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US20090227645A1 - Pharmaceutical compositions of valdecoxib - Google Patents

Pharmaceutical compositions of valdecoxib Download PDF

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Publication number
US20090227645A1
US20090227645A1 US12/403,709 US40370909A US2009227645A1 US 20090227645 A1 US20090227645 A1 US 20090227645A1 US 40370909 A US40370909 A US 40370909A US 2009227645 A1 US2009227645 A1 US 2009227645A1
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Prior art keywords
valdecoxib
pharmaceutical composition
ray powder
powder diffraction
present
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US12/403,709
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Kesireddy Subadsh Chander Reddy
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Hetero Drugs Ltd
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Hetero Drugs Ltd
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Priority to US12/403,709 priority Critical patent/US20090227645A1/en
Assigned to HETERO DRUGS LIMITED reassignment HETERO DRUGS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: REDDY, BANDI PARTHASARADHI, REDDY, DASARI MURALIDHARA, REDDY, KRESIREDDY SUBADSH, REDDY, KURA RATHNAKAR, REDDY, RAPOLU RAJI
Assigned to HETERO DRUGS LIMITED reassignment HETERO DRUGS LIMITED CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR'S NAME PREVIOUSLY RECORDED ON REEL 022392 FRAME 0966. ASSIGNOR(S) HEREBY CONFIRMS THE KESIREDDY SUBADSH REDDY. Assignors: REDDY, KESIREDDY SUBADSH
Publication of US20090227645A1 publication Critical patent/US20090227645A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to novel crystalline forms of valdecoxib, to processes for their preparation and to pharmaceutical compositions containing them.
  • 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide is a highly selective and potent cyclooxygenase-2 inhibitor in human whole blood and useful for the treatment of arthritis and pain.
  • the therapeutic uses of valdecoxib are disclosed in WO 9625405.
  • the object of the present invention is to provide stable novel crystalline forms of valdecoxib, processes for preparing these forms and pharmaceutical compositions containing them.
  • FIG. 1 shows typical form I x-ray powder diffraction pattern.
  • a process for preparation of valdecoxib form I.
  • valdecoxib is dissolved in dimethyl formamide or N,N-dimethyl acetamide and valdecoxib form I is isolated from the solution.
  • Valdecoxib in any crystalline form may be used. If valdecoxib form I is used in the process, its serves as a method of purification of valdecoxib form I.
  • a mixture of dimethyl formamide and N,N-dimethyl acetamide; or dimethyl formamide or N,N-dimethyl acetamide mixed with any other solvent may be used.
  • Valdecoxib form I can be isolated by the techniques like cooling, partial removal of the solvent or combination thereof.
  • Crystallization may be initiated with the aid of seed crystals.
  • valdecoxib is mixed with dimethyl formamide or N,N-dimethyl acetamide and heated to about 50° C. to reflux temperature.
  • the solution so formed is preferably maintained at 25° C. to 30° C. for 3 to 5 hours and the valdecoxib form I crystals formed are separated by filtration or centrifugation.
  • a novel crystalline form of valdecoxib designated as form II, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 12.2, 15.4, 15.9, 19.9, 20.6, 22.0, 23.0, 23.6, 23.9, 24.5, 25.1, 28.6 and 31.3 degrees.
  • FIG. 2 shows typical form II x-ray powder diffraction pattern.
  • a process for preparation of valdecoxib form II.
  • valdecoxib is dissolved in acetonitrile and isolated valdecoxib form II from the solution.
  • Valdecoxib in any crystalline form may be used.
  • valdecoxib is dissolved in acetonitrile at about 40° C. to 45° C. and valdecoxib form II is separated at about 25° C.-30° C.
  • the valdecoxib form II may be collected by filtration or centrifugation.
  • a novel crystalline form of valdecoxib designated as form III, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 11.6, 12.2, 12.9, 13.3, 15.4, 15.7, 16.7, 17.0, 17.4, 18.1, 19.7, 20.6, 21.9, 22.4, 23.1, 23.4, 23.8, 24.4, 25.3, 25.7, 26.1, 28.5 and 29.7 degrees.
  • FIG. 3 shows typical form III x-ray powder diffraction pattern.
  • a process for preparation of valdecoxib form III.
  • valdecoxib is dissolved in an ester solvent and isolated valdecoxib form III from the solution.
  • the solution is cooled to 5° C. to 30° C. to get the crystals of valdecoxib form III.
  • the valdecoxib form III may be collected by filtration or centrifugation. Valdecoxib in any crystalline form may be used in the process.
  • the suitable ester solvent is selected from n-butyl acetate, ethyl acetate, methyl acetate, isopropyl acetate, tert-butyl acetate, ethyl formate, methyl formate.
  • a combination of the ester solvents may also be used.
  • a pharmaceutical composition comprising form I of valdecoxib and a pharmaceutically acceptable carrier or diluent.
  • a pharmaceutical composition comprising form II of valdecoxib and a pharmaceutically acceptable carrier or diluent.
  • a pharmaceutical composition comprising form III of valdecoxib and a pharmaceutically acceptable carrier or diluent.
  • FIG. 1 is a x-ray powder diffraction spectrum of valdecoxib form I.
  • FIG. 2 is a x-ray powder diffraction spectrum of valdecoxib form II.
  • FIG. 3 is a x-ray powder diffraction spectrum of valdecoxib form III.
  • x-Ray powder diffraction spectrum was measured on a Siemens D5000 x-ray powder diffractometer having a copper-K ⁇ radiation.
  • Valdecoxib (10 gm, obtained by the process described in example 1 of WO 9625405) is dissolved in dimethyl formamide (50 ml), heated to 50° C. and the solution obtained is cooled to 25° C. and maintained at 25° C. to 30° C. for 3 hours. The separated crystals are filtered to give 9 gm of valdecoxib form I.
  • Valdecoxib (10 gm) is dissolved in acetonitrile (125 ml), heated to 40° C. and the solution obtained is cooled to 25° C. and maintained at 25° C. to 30° C. for 6 hours. The separated crystals are filtered to give 9.5 gm of valdecoxib form II.
  • Example 1 is repeated using valdecoxib form II for valdecoxib to give valdecoxib form I.
  • Example 2 is repeated using valdecoxib form I for valdecoxib to give valdecoxib form II.
  • Valdecoxib (10 gm) is mixed with n-butyl acetate (100 ml), heated to 80° C. The solution so formed is cooled to 25° C. and maintained at about 25° C. for 5 hours. The separated crystals are filtered to give 8.5 gm of valdecoxib form III.
  • Example 5 is repeated using valdecoxib form II for valdecoxib to give valdecoxib form III.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to novel crystalline forms of valdecoxib, to processes for their preparation and to pharmaceutical compositions containing them.

Description

    FIELD OF THE INVENTION
  • The present invention relates to novel crystalline forms of valdecoxib, to processes for their preparation and to pharmaceutical compositions containing them.
    • BACKGROUND OF THE INVENTION Valdecoxib of Formula (I)
  • Figure US20090227645A1-20090910-C00001
  • or 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide is a highly selective and potent cyclooxygenase-2 inhibitor in human whole blood and useful for the treatment of arthritis and pain. The therapeutic uses of valdecoxib are disclosed in WO 9625405.
  • Two crystalline forms of valdecoxib, form A and form B, are mentioned in WO 9806708.
  • We have discovered three stable novel crystalline forms of valdecoxib and these forms are found to be suitable for pharmaceutical preparations.
  • The object of the present invention is to provide stable novel crystalline forms of valdecoxib, processes for preparing these forms and pharmaceutical compositions containing them.
    • DETAILED DESCRIPTION OF THE INVENTION
  • In accordance with the present invention, there is provided a novel crystalline form of valdecoxib, designated as form 1, characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 9.7, 13.1, 14.0, 14.5, 17.0, 17.1, 17.7, 19.4, 20.9, 21.3, 21.8, 24.1, 25.4, 26.3 and 29.1 degrees. FIG. 1 shows typical form I x-ray powder diffraction pattern.
  • In accordance with the present invention, a process is provided for preparation of valdecoxib form I. In this process, valdecoxib is dissolved in dimethyl formamide or N,N-dimethyl acetamide and valdecoxib form I is isolated from the solution. Valdecoxib in any crystalline form may be used. If valdecoxib form I is used in the process, its serves as a method of purification of valdecoxib form I. A mixture of dimethyl formamide and N,N-dimethyl acetamide; or dimethyl formamide or N,N-dimethyl acetamide mixed with any other solvent may be used. Valdecoxib form I can be isolated by the techniques like cooling, partial removal of the solvent or combination thereof. Crystallization may be initiated with the aid of seed crystals. Preferably, valdecoxib is mixed with dimethyl formamide or N,N-dimethyl acetamide and heated to about 50° C. to reflux temperature. The solution so formed is preferably maintained at 25° C. to 30° C. for 3 to 5 hours and the valdecoxib form I crystals formed are separated by filtration or centrifugation.
  • In accordance with the present invention, there is provided a novel crystalline form of valdecoxib, designated as form II, characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 12.2, 15.4, 15.9, 19.9, 20.6, 22.0, 23.0, 23.6, 23.9, 24.5, 25.1, 28.6 and 31.3 degrees. FIG. 2 shows typical form II x-ray powder diffraction pattern.
  • In accordance with the present invention, a process is provided for preparation of valdecoxib form II. In this process, valdecoxib is dissolved in acetonitrile and isolated valdecoxib form II from the solution. Valdecoxib in any crystalline form may be used. Preferably valdecoxib is dissolved in acetonitrile at about 40° C. to 45° C. and valdecoxib form II is separated at about 25° C.-30° C. The valdecoxib form II may be collected by filtration or centrifugation.
  • In accordance with the present invention, there is provided a novel crystalline form of valdecoxib, designated as form III, characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 11.6, 12.2, 12.9, 13.3, 15.4, 15.7, 16.7, 17.0, 17.4, 18.1, 19.7, 20.6, 21.9, 22.4, 23.1, 23.4, 23.8, 24.4, 25.3, 25.7, 26.1, 28.5 and 29.7 degrees. FIG. 3 shows typical form III x-ray powder diffraction pattern.
  • In accordance with the present invention, a process is provided for preparation of valdecoxib form III. In this process, valdecoxib is dissolved in an ester solvent and isolated valdecoxib form III from the solution. Preferably the solution is cooled to 5° C. to 30° C. to get the crystals of valdecoxib form III. The valdecoxib form III may be collected by filtration or centrifugation. Valdecoxib in any crystalline form may be used in the process. The suitable ester solvent is selected from n-butyl acetate, ethyl acetate, methyl acetate, isopropyl acetate, tert-butyl acetate, ethyl formate, methyl formate. A combination of the ester solvents may also be used.
  • In accordance with the present invention, there is provided a pharmaceutical composition comprising form I of valdecoxib and a pharmaceutically acceptable carrier or diluent.
  • In accordance with the present invention, there is provided a pharmaceutical composition comprising form II of valdecoxib and a pharmaceutically acceptable carrier or diluent.
  • In accordance with the present invention, there is provided a pharmaceutical composition comprising form III of valdecoxib and a pharmaceutically acceptable carrier or diluent.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a x-ray powder diffraction spectrum of valdecoxib form I.
  • FIG. 2 is a x-ray powder diffraction spectrum of valdecoxib form II.
  • FIG. 3 is a x-ray powder diffraction spectrum of valdecoxib form III.
    •
  • x-Ray powder diffraction spectrum was measured on a Siemens D5000 x-ray powder diffractometer having a copper-Kα radiation.
  • The following examples are given for the purpose of illustrating the present invention and should not be considered as limitations on the scope of spirit of the invention.
    • Example 1
  • Valdecoxib (10 gm, obtained by the process described in example 1 of WO 9625405) is dissolved in dimethyl formamide (50 ml), heated to 50° C. and the solution obtained is cooled to 25° C. and maintained at 25° C. to 30° C. for 3 hours. The separated crystals are filtered to give 9 gm of valdecoxib form I.
    • Example 2
  • Valdecoxib (10 gm) is dissolved in acetonitrile (125 ml), heated to 40° C. and the solution obtained is cooled to 25° C. and maintained at 25° C. to 30° C. for 6 hours. The separated crystals are filtered to give 9.5 gm of valdecoxib form II.
    • Example 3
  • Example 1 is repeated using valdecoxib form II for valdecoxib to give valdecoxib form I.
    • Example 4
  • Example 2 is repeated using valdecoxib form I for valdecoxib to give valdecoxib form II.
    • Example 5
  • Valdecoxib (10 gm) is mixed with n-butyl acetate (100 ml), heated to 80° C. The solution so formed is cooled to 25° C. and maintained at about 25° C. for 5 hours. The separated crystals are filtered to give 8.5 gm of valdecoxib form III.
    • Example 6
  • Example 5 is repeated using valdecoxib form II for valdecoxib to give valdecoxib form III.

Claims (7)

1-14. (canceled)
15. A pharmaceutical composition comprising stable valdecoxib form I characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 9.7, 13.1, 14.0, 14.5, 17.0, 17.1, 17.7, 19.4, 20.9, 21.3, 21.8, 24.1, 25.4, 26.3 and 29.1 degrees and a pharmaceutically acceptable carrier or diluent.
16-17. (canceled)
18. The pharmaceutical composition of claim 15, wherein the valdecoxib form I is further characterized by an x-ray powder diffraction pattern as in FIG. 1.
19. The pharmaceutical composition of claim 15, wherein the valdecoxib form I is prepared by a process which comprises the steps of: (a) dissolving valdecoxib in dimethyl formamide or N,N-dimethyl acetamide; and (b) isolating valdecoxib form I from the solution.
20. The pharmaceutical composition of claim 19, wherein valdecoxib is dissolved in dimethyl formamide.
21. The pharmaceutical composition of claim 19, wherein the solution formed in (a) is cooled to 25° C. to 30° C. and the separated crystals are collected by filtration or centrifugation.
US12/403,709 2003-04-04 2009-03-13 Pharmaceutical compositions of valdecoxib Abandoned US20090227645A1 (en)

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US10/510,333 US7538126B2 (en) 2003-04-04 2003-04-04 Crystalline forms of valdecoxib
PCT/IN2003/000139 WO2004087683A1 (en) 2003-04-04 2003-04-04 Novel crystalline forms of valdecoxib
INPCT/IN03/00139 2003-04-04
US12/403,709 US20090227645A1 (en) 2003-04-04 2009-03-13 Pharmaceutical compositions of valdecoxib

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ334132A (en) * 1996-08-14 2000-06-23 G Crystalline form of 4-[5-methyl-3-phenylisoxazol-4-yl]benzenesulfonamide
CN114634457A (en) * 2022-04-21 2022-06-17 济南立德医药技术有限公司 Refining method of valdecoxib

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5633373A (en) * 1989-07-07 1997-05-27 Eli Lilly And Company Enantioselective synthesis of antifolates

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* Cited by examiner, † Cited by third party
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BR9607035A (en) 1995-02-13 1997-11-04 Searle & Co Isoxazois replaced for the treatment of inflammation
US5633272A (en) * 1995-02-13 1997-05-27 Talley; John J. Substituted isoxazoles for the treatment of inflammation
NZ334132A (en) 1996-08-14 2000-06-23 G Crystalline form of 4-[5-methyl-3-phenylisoxazol-4-yl]benzenesulfonamide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5633373A (en) * 1989-07-07 1997-05-27 Eli Lilly And Company Enantioselective synthesis of antifolates

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AU2003238668A1 (en) 2004-10-25
US7538126B2 (en) 2009-05-26
WO2004087683A1 (en) 2004-10-14

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