Patents by Inventor Joerg Bruening

Joerg Bruening 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: 20230303482
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-12-oxo-2-[(2,2.2-trifluoroeihyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Application
    Filed: March 24, 2023
    Publication date: September 28, 2023
    Inventor: Joerg Bruening
  • Patent number: 11613516
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Grant
    Filed: January 14, 2019
    Date of Patent: March 28, 2023
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Joerg Bruening
  • Publication number: 20230061554
    Abstract: A method for preparing a compound of Formula (1) and compounds therefrom, comprising treating a compound of Formula (2) to provide a compound of Formula (5) and treating the compound of Formula (5) with a hydroxylamine salt wherein R1, R2 and m are as defined in the specification. The compound of Formula (1), prepared by the above method, can be used to prepare a compound of Formula (8) wherein R1, R2, R3 and m are as defined in the specification.
    Type: Application
    Filed: December 2, 2020
    Publication date: March 2, 2023
    Inventors: Junbae HONG, Joerg BRUENING
  • Patent number: 10745344
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Grant
    Filed: January 14, 2019
    Date of Patent: August 18, 2020
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Joerg Bruening
  • Publication number: 20190144373
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Application
    Filed: January 14, 2019
    Publication date: May 16, 2019
    Inventor: Joerg Bruening
  • Publication number: 20190144374
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Application
    Filed: January 14, 2019
    Publication date: May 16, 2019
    Inventor: Joerg Bruening
  • Patent number: 10202332
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: February 12, 2019
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Joerg Bruening
  • Patent number: 8748630
    Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one compound of Formula 3 in the presence of a solvent comprising one or more organic solvents selected from ethers and nitriles and a catalytically effective amount of a palladium complex comprising at least one tertiary phosphine ligand of Formula 4 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; M1 is an alkali metal; and R5, R6 and R7 are defined in the disclosure; provided that when R2 is Cl, then X is Br. Also disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the aforedescribed method.
    Type: Grant
    Filed: December 5, 2007
    Date of Patent: June 10, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Joerg Bruening, Albert Loren Casalnuovo, Vladimir Grushin
  • Publication number: 20130267729
    Abstract: Disclosed are methods for preparing compounds of Formula 1 and 1A. The first method utilizes a benzyl carbamate amine protecting group and an intermediate of Formula 4. The second method utilizes a tert-butyl carbamate amine protecting group and an intermediate of Formula 7. The third method utilizes a dibenzyl amine protecting group. Also disclosed is a compound, phenylmethyl N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]carbamate (a compound of Formula 4). Further disclosed is a method for preparing a compound of Formula 14 from a compound of Formula 15 and a compound of Formula 1 or 1A.
    Type: Application
    Filed: September 23, 2011
    Publication date: October 10, 2013
    Applicant: E.I. du Pont de Nemours and Company
    Inventor: Joerg Bruening
  • Patent number: 8049029
    Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: November 1, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joerg Bruening, Gary David Annis, Donald J Dumas, Rafael Shapiro
  • Publication number: 20100280251
    Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.
    Type: Application
    Filed: December 18, 2007
    Publication date: November 4, 2010
    Applicant: E.I. Du Pont De Nemours and Company
    Inventors: Joerg Bruening, Gary David Annis, Martin James Currie, Donald J. Dumas, Rafael Shapiro
  • Publication number: 20100022780
    Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with at least one compound of Formula 3 in the presence of a solvent comprising one or more organic solvents selected from ethers and nitrites and a catalytically effective amount of a palladium complex comprising at least one tertiary phosphine ligand of Formula 4 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; M1 is an alkali metal; and R5, R6 and R7 are defined in the disclosure; provided that when R2 is Cl, then X is Br. Also disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the aforedescribed method.
    Type: Application
    Filed: December 5, 2007
    Publication date: January 28, 2010
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Joerg Bruening, Albert Loren Casalnuovo, Vladimir Grushin
  • Patent number: 6495700
    Abstract: A process for preparing phenserine compounds which are known acetylcholinesterase inhibitors from physostigmine compounds by hydrolysis to form an eseroline compound which is then condensed with an isocyanate.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: December 17, 2002
    Assignee: Axonyx, Inc.
    Inventor: Joerg Bruening
  • Patent number: 6268537
    Abstract: A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.
    Type: Grant
    Filed: May 25, 1999
    Date of Patent: July 31, 2001
    Assignee: Mine Safety Appliances Company
    Inventors: Elizabeth R. Burkhardt, Christopher P. Sutton, Joerg Bruening, David F. Rouda
  • Patent number: 6221331
    Abstract: A synthetic route for forming lithium trisubstituted borohydride compounds comprises the step of reacting a processed lithium hydride reactant with a trisubstituted borane wherein the reaction is maintained for a period of time in a temperature range of approximately 15° C. to approximately 42° C. A method of synthesizing LiH comprises the step of reacting an alkyl lithium (for example, n-butyl lithium) with hydrogen in the presence of tetrahydrofuran. The reaction temperature is preferably maintained in the range of approximately −78° C. to approximately 25° C.
    Type: Grant
    Filed: January 24, 2000
    Date of Patent: April 24, 2001
    Assignee: Mine Safety Appliances Company
    Inventors: Elizabeth R. Burkhardt, Christopher P. Sutton, Joerg Bruening, David F. Rouda
  • Patent number: 5886229
    Abstract: Synthetic routes for forming alkali metal substituted borohydride compounds include the step of reacting an alkali metal reagent, a hydrogen donor, and a substituted borane. The reactions proceed without the requirement of specialized handling of alkali metal hydrides associated with prior synthetic processes for the production of alkali metal trisubstituted borohydride compounds. A chemical composition comprises solid potassium tri-sec-butyl borohydride.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: March 23, 1999
    Assignee: Mine Safety Appliances Company
    Inventors: Joseph A. Corella, II, David H. Ellenberger, Joerg Bruening