JP7289799B2 - オリゴペプチドリンカー中間体及びその製造方法 - Google Patents
オリゴペプチドリンカー中間体及びその製造方法 Download PDFInfo
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Description
(1)Fmoc保護基の使用
1)カルボニル化試薬及び2-(トリメチルシリル)エタノールを、順にアミノ酸AA1、アミノ酸AA2と、又は順にアミノ酸AA1、アミノ酸AA2、アミノ酸AA3と、又は順にアミノ酸AA1、アミノ酸AA2、アミノ酸AA3、アミノ酸AA4と縮合反応させて2-(トリメチルシリル)エトキシカルボニル-オリゴペプチド縮合物を得、
2)反応で得られた2-(トリメチルシリル)エトキシカルボニル-オリゴペプチド縮合物とp-アミノベンジルアルコールとを反応させて2-(トリメチルシリル)エトキシカルボニル-オリゴペプチド-p-アミノベンジルアルコール縮合物を得、
ここで、前記カルボニル化試薬は、カルボニル基を含む任意の化合物である。
1)カルボニル化試薬を2-(トリメチルシリル)エタノール及びアミノ酸AA1と縮合反応させて2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物を得るステップと、
2)2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物とアミノ酸AA2を縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物を得るステップと、
3)2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物とp-アミノベンジルアルコールとを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド-p-アミノベンジルアルコール縮合物を得るステップと、を含む。
1)カルボニル化試薬を2-(トリメチルシリル)エタノール及びアミノ酸AA1と縮合反応させて2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物を得るステップと、
2)2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物とアミノ酸AA2とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物を得るステップと、
3)2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物とアミノ酸AA3とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物を得るステップと、
4)2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物とp-アミノベンジルアルコールとを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-トリペプチド-p-アミノベンジルアルコール縮合物を得るステップと、を含む。
1)カルボニル化試薬を2-(トリメチルシリル)エタノール及びアミノ酸AA1と縮合反応させて2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物を得るステップと、
2)2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物とアミノ酸AA2とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物を得るステップと、
3)2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物とアミノ酸AA3とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物を得るステップと、
4)2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物とアミノ酸AA4とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-テトラペプチド縮合物を得るステップと、
5)2-(トリメチルシリル)エトキシカルボニル-テトラペプチド縮合物とp-アミノベンジルアルコールとを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-テトラペプチド-p-アミノベンジルアルコール縮合物を得るステップと、を含む。
2)2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物とアミノ酸AA2とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物を得るステップと、
3)2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物とアミノ酸AA3とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物を得るステップと、
4)2-(トリメチルシリル)エトキシカルボニル-トリペプチド縮合物とアミノ酸AA4とを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-テトラペプチド縮合物を得るステップと、を含む。
特定の実施例において、前記オリゴペプチドリンカーは、
Claims (3)
- 構造式(1)で表されるオリゴペプチドリンカー中間体の製造方法であって、前記オリゴペプチドリンカー中間体は以下の反応経路によって得られ、
前記製造方法は、
1)構造式
2)2-(トリメチルシリル)エトキシカルボニル-アミノ酸縮合物とアミノ酸AA2 シトルリンとを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物を得るステップと、
3)2-(トリメチルシリル)エトキシカルボニル-ジペプチド縮合物とp-アミノベンジルアルコールとを縮合反応させて2-(トリメチルシリル)エトキシカルボニル-ジペプチド-p-アミノベンジルアルコール縮合物を得るステップとを含む製造方法。 - 前記縮合反応で用いられる溶媒は、テトラヒドロフラン、ジオキサン、アセトニトリル、DMF、DMSO、水、メタノール、ジクロロメタン、クロロホルム、四塩化炭素及びエタノールから選ばれる1種又は複数種である、ことを特徴とする請求項1に記載の製造方法。
- 請求項1又は2に記載の製造方法の、抗体薬物複合体の調製における応用。
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US20120141414A1 (en) | 2009-05-22 | 2012-06-07 | Sequoia Pharmaceuticals, Inc. | Bimacrocylic HCV NS3 Protease Inhibitors |
WO2019108797A1 (en) | 2017-11-30 | 2019-06-06 | Seattle Genetics, Inc. | Process for the preparation of drug linker compounds |
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US20120141414A1 (en) | 2009-05-22 | 2012-06-07 | Sequoia Pharmaceuticals, Inc. | Bimacrocylic HCV NS3 Protease Inhibitors |
WO2019108797A1 (en) | 2017-11-30 | 2019-06-06 | Seattle Genetics, Inc. | Process for the preparation of drug linker compounds |
Non-Patent Citations (5)
Title |
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Beilstein Journal of Organic Chemistry,2016年,Vol.12,pp.564-570 |
Frontiers in Chemistry,2015年,Vol.3, Article 19,pp.1-7 |
Journal of Organic Chemistry,2000年,Vol.65,pp.5996-6000 |
Journal of the Chemical Society, Perkin Transactions 1,2001年,pp.2109-2135 |
Tetrahedron,2006年,Vol.62,pp.8907-8918 |
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US20230128167A1 (en) | 2023-04-27 |
CA3065644C (en) | 2021-11-02 |
WO2021077317A1 (zh) | 2021-04-29 |
EP3838913A4 (en) | 2021-11-03 |
US20210230218A1 (en) | 2021-07-29 |
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