WO2014116070A1 - Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one - Google Patents

Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one Download PDF

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Publication number
WO2014116070A1
WO2014116070A1 PCT/KR2014/000752 KR2014000752W WO2014116070A1 WO 2014116070 A1 WO2014116070 A1 WO 2014116070A1 KR 2014000752 W KR2014000752 W KR 2014000752W WO 2014116070 A1 WO2014116070 A1 WO 2014116070A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
mixture
reaction
base
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/KR2014/000752
Other languages
English (en)
French (fr)
Inventor
Keuk Chan Bang
Jae Hyuk Jung
Young Ho Moon
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.)
Hanmi Pharmaceutical Co Ltd
Hanmi Pharmaceutical Industries Co Ltd
Original Assignee
Hanmi Pharmaceutical Co Ltd
Hanmi Pharmaceutical Industries Co 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
Priority to AU2014210494A priority Critical patent/AU2014210494B2/en
Priority to CN201480005827.XA priority patent/CN104981467B/zh
Priority to MX2015009232A priority patent/MX362763B/es
Priority to CA2898433A priority patent/CA2898433C/en
Priority to ES14743689.3T priority patent/ES2662863T3/es
Priority to MX2019000647A priority patent/MX388687B/es
Priority to NO14743689A priority patent/NO2948441T3/no
Priority to DK14743689.3T priority patent/DK2948441T3/en
Priority to US14/763,295 priority patent/US9518043B2/en
Priority to RU2015129994A priority patent/RU2671843C2/ru
Priority to BR112015017597-0A priority patent/BR112015017597B1/pt
Application filed by Hanmi Pharmaceutical Co Ltd, Hanmi Pharmaceutical Industries Co Ltd filed Critical Hanmi Pharmaceutical Co Ltd
Priority to EP14743689.3A priority patent/EP2948441B1/en
Priority to JP2015555109A priority patent/JP6461011B2/ja
Publication of WO2014116070A1 publication Critical patent/WO2014116070A1/en
Priority to PH12015501636A priority patent/PH12015501636B1/en
Priority to IL240197A priority patent/IL240197B/en
Anticipated expiration legal-status Critical
Priority to ZA2015/06241A priority patent/ZA201506241B/en
Priority to IL267303A priority patent/IL267303B/en
Priority to PH12019501676A priority patent/PH12019501676A1/en
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • 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

Definitions

  • the base used in the above reaction is alkali metal carbonates such as sodium bicarbonate, potassium carbonate, cesium carbonate and a mixture thereof.
  • the base is used in an amount of 1 to 5 mole equivalents based on 1 mole equivalent of the compound of formula (II).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/KR2014/000752 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one Ceased WO2014116070A1 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BR112015017597-0A BR112015017597B1 (pt) 2013-01-28 2014-01-27 Método para preparação de 1-(4-(4-(3,4-dicloro-2- fluorofenilamino)-7-metoxiquinazolin-6- iloxi)piperidin-1-il)prop-2-en-1-ona
MX2015009232A MX362763B (es) 2013-01-28 2014-01-27 Método para preparar 1-(4-(4-(3,4-dicloro-2-fluorofenilamino)-7-me toxiquinazolin-6-iloxi)piperidin-1-il)prop-2-en-1-ona.
CA2898433A CA2898433C (en) 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
ES14743689.3T ES2662863T3 (es) 2013-01-28 2014-01-27 Método para preparar 1-(4-(4-(3,4-dicloro-2-fluorofenilamino)-7-metoxiquinazolin-6-iloxi)piperidin-1-il)prop-2-en-1-ona
MX2019000647A MX388687B (es) 2013-01-28 2014-01-27 Metodo para preparar 1-(4-(4-(3,4-dicloro-2- fluorofenilamino)-7-metoxiquinazolin-6-iloxi)piperidin-1- il)prop-2-en-1-ona
NO14743689A NO2948441T3 (enExample) 2013-01-28 2014-01-27
DK14743689.3T DK2948441T3 (en) 2013-01-28 2014-01-27 PROCEDURE FOR PREPARING 1- (4- (4- (3,4-DICHLOR-2-FLUORPHENYLAMINO) -7-METHOXYQUINAZOLIN-6-YLOXY) PIPERIDIN-1-YL) PROP-2-EN-1-ON
US14/763,295 US9518043B2 (en) 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yi)prop-2-en-1-one
EP14743689.3A EP2948441B1 (en) 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
AU2014210494A AU2014210494B2 (en) 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
CN201480005827.XA CN104981467B (zh) 2013-01-28 2014-01-27 制备l‑(4‑(4‑(3,4‑二氯‑2‑氟苯基氨基)‑7‑甲氧基喹唑啉‑6‑基氧)哌啶‑l‑基)丙‑2‑烯‑l‑酮的方法
RU2015129994A RU2671843C2 (ru) 2013-01-28 2014-01-27 Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она
JP2015555109A JP6461011B2 (ja) 2013-01-28 2014-01-27 １−（４−（４−（３，４−ジクロロ−２−フルオロフェニルアミノ）−７−メトキシキナゾリン−６−イルオキシ）ピペリジン−１−イル）プロパ−２−エン−１−オンの製造方法
PH12015501636A PH12015501636B1 (en) 2013-01-28 2015-07-23 Method for preparing 1-(4-(4-(3,4 - dichloro -2- fluorophenylamino)-7- methoxyquinazolin -6- yloxy) piperidin -1-yl) prop-2-en-1-one
IL240197A IL240197B (en) 2013-01-28 2015-07-28 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
ZA2015/06241A ZA201506241B (en) 2013-01-28 2015-08-26 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
IL267303A IL267303B (en) 2013-01-28 2019-06-12 Method for the production of -7-(3,4-dichloro-2-fluorophenylamino)-4)-4)-1 methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one
PH12019501676A PH12019501676A1 (en) 2013-01-28 2019-07-22 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130009282A KR20140096571A (ko) 2013-01-28 2013-01-28 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법
KR10-2013-0009282 2013-01-28

Publications (1)

Publication Number Publication Date
WO2014116070A1 true WO2014116070A1 (en) 2014-07-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/000752 Ceased WO2014116070A1 (en) 2013-01-28 2014-01-27 Method for preparing 1-(4-(4-(3,4-dichloro-2-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)piperidin-1-yl)prop-2-en-1-one

Country Status (17)

Country Link
US (1) US9518043B2 (enExample)
EP (1) EP2948441B1 (enExample)
JP (4) JP6461011B2 (enExample)
KR (1) KR20140096571A (enExample)
CN (1) CN104981467B (enExample)
AU (1) AU2014210494B2 (enExample)
BR (1) BR112015017597B1 (enExample)
CA (2) CA2898433C (enExample)
DK (1) DK2948441T3 (enExample)
ES (1) ES2662863T3 (enExample)
IL (2) IL240197B (enExample)
MX (2) MX362763B (enExample)
NO (1) NO2948441T3 (enExample)
PH (2) PH12015501636B1 (enExample)
RU (2) RU2018137882A (enExample)
WO (1) WO2014116070A1 (enExample)
ZA (1) ZA201506241B (enExample)

Cited By (4)

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Publication number Priority date Publication date Assignee Title
JP2018522928A (ja) * 2015-08-11 2018-08-16 プリンシピア バイオファーマ インコーポレイテッド Ｆｇｆｒ阻害剤の合成方法
WO2020130125A1 (ja) 2018-12-21 2020-06-25 第一三共株式会社 抗体－薬物コンジュゲートとキナーゼ阻害剤の組み合わせ
US20210221792A1 (en) * 2020-01-16 2021-07-22 Hanmi Pharm Co., Ltd. Convergent synthesis of poziotinib derivative
WO2022043923A1 (en) * 2020-08-28 2022-03-03 Hanmi Science Co., Ltd. Synthesis of poziotinib derivative

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KR20140096571A (ko) * 2013-01-28 2014-08-06 한미약품 주식회사 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법
CN117567466B (zh) * 2024-01-16 2024-04-16 成都金瑞基业生物科技有限公司 一种喹唑啉衍生物的制备方法

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Publication number Priority date Publication date Assignee Title
JP2018522928A (ja) * 2015-08-11 2018-08-16 プリンシピア バイオファーマ インコーポレイテッド Ｆｇｆｒ阻害剤の合成方法
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Also Published As

Publication number Publication date
IL267303A (en) 2019-08-29
JP2020125306A (ja) 2020-08-20
IL267303B (en) 2021-01-31
EP2948441B1 (en) 2017-12-27
ES2662863T3 (es) 2018-04-10
JP7377307B2 (ja) 2023-11-09
DK2948441T3 (en) 2018-03-26
US20150344458A1 (en) 2015-12-03
JP2016505068A (ja) 2016-02-18
JP2022088570A (ja) 2022-06-14
CN104981467B (zh) 2017-10-24
US9518043B2 (en) 2016-12-13
RU2671843C2 (ru) 2018-11-07
NO2948441T3 (enExample) 2018-05-26
JP7051929B2 (ja) 2022-04-11
EP2948441A1 (en) 2015-12-02
RU2018137882A (ru) 2019-03-21
MX2015009232A (es) 2016-04-28
CA2898433A1 (en) 2014-07-31
PH12019501676A1 (en) 2021-02-22
KR20140096571A (ko) 2014-08-06
AU2014210494A1 (en) 2015-08-06
JP2019065034A (ja) 2019-04-25
EP2948441A4 (en) 2016-07-06
MX388687B (es) 2025-03-20
ZA201506241B (en) 2017-06-28
JP6784743B2 (ja) 2020-11-11
PH12015501636A1 (en) 2015-10-19
AU2014210494B2 (en) 2017-09-14
CA3129936A1 (en) 2014-07-31
BR112015017597B1 (pt) 2022-11-16
PH12015501636B1 (en) 2015-10-19
JP6461011B2 (ja) 2019-01-30
IL240197B (en) 2019-06-30
RU2015129994A (ru) 2017-03-10
CA2898433C (en) 2021-11-02
BR112015017597A2 (enExample) 2017-08-15
CN104981467A (zh) 2015-10-14
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IL240197A0 (en) 2015-09-24

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