WO2010048477A3 - Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates - Google Patents

Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates Download PDF

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Publication number
WO2010048477A3
WO2010048477A3 PCT/US2009/061787 US2009061787W WO2010048477A3 WO 2010048477 A3 WO2010048477 A3 WO 2010048477A3 US 2009061787 W US2009061787 W US 2009061787W WO 2010048477 A3 WO2010048477 A3 WO 2010048477A3
Authority
WO
WIPO (PCT)
Prior art keywords
amino
cyanoquinolines
preparation
improved process
coupled products
Prior art date
Application number
PCT/US2009/061787
Other languages
French (fr)
Other versions
WO2010048477A2 (en
Inventor
Alexander Gontcharov
Kan Kaung Eng
Karen Sutherland
Alice Sebastian
Qing Yu
David William Place
Original Assignee
Wyeth Llc
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 Wyeth Llc filed Critical Wyeth Llc
Publication of WO2010048477A2 publication Critical patent/WO2010048477A2/en
Publication of WO2010048477A3 publication Critical patent/WO2010048477A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This invention discloses improved methods for coupling a 4-(amino)-2-butenoyl group to an amino group at the 6- or 7-position of a 4-amino-3-quinolinecarbonitrile by generating a stabilized 4-(amino)-2-butenoyl chloride hydrochloride.
PCT/US2009/061787 2008-10-24 2009-10-23 Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates WO2010048477A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10825408P 2008-10-24 2008-10-24
US61/108,254 2008-10-24

Publications (2)

Publication Number Publication Date
WO2010048477A2 WO2010048477A2 (en) 2010-04-29
WO2010048477A3 true WO2010048477A3 (en) 2011-02-24

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ID=41590915

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/061787 WO2010048477A2 (en) 2008-10-24 2009-10-23 Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates

Country Status (1)

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WO (1) WO2010048477A2 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006084058A2 (en) 2005-02-03 2006-08-10 The General Hospital Corporation Method for treating gefitinib resistant cancer
WO2007056118A1 (en) 2005-11-04 2007-05-18 Wyeth Antineoplastic combinations with mtor inhibitor, herceptin, and/or hki-272
US8404697B2 (en) 2005-11-11 2013-03-26 Boehringer Ingelheim International Gmbh Quinazoline derivatives for the treatment of cancer diseases
US8022216B2 (en) 2007-10-17 2011-09-20 Wyeth Llc Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
EP2915532B1 (en) 2008-06-17 2016-10-19 Wyeth LLC Antineoplastic combinations containing hki-272 and vinorelbine
ES2614912T3 (en) 2008-08-04 2017-06-02 Wyeth Llc Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine
EP3000467B1 (en) 2009-04-06 2023-03-01 Wyeth LLC Treatment regimen utilizing neratinib for breast cancer
US9545381B2 (en) 2009-07-06 2017-01-17 Boehringer Ingelheim International Gmbh Process for drying of BIBW2992, of its salts and of solid pharmaceutical formulations comprising this active ingredient
CN102724962B (en) 2009-11-09 2017-05-17 惠氏有限责任公司 Coated drug spheroids and uses thereof for eliminating or reducing conditions such as emesis and diarrhea
CN102838539A (en) * 2011-06-21 2012-12-26 苏州迈泰生物技术有限公司 Quinolinylenamide derivative and its application in preparation of anti-malignant tumor drugs
US9242965B2 (en) * 2013-12-31 2016-01-26 Boehringer Ingelheim International Gmbh Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors
CN105461689B (en) * 2015-05-19 2018-12-04 上海麦步医药科技有限公司 A kind of novel processing step of EGF-R ELISA (EGFR) inhibitor linatinib
CN105085485B (en) * 2015-08-21 2017-08-29 哈尔滨珍宝制药有限公司 A kind of preparation method of HKI-272
US10793548B2 (en) * 2016-04-28 2020-10-06 Jiangsu Hengrui Medicine Co., Ltd. Method for preparing tyrosine kinase inhibitor and derivative thereof
CN105949176B (en) * 2016-06-24 2018-10-26 浙江海正药业股份有限公司 A kind of purification process of linatinib
US20200308141A1 (en) * 2016-06-27 2020-10-01 Pliva Hrvatska D.O.O. Solid state forms of neratinib and salts thereof
CN110357855A (en) * 2018-03-26 2019-10-22 江苏创诺制药有限公司 A kind of linatinib hydrochloride Form and preparation method thereof
CN110357854A (en) * 2018-03-26 2019-10-22 江苏创诺制药有限公司 A kind of preparation method of linatinib
CN111943933B (en) * 2020-09-02 2021-05-28 重庆医科大学 Preparation method of neratinib impurity D
CN111995618B (en) * 2020-09-02 2021-06-11 重庆医科大学 Preparation method of neratinib impurity G

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004066919A2 (en) * 2003-01-21 2004-08-12 Wyeth Synthesis of 4amino-2-butenoyl chlorides and their use in the preparation of 3-cyano quinolines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004066919A2 (en) * 2003-01-21 2004-08-12 Wyeth Synthesis of 4amino-2-butenoyl chlorides and their use in the preparation of 3-cyano quinolines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TSOU H-R ET AL: "Optimization of 6,7-Disubstituted-4-(arylamino)quinoline-3-carbonitr iles as Orally Active, Irreverible Inhibitors of HEGFR-2 Kinase Activity", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 48, 27 January 2005 (2005-01-27), pages 1107 - 1131, XP002414228, ISSN: 0022-2623 *

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Publication number Publication date
WO2010048477A2 (en) 2010-04-29

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