Patents by Inventor D. Tyler McQuade

D. Tyler McQuade 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).

  • Publication number: 20240109848
    Abstract: Described herein are methods for the preparation of imidazobenzodiazepines such as midazolam and its intermediates. The processes are capable of using continuous flow chemistry and systems.
    Type: Application
    Filed: September 13, 2023
    Publication date: April 4, 2024
    Applicant: ODH IP Corp.
    Inventors: D. Tyler McQuade, Luke Rogers, Josef Maier, Julian Chesterman, Esther Chen, Saad Bux, Brenden Herrera, Loan Truong, Melanie Pachter
  • Patent number: 9951020
    Abstract: A method of making a 2-halonicotinonitrile comprises reacting an alkylidene nitrile with a C1-compound in an organic solvent and a dehydrating agent. The dehydrating agent substantially retards dimerization of the alkylidene nitrile during the reaction. The enamine intermediate that forms from the reaction is cyclized using a halide donor to make the 2-halonicotinonitrile.
    Type: Grant
    Filed: February 19, 2016
    Date of Patent: April 24, 2018
    Assignees: Virginia Commonwealth University, The Florida State University Research Foundation, Incorporated
    Inventors: D. Tyler McQuade, Frank B. Gupton, Ashley R. Longstreet, Suzanne M. Opalka
  • Patent number: 8975269
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Grant
    Filed: July 29, 2014
    Date of Patent: March 10, 2015
    Assignee: Florida State University Research Foundation
    Inventors: D. Tyler McQuade, Jin Kyoon Park, Matthew D. Rexford, Hershel H. Lackey
  • Publication number: 20140336402
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Application
    Filed: July 29, 2014
    Publication date: November 13, 2014
    Inventors: D. TYLER MCQUADE, JIN KYOON PARK, MATTHEW D. REXFORD, HERSHEL H. LACKEY
  • Patent number: 8822483
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Grant
    Filed: May 22, 2012
    Date of Patent: September 2, 2014
    Assignee: Florida State University Research Foundation
    Inventors: D. Tyler McQuade, Jin Kyoon Park, Matthew D. Rexford, Hershel H. Lackey
  • Patent number: 8426630
    Abstract: A multi-step method for the continuous synthesis of ibuprofen or a synthetic precursor of ibuprofen is provided that does not require any intermediate purification or isolation steps and uses reagents compatible with downstream reactions. According to some embodiments, a method is provided wherein isobutylbenzene and a propionyl compound may be converted into a first product in a first Friedel Crafts acylation reaction. The first product may then be converted into a second product in a 1,2-aryl migration reaction. Finally, the second product may be converted into ibuprofen in a hydrolysis reaction. The present invention also provides a method wherein only the first and second reaction steps or only the second and third reaction steps are performed. An apparatus is also provided having two or more microreactors and two or more junctions in particular arrangements for the synthesis of ibuprofen or a synthetic precursor of ibuprofen.
    Type: Grant
    Filed: August 26, 2010
    Date of Patent: April 23, 2013
    Assignee: Florida State University Research Foundation
    Inventors: D. Tyler McQuade, Andrew Bogdan, Sarah Lihoa Poe
  • Publication number: 20120302434
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Application
    Filed: May 22, 2012
    Publication date: November 29, 2012
    Applicant: FLORIDA STATE UNIVERSITY RESEARCH FOUNDATION
    Inventors: D. TYLER MCQUADE, Jin Kyoon Park, Matthew D. Rexford, Hershel H. Lackey
  • Patent number: 8222265
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Grant
    Filed: August 30, 2010
    Date of Patent: July 17, 2012
    Assignee: Florida State University Research Foundation
    Inventors: D. Tyler McQuade, Jin Kyoon Park, Matthew D. Rexford, Hershel H. Lackey
  • Patent number: 8057861
    Abstract: A removable, colored X-alginate coating composition includes an aqueous solution of sodium alginate including a colorant and an aqueous solution containing divalent cations. The applied coating composition may be in the form of a thin film coating having a thickness of 10 nanometers or more and may include more than a single layer. The X-alginate coating composition is substantially removable from the application surface on-demand using a suitable chelator. A reversible, colored X-alginate coating system includes a colored X-alginate coating composition and a colored X-alginate coating composition remover. The remover may be a chelator. A method for reversibly coloring a surface includes applying an aqueous solution of sodium alginate including a colorant onto the surface and applying an aqueous solution containing divalent ions onto the surface. Water may subsequently be applied to the coated surface as a final washing step.
    Type: Grant
    Filed: September 16, 2008
    Date of Patent: November 15, 2011
    Assignee: Cornell University
    Inventors: D. Tyler McQuade, Muris Kobaslija
  • Publication number: 20110054170
    Abstract: The present invention provides a catalyst complex or ligand, and compositions thereof, for use in a variety of organic reactions having high reactivity and enantioselectivity. The catalyst is a N-heterocyclic carbene having three fused rings with first and second rings being six-membered rings and the third being a five-membered ring. The first ring is fused to the second and has four substituents. The second ring has two nitrogens flanking a carbene atom with one nitrogen bound to a substituent. The carbene atom may optionally be bonded to a metal. The third ring is fused to the second ring and contains two nitrogens. The third ring of the catalyst has a double bond and two substituents on adjacent non-fused carbons. A non-fused nitrogen of the third ring is partially bonded to another substituent. Methods for the synthesis and use of the catalyst embodiments of the present invention are also provided.
    Type: Application
    Filed: August 30, 2010
    Publication date: March 3, 2011
    Applicant: FLORIDA STATE UNIVERSITY RESEARCH FOUNDATION
    Inventors: D. Tyler McQuade, Jin Kyoon Park, Matthew D. Rexford, Hershel H. Lackey
  • Publication number: 20110054208
    Abstract: A multi-step method for the continuous synthesis of ibuprofen or a synthetic precursor of ibuprofen is provided that does not require any intermediate purification or isolation steps and uses reagents compatible with downstream reactions. According to some embodiments, a method is provided wherein isobutylbenzene and a propionyl compound may be converted into a first product in a first Friedel Crafts acylation reaction. The first product may then be converted into a second product in a 1,2-aryl migration reaction. Finally, the second product may be converted into ibuprofen in a hydrolysis reaction. The present invention also provides a method wherein only the first and second reaction steps or only the second and third reaction steps are performed. An apparatus is also provided having two or more microreactors and two or more junctions in particular arrangements for the synthesis of ibuprofen or a synthetic precursor of ibuprofen.
    Type: Application
    Filed: August 26, 2010
    Publication date: March 3, 2011
    Applicant: FLORIDA STATE UNIVERSITY RESEARCH FOUNDATION
    Inventors: D. Tyler McQuade, Andrew Bogdan, Sarah Lihoa Poe
  • Publication number: 20090273105
    Abstract: A microfluidic system for performing interfacial reactions can comprise at least one pump in fluid communication with a tube. A first fluid is injected into the tube so that its flow is laminar and continuous. A second fluid is injected in discrete amounts into the tube into the stream or flow of the first fluid. In other embodiments, discrete amounts of the second fluid are introduced into the channel first, then the first fluid is injected so that it creates a region of substantially laminar fluid flow around the discrete amounts of the second fluid. After the two fluids are in contact, a reaction occurs. The system can be configured so that the second fluid solidifies to form a capsule around the first fluid or vice versa. Other interfacial reactions also can be accomplished using the disclosed microfluidic systems and methods.
    Type: Application
    Filed: May 23, 2006
    Publication date: November 5, 2009
    Applicant: CORNELL RESEARCH FOUNDATION
    Inventors: D. Tyler McQuade, Jeremy L. Steinbacher, Elizabeth Quevedo
  • Publication number: 20090053497
    Abstract: A removable, colored X-alginate coating composition for a surface includes an aqueous solution of sodium alginate including a colorant and an aqueous solution containing divalent cations. In various aspects, the aqueous solution containing divalent cations includes, but is not limited to, calcium chloride, calcium chlorate, calcium carbonate, magnesium chloride, magnesium chlorate, or magnesium carbonate. The applied coating composition is advantageously in the form of a thin film coating. The thin film may have a thickness about equal to or greater than 10 nanometers and may include more than a single layer; for example, two mono-layers, but not limited as such. Any one of the plurality of monolayers may have a thickness about equal to or greater than five nanometers. Advantageously, the X-alginate coating composition according to the embodiments of the invention is substantially removable from the application surface on-demand upon the application of a suitable chelator.
    Type: Application
    Filed: September 16, 2008
    Publication date: February 26, 2009
    Applicant: Cornell University
    Inventors: D. Tyler McQuade, Muris Kobaslija
  • Patent number: 6172262
    Abstract: Disclosed are amphiphilic compounds comprising Formula I: wherein R1, R2, and R3 are C2-C12 straight or branched alkyl; unsubstituted phenyl, biphenyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl; or phenyl, biphenyl, C3-C8 cycloalkyl, or C3-C8 cycloalkenyl substituted with one, two, or three C1-C6 straight or branched alkyl groups; or R1 and R2 combined are C3-C8 cycloalkyl, C3-C8 cycloalkenyl; or C3-C8 cycloalkyl or C3-C8 cycloalkenyl substituted with one, two, or three C1-C6 straight or branched alkyl groups; one of R4 or R5 is selected from the group consisting of C2-C6-straight or branched alkyl-(dimethyl-N-oxide), alkyl-(dimethylamine), alkyl-(trimethylammonium), alkyl-glucosyl, alkyl-maltosyl, glucosyl, maltosyl, and polyethylene(glycosyl); the other of R4 or R5 is selected from the group consisting of H, C2-C6 straight or branched alkyl or alkenyl, C2-C6-straight or branched alkyl-(dimethyl-N-oxide); alkyl-(dimethylamine), alkyl-(trimethylammonium), alkyl-glucosyl, alkyl-maltosyl, glucos
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: January 9, 2001
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: D. Tyler McQuade, Samuel H. Gellman