JP2019522662A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019522662A5 JP2019522662A5 JP2018568670A JP2018568670A JP2019522662A5 JP 2019522662 A5 JP2019522662 A5 JP 2019522662A5 JP 2018568670 A JP2018568670 A JP 2018568670A JP 2018568670 A JP2018568670 A JP 2018568670A JP 2019522662 A5 JP2019522662 A5 JP 2019522662A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- production method
- group
- alkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 30
- 238000004519 manufacturing process Methods 0.000 claims 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002560 nitrile group Chemical group 0.000 claims 4
- RTAWCKGXCGSFJI-UHFFFAOYSA-N 2,6-difluoro-3-(propylsulfonylamino)benzoic acid Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(O)=O)=C1F RTAWCKGXCGSFJI-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 230000000911 decarboxylating effect Effects 0.000 claims 3
- 238000006114 decarboxylation reaction Methods 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 101150003085 Pdcl gene Proteins 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims 1
- 229910020808 NaBF Inorganic materials 0.000 claims 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 0 *c(cc1)ccc1Cl Chemical compound *c(cc1)ccc1Cl 0.000 description 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20165557 | 2016-07-01 | ||
| FI20165557 | 2016-07-01 | ||
| FI20165778 | 2016-10-12 | ||
| FI20165778 | 2016-10-12 | ||
| PCT/FI2017/000012 WO2018002415A1 (en) | 2016-07-01 | 2017-06-30 | New processes for the preparation of vemurafenib |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019522662A JP2019522662A (ja) | 2019-08-15 |
| JP2019522662A5 true JP2019522662A5 (enExample) | 2020-07-02 |
| JP6911062B2 JP6911062B2 (ja) | 2021-07-28 |
Family
ID=59416718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018568670A Expired - Fee Related JP6911062B2 (ja) | 2016-07-01 | 2017-06-30 | ベムラフェニブの新規な製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10407427B2 (enExample) |
| EP (1) | EP3478684B1 (enExample) |
| JP (1) | JP6911062B2 (enExample) |
| CA (1) | CA3029361A1 (enExample) |
| ES (1) | ES2802476T3 (enExample) |
| HR (1) | HRP20200821T1 (enExample) |
| HU (1) | HUE049682T2 (enExample) |
| PL (1) | PL3478684T3 (enExample) |
| RS (1) | RS60451B1 (enExample) |
| WO (1) | WO2018002415A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2928773T3 (es) | 2017-01-17 | 2022-11-22 | Heparegenix Gmbh | Inhibidores de proteína cinasas para fomentar la regeneración hepática o reducir o prevenir la muerte de hepatocitos |
| DK3860598T3 (da) | 2018-10-03 | 2023-10-16 | Jyvaeskylaen Yliopisto | Vemurafenib og salte heraf til anvendelse til behandling af enterovirusinfektioner |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1303759B1 (it) * | 1998-11-17 | 2001-02-23 | Dompe Spa | Procedimento migliorato per la preparazione di acido 7-azaindolil-3-carbossilico. |
| PT1893612E (pt) | 2005-06-22 | 2011-11-21 | Plexxikon Inc | Derivados de pirrolo [2,3-b]piridina como inibidores de proteína quinase |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| US8779150B2 (en) | 2010-07-21 | 2014-07-15 | Hoffmann-La Roche Inc. | Processes for the manufacture of propane-1-sulfonic acid {3-[5-(4-chloro-phenyl)-1 H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide |
| EA028351B1 (ru) | 2013-03-14 | 2017-11-30 | Ратиофарм Гмбх | Твердые формы гидрохлорида вемурафениба |
| WO2015075749A1 (en) | 2013-11-22 | 2015-05-28 | Laurus Labs Private Limited | Novel processes for the preparation of vemurafenib |
| CZ2013943A3 (cs) | 2013-11-27 | 2015-06-03 | Zentiva, K.S. | Krystalické formy vemurafenibu |
| US10414764B2 (en) | 2014-11-29 | 2019-09-17 | Shilpa Medicare Limited | Substantially pure vemurafenib and its salts |
-
2017
- 2017-06-30 RS RS20200741A patent/RS60451B1/sr unknown
- 2017-06-30 PL PL17745368T patent/PL3478684T3/pl unknown
- 2017-06-30 US US16/313,597 patent/US10407427B2/en not_active Expired - Fee Related
- 2017-06-30 EP EP17745368.5A patent/EP3478684B1/en active Active
- 2017-06-30 ES ES17745368T patent/ES2802476T3/es active Active
- 2017-06-30 CA CA3029361A patent/CA3029361A1/en active Pending
- 2017-06-30 HR HRP20200821TT patent/HRP20200821T1/hr unknown
- 2017-06-30 HU HUE17745368A patent/HUE049682T2/hu unknown
- 2017-06-30 WO PCT/FI2017/000012 patent/WO2018002415A1/en not_active Ceased
- 2017-06-30 JP JP2018568670A patent/JP6911062B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Birkholz et al. | Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions | |
| HRP20190769T1 (hr) | Postupak proizvodnje 1-[2-(2,4-dimetilfenilsulfanil)fenil]piperazina | |
| JP2018527367A5 (enExample) | ||
| JP2019522662A5 (enExample) | ||
| JP2009541363A5 (enExample) | ||
| JP2004189841A5 (enExample) | ||
| JP2015517977A5 (enExample) | ||
| JP2013508368A5 (enExample) | ||
| JP2010539155A5 (enExample) | ||
| AU2018260728A1 (en) | Process for the preparation of deuterated ethanol from D2 | |
| JP2017533234A (ja) | ルテニウム触媒作用によるアゾベンゾール類からのビフェニルアミン類の製造方法 | |
| JP2019189529A5 (enExample) | ||
| CN103664602A (zh) | 一种α, β-不饱和羧酸酯类化合物及其制备方法 | |
| HRP20200821T1 (hr) | Novi procesi za pripremu vemurafeniba | |
| CN118176175A (zh) | 含全氟烷基的芳香族化合物的制造方法 | |
| SanMartin et al. | Mizoroki Heck and Sonogashira Cross‐Couplings Catalyzed by CNC Palladium Pincer Complexes in Organic and Aqueous Media | |
| AR069759A1 (es) | Proceso de intermediarios utiles en la preparacion de 5-(etil- dihidro-1-h-inden-2-il) 1h- imidazola | |
| CN111170971B (zh) | 一种以邻氯甲苯为原料合成苯并呋喃酮的方法 | |
| JP2010511044A5 (enExample) | ||
| JP2019112400A5 (enExample) | ||
| JP2005511667A5 (enExample) | ||
| CN103965057B (zh) | 一种腈制备伯胺的方法 | |
| JP5155148B2 (ja) | ６−［３−（１−アダマンチル）−４−メトキシフェニル］−２−ナフトエ酸の合成方法 | |
| CN102311351B (zh) | 一种2,4-二甲氧基苄胺的合成方法 | |
| JP2002308835A (ja) | テルビナフィンの製造方法 |