CAS: 82547-81-7; Cefteram Pivoxil

该化合物是第三代甲状腺素抗生素抗生素原药,目的是提高口服生物利用率.在使用这种药后,会进行水解,以活性形式(cefteram)为药用,显示对抗乳性细菌和阴性细菌的广泛活动.其主要优势包括:抗β乳腺的稳定性得到提高,确保抗抗菌菌株的功效,以及长血清半衰期的有利药用植物基因特征,允许较少的剂量.该化合物显示出高组织渗透,特别是在呼吸道和尿道中,使其适合治疗这些地区的感染.其酯化的胆固磷酸会促进更好的肠吸收,与早期的口服功能有限的胸腺素不同.临床应用包括呼吸道,尿道和软组织感染.

英文名称Cefteram Pivoxil
中文名称头孢特仑新戊酯
IUPAC名称(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester
其它别名Pivaloyloxymethyl (Z)-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylate
CAS编号82547-81-7
MFCD编号:MFCD00941401
FDA UNII编号:0OD86RT58C
分子式:C22H27N9O7S2
分子量:593.64
产品CID: 1816020
产品分类原料药 → 抗生素类药物 → 头孢菌素类药

相似结构搜索
InChIKey: UIYAXIPXULMHAI-JLGRZTKVSA-N
UIYAXIPXULMHAI-JLGRZTKVSA-N…
计算化学: 氢键受体数15.0氢键供体数2.0可旋转键数12.0

物理性质

熔点125-128°C
沸点125-128 °C
密度1.3216 (粗估)
pKa:8.08±0.60(预测)
PSA:259.65
LogP:0.7249
折射率1.7400 (估算)
溶解性DMSO: 0.01 mg/mL (0.02 Mm);
外观形态白色至淡黄色固体
储存条件防潮, -20°C 冰箱, 在惰性气其中
产品应用该化合物是甲状腺素抗生素,用于治疗细菌引起的感染,通过杀死细菌或防止细菌生长,CEFDITOREN PIVXIL也用于治疗一些喉部和肺部感染,包括支气管炎和三联疫苗,还用于治疗某些皮肤感染.

上下游产品

iodomethyl pivaloate cefteram 7-Amin°Cephalosporanic acid 7-amino-3-[2-(5-methyl-2H-tetrazolyl)methyl]cephalosporanic acid(2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(5-methyl-tetrazol-2-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]°Ct-3-ene-2-carboxylic acid (2R,6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(5-methyl-tetrazol-2-ylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]°Ct-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester cefteram

合成工艺路线路线简述

合成目标产物 Cefteram Pivoxil 主要起始原料 Iodomethyl Pivalate And Cefteram Pivoxil
65872-41-5 + 144-62-7 + 98157-80-3 = 82547-81-7
反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Dichloromethane,Dimethylacetamide1.2 -
标题:Studies On β-Lactam Antibiotics For Medicinal Purpose. Xviii. Synthesis And Structure-Activity Relationships Of 7β-[(Z)-2-(2-Aminothiazol-4-Yl)-2-Methoxyiminoacetamido]-3-Substituted Methyl-3-Cephem-4-Carboxylic Acid Derivatives
作者:Sadaki,Hiroshi; Et Al
参考文献:Yakugaku Zasshi 日期:1986 卷标:106(2) 页码:129-46]

65872-41-5 = 82547-81-7
反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Dimethylformamide,Tetrahydrofuran1.2 Reagents: Triethylamine Solvents: Dichloromethane
标题:Studies On β-Lactam Antibiotics For Medicinal Purposes. Xix. Synthesis And Structure-Activity Relationships Of 7β-(Acylamino)-3-[(5-Methyl-2H-Tetrazol-2-Yl)Methyl]-3-Cephem-4-Carboxylic Acid,7β-(Acylamino)-3-[(5-Chloro-1,2,4-Triazol-1-Yl)Methyl]-3-Cephem-4-Carboxylic Acid,And Their Derivatives
作者:Sadaki,Hiroshi; Et Al
参考文献:Yakugaku Zasshi 日期:1986 卷标:106(2) 页码:147-53]

53064-79-2 + 82547-58-8 = 82547-81-7
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol,Dimethylformamide; 20 Min,20 °C1.2 20 °C; 2.5 H,20 °C
标题:Synthesis Of Cefteram Pivoxil
作者:Shi,Ke-Jin; Et Al
参考文献:Zhongguo Kangshengsu Zazhi 日期:2014 卷标:39(7) 页码:507-509]

53064-79-2 + 82547-58-8 = 82547-81-7
反应条件:1.1 Reagents: Dicyclohexylamine Solvents: Dimethylacetamide
标题:Studies On Orally Active Cephalosporin Esters
作者:Fujimoto,Koichi; Et Al
参考文献:Journal Of Antibiotics 日期:1987 卷标:40(3) 页码:370-84]

80756-85-0 + 82549-51-7 = 82547-81-7
反应条件:1.1 Reagents: Triethylamine,Sodium Pyrosulfite Solvents: Dichloromethane; Rt -> 0 °C; 3 H,0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Ph 2.5 - 3,0 °C -> 5 °C2.1 Reagents: Sodium Methoxide Solvents: Methanol,Dimethylformamide; 20 Min,20 °C2.2 20 °C; 2.5 H,20 °C
标题:Synthesis Of Cefteram Pivoxil
作者:Shi,Ke-Jin; Et Al
参考文献:Zhongguo Kangshengsu Zazhi 日期:2014 卷标:39(7) 页码:507-509]

82549-51-7 = 82547-81-7
反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Acetone1.2 Reagents: Oxalic Acid2.1 Reagents: Phosphorus Oxychloride Solvents: Dichloromethane,Dimethylacetamide2.2 -
标题:Studies On β-Lactam Antibiotics For Medicinal Purpose. Xviii. Synthesis And Structure-Activity Relationships Of 7β-[(Z)-2-(2-Aminothiazol-4-Yl)-2-Methoxyiminoacetamido]-3-Substituted Methyl-3-Cephem-4-Carboxylic Acid Derivatives
作者:Sadaki,Hiroshi; Et Al
参考文献:Yakugaku Zasshi 日期:1986 卷标:106(2) 页码:129-46]

4076-36-2 + 957-68-6 = 82547-81-7
反应条件:1.1 Reagents: (T-4)-(Dimethyl Carbonate-Ko′′)Trifluoroboron; 5 H,35 °C1.2 Reagents: Potassium Hydroxide Solvents: Water; 2 H,Ph 3.5,35 °C -> 5 °C2.1 Reagents: Triethylamine,Sodium Pyrosulfite Solvents: Dichloromethane; Rt -> 0 °C; 3 H,0 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Ph 2.5 - 3,0 °C -> 5 °C3.1 Reagents: Sodium Methoxide Solvents: Methanol,Dimethylformamide; 20 Min,20 °C3.2 20 °C; 2.5 H,20 °C
标题:Synthesis Of Cefteram Pivoxil
作者:Shi,Ke-Jin; Et Al
参考文献:Zhongguo Kangshengsu Zazhi 日期:2014 卷标:39(7) 页码:507-509

7-氨基头孢烷酸置于硫酸,四丙基碘化铵体系中,用 1,4-二氧六环,二氯甲烷作为反应溶剂,化学反应 6.08H,反应生成头孢特仑新戊酯
参考文献:一种头孢特仑新戊酯的制备方法
标题:一种头孢特仑新戊酯的制备方法
摘要:本发明涉及一种头孢特仑新戊酯的制备方法,该方法包括如下步骤:以7‑aca及5‑甲基四氮唑为起始原料,在h2So4的作用下,反应生成7‑mtca;氨噻唑酸乙酯氨基保护后,在alme3催化下与7‑mtca反应生成中间体ⅰ;该中间体ⅰ在相转移催化剂及酸吸附剂的作用下与特戊酸碘甲酯进行酯化反应,并脱氨基保护,得目标产品头孢特仑新戊酯.本发明反应条件温和,产品纯度高,收率高,工艺稳定,易于放大,适合于工业化生产.

海关参考信息

2901210000-乙烯
2901220000-丙烯
2905121000-正丙醇
2912110000-甲醛
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专利信息

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, â€”CH 2 COOR 5 , or â€”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 âˆ’30Â° C. to âˆ’15Â° 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-2006135761-A1
优先权日:2002-12-26
标题 :Novel intermediates for synthesis of cephalosporins and process for preparation of such intermediates

专利号:WO-2004058695-A1
优先权日:2002-12-26
标题 :Novel intermediates for synthesis of cephalosporins and process for preparation of such intermediates

专利号:EP-1575913-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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主要参考文献

1: Yue Y, Wang J, Zhao Y, Li S, Han J, Zhang Y, Zhang Q, Han F. Impurity profiling of Cefteram pivoxil based on Fourier transform ion cyclotron resonance MS. J Pharm Biomed Anal. 2020 Nov 30;191:113591. doi: 10.1016/j.jpba.2020.113591. Epub 2020 Aug 29.
14:1599-1604. doi: 10.2147/TCRM.S168696.
3: Hosaka S, Okamura Y, Tokunaga Y. Preparation of Fine Particles with Improved Solubility Using a Complex Fluidized-Bed Granulator Equipped with a Particle- Sizing Mechanism. Chem Pharm Bull (Tokyo). 2016;64(6):644-9. doi: 10.1248/cpb.c15-00640. Working Group of Total Anti- biogram Study Group; Research Laboratories; Development Division; Toyama Chemical Co Ltd. [Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibacterial agents in Gifu and Aichi prefectures (2011-2012)]. Jpn J Antibiot. 2015 Aug;68(4):225-42. Japanese. 21(4):277-83. doi: 10.1016/j.jiac.2014.12.006. Epub 2014 Dec 26. 66(5):265-82. Japanese. Working Group of Tokai Anti-biogram Study Group. [Antibacterial susceptibility surveillance of Haemophilus influenzae isolated from pediatric patients in Gifu and Aichi prefectures (2009-2010)]. Jpn J Antibiot. 2012 Oct;65(5):305-21. Japanese. Research Laboratories; Toyama Chemical Co., Ltd; Working Group of Tokai Anti-biogram Study Group. [Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibacterial agents in Gifu and Aichi prefecture (2008-2009)]. Jpn J Antibiot. 2012 Feb;65(1):1-14. Japanese. 3(2):132-4. doi: 10.4168/aair.2011.3.2.132. Epub 2011 Feb 14.

合成参考文献

参考文献:10.1128/aac.31.7.1111
摘要:Okamoto S, Hamana Y, Inoue M, Mitsuhashi S. In vitro and in vivo antibacterial activities of T-2588, a new oral cephalosporin, compared with those of other oral beta-lactam antibiotics. Antimicrob Agents Chemother. 1987 Jul;31(7):1111–6.
摘要:Chemotherapy, 34(Suppl