CAS: 125995-03-1; 5-(4-Fluorophenyl)-1-(2-((2R,4R)-4-Hydroxy-6-Oxotetrahydro-2H-Pyran-2-yl)Ethyl)-2-Isopropyl-N,4-Diphenyl-1H-Pyrrole-3-Carboxamide

该化合物是一种化学化合物,作为阿托瓦斯特纳(Atorvastatin)的前体,是用来降低胆固醇水平的一种广泛使用的静态药物,这种内酯形式的特征是循环酯结构,它是由碳酸和酒精反应形成的.Atorvastatin lactone表现出脂质的特性,使其能有效渗透细胞膜.它一般是白到白的固态,在有机溶剂中溶解,但水溶性有限.该化合物以其药理活动而著名,因为它能够抑制HMG-CoA再生酶,这是胆固醇生物合成途径中至关重要的酶.这种抑制导致肝脏中胆固醇的产量下降,最终降低血清胆固醇水平.此外,阿托瓦斯特酮在生物系统中进行水解,以产卵巢为生,但水溶性能作用有限,因为它能抑制HMG-CA再生,这种反应是化学的活跃形态.

结构式图片

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上下游产品

CAS号842163-03-5 (2R,4R)-1-[2-(4... | CAS号134523-00-5 阿伐他汀 | CAS号581772-29-4 Atorvastatin ac... | CAS号125971-86-0 tert-butyl 2-((... | CAS号125971-96-2 4-氟-α-[2-甲基-1-氧... | CAS号340266-37-7 [R-(R*,R*)]-2-(... | CAS号125971-95-1 (4R,6R)-2-[6-[2... | CAS号67-56-1 甲醇 | CAS号110862-44-7 α-[[2-(1,3-diox... | CAS号134523-01-6 阿伐他汀钠

合成工艺路线路线简述

    Lipitor置于盐酸体系中,用 水 用作溶剂,化学反应 2.0H,以55%的收率获得阿托伐他汀内酯
    参考文献:用强酸处理后形成的两种新的阿托伐他汀钙降解产物的表征
    标题:用强酸处理后形成的两种新的阿托伐他汀钙降解产物的表征
    摘要:阿托伐他汀钙(立普妥®,Sortis ®)是一种建立非常好的胆固醇合成酶(cse)抑制剂,通常用于治疗高胆固醇血症.已知该药物对酸处理敏感,但有关降解产物的结构的数据很少.在这里,我们报告鉴定两个仅在剧烈酸性条件下形成的阿托伐他汀的新型降解产物.同时用浓密治疗.用浓硫酸处理会导致羧酰苯胺残留物的损失(伴随侧链预期的内酯化/脱水过程).在盐酸水溶液中,内酯部分与吡咯在c-C键下形成复杂的桥连分子,异丙基迁移,羧酰苯胺残基丢失.通过NMR光谱对新型降解产物进行了表征,
    Doi:10.3762/bjoc.15.206

    海关参考信息

    专利信息


    专利号:US-2007015260-A1
    优先权日:2002-03-14
    标 题:Synthesis of synthons for the manufacture of bioactive compounds
    发明人:WONG CHI-HUEY; LIU JUNJIE; DESANTIS GRACE; BURK MARK
    权利人:SCRIPPS RESEARCH INST
    摘要:The present invention is based on the discovery that 2-deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4) and variants thereof can be used to catalyze sequential asymmetric aldol reactions between a wide variety of donor and acceptor aldehydes. The reaction products typically contain at least two new stereogenic centers and can be produced in enantiomerically pure form. As such, DERA catalyzed asymmetric aldol chemistry can be exploited to produce synthons for the synthesis of a variety of bioactive molecules.

    专利号:US-10647655-B2
    优先权日:2016-09-02
    标题:Method for the synthesis of permethrin
    发明人:PULLAGURLA MANIK REDDY; NANDA KUMAR MECHERIL VALSAN; VELIGETLA MADHUSUDHANA RAO; RANGISETTY JAGADEESH BABU
    权利人:BIOPHORE INDIA PHARMACEUTICALS PVT LTD
    摘要:An improved method for the synthesis of substantially pure Permethrin having purity greater than 99.5% by Gas Chromatography provided. The embodiments also relates to a purification process of Permethrin by recrystallization from methanol-water mixture.

    专利号:US-7399773-B2
    优先权日:2001-01-09
    标 题 :Process for the synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid and phenylamide
    发明人:NELSON JADE DOUGLAS; PAMMENT MICHAEL GERARD
    权利人:WARNER LAMBERT CO
    摘要:An improved process for the preparation of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide by a novel synthesis is described where methyl cyanoacetate is converted in eight operations or fewer to the desired product, as well as other valuable intermediates used in the process.

    专利号:US-7232915-B2
    优先权日:1997-12-19
    标题:Process for the synthesis of 1,3-diols
    发明人:BOSCH ROBERT LEE; MCCABE RICHARD JOSEPH; NANNINGA THOMAS NORMAN; STAHL ROBERT JOSEPH
    权利人:WARNER LAMBERT CO
    摘要:An improved process for the preparation of cis-1,3-diols is described where a beta hydroxy ketone is treated with a trialkylborane or dialkylalkoxyborane or a mixture of a trialkylborane and a dialkylalkoxyborane followed by recovery and reuse of the alkylborane species to convert additional beta hydroxy ketone to the cis-1,3-diol.

    专利号:US-5155251-A
    优先权日:1991-10-11
    标题:Process for the synthesis of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate
    发明人:BUTLER DONALD E; LE TUNG V; MILLAR ALAN; NANNINGA THOMAS N
    权利人:WARNER LAMBERT CO
    摘要:An improved process for the preparation of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate is described where a halo hydroxyester or other activated dihydroxyester is converted in two steps to the desired product.

    专利号:US-5248793-A
    优先权日:1990-10-17
    标 题:Process for the synthesis of (4R-cis)-1,1-dimethylethyl 6-iodomethyl or 6-(phenyl-substituted)sulfonyloxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
    发明人:MILLAR ALAN; BUTLER DONALD E
    权利人:WARNER LAMBERT CO
    摘要:An improved process for the preparation of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate is described where a hydroxy ester derivative is converted in two steps to the desired product, as well as valuable intermediates used in the process.
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    主要参考文献


    1: Leung YH, Turgeon J, Michaud V. Study of Statin- and Loratadine-Induced Muscle Pain Mechanisms Using Human Skeletal Muscle Cells. Pharmaceutics. 2017 Oct 10;9(4). pii: E42. doi: 10.3390/pharmaceutics9040042. doi: 10.1016/j.arteri.2016.06.006. Epub 2016 Sep 9. Spanish. doi: 10.1016/j.jpsychires.2016.07.004. Epub 2016 Jul 7. doi: 10.1007/s00228-016-2043-z. Epub 2016 Mar 29. doi: 10.1186/s12944-015-0134-y.
    6: Schirris TJ, Ritschel T, Bilos A, Smeitink JA, Russel FG. Statin Lactonization by Uridine 5'-Diphospho-glucuronosyltransferases (UGTs). Mol Pharm. 2015 Nov 2;12(11):4048-55. doi: 10.1021/acs.molpharmaceut.5b00474. Epub 2015 Oct 6. doi: 10.1016/j.bjid.2015.06.001. Epub 2015 Jun 26. doi: 10.1016/j.ejps.2015.06.019. Epub 2015 Jun 24. pii: bcr2015209961. doi: 10.1136/bcr-2015-209961.
    10: Yu Y, Teerenstra S, Neef C, Burger D, Maliepaard M. Investigation into the interchangeability of generic formulations using immunosuppressants and a broad selection of medicines. Eur J Clin Pharmacol. 2015 Aug;71(8):979-90. doi: 10.1007/s00228-015-1878-z. Epub 2015 Jun 12.

    合成参考文献


    摘要:S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
    摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2006).
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