DK2538785T3 - Fremgangsmåder til syntese af diarylthiohydantoin- og diarylhydantoinforbindelser - Google Patents
Fremgangsmåder til syntese af diarylthiohydantoin- og diarylhydantoinforbindelser Download PDFInfo
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- DK2538785T3 DK2538785T3 DK11748095.4T DK11748095T DK2538785T3 DK 2538785 T3 DK2538785 T3 DK 2538785T3 DK 11748095 T DK11748095 T DK 11748095T DK 2538785 T3 DK2538785 T3 DK 2538785T3
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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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (23)
1. Fremgangsmåde til fremstilling af en forbindelse med formlen (I):
i hvor fremgangsmåden omfatter omsætning af forbindelsen med formlen D:
D hvor R6 er CrC8-alkyl; med forbindelsen med formlen (F):
F
2. Fremgangsmåde ifølge krav 1, der omfatter blanding af forbindelse D med forbindelse F i et polært opløsningsmiddel, eller i en blanding af et første polært opløsningsmiddel og et andet polært opløsningsmiddel, og opvarmning til 60-100 °C i et tidsrum på 1 til 48 timer.
3. Fremgangsmåde ifølge krav 2, hvor reaktionsblandingen endvidere afkøles til 15 til 30 °C og kombineres med vand, efterfulgt af udskillelse af det ønskede produkt med et polært opløsningsmiddel, eller med en blanding af et tredje polært opløsningsmiddel og et fjerde polært opløsningsmiddel.
4. Fremgangsmåde ifølge krav 2 eller 3, hvor det polære opløsningsmiddel udvælges, eller det første, andet, tredje og fjerde polære opløsningsmiddel udvælges fra gruppen bestående af dimethylsulfoxid (DMSO), dimethylformamid (DMF), N-methylpyrrolidon (NMP), dimethylacetamid (DMA), isopropylacetat (IPAc), MeCN og isopropylalkohol (IPA).
5. Fremgangsmåde ifølge et hvilket som helst af kravene 2 til 4, der omfatter blanding af forbindelsen med formlen D med forbindelsen med formlen F i en blanding af et første polært opløsningsmiddel, der er isopropylacetat (IPAc), og et andet polært opløsningsmiddel, der er dimethylsulfoxid (DMSO).
6. Fremgangsmåde ifølge krav 1, der omfatter blanding af forbindelse D med forbindelse F i en blanding af et første polært opløsningsmiddel og et andet polært opløsningsmiddel, og opvarmning, derefter afkøling af blandingen og kombinering med vand, og udskillelse af det ønskede produkt med en blanding af et tredje polært opløsningsmiddel og et fjerde polært opløsningsmiddel.
7. Fremgangsmåde ifølge krav 6, hvor det første, andet, tredje og fjerde polære opløsningsmiddel er udvalgt fra gruppen bestående af dimethylsulfoxid (DMSO), dimethylformamid (DMF), N-methylpyrrolidon (NMP), dimethylacetamid (DMA), isopropylacetat (IPAc) og isopropylalkohol (IPA).
8. Fremgangsmåde ifølge krav 3 eller krav 6, hvor det første polære opløsningsmiddel er isopropylacetat (IPAc), det andet polære opløsningsmiddel er dimethylsulfoxid (DMSO), det tredje polære opløsningsmiddel er IPAc og det fjerde polære opløsningsmiddel er isopropylalkohol (IPA).
9. Fremgangsmåde ifølge krav 1, der omfatter omsætning af en forbindelse med formlen D-1
D-1 med en forbindelse med formlen F
F i tilstedeværelse af DMSO.
10. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 9, der endvidere omfatter omsætning af forbindelsen med formlen A:
A hvor LG er en fraspaltelig gruppe, Br eller I; med forbindelsen med formlen B:
B for at opnå en forbindelse med formlen C:
c omsætning af forbindelsen med formlen C med en forbindelse med formlen R6-LG under alkyleringsbetingelser eller med en forbindelse med formlen R6-OH under esterificeringsbetingelser for at danne forbindelsen med formlen D:
D
11. Fremgangsmåde ifølge krav 10, hvor omsætningen af forbindelsen med formlen A med forbindelsen med formlen B for at danne forbindelsen med formlen C udføres i tilstedeværelse af en katalytisk mængde kobber-(l) chlorid af 0,05-0,35 ækvivalenter i forhold til forbindelse A og acetylcyclohexanon i en mængden ca. lig med mængden af anvendt kobber-(l) chlorid.
12. Fremgangsmåde ifølge krav 10 eller 11, hvor trinnet med omdannelse af forbindelsen med formlen C til forbindelsen med formlen D udføres ved alkylering af forbindelsen med formlen C med et alkylhalogenid.
13. Fremgangsmåde ifølge krav 12, hvor alkylhalogenidet er methyliodid.
14. Fremgangsmåde ifølge krav 12 eller 13, hvor alkyleringen udføres i tilstedeværelse af en uorganisk base.
15. Fremgangsmåde ifølge krav 14, hvor den uorganiske base er kaliumcarbonat.
16. Fremgangsmåde ifølge et hvilket som helst af kravene 10 til 15, hvor, efter trinnet med omdannelse af forbindelsen med formlen C til forbindelsen med formlen D, forbindelsen med formlen D isoleres ved tilsætning af vand til reaktionsblandingen for at udskille forbindelsen med formlen D.
17. Fremgangsmåde ifølge krav 12, 13, 14, 15 og 16, hvor 10-18 vandvolumener tilsættes reaktionsblandingen over 1 time for at udskille forbindelsen med formlen D.
18. Fremgangsmåde ifølge krav 17, hvor forbindelsen med formlen D resuspenderes eller igen opslæmmes i vand, efterfulgt af reisolering af forbindelsen med formlen D.
19. Fremgangsmåde ifølge krav 17 eller 18, hvor restkaliumindholdet eller restbaseindholdet i forbindelsen med formlen D er mindre end eller lig med 500 ppm.
20. Fremgangsmåde ifølge krav 18, hvor forbindelsen med formlen D tørres efter re-isolering.
21. Fremgangsmåde ifølge krav 20, hvor restfugtindholdet af forbindelsen med formlen D er mindre end eller lig med 0,1 %.
22. Fremgangsmåde ifølge krav 20, hvor restfugtindholdet af forbindelsen med formlen D er mindre end eller lig med 0,1 % og restkaliumindholdet eller restbaseindholdet i forbindelsen med formlen D er mindre end eller lig med 500 ppm.
23. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, der omfatter fremstilling af en forbindelse med formlen I og dannelse af en farmaceutisk sammensætning, der omfatter forbindelsen og en farmaceutisk acceptabel bærer eller excipiens.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30779610P | 2010-02-24 | 2010-02-24 | |
| PCT/US2011/026135 WO2011106570A1 (en) | 2010-02-24 | 2011-02-24 | Processes for the synthesis of diarylthiohydantoin and diarylhydantoin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2538785T3 true DK2538785T3 (da) | 2018-05-22 |
Family
ID=44507217
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK11748095.4T DK2538785T3 (da) | 2010-02-24 | 2011-02-24 | Fremgangsmåder til syntese af diarylthiohydantoin- og diarylhydantoinforbindelser |
| DK18153287.0T DK3329775T3 (da) | 2010-02-24 | 2011-02-24 | Fremgangsmåder til syntese af diarylthiohydantoin- og diarylhydantoinforbindelser |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK18153287.0T DK3329775T3 (da) | 2010-02-24 | 2011-02-24 | Fremgangsmåder til syntese af diarylthiohydantoin- og diarylhydantoinforbindelser |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9174943B2 (da) |
| EP (2) | EP2538785B1 (da) |
| JP (1) | JP5718372B2 (da) |
| KR (1) | KR101514659B1 (da) |
| CN (1) | CN103108549B (da) |
| BR (1) | BR112012021406B1 (da) |
| CA (1) | CA2790924C (da) |
| CY (2) | CY1120207T1 (da) |
| DK (2) | DK2538785T3 (da) |
| ES (2) | ES2671343T3 (da) |
| HU (2) | HUE055051T2 (da) |
| MX (1) | MX2012009782A (da) |
| PL (2) | PL3329775T3 (da) |
| PT (2) | PT3329775T (da) |
| RU (1) | RU2554081C2 (da) |
| SI (2) | SI3329775T1 (da) |
| WO (1) | WO2011106570A1 (da) |
Families Citing this family (63)
| 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 |
| UY31432A1 (es) | 2007-10-26 | 2009-05-29 | Compuestos de diarilhidantoina | |
| MX355915B (es) * | 2010-02-16 | 2018-05-04 | Aragon Pharmaceuticals Inc | Moduladores del receptor de androgenos y usos de los mismos. |
| RU2598854C2 (ru) | 2011-03-10 | 2016-09-27 | Сучжоу Кинтор Фармасьютикалз, Инк. | Производные тиогидантоина, полезные в качестве антагонистов рецептора андрогена |
| WO2013067151A1 (en) * | 2011-11-02 | 2013-05-10 | Medivation Prostate Therapeutics, Inc. | Treatment methods using diarylthiohydantoin derivatives |
| RU2015113434A (ru) | 2012-09-11 | 2016-11-10 | Др. Редди'С Лабораторис Лимитед | Полиморфные формы энзалутамида и их получение |
| RS62676B1 (sr) | 2012-09-11 | 2021-12-31 | Medivation Prostate Therapeutics Llc | Formulacije enzalutamida |
| EA202190820A1 (ru) | 2012-09-26 | 2021-10-29 | Арагон Фармасьютикалз, Инк. | Антиандрогены для лечения неметастатического кастрационно-резистентного рака простаты |
| AU2013334102B2 (en) | 2012-10-26 | 2018-08-16 | Memorial Sloan-Kettering Cancer Center | Modulators of resistant androgen receptor |
| 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 |
| US20160228446A1 (en) * | 2013-09-19 | 2016-08-11 | GlaxoSmithKline LLCC | Combination Drug Therapy |
| CN106543085A (zh) * | 2013-10-14 | 2017-03-29 | 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 |
| US20160251316A1 (en) | 2013-10-31 | 2016-09-01 | Sun Pharmaceutical Industries Limited | Process for the preparation of enzalutamide |
| WO2015092617A1 (en) | 2013-12-16 | 2015-06-25 | Ranbaxy Laboratories Limited | Processes and intermediates for the preparation of enzalutamide |
| 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 |
| 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 |
| US9611225B2 (en) * | 2014-01-27 | 2017-04-04 | Cadila Healthcare Limited | Process for preparation of androgen receptor antagonist |
| 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 |
| 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 |
| US20170174635A1 (en) | 2014-02-13 | 2017-06-22 | Sun Pharmaceutical Industries Limited | Process for the preparation of enzalutamide |
| 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 |
| WO2016005875A1 (en) * | 2014-07-11 | 2016-01-14 | Shilpa Medicare Limited | An 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 |
| US10131636B2 (en) * | 2014-10-01 | 2018-11-20 | Laurus Labs Limited | 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 |
| HUE052475T2 (hu) * | 2014-12-19 | 2021-05-28 | Aragon Pharmaceuticals Inc | Eljárás diaril-tiohidantoin vegyület elõállítására |
| ITUB20151311A1 (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 |
| ITUB20151204A1 (it) | 2015-05-28 | 2016-11-28 | Olon Spa | Procedimento per la preparazione di enzalutamide |
| ES2942618T3 (es) | 2015-05-29 | 2023-06-05 | Astellas Pharma Inc | Procedimiento para la fabricación de una 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 |
| KR20190137920A (ko) | 2017-04-28 | 2019-12-11 | 아스텔라스세이야쿠 가부시키가이샤 | 엔잘루타미드를 함유하는 경구 투여용 의약 조성물 |
| 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 |
| WO2019078920A1 (en) | 2017-10-16 | 2019-04-25 | Aragon Pharmaceuticals, Inc. | ANTI-ANDROGENS FOR THE TREATMENT OF NON-METASTATIC RESISTANT PROSTATE CANCER |
| EP3717457B1 (en) * | 2017-11-28 | 2023-06-21 | Aarti Industries Limited | Process for preparation of enzalutamide using novel intermediate |
| 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 |
| CN112047888A (zh) * | 2019-06-05 | 2020-12-08 | 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 |
| CN117120436A (zh) * | 2021-03-30 | 2023-11-24 | 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 |
| 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 |
| CN115724759A (zh) * | 2022-11-23 | 2023-03-03 | 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 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2884448A (en) * | 1956-07-02 | 1959-04-28 | Gen Aniline & Film Corp | Hydrolysis of n-substituted amides |
| DE1906492B2 (de) * | 1969-02-10 | 1980-07-31 | Bayer Ag, 5090 Leverkusen | Carbonsäure-Derivate enthaltende Hydantoine und Polyhydantoine |
| US4424396A (en) * | 1982-07-21 | 1984-01-03 | Occidental Chemical Corporation | Process for the preparation substituted anilino acids |
| FR2693461B1 (fr) * | 1992-07-08 | 1994-09-02 | Roussel Uclaf | Nouvelles phénylimidazolidines substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| US5235093A (en) * | 1992-01-27 | 1993-08-10 | Monsanto Company | Process for preparing carboxylic amide ester |
| FR2823209B1 (fr) * | 2001-04-04 | 2003-12-12 | Fournier Lab Sa | Nouvelles thiohydantoines et leur utilisation en therapeutique |
| RU2206326C2 (ru) | 2001-04-10 | 2003-06-20 | Асафов Александр Виленович | Применение натрия нуклеоспермата для лечения вич-инфекции и способ лечения |
| CN101048381A (zh) * | 2004-09-09 | 2007-10-03 | 中外制药株式会社 | 新型四氢咪唑衍生物及其用途 |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| RS52274B2 (sr) * | 2005-05-13 | 2018-05-31 | Univ California | Jedinjenje diarilhidantoina |
| DK2656842T3 (da) * | 2006-03-27 | 2016-11-07 | Univ California | Androgen receptormodulator til behandling af prostatacancer og androgene receptor-associerede sygdomme |
| SG10201408699TA (en) | 2006-03-29 | 2015-02-27 | Univ California | Diarylthiohydantoin compounds |
| TW200846338A (en) * | 2007-02-01 | 2008-12-01 | Chugai Pharmaceutical Co Ltd | Pyridyl imidazolidine derivative having sulfamoyl group, and pharmaceutical use thereof |
| US8461343B2 (en) * | 2007-03-27 | 2013-06-11 | Sloan-Kettering Institute For Cancer Research | Synthesis of thiohydantoins |
| UY31432A1 (es) | 2007-10-26 | 2009-05-29 | Compuestos de diarilhidantoina | |
| AU2008341680A1 (en) * | 2007-12-20 | 2009-07-02 | F. Hoffmann-La Roche Ag | Substituted hydantoins as MEK kinase inhibitors |
| MX2011008858A (es) * | 2009-02-24 | 2012-01-27 | Medivation Prostate Therapeutics Inc | Compuestos de diarilhidantoina y diariltiohidantoina especificos. |
| 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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