JP2019508387A5 - - Google Patents
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- Publication number
- JP2019508387A5 JP2019508387A5 JP2018538156A JP2018538156A JP2019508387A5 JP 2019508387 A5 JP2019508387 A5 JP 2019508387A5 JP 2018538156 A JP2018538156 A JP 2018538156A JP 2018538156 A JP2018538156 A JP 2018538156A JP 2019508387 A5 JP2019508387 A5 JP 2019508387A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- process according
- palladium
- platinum
- salt
- 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
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- 238000000034 method Methods 0.000 claims 21
- 239000002253 acid Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 7
- 229960003278 osimertinib Drugs 0.000 claims 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 6
- DUYJMQONPNNFPI-UHFFFAOYSA-N osimertinib Chemical compound COC1=CC(N(C)CCN(C)C)=C(NC(=O)C=C)C=C1NC1=NC=CC(C=2C3=CC=CC=C3N(C)C=2)=N1 DUYJMQONPNNFPI-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 4
- 239000002243 precursor Chemical class 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical group ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- -1 AZD9291 compound Chemical class 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662289390P | 2016-02-01 | 2016-02-01 | |
| US62/289,390 | 2016-02-01 | ||
| PCT/EP2017/052050 WO2017134051A1 (en) | 2016-02-01 | 2017-01-31 | Improved process for the preparation of osimertinib (azd9291) or a salt thereof, and "azd9291 aniline" or a salt thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019508387A JP2019508387A (ja) | 2019-03-28 |
| JP2019508387A5 true JP2019508387A5 (enExample) | 2020-01-30 |
| JP6812449B2 JP6812449B2 (ja) | 2021-01-13 |
Family
ID=57984913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018538156A Active JP6812449B2 (ja) | 2016-02-01 | 2017-01-31 | オシメルチニブ（ａｚｄ９２９１）またはその塩、および「ａｚｄ９２９１アニリン」またはその塩を製造するための向上したプロセス |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US11180477B2 (enExample) |
| EP (1) | EP3411038B1 (enExample) |
| JP (1) | JP6812449B2 (enExample) |
| KR (1) | KR102749892B1 (enExample) |
| CN (1) | CN108495632B (enExample) |
| AR (1) | AR107494A1 (enExample) |
| AU (1) | AU2017214243B2 (enExample) |
| BR (1) | BR112018014712B1 (enExample) |
| CA (1) | CA3011809C (enExample) |
| CO (1) | CO2018007008A2 (enExample) |
| ES (1) | ES2834608T3 (enExample) |
| IL (1) | IL260665B (enExample) |
| MX (1) | MX378363B (enExample) |
| MY (1) | MY185367A (enExample) |
| RU (1) | RU2733376C2 (enExample) |
| TW (1) | TWI745345B (enExample) |
| WO (1) | WO2017134051A1 (enExample) |
| ZA (1) | ZA201805790B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102444835B1 (ko) | 2016-05-26 | 2022-09-19 | 리커리엄 아이피 홀딩스, 엘엘씨 | Egfr 억제제 화합물 |
| CN107556293B (zh) * | 2017-09-19 | 2019-12-03 | 福建省微生物研究所 | 一种奥西替尼的合成工艺 |
| WO2021111462A1 (en) * | 2019-12-02 | 2021-06-10 | Natco Pharma Limited | An improved process for the preparation of osimertinib mesylate |
| US11780824B2 (en) * | 2020-12-16 | 2023-10-10 | Scinopharm Taiwan, Ltd. | Process for preparing osimertinib or a salt thereof |
| JP2024530782A (ja) | 2021-09-02 | 2024-08-23 | シントン・ビー．ブイ． | オシメルチニブの製造方法 |
| WO2025124936A1 (en) | 2023-12-15 | 2025-06-19 | Synthon B.V. | A process for making osimertinib |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070401A (en) * | 1972-02-19 | 1978-01-24 | Mitsui Toatsu Chemicals Inc. | Method for the preparation of a halogenated aromatic amine |
| BR112014001768B1 (pt) * | 2011-07-27 | 2019-02-05 | Astrazeneca Ab | composto n-(2-{2-dimetilaminoetil-metilamino}-4-metóxi-5-{[4-(1-metilindol-3-il) pirimidin-2-il]amino}fenil) prop-2-enamida ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica e uso do dito composto |
| DK3157916T3 (en) | 2014-06-19 | 2019-03-18 | Ariad Pharma Inc | HETEROARYL COMPOUNDS FOR CHINESE INHIBITION |
| CN104817541B (zh) * | 2015-05-11 | 2017-06-16 | 苏州东南药业股份有限公司 | 一种抗肿瘤药物的合成方法 |
-
2017
- 2017-01-26 TW TW106103351A patent/TWI745345B/zh active
- 2017-01-31 ES ES17703696T patent/ES2834608T3/es active Active
- 2017-01-31 CA CA3011809A patent/CA3011809C/en active Active
- 2017-01-31 MX MX2018008966A patent/MX378363B/es unknown
- 2017-01-31 KR KR1020187025038A patent/KR102749892B1/ko active Active
- 2017-01-31 US US16/074,119 patent/US11180477B2/en active Active
- 2017-01-31 BR BR112018014712-5A patent/BR112018014712B1/pt active IP Right Grant
- 2017-01-31 RU RU2018130327A patent/RU2733376C2/ru active
- 2017-01-31 WO PCT/EP2017/052050 patent/WO2017134051A1/en not_active Ceased
- 2017-01-31 AR ARP170100246A patent/AR107494A1/es unknown
- 2017-01-31 MY MYPI2018702645A patent/MY185367A/en unknown
- 2017-01-31 AU AU2017214243A patent/AU2017214243B2/en active Active
- 2017-01-31 EP EP17703696.9A patent/EP3411038B1/en active Active
- 2017-01-31 JP JP2018538156A patent/JP6812449B2/ja active Active
- 2017-01-31 CN CN201780007929.9A patent/CN108495632B/zh active Active
-
2018
- 2018-07-04 CO CONC2018/0007008A patent/CO2018007008A2/es unknown
- 2018-07-19 IL IL260665A patent/IL260665B/en unknown
- 2018-08-29 ZA ZA2018/05790A patent/ZA201805790B/en unknown
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