JP2015527345A5 - - Google Patents
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- Publication number
- JP2015527345A5 JP2015527345A5 JP2015525826A JP2015525826A JP2015527345A5 JP 2015527345 A5 JP2015527345 A5 JP 2015527345A5 JP 2015525826 A JP2015525826 A JP 2015525826A JP 2015525826 A JP2015525826 A JP 2015525826A JP 2015527345 A5 JP2015527345 A5 JP 2015527345A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amino acid
- hydrogen
- ester
- solvent
- 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
- 238000000034 method Methods 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 108090000371 Esterases Proteins 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000003275 alpha amino acid group Chemical group 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000002244 precipitate Substances 0.000 claims 5
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229920001184 polypeptide Polymers 0.000 claims 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- -1 propionate ester Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 230000002255 enzymatic effect Effects 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- ZTWQHVRMOJLGRW-GXFFZTMASA-N (2r,3r)-3-hydroxy-2-methyl-3-phenyl-4-(1,2,4-triazol-1-yl)butanoic acid Chemical compound C([C@@](O)([C@H](C(O)=O)C)C=1C=CC=CC=1)N1C=NC=N1 ZTWQHVRMOJLGRW-GXFFZTMASA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical class CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 238000006680 Reformatsky reaction Methods 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001649 bromium compounds Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12179540.5 | 2012-08-07 | ||
| EP12179540 | 2012-08-07 | ||
| PCT/EP2013/066071 WO2014023623A1 (en) | 2012-08-07 | 2013-07-31 | Process for the manufacture of isavuconazole or ravuconazole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015527345A JP2015527345A (ja) | 2015-09-17 |
| JP2015527345A5 true JP2015527345A5 (OSRAM) | 2016-09-15 |
| JP6334529B2 JP6334529B2 (ja) | 2018-05-30 |
Family
ID=48979725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015525826A Active JP6334529B2 (ja) | 2012-08-07 | 2013-07-31 | イサブコナゾールまたはラブコナゾールの製造方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9783508B2 (OSRAM) |
| EP (1) | EP2882723B1 (OSRAM) |
| JP (1) | JP6334529B2 (OSRAM) |
| KR (1) | KR102129150B1 (OSRAM) |
| CN (1) | CN104507917B (OSRAM) |
| BR (1) | BR112015002526B1 (OSRAM) |
| CA (1) | CA2878361C (OSRAM) |
| ES (1) | ES2616412T3 (OSRAM) |
| HR (1) | HRP20170171T1 (OSRAM) |
| HU (1) | HUE031679T2 (OSRAM) |
| MX (1) | MX360783B (OSRAM) |
| PL (1) | PL2882723T3 (OSRAM) |
| PT (1) | PT2882723T (OSRAM) |
| SI (1) | SI2882723T1 (OSRAM) |
| WO (1) | WO2014023623A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801500B (zh) * | 2014-12-31 | 2018-08-24 | 四川科伦药物研究院有限公司 | 拆分艾沙康唑中间化合物消旋体的方法 |
| CN106317044A (zh) * | 2015-06-30 | 2017-01-11 | 刘玫君 | 一种制造艾沙康唑或雷夫康唑的方法 |
| CN104961695A (zh) * | 2015-07-27 | 2015-10-07 | 成都塞恩斯医药科技有限公司 | 一种艾沙康唑和雷夫康唑中间体的制备方法 |
| CN106467534B (zh) * | 2015-08-17 | 2019-10-11 | 江苏奥赛康药业有限公司 | 一种硫酸艾沙康唑鎓化合物及其药物组合物 |
| CN105907832B (zh) * | 2015-12-02 | 2019-07-12 | 成都师范学院 | 一种酶法拆分艾沙康唑中间体的方法 |
| CN105777740B (zh) * | 2016-02-24 | 2018-03-27 | 苏州金点生物科技有限公司 | 一种艾沙康唑的制备方法 |
| CA3061133A1 (en) | 2017-04-27 | 2018-11-01 | Codexis, Inc. | Ketoreductase polypeptides and polynucleotides |
| WO2021245590A1 (en) * | 2020-06-04 | 2021-12-09 | Metrochem Api Private Limited | An improved process for the preparation of triazole derivatives |
| CN111574444A (zh) * | 2020-07-07 | 2020-08-25 | 安徽贝克生物制药有限公司 | 一种贝达喹啉的制备方法 |
| CN116478103B (zh) * | 2023-03-24 | 2025-07-25 | 四川澄华生物科技有限公司 | 一种拆分艾沙康唑中间体4的方法 |
| CN119661453B (zh) * | 2025-02-17 | 2025-04-22 | 四川澄华生物科技有限公司 | 一种制备艾沙康唑的主链中间体的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8510195D0 (en) * | 1985-04-22 | 1985-05-30 | Ici Plc | Heterocyclic compounds |
| US5134152A (en) | 1989-12-07 | 1992-07-28 | Sankyo Company, Limited | Oxetane derivatives and their use as anti-fungal or fungicidal agents |
| JP2887523B2 (ja) * | 1990-11-30 | 1999-04-26 | 富山化学工業株式会社 | 新規なトリアゾール誘導体およびその塩 |
| GB9107055D0 (en) * | 1991-04-04 | 1991-05-22 | Pfizer Ltd | Triazole antifungal agents |
| JP4208269B2 (ja) * | 1996-10-01 | 2009-01-14 | 東芝ソリューション株式会社 | 異種物混入検査方法及びそのシステム |
| WO1999002524A1 (en) | 1997-07-08 | 1999-01-21 | Sankyo Company, Limited | Antifungal triazole compounds |
| WO1999045008A1 (en) | 1998-03-06 | 1999-09-10 | F. Hoffmann-La Roche Ag | 3-[4-(4-cyanophenyl)thiazol-2-y)]-1-(1h-1,2,4-triazol-1-yl)-butan-2-ol derivatives having antifungal activity |
| AU2002321068B2 (en) * | 2001-06-26 | 2007-11-15 | Basilea Pharmaceutica Ag | Intermediate halophenyl derivatives and their use in a process for preparing azole derivatives |
| KR101191682B1 (ko) | 2005-12-01 | 2012-10-16 | 바실리어 파마슈티카 아게 | 에폭시부탄올 중간체의 제조 방법 |
| PL2171061T3 (pl) | 2007-07-04 | 2019-03-29 | Patheon Austria Gmbh & Co Kg | Preparat esterazy |
| GB0712972D0 (en) | 2007-07-04 | 2007-08-15 | Glaxosmithkline Consumer Healt | Formulation |
| CN101855229A (zh) | 2007-09-12 | 2010-10-06 | 埃迪威克斯生物科学公司 | 作为gsk-3抑制剂的螺环状氨基喹诺酮 |
| CA2727340A1 (en) * | 2008-06-25 | 2009-12-30 | Daiichi Sankyo Company, Limited | Carboxylic acid compound |
| PT2298747T (pt) | 2008-07-03 | 2017-02-06 | Astellas Pharma Inc | Derivado de triazole ou um seu sal |
| ES2689941T3 (es) | 2009-04-24 | 2018-11-16 | Patheon Austria Gmbh & Co Kg | Esterasas de hígado de cerdo mejoradas |
| US8207352B2 (en) * | 2009-10-08 | 2012-06-26 | Drug Process Licensing Associates LLC | Process for the manufacture of enantiomerically pure antifungal azoles as ravuconazole and isavuconazole |
| WO2011145669A1 (ja) * | 2010-05-19 | 2011-11-24 | 大日本住友製薬株式会社 | アミド誘導体 |
-
2013
- 2013-07-31 HU HUE13747999A patent/HUE031679T2/en unknown
- 2013-07-31 CA CA2878361A patent/CA2878361C/en active Active
- 2013-07-31 SI SI201330513A patent/SI2882723T1/sl unknown
- 2013-07-31 CN CN201380038886.2A patent/CN104507917B/zh active Active
- 2013-07-31 KR KR1020157001779A patent/KR102129150B1/ko active Active
- 2013-07-31 PL PL13747999T patent/PL2882723T3/pl unknown
- 2013-07-31 WO PCT/EP2013/066071 patent/WO2014023623A1/en not_active Ceased
- 2013-07-31 MX MX2015000744A patent/MX360783B/es active IP Right Grant
- 2013-07-31 JP JP2015525826A patent/JP6334529B2/ja active Active
- 2013-07-31 EP EP13747999.4A patent/EP2882723B1/en active Active
- 2013-07-31 BR BR112015002526-9A patent/BR112015002526B1/pt active IP Right Grant
- 2013-07-31 HR HRP20170171TT patent/HRP20170171T1/hr unknown
- 2013-07-31 PT PT137479994T patent/PT2882723T/pt unknown
- 2013-07-31 ES ES13747999.4T patent/ES2616412T3/es active Active
- 2013-07-31 US US14/419,153 patent/US9783508B2/en active Active
-
2017
- 2017-09-11 US US15/700,647 patent/US10590092B2/en active Active
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