WO2018072300A1 - 一种制备氘代咪唑二酮类化合物的方法 - Google Patents
一种制备氘代咪唑二酮类化合物的方法 Download PDFInfo
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- WO2018072300A1 WO2018072300A1 PCT/CN2016/110978 CN2016110978W WO2018072300A1 WO 2018072300 A1 WO2018072300 A1 WO 2018072300A1 CN 2016110978 W CN2016110978 W CN 2016110978W WO 2018072300 A1 WO2018072300 A1 WO 2018072300A1
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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
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Abstract
Description
DMSO | 二甲基亚砜 |
IPAc | 乙酸异丙酯 |
DMF | N,N-二甲基甲酰胺 |
EA | 乙酸乙酯 |
THF | 四氢呋喃 |
DMAA | N,N-二甲基甘氨酸 |
HATU | 2-(7-氧化苯并三氮唑)-N,N,N',N'-四甲基脲六氟磷酸酯 |
CDI | N,N’-羰基二咪唑 |
Claims (20)
- 根据权利要求1所述的方法,其特征在于:R1和R2均为甲基。
- 根据权利要求1或2所述的方法,其特征在于:R3、R4、R5均为氘。
- 根据权利要求1-3任一项所述的方法,其特征在于:R为甲基。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(1)中,反应的温度为40~120℃。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(2)中,反应的温度为-10~60℃。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(3)中,反应的温度为40~90℃
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(4)中,反应的温度为-10~70℃
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(5)中,反应的温度为-10~40℃
- 根据权利要求1-4任一项所述的方法,其特征在于:所述步骤(3)的环合中,溶剂为二甲基亚砜或者二甲基亚砜与乙酸异丙酯组成的混合溶剂,其中二甲基亚砜与乙酸异丙酯的体积比为50:1~1:10。
- 根据权利要求10所述的方法,其特征在于:所述二甲基亚砜与乙酸异丙酯的体积比为1:2。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(4)中,所述反应是在碱的存在下进行的,所述碱选自碱金属的氢氧化物。
- 根据权利要求12所述的方法,其特征在于:所述碱的氢氧化物选自LiOH、KOH或NaOH,优选LiOH。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(5)中,所述酰胺缩合反应是在缩合剂的存在下进行的,所述缩合剂选自氯甲酸异丙酯、N,N’-羰基二咪唑或HATU。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(1)中,所述取代反应是在碱性环境下,以Cu、CuI和N,N-二甲基甘氨酸为催化剂进行的。
- 根据权利要求1-4任一项所述的方法,其特征在于:步骤(2)中,所述羧基甲酯化的试剂为碘甲烷。
- 根据权利要求17所述的方法,其特征在于:R9和R10均为甲基。
- 根据权利要求17或18所述的方法,其特征在于:R6、R7、R8均为氘。
- 根据权利要求17-19任一项所述的方法,其特征在于:R’为甲基。
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
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FIEP16919556.7T FI3527556T3 (fi) | 2016-10-17 | 2016-12-20 | Menetelmä deuteroidun imidatsolidiketoniyhdisteen valmistamiseksi |
JP2019520547A JP7241682B2 (ja) | 2016-10-17 | 2016-12-20 | 重水素化イミダゾリジンジオン系化合物を調製する方法 |
PL16919556.7T PL3527556T3 (pl) | 2016-10-17 | 2016-12-20 | Sposób wytwarzania deuterowanych związków imidazolodiketonowych |
US16/342,912 US20200087261A1 (en) | 2016-10-17 | 2016-12-20 | Method for preparing deuterated imidazole diketone compound |
DK16919556.7T DK3527556T3 (da) | 2016-10-17 | 2016-12-20 | Fremgangsmåde til fremstilling af deutereret imidazoldiketonforbindelse |
EP16919556.7A EP3527556B1 (en) | 2016-10-17 | 2016-12-20 | Method for preparing deuterated imidazole diketone compound |
CA3040785A CA3040785C (en) | 2016-10-17 | 2016-12-20 | A method for the preparation of deuterated imidazole diketone compounds |
AU2016426847A AU2016426847B2 (en) | 2016-10-17 | 2016-12-20 | Method for preparing deuterated imidazole diketone compound |
ES16919556T ES2943011T3 (es) | 2016-10-17 | 2016-12-20 | Procedimiento de preparación del compuesto imidazol dicetona deuterado |
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CN201610901502.0 | 2016-10-17 | ||
CN201610901502.0A CN107954936B (zh) | 2016-10-17 | 2016-10-17 | 一种制备氘代咪唑二酮类化合物的方法 |
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US (1) | US20200087261A1 (zh) |
EP (1) | EP3527556B1 (zh) |
JP (1) | JP7241682B2 (zh) |
CN (1) | CN107954936B (zh) |
AU (1) | AU2016426847B2 (zh) |
CA (1) | CA3040785C (zh) |
DK (1) | DK3527556T3 (zh) |
ES (1) | ES2943011T3 (zh) |
FI (1) | FI3527556T3 (zh) |
HU (1) | HUE061557T2 (zh) |
PL (1) | PL3527556T3 (zh) |
PT (1) | PT3527556T (zh) |
TW (1) | TWI728077B (zh) |
WO (1) | WO2018072300A1 (zh) |
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CN109180511A (zh) * | 2018-08-22 | 2019-01-11 | 辽宁东科药业有限公司 | 一种盐酸丁卡因的制备方法 |
CN114621109B (zh) * | 2020-12-14 | 2024-04-26 | 成都苑东生物制药股份有限公司 | 一种阿帕他胺的合成方法及其中间体 |
CN113698310B (zh) * | 2021-08-20 | 2023-03-17 | 江西金丰药业有限公司 | 一种恩杂鲁胺双酯中间体的制备方法 |
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CN101817787A (zh) * | 2009-02-26 | 2010-09-01 | 童友之 | 抗前列腺癌的雄性激素受体拮抗剂 |
CN103159680A (zh) * | 2011-12-14 | 2013-06-19 | 爱美尼迪药物有限公司 | 咪唑二酮类化合物及其用途 |
EP2656841A1 (en) * | 2006-03-27 | 2013-10-30 | The Regents of The University of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
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RU2548918C2 (ru) * | 2009-02-24 | 2015-04-20 | Медивэйшн Простейт Терапьютикс, Инк. | Специфические соединения диарилгидантоина и диарилтиогидантоина |
BR112012021406B1 (pt) * | 2010-02-24 | 2021-08-10 | Medivation Prostate Therapeutics Llc | Processos para a síntese dos compostos de diariltioidantoína e diarilidantoína |
US9708289B2 (en) * | 2013-05-29 | 2017-07-18 | Hinova Pharmaceuticals Inc. | Imidazole diketone compound and use thereof |
CN104341352A (zh) * | 2013-08-09 | 2015-02-11 | 南京衡杰生物科技有限公司 | 作为雄激素受体拮抗剂的二芳基乙内酰脲化合物及其应用 |
CN104803918B (zh) * | 2014-01-26 | 2017-11-10 | 上海医药工业研究院 | 恩杂鲁胺的制备方法 |
CN104016924B (zh) * | 2014-06-16 | 2016-04-13 | 上海鼎雅药物化学科技有限公司 | 一种“一锅法”合成恩杂鲁胺的方法 |
RU2557235C1 (ru) * | 2014-07-08 | 2015-07-20 | Александр Васильевич Иващенко | Замещенные 2-тиоксо-имидазолидин-4-оны и их спироаналоги, противораковый активный компонент, фармацевтическая композиция, лекарственный препарат, способ лечения рака простаты |
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- 2016-12-20 EP EP16919556.7A patent/EP3527556B1/en active Active
- 2016-12-20 WO PCT/CN2016/110978 patent/WO2018072300A1/zh unknown
- 2016-12-20 HU HUE16919556A patent/HUE061557T2/hu unknown
- 2016-12-20 US US16/342,912 patent/US20200087261A1/en not_active Abandoned
- 2016-12-20 JP JP2019520547A patent/JP7241682B2/ja active Active
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Publication number | Priority date | Publication date | Assignee | Title |
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EP2656841A1 (en) * | 2006-03-27 | 2013-10-30 | The Regents of The University of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
CN101817787A (zh) * | 2009-02-26 | 2010-09-01 | 童友之 | 抗前列腺癌的雄性激素受体拮抗剂 |
CN103159680A (zh) * | 2011-12-14 | 2013-06-19 | 爱美尼迪药物有限公司 | 咪唑二酮类化合物及其用途 |
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Publication number | Publication date |
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PL3527556T3 (pl) | 2023-08-14 |
HUE061557T2 (hu) | 2023-07-28 |
TW201815768A (zh) | 2018-05-01 |
CA3040785C (en) | 2021-06-15 |
JP2019532075A (ja) | 2019-11-07 |
CN107954936A (zh) | 2018-04-24 |
EP3527556A1 (en) | 2019-08-21 |
FI3527556T3 (fi) | 2023-04-25 |
CN107954936B (zh) | 2021-03-19 |
EP3527556A4 (en) | 2020-04-29 |
CA3040785A1 (en) | 2018-04-26 |
JP7241682B2 (ja) | 2023-03-17 |
TWI728077B (zh) | 2021-05-21 |
AU2016426847A1 (en) | 2019-06-06 |
ES2943011T3 (es) | 2023-06-08 |
PT3527556T (pt) | 2023-05-02 |
DK3527556T3 (da) | 2023-05-01 |
US20200087261A1 (en) | 2020-03-19 |
AU2016426847B2 (en) | 2020-11-26 |
EP3527556B1 (en) | 2023-01-25 |
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