CAS: 97519-39-6; Ceftibuten

该化合物是第三代口服甲状腺素抗生素抗生素,其活动范围广泛,可以防治克氏阴性细菌和一些克氏阳性细菌,其主要优点包括生物利用率高,抗乙状乳腺稳定,以及因其长期的半衰期而方便的每日一次剂量疗法.Ceftibuten显示出对常见呼吸道和尿道病原体,包括流感嗜血杆菌,莫拉西拉卡西拉腹腔和大肠杆菌的抗生素的功效.其zwitter结构可增强组织渗透,特别是在呼吸道中的渗透.抗生素主要在尿液中未变,适合治疗非复杂尿道感染.Ceftibuten对肠微生物的最小影响和药物相互作用的低温性进一步有助于其临床用途.

结构式图片

欧盟法规

C&L通报

上下游产品

头孢克洛 Cefaclor 53994-73-3
Bis(Diphenylmethyl) 7(R)-Glutaroylaminoceph-3-Em-4-Carboxylate
Bis(Diphenylmethyl) 7(R)-Glutaroylamino-3-Hydroxyceph-3-Em-4-Carboxylate
Bis(Diphenylmethyl) 3-Chloro-7(R)-Glutaroylaminoceph-3-Em-4-Carboxylate
7-Amino-3-No-Cephalosporin-4-Carboxylic Acid Benzhydryl 36923-21-4
Diphenylmethyl 7-Amino-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylate 36923-21-4
Benzhydryl (6R,7R)-7-[(5-Benzhydryloxy-5-Oxopentanoyl)Amino]-3-Methylsulfonyloxy-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Octane-2-Carboxylate
Benzhydryl (6R,7R)-7-[(5-Benzhydryloxy-5-Oxopentanoyl)Amino]-3-Hydroxy-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Octane-2-Carboxylate

合成工艺路线路线简述

  • 53994-69-7 + 97518-86-0 = 97519-39-6
    反应条件:1.1 Reagents: Magnesium Solvents: 2-Methyltetrahydrofuran,Water; 10 Min,30 °C1.2 3 H,30 °C1.3 Reagents: Sodium Hydroxide Solvents: Isopropanol,Water; 20 °C; 1 H,30 °C; Rt -> 20 °C
    标题:A Green Method For Preparation Of Ceftibuten
    参考文献:China]

    2569684-82-6 = 97519-39-6
    反应条件:1.1 Reagents: Silica; 1.2 H,80 °C
    标题:Method For Preparing Ceftibuten
    参考文献:China]

    414866-39-0 = 97519-39-6
    反应条件:1.1 Reagents: Aluminum Chloride Solvents: Anisole1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Ceftibuten: Development Of A Commercial Process Based On Cephalosporin C. Part Iii. Process For The Conversion Of 3-Exomethylene-7(R)-Glutaroylaminocepham-4-Carboxylic Acid 1(S)-Oxide To Ceftibuten
    作者:Bernasconi,Ermanno; Lee,Junning; Sogli,Loris; Walker,Derek
    参考文献:Organic Process Research & Development 日期:2002 卷标:6(2) 页码:169-177]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Bridge Linkers Used For Specific Conjugation Of Two Or More Cytotoxic Agents To A Cell-Binding Molecule
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Bridge Linkers Used For Specific Conjugation Of A Cytotoxic Agent To A Cell-Binding Molecule
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Novel Bridge Linkers Containing An Acetylenedicarbonyl Group For Specific Conjugation Of A Cytotoxic Agent To A Cell-Binding Molecule
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Synthesis Of Cephalosporin Derivatives For Treating Bacterial Infections
    参考文献:United States]

    = 97519-39-6 [标题:Reaction Conditions
    标题:The Synthesis Of 3-Hydroxycephalosporin Compounds
    作者:Li,Minghai; Wang,Wei; Jiang,Ning
    参考文献:Guowai Yiyao Kangshengsu Fence 日期:2009 卷标:30(5) 页码:229-235]

    174761-17-2 = 97519-39-6
    反应条件:1.1 Reagents: Aluminum Chloride Solvents: Anisole; 1 H,Rt; 2 H,Rt; Rt -> 0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 40 Min,< 15 °C
    标题:Method For Synthesizing Ceftibutene
    参考文献:China]

    174761-17-2 = 97519-39-6
    反应条件:1.1 Reagents: Aluminum Chloride Solvents: Anisole; 0 °C; 45 Min,0 °C; 0 °C -> 20 °C; 1 H,20 °C; 20 °C -> -5 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 20 Min,0 °C
    标题:Preparation Method Of Ceftibuten
    参考文献:China]

    2209855-00-3 = 97519-39-6 [标题:Reaction Conditions
    标题:Process For The Preparation Of 3-Sulfonyloxy-3-Cephem Compounds
    参考文献:Japan]

    2209852-05-9 = 97519-39-6
    反应条件:1.1 Reagents: Acetylacetone,Aluminum Chloride,Hydrochloric Acid Solvents: Anisole,Water
    标题:Process For The Preparation Of Cephem Compounds
    参考文献:Japan]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Trans Isomer Of Ceftibuten
    参考文献:China]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Diazabicyclooctane Derivative As β-Lactamase Inhibitor
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Method For Refining High-Purity Ceftibuten Using Acetonitrile And Activated Carbon
    参考文献:China]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Specific Conjugation Bridge Linkers And Immunoconjugates And Methods Of Using Them
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of Hydrophilic Linkers For The Conjugation Of A Cytotoxic Agent Or A Chromophore To A Cell-Binding Molecule
    参考文献:World Intellectual Property Organization]

    = 97519-39-6 [标题:Reaction Conditions
    标题:Preparation Of 2-Aminothiazole-4-Acetic Acids
    参考文献:India]

    = 97519-39-6 [标题:Reaction Conditions
    标题:An Improved Process For The Manufacture Of 3-Hydroxy-3-Cephem Derivatives
    参考文献:India
Diphenylmethyl (6R,7R)-7-[(E,Z)-2-(2-Benzyloxycarbonylamino-4-Thiazolyl)-4-(3-Methyl-2-Butenyloxycarbonyl)-2-Butenoylamino]-8-Oxo-5-Thia-1-Azabicyclo[4,2,0]oct-2-Ene-2-Carboxylate置于aluminum (Iii) Chloride,苯甲醚,盐酸体系中,用 水 作为反应溶剂,化学反应 0.5H,反应生成 头孢布坦
参考文献:Ceftibuten:开发基于头孢菌素 C 的商业工艺.第三部分.将 3-Exomethylene-7(R)-Glutaroylaminocepham-4-Carboxy 酸 1(S)-Oxide 转化为 Ceftibuten 的方法
标题:Ceftibuten:开发基于头孢菌素 C 的商业工艺.第三部分.将 3-Exomethylene-7(R)-Glutaroylaminocepham-4-Carboxy 酸 1(S)-Oxide 转化为 Ceftibuten 的方法
摘要:上述论文(bernasconi,E.;lee,J.;roletto,J.;sogli,L.;walker,D. Org. Process Res. Dev. 2002,6,152 和 Bernasconi,E.;genders,D. ; Lee,J.; Longoni,D.; Martin,Cr; Menon,V.; Roletto,J.; Sogli,L.; Walker,D.; Zappi,G.; Zelenay,P.; Zhang,H. Org . Process Res. Dev. 2002,6,158) 描述了一种用于制备 3-Exomethylene-7(R)-Glutaroylaminocepham-4-Carboxy Acid 1(S)-Oxide (3) 的高产全水性方法通过酶转化和电化学还原从发酵的头孢菌素 C 肉汤中提取,无需
DOI:10.1021/op010071Y

海关参考信息

专利信息


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-5847116-A
优先权日:1994-12-09
标 题 :Process for the preparation of intermediates useful in the synthesis of cephalosporins
发明人:WALKER DEREK; LEE JUNNING; MARTIN CHARLES R; ZHANG HAIYAN; SOGLI LORIS; BERNASCONI ERMANNO; MENON VINOD PARAKKAL
权利人:SCHERING CORP; ANTIBIOTICOS SA
摘要:A process is described for preparing 3-exomethylene cephalosporanic acid derivatives for use in the synthesis of cephalosporin antibiotics such as ceftibuten. The process comprises electrochemical reduction of a compound of the formula (IV) ##STR1## wherein: R 3 is ##STR2## is an optional sulfoxide group; n is 2 or 3; R 1 is H and R is H or NHR 2 , where R 2 is H or a protecting group selected from C 6 H 5 CH 2 OC(O)--, C 6 H 5 C(O)-- or C 1 -C 6 alkoxy-C(O)--; or wherein R and R 1 together with the carbon atom to which they are attached comprise --C(O)--, and produces the desired 3-exomethylene compounds with low levels of the corresponding 3-methyl tautomers.

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:US-2022233673-A1
优先权日:2019-06-04
标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
发明人:BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.

专利号:US-10933051-B2
优先权日:2017-06-09
标 题 :Carbapenem compounds and compositions for the treatment of bacterial infections
发明人:CHOI WOO-BAEG; TOMIOKA TAKASHI; JOO HYUNG-YEUL; TRUONG PHONG; MIN BRIAN
权利人:FOB SYNTHESIS INC
摘要:The present invention provides carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections, including drug resistant or multiple-drug resistant 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.
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主要参考文献


1: Demirel I, Kruse R, Önnberg A, Persson K. Ceftibuten-induced filamentation of extended spectrum beta lactamase (ESBL)-producing uropathogenic Escherichia coli alters host cell responses during an in vitro infection. Microb Pathog. 2015 Jan;78:52-62. doi: 10.1016/j.micpath.2014.11.015. Epub 2014 Nov 27. Review. doi: 10.1007/s00467-008-0996-6. Epub 2008 Sep 26. Polish.
20: Maraki S, Barbounakis E, Chatzinikolaou I, Anatoliotakis N, Plataki M, Tselentis Y, Samonis G. Effects of cefepime, cefixime and ceftibuten on murine gut colonization by Candida albicans. Chemotherapy. 1998 Nov-Dec;44(6):405-8.

合成参考文献


参考文献:10.1007/bf01743360
摘要:Van Vlem B, Vanholder R, De Paepe P, Vogelaers D, Ringoir S. Immunomodulating effects of antibiotics: literature review. Infection. 1996 Jul;24(4):275–91. doi: 10.1007/bf01743360.
参考文献:10.1007/s001060050401
摘要:Maurer J, Mann W. [Sinusitis in children]. HNO. 1999 Apr;47(4):301–10. doi: 10.1007/s001060050401.
参考文献:10.1007/s101560200011
摘要:Tanaka M, Nakayama H, Tunoe H, Egashira T, Kanayama A, Saika T, Kobayashi I, Naito S. A remarkable reduction in the susceptibility of Neisseria gonorrhoeae isolates to cephems and the selection of antibiotic regimens for the single-dose treatment of gonococcal infection in Japan. J Infect Chemother. 2002 Mar;8(1):81–6. doi: 10.1007/s101560200011.
摘要:Vilaichone A, Watana D, Chaiwatanarat T. Oral ceftibuten switch therapy for acute pyelonephritis in children. J Med Assoc Thai. 2001 Jun;84 Suppl 1():S61–7.
参考文献:10.1007/bf02725629
摘要:Aggarwal A, Rath S. Cefpodoxime - utility in respiratory tract infections and typhoid fever. Indian J Pediatr. 2004 May;71(5):413–5. doi: 10.1007/bf02725629.
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