其它别名[6R-[6alpha,7beta(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]°Ct-2-ene-2-carboxylic acid sodium salt
专利号:WO-2005105813-A1 优先权日:2004-04-28 标 题 :Improved process for the manufacture of ceftriaxone sodium 发明人:JAWEED MUKARRAM SIDDIQUI MOHAM; NAITHANI PANKAJ KUMAR; PUROHIT MANISH; POKALWAR RAJKUMAR UDHAVRAO 权利人:WOCKHARDT LTD; JAWEED MUKARRAM SIDDIQUI MOHAM; NAITHANI PANKAJ KUMAR; PUROHIT MANISH; POKALWAR RAJKUMAR UDHAVRAO 摘要:A process for the production of (6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2-synÂmethoxyimino)acetamido]-3-[[2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3Âyl)thio]methyl]-8-oxo-5-thia-l-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid (Ceftriaxone acid) in water is discussed. The synthesis is effected by condensing (7R)-7-Amino-3Âdeacetoxy-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]cephalosporanic acid (7-ACT) with 2-(2-chloroacetamido-4-thiazolyl)-2-syn-methoxyiminoacetyl chloride followed be deblocking amino function. Finally, (6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2-synÂmethoxyimino)acetamido]-3-[[2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3Âyl)thio]methyl]-8-oxo-5-thia-l-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid (Ceftriaxone acid) is converted into Ceftriaxone disodium hemiheptahydrate in aqueous acetone using sodium-2-ethylhexanoate as sodium source. Isolation steps at every stage are quite short. The purity of the final product is obtained in more than 99 % by HPLC profile.
1: Xue J, Jia YH, Li J, Yin LH, Hu CQ. [Subtype classification of ceftriaxone sodium and its influence on the quality of product]. Yao Xue Xue Bao. 2014 Jul;49(7):1034-8. Chinese. doi: 10.1002/jbt.21446. Epub 2012 Nov 21. Epub 2013 Aug 16. doi: 10.1002/jcla.21551. doi: 10.1002/pds.3232. Epub 2012 Jul 4. Review. doi: 10.3390/pharmaceutics4030334. 7: Zaki NM, Hafez MM. Enhanced antibacterial effect of ceftriaxone sodium-loaded chitosan nanoparticles against intracellular Salmonella typhimurium. AAPS PharmSciTech. 2012 Jun;13(2):411-21. doi: 10.1208/s12249-012-9758-7. Epub 2012 Feb 23. 8: Tange M, Yoshida M, Nakai Y, Uchida T. Comparison between original and generic versions of ceftriaxone sodium preparation for injection: compatibility with calcium-containing product. Chem Pharm Bull (Tokyo). 2012;60(4):429-34. doi: 10.1016/j.jpba.2011.01.020. Epub 2011 Jan 25. doi: 10.1097/MAJ.0b013e3181ec063b. doi: 10.1111/j.1469-0691.2010.03122.x. doi: 10.3109/10717540903334959.
合成参考文献
参考文献:10.1007/s12245-009-0116-9 摘要:Ngo AS, Oh JJ, Chen Y, Yong D, Ong MEH. Intraosseous vascular access in adults using the EZ-IO in an emergency department. International Journal of Emergency Medicine. 2009 Aug 11;2(3):155–60. doi: 10.1007/s12245-009-0116-9. 参考文献:10.1007/s10895-011-0917-0 摘要:Shah J, Jan MR, Shah S, Naeem M. Spectrofluorimetric protocol for ceftriaxone in commercial formulation and human plasma after condensation with formaldehyde and ethyl acetoacetate. J Fluoresc. 2011 Nov;21(6):2155–63. doi: 10.1007/s10895-011-0917-0. 参考文献:10.1007/s10384-011-0053-z 摘要:Li SY, Birnbaum AD, Tessler HH, Goldstein DA. Posterior syphilitic uveitis: clinical characteristics, co-infection with HIV, response to treatment. Japanese Journal of Ophthalmology. 2011 Sep 01;55(5):486–94. doi: 10.1007/s10384-011-0053-z. 参考文献:10.1007/s11748-010-0718-4 摘要:Kasama K, Suzuki S, Isomatsu Y, Minami T, Matsuki Y, Masuda M. In situ graft replacement and rectus abdominis muscle flap transfer for infected thoracoabdominal aortic aneurysm after gastrectomy. General Thoracic and Cardiovascular Surgery. 2011 Jul 14;59(7):485–7. doi: 10.1007/s11748-010-0718-4. 参考文献:10.1186/1471-230x-11-79 摘要:Thiel K, Schenk M, Etspüler A, Schenk T, Morgalla MH, Königsrainer A, Thiel C. A simple dummy liver assist device prolongs anhepatic survival in a porcine model of total hepatectomy by slight hypothermia. BMC Gastroenterol. 2011 Jul 14;11():79.