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WO2009054004A3 - Process for the preparation of sorafenib - Google Patents

Process for the preparation of sorafenib Download PDF

Info

Publication number
WO2009054004A3
WO2009054004A3 PCT/IN2008/000698 IN2008000698W WO2009054004A3 WO 2009054004 A3 WO2009054004 A3 WO 2009054004A3 IN 2008000698 W IN2008000698 W IN 2008000698W WO 2009054004 A3 WO2009054004 A3 WO 2009054004A3
Authority
WO
WIPO (PCT)
Prior art keywords
sorafenib
preparation
formula
novel
kinase
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/IN2008/000698
Other languages
French (fr)
Other versions
WO2009054004A2 (en
Inventor
Reddy Muddasani Pulla
Chowdary Nannapaneni Venkaiah
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.)
Natco Pharma Ltd
Original Assignee
Natco Pharma Ltd
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 Natco Pharma Ltd filed Critical Natco Pharma Ltd
Publication of WO2009054004A2 publication Critical patent/WO2009054004A2/en
Publication of WO2009054004A3 publication Critical patent/WO2009054004A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A novel and improved process for the preparation of sorafenib (4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide) of formula (I) involving a novel intermediate of formula (II) as key intermediate is disclosed. Sorafenib tosylate, available in the market as Nexavar is a multiple kinase inhibitor targeting both RAF kinase and receptor tyrosine kinase that promote angiogenesis.
PCT/IN2008/000698 2007-10-22 2008-10-22 Process for the preparation of sorafenib Ceased WO2009054004A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2372CH2007 2007-10-22
IN2372/CHE/2007 2007-10-22

Publications (2)

Publication Number Publication Date
WO2009054004A2 WO2009054004A2 (en) 2009-04-30
WO2009054004A3 true WO2009054004A3 (en) 2009-07-02

Family

ID=40527499

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000698 Ceased WO2009054004A2 (en) 2007-10-22 2008-10-22 Process for the preparation of sorafenib

Country Status (1)

Country Link
WO (1) WO2009054004A2 (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
HK1042251B (en) 1999-01-13 2012-07-20 Bayer Healthcare Llc Omega-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors
EP1478358B1 (en) 2002-02-11 2013-07-03 Bayer HealthCare LLC Sorafenib tosylate for the treatment of diseases characterized by abnormal angiogenesis
PT1626714E (en) 2003-05-20 2007-08-24 Bayer Pharmaceuticals Corp DIARILURIES FOR PDGFR MEDICATED DISEASES
CA2775296A1 (en) 2009-09-24 2011-03-31 Ranbaxy Laboratories Limited Polymorphs of sorafenib acid addition salts
EP2480534A1 (en) 2009-09-24 2012-08-01 Ranbaxy Laboratories Limited Process for the preparation of sorafenib tosylate
EP2499116A1 (en) 2009-11-12 2012-09-19 Ranbaxy Laboratories Limited Sorafenib ethylsulfonate salt, process for preparation and use
US8618305B2 (en) 2010-01-29 2013-12-31 Ranbaxy Laboratories Limited Sorafenib dimethyl sulphoxide solvate
CN102190616B (en) 2010-03-18 2015-07-29 苏州泽璟生物制药有限公司 A kind of deuterated synthesis of ω-diphenyl urea and the Method and process of production
CN103408488A (en) * 2013-08-13 2013-11-27 张家港威胜生物医药有限公司 Optimal synthetic method of sorafenib
PT3039424T (en) 2013-08-28 2020-09-03 Crown Bioscience Inc Taicang Gene expression signatures predictive of subject response to a multi-kinase inhibitor and methods of using the same
CN104761492A (en) * 2014-01-03 2015-07-08 正大天晴药业集团股份有限公司 Crystal form of sorafenib tosylate, and preparation method thereof
CN104177292A (en) * 2014-08-08 2014-12-03 亿腾药业（泰州）有限公司 Method for industrial production of sorafenib tosylate polymorphic form I
CN105481764A (en) * 2014-09-16 2016-04-13 重庆圣华曦药业股份有限公司 Preparation method of sorafenib p-toluenesulfonate
CN105399668B (en) * 2015-12-29 2018-11-16 开封制药(集团)有限公司 A kind of method that " one kettle way " prepares Sorafenib
CN105801475B (en) * 2016-04-25 2018-01-12 华润双鹤利民药业（济南）有限公司 A kind of preparation method of Sorafenib Tosylate
CN109796400B (en) * 2017-11-16 2022-07-29 四川科伦药物研究院有限公司 Sorafenib tosylate crystal form and preparation method thereof
MX2021008918A (en) * 2019-01-31 2021-08-24 Ionis Pharmaceuticals Inc Modulators of yap1 expression.

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0848078A (en) * 1994-08-05 1996-02-20 Nippon Paper Ind Co Ltd Heat-sensitive recorder
WO2000042012A1 (en) * 1999-01-13 2000-07-20 Bayer Corporation φ-CARBOXYARYL SUBSTITUTED DIPHENYL UREAS AS RAF KINASE INHIBITORS
WO2000041698A1 (en) * 1999-01-13 2000-07-20 Bayer Corporation φ-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS
WO2003068228A1 (en) * 2002-02-11 2003-08-21 Bayer Pharmaceuticals Corporation Aryl ureas with angiogenesis inhibiting activity
WO2006034796A1 (en) * 2004-09-29 2006-04-06 Bayer Healthcare Ag Process for the preparation of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n-methylpyridine-2-carboxamide
EP1683785A1 (en) * 2003-11-11 2006-07-26 Eisai Co., Ltd. Urea derivative and process for producing the same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0848078A (en) * 1994-08-05 1996-02-20 Nippon Paper Ind Co Ltd Heat-sensitive recorder
WO2000042012A1 (en) * 1999-01-13 2000-07-20 Bayer Corporation φ-CARBOXYARYL SUBSTITUTED DIPHENYL UREAS AS RAF KINASE INHIBITORS
WO2000041698A1 (en) * 1999-01-13 2000-07-20 Bayer Corporation φ-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS
WO2003068228A1 (en) * 2002-02-11 2003-08-21 Bayer Pharmaceuticals Corporation Aryl ureas with angiogenesis inhibiting activity
EP1683785A1 (en) * 2003-11-11 2006-07-26 Eisai Co., Ltd. Urea derivative and process for producing the same
WO2006034796A1 (en) * 2004-09-29 2006-04-06 Bayer Healthcare Ag Process for the preparation of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n-methylpyridine-2-carboxamide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
D. BANKSTON ET AL.: "A Scalable Synthesis of BAY 43-9006: A Potent Raf Kinase Inhibitor for the Treatment of Cancer", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 6, no. 6, 2002, pages 777 - 781, XP002523918 *
PAN W ET AL: "Pyrimido-oxazepine as a versatile template for the development of inhibitors of specific kinases", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 15, no. 24, 15 December 2005 (2005-12-15), pages 5474 - 5477, XP025314229, ISSN: 0960-894X, [retrieved on 20051215] *

Also Published As

Publication number Publication date
WO2009054004A2 (en) 2009-04-30

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