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WO2005014546A1 - Nouvelles formes cristallines de celecoxib - Google Patents

Nouvelles formes cristallines de celecoxib Download PDF

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Publication number
WO2005014546A1
WO2005014546A1 PCT/IN2003/000267 IN0300267W WO2005014546A1 WO 2005014546 A1 WO2005014546 A1 WO 2005014546A1 IN 0300267 W IN0300267 W IN 0300267W WO 2005014546 A1 WO2005014546 A1 WO 2005014546A1
Authority
WO
WIPO (PCT)
Prior art keywords
celecoxib
solvate
dma
dmf
process according
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/IN2003/000267
Other languages
English (en)
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Kesireddy Subash Chander 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 Drugs Ltd
Original Assignee
Hetero Drugs 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 Hetero Drugs Ltd filed Critical Hetero Drugs Ltd
Priority to PCT/IN2003/000267 priority Critical patent/WO2005014546A1/fr
Priority to AU2003264861A priority patent/AU2003264861A1/en
Publication of WO2005014546A1 publication Critical patent/WO2005014546A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • the present invention relates to novel crystalline forms of celecoxib and to processes for their preparation.
  • Celecoxib is a selective cyclooxygenase-2 inhibitor and useful in the treatment of specific cyclooxygenase-2 mediated disorders.
  • Celecoxib is chemically designated as 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1 H-pyrazol-1- yljbenzenesulfonamide.
  • Celecoxib is currently used in the treatment of arthritis and pain.
  • Celecoxib is represented by the following structure:
  • Celecoxib and related compounds, processes for their preparation and their therapeutic uses were disclosed in US 5,466,823.
  • EP 1167355 disclosed two non-solvated crystalline forms of celecoxib, Form I and Form II and processes for preparation thereof.
  • WO 0141536 disclosed an amorphous celecoxib.
  • WO 0042021 disclosed N,N-dimethylformamide and N,N- dimethylacetamide solvates of celecoxib and the process described in the publication produces mono N,N-dimethylformamide solvate(N,N- dimethylformamide content is about 16.1%) and mono N,N-dimethylacetamide solvate(N,N-dimethylacetamide content is about 18.5%) of celecoxib.
  • celecoxib DMF solvate having N,N-dimethylformamide content of about 4 to 12% of the weight of the celecoxib DMF solvate and celecoxib DMA solvate having N,N-dimethylacetamide content of about 2 to 8% of the weight of the celecoxib DMA solvate.
  • the celecoxib solvates are obtainable in very pure form and have good storage stability even under high humidity and in a broad temperature range.
  • celecoxib DMF solvate and celecoxib DMA solvate are useful as intermediates for preparing pure celecoxib or celecoxib in any other polymorph.
  • the object of the present invention is to provide celecoxib DMF solvate and celecoxib DMA solvate and process for preparing the solvates; and use of these solvates to prepare other forms of celecoxib.
  • DETAILED DESCRIPTION OF THE INVENTION there is provided celecoxib N,N-dimethylformamide solvate(celecoxib DMF solvate), wherein the content of N,N-dimethylformamide is between about 4 to 12% of the weight of celecoxib DMF solvate.
  • Celecoxib DMF solvate typically shows a crystalline form, which is designated as celecoxib DMF solvate form H1 and typical form H1 x-ray powder diffraction spectrum of celecoxib DMF solvate form H1 is shown in figure 1.
  • Celecoxib DMF solvate form. H1 is characterized by peaks in the powder x-ray diffraction spectrum having two-theta angle positions at about 8.5, 13.2, 15.5, 15.8, 16.2, 16.9, 19.2, 19.7, 20.1 , 21. 9, 22.5, 23.4, 24.7, 25.4 and 26.4 degrees.
  • Celecoxib DMF solvate form H1 is prepared by dissolving celecoxib in N,N-dimethylformamide and then rapid precipitation of celecoxib DMF solvate form H1 from the solution.
  • Anti-solvent such as water may be used to precipitate celecoxib DMF solvate form H1.
  • the precipitated DMF form H1 crystals are collected by filtration or centrifugation.
  • celecoxib is dissolved at ambient temperature, water is added to the solution, the contents are stirred for 30 minutes to 4 hours and the separated crystals are collected by filtration or centrifugation to obtain pure celecoxib DMF solvate.
  • Celecoxib DMF solvate can be used to prepare celecoxib forms.
  • Celecoxib DMA solvate typically shows a crystalline form, which is designated as celecoxib DMA solvate form H2 and typical form H2 x-ray powder diffraction spectrum of celecoxib DMA solvate form H2 is shown in figure 2.
  • Celecoxib DMA solvate form H2 is characterized by peaks in the powder x-ray diffraction spectrum having two-theta angle positions at about 8.7, 13.0, 15.8, 16.2, 16.6, 17.3, 18.2, 19.2, 19.5, 19.8, 20.4, 21.3, 22.7, 23.3, 23.7, 25.3, 26.0, 28.8 and 30.4 degrees.
  • a process is provided for preparation of pure celecoxib DMA solvate form H2.
  • Celecoxib DMA solvate form H2 is prepared by dissolving celecoxib in N,N-dimethylacetamide and then rapid precipitation of celecoxib DMA solvate form H2 from the solution.
  • Anti-solvent such as water may be used to precipitate celecoxib DMA solvate form H2.
  • the precipitated DMA form H2 crystals are collected by filtration or centrifugation.
  • celecoxib is dissolved at ambient temperature, water is added to the solution, the contents are stirred for 30 minutes to 4 hours and the separated crystals are collected by filtration or centrifugation to obtain pure celecoxib DMA solvate.
  • Celecoxib DMA solvate can be used to prepare celecoxib forms.
  • Celecoxib in anhydrous form or any other solvated form may be used to prepare celecoxib DMA solvate form H2.
  • a process is provided for preparation of pure celecoxib.
  • Celecoxib is prepared by dissolving celecoxib DMA solvate in isopropanol and isolating celecoxib from the solution by adding water.
  • Pure celecoxib or pure celecoxib solvate refers to at least 94% and preferably at least 99% of chromatographic purity.
  • Celecoxib in any crystalline form obtained by previously known methods may be used in the above processes.
  • Example 4 Celecoxib DMA solvate (10 gm, purity: 99.4%) is mixed with isopropyl alcohol (75 ml), heated to about 50°C and stirred for 1 hour at the same temperature. Then water (100 ml) is added, stirred for 2 hours at ambient temperature. Then filtered the solid and dried at about 50°C to give 7.2 gm of celecoxib(purity : 99.5%).
  • Example 5 Example 1 is repeated using celecoxib form I instead of celecoxib. The yield of celecoxib solvate DMF form H1 is 4.5 gm.
  • Example 6 Example 2 is repeated using celecoxib form II instead of celecoxib. The yield of celecoxib DMA solvate form H2 is 9.4 gm.

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

Abstract

L'invention se rapporte à de nouvelles formes cristallines de celecoxib, à leurs procédés de préparation et à des procédés de purification de celecoxib.
PCT/IN2003/000267 2003-08-08 2003-08-08 Nouvelles formes cristallines de celecoxib Ceased WO2005014546A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000267 WO2005014546A1 (fr) 2003-08-08 2003-08-08 Nouvelles formes cristallines de celecoxib
AU2003264861A AU2003264861A1 (en) 2003-08-08 2003-08-08 Novel crystalline forms of celecoxib

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000267 WO2005014546A1 (fr) 2003-08-08 2003-08-08 Nouvelles formes cristallines de celecoxib

Publications (1)

Publication Number Publication Date
WO2005014546A1 true WO2005014546A1 (fr) 2005-02-17

Family

ID=34131130

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000267 Ceased WO2005014546A1 (fr) 2003-08-08 2003-08-08 Nouvelles formes cristallines de celecoxib

Country Status (2)

Country Link
AU (1) AU2003264861A1 (fr)
WO (1) WO2005014546A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006079923A3 (fr) * 2005-01-31 2006-12-07 Pharmacia & Upjohn Co Llc Forme cristalline iv du celecoxib
WO2011055233A2 (fr) 2009-11-03 2011-05-12 Actavis Group Ptc Ehf Procédé amélioré pour préparer un polymorphe de célécoxib

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042021A1 (fr) * 1999-01-14 2000-07-20 Merck Frosst Canada & Co. Synthese de 4-[(phenyl substitue en position 5 ou non substitue)-1h-pyrazol-1-yl substitue en position 3]benzene-sulfonamides
WO2001042222A1 (fr) * 1999-12-08 2001-06-14 Pharmacia Corporation Formes polymorphes cristallines du celecoxibe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042021A1 (fr) * 1999-01-14 2000-07-20 Merck Frosst Canada & Co. Synthese de 4-[(phenyl substitue en position 5 ou non substitue)-1h-pyrazol-1-yl substitue en position 3]benzene-sulfonamides
WO2001042222A1 (fr) * 1999-12-08 2001-06-14 Pharmacia Corporation Formes polymorphes cristallines du celecoxibe

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006079923A3 (fr) * 2005-01-31 2006-12-07 Pharmacia & Upjohn Co Llc Forme cristalline iv du celecoxib
WO2011055233A2 (fr) 2009-11-03 2011-05-12 Actavis Group Ptc Ehf Procédé amélioré pour préparer un polymorphe de célécoxib

Also Published As

Publication number Publication date
AU2003264861A1 (en) 2005-02-25

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