JP2016500657A5 - - Google Patents
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- 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 (OSRAM) | 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 (OSRAM) |
| EP (3) | EP2900676B1 (OSRAM) |
| JP (7) | JP6517693B2 (OSRAM) |
| CN (2) | CN108586487B (OSRAM) |
| AU (4) | AU2013323572B2 (OSRAM) |
| BR (2) | BR122021022582B1 (OSRAM) |
| CA (2) | CA2884873C (OSRAM) |
| CY (2) | CY1121415T1 (OSRAM) |
| DK (2) | DK2900676T3 (OSRAM) |
| ES (2) | ES2880754T3 (OSRAM) |
| HR (2) | HRP20190473T1 (OSRAM) |
| HU (2) | HUE055443T2 (OSRAM) |
| IL (2) | IL237899A (OSRAM) |
| LT (2) | LT2900676T (OSRAM) |
| MX (2) | MX390615B (OSRAM) |
| MY (1) | MY169250A (OSRAM) |
| NZ (2) | NZ739573A (OSRAM) |
| PL (2) | PL3486248T3 (OSRAM) |
| PT (2) | PT3486248T (OSRAM) |
| RS (2) | RS58493B1 (OSRAM) |
| RU (2) | RU2765072C2 (OSRAM) |
| SG (1) | SG11201501918UA (OSRAM) |
| SI (2) | SI3486248T1 (OSRAM) |
| SM (2) | SMT201900170T1 (OSRAM) |
| TR (1) | TR201903625T4 (OSRAM) |
| WO (1) | WO2014052537A1 (OSRAM) |
| ZA (1) | ZA201501898B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2900676T3 (en) * | 2012-09-26 | 2019-04-08 | Immunogen Inc | IMPROVED PROCEDURES FOR ACYLATION OF MAYTANSINOL |
| 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 |
| CA2978182A1 (en) | 2015-03-17 | 2016-09-22 | Regeneron Pharmaceuticals, Inc. | Amino acid acylation reagents and methods of using the same |
| CN118562004A (zh) | 2016-12-16 | 2024-08-30 | 蓝鳍生物医药公司 | 抗-含cub结构域蛋白1(cdcp1)抗体、抗体药物缀合物及其使用方法 |
| US11420981B2 (en) | 2019-04-18 | 2022-08-23 | Indena S.P.A. | Diasteroselective process for the preparation of thiol- or disulfide-containing maytansinoid esters and intermediates thereof |
| JP7772363B2 (ja) | 2019-11-29 | 2025-11-18 | 日本マイクロバイオファーマ株式会社 | メイタンシノールの酵素的生産方法 |
| WO2024225377A1 (ja) | 2023-04-28 | 2024-10-31 | 中外製薬株式会社 | Ｎ－カルボキシアミノ酸無水物を用いたアミド基含有化合物の製造方法 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6034556B2 (ja) * | 1977-03-31 | 1985-08-09 | 武田薬品工業株式会社 | 抗生物質ｃ−１５００３ |
| US4151042A (en) | 1977-03-31 | 1979-04-24 | Takeda Chemical Industries, Ltd. | Method for producing maytansinol and its derivatives |
| 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 |
| AU775373B2 (en) * | 1999-10-01 | 2004-07-29 | 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 |
| AU2004240541B2 (en) | 2003-05-20 | 2009-08-20 | Immunogen, Inc. | Improved cytotoxic agents comprising new maytansinoids |
| JP2007503439A (ja) * | 2003-08-22 | 2007-02-22 | アクティブバイオティクス インコーポレイティッド | リファマイシンアナログおよびそれらの使用法 |
| CN101065151B (zh) | 2004-09-23 | 2014-12-10 | 健泰科生物技术公司 | 半胱氨酸改造的抗体和偶联物 |
| AU2005314392B2 (en) | 2004-12-09 | 2011-04-14 | 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 |
| CA2617953C (en) * | 2005-08-09 | 2013-12-17 | Millennium Pharmaceuticals, Inc. | Method of acylating maytansinol with chiral amino acids |
| WO2008057511A2 (en) * | 2006-11-06 | 2008-05-15 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | 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 |
| RS58810B1 (sr) | 2009-06-03 | 2019-07-31 | Immunogen Inc | Metodi konjugacije |
| EP2480557A2 (en) * | 2009-09-25 | 2012-08-01 | Cadila Healthcare Limited | Process for the preparation of rapamycin derivatives |
| CN103313990B (zh) * | 2010-11-17 | 2016-07-20 | 基因泰克公司 | 丙氨酰美登醇抗体偶联物 |
| DK2900676T3 (en) * | 2012-09-26 | 2019-04-08 | Immunogen Inc | IMPROVED PROCEDURES FOR ACYLATION OF MAYTANSINOL |
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2013
- 2013-09-26 DK DK13774881.0T patent/DK2900676T3/en active
- 2013-09-26 SM SM20190170T patent/SMT201900170T1/it unknown
- 2013-09-26 ES ES18213678T patent/ES2880754T3/es active Active
- 2013-09-26 BR BR122021022582-6A patent/BR122021022582B1/pt active IP Right Grant
- 2013-09-26 ES ES13774881T patent/ES2716561T3/es active Active
- 2013-09-26 SG SG11201501918UA patent/SG11201501918UA/en unknown
- 2013-09-26 HR HRP20190473TT patent/HRP20190473T1/hr unknown
- 2013-09-26 TR TR2019/03625T patent/TR201903625T4/tr unknown
- 2013-09-26 JP JP2015534641A patent/JP6517693B2/ja active Active
- 2013-09-26 HU HUE18213678A patent/HUE055443T2/hu unknown
- 2013-09-26 PT PT182136788T patent/PT3486248T/pt unknown
- 2013-09-26 AU AU2013323572A patent/AU2013323572B2/en active Active
- 2013-09-26 SM SM20210390T patent/SMT202100390T1/it unknown
- 2013-09-26 CN CN201810251853.0A patent/CN108586487B/zh active Active
- 2013-09-26 LT LTEP13774881.0T patent/LT2900676T/lt unknown
- 2013-09-26 RS RS20190314A patent/RS58493B1/sr unknown
- 2013-09-26 MX MX2019008652A patent/MX390615B/es unknown
- 2013-09-26 CN CN201380049853.8A patent/CN104768955B/zh active Active
- 2013-09-26 EP EP13774881.0A patent/EP2900676B1/en active Active
- 2013-09-26 MX MX2015003745A patent/MX366701B/es active IP Right Grant
- 2013-09-26 EP EP21166484.2A patent/EP3904358A1/en active Pending
- 2013-09-26 RS RS20210825A patent/RS62075B1/sr unknown
- 2013-09-26 SI SI201331899T patent/SI3486248T1/sl unknown
- 2013-09-26 DK DK18213678.8T patent/DK3486248T3/da active
- 2013-09-26 RU RU2018109295A patent/RU2765072C2/ru active
- 2013-09-26 US US14/037,657 patent/US9012629B2/en active Active
- 2013-09-26 PL PL18213678T patent/PL3486248T3/pl unknown
- 2013-09-26 MY MYPI2015000663A patent/MY169250A/en unknown
- 2013-09-26 CA CA2884873A patent/CA2884873C/en active Active
- 2013-09-26 SI SI201331374T patent/SI2900676T1/sl unknown
- 2013-09-26 NZ NZ73957313A patent/NZ739573A/en unknown
- 2013-09-26 RU RU2015111635A patent/RU2648992C2/ru active
- 2013-09-26 PL PL13774881T patent/PL2900676T3/pl unknown
- 2013-09-26 LT LTEP18213678.8T patent/LT3486248T/lt unknown
- 2013-09-26 NZ NZ706019A patent/NZ706019A/en unknown
- 2013-09-26 CA CA3133906A patent/CA3133906C/en active Active
- 2013-09-26 PT PT13774881T patent/PT2900676T/pt unknown
- 2013-09-26 WO PCT/US2013/061839 patent/WO2014052537A1/en not_active Ceased
- 2013-09-26 BR BR112015006505-8A patent/BR112015006505B1/pt active IP Right Grant
- 2013-09-26 EP EP18213678.8A patent/EP3486248B1/en active Active
- 2013-09-26 HU HUE13774881A patent/HUE043285T2/hu 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 AU AU2018201392A patent/AU2018201392B2/en active Active
- 2018-02-27 JP JP2018032684A patent/JP2018109044A/ja not_active Ceased
- 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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