JP2018508583A - キナゾリン誘導体の塩およびその製造方法 - Google Patents
キナゾリン誘導体の塩およびその製造方法 Download PDFInfo
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Abstract
Description
本願は2015年03月20日に中華人民共和国国家知的財産局に出願された出願番号が201510125962.4である中国特許出願に基づく優先権および利益を主張し、当該出願の全文を引用により本願に組み込む。
本発明は、医薬品化学分野に属し、より具体的には、キナゾリン誘導体の塩、その製造方法およびその医薬使用に関する。
ステップ1: 4−クロロ−7−フルオロ−6−ニトロキナゾリン
1H NMR (CDCl3): δ 9.18 (1H, s), 9.05 (1H, d, J = 7.6 Hz), 7.95 (1H, d, J = 10.4)。
1H NMR (CDCl3): δ 6.94−6.82 (4H, m), 6.63−6.61 (1H, m), 6.45−6.41 (1H, m), 4.18 (2H, s), 3.98 (1H, br), 3.87 (3H, s), 3.86 (3H, s)。
1H NMR (CDCl3): δ 8.85 (1H, s), 7.57 (1H, s), 7.35 (1H, s), 7.23−7.19 (2H, m), 7.00−6.96 (1H, m), 6.84−6.78 (2H, m), 5.35 (2H, s), 4.05 (3H, s), 3.88 (3H, s), 3.83 (3H, s)。
1H NMR (DMSO−d6): δ 9.24 (1H, s), 8.33 (1H, s), 8.09−8.08 (1H, m), 7.77−7.74 (1H, m), 7.42−7.40 (1H, m), 7.23 (1H, s), 7.06 (1H, s), 6.85−6.81 (1H, m), 6.10−6.06 (1H, m), 5.66−5.64 (1H, m), 5.32−5.29 (1H, m), 4.41−4.38 (1H, m), 4.09−4.06 (1H, m), 3.93 (3H, s), 3.79−3.78 (1H, m), 3.35−3.34 (1H, m), 2.87−2.84 (1H, m), 2.03−2.01 (2H, m), 1.44−1.41 (2H, m)。
研究方法:体重7.4〜9.4kgのビーグル犬15匹をランダムに5群に分け、5mg/kg体重の式Iで表される化合物およびそのマレイン酸塩、クエン酸塩、蓚酸塩、酢酸塩(式Iで表される化合物の量で換算)のCMC−Na(カルボキシメチルセルロースナトリウム)懸濁液をそれぞれ経口投与し、投与前と投与後(0.25、0.5、1、2、4、6、8、12、24、48時間の時点)に採血し、LC−MS法によって犬血漿サンプルにおける式Iで表される化合物の濃度をそれぞれ測定して生物学的利用能を計算した。
クロマトグラフィー条件は、移動相A:メタノール、移動相B:0.1%(v/v)のギ酸水溶液、アイソクラティック溶離方式: A:B=52:48、流速:0.2mL/min、カラム温度:35℃、クロマトグラフィーカラム:SHIMADZU Shim−pack VP−ODS C18(5.0μm、150mm×2.0mm I.D.島津社製)である。
1.インビトロ酵素学的検出方法
ヒト非小細胞肺癌細胞NCI−H1975、ヒト乳癌細胞系BT474を細胞インキュベータ(37℃、5%CO2)においてRPIM−1640、またはDMEM培地及び10%ウシ胎仔血清(FBS)で培養した。化合物の検出中、底層基質濃度を0.6%としており、細胞を0.3%の低融点寒天で再懸濁した後、1ウェルあたりに10,000個の細胞(100μL)を加えるように96ウェルプレートに播種した。化合物について10mMから始めて3倍段階希釈を行い、各濃度のもの2μLを取って培地98μLに加え、次に、得られた混合物5.3μLを取って細胞培養液(DMSO最終濃度0.1%、v/v)に加え、1週間(7日間)処理後、CellTiter−Blue(R)(Promega)試薬20μLを加えて、37℃で4時間インキュベートし、Envison(Perkin Elmer)において蛍光信号を読み取り、GraphPad Prism 5.0を用いて化合物による細胞増殖阻害のIC50を算出した。
Claims (11)
- 前記式Iで表される化合物とマレイン酸とのモル比が1:0.5〜4である、請求項1に記載の式Iで表される化合物のマレイン酸塩。
- 前記式Iで表される化合物とマレイン酸とのモル比が1:1または1:2である、請求項2に記載の式Iで表される化合物のマレイン酸塩。
- 請求項1〜3のいずれかに記載の式Iで表される化合物のマレイン酸塩の製造方法であって、
式Iで表される化合物の溶液を製造するステップ(1)と、
ステップ(1)で得られた前記式Iで表される化合物の溶液とマレイン酸とを混合するステップ(2)と、
ステップ(2)で得られた反応混合物を噴霧乾燥させて、前記式Iで表される化合物のマレイン酸塩を得るステップ(3)とを含む、
式Iで表される化合物のマレイン酸塩の製造方法。 - 前記式Iで表される化合物とマレイン酸との使用量のモル比は1:1〜20、好ましくは1:1〜15、より好ましくは1:1〜10である、請求項4に記載の製造方法。
- 前記ステップ(1)において、前記式Iで表される化合物を有機溶剤に溶解して前記式Iで表される化合物の溶液を製造し、前記有機溶剤はDMFであることが好ましい、請求項4または5に記載の製造方法。
- 噴霧乾燥前に、前記有機溶剤と相溶する溶剤を加え、前記相溶する溶剤は水であることが好ましい、請求項6に記載の製造方法。
- 請求項1〜3のいずれかに記載の式Iで表される化合物のマレイン酸塩と、薬学的に許容される担体、賦形剤、希釈剤および/または媒体とを含む、医薬組成物。
- 請求項1〜3のいずれかに記載の式Iで表される化合物のマレイン酸塩、または請求項8に記載の医薬組成物の腫瘍治療薬の製造における使用。
- 請求項1〜3のいずれかに記載の式Iで表される化合物のマレイン酸塩、または請求項8に記載の医薬組成物を、必要な対象に投与するステップを含む、腫瘍の治療方法。
- 腫瘍を治療するための、請求項1〜3のいずれかに記載の式Iで表される化合物のマレイン酸塩または請求項8に記載の医薬組成物。
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CN201510125962 | 2015-03-20 | ||
CN201510125962.4 | 2015-03-20 | ||
PCT/CN2016/076693 WO2016150340A1 (zh) | 2015-03-20 | 2016-03-18 | 喹唑啉衍生物的盐及其制备方法 |
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JP6704422B2 JP6704422B2 (ja) | 2020-06-03 |
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US (1) | US10231973B2 (ja) |
EP (1) | EP3272746B1 (ja) |
JP (1) | JP6704422B2 (ja) |
CN (1) | CN107406430B (ja) |
ES (1) | ES2775614T3 (ja) |
HK (1) | HK1244278B (ja) |
RU (1) | RU2720810C2 (ja) |
WO (1) | WO2016150340A1 (ja) |
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JP2022537758A (ja) * | 2019-06-19 | 2022-08-29 | シェンチェン・ジンルイ・ファウンデーション・バイオテック・カンパニー・リミテッド | キナゾリン系化合物の結晶体、塩およびその調製方法 |
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RU2019106531A (ru) * | 2016-08-25 | 2020-09-25 | Чиа Тай Тянцин Фармасьютикал Груп Ко., Лтд. | Кристалл соли производного хиназолина |
CN108069946B (zh) * | 2016-11-08 | 2020-06-05 | 威尚(上海)生物医药有限公司 | 具有穿过血脑屏障能力的取代的喹唑啉化合物 |
CN114401957B (zh) * | 2019-09-04 | 2023-11-21 | 正大天晴药业集团股份有限公司 | 一种喹唑啉衍生物的制备方法及其结晶 |
CN110627731A (zh) * | 2019-10-09 | 2019-12-31 | 贵州大学 | 一类4-氨基喹唑啉接丙烯酰胺类化合物及其制备方法和应用 |
EP4052713A1 (en) * | 2019-11-01 | 2022-09-07 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pharmaceutical composition comprising quinazoline derivative or salt thereof |
WO2021083347A1 (zh) * | 2019-11-01 | 2021-05-06 | 正大天晴药业集团股份有限公司 | 喹唑啉衍生物或其盐、或其药物组合物的用途 |
CN114761010B (zh) * | 2019-11-25 | 2024-04-16 | 正大天晴药业集团股份有限公司 | 喹唑啉衍生物或其盐的联用药物组合物及其用途 |
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TWI377944B (en) | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
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AU2012311184A1 (en) | 2011-09-22 | 2014-03-06 | Pfizer Inc. | Pyrrolopyrimidine and purine derivatives |
KR101272613B1 (ko) | 2011-10-05 | 2013-06-10 | 한미사이언스 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온 염산염의 제조 방법 및 이에 사용되는 중간체 |
CN104513229A (zh) * | 2013-09-28 | 2015-04-15 | 正大天晴药业集团股份有限公司 | 喹唑啉衍生物及其制备方法 |
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JP2022537758A (ja) * | 2019-06-19 | 2022-08-29 | シェンチェン・ジンルイ・ファウンデーション・バイオテック・カンパニー・リミテッド | キナゾリン系化合物の結晶体、塩およびその調製方法 |
JP7350374B2 (ja) | 2019-06-19 | 2023-09-26 | チェンドゥ・ジンルイ・ファウンデーション・バイオテック・カンパニー・リミテッド | キナゾリン系化合物の結晶体、塩およびその調製方法 |
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EP3272746B1 (en) | 2019-12-25 |
RU2017132330A (ru) | 2019-04-22 |
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JP6704422B2 (ja) | 2020-06-03 |
US20180085369A1 (en) | 2018-03-29 |
US10231973B2 (en) | 2019-03-19 |
CN107406430A (zh) | 2017-11-28 |
WO2016150340A1 (zh) | 2016-09-29 |
CN107406430B (zh) | 2019-04-26 |
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ES2775614T3 (es) | 2020-07-27 |
RU2720810C2 (ru) | 2020-05-13 |
EP3272746A4 (en) | 2018-11-07 |
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