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WO2014114964A3 - Improved process for the preparation of prasugrel and intermediate thereof - Google Patents

Improved process for the preparation of prasugrel and intermediate thereof Download PDF

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Publication number
WO2014114964A3
WO2014114964A3 PCT/HU2014/000008 HU2014000008W WO2014114964A3 WO 2014114964 A3 WO2014114964 A3 WO 2014114964A3 HU 2014000008 W HU2014000008 W HU 2014000008W WO 2014114964 A3 WO2014114964 A3 WO 2014114964A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
prasugrel
formula
improved process
cyclopropylcarbonylbenzyl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/HU2014/000008
Other languages
French (fr)
Other versions
WO2014114964A2 (en
Inventor
Bálint NYULASI
Edina KOVÁCS
Éva SZABÓ
Gabriella PÁKAINÉ VARGA
Márta PORCS-MAKKAY
Balász VOLK
Gyula LUKÁCS
Károlyné VÁRADY
György RUZSICS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Egis Pharmaceuticals PLC
Original Assignee
Egis Pharmaceuticals PLC
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 Egis Pharmaceuticals PLC filed Critical Egis Pharmaceuticals PLC
Publication of WO2014114964A2 publication Critical patent/WO2014114964A2/en
Publication of WO2014114964A3 publication Critical patent/WO2014114964A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention relates to an industrial scale process for the preparation of 1-cyclopropyl-2-(2-fluorophenyl)ethanone of Formula (1) (Formula (1)) and the use of this compound for the preparation of 2-acetoxy-5-(2- fluoro-α-cyclopropylcarbonylbenzyl)-4,5,6,7-tetrahydro-4H-thieno[3,2-c]pyridine (prasugrel) of Formula (5). ((Formula (5))
PCT/HU2014/000008 2013-01-24 2014-01-24 Improved process for the preparation of prasugrel and intermediate thereof Ceased WO2014114964A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU1300033A HU230649B1 (en) 2013-01-24 2013-01-24 Improved process for producing pharmaceutical agent prasugrel and 2-(2-fluorophenyl)-1-cyclopropylethanone intermediate
HUP1300033 2013-01-24

Publications (2)

Publication Number Publication Date
WO2014114964A2 WO2014114964A2 (en) 2014-07-31
WO2014114964A3 true WO2014114964A3 (en) 2014-09-18

Family

ID=89991006

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2014/000008 Ceased WO2014114964A2 (en) 2013-01-24 2014-01-24 Improved process for the preparation of prasugrel and intermediate thereof

Country Status (2)

Country Link
HU (1) HU230649B1 (en)
WO (1) WO2014114964A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105884599A (en) * 2016-06-09 2016-08-24 青岛辰达生物科技有限公司 Method for preparing antithrombotic drug prasugrel intermediate
CN105884793A (en) * 2016-06-09 2016-08-24 青岛辰达生物科技有限公司 Preparation method of antiplatelet medicine Prasugrel
HU231079B1 (en) 2016-06-23 2020-06-29 Richter Gedeon Nyrt. Process for the preparation of high-purity prasugrel by the elimination of the bromopentyl impurity
CN107056803B (en) * 2017-05-19 2019-06-11 兰州大学 Intermediates for synthesizing prasugrel and its preparation method and method for synthesizing prasugrel
WO2024138216A2 (en) * 2022-12-23 2024-06-27 Case Western Reserve University Compositions and methods for treating and detecting cancer

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009068923A2 (en) * 2007-11-27 2009-06-04 Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság Process for the preparation of pharmaceutical intermediates

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2042336A1 (en) 1990-05-11 1991-11-12 Mitsuo Nagano Piperidyloxy-and quinuclidinyloxy-isoxazole, derivatives, their preparation and their therapeutic use
FI101150B (en) 1991-09-09 1998-04-30 Sankyo Co Process for the preparation of tetrahydrothione nopyridine derivatives useful as a drug
EP0785205B1 (en) 1994-10-07 2002-04-17 Ube Industries, Ltd. 2-silyloxytetrahydrothienopyridine, salt thereof, and process for producing the same
EP1728794B1 (en) 2000-07-06 2008-06-18 Daiichi Sankyo Company, Limited Maleate addition salt of hydropyridine derivatives
US20100261908A1 (en) 2007-11-09 2010-10-14 Dr. Reddy's Laboratories Ltd. Processes for the preparation of prasugrel , and its salts and polymorphs
WO2009066326A2 (en) 2007-11-19 2009-05-28 Msn Laboratories Limited Improved process for the preparation of prasugrel and its pharmaceutically acceptable salts
CN101250192B (en) 2008-03-24 2010-08-11 上海医药工业研究院 Method for preparing 5-(alpha-cyclopropyl carbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothiophene [3,2-c] pyridine
WO2009122440A1 (en) 2008-03-31 2009-10-08 Torrent Pharmaceuticals Ltd. PROCESS FOR THE PREPARATION OF 2-ACETOXY-5-(α -CYCLOPRPYLCARBONYL -2-FLUOROBENZYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE
CN101531667A (en) 2009-04-16 2009-09-16 上海立科药物化学有限公司 Method for synthesizing prasugrel intermediate and method for synthesizing prasugrel
HUP1000565A2 (en) 2010-10-22 2012-05-02 Egis Gyogyszergyar Nyrt Process for the preparation of pharmaceutically active compound and intermediers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009068923A2 (en) * 2007-11-27 2009-06-04 Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság Process for the preparation of pharmaceutical intermediates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
M SZWARC ET AL: "New Compounds. The Di-fluorobibenzyls", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 70, no. 8, 1948, pages 2831, XP055109979, ISSN: 0002-7863, DOI: 10.1021/ja01188a602 *

Also Published As

Publication number Publication date
HU230649B1 (en) 2017-05-29
WO2014114964A2 (en) 2014-07-31
HUP1300033A2 (en) 2014-07-28

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