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WO2009151899A2 - Préparation de mésylate d’imatinib - Google Patents

Préparation de mésylate d’imatinib Download PDF

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Publication number
WO2009151899A2
WO2009151899A2 PCT/US2009/044587 US2009044587W WO2009151899A2 WO 2009151899 A2 WO2009151899 A2 WO 2009151899A2 US 2009044587 W US2009044587 W US 2009044587W WO 2009151899 A2 WO2009151899 A2 WO 2009151899A2
Authority
WO
WIPO (PCT)
Prior art keywords
imatinib mesylate
alpha
imatinib
crystalline
ether
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2009/044587
Other languages
English (en)
Other versions
WO2009151899A3 (fr
Inventor
Rajasekhar Kadaboina
Munaswamy Sekhar Nariyam
Vijay Bhailalbhai Patel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
Original Assignee
Dr Reddys Laboratories Ltd
Dr Reddys Laboratories Inc
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 Dr Reddys Laboratories Ltd, Dr Reddys Laboratories Inc filed Critical Dr Reddys Laboratories Ltd
Priority to EP09763190A priority Critical patent/EP2291366A4/fr
Publication of WO2009151899A2 publication Critical patent/WO2009151899A2/fr
Publication of WO2009151899A3 publication Critical patent/WO2009151899A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • the present application relates to a crystalline polymorphic form of imatinib mesylate.
  • Imatinib mesylate has a chemical name 4-[(4-Methyl-1-piperazinyl)methyl]- N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide methanesulfonate and can be represented by structural Formula I.
  • Imatinib is a protein-tyrosine kinase inhibitor and is available in products sold by Novartis using the trademark GLEEVEC, in the form of tablets containing imatinib mesylate equivalent to 100 mg or 400 mg of imatinib free base.
  • Zimmermann et al. in U.S. Patent No. 6,894,051 , describe two crystalline forms of imatinib mesylate, the alpha-form and the beta-form.
  • the patent also discloses that the crystalline alpha-form is characterized by needle-shaped crystals having a hygroscopic nature and "the crystals are not particularly well- suited to pharmaceutical formulation as solid dosage forms, because their physical properties, for example their flow characteristics, are unfavorable and the alpha-crystal form is metastable at room temperature.
  • Example 1 of the patent discloses a process for preparing the crystalline alpha-form, which comprises: a. Suspending imatinib base in ethanol solvent; b. Adding methanesulfonic acid drop-wise into the suspension; c. Heating the solution to reflux and filtering at 65°C; d. Evaporating the filtrate to 50% of the volume; e. Cooling to 25°C and filtering; f. Collecting the solid (material A); g. Evaporating the mother liquor (filtrate) to dryness; h.
  • This process disclosed for preparing alpha crystalline form not only involves several steps, but also is cumbersome and does not give reproducible results.
  • Process 1 comprises:
  • Process 2 comprises:
  • Adin et al. in U.S. Patent Application Publication No. 2006/0223816 A1 ('"816" publication), describe a stable, free-flowing imatinib mesylate alpha-form, which is substantially free of the beta-form.
  • This publication describes a process, which comprises: a. Mixing imatinib base with an organic solvent selected from ketones, nithles and cycloalkanes (more particularly methyl ethyl ketone, methyl isobutyl ketone, 4-methylcyclohexanone, cyclohexane, acetonithle and mixtures thereof); b. Heating to dissolve; c. Adding methanesulfonic acid; d. Allowing the crystals to precipitate; e. Isolating the precipitated crystal of imatinib mesylate alpha-form, with seeding.
  • an organic solvent selected from ketones, nithles and cycloalkanes (more particularly
  • the present invention provides processes for preparing a non-hygroscopic, stable crystalline alpha-form of imatinib mesylate, comprising: a. Providing a solution or suspension of imatinib base in an ether solvent; b. Optionally, seeding with imatinib mesylate in alpha-form; c. Adding methanesulfonic acid; d. Allowing the reaction mass to cool; and e. Obtaining the alpha-form imatinib mesylate.
  • the present invention provides pharmaceutical compositions comprising stable crystalline alpha-form imatinib mesylate and at least one pharmaceutically acceptable excipient.
  • Fig. 1 is an X-Ray powder diffraction ("XRPD") pattern of the alpha-form of imatinib mesylate prepared according to Example 1.
  • Fig. 2 is an infrared (“IR”) absorption spectrum of the alpha-form of imatinib mesylate prepared according to Example 1.
  • Fig. 3 is a differential scanning calorimetry ("DSC") curve of the alpha-form of imatinib mesylate prepared according to Example 1.
  • Fig. 4 is a thermogravimetric analysis (“TGA”) curve of the alpha-form of imatinib mesylate prepared according to Example 1.
  • Fig. 5 is an XRPD pattern of the alpha-form of imatinib mesylate prepared according to Example 2.
  • Fig. 6 is an XRPD pattern of the alpha-form of imatinib mesylate of the present invention after one year of storage under ambient conditions.
  • Fig. 7 is an infrared (“IR”) absorption spectrum of imatinib mesylate of the present invention after one year of storage under ambient conditions.
  • Fig. 8 is a TGA curve of the alpha-form of imatinib mesylate of the present invention after one year of storage under ambient conditions.
  • Fig. 9 is a DSC curve of the alpha-form of imatinib mesylate of the present invention after one year of storage under ambient conditions.
  • Fig.10 is a TGA curve of the alpha-form of imatinib mesylate prepared according to Example 3.
  • the present application provides processes for preparing a stable crystalline alpha-form imatinib mesylate, using solvents comprising cyclic ethers and acyclic ethers.
  • crystalline alpha-form imatinib mesylate may be prepared from solvents comprising cyclic ethers and acyclic ethers, giving a product that is not only stable, but also non-hygroscopic, convenient to handle, and suitable for use in preparing solid pharmaceutical formulations.
  • the processes of the present invention include crystallizing imatinib mesylate from a solution having solvents comprising cyclic ethers and acyclic ethers, with imatinib and methanesulfonic acid dissolved therein, and optionally seeding with crystals of imatinib mesylate in alpha-form.
  • processes for preparing a non-hygroscopic and stable crystalline alpha-form imatinib mesylate comprising: a. providing a solution or suspension of imatinib base in an ether solvent; b. optionally, seeding with imatinib mesylate in alpha-form; c. adding methanesulfonic acid; and d. allowing the reaction mass to cool.
  • Step a includes providing a solution or suspension of imatinib base in an ether solvent.
  • the process of suspending the imatinib base in an ether solvent comprises combining imatinib base with the solvent.
  • the suspension of imatinib base may also be obtained directly from a reaction in which imatinib base is synthesized.
  • Solvents which may be used for suspending imatinib base include but are not limited to cyclic ethers and acyclic ethers. Specific examples of solvents that may be utilized for the present invention include cyclic ethers such as tetrahydrofuran ("THF"), pentahydropyran, and the like, and acyclic ether solvents such as dimethyl ether, diethyl ether, methyl t-butyl ether, and the like.
  • THF tetrahydrofuran
  • pentahydropyran and the like
  • acyclic ether solvents such as dimethyl ether, diethyl ether, methyl t-butyl ether, and the like.
  • the temperatures to which the suspension of imatinib base in a solvent can be heated may range from about 25°C to about 100 0 C, depending on the solvent used.
  • the suspension of imatinib mesylate in a solvent may also result in a solution, depending on the temperature to which it is heated.
  • the process of the present invention is carried out at temperatures in the range of about 40-70 0 C.
  • the quantities of solvent used for providing the suspension or solution depend on the solvent and the temperature adopted.
  • the concentration of imatinib base in the suspension may generally range from about 0.03 to about 0.1 g/mL.
  • seeding with imatinib mesylate is optional.
  • the alpha crystalline form obtained from a process disclosed in the art or from the process of the present invention may be used as a seed material.
  • Seeding with crystalline alpha form imatinib mesylate is carried out before or after the addition of methanesulfonic acid and after providing a solution or suspension of imatinib base in the ether solvent. In an embodiment, seeding with crystalline alpha-form of imatinib mesylate is carried out before the addition of methanesulfonic acid.
  • the quantity of the seed crystals used herein may be in the range of about 1 -8% by weight of alpha-form seeding material, based on the weight of suspended imatinib free base.
  • Step c includes adding methanesulfonic acid.
  • Isolation of the crystalline alpha-form obtained in step d can be accomplished by techniques known in art, which include but are not limited to decantation, filtration by gravity or by suction, distillation, centhfuging, slow solvent evaporation, and the like.
  • the obtained alpha-form of the present invention is isolated by filtration.
  • the isolated solid may optionally be further dried. Drying may be suitably carried out using equipment such as a tray dryer, vacuum oven, air oven, fluidized bed dryer, spin flash dryer, flash dryer and the like. The drying may be carried out at temperatures about 35°C to about 90 0 C, with or without vacuum. Drying may be carried out for any desired time until the desired product purity is achieved, such as time periods from about 1 to 20 hours, or longer.
  • the solid obtained is dried at temperatures ranging from about 30°C to about 60°C, or at temperatures about 40 0 C to about 45°C, under vacuum for a period of 2-3 hours.
  • Embodiments of the process provide imatinib mesylate alpha-form having a purity, as determined using high performance liquid chromatograpgy, at least about 98%, at least about 99%, at least about 99.5%, or at least about 99.8%, by weight.
  • the present invention provides processes for preparing substantially anhydrous crystalline alpha-form imatinib mesylate, comprising slurrying imatinib mesylate in a hydrocarbon solvent, followed by isolating the solid and drying.
  • the substantially anhydrous crystalline alpha-form imatinib mesylate obtained by the process has a TGA weight loss (from ambient temperature to about 150 0 C, or to about 200 0 C) less than about 0.5%, which may include water content and other volatile substances that are present.
  • a substantially anhydrous crystalline alpha-form imatinib mesylate has a TGA weight loss less than about 0.2%, or less than about 0.1 %.
  • a crystalline alpha-form of imatinib mesylate obtained according to the processes of the present invention when packaged in a polyethylene bag that is sealed and placed inside another sealed polyethylene bag, is stable during storage at ambient temperature for at least about one year.
  • Stored crystalline alpha-form of imatinib mesylate of the present invention can be characterized by any one or more of: an XRPD diffraction pattern substantially in accordance with Fig. 6; a TGA curve substantially in accordance with Fig. 8; and a DSC curve substantially in accordance with Fig. 9.
  • crystalline alpha-form of imatinib mesylate obtained from a process of present invention has a particle size distribution with Di 0 less than about 10 ⁇ m, D 50 less than about 50 ⁇ m, and D 90 less than about 100 ⁇ m.
  • the formed crystals are filtered and dried under vacuum for about 14 hours at 40-45 0 C, to obtain 68.415 g of crystalline alpha- form imatinib mesylate having a purity of about 99.91 % by weight, as determined using high performance liquid chromatography.
  • the product obtained has the X- ray powder diffraction pattern shown in Fig. 1.
  • the product is also analyzed by IR spectrophotometry, DSC, and TGA, and the information obtained is shown in Figs. 2, 3, and 4, respectively.
  • EXAMPLE 2 PREPARATION OF CRYSTALLINE ALPHA-FORM IMATINIB MESYLATE.
  • Imatinib base (1.0 g) is added to THF (25 mL) and heated to about 55-60°C under a nitrogen atmosphere.
  • a solution of methanesulfonic acid (0.13 mL, 0.192 g) in THF (15 mL) is added slowly over 3 hours under a nitrogen atmosphere.
  • the mass is stirred for another 30 minutes at 55-60 0 C and cooled to 25°C.
  • the formed crystals are filtered and dried under vacuum for 1 hour at 40-45 0 C, to obtain 0.950 g of crystalline alpha-form imatinib mesylate.
  • the product obtained has the X-ray powder diffraction pattern shown in Fig. 5.
  • the crystalline alpha-form of imatinib mesylate obtained in the above example is stable during storage for at least one year, when packaged in a sealed polyethylene bag, and the X-ray powder diffraction pattern for material stored for one year is substantially as shown in Fig. 6.
  • the stored material provides an infrared absorption spectrum substantially as shown in Fig. 7, a thermogravimetric analysis curve substantially as shown in Fig. 8 (weight loss about 1 %) and a differential scanning calorimetry curve substantially as shown in Fig. 9 (major peak at about 220 0 C).
  • Alpha-form imatinib mesylate (5.0 g) is suspended in n-heptane (62.5 mL) and slurried for 45 minutes at room temperature under a nitrogen atmosphere. The suspension is filtered and the solid washed with n-heptane (12 mL). The solid is dried under vacuum for 3 hours at 40-45°C, to obtain 4.9 g of light yellow solid crystalline alpha-form imatinib mesylate that is substantially anhydrous. Analyses are reported in the following table. The TGA curve for the product is substantially as shown in Fig. 10.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne des procédés permettant de préparer un mésylate d’imatinib de forme cristalline alpha non hygroscopique et stable.
PCT/US2009/044587 2008-05-26 2009-05-20 Préparation de mésylate d’imatinib Ceased WO2009151899A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09763190A EP2291366A4 (fr) 2008-05-26 2009-05-20 Préparation de mésylate d imatinib

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1285CH2008 2008-05-26
IN1285/CHE/2008 2008-05-26
US9800308P 2008-09-18 2008-09-18
US61/098,003 2008-09-18

Publications (2)

Publication Number Publication Date
WO2009151899A2 true WO2009151899A2 (fr) 2009-12-17
WO2009151899A3 WO2009151899A3 (fr) 2010-02-25

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EP (1) EP2291366A4 (fr)
WO (1) WO2009151899A2 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011108953A1 (fr) * 2010-03-04 2011-09-09 Tomasz Kozluk Procédé pour la préparation de forme polymorphe α et nouvelle forme polymorphe d'imatinib mésylate isolée dans ce procédé
WO2011158255A1 (fr) * 2010-06-16 2011-12-22 Aptuit Laurus Private Limited Procédé pour la préparation de forme alpha de mésylate d'imatinib stable
WO2011157450A1 (fr) 2010-06-18 2011-12-22 Krka, D. D., Novo Mesto Nouvelle forme polymorphique d'imatinib base et préparation de ses sels
WO2012014000A1 (fr) * 2010-07-30 2012-02-02 Ramesh Babu Potluri Forme cristalline α stable de mésylate d'imatinib et son procédé de synthèse
WO2012071980A1 (fr) * 2010-11-30 2012-06-07 浙江九洲药业股份有限公司 Procédé de préparation d'un mésylate de α-imatinib
WO2012015999A3 (fr) * 2010-07-29 2012-08-30 Dr. Reddy's Laboratories Ltd. Procédé de préparation de mésylate d'imatinib
EP2546247A1 (fr) 2011-07-14 2013-01-16 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Procédure de préparation de mésylate d'imatinib
WO2013136141A1 (fr) 2012-03-13 2013-09-19 Fresenius Kabi Oncology Ltd. Procédé amélioré pour la préparation de la forme alpha de mésylate d'imatinib
EP2749557A1 (fr) 2012-12-31 2014-07-02 Deva Holding Anonim Sirketi Procédé de préparation d'alpha forme polymorphe de mesylate d'imatinib de isopropanol et THF solvatés de mésylate d'imatinib
US8912325B2 (en) 2011-03-31 2014-12-16 Ind-Swift Laboratories Limited Process for preparation of imatinib and its mesylate salt
EP2927223A1 (fr) 2014-04-04 2015-10-07 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Procédé de préparation de l'imatinib et de ses sels, exempt d'impureté génotoxique f
EP3007699A4 (fr) * 2013-06-12 2017-01-18 Shilpa Medicare Limited Procédé de préparation de mésylate d'imatinib cristallin

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7300938B2 (en) * 2003-06-02 2007-11-27 Hetero Drugs Limited Polymorphs of imatinib mesylate
KR101348625B1 (ko) * 2004-09-02 2014-01-07 씨아이피엘에이 엘티디. 이매티닙 메실레이트의 안정한 결정형 및 그의 제조방법
US8067421B2 (en) * 2006-04-27 2011-11-29 Sicor Inc. Polymorphic forms of imatinib mesylate and processes for preparation of novel crystalline forms as well as amorphous and form α
US20060223816A1 (en) * 2006-05-08 2006-10-05 Chemagis Ltd. Imatinib mesylate alpha form and production process therefor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2291366A4 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011108953A1 (fr) * 2010-03-04 2011-09-09 Tomasz Kozluk Procédé pour la préparation de forme polymorphe α et nouvelle forme polymorphe d'imatinib mésylate isolée dans ce procédé
WO2011158255A1 (fr) * 2010-06-16 2011-12-22 Aptuit Laurus Private Limited Procédé pour la préparation de forme alpha de mésylate d'imatinib stable
WO2011157450A1 (fr) 2010-06-18 2011-12-22 Krka, D. D., Novo Mesto Nouvelle forme polymorphique d'imatinib base et préparation de ses sels
EA024088B1 (ru) * 2010-06-18 2016-08-31 КРКА, д.д., НОВО МЕСТО α-ФОРМА МЕЗИЛАТА ИМАТИНИБА, СПОСОБЫ ЕЕ ПОЛУЧЕНИЯ И СОДЕРЖАЩАЯ ЕЁ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ
WO2012015999A3 (fr) * 2010-07-29 2012-08-30 Dr. Reddy's Laboratories Ltd. Procédé de préparation de mésylate d'imatinib
WO2012014000A1 (fr) * 2010-07-30 2012-02-02 Ramesh Babu Potluri Forme cristalline α stable de mésylate d'imatinib et son procédé de synthèse
US8871930B2 (en) 2010-11-30 2014-10-28 Zhejiang Jiuzhou Pharma Science & Technology Co., Ltd. Preparation method of alpha-imatinib mesylate
WO2012071980A1 (fr) * 2010-11-30 2012-06-07 浙江九洲药业股份有限公司 Procédé de préparation d'un mésylate de α-imatinib
US8912325B2 (en) 2011-03-31 2014-12-16 Ind-Swift Laboratories Limited Process for preparation of imatinib and its mesylate salt
EP2546247A1 (fr) 2011-07-14 2013-01-16 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Procédure de préparation de mésylate d'imatinib
WO2013136141A1 (fr) 2012-03-13 2013-09-19 Fresenius Kabi Oncology Ltd. Procédé amélioré pour la préparation de la forme alpha de mésylate d'imatinib
EP2749557A1 (fr) 2012-12-31 2014-07-02 Deva Holding Anonim Sirketi Procédé de préparation d'alpha forme polymorphe de mesylate d'imatinib de isopropanol et THF solvatés de mésylate d'imatinib
EP3007699A4 (fr) * 2013-06-12 2017-01-18 Shilpa Medicare Limited Procédé de préparation de mésylate d'imatinib cristallin
EP2927223A1 (fr) 2014-04-04 2015-10-07 F.I.S.- Fabbrica Italiana Sintetici S.p.A. Procédé de préparation de l'imatinib et de ses sels, exempt d'impureté génotoxique f

Also Published As

Publication number Publication date
EP2291366A4 (fr) 2012-06-06
EP2291366A2 (fr) 2011-03-09
WO2009151899A3 (fr) 2010-02-25

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