WO2007138613A3 - A process for synthesis of [6,7-bis-(2-methoxyethoxy)-quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride - Google Patents

A process for synthesis of [6,7-bis-(2-methoxyethoxy)-quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride Download PDF

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Publication number
WO2007138613A3
WO2007138613A3 PCT/IN2007/000101 IN2007000101W WO2007138613A3 WO 2007138613 A3 WO2007138613 A3 WO 2007138613A3 IN 2007000101 W IN2007000101 W IN 2007000101W WO 2007138613 A3 WO2007138613 A3 WO 2007138613A3
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WO
WIPO (PCT)
Prior art keywords
bis
methoxyethoxy
ethynylphenyl
quinazolin
hydrochloride
Prior art date
Application number
PCT/IN2007/000101
Other languages
French (fr)
Other versions
WO2007138613A2 (en
Inventor
Venkateshappa Chandregowda
Gudapati Venkateswara Rao
Anil Kumar Kush
Goukanapalli Chandrasekara Reddy
Original Assignee
Vittal Mallya Scient Res Found
Venkateshappa Chandregowda
Gudapati Venkateswara Rao
Anil Kumar Kush
Reddy Goukanapalli Chandraseka
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 Vittal Mallya Scient Res Found, Venkateshappa Chandregowda, Gudapati Venkateswara Rao, Anil Kumar Kush, Reddy Goukanapalli Chandraseka filed Critical Vittal Mallya Scient Res Found
Publication of WO2007138613A2 publication Critical patent/WO2007138613A2/en
Publication of WO2007138613A3 publication Critical patent/WO2007138613A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms

Abstract

The present invention provides a process for synthesizing [6,7-bis(2-methoxyethoxy)quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride (Erlitinib Hydrochloride) having the formula (I) comprising reacting 3,4-dihydroxy benzaldehyde with bromo derivative of ethyl methyl ether to obtain 3,4-bis(2-methoxyethoxy)benzaldehyde having formula (III). This is converted to give 3,4- bis (2-methoxyethoxy)-benzonitrile which on furthur nitration we obtain 4,5- bis (2-methoxyethoxy)-2-nitrobenzonitrile which on nitro reduction we get 2-amino-4,5-bis(2-methoxyethoxy)benzonitrile. Formylation of this compound yields N'-[2-cyano-4,5-bis(2methoxyethoxy)phenyl]-N,N-dimethylformamidine. Coupling of this formamidine with 3-ethynyl aniline gives erlotinib free base. On furthur treatment of this free base with methanolic/ethanolic hydrochloric acid gives us erlotinib hydrochloride.
PCT/IN2007/000101 2006-05-25 2007-03-12 A process for synthesis of [6,7-bis-(2-methoxyethoxy)-quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride WO2007138613A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN904/CHE/2006 2006-05-25
IN904CH2006 2006-05-25

Publications (2)

Publication Number Publication Date
WO2007138613A2 WO2007138613A2 (en) 2007-12-06
WO2007138613A3 true WO2007138613A3 (en) 2009-04-16

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PCT/IN2007/000101 WO2007138613A2 (en) 2006-05-25 2007-03-12 A process for synthesis of [6,7-bis-(2-methoxyethoxy)-quinazolin-4-yl]-(3-ethynylphenyl)amine hydrochloride

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WO (1) WO2007138613A2 (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2170844B1 (en) * 2007-02-21 2016-05-04 Natco Pharma Limited Novel polymorphs of erlotinib hydrochloride and method of preparation
ES2492645T3 (en) * 2007-07-11 2014-09-10 Hetero Drugs Limited An improved procedure for the preparation of erlotinib hydrochloride
CN101463013B (en) * 2007-12-21 2011-06-22 上海百灵医药科技有限公司 Preparation of erlotinid hydrochloride
US8440823B2 (en) 2009-03-26 2013-05-14 Ranbaxy Laboratories Limited Process for the preparation of erlotinib or its pharmaceutically acceptable salts thereof
WO2011058525A2 (en) 2009-11-12 2011-05-19 Ranbaxy Laboratories Limited Processes for the preparation of erlotinib hydrochloride form a and erlotinib hydrochloride form b
CN102557977B (en) * 2010-12-20 2014-07-30 浙江海正药业股份有限公司 Synthesis intermediate of erlotinib and preparation method thereof
WO2012150606A2 (en) 2011-05-03 2012-11-08 Cadila Healthcare Limited A process for preparing stable polymophic form of erlotinib hydrochloride
WO2013064128A1 (en) * 2011-10-31 2013-05-10 浙江贝达药业有限公司 Methods of preparing icotinib and icotinib hydrochloride, and intermediates thereof
CN103360369A (en) * 2012-03-27 2013-10-23 上海铂力生物科技有限公司 Erlotinib, and preparation method of new intermediate of erlotinib
CN103539702B (en) * 2012-07-12 2016-03-30 陕西师范大学 The novel preparation method of N '-aryl-N, N-dimethyl carbonamidine
CN102887835A (en) * 2012-07-24 2013-01-23 连云港盛和生物科技有限公司 Method for synthesizing 2-amino-4,5-bis-(2-methoxyethoxy)cyanophenyl
CN102887862A (en) * 2012-07-24 2013-01-23 连云港盛和生物科技有限公司 Method for synthesizing erlotinib
JP5955396B2 (en) * 2012-12-28 2016-07-20 ベータ ファーマシューティカルズ カンパニー リミテッド Method for producing icotinib, icotinib hydrochloride, and intermediates thereof
CN103933569B (en) * 2013-01-22 2017-01-11 复旦大学 Anti-lung cancer pharmaceutical composition, its application, pill case and package
WO2014118737A1 (en) 2013-01-31 2014-08-07 Ranbaxy Laboratories Limited Erlotinib salts
TWI612039B (en) * 2013-04-03 2018-01-21 Betta Pharmaceuticals Co Ltd Preparation method of ectinib and ectinib hydrochloride and intermediate thereof
CN103333124B (en) * 2013-05-28 2015-03-25 埃斯特维华义制药有限公司 Preparation method of hydrochloric acid erlotinib crystal form F
LV14953B (en) * 2013-08-14 2015-04-20 Latvijas Organiskās Sintēzes Institūts Preparation method of erlotinib
CN103396371B (en) * 2013-08-26 2015-12-02 南京优科生物医药研究有限公司 A kind of preparation method of Erlotinib hydrochloride crystal form A
CN103641786A (en) * 2013-12-26 2014-03-19 山东博迈康药物研究有限公司 Preparation method of erlotinib hydrochloride crystal form A
CN104059026B (en) * 2014-06-20 2016-03-30 凯莱英医药集团（天津）股份有限公司 A kind of method preparing erlotinid hydrochloride
CA2908441A1 (en) 2014-10-28 2016-04-28 Cerbios-Pharma Sa Process for the preparation of erlotinib
CN106749047A (en) * 2015-11-24 2017-05-31 重庆圣华曦药业股份有限公司 A kind of method for preparing Tarceva
CN108358798A (en) * 2018-02-12 2018-08-03 黑龙江鑫创生物科技开发有限公司 A kind of method of micro passage reaction synthesis Tarceva intermediate

Citations (2)

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US5883102A (en) * 1995-10-17 1999-03-16 Astra Pharmaceuticals Limited Pharmaceutically active compounds

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO1996030347A1 (en) * 1995-03-30 1996-10-03 Pfizer Inc. Quinazoline derivatives
US5883102A (en) * 1995-10-17 1999-03-16 Astra Pharmaceuticals Limited Pharmaceutically active compounds

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