Patents Assigned to TSRL, Inc.
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Publication number: 20210401992Abstract: Provided are prodrugs of various therapeutic agents that provide enhanced bioavailability of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is —S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is —H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, —C(CH3)3, —CF3, —C(CF3)3, or a substituted or unsubstituted phenyl.Type: ApplicationFiled: June 26, 2019Publication date: December 30, 2021Applicants: TSRL, Inc., Regents of the University of MichiganInventors: Elke D. Lipka, Eric Simon, Andy D. White, Kim M. Hutchings, Xinmin Gan
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Patent number: 8535716Abstract: A pharmaceutical composition is provided that includes an active ingredient in the form of a powder or granule, a water soluble high molecular weight excipient and a water insoluble hydrophilic amphiphilic excipient. These ingredients are solution mixed and dried to form a modified pharmaceutical ingredient in simultaneous contact with both the water soluble high molecular weight excipient and the water insoluble hydrophilic amphiphilic excipient. Adjuvants are compacted about the modified pharmaceutical ingredient as well as a release control agent. The release control agent being present at levels from 1 to 40 total weight percent of the pharmaceutical composition.Type: GrantFiled: April 1, 2005Date of Patent: September 17, 2013Assignee: TSRL, Inc.Inventors: John Hilfinger, Jae Seung Kim, Paul Kijek
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Publication number: 20130023585Abstract: Disclosed are neuraminidase inhibitor compounds and pharmaceutical compositions with improved bioavailability and/or improved efficacy and methods of treating influenza using the compounds and pharmaceuticals compositions.Type: ApplicationFiled: April 4, 2011Publication date: January 24, 2013Applicant: TSRL, INC.Inventors: John Hilfinger, Wei Shen
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Publication number: 20120058937Abstract: A new class of neuramidase inhibitor prodrugs is provided characterized by a prodrug moiety of a carboxyl group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide or a carbonyl ethoxy tripeptide, a guanidine group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide, a carbonyl ethoxy tripeptide; a primary alcohol modified to form an esterified single amino acid, dipeptide or tripeptide of zanavimir of the unaltered therapeutic agent. Exemplary therapeutic agents so modified to form prodrugs include zanavimir, oseltamivir and peramivir. The prodrug has increased oral bioavailability relative to the unaltered neuraminidase inhibitor and is effective in the inhibition of viral infections involving neuraminidase in the viral reproductive cycle.Type: ApplicationFiled: April 15, 2009Publication date: March 8, 2012Applicant: TSRL, Inc.Inventors: John Hilfinger, Gordon Amidon
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Patent number: 8063209Abstract: Cidofovir or foscarnet based compounds having an amino acid or dipeptide esters are provided as prodrugs.Type: GrantFiled: March 16, 2009Date of Patent: November 22, 2011Assignees: TSRL, Inc., National Institute of Health (NIH), The United States of America as represented by the Department of Health and Human Services (DHHS), The United States of America as represented by the NIH Division of Extramural Inventions and Technology Resources (DEITR)Inventors: John Hilfinger, Charles E. McKenna, Boris A. Kashemirov, Chi Pham, Kanokkarn Saejueng, Larryn Peterson
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Publication number: 20110160127Abstract: A new class of neuramidase inhibitor prodrugs is provided characterized by a prodrug moiety of a carboxyl group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide or a carbonyl ethoxy tripeptide, a guanidine group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide, a carbonyl ethoxy tripeptide; a primary alcohol modified to form an esterified single amino acid, dipeptide or tripeptide of zanavimir of the unaltered therapeutic agent. Exemplary therapeutic agents so modified to form prodrugs include zanavimir, oseltamivir and peramivir. The prodrug has increased oral bioavailability relative to the unaltered neuraminidase inhibitor and is effective in the inhibition of viral infections involving neuraminidase in the viral reproductive cycle.Type: ApplicationFiled: April 15, 2009Publication date: June 30, 2011Applicant: TSRL, Inc.Inventors: John Hilfinger, Gordon Amidon
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Patent number: 7511051Abstract: Cidofovir-based compounds having an amino acid, dipeptide or tripeptide attached to a cidofovir or cyclic cidofovir framework. The compounds show enhanced oral bioavailability and increased binding to the PepT1 transporter. The present invention also provides compositions and methods for treating virus infections, and a method of preparing cidofovir.Type: GrantFiled: July 1, 2005Date of Patent: March 31, 2009Assignees: University of Southern California, TSRL, Inc.Inventors: Charles E. McKenna, Boris A. Kashemirov, Ulrika Tehler, John Hilfinger
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Patent number: 7176185Abstract: A dipeptide or tripeptide carrier system for active agent delivery to cells has an N-terminus natural amino acid and an active agent covalently bonded to a side chain of one of the remaining amino acid bases. The system is amenable to formulation as an oral administrant. The active agent being a therapeutic, a fluorescent dye, or contrast agent where the active agent has a molecular weight of less than 500 atomic mass units. An optional linker is provided intermediate between the active agent and the linking side chain.Type: GrantFiled: November 24, 2004Date of Patent: February 13, 2007Assignee: TSRL, Inc.Inventors: John Hilfinger, Phillip Kish
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Publication number: 20050220876Abstract: A pharmaceutical composition is provided that includes an active ingredient in the form of a powder or granule, a water soluble high molecular weight excipient and a water insoluble hydrophilic amphiphilic excipient. These ingredients are solution mixed and dried to form a modified pharmaceutical ingredient in simultaneous contact with both the water soluble high molecular weight excipient and the water insoluble hydrophilic amphiphilic excipient. Adjuvants are compacted about the modified pharmaceutical ingredient as well as a release control agent. The release control agent being present at levels from 1 to 40 total weight percent of the pharmaceutical composition.Type: ApplicationFiled: April 1, 2005Publication date: October 6, 2005Applicant: TSRL, Inc.Inventors: John Hilfinger, Jae Kim, Paul Kijek
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Patent number: 5569452Abstract: A pharmaceutical formulation comprising a polymeric resin having bile acid binding properties in combination with at least one bile acid binding material which enhances the bile acid binding affinity and/or capacity of the formulation, methods for preparing the formulations and methods for using the formulations.Type: GrantFiled: May 30, 1995Date of Patent: October 29, 1996Assignee: TSRL, Inc.Inventors: Gordon L. Amidon, Lizbeth B. Sherman, John R. Crison
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Patent number: 5387421Abstract: A drug delivery system includes a first capsule half having an inner chamber for containing a drug therein. A plug is disposed in a passageway of the capsule half for plugging the opening thereof. The plug is releasable from the passageway opening upon the application of pressure from within the inner chamber. A pump mechanism causes an increase in pressure within the inner chamber and forces the plug out of the passageway to release the drug from the inner chamber and out of the passageway thereby providing a second pulse of drug release at a predetermined time after initial ingestion of the capsule. The invention further provides a method of manufacturing the drug delivery system and method by which the drug delivery system provides the drug to the body.Type: GrantFiled: May 31, 1994Date of Patent: February 7, 1995Assignee: TSRL, Inc.Inventors: Gordon L. Amidon, Glen D. Leesman, Lizbeth B. Sherman