HRP20220750T1 - Postupak za proizvodnju spoja diariltiohidantoina - Google Patents
Postupak za proizvodnju spoja diariltiohidantoina Download PDFInfo
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- HRP20220750T1 HRP20220750T1 HRP20220750TT HRP20220750T HRP20220750T1 HR P20220750 T1 HRP20220750 T1 HR P20220750T1 HR P20220750T T HRP20220750T T HR P20220750TT HR P20220750 T HRP20220750 T HR P20220750T HR P20220750 T1 HRP20220750 T1 HR P20220750T1
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- Prior art keywords
- compound
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- catalyst
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- xylenes
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- 150000001875 compounds Chemical class 0.000 title claims 19
- 238000000034 method Methods 0.000 title claims 9
- 239000003054 catalyst Substances 0.000 claims 6
- 239000000839 emulsion Substances 0.000 claims 4
- -1 isocyanate compound Chemical class 0.000 claims 4
- 239000008096 xylene Substances 0.000 claims 4
- 150000003738 xylenes Chemical class 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 239000003791 organic solvent mixture Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 claims 1
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 claims 1
- 229910003953 H3PO2 Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 229910003206 NH4VO3 Inorganic materials 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- 150000008363 butyronitriles Chemical class 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
- 229910021641 deionized water Inorganic materials 0.000 claims 1
- 239000012973 diazabicyclooctane Substances 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
-
- 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
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- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
Claims (6)
1. Postupak, naznačen time, da za je proizvodnju spoja (XII-c) iz spoja (IV)
[image]
u skladu sa shemom:
[image]
gdje postupak obuhvaća reakciju spoja formule (XI-c):
[image]
,
pri čemu P je prikladna amino zaštitna skupina, sa:
(a) spojem (IV) pod uvjetima za tvorbu amidne veze, u prisutosti amidnog veznog reagensa i u prisutnosti katalizatora, u organskom otapalu, na temperaturi u rasponu od 0°C do 50°C; ili
(b) izocijanatnim spojem (IVa) u prisutnosti nenukleofilne baze na temperaturi u rasponu od -20°C do 80°C
[image]
dok je izocijanatni spoj formule (IVa) izveden iz reakcije spoja (IV) s fosgenom ili analogom fosgena, u prisutnosti organske baze u aprotičnom otapalu; i
pri čemu postupak rezultira s tvorbom odgovarajućeg spoja (XII-c).
2. Postupak prema patentnom zahtjevu 1, naznačen time, da prikladna amino zaštitna skupina je karbamat (-NHCO2R) pri čemu R je C1-8 alkil, fenil, ili aril(C1-8)alkil.
3. Postupak prema patentnom zahtjevu 1 ili 2, naznačen time, da uvjeti za tvorbu amidne veze obuhvaćaju reakciju spoja (IV) sa spojem (XI-c), u prisutnosti amidnog veznog reagensa koji je odabran iz skupine koju čine 1,1-karbonildiimidazol, T3P, EDCI, DMTMM, ili EEDQ, u prisutnosti katalizatora.
4. Postupak prema patentnom zahtjevu 3, naznačen time, da katalizator je (1) amidin kao što je DBU ili DBN, (2) tercijarni amin kao što je DABCO, trietilamin, ili DIPEA, (3) gvanidin kao što je TBD, TMG, ili MTBD, ili (4) baza kao što je NaH, KOtBu, i LiHMDS.
5. Postupak prema patentnom zahtjevu 1, naznačen time, da se spoj (IV) proizvodi putem reakcije spoja (III)
[image]
s emulzijom katalizatora u organskom otapalu ili mješavini otapala, koji se biraju iz skupine koju čine ksileni i butironitrili, u prisutnosti vodikovog plina na temperaturi od oko 70°C, kako bi se dobio spoj (IV); pri čemu se emulzija katalizatora pripravlja dodavanjem H3PO2 u emulziju od 5% Pt/C katalizatora F101 R/W i deionizirana voda prilikom miješanja, te zatim dodavanjem NH4VO3 u emulziju prilikom miješanja; s time, da se spoj (III)
[image]
proizvodi putem reakcije otopine spoja (II)
[image]
u ksilenima s natrijevim cijanidom u prisutnosti bakrenog (I) jodida u butironitrilu na temperaturi od oko 120°C, kako bi se dobio spoj (III).
6. Postupak prema patentnom zahtjevu 5, naznačen time, da se spoj (II)
[image]
proizvodi putem miješanja spoja (I):
[image]
u prisutnosti trietilamin hidrobromida, u prisutnosti DMF u ksilenima kao otopini;
dodavanjem u spoj (I) otopine fosfornog oksibromida u ksilenima; zagrijavanje do oko 100°C u trajanju oko 3 sata; zatim,
hlađenje reakcijske smjese na oko 70°C prije dodavanja NaOH, kako bi se dobio spoj (II).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462094436P | 2014-12-19 | 2014-12-19 | |
| EP18169895.2A EP3372585B1 (en) | 2014-12-19 | 2015-12-17 | Process for the preparation of a diarylthiohydantoin compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220750T1 true HRP20220750T1 (hr) | 2022-09-02 |
Family
ID=55168400
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220750TT HRP20220750T1 (hr) | 2014-12-19 | 2015-12-17 | Postupak za proizvodnju spoja diariltiohidantoina |
| HRP20190540TT HRP20190540T1 (hr) | 2014-12-19 | 2019-03-19 | Postupak za pripremu spoja diariltiohidantoina |
| HRP20201847TT HRP20201847T2 (hr) | 2014-12-19 | 2020-11-20 | Postupak za pripremu spoja diariltiohidantoina |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20190540TT HRP20190540T1 (hr) | 2014-12-19 | 2019-03-19 | Postupak za pripremu spoja diariltiohidantoina |
| HRP20201847TT HRP20201847T2 (hr) | 2014-12-19 | 2020-11-20 | Postupak za pripremu spoja diariltiohidantoina |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US9688655B2 (hr) |
| EP (4) | EP3233803B1 (hr) |
| JP (2) | JP6681902B2 (hr) |
| KR (1) | KR102586059B1 (hr) |
| AR (1) | AR103228A1 (hr) |
| AU (1) | AU2015364537B2 (hr) |
| BR (1) | BR112017013113B1 (hr) |
| CA (1) | CA2970937A1 (hr) |
| CY (2) | CY1121684T1 (hr) |
| DK (3) | DK3372585T3 (hr) |
| EA (4) | EA201892487A1 (hr) |
| ES (3) | ES2827549T3 (hr) |
| HR (3) | HRP20220750T1 (hr) |
| HU (2) | HUE052475T2 (hr) |
| IL (1) | IL252843A0 (hr) |
| LT (3) | LT3372584T (hr) |
| MA (1) | MA41200B1 (hr) |
| MD (1) | MD3233803T2 (hr) |
| ME (1) | ME03420B (hr) |
| MX (1) | MX2017008179A (hr) |
| NZ (1) | NZ732766A (hr) |
| PH (1) | PH12017501152A1 (hr) |
| PL (3) | PL3372585T3 (hr) |
| PT (3) | PT3372584T (hr) |
| RS (3) | RS61060B9 (hr) |
| SG (4) | SG10201912802XA (hr) |
| SI (3) | SI3372585T1 (hr) |
| TR (1) | TR201904739T4 (hr) |
| TW (4) | TWI703132B (hr) |
| UA (1) | UA123201C2 (hr) |
| WO (1) | WO2016100652A2 (hr) |
| ZA (1) | ZA201704877B (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS58428B1 (sr) * | 2014-12-19 | 2019-04-30 | Aragon Pharmaceuticals Inc | Postupci za pripremu jedinjenja diariltiohidantoina |
| EP3233803B1 (en) * | 2014-12-19 | 2019-01-30 | 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 |
| US10513504B2 (en) | 2018-03-08 | 2019-12-24 | Apotex Inc. | Processes for the preparation of apalutamide and intermediates thereof |
| WO2022049265A1 (en) | 2020-09-04 | 2022-03-10 | Synthon B.V. | Improved process for preparation of apalutamide |
Family Cites Families (11)
| 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 |
| 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 |
| 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 |
| PE20141375A1 (es) * | 2008-05-16 | 2014-10-23 | Takeda San Diego Inc | Activadores de glucoquinasa |
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