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WO2010058409A2 - Purification optique d'esoméprazole - Google Patents

Purification optique d'esoméprazole Download PDF

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Publication number
WO2010058409A2
WO2010058409A2 PCT/IN2008/000775 IN2008000775W WO2010058409A2 WO 2010058409 A2 WO2010058409 A2 WO 2010058409A2 IN 2008000775 W IN2008000775 W IN 2008000775W WO 2010058409 A2 WO2010058409 A2 WO 2010058409A2
Authority
WO
WIPO (PCT)
Prior art keywords
esomeprazole
methoxy
omeprazole
benzimidazole
sodium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2008/000775
Other languages
English (en)
Other versions
WO2010058409A3 (fr
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hetero Research Foundation
Original Assignee
Hetero Research Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hetero Research Foundation filed Critical Hetero Research Foundation
Priority to US12/742,531 priority Critical patent/US8354541B2/en
Priority to EP08878233A priority patent/EP2346854A4/fr
Priority to PCT/IN2008/000775 priority patent/WO2010058409A2/fr
Publication of WO2010058409A2 publication Critical patent/WO2010058409A2/fr
Anticipated expiration legal-status Critical
Publication of WO2010058409A3 publication Critical patent/WO2010058409A3/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to process for optical purification of esomeprazole or a salt thereof.
  • Omeprazole chemically 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2- pyridinyl)methyl]sulfinyl]-1 H-benzimidazole and its therapeutic uses were disclosed in European Patent No. 5129.
  • Omeprazole is a well-known gastric acid secretion inhibitor, and is useful as an anti ulcer agent.
  • Omeprazole has a stereogenic center at sulfur and therefore exist as two optical isomers such as R-omeprazole and S-omeprazole (esomeprazole).
  • WO97/02261 disclosed a process for the optical purification of certain enantiomerically enriched benzimidazole derivatives by using a crystallization method.
  • Chinese Patent No. 1087739 disclosed a method of preparing esomeprazole by using (S)-(-)-binol ( ⁇ -binapthol) as an optical resolution agent by inclusion of complex with (S)-(-)-binol
  • Chinese Patent No. 1223262 was related to a process for the preparation of certain optically pure benzimidazole derivatives by inclusion complexation with binaphthyl phenol derivative.
  • Enantioselective synthesis was described for example in Euro. J. Biochem. 166 (1987) 453 and US 5,948,789. Disadvantages of these methods are that strict control of conditions is to be maintained and strict control of quantities of oxidizing agents is required for avoiding oxidation of desired sulfoxide to sulfone impurity. Moreover, these methods require expensive reagents like titanium isoproxide and diethyl-D-tartarate.
  • racemic benzimidazole sulfoxides such as omeprazole, useful as starting materials for preparing enantiomerically pure benzimidazole sulfoxides, from their corresponding sulfides involves a problem of over oxidation to form sulfone impurities.
  • WO2005/105786 and WO2005/116011 described the resolution methods for racemic benzimidazole sulfoxides.
  • WO2006/094904 disclosed a process for the resolution of 2-(2- pyridimylmethylsulfinyl)-benzimidazole derivatives by the inclusion complex with [1 ,1'-binapthalene]-2-2'-diol in presence of amine.
  • WO2007/013743 disclosed an improved optical resolution process for preparing optically pure esomeprazole and its salts by inclusion complex with (S)-(-)-binol.
  • WO2007/074099 disclosed process for the preparation of optiacally pure benzimidazole derivatives by inclusion complex with (S)-1 ,1 ,2-triphenyl-1 ,2- ethanediol.
  • WO2008/092939 disclosed a process for the preparation of substantially optically pure omeprazole with the formation of a complex by using chiral amine or chiral quaternary ammonium salt.
  • a process for optical purification of esomeprazole or a salt thereof comprises: a. preparing a solution of esomeprazole sodium having 20 to 1% R- omeprazole by weight of the sum of the contents of esomeprazole and R-omeprazole in a solvent selected from an alcohol or a mixture of alcohols; b. precipitating esomeprazole sodium; and c.
  • Substantially pure esomeprazole sodium obtained by the process of the present invention may optically be converted to esomeprazole free compound or any other salt of esomeprazole in substantially pure form.
  • the solution of esomeprazole sodium may be prepared (step-a) by the methods known such as by dissolving esomeprazole sodium in the solvent or by adding a source of sodium such as sodium hydroxide to a solution of esomeprazole in the solvent.
  • the precipitation of esomeprazole sodium in (step-b) may be carried out by the techniques known to the art such as aging, stirring, cooling, seeding, partial evaporation of the solvent etc.
  • the esomeprazole is selectively precipitated leaving R-omeprazole in the solution.
  • the precipitated solid may be collected by, for example, filtration or centrifugation.
  • the solvent used in the process may preferably selected from methanol, ethanol and isopropyl alcohol, and more preferable being methanol.
  • the esomeprazole sodium used in step (a) may preferably have 20 to 3%, more preferably 15 to 5% of R-omeprazole by weight of the sum of the contents of esomeprazole and R-omeprazole.
  • Substantially pure esomeprazole sodium refers to esomeprazole sodium having higher chiral purity than the esomeprazole sodium used in step (a) of the present invention.
  • the process can yield esomeprazole sodium having chiral purity higher than 99%.
  • the process of the invention can be repeated until the desired chiral purity of esomeprazole sodium is obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention concerne un procédé de purification d’esoméprazole ou d’un sel d’ésoméprazole. De l’ésoméprazole sodium renfermant en poids de 20 à 1% de R-oméprazole de la somme des contenus d’oméprazole et de R-oméprazole est précipité à partir d’un solvant pris dans un alcool ou un mélange d’alcools, le solide précipité étant recueilli en vue de l’obtention d’ésoméprazole
PCT/IN2008/000775 2008-11-18 2008-11-18 Purification optique d'esoméprazole Ceased WO2010058409A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US12/742,531 US8354541B2 (en) 2008-11-18 2008-11-18 Optical purification of esomeprazole
EP08878233A EP2346854A4 (fr) 2008-11-18 2008-11-18 Purification optique d esoméprazole
PCT/IN2008/000775 WO2010058409A2 (fr) 2008-11-18 2008-11-18 Purification optique d'esoméprazole

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2008/000775 WO2010058409A2 (fr) 2008-11-18 2008-11-18 Purification optique d'esoméprazole

Publications (2)

Publication Number Publication Date
WO2010058409A2 true WO2010058409A2 (fr) 2010-05-27
WO2010058409A3 WO2010058409A3 (fr) 2011-10-13

Family

ID=42198600

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000775 Ceased WO2010058409A2 (fr) 2008-11-18 2008-11-18 Purification optique d'esoméprazole

Country Status (3)

Country Link
US (1) US8354541B2 (fr)
EP (1) EP2346854A4 (fr)
WO (1) WO2010058409A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013072934A1 (fr) * 2011-10-12 2013-05-23 Alkem Laboratories Ltd. Nouveau procédé de purification optique d'inhibiteurs de la pompe à protons et de sels pharmaceutiquement acceptable de ceux-ci
CN104592201A (zh) * 2015-01-13 2015-05-06 江苏中邦制药有限公司 一种奥美拉唑的精制方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112661744B (zh) * 2020-12-28 2023-01-20 北京悦康科创医药科技股份有限公司 一种艾司奥美拉唑钠的纯化方法
EP4598528A1 (fr) 2022-10-04 2025-08-13 Arsenil Zabirnyk Inhibition de calcification de valve aortique

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8301182D0 (sv) * 1983-03-04 1983-03-04 Haessle Ab Novel compounds
DE4035455A1 (de) * 1990-11-08 1992-05-14 Byk Gulden Lomberg Chem Fab Enantiomerentrennung
US5877192A (en) * 1993-05-28 1999-03-02 Astra Aktiebolag Method for the treatment of gastric acid-related diseases and production of medication using (-) enantiomer of omeprazole
SE9301830D0 (sv) 1993-05-28 1993-05-28 Ab Astra New compounds
CN1087739A (zh) 1993-11-26 1994-06-08 陆基 能可靠发现失效的离子感烟探测器
HRP960232A2 (en) 1995-07-03 1998-02-28 Astra Ab A process for the optical purification of compounds
CN1087739C (zh) 1998-12-28 2002-07-17 中国科学院成都有机化学研究所 光学纯的苯并咪唑类抗消化性溃疡药物的包结拆分制备法
WO2004002982A2 (fr) 2002-06-27 2004-01-08 Dr. Reddy's Laboratories Limited Procede de preparation de composes sulfoxyde optiquement purs ou optiquement enrichis, notamment de l'esomeprazole amorphe et ses sels
DE602004022337D1 (de) 2004-04-28 2009-09-10 Hetero Drugs Ltd Verfahren zur herstellung von pyridinylmethyl-1h-benzimidazolverbindungen in enantiomerenangereicherter form oder als einzelne enantiomere
EP1748998B1 (fr) 2004-05-28 2010-01-27 Hetero Drugs Limited Nouveau procede de synthese stereoselective de sulfoxydes de benzimidazole
ES2259269B1 (es) 2005-03-03 2007-11-01 Esteve Quimica, S.A. Procedimiento para la preparacion de derivados de 2-(2-piridilmetilsulfinil)-bencimidazol opticamente activos.
KR100641534B1 (ko) 2005-07-28 2006-11-01 한미약품 주식회사 에스오메프라졸 및 그의 염의 제조방법
CA2631459A1 (fr) 2005-12-28 2007-07-05 Union Quimico Farmaceutica, S.A. Procede pour la preparation de l'enantiomere (s) d'omeprazole
US8063074B2 (en) * 2006-05-04 2011-11-22 Dr. Reddy's Laboratories Limited Polymorphic forms of esomeprazole sodium
WO2008092939A2 (fr) 2007-01-31 2008-08-07 Krka, Tovarna Zdravil, D.D., Novo Mesto Procédé de préparation d'oméprazole optiquement pur
EP2143722A1 (fr) * 2008-07-09 2010-01-13 Lek Pharmaceuticals D.D. Procédé de préparation de sodium ésoméprazole de haute pureté chimique et nouvelles formes de sodium ésoméprazole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2346854A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013072934A1 (fr) * 2011-10-12 2013-05-23 Alkem Laboratories Ltd. Nouveau procédé de purification optique d'inhibiteurs de la pompe à protons et de sels pharmaceutiquement acceptable de ceux-ci
CN104592201A (zh) * 2015-01-13 2015-05-06 江苏中邦制药有限公司 一种奥美拉唑的精制方法

Also Published As

Publication number Publication date
EP2346854A2 (fr) 2011-07-27
EP2346854A4 (fr) 2012-10-17
US20110213155A1 (en) 2011-09-01
US8354541B2 (en) 2013-01-15
WO2010058409A3 (fr) 2011-10-13

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