CA2698795C - Process for the preparation of a raf kinase inhibitor and intermediates for use in the process - Google Patents

Process for the preparation of a raf kinase inhibitor and intermediates for use in the process Download PDF

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Publication number
CA2698795C
CA2698795C CA2698795A CA2698795A CA2698795C CA 2698795 C CA2698795 C CA 2698795C CA 2698795 A CA2698795 A CA 2698795A CA 2698795 A CA2698795 A CA 2698795A CA 2698795 C CA2698795 C CA 2698795C
Authority
CA
Canada
Prior art keywords
sorafenib
derivative
compound
salt
acid
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.)
Expired - Fee Related
Application number
CA2698795A
Other languages
English (en)
French (fr)
Other versions
CA2698795A1 (en
Inventor
Dharmaraj Ramachandra Rao
Rajendra Narayanrao Kankan
Maruti Ghagare
Sandip Chikhalikar
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.)
Cipla Ltd
Original Assignee
Cipla 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 Cipla Ltd filed Critical Cipla Ltd
Publication of CA2698795A1 publication Critical patent/CA2698795A1/en
Application granted granted Critical
Publication of CA2698795C publication Critical patent/CA2698795C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2698795A 2007-09-10 2008-09-10 Process for the preparation of a raf kinase inhibitor and intermediates for use in the process Expired - Fee Related CA2698795C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IN1733MU2007 2007-09-10
IN1733/MUM/2007 2007-09-10
IN1734/MUM/2007 2007-09-10
IN1734MU2007 2007-09-10
PCT/GB2008/003048 WO2009034308A2 (en) 2007-09-10 2008-09-10 Process for the preparation of a raf kinase inhibitor and intermediates for use in the process

Publications (2)

Publication Number Publication Date
CA2698795A1 CA2698795A1 (en) 2009-03-19
CA2698795C true CA2698795C (en) 2016-04-19

Family

ID=40351766

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2698795A Expired - Fee Related CA2698795C (en) 2007-09-10 2008-09-10 Process for the preparation of a raf kinase inhibitor and intermediates for use in the process

Country Status (9)

Country Link
US (1) US8445687B2 (OSRAM)
EP (1) EP2195286A2 (OSRAM)
JP (1) JP5438680B2 (OSRAM)
KR (1) KR101553211B1 (OSRAM)
AU (1) AU2008299703C1 (OSRAM)
CA (1) CA2698795C (OSRAM)
NZ (1) NZ583790A (OSRAM)
WO (1) WO2009034308A2 (OSRAM)
ZA (1) ZA201001935B (OSRAM)

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US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
JP2002534468A (ja) 1999-01-13 2002-10-15 バイエル コーポレイション ｐ３８キナーゼ阻害剤としてのω−カルボキシアリール置換ジフェニル尿素
PT1478358E (pt) 2002-02-11 2013-09-11 Bayer Healthcare Llc Tosilato de sorafenib para o tratamento de doenças caracterizadas por angiogénese anormal
PL1626714T3 (pl) 2003-05-20 2007-12-31 Bayer Healthcare Llc Diarylowe pochodne mocznika do schorzeń, w których pośredniczy PDGFR
CA2698795C (en) 2007-09-10 2016-04-19 Cipla Limited Process for the preparation of a raf kinase inhibitor and intermediates for use in the process
BRPI0918268B1 (pt) 2008-09-02 2021-08-03 Novartis Ag Derivados de picolinamida, seu uso, e composição farmacêutica
US8604208B2 (en) 2009-09-24 2013-12-10 Ranbaxy Laboratories Limited Polymorphs of sorafenib acid addition salts
AU2010299483B2 (en) 2009-09-24 2014-08-28 Sun Pharmaceutical Industries Limited Process for the preparation of sorafenib tosylate
WO2011058522A1 (en) 2009-11-12 2011-05-19 Ranbaxy Laboratories Limited Sorafenib ethylsulfonate salt, process for preparation and use
PL2528899T3 (pl) 2010-01-29 2015-02-27 Ranbaxy Laboratories Ltd Solwat sorafenibu z dimetylosulfotlenkiem
CN102190616B (zh) * 2010-03-18 2015-07-29 苏州泽璟生物制药有限公司 一种氘代的ω-二苯基脲的合成及生产的方法和工艺
US9102593B2 (en) * 2011-01-18 2015-08-11 Glaxo Group Limited Process for the preparation of retigabine
CN102485714B (zh) * 2011-10-09 2013-07-24 连云港盛和生物科技有限公司 一种羰基化合成索拉菲尼的方法
HK1206021A1 (en) 2012-05-21 2015-12-31 Novartis Ag Novel ring-substituted n-pyridinyl amides as kinase inhibitors
CN103508961B (zh) * 2012-06-26 2015-07-22 中美冠科生物技术（太仓）有限公司 抗肿瘤药物
CN103408488A (zh) * 2013-08-13 2013-11-27 张家港威胜生物医药有限公司 一种索拉非尼的优化合成方法
PT3039424T (pt) 2013-08-28 2020-09-03 Crown Bioscience Inc Taicang Assinaturas de expressão genética que permitem prever a resposta de um sujeito a um inibidor multiquinase e métodos de utilização do mesmo
CN104761492A (zh) * 2014-01-03 2015-07-08 正大天晴药业集团股份有限公司 对甲苯磺酸索拉非尼的晶型及其制备方法
CN105481764A (zh) * 2014-09-16 2016-04-13 重庆圣华曦药业股份有限公司 一种索拉非尼对甲苯磺酸盐的制备方法
CN105399668B (zh) * 2015-12-29 2018-11-16 开封制药(集团)有限公司 一种“一锅法”制备索拉菲尼的方法
CN105801475B (zh) * 2016-04-25 2018-01-12 华润双鹤利民药业（济南）有限公司 一种甲苯磺酸索拉非尼的制备方法
CN109796400B (zh) * 2017-11-16 2022-07-29 四川科伦药物研究院有限公司 一种甲苯磺酸索拉菲尼晶型及其制备方法
CN108623521B (zh) * 2018-03-22 2020-09-04 盐城师范学院 一种乐伐替尼的制备方法
CN108276328A (zh) * 2018-03-31 2018-07-13 山东罗欣药业集团恒欣药业有限公司 一种索拉非尼的制备方法
CN108276327A (zh) * 2018-03-31 2018-07-13 山东罗欣药业集团恒欣药业有限公司 一种索拉非尼的制备方法
CN108586329A (zh) * 2018-03-31 2018-09-28 山东罗欣药业集团恒欣药业有限公司 一种索拉非尼的合成方法
CN108558747A (zh) * 2018-03-31 2018-09-21 山东罗欣药业集团恒欣药业有限公司 一种瑞戈非尼的制备方法
CN108341770A (zh) * 2018-03-31 2018-07-31 山东罗欣药业集团恒欣药业有限公司 一种索拉非尼化合物的制备方法
CN108440403A (zh) * 2018-03-31 2018-08-24 山东罗欣药业集团恒欣药业有限公司 一种瑞戈非尼的制备方法
CN108586330A (zh) * 2018-04-18 2018-09-28 日照市普达医药科技有限公司 一种治疗肿瘤药物的制备方法及其应用
KR20220038696A (ko) 2019-07-19 2022-03-29 아나제네시스 바이오테크놀로지스 에스.에이.에스. 폴리방향족 우레아 유도체 및 근육 질환 치료에서의 이들의 용도
EP4029501A1 (en) 2021-01-19 2022-07-20 Anagenesis Biotechnologies Combination of polyaromatic urea derivatives and glucocorticoid or hdac inhibitor for the treatment of diseases or conditions associated with muscle cells and/or satellite cells

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CA2698795C (en) 2007-09-10 2016-04-19 Cipla Limited Process for the preparation of a raf kinase inhibitor and intermediates for use in the process

Also Published As

Publication number Publication date
ZA201001935B (en) 2010-11-24
US8445687B2 (en) 2013-05-21
JP2010539076A (ja) 2010-12-16
AU2008299703C1 (en) 2013-09-05
WO2009034308A2 (en) 2009-03-19
KR20100074175A (ko) 2010-07-01
US20100311980A1 (en) 2010-12-09
CA2698795A1 (en) 2009-03-19
AU2008299703B2 (en) 2013-06-20
AU2008299703A1 (en) 2009-03-19
EP2195286A2 (en) 2010-06-16
KR101553211B1 (ko) 2015-09-15
NZ583790A (en) 2012-04-27
JP5438680B2 (ja) 2014-03-12
WO2009034308A3 (en) 2009-07-16

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