WO2007108009A1 - Procede de purification du topiramate - Google Patents

Procede de purification du topiramate Download PDF

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Publication number
WO2007108009A1
WO2007108009A1 PCT/IN2007/000107 IN2007000107W WO2007108009A1 WO 2007108009 A1 WO2007108009 A1 WO 2007108009A1 IN 2007000107 W IN2007000107 W IN 2007000107W WO 2007108009 A1 WO2007108009 A1 WO 2007108009A1
Authority
WO
WIPO (PCT)
Prior art keywords
topiramate
purification
purity
water
solution
Prior art date
Application number
PCT/IN2007/000107
Other languages
English (en)
Inventor
Pandurang Balwant Deshpande
Parven Kumar Luthra
Anand Kumar Pandey
Bhavin Prafulbhai Hamirani
Original Assignee
Alembic Limited
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 Limited filed Critical Alembic Limited
Publication of WO2007108009A1 publication Critical patent/WO2007108009A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals

Definitions

  • the present invention relates to a process for purification of Topiramate of formula (I).
  • Topiramate is chemically known as 2, 3:4, 5-Bis-O-(1-methylethylidene)-1-O- sulfamoyl-beta-D-fructopyranose or 2, 3:4, 5-Bis-O-(1-methylethylidene)- beta-D- fructopyranose sulfamate, having molecular formula C1 2 H21NO8S and molecular weight 339.36.
  • the current pharmaceutical product containing this drug is being sold by Ortho McNeil using the tradename Topamax ® in the form of tablets.
  • Topiramate is sulfamate-substituted monosaccharide derivative which are useful in the treatment of epilepsy, obesity, bipolar disorder, neuropathic pain, migraine and smoking cessation.
  • Topiramate acts as a carbonate dehydratase inhibitor, sodium channel blocker, AMPA antagonist, GABA agonist and glutamate antagonist.
  • Topiramate is first disclosed in US Patent No. 4,513,006 which also discusses its process for preparation. The final product is recrystallized from a mixture of ethyl acetate and hexane. However this process for purification remains silent about purity and yield of Topiramate.
  • US Patent No. 5,387,700 which discloses the recrystallization of Topiramate by using ethanol: water mixture as solvent which requires base treatment. This patent also discloses crystallization by using n-hexane which does not give Topiramate with high purity and yield.
  • Topiramate Form I obtained by present invention is characterized by its XRD pattern as shown in Fig.1.
  • Fig. 1 represnts the powder X-ray diffraction (XRD) pattern of Topiramate Form I.
  • Another object of the present invention is to provide a process for the purification of Topiramate which is operationally simple, easy to handle and applicable at an industrial scale.
  • Yet another object of the present invention is to provide process for purification of ; Topiramate which comprises purification of Topiramate by treating Topiramate base with mixture of acetone and water.
  • present invention relates to a process for the purification of Topiramate comprising a step of treating Topiramate base with a mixture of acetone and water.
  • Crude Topiramate as used hereinabove is meant to include Topiramate is any form, or hydrate, solvate or their mixtures, or any state of purity.
  • treating refers to suspending, dissolving, washing, mixing, crystallizing or recrystallizing Topiramate in any of the solvent described above.
  • Topiramate Form I as prepared according to aspect of present invention is characterized by powder X-ray diffraction peaks at about 9.2, 12.1, 13.0, 15.3, 16.1 , 17.2, 19.9, 20.7, 21.1 , 24.5, 25.8, 29.3 and 32.8 ⁇ 0.2 degree two-theta.
  • Topiramate is dissolved in acetone at about 20 0 C to 35 0 C under stirring to obtain a solution. Water is added to said solution drop wise under stirring. The slurry was cooled to about 0 0 C to about 15°C and stirred for about 1 hour to about 4 hours. It is filtered, washed with water and dried to obtain pure crystalline form of Topiramate.
  • crude Topiramate is dissolved in acetone at about 20 0 C to 35 0 C under stirring to obtain a solution.
  • the said solution is added to chilled water in one lot.
  • the slurry is stirred for about 1 hour to about 4 hours at about chilled temperature to ambient temperature. It is filtered, washed with water and dried to obtain pure Topiramate Form.
  • purification refers to any method known to a person skilled in the art such as purification from single solvent or combination of solvents by dissolving the compound optionally at elevated temperature and precipitating the compound by cooling the solution or removing solvent from the solution or both. It further includes methods such as solvent/antisolvent or precipitation.
  • Topiramate Form I is isolated from reaction mass by conventional isolation procedure such as filtration, centrifugation, washing the wet cake and drying or by evaporation of solvent.
  • Topiramate (10g) was dissolved in acetone (20ml) at about 20 0 C to 35 0 C under stirring to obtain a solution. The said solution was added to chilled water (40 ml) in one lot.Topiramate was started to crystallize out. The slurry was stirred for 2 hour at about chilled temperature to ambient temperature. It was filtered, washed with water and dried to obtain pure form of Topiramate (8.4gm), purity of at least 99.5% (HPLC).

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Saccharide Compounds (AREA)
  • Hematology (AREA)

Abstract

La présente invention concerne un nouveau procédé de préparation de la forme I du topiramate, lequel procédé comprenant la purification du topiramate brut sur la base du traitement de ce-dernier avec un mélange d'acétone et d'eau pour donner le topiramate d'une pureté d'au moins 99,5 %.
PCT/IN2007/000107 2006-03-17 2007-03-15 Procede de purification du topiramate WO2007108009A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN371/MUM/2006 2006-03-17
IN371MU2006 2006-03-17

Publications (1)

Publication Number Publication Date
WO2007108009A1 true WO2007108009A1 (fr) 2007-09-27

Family

ID=38325553

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000107 WO2007108009A1 (fr) 2006-03-17 2007-03-15 Procede de purification du topiramate

Country Status (1)

Country Link
WO (1) WO2007108009A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8652527B1 (en) 2013-03-13 2014-02-18 Upsher-Smith Laboratories, Inc Extended-release topiramate capsules
US9101545B2 (en) 2013-03-15 2015-08-11 Upsher-Smith Laboratories, Inc. Extended-release topiramate capsules

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5387700A (en) * 1991-09-19 1995-02-07 Mcneilab, Inc. Process for the preparation of chlorosulfate and sulfamate derivatives of 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose and (1-methylcyclohexyl)methanol
WO2004108732A1 (fr) * 2003-05-12 2004-12-16 Sun Pharmaceutical Industries Limited PROCEDE DE PREPARATION DE SULFAMATE2,3:4,5-BIS-O(1-METHYLETHYLIDENE)-ss-D-FRUCTOPYRANOSE
EP1627881A1 (fr) * 2004-08-19 2006-02-22 Helm AG Procédé de préparation de topiramate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5387700A (en) * 1991-09-19 1995-02-07 Mcneilab, Inc. Process for the preparation of chlorosulfate and sulfamate derivatives of 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose and (1-methylcyclohexyl)methanol
WO2004108732A1 (fr) * 2003-05-12 2004-12-16 Sun Pharmaceutical Industries Limited PROCEDE DE PREPARATION DE SULFAMATE2,3:4,5-BIS-O(1-METHYLETHYLIDENE)-ss-D-FRUCTOPYRANOSE
EP1627881A1 (fr) * 2004-08-19 2006-02-22 Helm AG Procédé de préparation de topiramate

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8652527B1 (en) 2013-03-13 2014-02-18 Upsher-Smith Laboratories, Inc Extended-release topiramate capsules
US8889190B2 (en) 2013-03-13 2014-11-18 Upsher-Smith Laboratories, Inc. Extended-release topiramate capsules
US10363224B2 (en) 2013-03-13 2019-07-30 Upsher-Smith Laboratories, Llc Extended-release topiramate capsules
US9101545B2 (en) 2013-03-15 2015-08-11 Upsher-Smith Laboratories, Inc. Extended-release topiramate capsules
US9555005B2 (en) 2013-03-15 2017-01-31 Upsher-Smith Laboratories, Inc. Extended-release topiramate capsules
US10172878B2 (en) 2013-03-15 2019-01-08 Upsher-Smith Laboratories, Llc Extended-release topiramate capsules

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