JP2013520519A5 - - Google Patents
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- JP2013520519A5 JP2013520519A5 JP2012555160A JP2012555160A JP2013520519A5 JP 2013520519 A5 JP2013520519 A5 JP 2013520519A5 JP 2012555160 A JP2012555160 A JP 2012555160A JP 2012555160 A JP2012555160 A JP 2012555160A JP 2013520519 A5 JP2013520519 A5 JP 2013520519A5
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- 150000001875 compounds Chemical class 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C1)C=CC(*)=C1[N+]([O-])=O Chemical compound CC(C1)C=CC(*)=C1[N+]([O-])=O 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OEKATORRSPXJHE-UHFFFAOYSA-N 2-acetylcyclohexan-1-one Chemical compound CC(=O)C1CCCCC1=O OEKATORRSPXJHE-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30779610P | 2010-02-24 | 2010-02-24 | |
| US61/307,796 | 2010-02-24 | ||
| PCT/US2011/026135 WO2011106570A1 (en) | 2010-02-24 | 2011-02-24 | Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013520519A JP2013520519A (ja) | 2013-06-06 |
| JP2013520519A5 true JP2013520519A5 (cg-RX-API-DMAC7.html) | 2014-01-30 |
| JP5718372B2 JP5718372B2 (ja) | 2015-05-13 |
Family
ID=44507217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012555160A Active JP5718372B2 (ja) | 2010-02-24 | 2011-02-24 | ジアリールチオヒダントイン化合物およびジアリールヒダントイン化合物を合成するためのプロセス |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9174943B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2538785B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5718372B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101514659B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN103108549B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112012021406B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2790924C (cg-RX-API-DMAC7.html) |
| CY (2) | CY1120207T1 (cg-RX-API-DMAC7.html) |
| DK (2) | DK2538785T3 (cg-RX-API-DMAC7.html) |
| ES (2) | ES2671343T3 (cg-RX-API-DMAC7.html) |
| HU (2) | HUE038637T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2012009782A (cg-RX-API-DMAC7.html) |
| PL (2) | PL3329775T3 (cg-RX-API-DMAC7.html) |
| PT (2) | PT3329775T (cg-RX-API-DMAC7.html) |
| RU (1) | RU2554081C2 (cg-RX-API-DMAC7.html) |
| SI (2) | SI3329775T1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011106570A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7709517B2 (en) * | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| PE20121470A1 (es) | 2007-10-26 | 2012-11-18 | Univ California | Compuestos de diarilhidantoina como antagonistas del receptor de androgeno |
| KR101819199B1 (ko) | 2010-02-16 | 2018-01-16 | 아라곤 파마슈티컬스, 인코포레이티드 | 안드로겐 수용체 조절제 및 이의 용도 |
| WO2012119559A1 (en) | 2011-03-10 | 2012-09-13 | Suzhou Kintor Pharmaceuticals,Inc. | Androgen receptor antagonists and uses thereof |
| WO2013067151A1 (en) * | 2011-11-02 | 2013-05-10 | Medivation Prostate Therapeutics, Inc. | Treatment methods using diarylthiohydantoin derivatives |
| AU2013316754A1 (en) * | 2012-09-11 | 2015-04-30 | Dr. Reddy's Laboratories Limited | Enzalutamide polymorphic forms and its preparation |
| CN105358535B (zh) | 2012-09-11 | 2019-01-04 | 麦迪威森前列腺医疗有限责任公司 | 恩杂鲁胺制剂 |
| EA030128B1 (ru) | 2012-09-26 | 2018-06-29 | Арагон Фармасьютикалз, Инк. | Способ лечения неметастатического кастрационно-резистентного рака простаты |
| CA2889756C (en) | 2012-10-26 | 2023-03-14 | Memorial Sloan-Kettering Cancer Center | Thiohydantoin compounds as androgen receptor modulators |
| JOP20200097A1 (ar) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | معدل مستقبل أندروجين واستخداماته |
| RU2520134C1 (ru) * | 2013-02-27 | 2014-06-20 | Общество с ограниченной ответственностью "Авионко" (ООО "Авионко") | Замещенные (r)-3-(4-метилкарбамоил-3-фторфениламино)-тетрагидро-фуран-3-енкарбоновые кислоты и их эфиры, способ их получения и применения |
| WO2014167428A2 (en) * | 2013-04-10 | 2014-10-16 | Shilpa Medicare Limited | Amorphous 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-n-methylbenzamide |
| EP3046556A4 (en) * | 2013-09-19 | 2017-04-26 | Glaxosmithkline LLC | Combination drug therapy |
| WO2015054804A1 (zh) * | 2013-10-14 | 2015-04-23 | 杭州普晒医药科技有限公司 | 恩杂鲁胺的固态形式及其制备方法和用途 |
| EP3063135A1 (en) | 2013-10-31 | 2016-09-07 | Sun Pharmaceutical Industries Ltd | Process for the preparation of enzalutamide |
| EP3083568A1 (en) | 2013-12-16 | 2016-10-26 | Sun Pharmaceutical Industries Ltd | Processes and intermediates for the preparation of enzalutamide |
| CN104803919A (zh) * | 2014-01-26 | 2015-07-29 | 上海医药工业研究院 | 用于制备恩杂鲁胺中间体的方法 |
| 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 |
| US9611225B2 (en) * | 2014-01-27 | 2017-04-04 | Cadila Healthcare Limited | Process for preparation of androgen receptor antagonist |
| CN104844520B (zh) * | 2014-02-13 | 2017-09-05 | 成都伊诺达博医药科技有限公司 | 一种合成恩杂鲁胺的方法 |
| EP3105208A1 (en) | 2014-02-13 | 2016-12-21 | Ranbaxy Laboratories Limited | Process for the preparation of enzalutamide |
| CN104844521B (zh) * | 2014-02-13 | 2017-08-15 | 成都伊诺达博医药科技有限公司 | 抗前列腺癌药物恩杂鲁胺的合成方法 |
| CZ2014232A3 (cs) | 2014-04-07 | 2015-10-14 | Zentiva, K.S. | Způsob výroby enzalutamidu |
| CN103910679B (zh) * | 2014-04-23 | 2016-05-25 | 杭州新博思生物医药有限公司 | 一种恩杂鲁胺的制备方法 |
| CN103980141A (zh) * | 2014-04-25 | 2014-08-13 | 山东大学 | 恩泽特鲁的合成方法 |
| 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 |
| US20170190670A1 (en) * | 2014-07-11 | 2017-07-06 | Shilpa Medicare Limited | Improved process for the preparation of enzalutamide |
| CN105461633A (zh) * | 2014-07-31 | 2016-04-06 | 江苏豪森药业集团有限公司 | 恩杂鲁胺的制备方法 |
| CN105367441B (zh) * | 2014-08-18 | 2018-11-06 | 上海医药工业研究院 | 用于合成恩杂鲁胺的新化合物 |
| CN105461634A (zh) * | 2014-08-19 | 2016-04-06 | 江苏豪森药业集团有限公司 | 恩杂鲁胺的制备方法 |
| WO2016051423A2 (en) * | 2014-10-01 | 2016-04-07 | Laurus Labs Private Limited | An improved process for the preparation of enzalutamide |
| 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 |
| ES2919951T3 (es) * | 2014-12-19 | 2022-07-29 | Aragon Pharmaceuticals Inc | Proceso para la preparación de un compuesto de diariltiohidantoina |
| ITUB20151204A1 (it) | 2015-05-28 | 2016-11-28 | Olon Spa | Procedimento per la preparazione di enzalutamide |
| ITUB20151256A1 (it) | 2015-05-28 | 2016-11-28 | Olon Spa | Processo industriale per la preparazione di enzalutamide |
| ITUB20151311A1 (it) * | 2015-05-28 | 2016-11-28 | Olon Spa | Procedimento per la preparazione di enzalutamide |
| PT3305770T (pt) | 2015-05-29 | 2023-04-26 | Astellas Pharma Inc | Processo para a produção de forma cristalina de enzalutamida |
| TWI613194B (zh) | 2015-06-10 | 2018-02-01 | 台灣神隆股份有限公司 | 用於製備恩雜魯胺的新穎方法 |
| CN105330560A (zh) * | 2015-10-13 | 2016-02-17 | 福格森（武汉）生物科技股份有限公司 | 一种恩杂鲁胺中间体的制备方法 |
| TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
| CN107954936B (zh) * | 2016-10-17 | 2021-03-19 | 海创药业股份有限公司 | 一种制备氘代咪唑二酮类化合物的方法 |
| CN108069869B (zh) * | 2016-11-09 | 2022-03-01 | 上海医药工业研究院 | 一种Apalutamide的制备方法及其中间体 |
| TW201831461A (zh) * | 2017-01-18 | 2018-09-01 | 台灣神隆股份有限公司 | 製備阿帕魯醯胺的方法 |
| EP3616696B1 (en) | 2017-04-28 | 2025-03-05 | Astellas Pharma Inc. | Orally administrable enzalutamide-containing pharmaceutical composition |
| CN107501237B (zh) * | 2017-08-17 | 2022-03-22 | 上海西浦医药科技有限公司 | 一种Apalutamide的合成方法 |
| KR20240096623A (ko) | 2017-10-16 | 2024-06-26 | 아라곤 파마슈티컬스, 인코포레이티드 | 비-전이성 거세-저항성 전립선암의 치료를 위한 항-안드로겐 |
| HUE064356T2 (hu) * | 2017-11-28 | 2024-03-28 | Aarti Pharmalabs Ltd | Eljárás enzalutamid elõállítására új intermedier felhasználásával |
| CN108047200A (zh) * | 2017-12-05 | 2018-05-18 | 上海丰瑞医药科技有限公司 | 一种二芳基乙内酰硫脲类化合物的制备方法及其中间体 |
| CN109988077A (zh) * | 2017-12-29 | 2019-07-09 | 上海法默生物科技有限公司 | 一种阿帕鲁胺的合成方法及中间体 |
| CN110872258B (zh) * | 2018-09-04 | 2021-05-25 | 北京凯莱天成医药科技有限公司 | 一种前列腺癌药物恩杂鲁胺的制备工艺 |
| CN109651256A (zh) * | 2018-11-20 | 2019-04-19 | 上海健康医学院 | 一种式（viii）的恩杂鲁胺的制备方法 |
| CN109503416A (zh) * | 2018-12-24 | 2019-03-22 | 常州智超化学有限公司 | 一种恩杂鲁胺中间体合成方法 |
| CN112047888B (zh) * | 2019-06-05 | 2024-08-02 | 安礼特（上海）医药科技有限公司 | 一种合成恩杂鲁胺的方法 |
| CN111320552B (zh) * | 2020-02-28 | 2023-10-27 | 江西科睿药业有限公司 | 一种恩扎卢胺中间体的制备方法 |
| CN114685601B (zh) | 2020-12-30 | 2024-10-18 | 财团法人工业技术研究院 | 雄性激素受体结合分子及其用途 |
| WO2022206742A1 (zh) * | 2021-03-30 | 2022-10-06 | 苏州开拓药业股份有限公司 | 一种一步法合成乙内酰硫脲衍生物的方法 |
| EP4112603A1 (en) | 2021-06-29 | 2023-01-04 | Química Sintética, S.A. | Processes for the preparation of non-steroidal antiandrogens |
| CN115572264B (zh) * | 2021-07-06 | 2025-12-05 | 山东新时代药业有限公司 | 一种恩杂鲁胺的制备方法 |
| 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 |
| CN114591246A (zh) * | 2022-03-25 | 2022-06-07 | 重庆华邦制药有限公司 | 一种恩扎卢胺的纯化方法 |
| CN114907439B (zh) * | 2022-06-29 | 2023-07-21 | 云南中医药大学 | 一种抗癌化合物及其制药用途 |
| CN115181043B (zh) * | 2022-07-27 | 2024-05-07 | 爱斯特（成都）生物制药股份有限公司 | 一种连续流制备4-异硫氰基-2-(三氟甲基)苯甲腈的方法 |
| CN115611765A (zh) * | 2022-09-30 | 2023-01-17 | 重庆华邦胜凯制药有限公司 | 一种恩扎卢胺中间体的制备方法 |
| CN115536634B (zh) * | 2022-10-17 | 2024-06-11 | 上海博悦生物科技有限公司 | 一种阿帕他胺的合成方法 |
| CN115724759B (zh) * | 2022-11-23 | 2024-06-25 | 爱斯特（成都）生物制药股份有限公司 | 一种恩扎卢胺中间体的制备方法 |
| CN117645572A (zh) * | 2023-11-23 | 2024-03-05 | 奥锐特药业股份有限公司 | 恩扎卢胺及其中间体的制备方法 |
| CN118496163B (zh) * | 2024-05-08 | 2025-02-25 | 奥锐特药业股份有限公司 | 一种恩扎卢胺及其中间体的制备方法 |
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| BRPI0820696A2 (pt) * | 2007-12-20 | 2019-09-24 | Hoffmann La Roche | hidantoínas substituídas como inibidores de cinase de mek |
| BRPI1007990A2 (pt) * | 2009-02-24 | 2015-09-01 | Medivation Prostate Therapeutics Inc | Compostos específicos de diaril-hidantoína e diariltioidantoína. |
| 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 |
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2011
- 2011-02-24 RU RU2012140454/04A patent/RU2554081C2/ru active
- 2011-02-24 SI SI201131988T patent/SI3329775T1/sl unknown
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- 2011-02-24 MX MX2012009782A patent/MX2012009782A/es active IP Right Grant
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- 2011-02-24 WO PCT/US2011/026135 patent/WO2011106570A1/en not_active Ceased
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- 2011-02-24 BR BR112012021406-3A patent/BR112012021406B1/pt active IP Right Grant
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2013
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