CAS: 153773-82-1; Sodium (4R,5S,6S)-3-(((3S,5S)-5-((3-Carboxyphenyl)Carbamoyl)Pyrrolidin-3-yl)Thio)-6-((R)-1-Hydroxyethyl)-4-Methyl-7-Oxo-1-Azabicyclo[3.2.0]Hept-2-Ene-2-Carboxylate

该化合物是一种广泛频谱,可注射抗生素,属于丙烯乙酸抗生素类,主要用于治疗各种细菌感染,包括由抗菌性和抗菌性细菌以及厌食性细菌引起的感染;Ertapenem对许多乙酯表现出高度稳定,使其对抗抗药性菌株具有效力;该化合物的特点是能够有效穿透细菌细胞壁,导致细胞壁合成抑制,而细胞壁合成对于细菌生长和生存至关重要;通常通过静脉注射或肌肉内途径进行,其半衰期相对较长,允许每日一次服用;Ertapenem对某些生物没有作用,例如Pseudomonas aeruginosa和Acinetobacter物种;常见的副作用可能包括胃肠炎,头痛和潜在的过敏反应;与所有抗生素一样,建议适当的过敏性测试,以确保其对特定病原体的功效.

结构式图片

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上下游产品

(4-nitrophenyl)methyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(-carboxyphenyl)amino]carbonyl]-1-[[(4-nitrophenyl)methyoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2S-cis)-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydr°Chloride

合成工艺路线路线简述

  • 219909-83-8 + 90776-59-3 = 153773-82-1 + 866186-66-5 + 866186-68-7
    反应条件:1.1 Reagents: N-Ethyl-2-Pyrrolidone Solvents: Water; 0 °C1.2 0 °C -> -60 °C1.3 Reagents: 1,1,3,3-Tetramethylguanidine; -50 °C; 1 H,-55 - -50 °C; -55 °C -> -40 °C1.4 Reagents: Hydrogen Catalysts: Palladium Solvents: Water; 1 H,70 Psi,Rt1.5 Reagents: Sodium Hydroxide; < Ph 9,70 Psi,5 °C1.6 Reagents: Carbon Dioxide,N-Ethyl-2-Pyrrolidone; < Ph 9,70 Psi,< 15 °C1.7 Reagents: Carbon Dioxide Solvents: N-Ethyl-2-Pyrrolidone; Ph 8,70 Psi,5 °C; 30 H,5 °C -> 20 °C; 2 H,Ph 7,20 °C; 20 °C -> 5 °C
    标题:Practical Synthesis Of The New Carbapenem Antibiotic Ertapenem Sodium
    作者:Williams,J. Michael; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(19) 页码:7479-7487

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-11999757-B2
优先权日:2017-11-01
标 题:Synthesis of boronate ester derivatives and uses thereof
发明人:BOYER SERGE HENRI; HECKER SCOTT J; VERZIJL GERARDUS K M; HERMSEN PETRUS J
权利人:MELINTA SUBSIDIARY CORP
摘要:Disclosed herein are methods for the preparation of boronate derivatives in the synthesis of antimicrobial compounds and uses thereof. Disclosed herein includes method of making a compound of Formula (B) by reducing the ketone group of the keto-ester compound of Formula (A), and the reduction can be performed using a Ruthenium based catalyst system or using an alcohol dehydrogenase bioreduction system.

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-2024197774-A1
优先权日:2021-04-16
标 题:Synthesis of Antimicrobial PVP-coated Bismuth Nanoparticles
发明人:LOPEZ-RIBOT JOSE; VAZQUEZ-MUNOZ ROBERTO
权利人:UNIV TEXAS
摘要:Described herein is a facile, fast, and economical method for the synthesis of BAL-mediated PVP-BiNPs, using basic laboratory instruments and reagents readily available in most laboratories.

专利号:US-10669292-B2
优先权日:2014-05-05
标 题 :Synthesis of boronate salts and uses thereof
发明人:HECKER SCOTT; BOYER SERGE
权利人:REMPEX PHARMACEUTICALS INC
摘要:Disclosed herein are boronate intermediates in the synthesis of antimicrobial compounds and the use and preparation thereof. Some embodiments relate to crystalline boronate salt derivatives and their use in the synthesis of therapeutic compounds.

专利号:US-12221452-B2
优先权日:2017-10-04
标题:Synthesis of cantharidin
发明人:DAVIDSON MATTHEW GENE; EKLOV BRIAN MATTHEW; WUTS PETER; LOERTSCHER BRAD MELVIN; SCHOW STEVEN R
权利人:VERRICA PHARMACEUTICALS INC
摘要:The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds (i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions (e.g., infectious diseases and skin conditions).
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主要参考文献


1: Goutelle S, Valour F, Gagnieu MC, Laurent F, Chidiac C, Ferry T; Lyon Bone and Joint Infection Study Group. Population pharmacokinetics and probability of target attainment of ertapenem administered by subcutaneous or intravenous route in patients with bone and joint infection. J Antimicrob Chemother. 2017 Dec 13. doi: 10.1093/jac/dkx477. [Epub ahead of print]
3: Lass J, Tamme K, Kipper K, Starkopf J. Dosing of Ertapenem in an Extreme Obesity: A Case Report of 250 kg Patient. Case Rep Crit Care. 2017;2017:5310768. doi: 10.1155/2017/5310768. Epub 2017 Oct 8.
4: Aydın A, Barış Aykan M, Sağlam K, Veillette JJ. Seizure Induced by Ertapenem in an Elderly Patient with Dementia. Consult Pharm. 2017 Oct 1;32(10):561-562. doi: 10.4140/TCP.n.2017.561. pii: e01329-17. doi: 10.1128/AAC.01329-17. Print 2017 Nov.

合成参考文献


参考文献:10.1186/cc8877
摘要:Augustin P, Kermarrec N, Muller-Serieys C, Lasocki S, Chosidow D, Marmuse JP, Valin N, Desmonts JM, Montravers P. Risk factors for multidrug resistant bacteria and optimization of empirical antibiotic therapy in postoperative peritonitis. Crit Care. 2010;14(1):R20.
参考文献:10.1111/j.1469-0691.2011.03515.x
摘要:Findlay J, Hamouda A, Dancer SJ, Amyes SG. Rapid acquisition of decreased carbapenem susceptibility in a strain of Klebsiella pneumoniae arising during meropenem therapy. Clin Microbiol Infect. 2012 Feb;18(2):140–6. doi: 10.1111/j.1469-0691.2011.03515.x.
参考文献:10.1128/aac.01513-10
摘要:Guillon H, Tande D, Mammeri H. Emergence of ertapenem resistance in an Escherichia coli clinical isolate producing extended-spectrum beta-lactamase AmpC. Antimicrob Agents Chemother. 2011 Sep;55(9):4443–6.
摘要:Chaudhuri BN, Rodrigues C, Balaji V, Iyer R, Sekar U, Wattal C, Chitnis DS, Dhole TN, Joshi S. Incidence of ESBL producers amongst Gram-negative bacilli isolated from intra-abdominal infections across India (based on SMART study, 2007 data). J Assoc Physicians India. 2011 May;59():287–92.
参考文献:10.4137/aci.s5953
摘要:Narola B, Singh AS, Mitra M, Santhakumar PR, Chandrashekhar TG. A validated reverse phase HPLC method for the determination of disodium EDTA in meropenem drug substance with UV-detection using precolumn derivatization technique. Anal Chem Insights. 2011;6():7–14.
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