CAS: 65085-01-0; (6R,7R)-7-((Z)-2-(2-Aminothiazol-4-yl)-2-(Methoxyimino)Acetamido)-3-(((1-Methyl-1H-Tetrazol-5-yl)Thio)Methyl)-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid

该化合物是第三代甲状腺素抗生素,其抗药活动范围广泛,可以防治克氏阴性细菌和克氏阳性细菌,对β乳性动物具有高度稳定性,提高了抗抗抗药菌株的功效,该化合物对肠杆菌切除性肝炎,包括大肠杆菌和克莱比氏肺炎,以及流感嗜血杆菌和淋病,特别有效,其药理学特征包括快速吸收和良好的组织渗透,使之适合治疗呼吸道,尿道和软组织感染,由于口腔生物利用率低,对乙型脑膜炎进行亲切性控制,其临床效用因其药效,半衰期延长和有利的安全特征而得到强调,与早期的甲状腺素相比,其不利影响最小.

结构式图片

上下游产品

CAS号24209-38-9 头孢甲肟中间体

合成工艺路线路线简述

    (6R,7R)-7-[[(2Z)-2-(2-Formamido-1,3-Thiazol-4-yl)-2-Methoxyiminoacetyl]Amino]-3-[(1-Methyltetrazol-5-yl)Sulfanylmethyl]-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]oct-2-Ene-2-Carboxylic Acid 反应生成 头孢甲肟
    参考文献:Yamada,Hirotada;Ueda,Shinji;Mutoh,Masayuki;Nagata,Hideo;Nouda,Hirosh+,J. Antibiotics.,43,(1990) N,C. 578-583
    标题:Yamada,Hirotada;Ueda,Shinji;Mutoh,Masayuki;Nagata,Hideo;Nouda,Hirosh+,J. Antibiotics.,43,(1990) N,C. 578-583

    海关参考信息

    专利信息


    专利号:US-8017776-B2
    优先权日:2003-07-15
    标题 :Methods for synthesis of acyloxyalkyl compounds
    发明人:BHAT LAXMINARAYAN; GALLOP MARK A
    权利人:XENOPORT INC
    摘要:Disclosed herein are methods for synthesizing 1-(acyloxy)-alkyl prodrug derivatives of drugs through oxidation of 1-acyl-alkyl derivatives of drugs under anhydrous reaction conditions. The methods typically proceed stereospecifically, in high yield, do not require the use of activated intermediates and/or toxic compounds and are readily amenable to scale-up.

    专利号:US-8143437-B2
    优先权日:2002-02-19
    标题:Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
    发明人:GALLOP MARK A; XIANG JIA-NING; YAO FENMEI; BHAT LAXMINARAYAN; ZHOU CINDY X
    权利人:GALLOP MARK A; XIANG JIA-NING; YAO FENMEI; BHAT LAXMINARAYAN; ZHOU CINDY X; XENOPORT INC
    摘要:The present invention provides a method for synthesizing 1-(acyloxy)-alkyl derivatives from 1-acyl-alkyl derivatives, which typically proceeds stereospecifically, in high yield, does not require the use of activated intermediates and/or toxic compounds and is readily amendable to scale-up. The current invention also provides 1-acyl-alkyl derivatives of known drug components and methods for synthesizing these 1-acyl-alkyl derivatives.

    专利号:US-4927964-A
    优先权日:1988-01-18
    标 题:Method for production of 2-oxyimino-3-oxobutyric acids
    发明人:NAITO KENZO; ISHIBASHI YUKIO; SHINBO HARUO
    权利人:TAKEDA CHEMICAL INDUSTRIES LTD
    摘要:An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.

    专利号:US-7452990-B2
    优先权日:2002-12-26
    标题 :Intermediates for synthesis of cephalosporins and process for preparation of such intermediates
    发明人:DATTA DEBASHISH; DANTU MURALIKRISHNA; MISHRA BRIJKISHORE; SHARMA POLLEPEDDI LAKSHMI NARAYANA
    权利人:LUPIN LTD
    摘要:A novel 4-halo-2-oxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics n nwhereinn n X is chlorine or bromine; R is hydrogen, C 1-4 alkyl group, an easily removable hydroxyl protective group, —CH 2 COOR 5 , or —C(CH 3 ) 2 COOR 5 , wherein R 5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV 1 ), n nwherein X, R and R 5 are as defined above, with N,N-dimethylformiminium chloride chlorosulphate of formula (VII)n n nin an organic solvent at a temperature ranging from −30° C. to −15° C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.

    专利号:US-9006421-B2
    优先权日:2013-03-14
    标题 :Cephalosporin compositions and methods of manufacture
    发明人:LAI JAN-JI; PATHARE PRADIP M; KOLLA LAXMA; SORET ADRIEN F
    权利人:CUBIST PHARM INC
    摘要:Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.

    专利号:US-2006135761-A1
    优先权日:2002-12-26
    标 题 :Novel intermediates for synthesis of cephalosporins and process for preparation of such intermediates
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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Eicken A, Schöber JG, Roos R, Machka K. Cerebrospinal fluid penetration of cefmenoxime in children with bacterial meningitis. Infection. 1991 Nov-Dec;19(6):406-8. Japanese.
    4: Kita Y, Itakura K, Tsuchiya K, Imada A. Pharmacokinetics of SCE-1141, a stereoisomer of cefmenoxime, in rats. J Antimicrob Chemother. 1986 Feb;17(2):205-13.
    6: Sennello LT, Quinn D, Rollins DE, Tolman KG, Sonders RC. Effect of probenecid on the pharmacokinetics of cefmenoxime. Antimicrob Agents Chemother. 1983 Jun;23(6):803-7.

    合成参考文献


    参考文献:10.1177/106002809603000919
    摘要:Dalla Costa T, Derendorf H. AUIC--a general target for the optimization of dosing regimens of antibiotics Ann Pharmacother. 1996 Sep;30(9):1024–8. doi: 10.1177/106002809603000919.
    参考文献:10.1007/s00134-002-1212-y
    摘要:Lipman J, Gous AG, Mathivha LR, Tshukutsoane S, Scribante J, Hon H, Pinder M, Riera-Fanego JF, Verhoef L, Stass H. Ciprofloxacin pharmacokinetic profiles in paediatric sepsis: how much ciprofloxacin is enough Intensive Care Med. 2002 Apr;28(4):493–500. doi: 10.1007/s00134-002-1212-y.
    参考文献:10.2165/00044011-199815060-00010
    摘要:Owens CA, Ambrose PG, Quintiliani R, Nightingale CH, Nicolau DP. Infusion phlebitis: relative incidence associated with cefuroxime administered by intermittent and continuous infusion. Clin Drug Investig. 1998;15(6):531–5. doi: 10.2165/00044011-199815060-00010.
    参考文献:10.2165/00044011-199816040-00008
    摘要:Cazzola M, Matera MG, Donner CF. Pharmacokinetics and pharmacodynamics of newer oral cephalosporins: implications for treatment of community-acquired lower respiratory tract infections. Clin Drug Investig. 1998;16(4):335–46. doi: 10.2165/00044011-199816040-00008.
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