG is a sulfamide group; —b, c, d, e, g, i, k, l are independently 0 or 1; —f is an integer in the range of 1 to 10; —Sp1, Sp2, Sp3, Sp4, Sp5 and Sp6 are a spacer moieties; —Z and Z2 are connecting groups. The linker according to the invention is useful in the preparation of linker-conjugates and bioconjugates, and can be used for (a) improving conjugation efficiency in the preparation of the bioconjugate, (b) reducing aggregation during the preparation of the bioconjugate and/or of the bioconjugate, (c) increasing stability of the bioconjugate, and/or (d) increasing therapeutic index of the bioconjugate.
    Type: Application
    Filed: February 8, 2017
    Publication date: February 7, 2019
    Applicant: SYNAFFIX B.V.
    Inventors: Sander Sebastiaan VAN BERKEL, Ryan HEESBEEN, Jorge Merijn Mathieu VERKADE, Maria Antonia WIJDEVEN, Floris Louis VAN DELFT
  • Patent number: 10072096
    Abstract: The invention relates to a glycoprotein comprising an optionally fucosylated glycan according to formula (105) or (106), wherein Su(A)x is a modified sugar moiety comprising one or more functional groups A. Functional group A is independently selected from the group consisting of a thiol group, a halogen, a sulfonyloxy group, a halogenated acetamido group, a mercaptoacetamido group and a sulfonated hydroxyacetamido group. The invention also relates to a glycoprotein-conjugate wherein a glycoprotein according to the invention is conjugated to a molecule of interest. Said molecule of interest may for example be an active substance. The invention further relates to a process for the preparation of a modified glycoprotein, and to a method for the preparation of a glycoprotein-conjugate. The invention particularly relates to modified antibodies, antibody-conjugates, antibody-drug conjugates and methods for the preparation thereof.
    Type: Grant
    Filed: October 14, 2014
    Date of Patent: September 11, 2018
    Assignee: SYNAFFIX B.V.
    Inventors: Floris Louis Van Delft, Remon Van Geel, Maria Antonia Wijdeven, Jorge Merijn Mathieu Verkade, Ryan Heesbeen
  • Publication number: 20170009266
    Abstract: The present invention relates to a process for attaching an N-acetylgalactosamine-(hetero)arylmoiety to an N-acetylglucosaminemoiety, the process comprising the step of contacting the N-acetylgalactosamine-(hetero)arylmoiety with the N-acetylglucosaminemoiety in the presence of a mutant galactosyltransferase, wherein the N-acetylglucosaminemoiety is according to Formula (1) the N-acetylgalactosamine-(hetero)arylmoiety is according to Formula (2): In a particularly preferred embodiment of the process according to the invention, the N-acetylgalactosamine-(hetero)arylmoiety comprises a 1,3-dipole functional group, and the N-acetylglucosaminemoiety is a terminal GlcNAc moiety of a glycoprotein glycan. The invention further relates to a product obtainable by the process according to the invention, in particular to glycoproteins. Also, the invention relates to several compounds comprising an N-acetylgalactosamine-(hetero)arylmoiety.
    Type: Application
    Filed: January 26, 2015
    Publication date: January 12, 2017
    Applicant: SynAffix B.V.
    Inventors: Floris Louis VAN DELFT, Remon VAN GEEL, Maria Antonia WIJDEVEN, Ryan HEESBEEN
  • Publication number: 20170008858
    Abstract: The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (hetero)cyclooctyne. The invention also relates to the cycloaddition products obtainable by the process according to the invention. The invention further relates to halogenated aliphatic 1,3-dipole compounds, in particular to halogenated aliphatic 1,3-dipole compounds comprising N-acetylgalactosamine-UDP (GalNAc-UDP), and to halogenated 1,3-dipole compounds comprising (peracylated) N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), N-acetylmannosamine (ManNAc) and N-acetyl neuraminic acid (NeuNAc).
    Type: Application
    Filed: January 26, 2015
    Publication date: January 12, 2017
    Applicant: SynAffix B.V.
    Inventors: Floris Louis VAN DELFT, Remon VAN GEEL, Maria Antonia WIJDEVEN, Ryan HEESBEEN
  • Publication number: 20160280797
    Abstract: The invention relates to a glycoprotein comprising an optionally fucosylated glycan according to formula (105) or (106), wherein Su(A)x is a modified sugar moiety comprising one or more functional groups A. Functional group A is independently selected from the group consisting of a thiol group, a halogen, a sulfonyloxy group, a halogenated acetamido group, a mercaptoacetamido group and a sulfonated hydroxyacetamido group. The invention also relates to a glycoprotein-conjugate wherein a glycoprotein according to the invention is conjugated to a molecule of interest. Said molecule of interest may for example be an active substance. The invention further relates to a process for the preparation of a modified glycoprotein, and to a method for the preparation of a glycoprotein-conjugate. The invention particularly relates to modified antibodies, antibody-conjugates, antibody-drug conjugates and methods for the preparation thereof.
    Type: Application
    Filed: October 14, 2014
    Publication date: September 29, 2016
    Applicant: SynAffix B.V.
    Inventors: Floris Louis VAN DELFT, Remon VAN GEEL, Maria Antonia WIJDEVEN, Jorge Merijn Mathieu VERKADE, Ryan HEESBEEN
  • Publication number: 20160235861
    Abstract: The invention relates to glycoengineered antibodies and antibody-conjugates. In particular, the invention relates to an antibody conjugate, prepared from IgG antibody comprising at least two N-linked glycosylation sites on the combination of a single heavy chain and single light chain. The invention further relates to methods for the preparation of the antibody-conjugates according to the invention. In particular, the invention relates to an antibody-drug conjugate that is conjugated to different toxins, and the a process for the preparation thereof.
    Type: Application
    Filed: October 14, 2014
    Publication date: August 18, 2016
    Applicant: SynAffix. B.V.
    Inventors: Floris Louis VAN DELFT, Remon VAN GEEL, Maria Antonia WIJDEVEN, Jorge Merijn Mathieu VERKADE, Ryan HEESBEEN