WO2017223231A1 - (s)-8-(benzhydryl)-6-isopropyl-3,5-dioxo-5,6,7,8,-tétrahydro-3 h-pyrazino-[1,2-b] pyridazin-yl-isobutyrate, agent antiviral destiné à être utilisé dans le traitement de la grippe - Google Patents

(s)-8-(benzhydryl)-6-isopropyl-3,5-dioxo-5,6,7,8,-tétrahydro-3 h-pyrazino-[1,2-b] pyridazin-yl-isobutyrate, agent antiviral destiné à être utilisé dans le traitement de la grippe Download PDF

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Publication number
WO2017223231A1
WO2017223231A1 PCT/US2017/038594 US2017038594W WO2017223231A1 WO 2017223231 A1 WO2017223231 A1 WO 2017223231A1 US 2017038594 W US2017038594 W US 2017038594W WO 2017223231 A1 WO2017223231 A1 WO 2017223231A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
acceptable salt
pharmaceutically acceptable
food
Prior art date
Application number
PCT/US2017/038594
Other languages
English (en)
Inventor
John Fry
Thomas KAKUDA
Jeysen Z. YOGARATNAM
Sushmita Mukherjee CHANDA
Original Assignee
Alios Biopharma, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alios Biopharma, Inc. filed Critical Alios Biopharma, Inc.
Publication of WO2017223231A1 publication Critical patent/WO2017223231A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses

Definitions

  • high-calorie meal refers to a meal of food having at least 500 total calories in a single meal. In some embodiments, a high calorie meal constitutes approximately 500 to 2000 total calories in a single meal. In some embodiments, a high calorie meal constitutes approximately 800 to 1000 total calories in a single meal.
  • the time to maximum plasma concentration of an active form of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, (such as a compound of Formula (la), or a pharmaceutically acceptable salt thereof) is increased as compared to the administration of the pharmaceutical composition without food at least 3- fold. In some embodiments, the time to maximum plasma concentration of an active form of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, (such as a compound of Formula (la), or a pharmaceutically acceptable salt thereof) is increased as compared to the administration of the pharmaceutical composition without food in the range of 1-fold to 2-fold.
  • C max and AUCo o were 3.0 and 2.4-fold, respectively, higher for the compound of Formula (la) with the tablet than with the suspension.
  • a standard meal administered with a single dose of a compound Formula (I) (150 mg) as a tablet significantly increased exposure to a compound Formula (I), about 2-fold relative to the same dose as a tablet under fasted conditions.
  • the PK parameters of a compound Formula (I) are provided in Table 4.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'un composé spécifique, par exemple du (S)-8-(benzhydryl)-6-isopropyl-3,5-dioxo-5,6,7,8,-tétrahydro-3 H-pyrazino-[1,2-b]pyridazin-yl-isobutyrate (RegNo 1674397-77-3) destiné à être utilisé dans une méthode de traitement d'une infection grippale.
PCT/US2017/038594 2016-06-21 2017-06-21 (s)-8-(benzhydryl)-6-isopropyl-3,5-dioxo-5,6,7,8,-tétrahydro-3 h-pyrazino-[1,2-b] pyridazin-yl-isobutyrate, agent antiviral destiné à être utilisé dans le traitement de la grippe WO2017223231A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662352690P 2016-06-21 2016-06-21
US62/352,690 2016-06-21

Publications (1)

Publication Number Publication Date
WO2017223231A1 true WO2017223231A1 (fr) 2017-12-28

Family

ID=59276866

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2017/038594 WO2017223231A1 (fr) 2016-06-21 2017-06-21 (s)-8-(benzhydryl)-6-isopropyl-3,5-dioxo-5,6,7,8,-tétrahydro-3 h-pyrazino-[1,2-b] pyridazin-yl-isobutyrate, agent antiviral destiné à être utilisé dans le traitement de la grippe

Country Status (1)

Country Link
WO (1) WO2017223231A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180118760A1 (en) 2015-04-28 2018-05-03 Shionogi & Co., Ltd. Substituted polycyclic pyridone derivatives and prodrugs thereof
US10183945B2 (en) 2016-03-10 2019-01-22 Alios Biopharma, Inc. Method of preparing AZA-pyridone compounds
US10208045B2 (en) 2015-03-11 2019-02-19 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
US10251882B2 (en) 2013-09-12 2019-04-09 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
US10273233B2 (en) 2015-05-13 2019-04-30 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US10364226B2 (en) 2013-09-12 2019-07-30 Alios Biopharma, Inc. Pyridazinone compounds and uses thereof
US10759814B2 (en) 2016-08-10 2020-09-01 Shionogi & Co., Ltd. Pharmaceutical compositions containing substituted polycyclic pyridone derivatives and prodrug thereof
US10875855B2 (en) 2011-08-01 2020-12-29 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US10874673B2 (en) 2009-06-17 2020-12-29 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US11040048B2 (en) 2015-12-15 2021-06-22 Shionogi & Co., Ltd. Medicament for treating influenza characterized by combining a Cap-dependent endonuclease inhibitor and an anti-influenza drug
US11485753B2 (en) 2012-12-21 2022-11-01 Janssen Pharmaceutica Nv Substituted nucleosides, nucleotides and analogs thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006130686A2 (fr) * 2005-06-02 2006-12-07 Schering Corporation Administration d'inhibiteurs de protease du vhc en combinaison avec des aliments pour ameliorer la biodisponibilite
WO2007133481A2 (fr) * 2006-05-11 2007-11-22 Neuromed Pharmaceuticals Ltd. Méthode d'augmentation de la biodisponibilité de composés contenant de la benzhydrylpipérazine
US20150072982A1 (en) 2013-09-12 2015-03-12 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
US20160264581A1 (en) 2015-03-11 2016-09-15 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006130686A2 (fr) * 2005-06-02 2006-12-07 Schering Corporation Administration d'inhibiteurs de protease du vhc en combinaison avec des aliments pour ameliorer la biodisponibilite
WO2007133481A2 (fr) * 2006-05-11 2007-11-22 Neuromed Pharmaceuticals Ltd. Méthode d'augmentation de la biodisponibilité de composés contenant de la benzhydrylpipérazine
US20150072982A1 (en) 2013-09-12 2015-03-12 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
WO2015038655A1 (fr) 2013-09-12 2015-03-19 Alios Biopharma, Inc. Composés d'aza-pyridone et leurs utilisations
US20160264581A1 (en) 2015-03-11 2016-09-15 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
WO2016145103A1 (fr) 2015-03-11 2016-09-15 Alios Biopharma, Inc. Composés d'aza-pyridone et leurs utilisations

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Guidance for Industry Food-Effect Bioavailability and Fed Bioequivalence Studies", 1 December 2002 (2002-12-01), pages 1 - 12, XP008138108, Retrieved from the Internet <URL:http://www.fda.gov/downloads/RegulatoryInformation/Guidances/UCM126833.pdf> *
"Guidance for Industry, Food-Effect Bioavailability and Fed Bioequivalence Studies", December 2002, U.S. DEPARTMENT OF HEALTH AND HUMAN SERVICES FOOD
PARTICLE SCIENCES DRUG DEVELOPMENT SERVICES TECHNICAL BRIEF, vol. 9, 2011

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10874673B2 (en) 2009-06-17 2020-12-29 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US10875855B2 (en) 2011-08-01 2020-12-29 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US11485753B2 (en) 2012-12-21 2022-11-01 Janssen Pharmaceutica Nv Substituted nucleosides, nucleotides and analogs thereof
US10251882B2 (en) 2013-09-12 2019-04-09 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
US10364226B2 (en) 2013-09-12 2019-07-30 Alios Biopharma, Inc. Pyridazinone compounds and uses thereof
US10702523B2 (en) 2013-09-12 2020-07-07 Janssen Biopharma, Inc. AZA-pyridone compounds and uses thereof
US10980805B2 (en) 2013-09-12 2021-04-20 Janssen Biopharma, Inc. Aza-pyridone compounds and uses thereof
US10208045B2 (en) 2015-03-11 2019-02-19 Alios Biopharma, Inc. Aza-pyridone compounds and uses thereof
US10392406B2 (en) 2015-04-28 2019-08-27 Shionogi & Co., Ltd. Substituted polycyclic pyridone derivatives and prodrugs thereof
US20180118760A1 (en) 2015-04-28 2018-05-03 Shionogi & Co., Ltd. Substituted polycyclic pyridone derivatives and prodrugs thereof
US10273233B2 (en) 2015-05-13 2019-04-30 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
US11040048B2 (en) 2015-12-15 2021-06-22 Shionogi & Co., Ltd. Medicament for treating influenza characterized by combining a Cap-dependent endonuclease inhibitor and an anti-influenza drug
US10183945B2 (en) 2016-03-10 2019-01-22 Alios Biopharma, Inc. Method of preparing AZA-pyridone compounds
US10759814B2 (en) 2016-08-10 2020-09-01 Shionogi & Co., Ltd. Pharmaceutical compositions containing substituted polycyclic pyridone derivatives and prodrug thereof
US11306106B2 (en) 2016-08-10 2022-04-19 Shionogi & Co., Ltd. Pharmaceutical compositions containing substituted polycyclic pyridone derivatives and prodrug thereof

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