Prospects to the formation and control of potential dimer impurity E of pantoprazole sodium sesquihydrate
|
摘要
Pantoprazole sodium, a substituted benzimidazole derivative, is an irreversible proton pump inhibitor which is primarily used for the treatment of duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease(GERD). The monographs of European Pharmacopoeia(Ph. Eur.) and United States Pharmacopoeia(USP) specify six impurities, viz.; impurities A, B, C, D, E and F, respectively for its active pharmaceutical ingredient(API). The identification and synthesis of all impurities except impurity E are well described in the literature; however, there is no report related to impurity E. The prospects to the formation and controlling of impurity E up to 0.03% in the synthesis of pantoprazole sodium sesquihydrate(PAN) were discussed in detail for the first time. The present work described the journey towards the successful development of an optimal preparation procedure of dimer impurity E. The most plausible mechanism involved in the formation of impurity E has been proposed.
Pantoprazole sodium, a substituted benzimidazole derivative, is an irreversible proton pump inhibitor which is primarily used for the treatment of duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease(GERD). The monographs of European Pharmacopoeia(Ph. Eur.) and United States Pharmacopoeia(USP) specify six impurities, viz.; impurities A, B, C, D, E and F, respectively for its active pharmaceutical ingredient(API). The identification and synthesis of all impurities except impurity E are well described in the literature; however, there is no report related to impurity E. The prospects to the formation and controlling of impurity E up to 0.03% in the synthesis of pantoprazole sodium sesquihydrate(PAN) were discussed in detail for the first time. The present work described the journey towards the successful development of an optimal preparation procedure of dimer impurity E. The most plausible mechanism involved in the formation of impurity E has been proposed.
Pantoprazole sodium, a substituted benzimidazole derivative, is an irreversible proton pump inhibitor which is primarily used for the treatment of duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease(GERD). The monographs of European Pharmacopoeia(Ph. Eur.) and United States Pharmacopoeia(USP) specify six impurities, viz.; impurities A, B, C, D, E and F, respectively for its active pharmaceutical ingredient(API). The identification and synthesis of all impurities except impurity E are well described in the literature; however, there is no report related to impurity E. The prospects to the formation and controlling of impurity E up to 0.03% in the synthesis of pantoprazole sodium sesquihydrate(PAN) were discussed in detail for the first time. The present work described the journey towards the successful development of an optimal preparation procedure of dimer impurity E. The most plausible mechanism involved in the formation of impurity E has been proposed.
引文
[1]B.Kohl,E.Sturm,G.Rainer,Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors,U.S.Pat.4758579(July 19,1988).
[2]B.Kohl,E.Sturm,K.Klemm,et al.,Dialkoxyridines,process for their preparation,their application and medicaments containing them,Eur.Pat.0166287(January 2,1986).
[3]B.Kohl,E.Sturm,J.S.Bilfinger,et al.,(Ht,Kt)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles.4.A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity.The selection of pantoprazole as a clinical candidate,J.Med.Chem.35(1992)1049e1057.
[4]P.Richardson,C.J.Hawkey,W.A.Stack,Proton pump inhibitors,Drugs 56(1998)307e335.
[5]R.A.Murlidhar,S.B.Bhaskar,B.P.Gopinathan,et al.,Process for the preparation of pantoprazole sodium,PCT Pat.Appl.WO 2009066317(July 23,2009).
[6]P.N.Francisco,M.P.Andres,Process for the preparation of pantoprazole,PCTPat.Appl.WO 2006100243(September 28,2006).
[7]V.T.Mathad,S.Govindan,N.K.Kolla,et al.,An improved and single-pot process for the production of pantoprazole substantially free from sulfone impurity,Org.Process Res.Dev.8(2004)266e270.
[8]W.Kyu-Jung,K.Young-Deuck,Process for preparing pantoprazole sodium sesquihydrate,PCT Pat.Appl.WO 2009075516(June 18,2009).
[9]I.Avrutov,M.Mendelovici,Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-1H-benzimidazoles,U.S.Pat.7129358 B2(October31,2006).
[10]I.Avrutov,M.Mendelovici,Processes for the Production of substituted 2-(2-pyridylmethyl)sulfinyl-1H-benzimidazoles,U.S.Pat.Appl.US 20080091024A1(April 17,2008).
[11]F.Chin-Tsai,Method for preparing 2-(2-pyridinylmethylsulfinyl)benzimidazoles,U.S.Pat.7531666 B2(May 12,2009).
[12]P.C.Alberto,A process for the preparation of pantoprazole and intermediates thereof,PCT Pat.Appl.WO 2002028852 A1,(April 11,2002).
[13]R.B.Maimo,J.C.Pardo,L.Coppi,Method for oxidizing a thioether group into a sulfoxide group,U.S.Pat.6603009 B2(August 5,2003).
[14]J.Patrick,A.T.Timothy,Chemical process for the production of sulphinyl derivatives by oxidation of the corresponding co-derivatives with perborates,PCT Pat.Appl.WO 1999047514 A1(September 23,1999).
[15]European Pharmacopoeia-National Formulary,9th ed.,vol.1,2017,pp.3264e3265.
[16]United States Pharmacopeia-National Formulary,[USP 32 NF 27],vol.33,2016,pp.3200.
[17]G.M.Reddy,B.V.Bhaskar,P.P.Reddy,et al.,Structural identification and characterization of potential impurities of pantoprazole sodium,J.Pharmaceut.Biomed.Anal.45(2007)201e210.
[18]S.Pandey,P.Pandey,D.Mishra,et al.,A validated stability indicating HPLCmethod for the determination of process-related impurities in pantoprazole bulk drug and formulations,Braz.J.Pharm.Sci.49(2013)175e184.
[19]N.V.V.S.S.Raman,K.R.Reddy,A.V.S.S.Prasad,et al.,Validated chromatographic methods for the determination of process related toxic impurities in pantoprazole sodium,Chromatographia 68(2008)481e484.
[20]United States Pharmacopeial Convention,USP Reference Standards.http://static.usp.org/doc/referenceStandards/dailycatalog.pdf.(Accessed September2016).
[21]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),draft revised guidance on impurities in new drug substances,Q3A(R),Fed.Regist.65(140)(2000)45085.
[22]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),draft revised guidance on impurities in new drug substances,Q3B(R),Fed.Regist.65(139)(2000)44791.
[23]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),impurities guidelines for residual solvents,Q3(C),Fed.Regist.62(247)(1997)67377.
[24]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),revised guidance on impurities in new drug substances,Q3A(R),availability.Notice,Fed.Regist.68(2003)6924.
[25]A.K.Awasthi,B.Kumar,M.A.Aga,et al.,An efficient and facile synthesis of D-cycloserine substantially free from potential impurities,Chem.Heterocycl.Comp.53(2017)1248e1253.
[26]A.K.Awasthi,B.Kumar,M.A.Aga,et al.,An efficient,facile synthesis of etoricoxib substantially free from impurities:isolation,characterization and synthesis of novel impurity,ChemistrySelect 2(2017)9722e9725.
[27]K.Venumanikanta,P.Kumar,B.M.Reddy,et al.,A simple and commercially viable process for improved yields of metopimazine,a dopamine D2-receptor antagonist,Org.Process Res.Dev.21(2017)720e731.
[28]S.Sankareswaran,M.Mannam,V.Chakka,et al.,Identification and control of critical process impurities:an improved process for the preparation of dolutegravir sodium,Org.Process Res.Dev.20(2016)1461e1468.
[29]N.Kumar,S.R.Devineni,P.R.Gajjala,et al.,Four process-related potential new impurities in ticagrelor:identification,isolation,characterization using HPLC,LC/ESI-MSn,NMR and their synthesis,J.Pharmaceut.Biomed.Anal.120(2016)248e260.
[30]N.Kumar,S.R.Devineni,G.Singh,et al.,Identification,isolation and characterization of potential process-related impurity and its degradation product in Vildagliptin,J.Pharmaceut.Biomed.Anal.119(2016)114e121.
[31]N.Kumar,S.R.Devineni,S.K.Dubey,et al.,Potential impurities of anxiolytic drug,clobazam:identification,synthesis and characterization using HPLC,LC-ESI/MSnand NMR,J.Pharmaceut.Biomed.Anal.137(2017)268e278.
[32]R.Neelamegam,M.T.Palatnik,J.F.Rini,et al.,Dimerization of phenols and naphthols using an aqueous sodium hypochlorite,Tetrahedron Lett.51(2010)2497e2499.
[33]A.K.Awasthi,L.Kumar,P.Tripathi,et al.,Environmentally benign and facile process for the synthesis of pantoprazole sodium sesquihydrate:phase transformation of pantoprazole sodium heterosolvate to pantoprazole sodium sesquihydrate,ACS Omega 2(2017)5460e5469.
[2]B.Kohl,E.Sturm,K.Klemm,et al.,Dialkoxyridines,process for their preparation,their application and medicaments containing them,Eur.Pat.0166287(January 2,1986).
[3]B.Kohl,E.Sturm,J.S.Bilfinger,et al.,(Ht,Kt)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles.4.A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity.The selection of pantoprazole as a clinical candidate,J.Med.Chem.35(1992)1049e1057.
[4]P.Richardson,C.J.Hawkey,W.A.Stack,Proton pump inhibitors,Drugs 56(1998)307e335.
[5]R.A.Murlidhar,S.B.Bhaskar,B.P.Gopinathan,et al.,Process for the preparation of pantoprazole sodium,PCT Pat.Appl.WO 2009066317(July 23,2009).
[6]P.N.Francisco,M.P.Andres,Process for the preparation of pantoprazole,PCTPat.Appl.WO 2006100243(September 28,2006).
[7]V.T.Mathad,S.Govindan,N.K.Kolla,et al.,An improved and single-pot process for the production of pantoprazole substantially free from sulfone impurity,Org.Process Res.Dev.8(2004)266e270.
[8]W.Kyu-Jung,K.Young-Deuck,Process for preparing pantoprazole sodium sesquihydrate,PCT Pat.Appl.WO 2009075516(June 18,2009).
[9]I.Avrutov,M.Mendelovici,Processes for the production of substituted 2-(2-pyridylmethyl)sulfinyl-1H-benzimidazoles,U.S.Pat.7129358 B2(October31,2006).
[10]I.Avrutov,M.Mendelovici,Processes for the Production of substituted 2-(2-pyridylmethyl)sulfinyl-1H-benzimidazoles,U.S.Pat.Appl.US 20080091024A1(April 17,2008).
[11]F.Chin-Tsai,Method for preparing 2-(2-pyridinylmethylsulfinyl)benzimidazoles,U.S.Pat.7531666 B2(May 12,2009).
[12]P.C.Alberto,A process for the preparation of pantoprazole and intermediates thereof,PCT Pat.Appl.WO 2002028852 A1,(April 11,2002).
[13]R.B.Maimo,J.C.Pardo,L.Coppi,Method for oxidizing a thioether group into a sulfoxide group,U.S.Pat.6603009 B2(August 5,2003).
[14]J.Patrick,A.T.Timothy,Chemical process for the production of sulphinyl derivatives by oxidation of the corresponding co-derivatives with perborates,PCT Pat.Appl.WO 1999047514 A1(September 23,1999).
[15]European Pharmacopoeia-National Formulary,9th ed.,vol.1,2017,pp.3264e3265.
[16]United States Pharmacopeia-National Formulary,[USP 32 NF 27],vol.33,2016,pp.3200.
[17]G.M.Reddy,B.V.Bhaskar,P.P.Reddy,et al.,Structural identification and characterization of potential impurities of pantoprazole sodium,J.Pharmaceut.Biomed.Anal.45(2007)201e210.
[18]S.Pandey,P.Pandey,D.Mishra,et al.,A validated stability indicating HPLCmethod for the determination of process-related impurities in pantoprazole bulk drug and formulations,Braz.J.Pharm.Sci.49(2013)175e184.
[19]N.V.V.S.S.Raman,K.R.Reddy,A.V.S.S.Prasad,et al.,Validated chromatographic methods for the determination of process related toxic impurities in pantoprazole sodium,Chromatographia 68(2008)481e484.
[20]United States Pharmacopeial Convention,USP Reference Standards.http://static.usp.org/doc/referenceStandards/dailycatalog.pdf.(Accessed September2016).
[21]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),draft revised guidance on impurities in new drug substances,Q3A(R),Fed.Regist.65(140)(2000)45085.
[22]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),draft revised guidance on impurities in new drug substances,Q3B(R),Fed.Regist.65(139)(2000)44791.
[23]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),impurities guidelines for residual solvents,Q3(C),Fed.Regist.62(247)(1997)67377.
[24]International Council for harmonisation of technical requirements for pharmaceuticals for human use(ICH),revised guidance on impurities in new drug substances,Q3A(R),availability.Notice,Fed.Regist.68(2003)6924.
[25]A.K.Awasthi,B.Kumar,M.A.Aga,et al.,An efficient and facile synthesis of D-cycloserine substantially free from potential impurities,Chem.Heterocycl.Comp.53(2017)1248e1253.
[26]A.K.Awasthi,B.Kumar,M.A.Aga,et al.,An efficient,facile synthesis of etoricoxib substantially free from impurities:isolation,characterization and synthesis of novel impurity,ChemistrySelect 2(2017)9722e9725.
[27]K.Venumanikanta,P.Kumar,B.M.Reddy,et al.,A simple and commercially viable process for improved yields of metopimazine,a dopamine D2-receptor antagonist,Org.Process Res.Dev.21(2017)720e731.
[28]S.Sankareswaran,M.Mannam,V.Chakka,et al.,Identification and control of critical process impurities:an improved process for the preparation of dolutegravir sodium,Org.Process Res.Dev.20(2016)1461e1468.
[29]N.Kumar,S.R.Devineni,P.R.Gajjala,et al.,Four process-related potential new impurities in ticagrelor:identification,isolation,characterization using HPLC,LC/ESI-MSn,NMR and their synthesis,J.Pharmaceut.Biomed.Anal.120(2016)248e260.
[30]N.Kumar,S.R.Devineni,G.Singh,et al.,Identification,isolation and characterization of potential process-related impurity and its degradation product in Vildagliptin,J.Pharmaceut.Biomed.Anal.119(2016)114e121.
[31]N.Kumar,S.R.Devineni,S.K.Dubey,et al.,Potential impurities of anxiolytic drug,clobazam:identification,synthesis and characterization using HPLC,LC-ESI/MSnand NMR,J.Pharmaceut.Biomed.Anal.137(2017)268e278.
[32]R.Neelamegam,M.T.Palatnik,J.F.Rini,et al.,Dimerization of phenols and naphthols using an aqueous sodium hypochlorite,Tetrahedron Lett.51(2010)2497e2499.
[33]A.K.Awasthi,L.Kumar,P.Tripathi,et al.,Environmentally benign and facile process for the synthesis of pantoprazole sodium sesquihydrate:phase transformation of pantoprazole sodium heterosolvate to pantoprazole sodium sesquihydrate,ACS Omega 2(2017)5460e5469.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |