Abstract: The present application described a method of reducing methoxypyrazines (MPs) in grapes or grape products comprising: (a) contacting the grape or grape product with a protein that binds to MPs at a pH of about 3 to about 4 to form a protein-MP complex; and (b) removing the protein-MP complex from the grape or grape product. Also described is a method of removing MPs from samples comprising contacting the sample with a polyethersulfone membrane.
Type:
Grant
Filed:
April 14, 2010
Date of Patent:
October 14, 2014
Assignee:
Brock University
Inventors:
Debra Inglis, Ai Lin Beh, Ian David Brindle, Gary Pickering, Eric Fabian Humes
Abstract: The present application describes processes for the synthesis of morphinane and morphinone compounds, useful as pharmaceutical agents. Also included are novel intermediates useful in the preparation of these compounds. The process comprises quaternization of oripavine to provide a mixture of the R- and S-isomeric (at the nitrogen) quaternary salts. The R-isomer is readily isolated and converted to various N-(R)-morphinane and N-(S)-morphinone compounds. The R-isomer, S-isomer or a mixture of R- and S-isomers may be demethylated and converted to various morphinane and morphinone compounds.
Type:
Grant
Filed:
April 22, 2010
Date of Patent:
October 7, 2014
Assignee:
Brock University
Inventors:
Tomas Hudlicky, Robert Carroll, Hannes Leisch, Ales Machara, Lukas Werner, David R. Adams
Abstract: The present application relates to processes for the preparation of intermediates useful in the manufacture of oseltamivir and the H3PO4 salt of oseltamivir, TamifluĀ®. The application further relates to novel intermediate and compounds and oseltamivir analogs and to pharmaceutical compositions comprising said analog compounds. The application further relates to a method of using the novel analogs of oseltamivir to treat or prevent influenza.
Type:
Grant
Filed:
October 15, 2010
Date of Patent:
May 6, 2014
Assignee:
Brock University
Inventors:
Tomas Hudlicky, Lukas Werner, Ales Machara
Abstract: The present application relates to novel C-1 substituted analogues of pancratistatin and 7-dexoypancratistatin of Formula (I), pharmaceutical compositions thereof and the use of said compounds of Formula (I) in the treatment of cancer The application also relates to processes for the preparation of said compound of Formula (I) and intermediates thereof.
Abstract: The present application is directed to compounds of Formula I: wherein R1-R9, X, Y and Z are as defined in the application, and to the use of the compounds of Formula I, for example, for the fluorescent labeling of oligonucleotides.
Abstract: Disclosure herein are methods of preparing cross-linked silicone polymers by contacting a silicone polymer and optionally a cross-linking agent with a hydrolytic enzyme under conditions for the cross-linking of the silicone polymer, wherein the silicone polymer has been modified to comprise functional groups that react with the hydrolytic enzyme.
Type:
Grant
Filed:
June 19, 2008
Date of Patent:
February 26, 2013
Assignee:
Brock University
Inventors:
Paul M. Zelisko, Karen Arnelien, Mark Frampton
Abstract: The present application is directed to an efficient conversion of C-14 hydroxylated morphine alkaloids to various morphine analogs, such as naltrexone, naloxone and nalbuphone. One feature of this process is an intramolecular functional group transfer from the C-14 hydroxyl to the N-17 nitrogen atom following a palladium-catalyzed N-demethylation.
Abstract: A high-yielding method for the N-demethylation of oxycodone- and oxymorphone-N-oxides by the reaction of these compounds with cyclodehydration reagents has been performed. This method has been utilized to improve the synthesis of various morphine analogs, such as naltrexone, nalbuphone and naloxone.
Type:
Application
Filed:
May 2, 2012
Publication date:
November 8, 2012
Applicant:
Brock University
Inventors:
Tomas Hudlicky, Lukas Werner, Ales Machara, Martina Wernerova, Mary Ann Endoma-Arias
Abstract: The present application relates to processes for the preparation of intermediates useful in the manufacture of oseltamivir and the H3PO4 salt of oseltamivir, TamifluĀ®. The application further relates to novel intermediate and compounds and oseltamivir analogs and to pharmaceutical compositions comprising said analog compounds. The application further relates to a method of using the novel analogs of oseltamivir to treat or prevent influenza.
Type:
Application
Filed:
October 15, 2010
Publication date:
October 4, 2012
Applicant:
BROCK UNIVERSITY
Inventors:
Tomas Hudlicky, Lukas Werner, Ales Machara
Abstract: The present application described a method of reducing methoxypyrazines (MPs) in grapes or grape products comprising: (a) contacting the grape or grape product with a protein that binds to MPs at a pH of about 3 to about 4 to form a protein-MP complex; and (b) removing the protein-MP complex from the grape or grape product. Also described is a method of removing MPs from samples comprising contacting the sample with a polyethersulfone membrane.
Type:
Application
Filed:
April 14, 2010
Publication date:
May 3, 2012
Applicant:
BROCK UNIVERSITY
Inventors:
Debra Inglis, Ai Lin Beh, Ian David Brindle, Gary Pickering, Eric Fabian Humes
Abstract: The present application is directed to compounds of Formula I: wherein R1-R9, X, Y and Z are as defined in the application, and to the use of the compounds of Formula I, for example, for the fluorescent labeling of oligonucleotides.
Abstract: The present application relates to novel C-1 substituted analogues of pancratistatin and 7-dexoypancratistatin of Formula (I), pharmaceutical compositions thereof and the use of said compounds of Formula (I) in the treatment of cancer The application also relates to processes for the preparation of said compound of Formula (I) and intermediates thereof.
Abstract: The present application relates to processes for the preparation of oseltamivir and the H3PO4 salt of oseltamivir, TamifluĀ®. The application further relates to novel intermediate compounds and to pharmaceutical compositions containing said compounds. The application further relates to a method of using the novel intermediates to treat or prevent influenza.
Abstract: The present invention provides a method for the N-demethylation and/or N-acylation of an N-methylated heterocycle such as morphine alkaloids or tropane alkaloids. The method comprises reacting the heterocycle with an acylating agent in the presence of a metal catalyst.
Type:
Grant
Filed:
June 29, 2007
Date of Patent:
August 16, 2011
Assignee:
Brock University
Inventors:
Robert James Carroll, Hannes Leisch, Tomas Hudlicky, D. Phillip Cox
Abstract: The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.
Abstract: The present invention provides a method for the N-demethylation of an N-methylated heterocycle, particularly a morphine or tropane alkaloid or derivative thereof. The method comprises reacting the heterocycle with a metal catalyst and a solvent in the presence of an oxidizing agent.
Type:
Grant
Filed:
June 29, 2007
Date of Patent:
May 3, 2011
Assignee:
Brock University
Inventors:
Robert James Carroll, Hannes Leisch, Tomas Hudlicky
Abstract: The present invention provides methods for the conversion of thebaine to a morphine derivative, such as hydrocodone. Novel ketal intermediates of the conversion are provided. A one-pot procedure for the conversion comprises treating thebaine with an acid in the presence of a metal catalyst.
Type:
Grant
Filed:
June 29, 2007
Date of Patent:
April 19, 2011
Assignee:
Brock University
Inventors:
Robert James Carroll, Hannes Leisch, Tomas Hudlicky
Abstract: Disclosure herein are methods of preparing cross-linked silicone polymers by contacting a silicone polymer and optionally a cross-linking agent with a hydrolytic enzyme under conditions for the cross-linking of the silicone polymer, wherein the silicone polymer has been modified to comprise functional groups that react with the hydrolytic enzyme.
Type:
Application
Filed:
June 19, 2008
Publication date:
November 11, 2010
Applicant:
BROCK UNIVERSITY
Inventors:
Paul M. Zelisko, Karen Arnelien, Mark Frampton
Abstract: Tocopherol derivatives having the general formula: wherein n is an integer of 6 to 13, R1 is hydrogen, a silyl ether or acetate, R2 is an optionally substituted nitrogen-containing heterocycle or a polycyclic nitrogen-containing heterocycle; and pharmaceutically acceptable salts thereof are provided. A method for synthesizing the compounds is also provided. The tocopherol derivatives are capable of inhibiting the primary enzyme responsible for the metabolism of the tocopherols and tocotrienols compounds of vitamin E, namely tocopherol-?-hydroxylase, and thus increase the amount and prolong the availability of these compounds in plasma and tissue.
Type:
Grant
Filed:
May 25, 2007
Date of Patent:
June 8, 2010
Assignees:
Brock University, Cornell University
Inventors:
Jeffrey Atkinson, Robert S. Parker, Stephan Ohnmacht, Phillip John Nava, Ryan West
Abstract: The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.