CN107108507B - 制备二芳基硫代乙内酰脲化合物的方法 - Google Patents

制备二芳基硫代乙内酰脲化合物的方法 Download PDF

Info

Publication number
CN107108507B
CN107108507B CN201580069602.5A CN201580069602A CN107108507B CN 107108507 B CN107108507 B CN 107108507B CN 201580069602 A CN201580069602 A CN 201580069602A CN 107108507 B CN107108507 B CN 107108507B
Authority
CN
China
Prior art keywords
compound
temperature
organic solvent
copper
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201580069602.5A
Other languages
English (en)
Chinese (zh)
Other versions
CN107108507A (zh
Inventor
C.B.海姆
A.霍瓦斯
J.E.E.维特斯
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aragon Pharmaceuticals Inc
Original Assignee
Aragon Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Aragon Pharmaceuticals Inc filed Critical Aragon Pharmaceuticals Inc
Priority to CN202410667649.2A priority Critical patent/CN118638097A/zh
Publication of CN107108507A publication Critical patent/CN107108507A/zh
Application granted granted Critical
Publication of CN107108507B publication Critical patent/CN107108507B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/04—Mixing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Materials Engineering (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
CN201580069602.5A 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法 Active CN107108507B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202410667649.2A CN118638097A (zh) 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462094436P 2014-12-19 2014-12-19
US62/094436 2014-12-19
PCT/US2015/066356 WO2016100652A2 (en) 2014-12-19 2015-12-17 Process for the preparation of a diarylthiohydantoin compound

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CN202410667649.2A Division CN118638097A (zh) 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法

Publications (2)

Publication Number Publication Date
CN107108507A CN107108507A (zh) 2017-08-29
CN107108507B true CN107108507B (zh) 2024-05-28

Family

ID=55168400

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201580069602.5A Active CN107108507B (zh) 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法
CN202410667649.2A Pending CN118638097A (zh) 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN202410667649.2A Pending CN118638097A (zh) 2014-12-19 2015-12-17 制备二芳基硫代乙内酰脲化合物的方法

Country Status (34)

Country Link
US (1) US9688655B2 (enExample)
EP (4) EP3372586A1 (enExample)
JP (2) JP6681902B2 (enExample)
KR (1) KR102586059B1 (enExample)
CN (2) CN107108507B (enExample)
AR (1) AR103228A1 (enExample)
AU (1) AU2015364537B2 (enExample)
BR (1) BR112017013113B1 (enExample)
CA (1) CA2970937A1 (enExample)
CY (3) CY1121684T1 (enExample)
DK (3) DK3372585T3 (enExample)
EA (4) EA201892486A1 (enExample)
ES (3) ES2718539T3 (enExample)
HR (3) HRP20220750T1 (enExample)
HU (2) HUE042409T2 (enExample)
IL (1) IL252843B2 (enExample)
LT (3) LT3372584T (enExample)
MA (1) MA41200B1 (enExample)
MD (1) MD3233803T2 (enExample)
ME (1) ME03420B (enExample)
MX (1) MX375467B (enExample)
NZ (1) NZ732766A (enExample)
PH (1) PH12017501152B1 (enExample)
PL (3) PL3233803T3 (enExample)
PT (3) PT3372585T (enExample)
RS (3) RS63455B1 (enExample)
SG (4) SG10201912811QA (enExample)
SI (3) SI3372585T1 (enExample)
SM (3) SMT202200242T1 (enExample)
TR (1) TR201904739T4 (enExample)
TW (4) TWI683810B (enExample)
UA (1) UA123201C2 (enExample)
WO (1) WO2016100652A2 (enExample)
ZA (1) ZA201704877B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2015364612B2 (en) 2014-12-19 2020-06-11 Aragon Pharmaceuticals, Inc. Processes for the preparation of a diarylthiohydantoin compound
EP3372586A1 (en) * 2014-12-19 2018-09-12 Aragon Pharmaceuticals, Inc. Process for the preparation of a diarylthiohydantoin compound
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
US10364245B2 (en) 2017-06-07 2019-07-30 Chiesi Farmaceutici S.P.A. Kinase inhibitors
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
CN108383749B (zh) * 2018-01-30 2021-03-09 杭州科巢生物科技有限公司 阿帕鲁胺的合成方法及其中间体
US10513504B2 (en) 2018-03-08 2019-12-24 Apotex Inc. Processes for the preparation of apalutamide and intermediates thereof
CN108314646B (zh) * 2018-04-11 2021-03-19 武汉慧敏科技中心 一种高分散双金属纳米材料制备泌尿生殖系统用药物中间体的方法
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
CN110511207A (zh) * 2019-06-17 2019-11-29 扬子江药业集团江苏海慈生物药业有限公司 芳基-2-硫代海因类化合物中间体、其制备方法及应用
CN110511206A (zh) * 2019-06-17 2019-11-29 扬子江药业集团江苏海慈生物药业有限公司 芳基-2-硫代海因类化合物中间体、其制备方法及应用
CN113968815B (zh) * 2020-07-24 2025-11-18 苏州科伦药物研究有限公司 一种硫代二氮杂螺类化合物的合成方法、其中间体及其合成方法
EP4541786A3 (en) 2020-09-04 2025-08-06 Synthon B.V. Improved process for preparation of apalutamide
AU2021382674A1 (en) 2020-11-20 2023-06-22 Amgen Inc. Process for preparing 7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3- yl)pyridof[2,3-d]pyrimidine-2,4(1h,3h)-dione
CN113292535B (zh) * 2021-06-18 2022-07-01 南京方生和医药科技有限公司 一种制备阿帕鲁胺中间体及阿帕鲁胺的方法
CN113402466B (zh) * 2021-06-18 2022-08-16 南京方生和医药科技有限公司 一种阿帕鲁胺中间体及制备阿帕鲁胺的方法
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
CN115850233B (zh) * 2021-09-24 2024-12-10 南京方生和医药科技有限公司 一种阿帕鲁胺的合成方法
CN116239536A (zh) * 2021-12-08 2023-06-09 山东新时代药业有限公司 一种阿帕鲁胺中间体化合物
CN117534652A (zh) * 2022-08-02 2024-02-09 黄冈人福药业有限责任公司 一种阿帕他胺的制备方法
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
CN116332907A (zh) * 2023-03-16 2023-06-27 奥锐特药业股份有限公司 一种无定形阿帕他胺的制备方法
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

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040077605A1 (en) * 2001-06-20 2004-04-22 Salvati Mark E. Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
WO2007126765A2 (en) * 2006-03-27 2007-11-08 The Regents Of The University Of California Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases
WO2008119015A2 (en) * 2007-03-27 2008-10-02 Sloan-Kettering Institute For Cancer Research Synthesis of thiohydantoins
WO2009140624A2 (en) * 2008-05-16 2009-11-19 Takeda San Diego, Inc. Glucokinase activators
WO2011069951A1 (en) * 2009-12-11 2011-06-16 Glaxo Group Limited Imidazolidinedione derivatives
CN102884057A (zh) * 2010-02-16 2013-01-16 亚拉冈制药公司 雄激素受体调节剂及其用途
WO2013029338A1 (en) * 2011-09-01 2013-03-07 Glaxo Group Limited Novel compounds
CN103108549A (zh) * 2010-02-24 2013-05-15 梅迪维新前列腺医疗股份有限公司 合成二芳基乙内酰硫脲和二芳基乙内酰脲化合物的方法
CA2908326A1 (en) * 2013-05-29 2014-12-04 Hinova Pharmaceuticals Inc. Imidazolidinedione compounds and their uses

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI263640B (en) * 2001-12-19 2006-10-11 Bristol Myers Squibb Co Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
BR112013023028B1 (pt) 2011-03-10 2021-09-21 Suzhou Kintor Pharmaceuticals, Inc Composto de fórmula (i) ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica e formulação farmacêutica tópica
MX358785B (es) * 2012-03-29 2018-09-04 Sangart Inc Hemoglobina pegilada reticulada con diaspirina.
EP3372586A1 (en) * 2014-12-19 2018-09-12 Aragon Pharmaceuticals, Inc. Process for the preparation of a diarylthiohydantoin compound

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040077605A1 (en) * 2001-06-20 2004-04-22 Salvati Mark E. Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
WO2007126765A2 (en) * 2006-03-27 2007-11-08 The Regents Of The University Of California Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases
WO2008119015A2 (en) * 2007-03-27 2008-10-02 Sloan-Kettering Institute For Cancer Research Synthesis of thiohydantoins
WO2009140624A2 (en) * 2008-05-16 2009-11-19 Takeda San Diego, Inc. Glucokinase activators
WO2011069951A1 (en) * 2009-12-11 2011-06-16 Glaxo Group Limited Imidazolidinedione derivatives
CN102884057A (zh) * 2010-02-16 2013-01-16 亚拉冈制药公司 雄激素受体调节剂及其用途
CN103108549A (zh) * 2010-02-24 2013-05-15 梅迪维新前列腺医疗股份有限公司 合成二芳基乙内酰硫脲和二芳基乙内酰脲化合物的方法
WO2013029338A1 (en) * 2011-09-01 2013-03-07 Glaxo Group Limited Novel compounds
CA2908326A1 (en) * 2013-05-29 2014-12-04 Hinova Pharmaceuticals Inc. Imidazolidinedione compounds and their uses

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
3,5,5-Trisubstitued Hydantoins from Activated (Benzloxycarbonyl-amino)malonic Acids;Lukas Hroch et al.;《Synthesis》;20121231;第44卷;第1907-1914页 *
Improved Functional Group Compatibility in the Palladium-Catalyzed Amination of Aryl Bromides;John P. Wolfe et al.;《Tetrahedron Letters》;19971231;第38卷(第36期);第6359-6362页 *
硫脲类化合物合成方法研究进展;丁从文等;《有机化学》;20101231;第30卷(第2期);第173-180页 *

Also Published As

Publication number Publication date
AU2015364537B2 (en) 2020-10-08
SG10201912802XA (en) 2020-02-27
RS58454B1 (sr) 2019-04-30
TW201639825A (zh) 2016-11-16
SMT201900208T1 (it) 2019-05-10
RS63455B1 (sr) 2022-08-31
DK3372584T3 (da) 2021-01-04
PT3372585T (pt) 2022-07-08
CY1121684T1 (el) 2020-07-31
PT3233803T (pt) 2019-05-20
HRP20201847T2 (hr) 2021-05-28
PH12017501152B1 (en) 2022-04-29
LT3372585T (lt) 2022-07-11
SI3233803T1 (sl) 2019-05-31
DK3372585T3 (da) 2022-05-30
MA41200B1 (fr) 2019-05-31
CN107108507A (zh) 2017-08-29
TWI753336B (zh) 2022-01-21
NZ732766A (en) 2023-07-28
IL252843A0 (en) 2017-08-31
US9688655B2 (en) 2017-06-27
UA123201C2 (uk) 2021-03-03
BR112017013113B1 (pt) 2023-11-21
TR201904739T4 (tr) 2019-05-21
ES2919951T3 (es) 2022-07-29
AU2015364537A1 (en) 2017-07-06
EA201892485A1 (ru) 2019-07-31
EA201892486A1 (ru) 2019-07-31
WO2016100652A3 (en) 2016-08-25
LT3372584T (lt) 2020-12-10
TW201945342A (zh) 2019-12-01
ES2827549T9 (es) 2021-07-02
TWI689494B (zh) 2020-04-01
JP2020114842A (ja) 2020-07-30
CN118638097A (zh) 2024-09-13
HRP20190540T1 (hr) 2019-06-14
MX2017008179A (es) 2017-09-18
SMT202000618T1 (it) 2021-01-05
EA201892487A1 (ru) 2019-07-31
HRP20220750T1 (hr) 2022-09-02
PT3372584T (pt) 2020-11-13
SG10201912811QA (en) 2020-02-27
KR20170095976A (ko) 2017-08-23
ES2827549T3 (es) 2021-05-21
DK3372584T5 (da) 2021-05-17
BR112017013113A2 (pt) 2017-12-26
SG10201912805SA (en) 2020-02-27
EP3233803B1 (en) 2019-01-30
EP3372584A1 (en) 2018-09-12
MA41200A (fr) 2017-10-25
AR103228A1 (es) 2017-04-26
EP3233803A2 (en) 2017-10-25
SI3372584T1 (sl) 2021-08-31
JP6903785B2 (ja) 2021-07-14
PL3233803T3 (pl) 2019-07-31
TW201945343A (zh) 2019-12-01
TWI683810B (zh) 2020-02-01
JP2018501237A (ja) 2018-01-18
EP3372586A1 (en) 2018-09-12
ME03420B (me) 2020-01-20
HUE052475T2 (hu) 2021-05-28
DK3233803T3 (en) 2019-04-08
EP3372584B1 (en) 2020-09-23
SG11201704969QA (en) 2017-07-28
MX375467B (es) 2025-03-06
MD3233803T2 (ro) 2019-07-31
SI3372585T1 (sl) 2022-08-31
ES2718539T3 (es) 2019-07-02
TWI703132B (zh) 2020-09-01
US20160176845A1 (en) 2016-06-23
IL252843B2 (en) 2025-02-01
EP3372584B9 (en) 2021-03-31
IL252843B1 (en) 2024-10-01
EA201791390A1 (ru) 2017-10-31
JP6681902B2 (ja) 2020-04-15
CY1125243T1 (el) 2025-03-28
CY1123611T1 (el) 2022-03-24
EP3372585B1 (en) 2022-03-30
CA2970937A1 (en) 2016-06-23
RS61060B9 (sr) 2021-07-30
PH12017501152A1 (en) 2017-11-27
PL3372584T3 (pl) 2021-07-05
ZA201704877B (en) 2019-02-27
LT3233803T (lt) 2019-04-10
WO2016100652A2 (en) 2016-06-23
RS61060B1 (sr) 2020-12-31
EP3372585A1 (en) 2018-09-12
HUE042409T2 (hu) 2019-06-28
SMT202200242T1 (it) 2022-07-21
KR102586059B1 (ko) 2023-10-05
HRP20201847T1 (hr) 2021-03-19
PL3372585T3 (pl) 2022-10-10
TW202031639A (zh) 2020-09-01

Similar Documents

Publication Publication Date Title
CN107108507B (zh) 制备二芳基硫代乙内酰脲化合物的方法
JP2017523168A (ja) ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法
TWI617562B (zh) 用於由４－胺基－２，５－二甲氧基嘧啶製備２－胺基－５，８－二甲氧基［１，２，４］三唑并［１，５－ｃ］嘧啶的改良方法
HK1260788A1 (en) Process for the preparation of a diarylthiohydantoin compound
HK1260790B (en) Process for the preparation of a diarylthiohydantoin compound
HK1260790A1 (en) Process for the preparation of a diarylthiohydantoin compound
US20160176844A1 (en) Processes for the preparation of a diarylthiohydantoin compound
HK1260789B (en) Process for the preparation of a diarylthiohydantoin compound
HK1260789A1 (en) Process for the preparation of a diarylthiohydantoin compound
EA041899B1 (ru) Способ получения соединения диарилтиогидантоина

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant