JP6929769B2 - 6−アリールアミノピリドンカルボキサミド化合物の結晶、およびその製造方法 - Google Patents
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- 239000000203 mixture Substances 0.000 claims description 20
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
室温において、化合物6−(2−クロロ−4−ヨードアニリノ)− N −(2−ビニルオキシエトキシ)−5−メチル−4−オキソ−4,5−ジヒドロフロ[3,2−c]ピリジン−7−アミド5gを秤量し、無水テトラヒドロフラン50mLに溶解させ、反応温度を−10℃まで低下し、6N HCl約20mLをゆっくりと滴下し、滴下終了後、5〜10℃に維持して約2時間反応した。反応終了後、反応液を氷水に流し込み、酢酸エチルで抽出し、有機相溶媒を蒸留除去し、得られた固体をエタノールでパルプ化し、ろ過して淡黄色の固体を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMSO 5mLを加え、約110℃に昇温し、清澄化し、自然冷却させ、温度45℃まで低下してから水25mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMF 10mLを加え、約100℃まで昇温し、清澄化し、自然冷却させ、温度45℃まで低下してからイソプロパノール30mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMSO 10mLを加え、約100℃まで昇温し、清澄化し、自然冷却させ、温度50℃まで低下してからエタノール15mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMSO 10mLを加え、約120℃まで昇温し、清澄化し、自然冷却させ、温度50℃まで低下してからメタノール20mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMSO 15mLを加え、約110℃まで昇温し、清澄化し、自然冷却させ、温度60℃まで低下してから水15mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMF 20mLを加え、約90℃まで昇温し、清澄化し、自然冷却させ、温度30℃まで低下してからエタノール5mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
実施例1で得られた式(I)で示される化合物の粗製品10gを取り、DMF 25mLを加え、約80℃まで昇温し、清澄化し、自然冷却させ、温度35℃まで低下してからメタノール12.5mLを加え、撹拌を続けて多くのオフホワイト固体を析出し、ろ過し、50℃で真空乾燥して白色またはオフホワイト結晶を得た。
中国薬局方2010年版2部の付録V Dを参照し、高速液体クロマトグラフィにより式(I)で示される化合物の結晶純度を測定する。オクタデシルシラン結合シリカゲルを充填剤として用い[カラム:Eclipse XDB−C18(4.6×150mm、5μm)または同等の性能を有するカラムを推奨する]、水(0.01%トリフルオロ酢酸溶液)を移動相Aとし、アセトニトリル(0.01%トリフルオロ酢酸溶液)を移動相Bとし、流速は1.0mL/分間であり、表1により線形勾配溶離を行い、カラム温度は30℃で、検出波長は244nmである。理論段数は、式(I)で示される化合物によって計算して2000未満である。
中国薬局方2010年版(2部)の付録XIX Cにおける原料薬影響因素試験の方法を参照し、実施例4で製造された式(I)で示される化合物の結晶を、それぞれ高温試験(40℃±2℃、相対湿度75%±5%)および強光照射試験(4500 lx ± 500 lx)を施した。考察期間は10日であり、それぞれ第0日および第10日にサンプリングして不純物の合計量を検出し、その安定性を考察し、試験結果を表2に示す。
Claims (10)
- X線粉末回折スペクトルは、2θ値で表示する7.86°、9.32°、13.25°、15.06°、19.09°、21.80°、22.46°、22.81°、23.87°、26.00°、28.12°、28.59°のところに回折ピークを持っている、請求項1に記載の結晶。
- X線粉末回折スペクトルは、2θ値で表示する7.86°、9.32°、13.25°、15.06°、17.89°、19.09°、20.73°、21.80°、22.46°、22.81°、23.87°、24.55°、26.00°、27.29°、28.12°、28.59°、29.32°、30.15°のところに回折ピークを持っている、請求項2に記載の結晶。
- 請求項1〜3のいずれか1項に記載の式(I)で示される化合物の結晶が結晶組成物の重量50%以上を占める、結晶組成物。
- 請求項1〜3のいずれか1項に記載の式(I)で示される化合物の結晶が結晶組成物の重量80%以上を占める、結晶組成物。
- 請求項1〜3のいずれか1項に記載の式(I)で示される化合物の結晶が結晶組成物の重量90%以上を占める、結晶組成物。
- 請求項1〜3のいずれか1項に記載の式(I)で示される化合物の結晶が結晶組成物の重量95%以上を占める、結晶組成物。
- 治療有効量の請求項1〜7のいずれか1項に記載の式(I)で示される化合物の結晶または結晶組成物を含む、医薬組成物。
- 請求項1〜8のいずれか1項に記載の式(I)で示される化合物の結晶、結晶組成物または医薬組成物の、MEK媒介性の病症または疾患を治療または予防するための医薬組成物の製造における使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201410383541.7A CN105315291B (zh) | 2014-08-05 | 2014-08-05 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
CN201410383541.7 | 2014-08-05 | ||
PCT/CN2015/086118 WO2016019867A1 (zh) | 2014-08-05 | 2015-08-05 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
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JP2017523210A JP2017523210A (ja) | 2017-08-17 |
JP6929769B2 true JP6929769B2 (ja) | 2021-09-01 |
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US (1) | US10023582B2 (ja) |
EP (1) | EP3178821B1 (ja) |
JP (1) | JP6929769B2 (ja) |
KR (1) | KR20170032476A (ja) |
CN (2) | CN105315291B (ja) |
AU (1) | AU2015299546B2 (ja) |
CA (1) | CA2956404A1 (ja) |
WO (1) | WO2016019867A1 (ja) |
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CN105315291B (zh) * | 2014-08-05 | 2019-02-01 | 正大天晴药业集团股份有限公司 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
WO2016188472A1 (zh) | 2015-05-28 | 2016-12-01 | 正大天晴药业集团股份有限公司 | Mek抑制剂的药物组合物及其制备方法 |
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CN102020651B (zh) * | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
US20120238599A1 (en) * | 2011-03-17 | 2012-09-20 | Chemizon, A Division Of Optomagic Co., Ltd. | Heterocyclic compounds as mek inhibitors |
CN105315291B (zh) * | 2014-08-05 | 2019-02-01 | 正大天晴药业集团股份有限公司 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
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2015
- 2015-08-05 US US15/329,197 patent/US10023582B2/en active Active
- 2015-08-05 AU AU2015299546A patent/AU2015299546B2/en active Active
- 2015-08-05 EP EP15830563.1A patent/EP3178821B1/en active Active
- 2015-08-05 WO PCT/CN2015/086118 patent/WO2016019867A1/zh active Application Filing
- 2015-08-05 CA CA2956404A patent/CA2956404A1/en not_active Abandoned
- 2015-08-05 KR KR1020177006090A patent/KR20170032476A/ko not_active Application Discontinuation
- 2015-08-05 CN CN201580026821.5A patent/CN106661040B/zh active Active
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EP3178821A1 (en) | 2017-06-14 |
CN106661040A (zh) | 2017-05-10 |
AU2015299546A1 (en) | 2017-03-16 |
KR20170032476A (ko) | 2017-03-22 |
EP3178821A4 (en) | 2018-01-03 |
JP2017523210A (ja) | 2017-08-17 |
CN106661040B (zh) | 2019-04-26 |
EP3178821B1 (en) | 2020-05-06 |
AU2015299546B2 (en) | 2019-07-11 |
CN105315291A (zh) | 2016-02-10 |
CN105315291B (zh) | 2019-02-01 |
CA2956404A1 (en) | 2016-02-11 |
US20170217979A1 (en) | 2017-08-03 |
WO2016019867A1 (zh) | 2016-02-11 |
US10023582B2 (en) | 2018-07-17 |
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