JP2016500657A5 - - Google Patents
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- Publication number
- JP2016500657A5 JP2016500657A5 JP2015534641A JP2015534641A JP2016500657A5 JP 2016500657 A5 JP2016500657 A5 JP 2016500657A5 JP 2015534641 A JP2015534641 A JP 2015534641A JP 2015534641 A JP2015534641 A JP 2015534641A JP 2016500657 A5 JP2016500657 A5 JP 2016500657A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- added
- ethyl acetate
- mixture
- sme
- 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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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000008057 potassium phosphate buffer Substances 0.000 description 3
- QWPXBEHQFHACTK-KZVYIGENSA-N (10e,12e)-86-chloro-12,14,4-trihydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-15,16-dihydro-14h-7-aza-1(6,4)-oxazina-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-6-one Chemical compound CN1C(=O)CC(O)C2(C)OC2C(C)C(OC(=O)N2)CC2(O)C(OC)\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 QWPXBEHQFHACTK-KZVYIGENSA-N 0.000 description 2
- WTFJJYYGWFKOQH-VKHMYHEASA-N (4s)-3,4-dimethyl-1,3-oxazolidine-2,5-dione Chemical compound C[C@@H]1N(C)C(=O)OC1=O WTFJJYYGWFKOQH-VKHMYHEASA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930126263 Maytansine Natural products 0.000 description 2
- QWPXBEHQFHACTK-UHFFFAOYSA-N Maytansinol Natural products CN1C(=O)CC(O)C2(C)OC2C(C)C(OC(=O)N2)CC2(O)C(OC)C=CC=C(C)CC2=CC(OC)=C(Cl)C1=C2 QWPXBEHQFHACTK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- BPOPGHPHBCLJOK-UHFFFAOYSA-N butanedithioic acid Chemical compound CCCC(S)=S BPOPGHPHBCLJOK-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261705731P | 2012-09-26 | 2012-09-26 | |
| US61/705,731 | 2012-09-26 | ||
| PCT/US2013/061839 WO2014052537A1 (en) | 2012-09-26 | 2013-09-26 | Improved methods for the acylation of maytansinol |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018032684A Division JP2018109044A (ja) | 2012-09-26 | 2018-02-27 | マイタンシノールをアシル化する改善された方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016500657A JP2016500657A (ja) | 2016-01-14 |
| JP2016500657A5 true JP2016500657A5 (enExample) | 2018-04-12 |
| JP6517693B2 JP6517693B2 (ja) | 2019-05-22 |
Family
ID=49328648
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015534641A Active JP6517693B2 (ja) | 2012-09-26 | 2013-09-26 | マイタンシノールをアシル化する改善された方法 |
| JP2018032684A Ceased JP2018109044A (ja) | 2012-09-26 | 2018-02-27 | マイタンシノールをアシル化する改善された方法 |
| JP2020068137A Active JP6735000B1 (ja) | 2012-09-26 | 2020-04-06 | マイタンシノールをアシル化する改善された方法 |
| JP2020118929A Pending JP2020180150A (ja) | 2012-09-26 | 2020-07-10 | マイタンシノールをアシル化する改善された方法 |
| JP2022029253A Pending JP2022068367A (ja) | 2012-09-26 | 2022-02-28 | マイタンシノールをアシル化する改善された方法 |
| JP2023181529A Pending JP2024010055A (ja) | 2012-09-26 | 2023-10-23 | マイタンシノールをアシル化する改善された方法 |
| JP2025058629A Pending JP2025098242A (ja) | 2012-09-26 | 2025-03-31 | マイタンシノールをアシル化する改善された方法 |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018032684A Ceased JP2018109044A (ja) | 2012-09-26 | 2018-02-27 | マイタンシノールをアシル化する改善された方法 |
| JP2020068137A Active JP6735000B1 (ja) | 2012-09-26 | 2020-04-06 | マイタンシノールをアシル化する改善された方法 |
| JP2020118929A Pending JP2020180150A (ja) | 2012-09-26 | 2020-07-10 | マイタンシノールをアシル化する改善された方法 |
| JP2022029253A Pending JP2022068367A (ja) | 2012-09-26 | 2022-02-28 | マイタンシノールをアシル化する改善された方法 |
| JP2023181529A Pending JP2024010055A (ja) | 2012-09-26 | 2023-10-23 | マイタンシノールをアシル化する改善された方法 |
| JP2025058629A Pending JP2025098242A (ja) | 2012-09-26 | 2025-03-31 | マイタンシノールをアシル化する改善された方法 |
Country Status (27)
| Country | Link |
|---|---|
| US (9) | US9012629B2 (enExample) |
| EP (3) | EP2900676B1 (enExample) |
| JP (7) | JP6517693B2 (enExample) |
| CN (2) | CN108586487B (enExample) |
| AU (4) | AU2013323572B2 (enExample) |
| BR (2) | BR122021022582B1 (enExample) |
| CA (2) | CA2884873C (enExample) |
| CY (2) | CY1121415T1 (enExample) |
| DK (2) | DK2900676T3 (enExample) |
| ES (2) | ES2716561T3 (enExample) |
| HR (2) | HRP20190473T1 (enExample) |
| HU (2) | HUE043285T2 (enExample) |
| IL (2) | IL237899A (enExample) |
| LT (2) | LT3486248T (enExample) |
| MX (2) | MX366701B (enExample) |
| MY (1) | MY169250A (enExample) |
| NZ (2) | NZ739573A (enExample) |
| PL (2) | PL3486248T3 (enExample) |
| PT (2) | PT2900676T (enExample) |
| RS (2) | RS58493B1 (enExample) |
| RU (2) | RU2648992C2 (enExample) |
| SG (1) | SG11201501918UA (enExample) |
| SI (2) | SI2900676T1 (enExample) |
| SM (2) | SMT201900170T1 (enExample) |
| TR (1) | TR201903625T4 (enExample) |
| WO (1) | WO2014052537A1 (enExample) |
| ZA (1) | ZA201501898B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE043285T2 (hu) * | 2012-09-26 | 2019-08-28 | Immunogen Inc | Javított eljárás maytansinol acilezésére |
| CN105585579A (zh) * | 2014-10-24 | 2016-05-18 | 南京联宁生物制药有限公司 | 一种化合物及其制备方法以及美登素dm1的制备方法 |
| AU2016233227B2 (en) | 2015-03-17 | 2020-03-12 | Regeneron Pharmaceuticals, Inc. | Amino acid acylation reagents and methods of using the same |
| JP7350313B2 (ja) | 2016-12-16 | 2023-09-26 | ブルーフィン バイオメディシン， インコーポレイテッド | 抗ｃｕｂドメイン含有タンパク質１（ｃｄｃｐ１）抗体、抗体薬物コンジュゲート、およびその使用方法 |
| PL3956332T3 (pl) | 2019-04-18 | 2023-05-29 | Indena S.P.A. | Diastereoselektywny sposób wytwarzania estrów majtanzynoidowych zawierających tiol lub dwusiarczek i ich produkty pośrednie |
| EP4067497A4 (en) | 2019-11-29 | 2024-03-13 | MicroBiopharm Japan Co., Ltd. | Method for enzymatically producing maytansinol |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4151042A (en) | 1977-03-31 | 1979-04-24 | Takeda Chemical Industries, Ltd. | Method for producing maytansinol and its derivatives |
| JPS6034556B2 (ja) * | 1977-03-31 | 1985-08-09 | 武田薬品工業株式会社 | 抗生物質ｃ−１５００３ |
| US4137230A (en) | 1977-11-14 | 1979-01-30 | Takeda Chemical Industries, Ltd. | Method for the production of maytansinoids |
| US4265814A (en) | 1978-03-24 | 1981-05-05 | Takeda Chemical Industries | Matansinol 3-n-hexadecanoate |
| JPS5562090A (en) | 1978-10-27 | 1980-05-10 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| JPS5566585A (en) | 1978-11-14 | 1980-05-20 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| JPS55164687A (en) | 1979-06-11 | 1980-12-22 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| JPS55162791A (en) | 1979-06-05 | 1980-12-18 | Takeda Chem Ind Ltd | Antibiotic c-15003pnd and its preparation |
| JPS55164685A (en) | 1979-06-08 | 1980-12-22 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| JPS55164686A (en) | 1979-06-11 | 1980-12-22 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| US4309428A (en) | 1979-07-30 | 1982-01-05 | Takeda Chemical Industries, Ltd. | Maytansinoids |
| JPS5622790A (en) * | 1979-07-31 | 1981-03-03 | Takeda Chem Ind Ltd | Novel maytansinoid compound and its preparation |
| JPS5645483A (en) | 1979-09-19 | 1981-04-25 | Takeda Chem Ind Ltd | C-15003phm and its preparation |
| JP3054741B2 (ja) * | 1989-09-29 | 2000-06-19 | 武田薬品工業株式会社 | Ｔａｎ―１３１３およびそのアシル誘導体 |
| US5208020A (en) | 1989-10-25 | 1993-05-04 | Immunogen Inc. | Cytotoxic agents comprising maytansinoids and their therapeutic use |
| EP1229934B1 (en) * | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| US6441163B1 (en) | 2001-05-31 | 2002-08-27 | Immunogen, Inc. | Methods for preparation of cytotoxic conjugates of maytansinoids and cell binding agents |
| TWI298067B (en) * | 2002-01-31 | 2008-06-21 | Daiso Co Ltd | New optically active compound, method for kinetic resolution of carbonic acid derivatives and catalyst thereof |
| US8088387B2 (en) | 2003-10-10 | 2012-01-03 | Immunogen Inc. | Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates |
| PL1651162T3 (pl) * | 2003-05-20 | 2016-04-29 | Immunogen Inc | Maitansynoidy w leczeniu nowotworów |
| CN1894259A (zh) * | 2003-08-22 | 2007-01-10 | 活跃生物工艺学公司 | 利福霉素类似物及其应用 |
| ES2579805T3 (es) | 2004-09-23 | 2016-08-16 | Genentech, Inc. | Anticuerpos y conjugados modificados por ingeniería genética con cisteína |
| WO2006062779A2 (en) * | 2004-12-09 | 2006-06-15 | Centocor, Inc. | Anti-integrin immunoconjugates, methods and uses |
| US7301019B2 (en) * | 2005-01-21 | 2007-11-27 | Immunogen, Inc. | Method for the preparation of maytansinoid esters |
| WO2007011721A1 (en) * | 2005-07-15 | 2007-01-25 | Kalypsys, Inc. | Inhibitors of mitotic kinesin |
| JP5167130B2 (ja) * | 2005-08-09 | 2013-03-21 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | キラルアミノ酸を有するメイタンシノールのアシル化方法 |
| US20090082386A1 (en) * | 2006-11-06 | 2009-03-26 | Erzsebet Meszarosne Sos | Ascomycin and pimecrolimus having reduced levels of desmethylascomycin and 32-deoxy-32-epichloro-desmethylascomycin respectively, and methods for preparation thereof |
| JP2008288289A (ja) | 2007-05-16 | 2008-11-27 | Oki Electric Ind Co Ltd | 電界効果トランジスタとその製造方法 |
| ME03479B (me) | 2009-06-03 | 2020-01-20 | Immunogen Inc | Metodi konjugacije |
| WO2011051960A2 (en) * | 2009-09-25 | 2011-05-05 | Cadila Healthcare Limited | Process for the preparation of rapamycin derivatives |
| ES2544608T3 (es) * | 2010-11-17 | 2015-09-02 | Genentech, Inc. | Conjugados de anticuerpo y de alaninil-maitansinol |
| HUE043285T2 (hu) * | 2012-09-26 | 2019-08-28 | Immunogen Inc | Javított eljárás maytansinol acilezésére |
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2013
- 2013-09-26 HU HUE13774881A patent/HUE043285T2/hu unknown
- 2013-09-26 EP EP13774881.0A patent/EP2900676B1/en active Active
- 2013-09-26 RS RS20190314A patent/RS58493B1/sr unknown
- 2013-09-26 LT LTEP18213678.8T patent/LT3486248T/lt unknown
- 2013-09-26 PL PL18213678T patent/PL3486248T3/pl unknown
- 2013-09-26 PL PL13774881T patent/PL2900676T3/pl unknown
- 2013-09-26 HU HUE18213678A patent/HUE055443T2/hu unknown
- 2013-09-26 LT LTEP13774881.0T patent/LT2900676T/lt unknown
- 2013-09-26 PT PT13774881T patent/PT2900676T/pt unknown
- 2013-09-26 MX MX2015003745A patent/MX366701B/es active IP Right Grant
- 2013-09-26 NZ NZ73957313A patent/NZ739573A/en unknown
- 2013-09-26 DK DK13774881.0T patent/DK2900676T3/en active
- 2013-09-26 PT PT182136788T patent/PT3486248T/pt unknown
- 2013-09-26 EP EP21166484.2A patent/EP3904358A1/en active Pending
- 2013-09-26 SI SI201331374T patent/SI2900676T1/sl unknown
- 2013-09-26 CN CN201810251853.0A patent/CN108586487B/zh active Active
- 2013-09-26 EP EP18213678.8A patent/EP3486248B1/en active Active
- 2013-09-26 AU AU2013323572A patent/AU2013323572B2/en active Active
- 2013-09-26 CN CN201380049853.8A patent/CN104768955B/zh active Active
- 2013-09-26 RS RS20210825A patent/RS62075B1/sr unknown
- 2013-09-26 DK DK18213678.8T patent/DK3486248T3/da active
- 2013-09-26 US US14/037,657 patent/US9012629B2/en active Active
- 2013-09-26 MY MYPI2015000663A patent/MY169250A/en unknown
- 2013-09-26 BR BR122021022582-6A patent/BR122021022582B1/pt active IP Right Grant
- 2013-09-26 RU RU2015111635A patent/RU2648992C2/ru active
- 2013-09-26 SM SM20190170T patent/SMT201900170T1/it unknown
- 2013-09-26 CA CA2884873A patent/CA2884873C/en active Active
- 2013-09-26 RU RU2018109295A patent/RU2765072C2/ru active
- 2013-09-26 JP JP2015534641A patent/JP6517693B2/ja active Active
- 2013-09-26 ES ES13774881T patent/ES2716561T3/es active Active
- 2013-09-26 ES ES18213678T patent/ES2880754T3/es active Active
- 2013-09-26 BR BR112015006505-8A patent/BR112015006505B1/pt active IP Right Grant
- 2013-09-26 HR HRP20190473TT patent/HRP20190473T1/hr unknown
- 2013-09-26 SG SG11201501918UA patent/SG11201501918UA/en unknown
- 2013-09-26 MX MX2019008652A patent/MX390615B/es unknown
- 2013-09-26 NZ NZ706019A patent/NZ706019A/en unknown
- 2013-09-26 TR TR2019/03625T patent/TR201903625T4/tr unknown
- 2013-09-26 SM SM20210390T patent/SMT202100390T1/it unknown
- 2013-09-26 CA CA3133906A patent/CA3133906C/en active Active
- 2013-09-26 WO PCT/US2013/061839 patent/WO2014052537A1/en not_active Ceased
- 2013-09-26 SI SI201331899T patent/SI3486248T1/sl unknown
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2015
- 2015-03-17 US US14/660,050 patent/US9469655B2/en active Active
- 2015-03-19 ZA ZA2015/01898A patent/ZA201501898B/en unknown
- 2015-03-23 IL IL237899A patent/IL237899A/en active IP Right Grant
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2016
- 2016-09-19 US US15/269,163 patent/US9796731B2/en active Active
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2017
- 2017-08-14 IL IL253988A patent/IL253988B/en active IP Right Grant
- 2017-09-19 US US15/708,346 patent/US10100062B2/en active Active
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2018
- 2018-02-27 JP JP2018032684A patent/JP2018109044A/ja not_active Ceased
- 2018-02-27 AU AU2018201392A patent/AU2018201392B2/en active Active
- 2018-09-12 US US16/129,268 patent/US10461449B2/en active Active
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2019
- 2019-03-13 CY CY20191100302T patent/CY1121415T1/el unknown
- 2019-09-18 US US16/574,718 patent/US10944190B2/en active Active
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2020
- 2020-04-06 JP JP2020068137A patent/JP6735000B1/ja active Active
- 2020-06-10 AU AU2020203823A patent/AU2020203823B2/en active Active
- 2020-07-10 JP JP2020118929A patent/JP2020180150A/ja active Pending
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2021
- 2021-06-29 HR HRP20211030TT patent/HRP20211030T1/hr unknown
- 2021-07-02 CY CY20211100594T patent/CY1124337T1/el unknown
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2022
- 2022-02-28 JP JP2022029253A patent/JP2022068367A/ja active Pending
- 2022-03-07 AU AU2022201557A patent/AU2022201557A1/en not_active Abandoned
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2023
- 2023-09-05 US US18/242,321 patent/US20240145953A1/en not_active Abandoned
- 2023-10-23 JP JP2023181529A patent/JP2024010055A/ja active Pending
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2024
- 2024-01-19 US US18/417,406 patent/US20240313444A1/en not_active Abandoned
- 2024-05-31 US US18/679,863 patent/US20250007192A1/en active Pending
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2025
- 2025-03-31 JP JP2025058629A patent/JP2025098242A/ja active Pending
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