JP2014196365A5 - - Google Patents
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- JP2014196365A5 JP2014196365A5 JP2014148858A JP2014148858A JP2014196365A5 JP 2014196365 A5 JP2014196365 A5 JP 2014196365A5 JP 2014148858 A JP2014148858 A JP 2014148858A JP 2014148858 A JP2014148858 A JP 2014148858A JP 2014196365 A5 JP2014196365 A5 JP 2014196365A5
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- JP
- Japan
- Prior art keywords
- formula
- solvent
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- compound
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- -1 5-bromopyrrole compound Chemical class 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007810 chemical reaction solvent Substances 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000004210 ether based solvent Substances 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 238000005804 alkylation reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 230000002152 alkylating effect Effects 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- POVNYOLUWDFQOZ-UHFFFAOYSA-N 4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide Chemical compound CC1OS(=O)(=O)OC1C POVNYOLUWDFQOZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- SAQAERNKMHATDZ-UHFFFAOYSA-N 2-bromo-1h-pyrrole Chemical compound BrC1=CC=CN1 SAQAERNKMHATDZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10371508P | 2008-10-08 | 2008-10-08 | |
| US61/103,715 | 2008-10-08 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531140A Division JP5767586B2 (ja) | 2008-10-08 | 2009-10-07 | （ヒドロキシアルキル）ピロール誘導体のアトロプ異性体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014196365A JP2014196365A (ja) | 2014-10-16 |
| JP2014196365A5 true JP2014196365A5 (enExample) | 2015-12-10 |
| JP6121952B2 JP6121952B2 (ja) | 2017-04-26 |
Family
ID=41360127
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531140A Active JP5767586B2 (ja) | 2008-10-08 | 2009-10-07 | （ヒドロキシアルキル）ピロール誘導体のアトロプ異性体 |
| JP2014148858A Active JP6121952B2 (ja) | 2008-10-08 | 2014-07-22 | （ヒドロキシアルキル）ピロール誘導体のアトロプ異性体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531140A Active JP5767586B2 (ja) | 2008-10-08 | 2009-10-07 | （ヒドロキシアルキル）ピロール誘導体のアトロプ異性体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8487117B2 (enExample) |
| EP (1) | EP2349997B1 (enExample) |
| JP (2) | JP5767586B2 (enExample) |
| KR (1) | KR101643285B1 (enExample) |
| CN (1) | CN102186817B (enExample) |
| AU (1) | AU2009302371B2 (enExample) |
| BR (1) | BRPI0920459B1 (enExample) |
| CA (1) | CA2736923C (enExample) |
| ES (1) | ES2547697T3 (enExample) |
| IL (1) | IL212170A (enExample) |
| TW (2) | TWI547479B (enExample) |
| WO (1) | WO2010042622A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102226982B1 (ko) * | 2013-08-27 | 2021-03-11 | 다이이찌 산쿄 가부시키가이샤 | 피롤 유도체의 제조 방법 및 그 중간체 |
| US12527763B2 (en) | 2019-10-25 | 2026-01-20 | Sunshine Lake Pharma Co., Ltd. | Pyrrole amide compound and use thereof |
| US20240376051A1 (en) * | 2021-03-30 | 2024-11-14 | Sunshine Lake Pharma Co., Ltd. | Crystalline form of pyrrole amide compound, preparation method therefor and use thereof |
| CN115784961A (zh) * | 2021-09-10 | 2023-03-14 | 上海鼎雅药物化学科技有限公司 | 埃沙西林酮及其中间体的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1773768B8 (en) * | 2004-07-30 | 2018-12-26 | Exelixis, Inc. | Pyrrole derivatives as pharmaceutical agents |
| PL2133330T3 (pl) * | 2007-04-09 | 2014-06-30 | Daiichi Sankyo Co Ltd | Atropoizomer pochodnej pirolu |
-
2009
- 2009-10-07 EP EP09737501.8A patent/EP2349997B1/en active Active
- 2009-10-07 JP JP2011531140A patent/JP5767586B2/ja active Active
- 2009-10-07 KR KR1020117010427A patent/KR101643285B1/ko active Active
- 2009-10-07 CN CN200980139822.5A patent/CN102186817B/zh active Active
- 2009-10-07 ES ES09737501.8T patent/ES2547697T3/es active Active
- 2009-10-07 WO PCT/US2009/059847 patent/WO2010042622A1/en not_active Ceased
- 2009-10-07 BR BRPI0920459-8A patent/BRPI0920459B1/pt active IP Right Grant
- 2009-10-07 US US13/122,147 patent/US8487117B2/en active Active
- 2009-10-07 CA CA2736923A patent/CA2736923C/en active Active
- 2009-10-07 AU AU2009302371A patent/AU2009302371B2/en active Active
- 2009-10-08 TW TW098134174A patent/TWI547479B/zh active
- 2009-10-08 TW TW104142529A patent/TWI593674B/zh active
-
2011
- 2011-04-06 IL IL212170A patent/IL212170A/en active IP Right Grant
-
2014
- 2014-07-22 JP JP2014148858A patent/JP6121952B2/ja active Active
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