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WO2006035293A1 - Polymorphic forms of quetiapine hemifumarate - Google Patents

Polymorphic forms of quetiapine hemifumarate Download PDF

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Publication number
WO2006035293A1
WO2006035293A1 PCT/IB2005/002860 IB2005002860W WO2006035293A1 WO 2006035293 A1 WO2006035293 A1 WO 2006035293A1 IB 2005002860 W IB2005002860 W IB 2005002860W WO 2006035293 A1 WO2006035293 A1 WO 2006035293A1
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Prior art keywords
quetiapine hemifumarate
hemifumarate
quetiapine
values
xrd pattern
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PCT/IB2005/002860
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French (fr)
Inventor
Bhargav Pandya
Ram Chander Aryan
Yatendra Kumar
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Ranbaxy Laboratories Ltd
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Ranbaxy Laboratories Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D281/16—[b, f]-condensed
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Definitions

  • the present invention relates to polymorphic forms of quetiapine hemifumarate, processes for their preparation and pharmaceutical compositions thereof.
  • quetiapine 2-[2-(4-dibenzo[Z?/J[l ,4]thiazepin-l l-ylpiperazin-l-yl)ethoxy]ethanol, commonly known as quetiapine (Formula I), is an antipsychotic drug belonging to the class of dibenzothiazepine derivatives. Quetiapine is commercially available in the form of its hemifumarate salt (2:1). Quetiapine hemifumarate is indicated for the management of the manifestations of psychotic disorders.
  • U.S. Patent No. 4,879,288 discloses a process for the preparation of quetiapine hemifumarate.
  • U.S. Patent No. 6,372,734 discloses a process for the purification of quetiapine which yields crystalline quetiapine.
  • WO 03/80065 provides crystalline forms of quetiapine hemifumarate referred to as Form II and Form III that are solvated polymorphic forms with dichloromethane and chloroform. Summary of the Invention
  • Form IV of quetiapine hemifumarate in one general aspect there is provided Form IV of quetiapine hemifumarate.
  • the Form IV polymorph of quetiapine hemifumarate includes a XRD pattern that includes 2 ⁇ values of 16.96, 22.96, and 23.77.
  • Embodiments of the present invention may include one or more of the following features.
  • the Form IV of of quetiapine hemifumarate may include 2 ⁇ values of 20.80, 21.50, and 24.08 or it may include 2 ⁇ values of 8.98, 12.58, 15.62, 19.62, and 21.92.
  • the Form IV of quetiapine hemifumarate may also include 2 ⁇ values of 8.98, 11.56, 11.90, 12.58, 13.92, 14.02, 14.32, 14.58, 15.04, 15.62, 15.84, 18.08, 18.40, 18.82, 19.62, 20.22, 20.80, 21.50, 21.92, 24.08, 25.48, 25.88, 26.80, 27.80, 28.00, 28.78, 29.26 and 30.30.
  • Form V of quetiapine hemifumarate in another general aspect there is provided Form V of quetiapine hemifumarate.
  • the Form V polymorph of quentiapine hemifumarate includes an XRD pattern that includes 2 ⁇ values at 16.80, 19.36, 22.72, and 23.16.
  • Embodiments of the present invention include one or more of the following features.
  • the Form V of quentiapine hemifumarate may include 2 ⁇ values at 11.64, 19.28, 19.58, and 23.46 or 2 ⁇ values at 7.52, 8.74, 1 1.64, 13.32, 14.26, 14.44, 14.92, 15.32, 15.72, 16.30, 17.54, 17.82, 18.38, 19.28, 19.58, 19.96, 20.20, 20.64, 20.94, 21.74, 22.32, 23.46, 23.84, 24.44, 25.18, 25.32, 26.32, 26.58, 26.64, 27.08, 27.96, 28.74, 29.06, 29.40, 29.94, 30.46, 30.82, 31.40, 31.76, 31.86, 32.10, 32.44, 33.00, 33.38, 34.04, 34.50, 35.10, 35.38, 36.12, 36.62, 37.50, 37.84, 38.30, 39.18 and 39.64.
  • a process for the preparation of Form IV of quetiapine hemifumarate includes heating quetiapine hemifumarate with chloroform to form a reaction mass, cooling the reaction mass and isolating Form IV of quetiapine hemifumarate, wherein the Form IV of quetiapine hemifumarate has a XRD pattern includes 2 ⁇ values of 16.96, 22.96, and 23.77.
  • a process for preparation of Form V of quetiapine hemifumarate includes stirring quetiapine hemifumarate in tetrahydrofuran to form a mixture, and isolating Form V of quetiapine hemifumarate from the mixture, wherein the Form V of quetiapine hemifumarate has an XRD pattern includes 2 ⁇ values at 16.80, 19.36, 22.72, and 23.16.
  • a pharmaceutical composition includes one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients.
  • a method for the management of the manifestations of psychotic disorders includes administering to a mammal in need thereof a pharmaceutical composition that includes one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients.
  • Figure 1 depicts an X-ray diffractogram of Form IV of quetiapine hemifumarate.
  • Figure 2 depicts a FTIR spectrum of Form IV of quetiapine hemifumarate
  • Figure 3 depicts an X-ray diffractogram of Form V of quetiapine hemifumarate.
  • Figure 4 depict FTIR spectrum of Form V of quetiapine hemifumarate.
  • Form IV and V polymorphic forms of quetiapine hemifumarate, hereinafter referred to as Form IV and V, which are characteristically different from the earlier knowns Form I, II and III.
  • the present invention provides for a polymorph of quetiapine hemifumarate, Form IV, having a X-Ray Powder Diffraction (XRD) pattern as depicted in Figure 1.
  • Form IV includes characteristic 2 ⁇ values at 8.98, 1 1.56, 1 1.90, 12.58, 13.92, 14.02, 14.32, 14.58, 15.04, 15.62, 15.84, 16.96, 18.08, 18.40, 18.82, 19.62, 20.22, 20.80, 21.50, 21.92, 22.96, 23.70, 24.08, 25.48, 25.88, 26.80, 27.80, 28.00, 28.78, 29.26 and 30.30.
  • Form IV of quetiapine hemifumarate is a chloroform solvate of quetiapine hemifumarate.
  • FTIR Fourier Transform Infrared
  • Form V includes characteristic 2 ⁇ values at 7.52, 8.74, 1 1.64, 13.32, 14.26, 14.44, 14.92, 15.32, 15.72, 16.30, 16.80, 17.54, 17.82, 18.38, 19.28, 19.36, 19.58, 19.96, 20.20, 20.64, 20.94, 21.74, 22.32, 22.72, 23.16, 23.46, 23.84, 24.44, 25.18, 25.32, 26.32, 26.58, 26.64, 27.08, 27.96, 28.74, 29.06, 29.40, 29.94, 30.46, 30.82, 31.40, 31.76, 31.86, 32.10, 32.44, 33.00, 33.38, 34.04, 34.50, 35.10, 35.38, 36.12, 36.62, 37.50, 37.84, 38.30, 39
  • Form V of quetiapine hemifumarate is a tetrahydrofuran solvate of quetiapine hemifumarate.
  • the Fourier Transform Infrared (FTIR) spectrum of Form V of quetiapine hemifumarate in potassium bromide is depicted in Figure 4.
  • Also provided in the present invention is a process for preparation of Form IV of quetiapine hemifumarate. The process includes heating quetiapine hemifumarate with chloroform to form a reaction mass, cooling the reaction mass and isolating Form IV of quetiapine hemifumarate.
  • the quetiapine hemifumarate may be prepared by any processes reported in the art.
  • the quetiapine hemifurate is heated in chloroform and the resultant reaction mass is slowly cooled.
  • the reaction mass is separated, filtered and dried under vacuum at ambient temperature for 3 hours to get Form IV of quetiapine hemifumarate.
  • the process includes stirring quetiapine hemifumarate in tetrahydrofuran and isolating Form V of quetiapine hemifumarate from the mixture.
  • Quetiapine hemifumarate is stirred with tetrahydrofuran at ambient temperature for 3 hours to 80 hours and the resultant mass is filtered and dried under vacuum to get Form V of quetiapine hemifumarate.
  • compositions which include Form IV and/or Form V of quetiapine hemifumarate.
  • the pharmaceutical compositions may include one or more pharmaceutically acceptable excipients.
  • the present invention also provides a method for the management of the manifestations of psychotic disorders.
  • the method includes administering to a mammal in need thereof a therapeutically effective amount of Form IV and/or Form V of quetiapine hemifumarate.
  • Example 1 Preparation of Form IV of Quetiapine Hemifumarate
  • Quetiapine hemifumarate (2 gm) was heated with chloroform (10 ml) for 30 minutes at reflux temperature. The resultant mass was cooled to an ambient temperature and stirred for between 28 to 30 hours. The separated product was filtered and washed with chilled chloroform. The resulting cake was dried in a vacuum oven at about 25 0 C to 3O 0 C for between 4 to 16 hours to get Form IV of quetiapine hemifumarate. Yield: 1.6 gm.
  • Example 2 Preparation of Form V of Quetiapine Hemifumarate Quetiapine hemifumarate Form IV (1 gm) was mixed in to tetrahydrofuran (10 ml).

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Abstract

The present invention relates to novel polymorphic forms of quetiapine hemifumarate, process for their preparation and pharmaceutical compositions thereof.

Description

POLYMORPHIC FORMS OF QUETIAPINE HEMIFUMARATE
Field of the Invention
The present invention relates to polymorphic forms of quetiapine hemifumarate, processes for their preparation and pharmaceutical compositions thereof.
Background of the Invention
2-[2-(4-dibenzo[Z?/J[l ,4]thiazepin-l l-ylpiperazin-l-yl)ethoxy]ethanol, commonly known as quetiapine (Formula I), is an antipsychotic drug belonging to the class of dibenzothiazepine derivatives. Quetiapine is commercially available in the form of its hemifumarate salt (2:1). Quetiapine hemifumarate is indicated for the management of the manifestations of psychotic disorders.
Figure imgf000002_0001
FORMULA I
U.S. Patent No. 4,879,288 discloses a process for the preparation of quetiapine hemifumarate. U.S. Patent No. 6,372,734 discloses a process for the purification of quetiapine which yields crystalline quetiapine. However, no physical characteristics, such as X-Ray Diffraction Pattern or Infrared spectrum data of the crystalline form, have been reported in this patent.
WO 03/80065 provides crystalline forms of quetiapine hemifumarate referred to as Form II and Form III that are solvated polymorphic forms with dichloromethane and chloroform. Summary of the Invention
In one general aspect there is provided Form IV of quetiapine hemifumarate. The Form IV polymorph of quetiapine hemifumarate includes a XRD pattern that includes 2Θ values of 16.96, 22.96, and 23.77. Embodiments of the present invention may include one or more of the following features. For example, the Form IV of of quetiapine hemifumarate may include 2Θ values of 20.80, 21.50, and 24.08 or it may include 2Θ values of 8.98, 12.58, 15.62, 19.62, and 21.92. The Form IV of quetiapine hemifumarate may also include 2Θ values of 8.98, 11.56, 11.90, 12.58, 13.92, 14.02, 14.32, 14.58, 15.04, 15.62, 15.84, 18.08, 18.40, 18.82, 19.62, 20.22, 20.80, 21.50, 21.92, 24.08, 25.48, 25.88, 26.80, 27.80, 28.00, 28.78, 29.26 and 30.30.
In another general aspect there is provided Form V of quetiapine hemifumarate. The Form V polymorph of quentiapine hemifumarate includes an XRD pattern that includes 2Θ values at 16.80, 19.36, 22.72, and 23.16. Embodiments of the present invention include one or more of the following features. For example, the Form V of quentiapine hemifumarate may include 2Θ values at 11.64, 19.28, 19.58, and 23.46 or 2Θ values at 7.52, 8.74, 1 1.64, 13.32, 14.26, 14.44, 14.92, 15.32, 15.72, 16.30, 17.54, 17.82, 18.38, 19.28, 19.58, 19.96, 20.20, 20.64, 20.94, 21.74, 22.32, 23.46, 23.84, 24.44, 25.18, 25.32, 26.32, 26.58, 26.64, 27.08, 27.96, 28.74, 29.06, 29.40, 29.94, 30.46, 30.82, 31.40, 31.76, 31.86, 32.10, 32.44, 33.00, 33.38, 34.04, 34.50, 35.10, 35.38, 36.12, 36.62, 37.50, 37.84, 38.30, 39.18 and 39.64.
In another general aspect there is provided a process for the preparation of Form IV of quetiapine hemifumarate. The process includes heating quetiapine hemifumarate with chloroform to form a reaction mass, cooling the reaction mass and isolating Form IV of quetiapine hemifumarate, wherein the Form IV of quetiapine hemifumarate has a XRD pattern includes 2Θ values of 16.96, 22.96, and 23.77.
In another general aspect there is provided a process for preparation of Form V of quetiapine hemifumarate. The process includes stirring quetiapine hemifumarate in tetrahydrofuran to form a mixture, and isolating Form V of quetiapine hemifumarate from the mixture, wherein the Form V of quetiapine hemifumarate has an XRD pattern includes 2Θ values at 16.80, 19.36, 22.72, and 23.16. In another general aspect there is provided a pharmaceutical composition. The pharmaceutical composition includes one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients.
In another general aspect there is provided a method for the management of the manifestations of psychotic disorders. The method includes administering to a mammal in need thereof a pharmaceutical composition that includes one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients.
Brief Description of the Drawings Figure 1 depicts an X-ray diffractogram of Form IV of quetiapine hemifumarate. Figure 2 depicts a FTIR spectrum of Form IV of quetiapine hemifumarate Figure 3 depicts an X-ray diffractogram of Form V of quetiapine hemifumarate. Figure 4 depict FTIR spectrum of Form V of quetiapine hemifumarate.
Detailed Description of the Invention
The present inventors have surprisingly found two polymorphic forms of quetiapine hemifumarate, hereinafter referred to as Form IV and V, which are characteristically different from the earlier knowns Form I, II and III.
The present invention provides for a polymorph of quetiapine hemifumarate, Form IV, having a X-Ray Powder Diffraction (XRD) pattern as depicted in Figure 1. Form IV includes characteristic 2Θ values at 8.98, 1 1.56, 1 1.90, 12.58, 13.92, 14.02, 14.32, 14.58, 15.04, 15.62, 15.84, 16.96, 18.08, 18.40, 18.82, 19.62, 20.22, 20.80, 21.50, 21.92, 22.96, 23.70, 24.08, 25.48, 25.88, 26.80, 27.80, 28.00, 28.78, 29.26 and 30.30. Form IV of quetiapine hemifumarate is a chloroform solvate of quetiapine hemifumarate. The Fourier Transform Infrared (FTIR) spectrum of Form IV of quetiapine hemifumarate in potassium bromide is depicted in Figure 2.
Also provided is another polymorph of quetiapine hemifumarate, Form V, having an XRD pattern as depicted in Figure 3. Form V includes characteristic 2Θ values at 7.52, 8.74, 1 1.64, 13.32, 14.26, 14.44, 14.92, 15.32, 15.72, 16.30, 16.80, 17.54, 17.82, 18.38, 19.28, 19.36, 19.58, 19.96, 20.20, 20.64, 20.94, 21.74, 22.32, 22.72, 23.16, 23.46, 23.84, 24.44, 25.18, 25.32, 26.32, 26.58, 26.64, 27.08, 27.96, 28.74, 29.06, 29.40, 29.94, 30.46, 30.82, 31.40, 31.76, 31.86, 32.10, 32.44, 33.00, 33.38, 34.04, 34.50, 35.10, 35.38, 36.12, 36.62, 37.50, 37.84, 38.30, 39.18 and 39.64. Form V of quetiapine hemifumarate is a tetrahydrofuran solvate of quetiapine hemifumarate. The Fourier Transform Infrared (FTIR) spectrum of Form V of quetiapine hemifumarate in potassium bromide is depicted in Figure 4. Also provided in the present invention is a process for preparation of Form IV of quetiapine hemifumarate. The process includes heating quetiapine hemifumarate with chloroform to form a reaction mass, cooling the reaction mass and isolating Form IV of quetiapine hemifumarate.
The quetiapine hemifumarate may be prepared by any processes reported in the art. The quetiapine hemifurate is heated in chloroform and the resultant reaction mass is slowly cooled. The reaction mass is separated, filtered and dried under vacuum at ambient temperature for 3 hours to get Form IV of quetiapine hemifumarate.
Also provided is a process for preparation of Form V of quetiapine hemifumarate. The process includes stirring quetiapine hemifumarate in tetrahydrofuran and isolating Form V of quetiapine hemifumarate from the mixture.
Quetiapine hemifumarate is stirred with tetrahydrofuran at ambient temperature for 3 hours to 80 hours and the resultant mass is filtered and dried under vacuum to get Form V of quetiapine hemifumarate.
Also provided are pharmaceutical compositions which include Form IV and/or Form V of quetiapine hemifumarate. The pharmaceutical compositions may include one or more pharmaceutically acceptable excipients.
The present invention also provides a method for the management of the manifestations of psychotic disorders. The method includes administering to a mammal in need thereof a therapeutically effective amount of Form IV and/or Form V of quetiapine hemifumarate.
The following examples are intended to illustrate the invention and not to be construed as limiting the scope of the invention in any way. Example 1 : Preparation of Form IV of Quetiapine Hemifumarate
Quetiapine hemifumarate (2 gm) was heated with chloroform (10 ml) for 30 minutes at reflux temperature. The resultant mass was cooled to an ambient temperature and stirred for between 28 to 30 hours. The separated product was filtered and washed with chilled chloroform. The resulting cake was dried in a vacuum oven at about 250C to 3O0C for between 4 to 16 hours to get Form IV of quetiapine hemifumarate. Yield: 1.6 gm.
Example 2: Preparation of Form V of Quetiapine Hemifumarate Quetiapine hemifumarate Form IV (1 gm) was mixed in to tetrahydrofuran (10 ml).
The resultant mass was stirred at an ambient temperature for between 48 to 58 hours. The separated product was filtered and washed with chilled tetrahydrofuran. The resulting cake was dried in a vacuum oven at about 250C to 3O0C for between 4 to 12 hours to get Form V of quetiapine hemifumarate. Yield: 0.83 gm.
While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are included within the scope of the present invention.

Claims

We Claim: 1. Form IV of quetiapine hemifumarate having an XRD Pattern comprising 2Θ values of 16.96, 22.96, and 23.77. 2. The Form IV of quetiapine hemifumarate of claim 1, further comprising 2Θ values of 20.80, 21.50, and 24.08. 3. The Form IV of quetiapine hemifumarate of claim 1, further comprising 2Θ values of 8.98, 12.58, 15.62, 19.62, and 21.92. 4. The Form IV of quetiapine hemifumarate of claim 1, further comprising 2Θ values of 8.98, 1 1.56, 11.90, 12.58, 13.92, 14.02, 14.32, 14.58, 15.04, 15.62, 15.84, 18.08, 18.40, 18.82, 19.62, 20.22, 20.80, 21.50, 21.92, 24.08, 25.48, 25.88, 26.80, 27.80, 28.00, 28.78, 29.26 and 30.30. 5. Form V of quetiapine hemifumarate having an XRD pattern comprising 2Θ values at 16.80, 19.36, 22.72, and 23.16. 6. The Form V of quentiapine hemifumarate of claim 5, further comprising 2Θ values at 11.64, 19.28, 19.58, and 23.46. 7. The Form V of quentiapine hemifumarate of claim 5, further comprising 2Θ values at 7.52, 8.74, 11.64, 13.32, 14.26, 14.44, 14.92, 15.32, 15.72, 16.30, 17.54, 17.82, 18.38, 19.28, 19.58, 19.96, 20.20, 20.64, 20.94, 21.74, 22.32, 23.46, 23.84, 24.44, 25.18, 25.32, 26.32, 26.58, 26.64, 27.08, 27.96, 28.74, 29.06, 29.40, 29.94, 30.46, 30.82, 31.40, 31.76, 31.86, 32.10, 32.44, 33.00, 33.38, 34.04, 34.50, 35.10, 35.38, 36.12, 36.62, 37.50, 37.84, 38.30, 39.18 and 39.64. 8. A process for preparation of Form IV of quetiapine hemifumarate, the process comprising heating quetiapine hemifumarate with chloroform to form a reaction mass, and cooling the reaction mass and isolating Form IV of quetiapine hemifumarate, wherein the Form IV of quetiapine hemifumarate has an XRD Pattern comprising 2Θ values of 16.96, 22.96, and 23.77. 9. The process of claim 8, wherein the isolated quetiapine hemifumarate is dried in a vacuum oven at about 250C to about 3O0C for between 4 to 16 hours. 10. A process for preparation of Form V of quetiapine hemifumarate, the process comprising stirring quetiapine hemifumarate in tetrahydrofuran to form a mixture, and isolating Form V of quetiapine hemifumarate from the mixture, wherein the Form V of quetiapine hemifumarate has an XRD pattern comprising 2Θ values at 16.80, 19.36, 22.72, and 23.16. 11. The process of claim 10, wherein the isolated quetiapine hemifumarate is dried in a vacuum oven at about 250C to about 3O0C for between 4 to 16 hours. 12. A pharmaceutical composition comprising one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients. 13. A method for the management of the manifestations of psychotic disorders, the method comprising administering to a mammal in need thereof a pharmaceutical composition comprising one or both of Form IV or Form V of quetiapine hemifumarate and one or more pharmaceutically acceptable excipients.
PCT/IB2005/002860 2004-09-27 2005-09-27 Polymorphic forms of quetiapine hemifumarate Ceased WO2006035293A1 (en)

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US7687622B2 (en) 2005-04-14 2010-03-30 Teva Pharmaceutical Industries, Ltd Process for preparing quetiapine fumarate
WO2010100623A1 (en) 2009-03-04 2010-09-10 Ranbaxy Laboratories Limited Process for the preparation of quetiapine fumarate

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7687622B2 (en) 2005-04-14 2010-03-30 Teva Pharmaceutical Industries, Ltd Process for preparing quetiapine fumarate
WO2010100623A1 (en) 2009-03-04 2010-09-10 Ranbaxy Laboratories Limited Process for the preparation of quetiapine fumarate

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