JP6784743B2 - 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 - Google Patents
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 Download PDFInfo
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- JP6784743B2 JP6784743B2 JP2018241276A JP2018241276A JP6784743B2 JP 6784743 B2 JP6784743 B2 JP 6784743B2 JP 2018241276 A JP2018241276 A JP 2018241276A JP 2018241276 A JP2018241276 A JP 2018241276A JP 6784743 B2 JP6784743 B2 JP 6784743B2
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- CPTQHBBUSNGMOV-UHFFFAOYSA-N COc1cc2ncnc(Nc(ccc(Cl)c3Cl)c3F)c2cc1O Chemical compound COc1cc2ncnc(Nc(ccc(Cl)c3Cl)c3F)c2cc1O CPTQHBBUSNGMOV-UHFFFAOYSA-N 0.000 description 1
Classifications
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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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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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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
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- 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)
Description
(i)有機塩基の存在下、式(VII)の化合物をハロゲン化剤との反応に供し、式(VI)の化合物を得る。その後、式(VI)の化合物を、式(VIII)の化合物との反応に供し、式(V)の化合物すなわち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−イル酢酸塩を得る;および
(ii)式(V)の化合物を、プロトン性極性溶媒中で、アンモニア溶液との反応に供する。
1H−NMR(DMSO−d6、300MHz、ppm)δ8.92(s、1H)、8.76(s、1H)、7.69−7.57(m、3H)、4.01(s、3H)、2.38(s、3H)。
1H−NMR(DMSO−d6、300MHz、ppm)δ9.57(br、2H)、8.35(s、1H)、7.68(s、1H)、7.61−7.52(m、2H)、7.21(s、1H)、3.97(s、3H)。
1H−NMR(300MHz、DMSO−d6)δ7.82(d、2H)、7.48(d、2H)、6.80−6.71(m、1H)、6.10−6.03(m、1H)、5.67−5.62(m、1H)、4.76−4.71(m、1H)、3.70−3.68(m、2H)、3.43−3.31(m、2H)、2.42(s、3H)1.73(m、2H)、1.52(m、2H)。
1H−NMR(300MHz、DMSO−d6)δ9.65(bs、1H)、8.40(s、1H)、7.88(s、1H)、7.64−7.56(m、2H)、7.24(s、1H)、6.89−6.80(m、1H)、6.15−6.08(m、1H)、5.70−5.66(m、1H)、4.78(m、1H)、3.94(s、3H)、3.87(m、2H)、3.48(m、2H)、2.03(m、2H)、1.70(m、1H)。
1H−NMR(300MHz、CDCl3)δ7.80(d、2H)、4.76−4.72(m、1H)、3.80(t、2H)、3.64−3.57(m、3H)、3.40(m、1H)、2.77(t、2H)、2.46(s、3H)、1.85−1.70(m、4H)。
1H−NMR(300MHz、DMSO−d6)δ9.65(bs、1H)、8.40(s、1H)、7.88(s、1H)、7.64−7.56(m、2H)、7.24(s、1H)、6.89−6.80(m、1H)、6.15−6.08(m、1H)、5.70−5.66(m、1H)、4.78(m、1H)、3.94(s、3H)、3.87(m、2H)、3.48(m、2H)、2.03(m、2H)、1.70(m、1H)。
Claims (10)
- 前記式(II)の化合物と式(III)の化合物との間の反応のための前記温度が、70℃〜90℃の範囲である、請求項1の方法。
- 前記式(II)の化合物と式(III)の化合物との間の反応が、70℃〜80℃の範囲の温度で進行する、請求項1の方法。
- 前記不活性の非プロトン性極性溶媒が、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリジン−2−オン、ジメチルスルホキシドおよびこれらの混合物からなる群から選択されることを特徴とする、請求項1の方法。
- 前記塩基が、炭酸水素ナトリウム、炭酸カリウム、炭酸セシウムおよびこれらの混合物からなる群から選択されるアルカリ金属炭酸塩であることを特徴とする、請求項1の方法。
- 前記塩基が、式(IX)の化合物またはそれらの塩の1モル当量に対して、3〜5モル当量の量であることを特徴とする、請求項6の方法。
- 前記アミドカップリング剤が、式(IX)の化合物またはそれらの塩の1モル当量に対して、3〜5モル当量の量であることを特徴とする、請求項6の方法。
- 前記式(IX)の化合物またはその塩と式(X)の化合物との間の反応が、−30℃〜30℃の範囲の温度で実施される、請求項6の方法。
- 前記式(IX)の化合物またはその塩と式(X)の化合物との間の反応が、室温で実施される、請求項6の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR10-2013-0009282 | 2013-01-28 | ||
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 |
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JP2015555109A Division 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 |
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JP2020068550A Division JP7051929B2 (ja) | 2013-01-28 | 2020-04-06 | 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 |
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JP2019065034A JP2019065034A (ja) | 2019-04-25 |
JP6784743B2 true JP6784743B2 (ja) | 2020-11-11 |
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JP2015555109A Active 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 |
JP2018241276A Active JP6784743B2 (ja) | 2013-01-28 | 2018-12-25 | 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 |
JP2020068550A Active JP7051929B2 (ja) | 2013-01-28 | 2020-04-06 | 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 |
JP2022056875A Active JP7377307B2 (ja) | 2013-01-28 | 2022-03-30 | 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 |
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JP2015555109A Active 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 |
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JP2020068550A Active JP7051929B2 (ja) | 2013-01-28 | 2020-04-06 | 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 |
JP2022056875A Active JP7377307B2 (ja) | 2013-01-28 | 2022-03-30 | 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 |
Country Status (17)
Country | Link |
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US (1) | US9518043B2 (ja) |
EP (1) | EP2948441B1 (ja) |
JP (4) | JP6461011B2 (ja) |
KR (1) | KR20140096571A (ja) |
CN (1) | CN104981467B (ja) |
AU (1) | AU2014210494B2 (ja) |
BR (1) | BR112015017597B1 (ja) |
CA (2) | CA2898433C (ja) |
DK (1) | DK2948441T3 (ja) |
ES (1) | ES2662863T3 (ja) |
IL (2) | IL240197B (ja) |
MX (1) | MX362763B (ja) |
NO (1) | NO2948441T3 (ja) |
PH (2) | PH12015501636B1 (ja) |
RU (2) | RU2671843C2 (ja) |
WO (1) | WO2014116070A1 (ja) |
ZA (1) | ZA201506241B (ja) |
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US20210221792A1 (en) * | 2020-01-16 | 2021-07-22 | Hanmi Pharm Co., Ltd. | Convergent synthesis of poziotinib derivative |
US20220064145A1 (en) * | 2020-08-28 | 2022-03-03 | Hanmi Science Co., Ltd. | Synthesis of poziotinib derivative |
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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2013
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