WO2005014546A1 - Novel crystalline forms of celecoxib - Google Patents
Novel crystalline forms of celecoxib Download PDFInfo
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- 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
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- WIPO (PCT)
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- celecoxib
- solvate
- dma
- dmf
- process according
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- 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.
Abstract
The present invention relates to novel crystalline forms of celecoxib, to processes for their preparation and to the methods for purification of celecoxib.
Description
NOVEL CRYSTALLINE FORMS OF CELECOXIB
FIELD OF THE INVENTION The present invention relates to novel crystalline forms of celecoxib and to processes for their preparation.
BACKGROUND OF THE INVENTION 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.
We have discovered celecoxib N,N-dimethylformamide solvate(celecoxib
DMF solvate) having N,N-dimethylformamide content of about 4 to 12% of the weight of the celecoxib DMF solvate and celecoxib N,N-dimethylacetamide solvate(celecoxib DMA solvate) having N,N-dimethylacetamide content of about 2 to 8% of the weight of the celecoxib DMA solvate. We have found that quick isolation of celecoxib from the solution of celecoxib in N,N-dimethylformamide or N,N-dimethylacetamide produces 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. So 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 In accordance with the present 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. In accordance with the present invention, there is provided a process for preparation of the pure celecoxib DMF solvate form H1. 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. Preferably, 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 in anhydrous form or any other solvated form may be used to prepare celecoxib DMF solvate form H1. . In accordance with the present invention, a process is provided for preparation of pure celecoxib. Celecoxib is prepared by dissolving celecoxib DMF solvate in isopropanol and isolating celecoxib from the solution by adding water. In accordance with the present invention, there is provided celecoxib N,N-dimethylacetamide solvate(celecoxib DMA solvate), wherein the content of N,N-dimethylacetamide is between about 2 to 8% of the weight of celecoxib DMA solvate. 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. In accordance with the present invention, 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.
Preferably, 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. In accordance with the present invention, 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.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is a x-ray powder diffraction spectrum of celecoxib DMF solvate form HL Figure 2 is a x-ray powder diffraction spectrum of celecoxib DMA solvate form H2. x-Ray powder diffraction spectrum was measured on a Bruker axs D8 advance x-ray powder diffractometer having a copper-K radiation.
The invention will now be further described by the following examples, which are illustrative rather than limiting.
Example 1 Celecoxib (5.0 gm, obtained by process described in example 1c of US
5,466,823, purity: 92%) is dissolved in N,N-dimethylformamide (25 ml) at 25°C and stirred for 10 minutes at about 25°C. Then water (15 ml) is added and stirred for 2 hours at 25°C to 30°C. The precipitated solid is filtered and dried at
about 60°C for 4 hours to give 4.0 gm of celecoxib DMF solvate form H1 (N,N- dimethylformamide content : 7.16%, Chromatographic purity : 99.4%). Example 2 Celecoxib DMF solvate (10 gm, purity : 99.3%) 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 7.5 gm of celecoxib(purity 99.4%). Example 3 Celecoxib (10 gm, obtained by process described in example 1c of US
5,466,823, purity: 91.5% ) is dissolved in N,N-dimethylacetaιmide (70 ml) at 25°C and stirred for 15 minutes at about 25°C. Then water (30 ml) is added and stirred for 3 hours at 25°C to 30°C. The precipitated solid is filtered and dried at about 60°C for 5 hours to give 9.3 gm of celecoxib DMA solvate form H2(N,N- dimethylacetamide content : 4.04%, Chromatographic purity : 99.6%). 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.
Claims
1. Celecoxib DMF solvate having N,N-dimethylformamide content of about 4 to 12% of the weight of the celecoxib DMF solvate.
2. A crystalline celecoxib DMF solvate form H1 , characterized by an x-ray powder diffraction spectrum having peaks expressed as 2Θ 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.
3. A crystalline celecoxib DMF solvate form H1 as defined in claim 2, further characterized by an x-ray powder diffraction spectrum as in figure 1.
4. A process for preparation of celecoxib DMF solvate as defined in claim 1 , which comprises the steps of: a) dissolving celecoxib in N,N-dimethylformamide; and b) rapid precipitation of celecoxib DMF solvate from the solution using an antisolvent.
5. A process according to claim 4, wherein the product obtained is celecoxib DMF solvate form H
6. A process according to claim 4, wherein celecoxib is dissolved at 20°C to 35°C, water is added to the solution, the contents are stirred for 30 minutes to 4 hours and precipitated crystals are collected by filtration or centrifugation.
7. A process according to claim 4, wherein celecoxib in anhydrous form or a solvated form is used in step (a).
8. A process for preparation of celecoxib, which comprises the steps of: a) dissolving celecoxib DMF solvate in isopropanol; and b) precipitating celecoxib from the solution.
9. A process according to claim 8, wherein water is used to precipitate celecoxib.
10. Celecoxib DMA solvate having N,N-dimethylacetamide content of about 2 to 8% of the weight of celecoxib DMA solvate.
11. A crystalline celecoxib DMA solvate form H2, characterized by an x-ray powder diffraction spectrum having peaks expressed as 20 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.
12. A crystalline celecoxib DMA solvate form H2 as defined in claim 11 , further characterized by an x-ray powder diffraction spectrum as in figure 2.
13. A process for preparation of celecoxib DMA solvate as defined in claim 0, which comprises the steps of: a) dissolving celecoxib in N,N-dimethylacetamide; and b) rapid precipitation of celecoxib DMA solvate from the solution using an anti- solvent.
14. A process according to claim 13, wherein the product obtained is celecoxib DMA solvate form H2. ,
15. A process according to claim 13, wherein celecoxib is dissolved at 20°C to 35°C, water as an anti-solvent is added to the solution, the contents are stirred for 30 minutes to 4 hours and precipitated crystals are collected by filtration or centrifugation.
16. A process according to claim 13, wherein celecoxib in anhydrous form or a solvated form is used in step (a).
17. A process for preparation of celecoxib, which comprises the steps of: a) dissolving celecoxib DMA solvate in isopropanol; and b) isolating celecoxib from the solution using an anti-solvent.
18. A process according to claim 17, wherein the anti-solvent is water.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003264861A AU2003264861A1 (en) | 2003-08-08 | 2003-08-08 | Novel crystalline forms of celecoxib |
| PCT/IN2003/000267 WO2005014546A1 (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 (en) | 2003-08-08 | 2003-08-08 | Novel crystalline forms of celecoxib |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2005014546A1 true WO2005014546A1 (en) | 2005-02-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2003/000267 WO2005014546A1 (en) | 2003-08-08 | 2003-08-08 | Novel crystalline forms of celecoxib |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003264861A1 (en) |
| WO (1) | WO2005014546A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006079923A2 (en) * | 2005-01-31 | 2006-08-03 | Pharmacia & Upjohn Company Llc | Form iv crystalline celecoxib |
| WO2011055233A2 (en) | 2009-11-03 | 2011-05-12 | Actavis Group Ptc Ehf | Improved process for preparing celecoxib polymorph |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000042021A1 (en) * | 1999-01-14 | 2000-07-20 | Merck Frosst Canada & Co. | Synthesis of 4-[(5-substituted or unsubstituted phenyl) -3-substituted -1h-pyrazol -1-yl] benzenesulfonamides |
| WO2001042222A1 (en) * | 1999-12-08 | 2001-06-14 | Pharmacia Corporation | Polymorphic crystalline forms of celecoxib |
-
2003
- 2003-08-08 AU AU2003264861A patent/AU2003264861A1/en not_active Abandoned
- 2003-08-08 WO PCT/IN2003/000267 patent/WO2005014546A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000042021A1 (en) * | 1999-01-14 | 2000-07-20 | Merck Frosst Canada & Co. | Synthesis of 4-[(5-substituted or unsubstituted phenyl) -3-substituted -1h-pyrazol -1-yl] benzenesulfonamides |
| WO2001042222A1 (en) * | 1999-12-08 | 2001-06-14 | Pharmacia Corporation | Polymorphic crystalline forms of celecoxib |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006079923A2 (en) * | 2005-01-31 | 2006-08-03 | Pharmacia & Upjohn Company Llc | Form iv crystalline celecoxib |
| WO2006079923A3 (en) * | 2005-01-31 | 2006-12-07 | Pharmacia & Upjohn Co Llc | Form iv crystalline celecoxib |
| WO2011055233A2 (en) | 2009-11-03 | 2011-05-12 | Actavis Group Ptc Ehf | Improved process for preparing celecoxib polymorph |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003264861A1 (en) | 2005-02-25 |
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