Patents by Inventor Bruno Hache

Bruno Hache 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).

  • Process for the preparation of (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide and salts thereof
    Patent number: 11214571
    Abstract: Process for preparing (S)—N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a] pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide (formula I) or a salt thereof by reacting phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate or a similar derivative (formula 13) with (S)-pyrrolidin-3-ol (formula 14). Process for preparing phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate (formula 13) or a similar derivative by reduction of (R)-5-(2-(2,5-difluorophenyl) pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine (formula 11) to (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (formula 12). Process for preparing (R)-2-(2,5-difluorophenyl)pyrrolidine(R)-2-hydroxysuccinate (formula 10) by treating (R)—N—((R)-1-(2,5-difluorophenyl)-3-(1,3-dioxan-2-yl)propyl)-2-methylpropane-2-sulfinamide (formula 19) with an acid and a reducing agent.
    Type: Grant
    Filed: May 18, 2017
    Date of Patent: January 4, 2022
    Assignees: Array BioPharma Inc., Loxo Oncology, Inc.
    Inventors: Mark Reynolds, Charles Todd Eary, Stacey Spencer, Derrick Juengst, Bruno Hache, Yutong Jiang, Julia Haas, Steven W. Andrews
  • PROCESS FOR THE PREPARATION OF (S)-N-(5-((R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDIN-1-YL)-PYRAZOLO[1,5-A]PYRIMIDIN-3-YL)-3-HYDROXYPYRROLIDINE-1-CARBOXAMIDE AND SALTS THEREOF
    Publication number: 20190218222
    Abstract: Process for preparing (S)—N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a] pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide (formula I) or a salt thereof by reacting phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate or a similar derivative (formula 13) with (S)-pyrrolidin-3-ol (formula 14). Process for preparing phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate (formula 13) or a similar derivative by reduction of (R)-5-(2-(2,5-difluorophenyl) pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine (formula 11) to (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (formula 12). Process for preparing (R)-2-(2,5-difluorophenyl)pyrrolidine(R)-2-hydroxysuccinate (formula 10) by treating (R)—N—((R)-1-(2,5-difluorophenyl)-3-(1,3-dioxan-2-yl)propyl)-2-methylpropane-2-sulfinamide (formula 19) with an acid and a reducing agent.
    Type: Application
    Filed: May 18, 2017
    Publication date: July 18, 2019
    Inventors: Mark Reynolds, Charles Todd Eary, Stacey Spencer, Derrick Juengst, Bruno Hache, Yutong Jiang, Julia Haas, Steven W. Andrews
  • Inhibitors of papilloma virus
    Patent number: 7807670
    Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A,; X, W, R1, Y; R3; and R4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.
    Type: Grant
    Filed: November 13, 2008
    Date of Patent: October 5, 2010
    Assignee: Boehringer Ingelheim Canada Ltd.
    Inventors: Christiane Yoakim, Bruno Hache, William W. Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau
  • INHIBITORS OF PAPILLOMA VIRUS
    Publication number: 20100041649
    Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A, X, W, R1, Y; R3; and R4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.
    Type: Application
    Filed: November 13, 2008
    Publication date: February 18, 2010
    Inventors: Christiane Yoakim, Bruno Hache, William W. Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau
  • Inhibitors of papilloma virus
    Publication number: 20050009855
    Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A,; X, W, R1, Y; R3; and R4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.
    Type: Application
    Filed: February 4, 2004
    Publication date: January 13, 2005
    Applicant: Boehringer Ingelheim (Canada) Ltd.
    Inventors: Christiane Yoakim, Bruno Hache, William Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau
  • Inhibitors of papilloma virus
    Patent number: 6759409
    Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A,; X, W, R1, Y; R3; and R4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: July 6, 2004
    Assignee: Boehringer Ingelheim (Canada) Ltd.
    Inventors: Christiane Yoakim, Bruno Haché, William W. Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau
  • Inhibitors of papilloma virus
    Publication number: 20030064985
    Abstract: A compound of formula (I) or its enantiomers or diastereoisomers thereof: 1
    Type: Application
    Filed: December 17, 2001
    Publication date: April 3, 2003
    Inventors: Christiane Yoakim, Bruno Hache, William W. Ogilvie, Jeffrey O'Meara, Peter White, Nathalie Goudreau