CAS: 87726-17-8; (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(((S)-1-(1-Iminoethyl)Pyrrolidin-3-yl)Thio)-7-Oxo-1-Azabicyclo[3.2.0]Hept-2-Ene-2-Carboxylic Acid

该化合物是一种属于碳膜菌类的泛光线乙酯抗生素,众所周知,这种抗生素对多种抗药性和抗菌性细菌具有效力,其特点是能够抑制细菌细胞壁合成,导致细胞分解和死亡; Panipenem经常与另一种物剂,如Cilastatin结合使用,以防止其通过肾上分泌脱氢甲酯I降解,从而提高其治疗效力;该化合物通常通过静脉注射进行,并显示其严重感染,包括多抗药性生物造成的感染;它对于各种抗生素的抗体,其稳定性使其成为治疗传染病的宝贵选择;然而,它与其他抗生素一样,可能与副作用有关,包括胃肠扰动和潜在的过敏反应.由于其广泛感染活动,Panipenem经常保留在抗感染较普遍的医院环境中使用.

结构式图片

欧盟法规

C&L通报

上下游产品

ethyl acetimidate hydr°Chloride 4-nitrobenzyl 2-diazo-3-oxo-butanoate 3-(S)-acetylthio-1-p-nitrobenzyloxycarbonylpyrrolidine

合成工艺路线路线简述

    Azepinone,乙基乙酰亚胺盐酸盐,2-重氮乙酰乙酸对硝基苄酯,3-(S)-Acetylthio-1-P-Nitrobenzyloxycarbonylpyrrolidine置于三乙胺,六甲基二硅氮烷,Sodium Iodide,甲烷磺酸,Zinc Dibromide体系中,用 甲苯,甲醇 作为反应溶剂,以89.4%的收率获得产物帕尼培南
    参考文献:一种抗生素药物帕尼培南的制备工艺
    标题:一种抗生素药物帕尼培南的制备工艺
    摘要:本发明公开了一种抗生素药物帕尼培南的制备工艺,采用了独特的合成方法来进行制备.本发明解决了现有抗生素药物帕尼培南的制备中原材料较贵,生产过程周期长,收率低和纯度低等问题.本发明为帕尼培南的合成提供了一种高效,高收率,纯度高,周期短且生产成本低的制备工艺.

    海关参考信息

    专利信息


    专利号:US-2023286915-A1
    优先权日:2020-10-07
    标 题 :Synthesis of pyrrole acid derivatives
    发明人:WILKINSON ANDREW; COOPER LAN; ORR DAVID; FINLAYSON JONATHAN; BUNT ADAM; KIRKHAM JAMES; LYTH DAVID; BLADES KEVIN
    权利人:INFEX THERAPEUTICS LTD
    摘要:This invention relates to the synthesis of compounds that can be used to treat bacterial infections in combination with other antibacterial agents, and more specifically in combination with a class of antibacterial agents known as carbapenems. The compounds resulting from the novel methods of the present invention are enzyme inhibitors and more particularly are metallo-β-lactamase inhibitors.

    专利号:US-8557979-B2
    优先权日:2004-06-10
    标题 :Carbapenem antibacterials with gram-negative activity and processes for their preparation
    发明人:CHOI WOO-BAEG; KOWALIK EWA
    权利人:CHOI WOO-BAEG; KOWALIK EWA; FOB SYNTHESIS INC
    摘要:The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of β-methyl carbapenems which are useful as antibacterial agents.

    专利号:WO-2014097257-A1
    优先权日:2012-12-21
    标 题:A method of preparation of (1'r,3r,4r)-4-acetoxy-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone, a precursor for carbapenem antibiotics synthesis
    发明人:GRZESZCZYK BARBARA; STECKO SEBASTIAN; FURMAN BARTÅ?OMIEJ; CHMIELEWSKI MAREK
    权利人:INST CHEMII ORGANICZNEJ PAN
    摘要:The subject of the present invention is a method of preparation of (1'R,3R,4R)-4-acetoxy-3-(1'- (tert-butyl-dimethylsilyloxy)ethyl)-2-azetidinone defined by the formula (1) which is a basic chiral building block in the synthesis of carbapenem antibiotics.

    专利号:US-9663771-B2
    优先权日:2013-01-18
    标题 :Engineered biocatalysts useful for carbapenem synthesis
    发明人:SUKUMARAN JOLY; SMITH DEREK; YANG HONG; YEO WAN LIN; MOORE JEFFREY C
    权利人:CODEXIS INC
    摘要:The present disclosure provides engineered pNB esterase polypeptides useful for the synthesis of the carbapenem antibiotic, imipenem. The disclosure also provides polynucleotides encoding the engineered pNB esterases, host cells capable of expressing the engineered pNB esterases, and methods of using the engineered pNB esterases in the production of imipenem.

    专利号:US-6566525-B1
    优先权日:1998-09-17
    标 题:Preparation of N-substituted-hydroxycycloalkylamine derivatives
    发明人:KIM SEONG JIN; KIM KEON IL; YANG KYOUNG YOUL
    权利人:SAMSUNG FINE CHEMICALS CO LTD
    摘要:A process for the preparation of N-substituted-hydroxycycloalkylamine derivatives, that are useful intermediates for the synthesis of various organic chemicals including pharmaceutical and agrochemical compounds, represented by formula (1), by reacting a 1,2-dihydroxalkyl alcohol, represented by the following formula (2), with a thionyl halide to produce an intermediate 1,2-cyclosulfinylalkyl halide represented by the following formula (3); and then cyclizing that intermediate with an amine compounds represented by the following formula (4).In the above structural formuli, * represents an asymmetric carbon atom; R1 is hydrogen or an amino-protecting group; m is an integer of 1-3; and X is halogen. The reactant compounds as well as the compounds made according to this invention have the following substitution pattern:n=1, R2=OH, R3=H and m=1; n=1, R2=H, R3=CH2OH and m=2;n=2, R2=OH, R3=H; and m=2; and n=2, R2=H, R3=CH2OH and m=3.

    专利号:US-12221646-B2
    优先权日:2013-07-04
    标 题:Method for the rapid determination of susceptibility or resistance of bacteria to antibiotics
    发明人:FERNÃ?NDEZ GARCÃ?A JOSÉ LUIS; GOSÃ?LVEZ BERENGUER JAIME; SANTISO BRANDARIZ REBECA; TAMAYO NOVAS MARIA; BOU ARÉVALO GERMÃ?N
    权利人:ABM TECH LLC
    摘要:A method of rapidly evaluating the susceptibility of a strain of bacteria to a cell wall synthesis inhibiting antibiotic based on an assessment of cell enlargement in response to doses of the cell wall synthesis inhibiting antibiotic which are correlated to breakpoints of bacterial susceptibility.
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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Kato A, Ueyama J, Abe F, Hotta K, Tsukiyama I, Oshima T, Kondo F, Saito H, Hasegawa T. Panipenem does not alter the pharmacokinetics of the active metabolite of irinotecan SN-38 and inactive metabolite SN-38 glucuronide (SN-38G) in rats. Anticancer Res. 2011 Sep;31(9):2915-22. Prospective randomized study of cefepime, panipenem, or meropenem monotherapy for patients with hematological disorders and febrile neutropenia. J Infect Chemother. 2013 Feb;19(1):103-11. doi: 10.1007/s10156-012-0466-8. Epub 2012 Sep 5. doi: 10.1007/s10156-012-0525-1. Epub 2012 Dec 1. doi: 10.1016/j.ijantimicag.2012.12.014. Epub 2013 Feb 12. Chinese. Review.
    8: Ohashi N, Uematsu T, Nagashima S, Kanamaru M, Tajima N, Togawa A, Hishida A. Pharmacokinetics of panipenem/betamipron in patients with end-stage renal disease. J Infect Chemother. 2005 Feb;11(1):24-31. doi: 10.1093/jjco/hym151. Epub 2008 Jan 17.
    11: Tajima N, Ishizuka H, Naganuma H. Population pharmacokinetic analysis of panipenem/betamipron in patients with various degrees of renal function. Chemotherapy. 2006;52(5):245-53. Epub 2006 Jul 25. doi: 10.3760/cma.j.issn.00376-2491-2012.07.006. Chinese.

    合成参考文献


    摘要:Chemotherapy, 39(Suppl
    摘要:Igari J, Shibano T, Satou S, Inoue M, Kobayashi I, Takahashi A, Yomoda S, Nishino T, Oguri T, Watanabe N, Uehara N, Kumasaka K, Yoshida H, Imafuku Y, Kobayasi Y, Okada J, Tokuda K, Hirata Y, Nakasaki N, Hongo T, Kawaguchi R, Ohtaki Y, Sasaki T, Matsumoto N, Saeki H. [Survey of the sensitivities of clinical isolates to antibacterial agents (annual report)]. Jpn J Antibiot. 1999 Apr;52(4):279–91.
    摘要:Hiraishi T, Miyata A, Takata T, Araake M, Ogawa H, Gotoh N, Nishino T. [Bactericidal activity of biapenem against various efflux system mutants of Pseudomonas aeruginosa]. Jpn J Antibiot. 2002 Feb;55(1):67–76.
    参考文献:10.1007/s10384-007-0491-9
    摘要:Tsuchida H, Takagi M, Miki A, Usui T, Hasegawa S, Abe H. A case of osteopetrosis with acute optic neuropathy. Japanese Journal of Ophthalmology. 2008 Feb;52(1):72–4. doi: 10.1007/s10384-007-0491-9.
    参考文献:10.11150/kansenshogakuzasshi1970.73.1048
    摘要:Hanaki H, Hiramatsu K. [Combination effect of teicoplanin and various antibiotics against hetero-VRSA and VRSA]. Kansenshogaku Zasshi. 1999 Oct;73(10):1048–53. doi: 10.11150/kansenshogakuzasshi1970.73.1048.
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