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WO2011004281A1 - Procédé pour la préparation d’une forme amorphe de rabéprazole sodium - Google Patents

Procédé pour la préparation d’une forme amorphe de rabéprazole sodium Download PDF

Info

Publication number
WO2011004281A1
WO2011004281A1 PCT/IB2010/052819 IB2010052819W WO2011004281A1 WO 2011004281 A1 WO2011004281 A1 WO 2011004281A1 IB 2010052819 W IB2010052819 W IB 2010052819W WO 2011004281 A1 WO2011004281 A1 WO 2011004281A1
Authority
WO
WIPO (PCT)
Prior art keywords
rabeprazole
amorphous form
rabeprazole sodium
sodium
preparation
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/IB2010/052819
Other languages
English (en)
Inventor
Ravi Ponnaiah
Sanjay Desai
Dhiraj Rathod
Lalit Katariya
Nilesh Bhimani
Viral Modi
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.)
Alembic Ltd
Original Assignee
Alembic Ltd
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 Alembic Ltd filed Critical Alembic Ltd
Publication of WO2011004281A1 publication Critical patent/WO2011004281A1/fr
Anticipated expiration legal-status Critical
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 a process for the preparation of amorphous form of
  • Rabeprazole belongs to class of proton pump inhibitors. It is an antiulcer agent. It is useful for the treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease. It is marketed by Eisai in USA under brand name ACHIPHX ® .
  • Rabeprazole involves dissolving Rabeprazole base in aqueous solution of sodium hydroxide. Further water was removed from azeotropically from the reaction mixture using ethanol to obtain residue. Ether was added to the residue to obtain precipitate of the product.
  • the form obtained by following the process disclosed in US patent no. 5045552 is amorphous form. The major drawback of this process is that when it is practiced on commercial scale the product obtained is sticky and not easily filterable. Moreover, azeotropic distillation is not economically viable process.
  • Rabeprazole sodium salt in distilled water for 48 hours results in amorphous form of Rabeprazole sodium.
  • WO 03101452 discloses process for preparation of amorphous form of Rabeprazole sodium which involves dissolution of Rabeprazole base in aqueous sodium hydroxide and lyophilizing the solution. Lyophilization technique involves large production capital. Therefore, these processes are also not commercially useful.
  • the inventors of present invention have directed their efforts towards developing a process for the preparation of Rabeprazole sodium which is operationally simple, easily scalable and economically viable.
  • Another object of the present invention is to provide a process for the preparation of amorphous form of Rabeprazole sodium which is operationally simple, easily scalable and economically viable.
  • An aspect of the present invention provides a process for the preparation of
  • step (h) adding solution obtained in step (f) to methyl-tert. butyl ether to obtain
  • the present invention provides a process for the preparation of amorphous form of
  • Rabeprazole sodium of formula (I) comprising,
  • Rabeprazole base used in the process of present invention can be prepared by any method known in the art.
  • pellets in methanol is prepared.
  • the volume of methanol is in range of two times to five times the weight of Rabeprazole sodium, preferably four times.
  • Sodium hydroxide is in range of 0.9 molar equivalent to 1.5 molar equivalents, preferably 1 mole equivalent.
  • Rabeprazole base is added to solution of sodium hydroxide in methanol at temperature of about 2O 0 C to 3O 0 C.
  • the reaction mixture can be optionally charcoalized and filtered.
  • toluene in amount of 1 to 5 ml per gram of Rabeprazole base used, preferably 1 ml per gram and ethyl acetate in amount of 0.5 to 1.5 ml per gram of Rabeprazole base used, preferably 0.5 ml per gram to obtain a clear solution.
  • the amorphous form of Rabeprazole obtained by process of present invention can be isolated by conventional methods known to person skilled in the art like filtration, cen- trifugation and the like.
  • D 90 of Rabeprazole sodium obtained by the process of present invention has particle size in range of lOO ⁇ m to 200 ⁇ m.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un procédé pour la préparation d’une forme amorphe de Rabéprazole sodium de formule (I).
PCT/IB2010/052819 2009-07-09 2010-06-22 Procédé pour la préparation d’une forme amorphe de rabéprazole sodium Ceased WO2011004281A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1624/MUM/2009 2009-07-09
IN1624MU2009 2009-07-09

Publications (1)

Publication Number Publication Date
WO2011004281A1 true WO2011004281A1 (fr) 2011-01-13

Family

ID=42778125

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/052819 Ceased WO2011004281A1 (fr) 2009-07-09 2010-06-22 Procédé pour la préparation d’une forme amorphe de rabéprazole sodium

Country Status (1)

Country Link
WO (1) WO2011004281A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20131859A1 (it) * 2013-11-08 2015-05-09 Dipharma Francis Srl Procedimento per la preparazione di un composto benzimidazolico in forma amorfa
US20180082083A1 (en) * 2016-09-16 2018-03-22 Intel Corporation Technologies for secure boot provisioning and management of field-programmable gate array images

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5045552A (en) 1986-11-13 1991-09-03 Eisai Co., Ltd. Pyridine derivatives having anti-ulcerative activity
US6180652B1 (en) 1998-11-16 2001-01-30 Eisai Co., Ltd. Sulfoxide compounds and acetone complexes, and a process for producing the same
WO2003101452A1 (fr) 2002-06-03 2003-12-11 Aurobindo Pharma Ltd. Procede de preparation de sel de sodium a haute teneur en rabeprazole
WO2008146297A2 (fr) * 2007-05-25 2008-12-04 Hetero Drugs Limited Procédé amélioré de preparation de rabéprazole sodique amorphe
KR20090041022A (ko) * 2007-10-23 2009-04-28 일동제약주식회사 라베프라졸 나트륨염 무정형의 개선된 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5045552A (en) 1986-11-13 1991-09-03 Eisai Co., Ltd. Pyridine derivatives having anti-ulcerative activity
US6180652B1 (en) 1998-11-16 2001-01-30 Eisai Co., Ltd. Sulfoxide compounds and acetone complexes, and a process for producing the same
WO2003101452A1 (fr) 2002-06-03 2003-12-11 Aurobindo Pharma Ltd. Procede de preparation de sel de sodium a haute teneur en rabeprazole
WO2008146297A2 (fr) * 2007-05-25 2008-12-04 Hetero Drugs Limited Procédé amélioré de preparation de rabéprazole sodique amorphe
KR20090041022A (ko) * 2007-10-23 2009-04-28 일동제약주식회사 라베프라졸 나트륨염 무정형의 개선된 제조방법

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20131859A1 (it) * 2013-11-08 2015-05-09 Dipharma Francis Srl Procedimento per la preparazione di un composto benzimidazolico in forma amorfa
US20180082083A1 (en) * 2016-09-16 2018-03-22 Intel Corporation Technologies for secure boot provisioning and management of field-programmable gate array images

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