WO2015040605A1 - Crystalline form of mirabegron - Google Patents

Crystalline form of mirabegron Download PDF

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Publication number
WO2015040605A1
WO2015040605A1 PCT/IB2014/064784 IB2014064784W WO2015040605A1 WO 2015040605 A1 WO2015040605 A1 WO 2015040605A1 IB 2014064784 W IB2014064784 W IB 2014064784W WO 2015040605 A1 WO2015040605 A1 WO 2015040605A1
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Prior art keywords
mirabegron
crystalline form
peaks
xrpd pattern
formula
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PCT/IB2014/064784
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French (fr)
Inventor
Sangeeta SANGWAN
Poonam KAUSHIK
Israr ALI
Ram Thaimattam
Mohan Prasad
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Ranbaxy Laboratories Limited
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Publication of WO2015040605A1 publication Critical patent/WO2015040605A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38Nitrogen atoms
    • C07D277/40Unsubstituted amino or imino radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Definitions

  • the present invention provides a crystalline form of mirabegron, a process for its preparation, a pharmaceutical composition comprising it, and its use for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.
  • Mirabegron is a beta-3 adrenergic agonist disclosed in U.S. Patent No. 6,346,532. It is chemically designated as 2-(2-aminothiazol-4-yl)-N-[4-[2- ⁇ [(2R)-2-hydroxy-2- phenylethyl]amino ⁇ ethyl)phenyl]acetamide, having the structure depicted by Formula I.
  • U.S. Patent No. 7,342,117 discloses a-Form and ⁇ -Form of mirabegron;
  • PCT Publication No. WO 2012/156998 discloses an amorphous form of mirabegron;
  • IPCOM000228561D discloses crystalline forms of mirabegron and mirabegron monohydrochloride .
  • the present invention provides a crystalline form of mirabegron, a process for its preparation, a pharmaceutical composition comprising it, and its use for the treatment of overactive bladder.
  • the crystalline form of mirabegron of the present invention is highly pure and free- flowing. It is stable towards polymorphic conversion and shows little or no variation in dissolution profile.
  • a first aspect of the present invention provides a crystalline form of mirabegron characterized by an X-ray powder diffraction (XRPD) pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A.
  • XRPD X-ray powder diffraction
  • a second aspect of the present invention provides a process for the preparation of a crystalline form of mirabegron of Formula I characterized by an XRPD pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A
  • a third aspect of the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a crystalline form of mirabegron characterized by an XRPD pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A and one or more
  • a fourth aspect of the present invention provides use of a crystalline form of mirabegron, characterized by an X-ray powder diffraction having peaks at d-spacings of about 5.74, 4.41, 4.28, 4.16, and 3.80 A, for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.
  • Figure 1 X-Ray Powder Diffraction (XRPD) pattern of the crystalline form of mirabegron.
  • FIG. 2 Differential Scanning Calorimetry (DSC) thermogram of the crystalline form of mirabegron.
  • Figure 3 Thermogravimetric Analysis (TGA) of the crystalline form of mirabegron.
  • contacting includes dissolving, mixing, slurrying, stirring, or combinations thereof.
  • the crystalline form of mirabegron is characterized by an XRPD pattern having peaks at d-spacing of 5.74, 4.41, 4.28, 4.16, and 3.80 A.
  • the crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at d-spacing of 19.85, 7.17, 4.90, and 3.15 A.
  • the crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at 15.44, 20.13, 20.75, 21.36, and 23.44 ⁇ 0.2 degrees 2 ⁇ .
  • the crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at 4.45, 12.34, 18.14, and 28.35 ⁇ 0.2 degrees 2 ⁇ .
  • Table 1 summarizes the d-spacing values in A, and the corresponding 2 ⁇ values of the crystalline form of mirabegron of Formula I.
  • the crystalline form of mirabegron is further characterized by a DSC thermogram having endotherms at about 120.28°C and about 142.68°C.
  • the crystalline form of mirabegron is further characterized by an XRPD pattern, a DSC thermogram, and a TGA as depicted in Figure 1, Figure 2, and Figure 3, respectively.
  • Mirabegron which is used for the preparation of mirabegron dimethyl sulphoxide solvate, may be prepared by any method known in the art, such as those described in U.S. Patent No. 7,342,117 or PCT Publication No. WO 2012/156998, which are incorporated herein by reference.
  • the preparation of the mirabegron dimethyl sulphoxide solvate of Formula II is carried out by contacting mirabegron with dimethyl sulphoxide in the presence of a solvent at a temperature of about 20°C to the reflux temperature of the solvent.
  • the solvent is selected from the group consisting of aromatic hydrocarbons, alkyl acetates, and mixtures thereof. Examples of aromatic hydrocarbons include toluene and xylene.
  • alkyl acetates examples include ethyl acetate, propyl acetate, and /-butyl acetate.
  • the reaction mixture is stirred at a temperature of about 25 °C to about 35°C for about 1 hour to about 4 hours, filtered, washed with the solvent, and dried at a temperature of about 20°C to about 40°C for about 30 minutes to about 20 hours to provide mirabegron dimethyl sulphoxide solvate of Formula II.
  • the preparation of a crystalline form of mirabegron of Formula I characterized by XRPD peaks at d-spacing values of about 5.74, 4.41, 4.28, 4.16, and 3.80 A is carried out by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 70°C to about 80°C for about 2 hours to about 8 hours. Any suitable method of drying may be employed, such as drying under reduced pressure, vacuum tray drying, air drying, or combinations thereof.
  • the crystalline form of mirabegron is prepared by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 70°C to about 75 °C in a vacuum tray dryer for about 5 hours to about 6 hours.
  • the crystalline form of mirabegron is prepared by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 75 °C to about 80°C in a vacuum tray dryer for about 2 hours to about 6 hours.
  • crystalline form of mirabegron of the present invention may be administered as part of a pharmaceutical composition for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency. Accordingly, in a further aspect, there is provided a pharmaceutical composition comprising the crystalline form of mirabegron of the present invention, one or more pharmaceutically acceptable carriers, diluents, or excipients, and optionally other therapeutic ingredients.
  • compositions comprising the crystalline form of mirabegron of the present invention may be administered orally, topically, parenterally, by inhalation or spray, rectally, or in the form of injectables.
  • injectable compositions may include intravenous, intramuscular, subcutaneous, and parenteral injections, as well as the use of infusion techniques.
  • Mirabegron (9.0 g) was suspended in a mixture of dimethyl sulphoxide (12 mL) and /-butyl acetate (100 mL). The reaction mixture was stirred at a temperature of about 25 °C to about 35°C for about 3 hours. The solid obtained was filtered, washed with t- butyl acetate (50 mL), and suck dried for about 30 minutes, then dried in a vacuum tray dryer at a temperature of about 25°C to about 35°C for about 3 hours to obtain the mirabegron dimethyl sulphoxide solvate.
  • Mirabegron dimethyl sulphoxide solvate 500 mg was dried at about 73°C to about 75°C under vacuum for about 6 hours to obtain the crystalline form of mirabegron.
  • Mirabegron dimethyl sulphoxide solvate 500 mg was dried at about 78°C to about 80°C under vacuum for about 3 hours to obtain the crystalline form of mirabegron.
  • Mirabegron dimethyl sulphoxide solvate 600 mg was dried at about 80°C under vacuum for about 6 hours to obtain the crystalline form of mirabegron.

Abstract

The present invention provides a crystalline form of mirabegron, a process for its preparation, a pharmaceutical composition comprising it, and its use for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.

Description

CRYSTALLINE FORM OF MIRABEGRON
Field of the Invention
The present invention provides a crystalline form of mirabegron, a process for its preparation, a pharmaceutical composition comprising it, and its use for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.
Background of the Invention
Mirabegron is a beta-3 adrenergic agonist disclosed in U.S. Patent No. 6,346,532. It is chemically designated as 2-(2-aminothiazol-4-yl)-N-[4-[2-{[(2R)-2-hydroxy-2- phenylethyl]amino}ethyl)phenyl]acetamide, having the structure depicted by Formula I.
Figure imgf000002_0001
Formula I
Polymorphs of mirabegron are disclosed in U.S. Patent No. 7,342,117; PCT Publication No. WO 2012/156998; and IP.com Disclosure No. IPCOM000228561D.
U.S. Patent No. 7,342,117 discloses a-Form and β-Form of mirabegron; PCT Publication No. WO 2012/156998 discloses an amorphous form of mirabegron; and IPCOM000228561D discloses crystalline forms of mirabegron and mirabegron monohydrochloride .
Summary of the Invention
The present invention provides a crystalline form of mirabegron, a process for its preparation, a pharmaceutical composition comprising it, and its use for the treatment of overactive bladder.
The crystalline form of mirabegron of the present invention is highly pure and free- flowing. It is stable towards polymorphic conversion and shows little or no variation in dissolution profile. A first aspect of the present invention provides a crystalline form of mirabegron characterized by an X-ray powder diffraction (XRPD) pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A.
A second aspect of the present invention provides a process for the preparation of a crystalline form of mirabegron of Formula I characterized by an XRPD pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A
Figure imgf000003_0001
Formula I
comprising desolvation of the mirabegron dimethyl sulphoxide solvate of Formula II.
Figure imgf000003_0002
Formula II
A third aspect of the present invention provides a pharmaceutical composition comprising a crystalline form of mirabegron characterized by an XRPD pattern having peaks at d-spacings of 5.74, 4.41, 4.28, 4.16, and 3.80 A and one or more
pharmaceutically acceptable carriers, diluents, or excipients.
A fourth aspect of the present invention provides use of a crystalline form of mirabegron, characterized by an X-ray powder diffraction having peaks at d-spacings of about 5.74, 4.41, 4.28, 4.16, and 3.80 A, for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.
Other objects, features, advantages, and aspects of the present invention will become apparent to those skilled in the art from the description provided herein.
Brief Description of the Figures
Figure 1 : X-Ray Powder Diffraction (XRPD) pattern of the crystalline form of mirabegron.
Figure 2: Differential Scanning Calorimetry (DSC) thermogram of the crystalline form of mirabegron. Figure 3 : Thermogravimetric Analysis (TGA) of the crystalline form of mirabegron.
Detailed Description of the Invention
Various embodiments and variants of the present invention are described hereinafter.
The term "contacting", as used herein, includes dissolving, mixing, slurrying, stirring, or combinations thereof.
The term "about", as used herein, refers to a variation of up to ±5% in the value of a parameter, such as temperature, stirring time, etc.
The crystalline form of mirabegron is characterized by an XRPD pattern having peaks at d-spacing of 5.74, 4.41, 4.28, 4.16, and 3.80 A.
The crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at d-spacing of 19.85, 7.17, 4.90, and 3.15 A.
The crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at 15.44, 20.13, 20.75, 21.36, and 23.44 ± 0.2 degrees 2Θ.
The crystalline form of mirabegron is further characterized by an XRPD pattern having peaks at 4.45, 12.34, 18.14, and 28.35 ± 0.2 degrees 2Θ.
Table 1 summarizes the d-spacing values in A, and the corresponding 2Θ values of the crystalline form of mirabegron of Formula I.
Table 1: XRPD peaks of a crystalline form of mirabegron
Figure imgf000005_0001
The crystalline form of mirabegron is further characterized by a DSC thermogram having endotherms at about 120.28°C and about 142.68°C. The crystalline form of mirabegron is further characterized by an XRPD pattern, a DSC thermogram, and a TGA as depicted in Figure 1, Figure 2, and Figure 3, respectively.
Mirabegron, which is used for the preparation of mirabegron dimethyl sulphoxide solvate, may be prepared by any method known in the art, such as those described in U.S. Patent No. 7,342,117 or PCT Publication No. WO 2012/156998, which are incorporated herein by reference.
The preparation of the mirabegron dimethyl sulphoxide solvate of Formula II is carried out by contacting mirabegron with dimethyl sulphoxide in the presence of a solvent at a temperature of about 20°C to the reflux temperature of the solvent. The solvent is selected from the group consisting of aromatic hydrocarbons, alkyl acetates, and mixtures thereof. Examples of aromatic hydrocarbons include toluene and xylene.
Examples of alkyl acetates include ethyl acetate, propyl acetate, and /-butyl acetate. The reaction mixture is stirred at a temperature of about 25 °C to about 35°C for about 1 hour to about 4 hours, filtered, washed with the solvent, and dried at a temperature of about 20°C to about 40°C for about 30 minutes to about 20 hours to provide mirabegron dimethyl sulphoxide solvate of Formula II.
The preparation of a crystalline form of mirabegron of Formula I characterized by XRPD peaks at d-spacing values of about 5.74, 4.41, 4.28, 4.16, and 3.80 A is carried out by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 70°C to about 80°C for about 2 hours to about 8 hours. Any suitable method of drying may be employed, such as drying under reduced pressure, vacuum tray drying, air drying, or combinations thereof.
In one embodiment of the present invention, the crystalline form of mirabegron is prepared by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 70°C to about 75 °C in a vacuum tray dryer for about 5 hours to about 6 hours.
In another embodiment of the present invention, the crystalline form of mirabegron is prepared by drying mirabegron dimethyl sulphoxide solvate of Formula II at about 75 °C to about 80°C in a vacuum tray dryer for about 2 hours to about 6 hours.
Solvates, pseudomorphs, and hydrates of the crystalline form of the present invention are also included within the scope of the present invention. The crystalline form of mirabegron of the present invention may be administered as part of a pharmaceutical composition for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency. Accordingly, in a further aspect, there is provided a pharmaceutical composition comprising the crystalline form of mirabegron of the present invention, one or more pharmaceutically acceptable carriers, diluents, or excipients, and optionally other therapeutic ingredients.
Pharmaceutical compositions comprising the crystalline form of mirabegron of the present invention may be administered orally, topically, parenterally, by inhalation or spray, rectally, or in the form of injectables. The injectable compositions may include intravenous, intramuscular, subcutaneous, and parenteral injections, as well as the use of infusion techniques.
In the foregoing section, embodiments are described by way of examples to illustrate the processes of invention. However, these are not intended in any way to limit the scope of the present invention. Variants of the examples that would be evident to persons ordinarily skilled in the art are within the scope of the present invention.
EXAMPLES
Example 1 : Preparation of mirabegron dimethyl sulphoxide solvate
Mirabegron (9.0 g) was suspended in a mixture of dimethyl sulphoxide (12 mL) and /-butyl acetate (100 mL). The reaction mixture was stirred at a temperature of about 25 °C to about 35°C for about 3 hours. The solid obtained was filtered, washed with t- butyl acetate (50 mL), and suck dried for about 30 minutes, then dried in a vacuum tray dryer at a temperature of about 25°C to about 35°C for about 3 hours to obtain the mirabegron dimethyl sulphoxide solvate.
Yield: 10.1 g
Example 2: Preparation of crystalline form of mirabegron
Method A:
Mirabegron dimethyl sulphoxide solvate (500 mg) was dried at about 73°C to about 75°C under vacuum for about 6 hours to obtain the crystalline form of mirabegron.
Yield: 0.38 g Method B:
Mirabegron dimethyl sulphoxide solvate (500 mg) was dried at about 78°C to about 80°C under vacuum for about 3 hours to obtain the crystalline form of mirabegron.
Yield: 0.38 g
Method C:
Mirabegron dimethyl sulphoxide solvate (600 mg) was dried at about 80°C under vacuum for about 6 hours to obtain the crystalline form of mirabegron.
Yield: 0.50 g

Claims

We claim:
1. A crystalline form of mirabegron characterized by an X-ray powder diffraction (XRPD) pattern having peaks at d-spacing values of 5.74, 4.41, 4.28, 4.16, and 3.80 A.
2. The crystalline form of mirabegron of claim 1, further characterized by an XRPD pattern having peaks at d-spacing values of 19.85, 7.17, 4.90, and 3.15 A.
3. The crystalline form of mirabegron of claim 1, further characterized by an XRPD pattern having peaks at values 15.44, 20.13, 20.75, 21.36, and 23.44 ± 0.2 degrees 2Θ.
4. The crystalline form of mirabegron of claim 1, further characterized by an XRPD pattern having peaks at 4.45, 12.34, 18.14, and 28.35 ± 0.2 degrees 2Θ.
5. The crystalline form of mirabegron of claim 1, characterized by an XRPD pattern substantially as depicted in Figure 1.
6. The crystalline form of mirabegron of claim 1, characterized by a DSC thermogram having endotherms at about 120.28°C and about 142.68°C.
7. The crystalline form of mirabegron of claim 1, characterized by a DSC thermogram substantially as depicted in Figure 2.
8. The crystalline form of mirabegron of claim 1, characterized by a TGA substantially as depicted in Figure 3.
9. A process for the preparation of a crystalline form of mirabegron characterized by an XRPD pattern having peaks at d-spacing values of 5.74, 4.41, 4.28, 4.16, and 3.80 A, compris
Figure imgf000009_0001
Formula II
10. The process according to claim 9, wherein the desolvation of mirabegron dimethyl sulphoxide solvate of Formula II is performed by drying at about 70°C to about 80°C.
11. The process according to claim 10, wherein the drying of the mirabegron dimethyl sulphoxide solvate of Formula II is carried out for about 2 hours to about 8 hours.
12. A pharmaceutical composition comprising a crystalline form of mirabegron characterized by an XRPD pattern having peaks at d-spacing of 5.74, 4.41, 4.28, 4.16, and 3.80 A and one or more pharmaceutically acceptable carriers, diluents, or excipients.
13. Use of the crystalline form of mirabegron, characterized by an X-ray powder diffraction having peaks at d-spacing values of 5.74, 4.41, 4.28, 4.16, and 3.80 A, for the treatment of overactive bladder with symptoms of urinary incontinence, urgency, and urinary frequency.
PCT/IB2014/064784 2013-09-23 2014-09-23 Crystalline form of mirabegron WO2015040605A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016049749A1 (en) * 2014-10-01 2016-04-07 Apotex Inc. Solid forms of mirabegron

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6346532B1 (en) 1997-10-17 2002-02-12 Yamanouchi Pharmaceutical Co., Ltd. Amide derivatives or salts thereof
EP1440969A1 (en) * 2001-10-30 2004-07-28 Yamanouchi Pharmaceutical Co. Ltd. Alpha-form or beta-form crystal of acetanilide derivative
WO2012156998A2 (en) 2011-05-18 2012-11-22 Dr. Reddy's Laboratories Limited Amorphous mirabegron and processes for crystal forms of mirabegron
WO2014132270A2 (en) * 2013-02-27 2014-09-04 Msn Laboratories Limited Process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-{[(2r)-2-hydroxy-2-phenyl ethyl]amino}ethyl)phenyl]acetamide monohydrochloride, its intermediates and polymorph thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6346532B1 (en) 1997-10-17 2002-02-12 Yamanouchi Pharmaceutical Co., Ltd. Amide derivatives or salts thereof
EP1440969A1 (en) * 2001-10-30 2004-07-28 Yamanouchi Pharmaceutical Co. Ltd. Alpha-form or beta-form crystal of acetanilide derivative
US7342117B2 (en) 2001-10-30 2008-03-11 Astellas Pharma Inc. α-form or β-form crystal of acetanilide derivative
WO2012156998A2 (en) 2011-05-18 2012-11-22 Dr. Reddy's Laboratories Limited Amorphous mirabegron and processes for crystal forms of mirabegron
WO2014132270A2 (en) * 2013-02-27 2014-09-04 Msn Laboratories Limited Process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-{[(2r)-2-hydroxy-2-phenyl ethyl]amino}ethyl)phenyl]acetamide monohydrochloride, its intermediates and polymorph thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"PREPARATION OF MIRABEGRON, IT'S INTERMEDIATES, A CRYSTALLINE FORM OF MIRABEGRON AND A CRYSTALLINE FORM OF MIRABEGRON MONOHYDROCHLO", IP.COM JOURNAL, IP.COM INC., WEST HENRIETTA, NY, US, 19 June 2013 (2013-06-19), XP013157840, ISSN: 1533-0001 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016049749A1 (en) * 2014-10-01 2016-04-07 Apotex Inc. Solid forms of mirabegron

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