Patents by Inventor Francois Bénard

Francois Bénard 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: 20250186627
    Abstract: A compound comprising a prostate specific membrane antigen (PSMA)-targeting moiety of the following formula (I) or of a salt or a solvate thereof. R1 is —R1aR1b— wherein R1a is absent, —CH2—, —O—, or —S—, and R1b is —CH2— or —CHF—. R2 is —(CH2)3—O—, —(CH2)3—, —(CH2)4—, —CH2—O—(CH2)2—, or —CH2—S—(CH2)2. R3 is ethylene fused to a tricyclic fused ring. L1, L2, L3, L4, L5b L5c, L6 and L7 are linkages (e.g. peptide bonds). Xbr is a branching atom. Rrad is a radiometal chelator. Ralb is an albumin binder. n1, n2, n3, n4, and n5 are integers. When the PSMA-targeting moiety is linked to a radiolabeling group, the compound may be used as an imaging agent or therapeutic agent for PSMA-expressing diseases/conditions.
    Type: Application
    Filed: March 3, 2023
    Publication date: June 12, 2025
    Inventors: Kuo-Shyan LIN, François BÉNARD, Chengcheng ZHANG, Zhengxing ZHANG
  • Patent number: 12246076
    Abstract: There is provided peptidic compounds of Formula I, A or B(Rradn6-[linker]-RL-Xaa1-Xaa2-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7-Xaa8-?-Xaa9-NH2). Xaa1 is D-Phe, Cpa, D-Cpa, Nal, D-Nal, 2-Nal, or D-2-Nal; Xaa2 is Asn, Gln, Hse, Cit or His. Xaa3 is Trp, Bta, Trp(Me), Trp(7-Me), Trp(6-Me), Trp(5-Me), Trp(4-Me), Trp(2-Me), Trp(7-F), Trp(6-F), Trp(5-F), Trp(4-F), Trp(5-OH), or ?Me-Trp. Xaa4 is Ala or Ser. Xaa5 is Val, Cpg, or Tle. Xaa6 is Gly, NMe-Gly, or D-Ala. Xaa7 is His or NMe-His. Xaa8 is Leu or Phe. Xaa9-NH2 is a C-terminally amidated amino acid residue selected from Pro, 4-oxa-L-Pro, Me2 Thz, or Thz. ? represents a peptide bond or reduced peptide bond joining Xaa8 to Xaa9. Rradn6 is 1-5 radiolabeling groups. There is also provided the use of such compounds as imaging agents or therapeutic agents.
    Type: Grant
    Filed: November 17, 2023
    Date of Patent: March 11, 2025
    Assignees: PROVINCIAL HEALTH SERVICES AUTHORITY, THE UNIVERSITY OF BRITISH COLUMBIA
    Inventors: Kuo-Shyan Lin, François Bénard, Lei Wang, Zhengxing Zhang, Ivica Bratanovic, Chengcheng Zhang
  • Publication number: 20240350681
    Abstract: A compound is provided comprising a melanocortin 1 receptor (MC1R) targeting peptide (MC1RTP), a radiolabeling group, and a linker joining the MC1RTP to the radiolabeling group. The MC1RTP is linear or cyclized, and comprises a sequence of Formula I or Formula II: Xaa1-Xaa2a-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7a (I) or Xaa1-Xaa2b-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7b (I). Xaa1 is L- /D-Nle, L-/D-Nle, L-/D-Ala, L-/D-Leu, L-/D-Ile, D-Ile, L-/D-Cys, L-/D-Met, L-/D-Phe, L-/D-Trp, L-/D-Val, L-/D-Nal, L-/D-2-Nal, Gly, L-/D-?-aminobutryic acid, L-/D-norvaline, or L-/D-homonorleucine. Xaa2a and Xaa7b are L-/D-Cys, L-/D-Asp, L-/D-Glu, L-/D-2-Aad, L-/D-3-Aad, L-/D-Pra, L-/D-Hpg, or L-/D-Bpg. Xaa2b and Xaa7a are L-/D-Cys, L-/D-Lys, L-/D-Orn, L-/D-Dab, L-/D-Dap, L-/D-Lys(N3), L-/D-Om(N3), L-/D-Dab(N3), L-/D-Dap(N3), L-/D-2-(5?-azidopentyl)alanine, or L-/D-2-(6?-azidohexyl)alanine. Xaa3 is L-/D-His, Pro, beta-(1,2,3-triazol-4-yl)-L-alanine, beta-(1,2,3-triazol-4-yl)-D-alanine, 1,2,4-triazole-3-alanine, or 1,2,4-triazole-3-D-N alanine.
    Type: Application
    Filed: April 19, 2024
    Publication date: October 24, 2024
    Inventors: François BÉNARD, Kuo-Shyan LIN, Chengcheng ZHANG, Zhengxing ZHANG, Jutta ZEISLER
  • Publication number: 20240342321
    Abstract: The present disclosure relates to peptidic compounds of Formula A, A-II, A-III, B, or C, or salt or solvate thereof, compositions thereof, and methods of use thereof. The compounds of the present disclosure are useful for targeting CXCR4 for purposes such as imaging and/or therapeutics.
    Type: Application
    Filed: June 27, 2024
    Publication date: October 17, 2024
    Inventors: François BÉNARD, Kuo-Shyan LIN, Zhengxing ZHANG, Daniel KWON, David PERRIN, Mijhajlo TODOROVIC, Jerome LOZADA, Lee Lee LI
  • Publication number: 20240309070
    Abstract: Provided are antibodies that specifically bind to Vaccinia Virus B5 antigen (VV B5). In certain embodiments, the anti-VV B5 antibodies are humanized antibodies. Fusion proteins and conjugates comprising such antibodies are also provided. Pharmaceutical compositions comprising the antibodies, fusion proteins and conjugates of the present disclosure are also provided, as are methods of using such compositions, e.g., for therapy, in vivo imaging and/or the like. In certain aspects, provided are methods that comprise administering an antibody, fusion protein or conjugate of the present disclosure to an individual, wherein the individual comprises cells infected with VV, and wherein the antibody, fusion protein or conjugate is targeted to the infected cells by VV B5 antigens expressed on the surface of the infected cells.
    Type: Application
    Filed: March 16, 2022
    Publication date: September 19, 2024
    Inventors: Emma J. Cummins, Jan Peter Bergqvist, Brad Nelson, Kwame Twumasi-Boateng, Yin Yu Eunice Kwok, Francois Benard, Julie Marie Rousseau, Kuo-Shyan Lin, Julian Smazynski, Sander Martinus Johannes van Duijnhoven
  • Patent number: 11992537
    Abstract: A compound is provided comprising a melanocortin 1 receptor (MC1R) targeting peptide (MC1RTP), a radiolabeling group, and a linker joining the MC1RTP to the radiolabeling group. The MC1RTP is linear or cyclized, and comprises a sequence of Formula I or Formula II: Xaa1-Xaa2a-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7a (I) or Xaa1-Xaa2b-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7b (II). Xaa1 is L-/D-Nle, L-/D-Nle, L-/D-Ala, L-/D-Leu, L-/D-Ile, D-Ile, L-/D-Cys, L-/D-Met, L-/D-Phe, L-/D-Trp, L-/D-Val, L-/D-Nal, L-/D-2-Nal, Gly, L-/D-?-aminobutryic acid, L-/D-norvaline, or L-/D-homonorleucine. Xaa2a and Xaa7b are L-/D-Cys, L-/D-Asp, L-/D-Glu, L-/D-2-Aad, L-/D-3-Aad, L-/D-Pra, L-/D-Hpg, or L-/D-Bpg. Xaa2b and Xaa7a are L-/D-Cys, L-/D-Lys, L-/D-Orn, L-/D-Dab, L-/D-Dap, L-/D-Lys(N3), L-/D-Orn(N3), L-/D-Dab(N3), L-/D-Dap(N3), L-/D-2-(5?-azidopentyl)alanine, or L-/D-2-(6?-azidohexyl)alanine. Xaa3 is L-/D-His, Pro, beta-(1,2,3-triazol-4-yl)-L-alanine, beta-(1,2,3-triazol-4-yl)-D-alanine, 1,2,4-triazole-3-alanine, or 1,2,4-triazole-3-D-alanine.
    Type: Grant
    Filed: May 23, 2019
    Date of Patent: May 28, 2024
    Assignee: PROVINCIAL HEALTH SERVICES AUTHORITY
    Inventors: François Bénard, Kuo-Shyan Lin, Chengcheng Zhang, Zhengxing Zhang
  • Publication number: 20240123099
    Abstract: There is provided peptidic compounds of Formula I, A or B(Rradn6-[linker]-RL-Xaa1-Xaa2-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7-Xaa8-?-Xaa9-NH2). Xaa1 is D-Phe, Cpa, D-Cpa, Nal, D-Nal, 2-Nal, or D-2-Nal; Xaa2 is Asn, Gln, Hse, Cit or His. Xaa3 is Trp, Bta, Trp(Me), Trp(7-Me), Trp(6-Me), Trp(5-Me), Trp(4-Me), Trp(2-Me), Trp(7-F), Trp(6-F), Trp(5-F), Trp(4-F), Trp(5-OH), or ?Me-Trp. Xaa4 is Ala or Ser. Xaa5 is Val, Cpg, or Tle. Xaa6 is Gly, NMe-Gly, or D-Ala. Xaa7 is His or NMe-His. Xaa8 is Leu or Phe. Xaa9-NH2 is a C-terminally amidated amino acid residue selected from Pro, 4-oxa-L-Pro, Me2 Thz, or Thz. ? represents a peptide bond or reduced peptide bond joining Xaa8 to Xaa9. Rradn6 is 1-5 radiolabeling groups. There is also provided the use of such compounds as imaging agents or therapeutic agents.
    Type: Application
    Filed: November 17, 2023
    Publication date: April 18, 2024
    Inventors: Kuo-Shyan LIN, François BÉNARD, Lei WANG, Zhengxing ZHANG, Ivica BRATANOVIC, Chengcheng ZHANG
  • Publication number: 20240100203
    Abstract: The present disclosure relates to peptidic compounds of Formula A, A-II, A-III, B, or C, or salt or solvate thereof, compositions thereof, and methods of use thereof. The compounds of the present disclosure are useful for targeting CXCR4 for purposes such as imaging and/or therapeutics.
    Type: Application
    Filed: October 21, 2021
    Publication date: March 28, 2024
    Inventors: François BÉNARD, Kuo-Shyan LIN, Zhengxing ZHANG, Daniel KWON, David PERRIN, Mihajlo TODOROVIC, Jerome LOZADA, Lee Lee LI
  • Patent number: 11884714
    Abstract: The invention described herein is based in part on the discovery of a protein/peptide crosslink, which introduces fluorescent properties, and which has been applied to synthesize analogues of melanocortin and amanitin as choice peptides to be explored in the context of isoindole peptides. Without limitation, it is expected that those trained in the art of peptide synthesis and stapling would appreciate the consequences of this invention such that other peptides of varied length can be similarly constrained by isoindole staples as featured herein.
    Type: Grant
    Filed: June 8, 2022
    Date of Patent: January 30, 2024
    Assignees: THE UNIVERSITY OF BRITISH COLUMBIA, PROVINCIAL HEALTH SERVICES AUTHORITY
    Inventors: David Perrin, Mihajlo Todorovic, François Bénard, Chengcheng Zhang
  • Publication number: 20240018110
    Abstract: The present invention relates to radiolabelled compounds for in vivo imaging or treatment of diseases or conditions characterized by expression of prostate-specific membrane antigen.
    Type: Application
    Filed: December 16, 2021
    Publication date: January 18, 2024
    Inventors: François BÉNARD, Kuo-Shyan LIN, Chengcheng ZHANG, David PERRIN, Aron ROXIN, Zhengxing ZHANG, Antoine DOUCHEZ, Pargol DANESHMANDKASHANI, Samson LAI
  • Publication number: 20240011179
    Abstract: A system for producing technetium-99m from molybdate-100. The system comprises: a target capsule apparatus for housing a Mo-100-coated target plate; a target capsule pickup apparatus for engaging and delivering the target cell apparatus into a target station apparatus; a target station apparatus for receiving and mounting therein the target capsule apparatus. The target station apparatus is engaged with a cyclotron for irradiating the Mo-100-coated target plate with protons. The irradiated target capsule apparatus is transferred to a receiving cell apparatus comprising a dissolution/purification module for receiving therein a proton-irradiated Mo-100-coated target plate. A conveyance conduit infrastructure interconnects: (i) the target capsule pickup apparatus with the target station apparatus, (ii) the target station apparatus and the receiving cell apparatus; and (iii) the receiving cell apparatus and the dissolution/purification module.
    Type: Application
    Filed: April 21, 2023
    Publication date: January 11, 2024
    Inventors: Paul SCHAFFER, Francois BENARD, Kenneth R. BUCKLEY, Victoire HANEMAAYER, Cornelia Manuela HOEHR, Julius Alexander KLUG, Michael S. KOVACS, Thomas J. MORLEY, Thomas J. RUTH, John VALLIANT, Stefan K. ZEISLER, Maurice G. DODD
  • Publication number: 20230348535
    Abstract: This application relates to compounds of Formula (I-a) or Formula (I-b), or is salts or solvates thereof. R1 is —(CH2)5CH3 or comprises 2-4 fused benzene rings. R2 is I, Br, F, Cl, H, OH, OCH3, NH2, NO2 or CH3. R3 is a peptide-bonded glycine, aspartate or glutamate or is glutamate peptide bonded through Cdelta. L is —CH2NH—, —(CH2)2NH—, —(CH2)3NH—, or —(CH2)4NH—. R4 is a radiometal chelator optionally bound by a radiometal. Variable ‘n’ is 1-3. The compounds may be useful for imaging prostate specific membrane antigen (PSMA)-expressing tissues or for treating PSMA-expressing diseases (e.g. cancer).
    Type: Application
    Filed: July 7, 2023
    Publication date: November 2, 2023
    Inventors: Kuo-Shyan LIN, François BÉNARD, Hsiou-Ting KUO, Zhengxing ZHANG
  • Publication number: 20230270892
    Abstract: A chelator having the general structure (I) for chelating ra-diometals such as 225Ac under mild conditions is provided. (I) The chelator can be coupled to a biological targeting moiety to facilitate targeted delivery of the chelated radiometal in a mammalian subject.
    Type: Application
    Filed: February 25, 2021
    Publication date: August 31, 2023
    Inventors: Hua YANG, Feng GAO, Paul SCHAFFER, Zheliang YUAN, Chengcheng ZHANG, Francois BENARD, Luke WHARTON
  • Patent number: 11661668
    Abstract: A system for producing technetium-99m from molybdate-100. The system comprises: a target capsule apparatus for housing a Mo-100-coated target plate; a target capsule pickup apparatus for engaging, and delivering the target cell apparatus into a target station apparatus; target station apparatus for receiving and mounting therein the target capsule apparatus. The target station apparatus is engaged with a cyclotron for irradiating the Mo-100-coated target plate with protons. The irradiated target capsule apparatus is transferred to a receiving cell apparatus comprising a dissolution/purification module for receiving therein a proton-irradiated Mo-100-coated target plate. A conveyance conduit infrastructure interconnects: (i) the target capsule pickup apparatus with the target station apparatus, (ii) the target station apparatus and the receiving cell apparatus; and (iii) the receiving cell apparatus and the dissolution/purification module.
    Type: Grant
    Filed: June 11, 2021
    Date of Patent: May 30, 2023
    Assignee: TRIUMF INC.
    Inventors: Paul Schaffer, Francois Benard, Kenneth R. Buckley, Victoire Hanemaayer, Cornelia Manuela Hoehr, Julius Alexander Klug, Michael S. Kovacs, Thomas J. Morley, Thomas J. Ruth, John Valliant, Stefan K. Zeisler, Maurice G. Dodd
  • Publication number: 20230114807
    Abstract: A compound comprising a prostate specific membrane antigen (PSMA)-targeting moiety of the following formula or of a salt or a solvate thereof. R0 is O or S. Each of R1a, R1b and R1c may be —CO2H, —SO2H, —SO3H, —PO2H, or —PO3H2, for example. R2 may be methylene or a derivative thereof, propylene or a derivative thereof, or a derivative of ethylene, optionally substituted. R3 is a linker. When the PSMA-targeting moiety is linked to a radiolabeling group, the compound may be used as an imaging agent or therapeutic agent for PSMA-expressing diseases/conditions.
    Type: Application
    Filed: October 6, 2022
    Publication date: April 13, 2023
    Inventors: Kuo-Shyan LIN, François BÉNARD, Hsiou-Ting KUO, Zhengxing ZHANG, David PERRIN
  • Publication number: 20230027475
    Abstract: Provided are antibodies that specifically bind Vaccinia Virus (VV) A56 or B5 antigen. Also provided are fusion proteins and conjugates that comprise the antibodies. Pharmaceutical compositions and kits that comprise the antibodies, fusion proteins and conjugates are also provided. Aspects of the present disclosure further include methods of using the antibodies, fusion proteins and conjugates, e.g., for therapeutic purposes. In certain embodiments, provided are methods that comprise administering an antibody, fusion protein or conjugate of the present disclosure to an individual having cancer, wherein the individual comprises cancer cells infected with VV, and wherein the antibody, fusion protein or conjugate is targeted to the infected cancer cells by VV antigens expressed on the surface of the infected cancer cells.
    Type: Application
    Filed: September 11, 2020
    Publication date: January 26, 2023
    Inventors: Emma J. Cummins, Jan Peter Bergqvist, Brad Nelson, Kwame Twumasi-Boateng, Yin Yu Eunice Kwok, Julian Smazynski, Francois Benard, Julie Marie Rousseau, Kuo-Shyan Lin
  • Patent number: 11504441
    Abstract: A compound comprising a prostate specific membrane antigen (PSMA)-targeting moiety of the following formula or of a salt or a solvate thereof. R0 is O or S. Each of R1a, R1b and R1c may be —CO2H, —SO2H, —SO3H, —PO2H, or —PO3H2, for example. R2 may be methylene or a derivative thereof, propylene or a derivative thereof, or a derivative of ethylene, optionally substituted. R3 is a linker. When the PSMA-targeting moiety is linked to a radiolabeling group, the compound may be used as an imaging agent or therapeutic agent for PSMA-expressing diseases/conditions.
    Type: Grant
    Filed: July 9, 2021
    Date of Patent: November 22, 2022
    Assignees: PROVINCIAL HEALTH SERVICES AUTHORITY, THE UNIVERSITY OF BRITISH COLUMBIA
    Inventors: Kuo-Shyan Lin, François Bénard, Hsiou-Ting Kuo, Zhengxing Zhang, David Perrin
  • Publication number: 20220298219
    Abstract: The invention described herein is based in part on the discovery of a protein/peptide crosslink, which introduces fluorescent properties, and which has been applied to synthesize analogues of melanocortin and amanitin as choice peptides to be explored in the context of isoindole peptides. Without limitation, it is expected that those trained in the art of peptide synthesis and stapling would appreciate the consequences of this invention such that other peptides of varied length can be similarly constrained by isoindole staples as featured herein.
    Type: Application
    Filed: June 8, 2022
    Publication date: September 22, 2022
    Inventors: David PERRIN, Mihajlo TODOROVIC, François BÉNARD, Chengcheng ZHANG
  • Publication number: 20220233726
    Abstract: This application relates to compounds of Formula I. R1a, R1b and R1c is —CO2H, —SO2H, —SO3H, —SO4H, —PO2H, —PO3H or —PO4H. R2 is a linker, e.g. butylene. R3 is a linkage, e.g. —O—, —S—, —S(O)—, S(O)2—, —NHC(O)—, —C(O)NH—, or 1,2,3-triazole. R4 is —(CH2)0-3CH(R7)(CH2)0-3— wherein R7 is —(CH2)5CH3 or certain aromatic fused-ring systems. R5 and R6 are hydrogen or methyl. Each Xaa1 (if present) is an amino acid. RX is a radiolabeling group, e.g.: a radiometal chelator optionally bound by a radiometal; an aryl substituted with a radioisotope; a prosthetic group containing a trifluoroborate; or a prosthetic group containing a silicon-fluorine-acceptor moiety. The compounds may be useful for imaging prostate-specific membrane antigen (PSMA)-expressing tissues or for treating PSMA-expressing diseases (e.g. cancer).
    Type: Application
    Filed: April 16, 2020
    Publication date: July 28, 2022
    Inventors: Kuo-Shyan LIN, François BÉNARD, Hsiou-Ting KUO, Helen MERKENS, Zhengxing ZHANG
  • Patent number: 11395857
    Abstract: A compound is provided comprising a melanocortin 1 receptor (MC1R) targeting peptide (MC1RTP), a radiolabeling group, and a linker joining the MC1RTP to the radio labeling group. The MC1RTP is linear or cyclized, and comprises a sequence of Formula I or Formula II: Xaa1-Xaa2a-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7a (I) or Xaa1-Xaa2b-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7b (II). Xaa1 is L-/D-Nle, L-/D-Nle, L-/D-Ala, L-/D-Leu, L-/D-Ile, D-Ile, L-/D-Cys, L-/D-Met, L-/D-Phe, L-/D-Trp, L-/D-Val, L-/D-Nal, L-/D-2-Nal, Gly, L-/D-?-aminobutryic acid, L-/D-norvaline, or L-/D-homonorleucine. Xaa2a and Xaa7b are L-/D-Cys, L-/D-Asp, L-/D-Glu, L-/D-2-Aad, L-/D-3-Aad, L-/D-Pra, L-/D-Hpg, or L-/D-Bpg. Xaa2b and Xaa7a are L-/D-Cys, L-/D-Lys, L-/D-Orn, L-/D-Dab, L-/D-Dap, L-/D-Lys(N3), L-/D-Orn(N3), L-/D-Dab(N3), L-/D-Dap(N3), L-/D-2-(5?-azidopentyl)alanine, or L-/D-2-(6?-azidohexyl)alanine. Xaa3 is L-/D-His, Pro, beta-(1,2,3-triazol-4-yl)-L-alanine, beta-(1,2,3-triazol-4-yl)-D-alanine, 1,2,4-triazole-3-alanine, or 1,2,4-triazole-3-D-alanine.
    Type: Grant
    Filed: October 5, 2021
    Date of Patent: July 26, 2022
    Assignee: PROVINCIAL HEALTH SERVICES AUTHORITY
    Inventors: François Bénard, Kuo-Shyan Lin, Chengcheng Zhang, Zhengxing Zhang