JP2018526364A - アンドロゲン受容体阻害剤の結晶型及びその製造方法 - Google Patents
アンドロゲン受容体阻害剤の結晶型及びその製造方法 Download PDFInfo
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- JP2018526364A JP2018526364A JP2018508712A JP2018508712A JP2018526364A JP 2018526364 A JP2018526364 A JP 2018526364A JP 2018508712 A JP2018508712 A JP 2018508712A JP 2018508712 A JP2018508712 A JP 2018508712A JP 2018526364 A JP2018526364 A JP 2018526364A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
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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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- 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
- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
1)式(I)で表される化合物の任意の結晶型または非晶形を適量の有機溶媒に加え、得られた溶液を透明になるまで加熱した後、冷却し、結晶を沈殿させる工程。該有機溶媒はエステル類、ケトン類、ニトリル類及び5以下の炭素原子を有するエーテル類から任意に選択される1種の溶媒またはそれらの混合溶媒である。
2)該結晶を濾過した後、洗浄及び乾燥する工程。
装置型式:Mettler Toledo DSC 1 Stareeシステム
パージガス:窒素
昇温速度:10.0℃/分
温度範囲:40〜250℃
2.X線回折スペクトル
装置型式:Bruker D8 Focus粉末X線回折装置
放射線:単色Cu-Kα線(λ=1.5406)
走査方法:θ/2θ、走査範囲:2〜40°
電圧:40 KV、電流:40 mA
(表1)式(I)の化合物のI型結晶試料の安定性比較
(表2)式(I)の化合物のI型結晶の特別安定性試験
(表3)室温の使用条件下における式(I)の化合物のI型結晶試料の安定性試験
Claims (6)
- Cu-Ka線を用いて得られ、図1に示される2θ角及び面間距離で表される粉末X線回折スペクトルを有し、約8.89 (9.94), 9.97 (8.87), 11.22 (7.88), 14.28 (6.20), 15.17 (5.83), 15.51 (5.71), 16.77 (5.28), 19.91 (4.46), 21.13 (4.20), 22.48 (3.95), 24.06 (3.70)及び26.37 (3.38)に特徴的なピークがあることを特徴とする、式(I)で表される化合物のI型結晶。
- 請求項1に記載の式(I)で表される化合物のI型結晶の製造方法であって、以下の工程を含む方法。
1)式(I)で表される化合物の任意の結晶型または非晶形を適量の有機溶媒に加え、得られた溶液を透明になるまで加熱した後、冷却し、結晶を沈殿させる工程。該有機溶媒はエステル類、ケトン類、ニトリル類及び5以下の炭素原子を有するエーテル類から任意に選択される1種の溶媒またはそれらの混合溶媒である。
2)該結晶を濾過した後、洗浄及び乾燥する工程。 - 前記工程1)の溶媒が酢酸エチル、アセトン、酢酸イソプロピル、テトラヒドロフラン及びアセトニトリルから選択される1種の溶媒、またはアセトン/イソプロピルエーテル、酢酸エチル/n-ヘキサン、酢酸エチル/イソプロピルエーテル及び酢酸エチル/メチルtert-ブチルエーテルから選択される混合溶媒であり、好ましくは酢酸エチル/イソプロピルエーテルであることを特徴とする、請求項2に記載の製造方法。
- 前記混合溶媒の体積比が1:10〜10:1であり、好ましくは1:1である、請求項3に記載の製造方法。
- 請求項1に記載の式(I)で表される化合物のI型結晶及び薬学的に許容される担体を含む医薬組成物。
- アンドロゲン受容体に関連する疾患、好ましくは前立腺癌を治療するための薬剤の製造における、請求項1に記載の式(I)で表される化合物のI型結晶または請求項5に記載の医薬組成物の使用。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510574141 | 2015-09-10 | ||
CN201510574141.9 | 2015-09-10 | ||
CN201610073458 | 2016-02-02 | ||
CN201610073458.9 | 2016-02-02 | ||
PCT/CN2016/096381 WO2017041622A1 (zh) | 2015-09-10 | 2016-08-23 | 一种雄性激素受体抑制剂的结晶形式及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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JP2018526364A true JP2018526364A (ja) | 2018-09-13 |
JP6843116B2 JP6843116B2 (ja) | 2021-03-17 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP2018508712A Active JP6843116B2 (ja) | 2015-09-10 | 2016-08-23 | アンドロゲン受容体阻害剤の結晶型及びその製造方法 |
Country Status (22)
Country | Link |
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US (1) | US10150739B2 (ja) |
EP (1) | EP3348546B1 (ja) |
JP (1) | JP6843116B2 (ja) |
KR (1) | KR20180048939A (ja) |
CN (1) | CN107001284B (ja) |
AU (1) | AU2016318700B2 (ja) |
BR (1) | BR112018003258A2 (ja) |
CA (1) | CA2996674A1 (ja) |
CY (1) | CY1123027T1 (ja) |
DK (1) | DK3348546T3 (ja) |
ES (1) | ES2794568T3 (ja) |
HR (1) | HRP20200852T1 (ja) |
HU (1) | HUE050459T2 (ja) |
LT (1) | LT3348546T (ja) |
MX (1) | MX2018002759A (ja) |
PL (1) | PL3348546T3 (ja) |
PT (1) | PT3348546T (ja) |
RS (1) | RS60448B1 (ja) |
RU (1) | RU2018109121A (ja) |
SI (1) | SI3348546T1 (ja) |
TW (1) | TWI708764B (ja) |
WO (1) | WO2017041622A1 (ja) |
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CN107001284B (zh) | 2015-09-10 | 2019-11-22 | 江苏恒瑞医药股份有限公司 | 一种雄性激素受体抑制剂的结晶形式及其制备方法 |
CN112300076B (zh) * | 2017-12-13 | 2022-10-25 | 江苏恒瑞医药股份有限公司 | 一种雄性激素受体抑制剂的晶型及其制备方法 |
Citations (3)
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WO2014036897A1 (zh) * | 2012-09-04 | 2014-03-13 | 上海恒瑞医药有限公司 | 咪唑啉类衍生物、其制备方法及其在医药上的应用 |
WO2014041487A2 (en) * | 2012-09-11 | 2014-03-20 | Dr. Reddy's Laboratories Limited | Enzalutamide polymorphic forms and its preparation |
CN104356068A (zh) * | 2014-10-30 | 2015-02-18 | 杭州新博思生物医药有限公司 | 恩杂鲁胺新晶型及其制备方法 |
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WO2006028226A1 (ja) * | 2004-09-09 | 2006-03-16 | Chugai Seiyaku Kabushiki Kaisha | 新規イミダゾリジン誘導体およびその用途 |
PT2444085E (pt) | 2005-05-13 | 2015-06-11 | Univ California | Compostos de diaril-hidantoínas como antagonistas do recetor androgénio para tratamento de cancro |
EP2416657A4 (en) * | 2009-04-09 | 2012-09-05 | Medivation Prostate Therapeutics Inc | COMPOUNDS COMPRISING SUBSTITUTED DI-ARYLHYDANTOIDS AND DI-ARYLTHIOHYDANTOINES AND METHODS OF USE THEREOF |
CN107001284B (zh) | 2015-09-10 | 2019-11-22 | 江苏恒瑞医药股份有限公司 | 一种雄性激素受体抑制剂的结晶形式及其制备方法 |
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Patent Citations (3)
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WO2014036897A1 (zh) * | 2012-09-04 | 2014-03-13 | 上海恒瑞医药有限公司 | 咪唑啉类衍生物、其制备方法及其在医药上的应用 |
WO2014041487A2 (en) * | 2012-09-11 | 2014-03-20 | Dr. Reddy's Laboratories Limited | Enzalutamide polymorphic forms and its preparation |
CN104356068A (zh) * | 2014-10-30 | 2015-02-18 | 杭州新博思生物医药有限公司 | 恩杂鲁胺新晶型及其制备方法 |
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Also Published As
Publication number | Publication date |
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RU2018109121A3 (ja) | 2019-12-04 |
SI3348546T1 (sl) | 2020-09-30 |
EP3348546A1 (en) | 2018-07-18 |
RU2018109121A (ru) | 2019-10-10 |
LT3348546T (lt) | 2020-07-27 |
TW201713628A (zh) | 2017-04-16 |
US20180244628A1 (en) | 2018-08-30 |
CA2996674A1 (en) | 2017-03-16 |
US10150739B2 (en) | 2018-12-11 |
KR20180048939A (ko) | 2018-05-10 |
WO2017041622A1 (zh) | 2017-03-16 |
PL3348546T3 (pl) | 2020-09-21 |
BR112018003258A2 (pt) | 2018-09-25 |
PT3348546T (pt) | 2020-05-29 |
MX2018002759A (es) | 2018-08-01 |
HRP20200852T1 (hr) | 2020-08-21 |
CY1123027T1 (el) | 2021-10-29 |
TWI708764B (zh) | 2020-11-01 |
CN107001284B (zh) | 2019-11-22 |
ES2794568T3 (es) | 2020-11-18 |
EP3348546A4 (en) | 2019-03-27 |
AU2016318700A1 (en) | 2018-04-05 |
DK3348546T3 (da) | 2020-07-06 |
HUE050459T2 (hu) | 2020-12-28 |
AU2016318700B2 (en) | 2020-05-07 |
RS60448B1 (sr) | 2020-07-31 |
CN107001284A (zh) | 2017-08-01 |
JP6843116B2 (ja) | 2021-03-17 |
EP3348546B1 (en) | 2020-04-29 |
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