Patents by Inventor Tomas Hudlicky

Tomas Hudlicky 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).

  • PROCESSES FOR THE PREPARATION OF HYDROXYLATED CYCLOHEXYL COMPOUNDS
    Publication number: 20170253550
    Abstract: The present application relates to processes for the preparation of polyhydroxylated cyclohexyl compounds such as the compounds of Formula I:
    Type: Application
    Filed: March 6, 2017
    Publication date: September 7, 2017
    Inventors: Tomás Hudlický, Jordan Thomas Froese
  • Methods and apparatus for time-pulsed chromatography
    Patent number: 9700813
    Abstract: The present disclosure relates to methods for the chromatographic separation of two or more sample components using a column while applying a time-pulsed pressure differential to the column and to apparatus for use in the same.
    Type: Grant
    Filed: May 5, 2014
    Date of Patent: July 11, 2017
    Inventors: Tomas Hudlicky, Ian David Brindle, Mary Ann Endoma-Arias
  • Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
    Patent number: 9533993
    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.
    Type: Grant
    Filed: July 30, 2015
    Date of Patent: January 3, 2017
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Ales Machara
  • Methods for the preparation of hydromorphone
    Patent number: 9475823
    Abstract: The present application relates to methods for the preparation of morphine derivatives. In particular, the present application relates to methods for the preparation of hydromorphone from oripavine and oripavine from thebaine.
    Type: Grant
    Filed: February 6, 2015
    Date of Patent: October 25, 2016
    Inventors: Tomas Hudlicky, Mary Ann Endoma-Arias, Brennan Augusta Murphy, Ivan Snajdr, Ales Machara
  • Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids
    Patent number: 9340550
    Abstract: The present invention provides a method for the N-demethylation and N-functionalization of an N-methylated heterocycle such as a morphine alkaloid or tropane alkaloid. The method comprises reacting the heterocycle with an functionalization agent in the presence of a transition metal catalyst in air or in the presence of an oxidant.
    Type: Grant
    Filed: January 30, 2015
    Date of Patent: May 17, 2016
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Robert James Carroll, Hannes Leisch, Ales Machara, Lukas Werner, Mary Ann Endoma-Arias
  • PROCESS FOR THE PREPARATION OF MORPHINE ANALOGS VIA METAL CATALYZED N-DEMETHYLATION/FUNCTIONALIZATION AND INTRAMOLECULAR GROUP TRANSFER
    Publication number: 20150336971
    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.
    Type: Application
    Filed: July 30, 2015
    Publication date: November 26, 2015
    Inventors: Tomas Hudlicky, Ales Machara
  • Process for preparing morphine compounds
    Patent number: 9126965
    Abstract: The present application relates to processes for the preparation of morphine compounds utilizing a novel intramolecular [4+2] cycloaddition reaction.
    Type: Grant
    Filed: February 23, 2015
    Date of Patent: September 8, 2015
    Assignee: Brock University
    Inventors: Vimal Varghese, Tomas Hudlicky
  • PROCESS FOR PREPARING MORPHINE COMPOUNDS
    Publication number: 20150239860
    Abstract: The present application relates to processes for the preparation of morphine compounds utilizing a novel intramolecular [4+2] cycloaddition reaction.
    Type: Application
    Filed: February 23, 2015
    Publication date: August 27, 2015
    Applicant: Brock University
    Inventors: Vimal Varghese, Tomas Hudlicky
  • Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
    Patent number: 9108967
    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.
    Type: Grant
    Filed: December 16, 2014
    Date of Patent: August 18, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Ales Machara
  • METHODS FOR THE PREPARATION OF HYDROMORPHONE
    Publication number: 20150225419
    Abstract: The present application relates to methods for the preparation of morphine derivatives. In particular, the present application relates to methods for the preparation of hydromorphone from oripavine and oripavine from thebaine.
    Type: Application
    Filed: February 6, 2015
    Publication date: August 13, 2015
    Inventors: Tomas HUDLICKY, Mary Ann ENDOMA-ARIAS, Brennan Augusta MURPHY, Ivan SNAJDR, Ales MACHARA
  • METHODS FOR ONE-POT N-DEMETHYLATION/N-FUNCTIONALIZATION OF MORPHINE AND TROPANE ALKALOIDS
    Publication number: 20150152120
    Abstract: The present invention provides a method for the N-demethylation and N-functionalization of an N-methylated heterocycle such as a morphine alkaloid or tropane alkaloid. The method comprises reacting the heterocycle with an functionalization agent in the presence of a transition metal catalyst in air or in the presence of an oxidant.
    Type: Application
    Filed: January 30, 2015
    Publication date: June 4, 2015
    Inventors: Tomas Hudlicky, Robert James Carroll, Hannes Leisch, Ales Machara, Lukas Werner, Mary Ann Endoma-Arias
  • Processes and intermediates in the preparation of morphine analogs via N-demethylation of N-oxides using cyclodehydration reagents
    Patent number: 9045497
    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: Grant
    Filed: January 7, 2015
    Date of Patent: June 2, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Lukas Werner, Ales Machara, Martina Wernerova, Mary Ann Endoma-Arias
  • PROCESSES AND INTERMEDIATES IN THE PREPARATION OF MORPHINE ANALOGS VIA N-DEMETHYLATION OF N-OXIDES USING CYCLODEHYDRATION REAGENTS
    Publication number: 20150133665
    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: January 7, 2015
    Publication date: May 14, 2015
    Inventors: Tomas Hudlicky, Lukas Werner, Ales Machara, Martina Wernerova, Mary Ann Endoma-Arias
  • PROCESS FOR THE PREPARATION OF MORPHINE ANALOGS VIA METAL CATALYZED N-DEMETHYLATION/FUNCTIONALIZATION AND INTRAMOLECULAR GROUP TRANSFER
    Publication number: 20150094471
    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.
    Type: Application
    Filed: December 16, 2014
    Publication date: April 2, 2015
    Inventors: Tomas Hudlicky, Ales Machara
  • Process for the preparation of morphine analogs via the reaction of organometallic reagents with an oxazolidine derived from morphinans
    Patent number: 8981098
    Abstract: The oxazolidine derived from the reaction of oxymorphone with the Burgess reagent, temporarily protected at O-3 and C-6, reacts with Grignard or other suitable metallic or organometallic reagents to directly provide, for example, A/-allyl, A/-methylcyclopropyl and /V-methylcyclobutyl derivatives that are further converted into naltrexone, naloxone, nalbuphone and nalbuphine in excellent yields. These morphine analogs can be prepared from the oxazolidine in a one-pot synthesis.
    Type: Grant
    Filed: January 30, 2013
    Date of Patent: March 17, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Mary Ann Endoma-Arias
  • Methods for one-pot -demethylation/-functionalization of morphine and tropane alkaloids
    Patent number: 8962841
    Abstract: The present invention provides a method for the N-demethylation and N-functionalization of an N-methylated heterocycle such as a morphine alkaloid or tropane alkaloid. The method comprises reacting the heterocycle with an functionalization agent in the presence of a transition metal catalyst in air or in the presence of an oxidant.
    Type: Grant
    Filed: July 8, 2011
    Date of Patent: February 24, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Robert James Carroll, Hannes Leisch, Ales Machara, Lukas Werner, Mary Ann Endoma-Arias
  • Processes and intermediates in the preparation of morphine analogs via N-demethylation of N-oxides using cyclodehydration reagents
    Patent number: 8957072
    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: Grant
    Filed: May 2, 2012
    Date of Patent: February 17, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Lukas Werner, Ales Machara, Martina Wernerova, Mary Ann Endoma-Arias
  • Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
    Patent number: 8946214
    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.
    Type: Grant
    Filed: May 4, 2012
    Date of Patent: February 3, 2015
    Assignee: Brock University
    Inventors: Tomas Hudlicky, Ales Machara
  • PROCESS FOR THE PREPARATION OF MORPHINE ANALOGS VIA THE REACTION OF ORGANOMETALLIC REAGENTS WITH AN OXAZOLIDINE DERIVED FROM MORPHINANS
    Publication number: 20140371458
    Abstract: The oxazolidine derived from the reaction of oxymorphone with the Burgess reagent, temporarily protected at 0-3 and C-6, reacts with Grignard or other suitable metallic or organometallic reagents to directly provide, for example, A/-allyl, A/-methylcyclopropyl and /V-methylcyclobutyl derivatives that are further converted into naltrexone, naloxone, nalbuphone and nalbuphine in excellent yields. These morphine analogs can be prepared from the oxazolidine in a one-pot synthesis.
    Type: Application
    Filed: January 30, 2013
    Publication date: December 18, 2014
    Applicant: Brock University
    Inventors: Tomas HUDLICKY, Mary Ann ENDOMA-ARIAS
  • METHODS AND APPARATUS FOR TIME-PULSED CHROMATOGRAPHY
    Publication number: 20140326670
    Abstract: The present disclosure relates to methods for the chromatographic separation of two or more sample components using a column while applying a time-pulsed pressure differential to the column and to apparatus for use in the same.
    Type: Application
    Filed: May 5, 2014
    Publication date: November 6, 2014
    Applicant: BROCK UNVIVERSITY
    Inventors: Tomas Hudlicky, Ian David Brindle, Mary Ann Endoma-Arias