WO2010004571A2 - Procédé de purification du sodium de rabéprazole - Google Patents

Procédé de purification du sodium de rabéprazole Download PDF

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Publication number
WO2010004571A2
WO2010004571A2 PCT/IN2008/000433 IN2008000433W WO2010004571A2 WO 2010004571 A2 WO2010004571 A2 WO 2010004571A2 IN 2008000433 W IN2008000433 W IN 2008000433W WO 2010004571 A2 WO2010004571 A2 WO 2010004571A2
Authority
WO
WIPO (PCT)
Prior art keywords
rabeprazole
sodium
stirred
added
rabeprazole sodium
Prior art date
Application number
PCT/IN2008/000433
Other languages
English (en)
Other versions
WO2010004571A3 (fr
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Jonnala Sambi Reddy
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 PCT/IN2008/000433 priority Critical patent/WO2010004571A2/fr
Priority to EP08808137A priority patent/EP2294064A4/fr
Publication of WO2010004571A2 publication Critical patent/WO2010004571A2/fr
Publication of WO2010004571A3 publication Critical patent/WO2010004571A3/fr

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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 a process for obtaining pure rabeprazole sodium.
  • Xhe present invention also relates to a novel process for the preparation rabeprazole sodium amorphous form, and to a pharmaceutical composition comprising it.
  • Rabeprazole sodium is an inhibitor of the gastric proton pump. It suppress gastric acid secretion by inhibiting the gastric H + , K + ATPase at the secretory surface of the gastric parital cell and blocks the final step of gastric acid secretion.
  • Rabeprazole sodium is a sulfoxide compound have been prepared by oxidizing thioether compound with an oxidizing agent such as hydrogen peroxide, m-chloroperbenzoic acid, sodium hypochlorite, sodium hypobromite etc., as described in JP-A1-6270 (EP 268956), US 5045552). Rabeprazole represented by following structure:
  • Japanese patent application JP2001039975 indicates that the product obtained by example 33 of U.S. patent No. 5045552 with a melting point of 140- 141 0 C corresponds to amorphous rabeprazole sodium.
  • the X- ray powder diffraction pattern of the amorphous rabeprazole sodium is shown.
  • U.S. patent No. 6180652 concerns process for the purification of rabeprazole and its pharmaceutically acceptable salts for its sulfone impurity, via: acetone complex of the rabeprazole or its pharmaceutically acceptable salts.
  • rabeprazole sodium in amorphous form is obtained by lyophilizing an aqueous solution of rabeprazole sodium acetone complex.
  • lyophilization is a technique which is not suitable for production at industrial scale because this process presents serious limitations on cost, time, equipment capability and environmental protection.
  • WO 2004/085424 A1 refers to the conversion of the rabeprazole sodium acetone complex into amorphous rabeprazole sodium by heating at elevated temperatures, preferably between 100 and 110 0 C. It is well known that exposing rabeprazole-type compounds to high temperatures increases the risk of decomposition to form impurities and as such, heat treatment of rabeprazole sodium acetone complex into amorphous rabeprazole sodium is not adequate for the production of a rabeprazole which is suitable for pharmaceutical use.
  • a process for preparing amorphous rabeprazole sodium comprises: a) Mixing a solution of rabeprazole sodium in a chlorinated solvent with cyclohexane, b) stirring the contents obtained in step (a) at 0-50 0 C for at least 15 minutes, and c) isolating amorphous rabeprazole sodium from the contents obtained in step (b).
  • the solution of rabeprazole sodium in the chlorinated solvent may be obtained for example, by dissolving rabeprazole sodium in the chlorinated solvent or as a part of reaction mass obtained by reaction of rabeprazole with a base such as sodium hydroxide.
  • the chlorinated solvent used in step (a) may preferably be methylene chloride, ethylene chloride or chloroform; or a mixture thereof.
  • the more preferred chlorinated solvent is methylene chloride.
  • the stirring in step (b) may preferably carried out at 20-35 0 C for 15 to 75 minutes, more preferably at 15 to
  • Preparation of the amorphous rabeprazole sodium may occur during step (b).
  • the precipitated solid may be isolated from the contents by methods such as filtration or ce ⁇ trifugation. If required the isolation of the amorphous rabeprazole sodium may be performed by the methods known in the art such as by cooling, using an antisolvent, by partial evaporation or a combination thereof followed by filtration or a centrifugation.
  • the bottom organic layer was separated twice by treating with methylene chloride (2 x 250 L), stirred and allowed to settle for 15 minutes.
  • Water (1300 L) and sodium hydroxide flakes (50 Kg) were added to the reactor, cooled to 20 - 25 0 C and then added the methylene chloride layer to the reactor.
  • Sodium chloride (50 Kg) was added to the reaction mixture, stirred for 20 minutes and allowed to settle for 20 minutes.
  • the bottom organic layer was separated.
  • the pH of the aqueous layer was adjusted to 9.2 - 9.4 with ammonium acetate solution (ammonium acetate: 52 Kg + water: 200 L) and acetic acid solution (acetic acid: 65 L + water: 200 L).
  • the bottom organic layer was separated twice by treating with methylene chloride (2 x 650 L), stirred and allowed to settle for 15 minutes.
  • the organic layer was given carbon treatment, filtered and washed the filtrate with methylene chloride (50 L). Dried the total organic layers with sodium sulfate (20 Kg) and 2-Amino ethanol (1.8 L) was added. The organic layer was concentrated until the mass temperature reached to 40 - 45 0 C.
  • Acetonitrile (50 L) was added to the reaction mass and acetonitrile was distilled off from the reaction mass until the mass temperature reached to 40 - 45 0 C.
  • Acetonitrile (600 L) was added to the reaction mass, stirred for 2 hours at room temperature and cooled to 0 - 5 0 C.
  • the total organic layer was washed with sodiumchloride solution (sodium chloride: 36 Kg, DM water: 140 L), given carbon treatment, filtered, washed the filtrate with methylenechloride (50 L) and 2-amino ethanol (0.54 L) was added.
  • the organic layer was concentrated until the mass temperature reached to 35 - 40 0 C.
  • Acetonitrile (90 L) was added to the reaction mass and acetonitrile was distilled off from the reaction mass until the mass temperature reached to 35 - 40 0 C.
  • Acetonitrile (270 L) was added to the reaction mass, cooled to 25 - 35 0 C, stirred for 1 hour 30 minutes, cooled to 0 - 5 0 C and stirred for 1 hour.
  • Rabeprazole was added to the solution and stirred at 25 - 35 0 C for 1 hour. Methanol was distilled off from the reaction mass, dichloromethane (150 L) was added to the residual mass and the contents were stirred to obtain solution. The solution was added to cyclohexane (1080 L). The contents were stirred at 25 - 35 0 C for 30 minutes, centrifuged the material and washed at 60 - 65 0 C to obtain 69 Kg of amorphous rabeprazole sodium.

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 préparation de sodium de rabéprazole amorphe. De l’hydroxyde de sodium est dissous dans du méthanol. Le rabéprazole est ajouté à la solution et agité à une température de 25 - 35 °C pendant 1 heure. Le méthanol est éliminé par distillation de la masse réactionnelle, le dichlorométhane est ajouté à la masse résiduelle et le contenu agité pour obtenir une solution. La solution est ajoutée à du cyclohexane. Le contenu est agité à 25 - 35 °C pendant 30 minutes, centrifugé et lavé à 60 - 65°C pour obtenir du sodium de rabéprazole amorphe.
PCT/IN2008/000433 2008-07-07 2008-07-07 Procédé de purification du sodium de rabéprazole WO2010004571A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2008/000433 WO2010004571A2 (fr) 2008-07-07 2008-07-07 Procédé de purification du sodium de rabéprazole
EP08808137A EP2294064A4 (fr) 2008-07-07 2008-07-07 Procédé de purification du sodium de rabéprazole

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2008/000433 WO2010004571A2 (fr) 2008-07-07 2008-07-07 Procédé de purification du sodium de rabéprazole

Publications (2)

Publication Number Publication Date
WO2010004571A2 true WO2010004571A2 (fr) 2010-01-14
WO2010004571A3 WO2010004571A3 (fr) 2010-12-29

Family

ID=41507511

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000433 WO2010004571A2 (fr) 2008-07-07 2008-07-07 Procédé de purification du sodium de rabéprazole

Country Status (2)

Country Link
EP (1) EP2294064A4 (fr)
WO (1) WO2010004571A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2391197A1 (es) * 2011-04-27 2012-11-22 Moehs Ibérica S.L. Procedimiento de obtención de rabeprazol sódico amorfo.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA06000410A (es) * 2003-07-15 2006-03-17 Allergan Inc Procedimiento para preparar profarmacos isomericamente puros de inhibidores de la bomba de protones.
WO2006024890A1 (fr) * 2004-08-30 2006-03-09 Apollo International Limited Procede ameliore de preparation de rabeprazole sodique sous forme amorphe
JP2008534578A (ja) * 2005-03-30 2008-08-28 ルピン・リミテッド ラベプラゾールナトリウムの改良された製法
AR058440A1 (es) * 2005-08-02 2008-02-06 Medichem Sa Procesos para la produccion de rabeprazol sodico amorfo
EP2162449A4 (fr) * 2007-05-25 2011-07-13 Hetero Drugs Ltd Procédé amélioré de preparation de rabéprazole sodique amorphe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2294064A4 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2391197A1 (es) * 2011-04-27 2012-11-22 Moehs Ibérica S.L. Procedimiento de obtención de rabeprazol sódico amorfo.

Also Published As

Publication number Publication date
EP2294064A2 (fr) 2011-03-16
EP2294064A4 (fr) 2011-10-05
WO2010004571A3 (fr) 2010-12-29

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