S-泮托拉唑的研究进展
Recent Progress in Preparation of S-Pantoprazole

作者: 王 婷 , 曾银凤 , 朱 槿 , 黄晴菲 , 王启卫 :中国科学院成都有机化学研究所,四川 成都; 彭丽君 , 王红丹 :常州化学研究所,江苏 常州;

关键词: 泮托拉唑手性拆分不对称氧化Pantoprazole Chiral Resolution Asymmetric Oxidation

摘要:
泮托拉唑是一种抑制胃酸分泌的质子泵抑制剂。临床研究表明,与消旋体及其对映体相比,S-泮托拉唑抑酸效果好,生物利用度高,毒副作用低。目前报道的制备S-泮托拉唑的方法主要是手性拆分和不对称氧化。本文简要概述了S-泮托拉唑的制备研究状况。

Abstract: Pantoprazole is one of the blockbuster gastric proton pump inhibitors (PPIs). The clinical study showed that S-pantoprazole provides better acid control, higher bio-availability and lower side effects compared to the racemic pantoprazole and R-panto-prazole. It is reported that the optical pure S-pantoprazole could be prepared by chiral resolution and catalytic asymmetric oxidation. This review briefly described the deve-lopment of the preparation method for the optically pure S- pantoprazole.

文章引用: 王 婷 , 曾银凤 , 彭丽君 , 王红丹 , 朱 槿 , 黄晴菲 , 王启卫 (2015) S-泮托拉唑的研究进展。 有机化学研究, 3, 139-146. doi: 10.12677/JOCR.2015.34018

参考文献

[1] 宋伟国, 夏艳. 质子泵抑制剂研究进展[J]. 中国药业, 2011, 20(9): 80-82.

[2] Mullin, J.M., Gabello, M., Murray, L.J., et al. (2009) Proton Pump Inhibitors: Actions and Reactions. Drug Discovery Today, 14, 648-660.

[3] Gray, N.M. and Mass, M. (1999) Methods and Compositions for Treating Gastrc Disorders Using Optically Pure (-) Panto-prazole. US Patent 5888535.

[4] Cao, H., Wang, M.W., Sun, L.X., et al. (2005) Pharmacodynamic Comparison of Pantoprazole Enantiomers: Inhibition of Acid-Related Lesions and Acid Secretion in Rats and Guinea-Pigs. Journal of Pharmacy and Pharmacology, 57, 923-927.
http://dx.doi.org/10.1211/0022357056361

[5] Cao, H., Wang, M.W., Jia, J.H., et al. (2004) Comparison of the Effects of Pantoprazole Enantiomers on Gastric Mucosal Lesions and Gastria Epithelial Cells in Rats. Journal of Health Science, 50, 1-8.
http://dx.doi.org/10.1248/jhs.50.1

[6] 魏云, 唐映红, 吉兰, 等. 泮托拉唑钠抗胃溃疡药理研究[J]. 中国医药工业杂志, 2000, 31(3): 116-118.

[7] Konstanz, R., Leinfelden-Echterdingen, I.A.K., Radolfzell, M.S., et al. (2011) Dosage Form Containing (S)-Pantoprazole as Active Ingredient. US Patent 20110171303A1.

[8] Bernhard, K. and Jorg, S.-B. Separation of Enantiomers. DE4035455.

[9] 赵志全. S-泮托拉唑及盐的新制备方法[P]. 中国专利, CN200810110447. 2008-09.

[10] 苏晓霞. 光学纯泮托拉唑的制备方法[P]. 中国专利, CN200810150111. 2009-01-14.

[11] Bandi, P.R., Rapolu, R.R., Rapolu, R.R., Dasari, R.R., Bandi, V.K. and Ayalasomayajula, S.S. (2014) Optical Resolution of Substituted 2-(2-Pyridinylmethylsulphinyl)-1H-benzimidazoles. Patent No. WO2011042910A2.

[12] Maria, A.M., Capozzi, C.C., Giuseppe, F., Francesco, N. and Paolo, T. (1999) Enantioselec-tive Catalytic Oxidation of (Arylthio)-or (Alkylthio)methylphosphonates as a Route to Enantiomeric Pure Aryl Alkyl or Dialkyl Sulfoxides. The Journal of the American Chemical Society, 121, 4708-4709.
http://dx.doi.org/10.1021/ja982836w

[13] Holland, H.L. (2001) Biotransformation of Organic Sulfides. Natural Product Reports, 18, 171-181.
http://dx.doi.org/10.1039/b002681f

[14] Hoveyda, A.H., Evans, D.A. and Fu, G. (1993) Substrate-Directable Chemical Reactions. Chemical Reviews, 93, 1307- 1370.
http://dx.doi.org/10.1021/cr00020a002

[15] Adam, W., Korb, M.N. and Roschmann, K.J. (1998) Titanium-Catalyzed Asymmetric Sulfoxidation of Alkyl Aryl Sulfides with Optically Actibe Hydroperoxides. The Journal of Organic Chemistry, 63, 3423-3428.
http://dx.doi.org/10.1021/jo980243y

[16] Schenk, W.A. (1997) Synthesis of (R)-Sulforaphane Using [CpRu(R, R)-CHIRAPHOS]+ as Chiral Auxiliary. Chemistry—A European Journal, 3, 713-716.
http://dx.doi.org/10.1002/chem.19970030510

[17] Larsson, E.M., Stenhede, U.J., Sorensen, H., von Unge, P.O.S. and Cotton, H.K. (1996) Patent No. WO 9602535.

[18] Kohl, B., Muller, B. and Steffen, R. (2006) Process for Pare-paring (S)-Pantoprazole. US Patent No. 20060167262A1.

[19] 王庆和, 程卯生. 手性亚砜类化合物的制备方法[P]. 中国专利, 200710010273.4, 2012.

[20] Moreshwar, G.M., Sudarshan, M.G., Dagesing, M.R., Ramanlal, M.S., Ke-shav, G.M., Ramsing, R.M. and Sadashiv, G.P. (2008) A Process of Sulfoxidation of Biologically Active Compounds. Patent No. WO 2008152462A1.

[21] Jiang, B., Zhao, X.L., Dong, J.J. and Wang, W.J. (2009) Catalytic Asymmetric Oxidation of Heteroaromatic Sulfides with tert-Butyl by Droperoxide Catalyzed by a Titanium Complex with a New Chiral 1,2-Diphenylethane-1,2-diol Ligand. European Journal of Organic Chemistry, 2009, 987-991.
http://dx.doi.org/10.1002/ejoc.200801139

[22] Liao, J., Tian, T., Huan, Q.F., Deng, J.G. and Zhu, J. (2009) Process for Preparing Sulfoxide Compounds. Patent No. WO 2009114981.

[23] Che, G.Y., Xiang, J., Tian, T., Huang, Q.F., Cun, L.F., Liao, J., Wang, Q.W., Zhu, J. and Deng, J.G. (2012) Catalytic Asymmetric Oxidation of 1H-Benzimidazolyl Pyridinylmethyl Sulfides with Cumene Hydroperoxide Catalyzed by Titanium Complex with (S,S)-N,N’-Dibenzyl Tartramide Ligand. Tetrahedron: Asymmetry, 23, 457-460.
http://dx.doi.org/10.1016/j.tetasy.2012.03.017

[24] 曾银凤, 黄晴菲, 邹胜, 向静, 朱槿, 邓金根, 王启卫. 不对称催化氧化制备(S)-泮托拉唑[J]. 合成化学, 2013, 21(5): 627-629.

[25] 卢进城. S-泮托拉唑钠的合成工艺改进[J]. 药学研究, 2014, 33(10): 617-618.

分享
Top