Patents by Inventor Charles E. McKenna
Charles E. McKenna 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).
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Patent number: 11840549Abstract: Described herein are bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof.Type: GrantFiled: December 11, 2020Date of Patent: December 12, 2023Assignees: BIOVINC, LLC, UNIVERSITY OF SOUTHERN CALIFORNIAInventors: Frank H. Ebetino, Shuting Sun, Mark W. Lundy, Charles E. McKenna, Eric Richard, Parish Sedghizadeh, Keivan Sadrerafi, Philip T. Cherian
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Publication number: 20230322823Abstract: Various nucleoside phosphate and phosphonate analogues are provided for treatment of viral infections. Methods of preparing the analogues, pharmaceutical compositions containing the analogues, and methods of using the analogues as antiviral compounds, especially against adenoviruses, coronaviruses, and varicella zoster viruses, are also provided.Type: ApplicationFiled: August 18, 2021Publication date: October 12, 2023Applicant: UNIVERSITY OF SOUTHERN CALIFORNIAInventor: Charles E. MCKENNA
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Publication number: 20230133119Abstract: Herein is reported a class of chiral compounds with paradoxical effects on the androgen receptor (AR). The (R)-enantiomers behave like classical anti-androgens while the (S)-enantiomers activate AR signaling. In castration-resistant prostate cancer, the change during the course of therapy to growth in the presence of AR targeted therapeutics, a harbinger of progression to lethal disease, is commonly attributed to acquired mutations of the AR-ligand binding domain. This is the first report of an antagonist—agonist duality solely due to structural enantiomerism, without any modification to the AR binding site.Type: ApplicationFiled: March 22, 2021Publication date: May 4, 2023Applicant: University of Southern CaliforniaInventors: Charles E. McKenna, David B. Agus
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Publication number: 20220249673Abstract: This invention relates to drug conjugates useful for localized treatment of diseases or disorders of the middle ear and/or inner ear. Methods of treating diseases or disorders of the middle ear and/or inner ear, pharmaceutical compositions comprising the conjugates, and methods of inhibiting a Tropomyosin receptor kinase are also provided.Type: ApplicationFiled: April 12, 2022Publication date: August 11, 2022Inventors: Charles E. McKenna, Boris A. Kashemirov, Shuting Sun, Kim Nguyen, David Jung, Michael J. McKenna, William Sewell, Judith Kempfle, Woo Seok Kang, Albert Edge
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Patent number: 11331391Abstract: This invention relates to drug conjugates useful for localized treatment of diseases or disorders of the middle ear and/or inner ear. Methods of treating diseases or disorders of the middle ear and/or inner ear, pharmaceutical compositions comprising the conjugates, and methods of inhibiting a Tropomyosin receptor kinase are also provided.Type: GrantFiled: January 25, 2017Date of Patent: May 17, 2022Assignees: Massachusetts Eye and Ear Infirmary, University of Southern CaliforniaInventors: Charles E. McKenna, Boris A. Kashemirov, Shuting Sun, Kim Nguyen, David Jung, Michael J. McKenna, William Sewell, Judith Kempfle, Woo Seok Kang, Albert Edge
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Patent number: 11219697Abstract: In certain embodiments osteoadsorptive fluorogenic substrates of cathepsin K (or other proteases) are provided. Utilizing a bisphosphonate targeting moiety, the fluorogenic substrates provide effective bone-targeted protease sensor(s). In certain embodiments the “probes” comprise cleavable fluorophore-quencher pair linked by a cathepsin K (or other protease) peptide substrate and tethered to a bisphosphonate. Unlike existing probes that are cleared within a few days in vivo, the probes described herein (e.g., OFS-1) allow for monitoring resorption over the course of longer time periods with a single dose.Type: GrantFiled: July 13, 2018Date of Patent: January 11, 2022Assignees: The Regents of the University of California, University of Southern CaliforniaInventors: Ichiro Nishimura, Akishige Hokugo, Kenzo Morinaga, Charles E. McKenna, Boris A Kashemirov, Eric T. Richard
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Publication number: 20210369849Abstract: Described herein are bisphosphonate oxazolidinone compounds, and conjugates and pharmaceutical formulations thereof, that can include a bisphosphonate and an oxazolidinone (or an oxazolidinone antimicrobial or antibiotic agent, substituent or derivative thereof), where the oxazolidinone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate oxazolidinone compounds, conjugates and pharmaceutical formulations thereof. Also provided herein are methods of use of the compounds, conjugates and formulations for treating a bone disease or for use in preparing a formulation for the treatment a bone disease.Type: ApplicationFiled: June 25, 2019Publication date: December 2, 2021Inventors: Frank Hallock EBETINO, Shuting SUN, Charles E. MCKENNA, Keivan SADRERAFI, Philip CHERIAN
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Publication number: 20210101920Abstract: Described herein are bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof.Type: ApplicationFiled: December 11, 2020Publication date: April 8, 2021Inventors: Frank H. EBETINO, Shuting SUN, Mark W. LUNDY, Charles E. MCKENNA, Eric RICHARD, Parish SEDGHIZADEH, Keivan SADRERAFI, Philip T. CHERIAN
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Patent number: 10918647Abstract: The invention provides antifungal compounds, antifungal compositions, and intermediates for the preparation of antifungal compounds and antifungal compositions. The invention also provides methods of inhibiting fungi and methods of treating fungal infections, for example, with a compound or composition described herein. The antifungal compositions can include antifungal adjuvants such as essential oils or essential oil extracts, which adjuvants further improve the antifungal activity of the compositions.Type: GrantFiled: July 26, 2017Date of Patent: February 16, 2021Assignees: University of Southern California, CNRS, Universite Grenoble Alpes, INSERMInventors: Charles E. McKenna, Carlo Petosa, Jerome Govin, Boris A. Kashemirov, Elena Ferri, Flore Mietton
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Patent number: 10919922Abstract: Antiviral compounds comprising prodrugs with differing side chains derived from a tyrosine substance in the form of a tyrosine amide in which the amide substituent side chain is an alkyl ether, thioether, or alkene. Embodiments of the compounds have a range of effective lipophilicity values allowing variation in aqueous solubility, oral bioavailability, cell permeability and in vivo activation properties. The embodiments have promoieties derived from a single amino acid, which are expected to have low toxicity. The features described above also make possible a novel “precision medicine” approach to treatment of viral infections, whereby the prodrug variations can be exploited to match optimal activation of the prodrug to a given patient or strain of virus.Type: GrantFiled: October 31, 2017Date of Patent: February 16, 2021Assignee: University of Southern CaliforniaInventors: Charles E. McKenna, Boris A. Kashemirov, Jaijun Fan, Jinglei Lyu
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Patent number: 10865220Abstract: Described herein are bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof.Type: GrantFiled: December 3, 2018Date of Patent: December 15, 2020Assignees: BIOVINC, LLC, UNIVERSITY OF SOUTHERN CALIFORNIAInventors: Frank H. Ebetino, Shuting Sun, Mark W. Lundy, Charles E. McKenna, Eric Richard, Parish Sedghizadeh, Keivan Sadrerafi, Philip T. Cherian
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Publication number: 20200215205Abstract: In certain embodiments osteoadsorptive fluorogenic substrates of cathepsin K (or other proteases) are provided. Utilizing a bisphosphonate targeting moiety, the fluorogenic substrates provide effective bone-targeted protease sensor(s). In certain embodiments the “probes” comprise cleavable fluorophore-quencher pair linked by a cathepsin K (or other protease) peptide substrate and tethered to a bisphosphonate. Unlike existing probes that are cleared within a few days in vivo, the probes described herein (e.g., OFS-1) allow for monitoring resorption over the course of longer time periods with a single dose.Type: ApplicationFiled: July 13, 2018Publication date: July 9, 2020Applicants: The Regents of the University of California, UNIVERSITY OF SOUTHERN CALIFORNIAInventors: Ichiro Nishimura, Akishige Hokugo, Kenzo Morinaga, Charles E. McKenna, Boris A Kashemirov, Eric T. Richard
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Publication number: 20200206370Abstract: A novel method for rapidly and efficiently introducing fluorine into the P-C-P backbone of bisphosphonates starting from readily accessible diazomethylenebisphosphonate esters is provided. The method is applied successfully to create novel [18F]-labeled bisphosphonates for positron emission tomography imaging. Some versions of the method include reacting a diazomethylenebisphosphonate tetraalkyl ester with a fluorinating agent in the presence of an acidic HF/base complex and a t-butyl hypohalite to produce a halofluoromethylenebisphosphonate tetraalkyl ester, and dealkylating the halofluoromethylenebisphosphonate alkyl ester to produce a halofluoromethylenebis(phosphonic acid). Methods of replacing the halogen group with hydrogen are further provided. 18F-labeled bisphosphonates prepared by the methods, and methods of using such compounds for positron emission tomography imaging in patients and animal models, are also provided.Type: ApplicationFiled: March 7, 2017Publication date: July 2, 2020Inventors: Charles E. McKenna, Boris A Kashemirov, Amirsoheil Negahbani, Kai Chen
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Publication number: 20190270762Abstract: An antiviral compound of the following formula (I) is provided or a salt or a pharmaceutically acceptable salt thereof, where B is a naturally occurring or non-naturally occurring base; R1 is a C2-C14 alkyl group; X is O, S, CH?CH (cis) or CH?CH (trans); and R2 is a C2-C14 alkyl group. In some embodiments, B can be adenine or cytosine. Compositions containing the compound, and methods of using and preparing the compound, are also provided.Type: ApplicationFiled: October 31, 2017Publication date: September 5, 2019Applicant: University of Southern CaliforniaInventors: Charles E. McKenna, Boris A. Kashemirov, Jaijun Fan, Jinglei Lyu
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Publication number: 20190240232Abstract: The invention provides antifungal compounds, antifungal compositions, and intermediates for the preparation of antifungal compounds and antifungal compositions. The invention also provides methods of inhibiting fungi and methods of treating fungal infections, for example, with a compound or composition described herein. The antifungal compositions can include antifungal adjuvants such as essential oils or essential oil extracts, which adjuvants further improve the antifungal activity of the compositions.Type: ApplicationFiled: July 26, 2017Publication date: August 8, 2019Applicants: University of Southern California, CNRS, Universite Grenoble Alpes, INSERMInventors: Charles E. MCKENNA, Carlo PETOSA, Jerome GOVIN, Boris A. KASHEMIROV, Elena FERRI, Flore MIETTON
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Publication number: 20190169214Abstract: Described herein are bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof that can include a bisphosphonate and a quinolone, where the quinolone can be releasably coupled to the bisphosphonate. Also provided herein are methods of making and methods of using the bisphosphonate quinolone compounds, conjugates and pharmaceutical formulations thereof.Type: ApplicationFiled: December 3, 2018Publication date: June 6, 2019Inventors: Frank H. EBETINO, Shuting SUN, Mark W. LUNDY, Charles E. MCKENNA, Eric RICHARD, Parish SEDGHIZADEH, Keivan SADRERAFI, Philip T. CHERIAN
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Publication number: 20190030172Abstract: This invention relates to drug conjugates useful for localized treatment of diseases or disorders of the middle ear and/or inner ear. Methods of treating diseases or disorders of the middle ear and/or inner ear, pharmaceutical compositions comprising the conjugates, and methods of inhibiting a Tropomyosin receptor kinase are also provided.Type: ApplicationFiled: January 25, 2017Publication date: January 31, 2019Inventors: Charles E. McKenna, Boris A. Kashemirov, Shuting Sun, Kim Nguyen, David Jung, Michael J. McKenna, William Sewell, Judith Kempfle, Woo Seok Kang, Albert Edge
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Publication number: 20180362559Abstract: A compound of Formula I has the structure: wherein G is a straight, branched or cyclic alkyl group having 2 to 50 carbon atoms or an ether group, and R is a fluorescent dye. In some embodiments, G is selected from the group consisting of —(CH2)n— and —(CH2OCH2)m—, wherein n is an integer from 2 to 18, m is an integer from 2 to 18.Type: ApplicationFiled: September 21, 2016Publication date: December 20, 2018Applicant: University of Southern CaliforniaInventors: Charles E. MCKENNA, Boris A. KASHEMIROV, Kim NGUYEN
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Publication number: 20180064829Abstract: Fluorescent probes based on N-heterocyclic bisphosphonates or their phosphonocarboxylate analogues are provided. The probes have variable spectroscopic properties, bone mineral binding affinities, and pharmacological activities. Methods for preparing the probes include the use of two complementary linking strategies, one involving an amino group and the other involving a chloride group as a precursor to an amino group. In other versions, bifunctional N-heterocyclic bisphosphonates are provided having an amino group and an azido group as linking moieties. In some versions, the linking chemistry allows attachment of a wide selection of fluorescent dyes in the visible to near-infrared range to any of three clinically important heterocyclic bisphosphonates.Type: ApplicationFiled: April 2, 2016Publication date: March 8, 2018Applicant: University of Southern CaliforniaInventors: Charles E. McKenna, Boris A. Kashemirov, Shuting Sun, Feng Ni
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Patent number: 9550803Abstract: An amino acid conjugate of a cyclic or acyclic nucleoside phosphonate is provided. In some cases, the amino acid conjugate is a tyrosine alkyl amide phosphonate ester conjugate of a cyclic or acyclic nucleoside phosphonate, and is useful as an antiviral compound. In certain cases, the tyrosine conjugate includes a long chain alkyl group on the carboxamide group of the tyrosine residue. In a method of preparing an acyclic tyrosine conjugate, a tert-butyloxycarbonyl (Boc) protected tyrosine residue containing a long chain alkyl group is reacted with an acyclic nucleoside phosphonate mono-ethyl ester in the presence of benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate to produce a Boc-protected nucleoside phosphonate di-ester, and the di-ester is deethylated and deprotected to produce the tyrosine conjugate. Methods of inhibiting viral replication and methods of treating a viral infection using the amino acid conjugate are also provided.Type: GrantFiled: May 7, 2012Date of Patent: January 24, 2017Assignee: University of Southern CaliforniaInventors: Charles E. McKenna, Boris A Kashemirov, Ivan S Krylov, Valeria M. Zakharova