CAS: 72496-41-4; (8S,10S)-10-(((2R,4S,5S,6S)-4-Amino-6-Methyl-5-(((R)-Tetrahydro-2H-Pyran-2-yl)Oxy)Tetrahydro-2H-Pyran-2-yl)Oxy)-6,8,11-Trihydroxy-8-(2-Hydroxyacetyl)-1-Methoxy-7,8,9,10-Tetrahydrotetracene-5,12-Dione

该化合物是炭疽抗生素,主要用作癌症治疗中的抗乳粉剂,在结构上与毒理素有关,并展示类似的行动机制,主要是通过切入DNA,从而抑制DNA和RNA合成,导致细胞死亡.Pirarubicin对各种癌症,包括乳腺癌和白血病特别有效.其药理学特征包括中度至高水平的细胞毒性,而且经常是静脉注射.该药物具有潜在的副作用,可能包括心毒性,乳房压抑和胃肠紊乱.由于其化学结构,Pirarubicin还能够产生活性氧物种,导致其抗癌效应.该化合物通常与其他乳房化剂结合使用,以提高治疗功效,同时管理抗药性.与所有乳房化剂一样,对病人的仔细监测对于减轻不利影响和优化治疗结果至关重要.

结构式图片

欧盟法规

C&L通报

合成工艺路线路线简述

    (7S,9S)-7-[(2R,4S,5S,6S)-4-Amino-6-Methyl-5-(Oxan-2-Yloxy)Oxan-2-Yl]Oxy-9-(2-Bromoacetyl)-6,9,11-Trihydroxy-4-Methoxy-8,10-Dihydro-7H-Tetracene-5,12-Dione 反应生成 Pirarubicin
    参考文献:Umehdzava,Xamao;Takehuti,Tomio;Naganava,Xirosi;Tatsuda,Kuniaki
    标题:Umehdzava,Xamao;Takehuti,Tomio;Naganava,Xirosi;Tatsuda,Kuniaki

    专利信息


    专利号:US-9353057-B2
    优先权日:2003-12-30
    标 题:Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
    发明人:GALLOP MARK A; DAI XUEDONG; SCHEUERMAN RANDALL A; RAILLARD STEPHEN P; MANTHATI SURESH K; YAO FENMEI; PHAN THU; LUDWIKOW MARIA; PENG GE; BHAT SEEMA
    权利人:XENOPORT INC
    摘要:Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine-containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.

    专利号:US-12383499-B2
    优先权日:2018-01-01
    标题:Scale up synthesis of silicasome nanocarriers
    发明人:NEL ANDRE E; MENG HUAN; LIU XIANGSHENG
    权利人:UNIV CALIFORNIA
    摘要:In order to facilitate the approval and commercialization of silicasome drug delivery systems (e.g. irinotecan silicasomes) it is necessary to scale up synthesis of the drug-loaded silicasomes. In this regard, it was discovered that the synthesis protocols used for laboratory synthesis of drug-loaded silicasomes (e.g., 500 mg/batch) do not scale to large scale silicasome production, because the resulting products were too heterogeneous for use as pharmaceuticals. Accordingly, new methods are provided herein that effectively afford the large-scale production of mesoporous silica nanoparticles (MSNPs) and lipid bilayer coated MSNPs (silicasomes).

    专利号:US-10925977-B2
    优先权日:2006-10-05
    标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
    发明人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
    权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
    摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

    专利号:US-10973847-B2
    优先权日:2017-06-30
    标题 :Core-to-surface polymerization for the synthesis of star polymers and uses thereof
    发明人:JOHNSON JEREMIAH A; GOLDER MATTHEW R
    权利人:MASSACHUSETTS INST TECHNOLOGY
    摘要:Disclosed are methods, compositions, reagents, systems, and kits to prepare star polymers, as well as compositions and uses thereof. Various embodiments show that synthesis of these polymers contain low metal concentration to provide polymers for diverse biomedical applications including in vivo applications.

    专利号:US-12391691-B2
    优先权日:2018-11-16
    标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
    发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
    权利人:AMGEN INC
    摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

    专利号:US-2025206736-A1
    优先权日:2019-11-14
    标题 :Synthesis of kras g12c inhibitor compound
    发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
    权利人:AMGEN INC
    摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.
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    主要参考文献


    1: Miller AA, Salewski E. Prospects for pirarubicin. Med Pediatr Oncol. 1994;22(4):261-8. doi: 10.1002/mpo.2950220410.
    1224:123754. doi: 10.1016/j.jchromb.2023.123754. Epub 2023 May 15. 15(9):2819-27. Japanese. 51(10):e13920. doi: 10.1111/1440-1681.13920. 142(Pt A):113068. doi: 10.1016/j.intimp.2024.113068. Epub 2024 Sep 5. 63(3):311-318. doi: 10.1177/0284185121994298. Epub 2021 Feb 20. 13(15):3698. doi: 10.3390/cancers13153698.
    8: Zhang Y, Ma XY, Zhang T, Qin M, Sun B, Li Q, Hu DW, Ren LQ. Protective Effects of Apocynum venetum Against Pirarubicin-Induced Cardiotoxicity. Am J Chin Med. 2019;47(5):1075-1097. doi: 10.1142/S0192415X19500551. Epub 2019 Jul 17. 10(5):871. doi: 10.3390/children10050871.

    合成参考文献


    摘要:S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
    摘要:Biochemical Pharmacology., 38(167), 1989 []
    摘要:Journal of Antibiotics., 32(1082), 1979 []
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