Patents Examined by Lawrence E. Crane
  • Patent number: 10961269
    Abstract: A method for preparing a compound represented by general formula I: or a salt thereof includes a step of reacting a compound represented by formula II: with a reducing agent to cleave an oxazolidine ring fused to a cycle A?. The reducing agent includes at least one of phosphines, metal hydrides, or transition metal catalysts in the presence of hydrogen gas.
    Type: Grant
    Filed: September 20, 2016
    Date of Patent: March 30, 2021
    Assignees: MITSUBISHI TANABE PHARMA CORPORATION, OSAKA UNIVERSITY
    Inventors: Satoshi Obika, Eiji Kawanishi, Hiroaki Sawamoto, Shuhei Yamakoshi, Yuuki Aral, Shinji Kumagai
  • Patent number: 10947262
    Abstract: The invention herein describes a method to purify a target oligonucleotide using hydrophobic interaction chromatography (HIC). The method includes adding a salt to a mixture of the target oligonucleotide and product-related impurities, applying the diluted mixture, at a particular dynamic loading capacity, to the hydrophobic interaction chromatography resin (or hydrophobic adsorbent), washing the hydrophobic adsorbent with an aqueous salt solution, eluting the target oligonucleotide with a eluting solution, and collecting the eluent comprising the target oligonucleotide.
    Type: Grant
    Filed: June 13, 2017
    Date of Patent: March 16, 2021
    Assignee: BIOGEN MA INC.
    Inventors: Robert S. Gronke, Ratnesh S. Joshi
  • Patent number: 10941400
    Abstract: Described herein are conjugated modified oligonucleotides that are complementary to a target RNA. The conjugate facilitates cellular uptake of the modified oligonucleotide, resulting improved potency.
    Type: Grant
    Filed: January 17, 2019
    Date of Patent: March 9, 2021
    Assignee: Regulus Therapeutics Inc.
    Inventor: Balkrishen Bhat
  • Patent number: 10933074
    Abstract: The present invention relates to methods for improving the gastrointestinal tolerance of food and beverage products comprising sweet, low-digestible carbohydrates, and the use of one or more of D-glucose, fiber and protein for improving the gastrointestinal tolerance of food and beverage products comprising sweet, low-digestible carbohydrates.
    Type: Grant
    Filed: September 21, 2016
    Date of Patent: March 2, 2021
    Assignee: Tate & Lyle Ingredients Americas LLC
    Inventors: Patricia S. Williamson, Ryan D. Woodyer
  • Patent number: 10919928
    Abstract: Oligonucleotides may be produced by a process, including (1) condensing a nucleoside, nucleotide or oligonucleotide (b), and a nucleoside, nucleotide or oligonucleotide (a), or a substituted nucleotide or oligonucleotide (?) in a non-polar solvent to give a reaction solution containing a phosphite triester product (c); (3) oxidizing or sulfurizing the phosphite triester product (c) to give a reaction solution containing an oligonucleotide (d) wherein the 5?-hydroxy group is protected; (4) deprotecting the oligonucleotide (d) to give a reaction solution containing an oligonucleotide (e) wherein the 5?-hydroxy group is not protected; and (6) adding a polar solvent to the reaction solution containing the oligonucleotide (e) and purifying the oligonucleotide (e) by solid-liquid separation, wherein said nucleoside, nucleotide or oligonucleotide (a) or said substituted nucleotide or oligonucleotide (?) is a compound represented by formula (a-i): wherein Base, Rp1, R10, m, L, Y, and Z are defined herein.
    Type: Grant
    Filed: June 15, 2018
    Date of Patent: February 16, 2021
    Assignee: AJINOMOTO CO., INC.
    Inventors: Kunihiro Hirai, Satoshi Katayama, Naoko Hirose, Taisuke Ichimaru, Ken Yamashita, Daisuke Takahashi
  • Patent number: 10912767
    Abstract: The present invention includes compounds of the class anthracycline that have been modified to include photo-activated prodrug anthracycline compounds that are useful in the treatment of cancer. One example composition of the invention may include photodoxazolidine which may be synthesized in two steps from 4,5-dimethoxy-2-nitrobenzyl alcohol and doxazolidine. In this embodiment commercial 4,5-dimethoxyl-2-nitrobenzyl alcohol reacts with p-nitrophenylchloroformate to give the p-nitrophenyl carbonate of the benzyl alcohol derivative. The p-nitrophenyl carbonate is then reacted with doxazolidine to give the exemplary photodoxazolidine composition.
    Type: Grant
    Filed: April 27, 2016
    Date of Patent: February 9, 2021
    Assignee: THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE
    Inventors: Tad H. Koch, Benjamin L. Barthel, Hang Hubert Yin, Ryo Tamura, Alla Balabanova
  • Patent number: 10907146
    Abstract: The present invention relates to a ribonucleic acid (RNA) extraction method using a solid subject, the method including activating a subject with a reactive amine group, injecting a sample having 1×101 to 1×103 cells/ml and a dimethyl suberimidate (DMS) compound or a dimethyl pimelimidate (DMP) compound into the subject, and forming a complex having the RNA within the sample and the compound, and extracting the RNA by treating elution buffer to the subject on which the complex is formed. The subject, particularly, the thin film device used for extracting the RNA, has improved hydrophilicity compared to the conventional silicon substrate, so that RNA is extracted more efficiently.
    Type: Grant
    Filed: May 15, 2017
    Date of Patent: February 2, 2021
    Assignee: INFUSION TECH
    Inventor: Yong Shin
  • Patent number: 10906929
    Abstract: This invention relates to derivatives of cladribine of Formula (I). The compounds are phosphoramidate derivatives in which the phosphoramidate moiety is situated on the 3?-hydroxyl group of cladribine. The invention also relates to pharmaceutical formulations of the cladribine derivatives and their use in methods of treatment. The compounds are useful in the treatment of cancer.
    Type: Grant
    Filed: May 31, 2017
    Date of Patent: February 2, 2021
    Assignee: NuCana plc
    Inventors: Hugh Griffith, Michaela Serpi, Magdalena Slusarczyk, Christopher McGuigan
  • Patent number: 10898738
    Abstract: Provided herein are compositions and methods for improving a visual function, e.g., eyesight, eye strain, blurred vision, dry eye, retinal function, presbyopia, or Visual Display Terminal (VDT) syndrome, that is safe for long-term intake and ensures effective improvement of visual function. The compositions include a nicotinamide mononucleotide (structure shown below) as an active ingredient.
    Type: Grant
    Filed: September 13, 2017
    Date of Patent: January 26, 2021
    Inventors: Megumi Tanaka, Tsunemaru Tanaka
  • Patent number: 10874685
    Abstract: The present disclosure provides a novel method for treating pancreatic cancer and pancreatitis in which a combination of a dopamine receptor antagonist (pimozide, haloperidol, and/or L-741,626), 2-deoxy-D-glucose and atorvastatin are used, optionally in combination with gemcitabine.
    Type: Grant
    Filed: August 12, 2019
    Date of Patent: December 29, 2020
    Assignees: THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY, DEUTSCHES KREBSFORSCHUNGSZENTRUM STIFTUNG DES ÖFFENTLICHEN RECHTS
    Inventors: Pouria Jandaghi, Yasser Riaz Alhosseini, Daniel Scott Auld, Veena Sangwan
  • Patent number: 10870674
    Abstract: The present invention is directed to modified oligonucleotides having the following Formula (I) wherein one or more of phosphate groups are substituted at phosphorus, and methods for their synthesis. The modified oligonucleotides are useful for diagnostic applications involving sequence specific recognition of a nucleic acid and for use in a method of medical treatment.
    Type: Grant
    Filed: August 28, 2014
    Date of Patent: December 22, 2020
    Assignee: Noogen LLC
    Inventors: Dmitry Stetsenko, Maxim Kupryushkin, Dmitrii Pyshnyi
  • Patent number: 10836787
    Abstract: The present invention relates to novel salts and crystalline forms of (S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate having the structure: for use in treating viral infections. One crystalline form of the compound can be characterized by an X-ray powder diffraction (XRPD) pattern having peaks at 22.3°, 16.9°, and 16.2° 2-?±0.2° 2-?. In some embodiments, the viral infection is caused by a virus selected from the group consisting of Arenaviridae, Coronaviridae, Filoviridae, Flaviviridae, and Paramyxoviridae.
    Type: Grant
    Filed: April 27, 2018
    Date of Patent: November 17, 2020
    Assignee: Gilead Sciences, Inc.
    Inventors: Katrien Brak, Ernest A. Carra, Lars V. Heumann, Nate Larson
  • Patent number: 10821060
    Abstract: A process and composition for improvement of the moisturization state of the stratum corneum of human skin epidermis comprising applying to the skin an effective amount of a composition (C) for topical use comprising at least one cosmetically acceptable excipient and a composition C1 consisting of 20-50% by weight of composition C2, which in turn includes from 3-25% by weight of a polyol, from 25-45% by weight anhydrides of the polyol, and from 30-72% by weight of polyol glycosides of the polyol, with the remainder of composition C2 to 100% by weight being made up of water; and from 50-80% by weight of glycerol and/or glycerol oligomers, with the ratio of polyol glycosides to glycerol and/or glycerol oligomers greater than or equal to 1/10 and less than or equal to 1/2.
    Type: Grant
    Filed: April 28, 2017
    Date of Patent: November 3, 2020
    Assignee: SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC
    Inventors: Armelle Berge, Laetitia Cattuzzato, Sandy Dumont
  • Patent number: 10808246
    Abstract: The present invention relates to ligand conjugates of iRNA agents (such as siRNA) of the formula
    Type: Grant
    Filed: July 11, 2014
    Date of Patent: October 20, 2020
    Assignee: ALNYLAM PHARMACEUTICALS, INC.
    Inventors: Muthiah Manoharan, Jayaprakash K. Nair, Pachamuthu Kandasamy, Shigeo Matsuda, Alexander V. Kelin, Muthusamy Jayaraman, Kallanthottathil G. Rajeev
  • Patent number: 10808240
    Abstract: The invention provides novel methods and kits for fully automated high-throughput method for isolation of extracellular vesicles and co-isolation of cell-free DNA from biofluids, including cell-free DNA and/or cell-free DNA and nucleic acids including at least RNA from microvesicles, novel methods and kits for isolation of extracellular vesicles and co-isolation of cell-free DNA from biofluids, including cell-free DNA and/or cell-free DNA and nucleic acids including at least RNA from microvesicles that do not require the use of phenol or chloroform, and for extracting nucleic acids from the extracellular vesicles and/or from the biological samples.
    Type: Grant
    Filed: May 15, 2017
    Date of Patent: October 20, 2020
    Assignee: Exosome Diagnostics, Inc.
    Inventors: Georg Stoll, Daniel Enderle, Mikkel Noerholm, Johan Karl Olov Skog
  • Patent number: 10787659
    Abstract: The disclosure generally relates to compositions and methods for the extraction of nucleic acids from biological samples. In particular embodiments the extraction involves mixing dibromochloromethane, iodochloromethane or mixtures thereof with a biological sample that has been mixed with a phenol-based extraction solution. Centrifugation of the sample is not needed to achieve phase separation which occurs using the present methods in as little as one to two minutes with no phenol carryover.
    Type: Grant
    Filed: September 20, 2018
    Date of Patent: September 29, 2020
    Assignee: LIFE TECHNOLOGIES AS
    Inventors: Darren Ellis, Hannah Lindstroem
  • Patent number: 10774104
    Abstract: Disclosed is a method for the preparation of intermediates useful in the synthesis of gemcitabine-[phenyl-benzoxy-L-alaninyl)]-phosphate. Also disclosed is a method of preparing gemcitabine-[phenyl-benzoxy-L-alaninyl)]-phosphate.
    Type: Grant
    Filed: December 9, 2016
    Date of Patent: September 15, 2020
    Assignee: Laurus Labs Private Ltd
    Inventors: Mani Bushan Kotala, Venkata Lakshmi Narasimha Rao Dammalapati
  • Patent number: 10774105
    Abstract: Phosphoramidate esters and related nucleotide analogs useful in polynucleotide sequencing techniques, and synthetic methods for preparing those compounds, are disclosed, including compounds having the following structure: wherein R1, R2, R3 and R4 are as defined herein. These compounds include nucleotide phosphoramidates analogs that are modified on the alpha-phosphate to enable attachment of a variety of application-specific substituents such as tether molecules.
    Type: Grant
    Filed: April 10, 2019
    Date of Patent: September 15, 2020
    Assignee: STRATOS GENOMICS, INC.
    Inventors: Mark Stamatios Kokoris, John Tabone, Melud Nabavi, Aaron Jacobs
  • Patent number: 10766918
    Abstract: The present invention is directed to modified oligonucleotides having the following Formula (I) wherein one or more of phosphate groups are substituted at phosphorus, and methods for their synthesis. The modified oligonucleotides are useful for diagnostic applications involving sequence specific recognition of a nucleic acid and for use in a method of medical treatment.
    Type: Grant
    Filed: August 28, 2014
    Date of Patent: September 8, 2020
    Assignee: Noogen LLC
    Inventors: Dmitry Stetsenko, Maxim Kupryushkin, Dmitrii Pyshnyi
  • Patent number: 10752652
    Abstract: A method for preparing a ?-nucleoside compound, including the following steps: 1) performing a silylation reaction of a nitrogenous base or an analogue thereof in the presence of TMSOTf to give the nitrogenous base or the analogue thereof being protected by trimethylsilyl; 2) performing a direct glycosylation reaction of the reaction liquid, without being isolated, and a five- or six-membered ring saccharide or a derivative thereof closed by a hydroxyl protecting group to give a closed ?-nucleoside compound; and 3) performing a deprotection reaction to give the ?-nucleoside compound. The method uses a one-pot process to prepare the key intermediates of the ?-nucleoside compound, and the yield of materials in ?-configuration increases significantly. The method has the benefits of simple operations, being energy conservation and environment protection, and being suitable for industrial applications.
    Type: Grant
    Filed: December 21, 2017
    Date of Patent: August 25, 2020
    Assignee: JIANGSU AOSAIKANG PHARMACEUTICAL CO., LTD.
    Inventors: Zaiwei Zong, Qian Zhao, Ruifeng Yang, Gan Li, Chao Yi, Haixi Zhu