Patents by Inventor Raymond McCague

Raymond McCague 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).

  • Patent number: 11690396
    Abstract: Disclosed herein is an inhalable composition, suitable for use in an electronic cigarette device, comprising at least 1 g/L of nicotine and at least 2 g/L of carbon dioxide dissolved or dispersed in a solvent comprising glycerol and water, wherein the molar ratio of carbon dioxide to nicotine is at least 0.1:1; wherein glycerol is present in an amount of at least 40% by weight, based on the total weight of the inhalable composition; wherein water is present in an amount of 1-20% by weight, based on the total weight of the inhalable composition; and wherein propylene glycol, when present, is present in an amount of no more than 10% by weight, based on the total weight of the inhalable composition.
    Type: Grant
    Filed: March 25, 2021
    Date of Patent: July 4, 2023
    Assignee: Zanoprima Lifesciences Limited
    Inventors: Ashok S. Narasimhan, Raymond McCague, Nicholas Hyde, William Jackson
  • Patent number: 11684080
    Abstract: Disclosed herein is an inhalable composition, suitable for use in an electronic cigarette device, comprising at least 1 g/L of nicotine and carbon dioxide dissolved or dispersed in a solvent.
    Type: Grant
    Filed: October 23, 2019
    Date of Patent: June 27, 2023
    Assignee: Zanoprima Lifesciences Limited
    Inventors: Ashok S. Narasimhan, Raymond McCague, Nicholas Hyde, William Jackson
  • Publication number: 20210315261
    Abstract: Disclosed herein is an inhalable composition, suitable for use in an electronic cigarette device, comprising at least 1 g/L of nicotine and carbon dioxide dissolved or dispersed in a solvent.
    Type: Application
    Filed: October 23, 2019
    Publication date: October 14, 2021
    Inventors: Ashok S. NARASIMHAN, Raymond MCCAGUE, Nicholas HYDE, William JACKSON
  • Publication number: 20210204589
    Abstract: Disclosed herein is an inhalable composition, suitable for use in an electronic cigarette device, comprising at least 1 g/L of nicotine and at least 2 g/L of carbon dioxide dissolved or dispersed in a solvent comprising glycerol and water, wherein the molar ratio of carbon dioxide to nicotine is at least 0.1:1; wherein glycerol is present in an amount of at least 40% by weight, based on the total weight of the inhalable composition; wherein water is present in an amount of 1-20% by weight, based on the total weight of the inhalable composition; and wherein propylene glycol, when present, is present in an amount of no more than 10% by weight, based on the total weight of the inhalable composition.
    Type: Application
    Filed: March 25, 2021
    Publication date: July 8, 2021
    Inventors: Ashok S. NARASIMHAN, Raymond MCCAGUE, Nicholas HYDE, William JACKSON
  • Patent number: 10913962
    Abstract: A process for synthetically producing (S)-nicotine ([(S)-3-(1-methylpyrrolidin-2-yl) pyridine]) is provided.
    Type: Grant
    Filed: March 12, 2019
    Date of Patent: February 9, 2021
    Assignee: ZANOPRIMA LIFESCIENCES LIMITED
    Inventors: Raymond McCague, Ashok Srinivasan Narasimhan
  • Publication number: 20200157589
    Abstract: A process for synthetically producing (S)-nicotine ([(S)-3-(1-methylpyrrolidin-2-yl) pyridine]) is provided.
    Type: Application
    Filed: March 12, 2019
    Publication date: May 21, 2020
    Applicant: ZANOPRIMA LIFESCIENCES LIMITED
    Inventors: Raymond MCCAGUE, Ashok Srinivasan NARASIMHAN
  • Publication number: 20150057452
    Abstract: Compounds having therapeutic potential as androgen receptor modulators, and methods of making such compounds, are provided. The compounds are structurally related to bicalutamide but bear at least one difluoromethyl or C2 to C5 perfluoroalkyl group instead of a trifluoromethyl group.
    Type: Application
    Filed: April 4, 2013
    Publication date: February 26, 2015
    Applicant: Catylix, Inc.
    Inventors: James David Rozzell, Raymond McCague
  • Patent number: 6184004
    Abstract: The subject invention pertains to a process for preparing a compound having a formula (4) or (5), in either optically-enriched or racemic form, wherein R1, R2, R3 and R4 are independently selected from hydrogen, alkyl, aryl, alkaryl, aralkyl and acyl groups. In one embodiment, the process of the invention comprises mixing with a plant extract obtained from crushed daffodil bulbs or crushed snowdrop bulbs an oxidative cyclisation precursor of the compound.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: February 6, 2001
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Robin Mark Bannister, Raymond McCague
  • Patent number: 6180374
    Abstract: Azlactone (3), or the opposite enantiomer thereof, undergoes biotransformation, using suitable enzymatic activity, in the presence of a compound YH to form a N-acyl-amino acid (2), wherein R1, R2 and R3 are each not hydrogen and are independently selected from groups containing up to 20 carbon atoms, optionally with any combination of R1, R2 and R3 being joined together to form at least one ring, X is selected from groups containing up to 20 carbon atoms, and Y is selected from the group consisting of —OH, -Oalkyl and -Nalkyl. Amino acid (1), or the opposite enantiomer thereof, can be prepared in high enantiomeric excess from N-acyl amino acid (2), by converting Y to OH.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: January 30, 2001
    Assignee: Chirotech Technology, Inc.
    Inventors: Nicholas Turner, James Winterman, Raymond McCague
  • Patent number: 6156900
    Abstract: A process for the preparation of optically-enriched pipecolic acid as a salt with an optically-active acid, comprises asymmetric transformation of pipecolic acid, as a racemic mixture of a mixture enriched in the opposite enantiomer from that desired, with the optically-active acid in a solvent comprising an acid that causes racemisation, in the absence of aldehyde.
    Type: Grant
    Filed: February 12, 1999
    Date of Patent: December 5, 2000
    Assignee: Darwin Discovery Limited
    Inventors: Ulrich Conrad Dyer, Martin Woods, Raymond McCague
  • Patent number: 6140512
    Abstract: A process for the preparation of lipolic acid (thioctic acid), or a derivative thereof, is one in which a 2-substituted cyclohexanone is transformed in an oxidation reaction to a lactone having formula (I), wherein X is a heteroatom substituent.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: October 31, 2000
    Assignee: ASTA Medica Aktiengesellschaft
    Inventors: Brian Michael Adger, Raymond McCague, Stanley Michael Roberts
  • Patent number: 6075156
    Abstract: A cycloalkanol is prepared by cycloaddition between a diene and a vinyl ester, wherein the ester is derived from a carboxylic acid of sufficient molecular weight to enable the reaction to be carried out at atmospheric pressure while above 150.degree. C., and the corresponding reaction between the diene and vinyl acetate generates a pressure above 4 atmospheres.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: June 13, 2000
    Assignee: Chirotech Technology Limited
    Inventors: Stephen John Clifford Taylor, Raymond McCague, Derek Thomas Edward Jones
  • Patent number: 6018043
    Abstract: The subject invention concerns a process for preparing a compound of formula (3) ##STR1## in enantio-enriched form, comprising reducing a compound of formula (4) ##STR2## using an asymmetric enantiospecific reductant, wherein A.sup.1 .dbd.A.sup.2 .dbd.H or A.sup.1, A.sup.2 .dbd.O; B.sup.1 .dbd.B.sup.2 .dbd.H or B.sup.1, B.sup.2 .dbd.O; Z.dbd.H, C.sub.1-20 alkyl or a precursor thereof, or a removable protecting group for nitrogen, e.g, acyl or alkyloxycarbonyl; Y.dbd.H or a substituent; R.sup.1 .dbd.C.sub.1-20 alkyl; and R is an optional, additional substituent.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: January 25, 2000
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Ulrich Conrad Dyer, Jane Marie Paul, Raymond McCague
  • Patent number: 5910601
    Abstract: The subject invention concerns a process for preparing a single enantiomer, either R or S, of R'--NH--(CH.sub.2).sub.3 --C(Ar)(CN)--R. The process is particularly useful for preparing verapamil, and analogues thereof, in single enantiomeric form.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: June 8, 1999
    Assignee: Darwin Discovery Limited
    Inventors: Raymond McCague, Shouming Wang
  • Patent number: 5898075
    Abstract: A process is described for obtaining a single enantiomer from a racemic mixture of the bicyclic lactam 2-azabicyclo?2.2. 1! hept-5-en-one by seeding a supersaturated solution of the lactam and a solvent with a single enantiomer of the lactam.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: April 27, 1999
    Assignee: Chirotech Technology Limited
    Inventors: Raymond McCague, Gerard Andrew Potter, Stephen John Clifford Taylor, Brian Michael Adger
  • Patent number: 5840923
    Abstract: An optically-purified enantiomer of the lactone 4-hydroxy-2-oxabicyclo-?3.3.0!oct-7-en-3-one or an acylate thereof can be obtained by biotransformation. It is a useful synthon in the preparation of an enantiomer of 3-hydroxymethyl-2-hydroxycyclopentene that can be used to prepare carbocyclic nucleosides as a desired enantiomer.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: November 24, 1998
    Assignee: Chiroscience Limited
    Inventors: Stanley Michael Roberts, Horacio F. Olivo, Raymond McCague
  • Patent number: 5821369
    Abstract: A process for the racemization of an enantiomerically-enriched compound of formula (3), comprises treatment of enantiomerically-enriched (3) with a base to obtain anion (4), optionally in protonated form, which is then combined with CH.sub.2 =CH--Y.sup.1 to form racemic (3), ##STR1## wherein Ar=aryl or heteroaryl; Ak=C.sub.1-20 alkyl; X=CN, CO.sub.2 R, CONR.sup.1 R.sup.2, and COR; Y and Y.sup.1 are independently selected from CN, CO.sub.2 R, CONR.sup.1 R.sup.2 and R, R.sub.1 and R.sub.2 are independently selected from H and C.sub.1-20 alkyl; optionally as a salt thereof.This racemization process can be used as part of an efficient synthesis of enantiomerically-enriched verapamil or aminoglutethimide.
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: October 13, 1998
    Assignee: Chiroscience Limited
    Inventor: Raymond McCague
  • Patent number: 5739332
    Abstract: A process for the product of a 2,3-cis-dihydroxycycloalkane-1-carboxamide, comprises dihydroxylation of the corresponding cycloalkene-1-carboxamide. Some products are new. The stereoselective dihydroxylation is surprising.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: April 14, 1998
    Assignee: Chiroscience Limited
    Inventors: Raymond McCague, Graham Ruecroft, Christopher Palmer
  • Patent number: 5661014
    Abstract: Enantiomeric glutarimides such as aminoglutethimide and rogletimide are prepared by cyclisation of a corresponding ester-nitrile which is a good substrate for biotransformation with an enantiospecific esterase.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: August 26, 1997
    Assignee: Chiroscience Limited
    Inventors: Christopher Thomas Evans, Raymond McCague, Stephen John Clifford Taylor
  • Patent number: 5523450
    Abstract: A process for preparing substantially dry GPC (glycerophosphocholine in enantiomeric form) from wet GPC without racemisation, comprises subjecting the wet GPC to reduced pressure and elevated temperature, to reduce the water content and give highly viscous GPC; adding ethanol or another suitable solvent and crystallising GPC therefore with cooling; filtering the crystalline GPC and removing solvent therefrom under reduced pressure; characterised in that the elevated temperature is at least 45.degree. C.; and the solvent is added to the highly viscous GPC. This process produces an apparently new form of L-.alpha.-Glycerophosphocholine, m.p. 148.degree.-152.degree. C.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: June 4, 1996
    Assignee: Genzyme Limited
    Inventors: Christopher T. Evans, Raymond McCague, Nicholas D. Tyrrell