WO2013179194A1 - Procédé de préparation de dexlansoprazole cristallin - Google Patents

Procédé de préparation de dexlansoprazole cristallin Download PDF

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Publication number
WO2013179194A1
WO2013179194A1 PCT/IB2013/054279 IB2013054279W WO2013179194A1 WO 2013179194 A1 WO2013179194 A1 WO 2013179194A1 IB 2013054279 W IB2013054279 W IB 2013054279W WO 2013179194 A1 WO2013179194 A1 WO 2013179194A1
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WO
WIPO (PCT)
Prior art keywords
dexlansoprazole
process according
ether
methyl
mixtures
Prior art date
Application number
PCT/IB2013/054279
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English (en)
Inventor
Bhavin Prabhudas Thanki
Mahavir Singh Khanna
Rajesh Kumar Thaper
Mohan Prasad
Sudershan Kumar Arora
Original Assignee
Ranbaxy Laboratories Limited
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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Publication of WO2013179194A1 publication Critical patent/WO2013179194A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a process for the preparation of crystalline dexlansoprazole.
  • Dexlansoprazole is chemically described as 2-[(R)- ⁇ [3-methyl-4-(2,2,2- trifluoroethoxy)pyridin-2-yl]methyl ⁇ sulfinyl]- lH-benzimidazole as represented by Formula I.
  • Dexlansoprazole is indicated for healing all grades of erosive esophagitis (EE) for up to 8 weeks, maintenance of healing of EE for up to 6 months, and treatment of heartburn associated with non-erosive gastroesophageal reflux disease (GERD) for 4 weeks.
  • EE erosive esophagitis
  • GFD gastroesophageal reflux disease
  • PCT Publication No. WO 2010/095144 describes the process for the preparation of crystalline dexlansoprazole using ketone and hydrocarbon solvent mixtures.
  • the present inventors have found that the crystalline dexlansoprazole prepared by using an acetone and heptane mixture is not stable, as the color of this material deteriorates during storage.
  • the present inventors have found that crystalline dexlansoprazole prepared by using an acetone and heptane mixture is not stable, as the color of this material deteriorates during storage.
  • the present inventors have found that crystalline dexlansoprazole prepared by using an acetone and heptane mixture is not stable, as the color of this material deteriorates during storage.
  • the present inventors have found that crystalline dexlansoprazole prepared by using an acetone and heptane mixture is not stable, as the color of this material deteriorates during storage.
  • the present inventors have found that crystalline dexlansoprazole prepared by using an acetone and heptane mixture is not stable, as the color of this material deteriorates during storage.
  • dexlansoprazole can be prepared as a stable material with both the color and consistency of the material remaining stable on storage.
  • the present invention provides a simple, efficient, and industrially preferable process for the preparation of crystalline
  • An aspect of the present invention provides a process for the preparation of crystalline dexlansoprazole, which comprises:
  • step b) treating the mixture obtained in step a) with aliphatic hydrocarbons, cyclic aliphatic hydrocarbons, ethers, or mixtures thereof;
  • the dexlansoprazole used as a starting material may be in any solid form and may be prepared according to the methods described in U.S. Patent No. 7,271,182, PCT Publication No. WO 201 1/121548, or PCT Publication No. WO 201 1/121546.
  • the dexlansoprazole is treated with a solvent selected from the group consisting of cyclic ethers, C 4 -6 ketones, or mixtures thereof.
  • the cyclic ether is selected from the group comprising tetrahydrofuran, 2-methyl tetrahydrofuran, 2,4-dimethyl tetrahydrofuran, or mixtures thereof.
  • the cyclic ether used is tetrahydrofuran or 2-methyl tetrahydrofuran.
  • the C 4 _6 ketone is selected from the group comprising methyl ethyl ketone, methyl isopropyl ketone, or mixtures thereof.
  • the C 4 -6 ketone used is methyl ethyl ketone.
  • the dexlansoprazole may be optionally treated with ammonia or organic amines.
  • the organic amine may be, for example, diisopropylethylamine.
  • the treatment of dexlansoprazole with the cyclic ether or C 4 _6 ketone may be carried out at a temperature of about 15°C to about 50°C, for example, about 25°C to about 30°C.
  • the treatment of dexlansoprazole with cyclic ether or C 4 _6 ketone may be carried out for 10 minutes to 60 minutes, preferably 20 minutes to 40 minutes.
  • the reaction mixture may be treated with aliphatic hydrocarbons, cyclic aliphatic hydrocarbons, ethers, or mixtures thereof.
  • the aliphatic hydrocarbon in step b) is selected from the group comprising pentane, n-heptane, hexane, or mixtures thereof. In a preferred embodiment of the present invention, the aliphatic hydrocarbon used is n-heptane.
  • the cyclic aliphatic hydrocarbon in step b) is selected from the group comprising cyclohexane, cycloheptane, or mixtures thereof. In a preferred embodiment of the present invention, the cyclic aliphatic hydrocarbon used is cyclohexane.
  • the ether in step b) is selected from the group comprising methyl tertiary butyl ether, cyclopropyl methyl ether, cyclobutyl methyl ether, diisopropyl ether, or mixtures thereof.
  • the ether used is methyl tertiary butyl ether or cyclopropyl methyl ether.
  • the treatment of the reaction mixture with the aliphatic hydrocarbons, cyclic aliphatic hydrocarbons, ethers, or mixtures thereof is carried out at a temperature of about 15°C to about 50°C, preferably, about 25°C to about 35°C, for about 2 hours to about 7 hours, preferably for about 4 hours to about 5 hours
  • the crystalline dexlansoprazole may be isolated by filtration, distillation, decantation, vacuum drying, evaporation, or a combination thereof.
  • Figure 1 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 1.
  • Figure 1 A provides the table of values for the XRPD pattern depicted in Figure 1.
  • Figure 2 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 2.
  • Figure 2A provides the table of values for the XRPD pattern depicted in Figure 2.
  • Figure 3 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 3.
  • Figure 3 A provides the table of values for the XRPD pattern depicted in Figure 3.
  • Figure 4 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 4.
  • Figure 4A provides the table of values for the XRPD pattern depicted in Figure 4.
  • Figure 5 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 5.
  • Figure 5 A provides the table of values for the XRPD pattern depicted in Figure 5.
  • Figure 6 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 6.
  • Figure 6A provides the table of values for the XRPD pattern depicted in Figure 6.
  • Figure 7 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 7.
  • Figure 7A provides the table of values for the XRPD pattern depicted in Figure 7.
  • Figure 8 depicts the X-ray powder diffraction pattern (XRPD) of the crystalline dexlansoprazole obtained according to Example 8.
  • Figure 8 A provides the table of values for the XRPD pattern depicted in Figure 8.
  • XRPD of the samples were determined by using Panalytical X'Pert Pro X-Ray Powder Diffractometer in the range 3-40 degree 2 theta and under tube voltage and current of 45 Kv and 40 mA respectively.
  • the copper radiation of wavelength 1.54 angstroms and an Xceletor detector were used.
  • Tetrahydrofuran 100 mL was added to dexlansoprazole (50 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes.
  • Tetrahydrofuran 100 mL was added to dexlansoprazole (50 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes.
  • n-Heptane 1000 mL was added to the reaction mixture at 25°C to 30°C over 1.5 hours to 2 hours. The reaction mixture was stirred at 25°C to 30°C for 2 hours. The reaction mixture was filtered and washed with n-heptane (100 mL) under nitrogen at 25°C to 30°C. The solid obtained was dried under vacuum at 30°C to 32°C for 8 hours to 12 hours to obtain the title compound having an XRPD pattern as depicted in Figure 3.
  • Methyl ethyl ketone (80 mL) was added to dexlansoprazole (20 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes. n-Heptane (80 mL) was added to the reaction mixture at 25°C to 30°C over 45 minutes. The reaction mixture was stirred at 25°C to 30°C for 2 hours. The reaction mixture was filtered and washed with n-heptane (40 mL) under nitrogen at 25°C to 30°C. The solid obtained was dried under vacuum at 30°C to 32°C for 8 hours to 12 hours to obtain the title compound having an XRPD pattern as depicted in Figure 5.
  • Tetrahydrofuran (30 mL) was added to dexlansoprazole (15 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes.
  • Methyl ethyl ketone (40 mL) was added to dexlansoprazole (10 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes.
  • Tetrahydrofuran (30 mL) was added to dexlansoprazole (15 g) at 25°C to 30°C. The reaction mixture was stirred at 25°C to 30°C for 10 minutes to 15 minutes. Methyl tertiary butyl ether (150 mL) was added to the reaction mixture at 25°C to 30°C in one lot. The reaction mixture was stirred at 25°C to 30°C for 5 hours. The reaction mixture was filtered and washed with methyl tertiary butyl ether (30 mL) under nitrogen at 25°C to 30°C. The solid obtained was dried under vacuum at 30°C to 32°C for 8 hours to 12 hours to obtain the title compound having an XRPD pattern as depicted in Figure 8.

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

Abstract

Cette invention concerne un procédé de préparation de dexlansoprazole cristallin.
PCT/IB2013/054279 2012-05-31 2013-05-23 Procédé de préparation de dexlansoprazole cristallin WO2013179194A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1667DE2012 2012-05-31
IN1667/DEL/2012 2012-05-31

Publications (1)

Publication Number Publication Date
WO2013179194A1 true WO2013179194A1 (fr) 2013-12-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106279107A (zh) * 2016-08-10 2017-01-04 成都尚药科技有限公司 一种右旋兰索拉唑晶型的制备方法

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6462058B1 (en) 1999-06-17 2002-10-08 Takeda Chemical Industries, Ltd. Benzimidazole compound crystal
US20070004779A1 (en) 2000-05-15 2007-01-04 Hideo Hashimoto Process for producing crystal
US7271182B2 (en) 2000-08-04 2007-09-18 Takeda Pharmaceutical Company Limited Salts of benzimidazole compound and use thereof
US7285668B2 (en) 2000-12-01 2007-10-23 Takeda Pharmaceutical Company Limited Process for the crystallization of (R)- or (S)-lansoprazole
WO2009117489A1 (fr) 2008-03-18 2009-09-24 Dr. Reddy's Laboratories Ltd. Procédé de préparation du dexlansoprazole et autres formes polymorphes
WO2010039885A2 (fr) * 2008-09-30 2010-04-08 Teva Pharmaceutical Industries Ltd. Formes cristallines du dexlansoprazole
WO2010095144A2 (fr) 2009-02-04 2010-08-26 Msn Laboratories Limited Procédé de préparation d'inhibiteurs de pompe à protons
US20110028728A1 (en) * 2009-07-29 2011-02-03 Dipharma Francis S.R.L. Process for the preparation of crystalline dexlansoprazole
WO2011092665A1 (fr) * 2010-01-29 2011-08-04 Ranbaxy Laboratories Limited Procédé pour la préparation de formes cristallines de dexlansoprazole
WO2011098938A1 (fr) * 2010-02-11 2011-08-18 Orchid Chemicals And Pharmaceuticals Limited Nouveau solvate du dexlansoprazole
WO2011121546A1 (fr) 2010-03-31 2011-10-06 Ranbaxy Laboratories Limited Sels de dexlansoprazole et leur élaboration
WO2011121548A1 (fr) 2010-03-31 2011-10-06 Ranbaxy Laboratories Limited Procédé d'élaboration de dexlansoprazole
WO2011139414A2 (fr) * 2010-04-27 2011-11-10 Dr. Reddy's Laboratories Ltd. Formes polymorphes de dexlansoprazole

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6462058B1 (en) 1999-06-17 2002-10-08 Takeda Chemical Industries, Ltd. Benzimidazole compound crystal
US20070004779A1 (en) 2000-05-15 2007-01-04 Hideo Hashimoto Process for producing crystal
US7271182B2 (en) 2000-08-04 2007-09-18 Takeda Pharmaceutical Company Limited Salts of benzimidazole compound and use thereof
US7285668B2 (en) 2000-12-01 2007-10-23 Takeda Pharmaceutical Company Limited Process for the crystallization of (R)- or (S)-lansoprazole
WO2009117489A1 (fr) 2008-03-18 2009-09-24 Dr. Reddy's Laboratories Ltd. Procédé de préparation du dexlansoprazole et autres formes polymorphes
WO2010039885A2 (fr) * 2008-09-30 2010-04-08 Teva Pharmaceutical Industries Ltd. Formes cristallines du dexlansoprazole
WO2010095144A2 (fr) 2009-02-04 2010-08-26 Msn Laboratories Limited Procédé de préparation d'inhibiteurs de pompe à protons
US20110028728A1 (en) * 2009-07-29 2011-02-03 Dipharma Francis S.R.L. Process for the preparation of crystalline dexlansoprazole
WO2011092665A1 (fr) * 2010-01-29 2011-08-04 Ranbaxy Laboratories Limited Procédé pour la préparation de formes cristallines de dexlansoprazole
WO2011098938A1 (fr) * 2010-02-11 2011-08-18 Orchid Chemicals And Pharmaceuticals Limited Nouveau solvate du dexlansoprazole
WO2011121546A1 (fr) 2010-03-31 2011-10-06 Ranbaxy Laboratories Limited Sels de dexlansoprazole et leur élaboration
WO2011121548A1 (fr) 2010-03-31 2011-10-06 Ranbaxy Laboratories Limited Procédé d'élaboration de dexlansoprazole
WO2011139414A2 (fr) * 2010-04-27 2011-11-10 Dr. Reddy's Laboratories Ltd. Formes polymorphes de dexlansoprazole

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106279107A (zh) * 2016-08-10 2017-01-04 成都尚药科技有限公司 一种右旋兰索拉唑晶型的制备方法

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