Proprietary Synthesis of the C27-C35 Fragment of Eribulin and Its Elaboration toward the C14-C35 Subunit

被引：0

作者：

Kim, U. Bin ^{[1
]}

Samala, Srinivas ^{[1
]}

Jung, Jaehun ^{[1
]}

Song, Juyoung ^{[1
]}

Lee, Kee-Young ^{[1
]}

Oh, Chang-Young ^{[1
]}

Shin, Hyunik ^{[1
]}

机构：

[1] YS Life Sci Co Ltd, R&D Ctr, Suwon 16675, Gyeonggi Do, South Korea

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2024年 / 28卷 / 07期

关键词：

Eribulin; patent life cyclemanagement; sulfide; NHK coupling; oxetanes; proprietary processdevelopment; HALAVEN(R); SYNTHESIS;

D O I：

10.1021/acs.oprd.4c00150

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Successful kilogram-scale preparation of the C27-C35 sulfide fragment of Eribulin was presented, which was elaborated with the C14-C26 fragment to produce a proprietary C14-C35 sulfide intermediate. The sulfide group was then oxidized to yield the known C14-C35 sulfone intermediate of Eribulin.

引用

页码：2832 / 2843

页数：12

共 27 条

[1] Natural products in drug discovery: advances and opportunities [J].

Atanasov, Atanas G. ;

Zotchev, Sergey B. ;

Dirsch, Verena M. ;

Supuran, Claudiu T. .

NATURE REVIEWS DRUG DISCOVERY, 2021, 20 (03) :200-216

[2]

Austad B., 2018, U.S. Patent, Patent No. [46965E1, 46965]

[3]

Austad B., 2013, U.S. Patent, Patent No. [8445701B2, 8445701]

[4] Process Development of Halaven®: Synthesis of the C14-C35 Fragment via Iterative Nozaki-Hiyama-Kishi Reaction-Williamson Ether Cyclization [J].

Austad, Brian C. ;

Benayoud, Farid ;

Calkins, Trevor L. ;

Campagna, Silvio ;

Chase, Charles E. ;

Choi, Hyeong-Wook ;

Christ, William ;

Costanzo, Robert ;

Cutter, James ;

Endo, Atsushi ;

Fang, Francis G. ;

Hu, Yongbo ;

Lewis, Bryan M. ;

Lewis, Michael D. ;

McKenna, Shawn ;

Noland, Thomas A. ;

Orr, John D. ;

Pesant, Marc ;

Schnaderbeck, Matthew J. ;

Wilkie, Gordon D. ;

Abe, Taichi ;

Asai, Naoki ;

Asai, Yumi ;

Kayano, Akio ;

Kimoto, Yuichi ;

Komatsu, Yuki ;

Kubota, Manabu ;

Kuroda, Hirofumi ;

Mizuno, Masanori ;

Nakamura, Taiju ;

Omae, Takao ;

Ozeki, Naoki ;

Suzuki, Taeko ;

Takigawa, Teiji ;

Watanabe, Tomohiro ;

Yoshizawab, Kazuhiro .

SYNLETT, 2013, 24 (03) :327-332

[5] Commercial Manufacture of Halaven®: Chemoselective Transformations En Route to Structurally Complex Macrocyclic Ketones [J].

Austad, Brian C. ;

Calkins, Trevor L. ;

Chase, Charles E. ;

Fang, Francis G. ;

Horstmann, Thomas E. ;

Hu, Yongbo ;

Lewis, Bryan M. ;

Niu, Xiang ;

Noland, Thomas A. ;

Orr, John D. ;

Schnaderbeck, Matthew J. ;

Zhang, Huiming ;

Asakawa, Naoki ;

Asai, Naoki ;

Chiba, Hiroyuki ;

Hasebe, Takashi ;

Hoshino, Yorihisa ;

Ishizuka, Hiroyuki ;

Kajima, Takashi ;

Kayano, Akio ;

Komatsu, Yuki ;

Kubota, Manabu ;

Kuroda, Hirofumi ;

Miyazawa, Mamoru ;

Tagami, Katsuya ;

Watanabeb, Tomohiro .

SYNLETT, 2013, 24 (03) :333-337

[6]

Benayoud F., 2016, U.S. Patent, Patent No. [9303050B2, 9303050]

[7]

Benayoud F., 2020, U.S. Patent, Patent No. [RE47797E1, 47797]

[8]

Benayoud F., 2013, U.S. Patent, Patent No. [8618313B2, 8618313]

[9] Systematic review of Real-World effectiveness of eribulin for locally advanced or metastatic breast cancer [J].

Chabot, Isabelle ;

Zhao, Qi ;

Su, Yun .

CURRENT MEDICAL RESEARCH AND OPINION, 2020, 36 (12) :2025-2036

[10]

Chase C. E., 2014, U.S. Patent, Patent No. [8884031B2, 8884031]

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