WO2006054314A1 - Formes polymorphes de mesylate d'imatinibe - Google Patents

Formes polymorphes de mesylate d'imatinibe Download PDF

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Publication number
WO2006054314A1
WO2006054314A1 PCT/IN2005/000273 IN2005000273W WO2006054314A1 WO 2006054314 A1 WO2006054314 A1 WO 2006054314A1 IN 2005000273 W IN2005000273 W IN 2005000273W WO 2006054314 A1 WO2006054314 A1 WO 2006054314A1
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WIPO (PCT)
Prior art keywords
pharmaceutical composition
imatinib mesylate
composition
cellulose
sodium
Prior art date
Application number
PCT/IN2005/000273
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English (en)
Inventor
Amala Kishan Kompella
Bhujanga Rao Adibhatla Kali Satya
Khadgapathi Podili
Nannapaneni Venkaiah Chowdary
Original Assignee
Natco Pharma Limited
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Publication date
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Publication of WO2006054314A1 publication Critical patent/WO2006054314A1/fr

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents

Definitions

  • the present invention relates to novel crystalline Form I and Form II of imatinib mesylate and processes for the preparation of the said Forms.
  • Imatinib mesylate has the formula given below.
  • the invention also relates to pharmaceutical composition containing the novel crystalline Forms I & II of imatinib mesylate.
  • Imatinib mesylate which is N- ⁇ 5-[4-(4-mehylpiperizino methyl)-benzoylamido]-2- methylphenyl ⁇ -4-(3-pyridinyl)-2-pyrimidine amine having the formula I given above is approved under the trademark" Gleevec" by the US Food and Drug Administration for the treatment of chronic myelogenous leukemia after the failure of Interferon Alpha. It has also been approved for the treatment of patients with kit [CD 117] positive unresectable and/or metastatic malignant Gastro Intestinal Stromal Tumors (GISTS).
  • GISTS Gastro Intestinal Stromal Tumors
  • Important solid-state properties of a pharmaceutical substance are its rate of dissolution in aqueous fluid.
  • the rate of dissolution of an active ingredient in a patient's stomach fluid may have therapeutic consequences because it imposes an upper limit on the rate at which an orally administered active ingredient may reach the blood stream.
  • the solid- state form of a compound may also affect its behavior on compaction and its storage stability.
  • the polymorphic form may give rise to thermal behavior different form that of the amorphous material (or) another polymorphic form.
  • Thermal behavior is measured in the laboratory by such techniques as capillary melting point, Thermo Gravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC), and may be used to distinguish some polymorphic forms from others.
  • TGA Thermo Gravimetric Analysis
  • DSC Differential Scanning Calorimetry
  • a particular polymorphic form may also give rise to distinct properties that may be detectable by X-Ray Powder Diffraction (XRPD) solid-state 13 CNMR spectrometry and infrared spectrometry.
  • XRPD X-Ray Powder Diffraction
  • the various characteristics and properties of the polymorphic forms of a substance E.g. shape, color, density and the like, will make one polymorphic form preferable over the others for production and /or pharmaceutical compounding.
  • a very first step in the processes of product development of a new pharmaceutical agent is the determination of whether it exists in polymorphic forms and if so which of such form possesses advantages for the eventual commercial pharmaceutical application.
  • ⁇ form is offered commercially under the trade name Gleevec ® / Glivec®
  • the discovery of new polymorphic forms of a pharmaceutically useful compound provides a new opportunity to improve the performance characteristics of a pharmaceutical product. It enlarges the repertoire of materials that a formulation scientist has available for designing, for example, a pharmaceutical dosage form of a drug with a targeted release profile or other desired characteristic.
  • the main objective of the present invention is to provide novel crystalline polymorphic Forms I & II of Imatinib mesyalte
  • Another objective of the present invention is to provide processes for the preparation of novel crystalline polymorphic Forms I & II of Imatinib mesyalte
  • Yet another objective of the present invention is to provide a novel pharmaceutical compositions containing the novel crystalline polymorphic Forms I or II of Imatinib mesyalte or their mixtures
  • the present invention relates to novel crystalline Forms I and II of imatinib mesylate and processes for the preparation of the said forms.
  • the new Form -I and Form - II is stable, and usually retains crystalline structure after heating to 60 -70°C overnight (at least about 8 hours). But prolonged heating of either of the Forms or heating at a temperature above 70°C results in the conversion to the ⁇ 2 Form disclosed in our above mentioned [Indian application No. 706/CHE/04].
  • stable refers to a polymorphic change of less than about 5% by weight, more preferably less than about 2%
  • the present invention provides novel crystalline Forms I & II of Imatinib
  • XRPD patterns were recorded using an x-ray powder diffractometer (Bruker AXS D5000) in transmission mode (Cu K alpha 1, PSD).
  • IR absorption spectra were measured in the spectral range 4000-400 cm ⁇ -l > on a Bruker IFS48. Spectral resolution was 2 cm ⁇ -l>. Sample preparation was performed generally as KBr disk.
  • a process for the preparation of the novel imatinib mesylate polymorph Form I which comprises slurring OC 2 or ⁇ polymorphic Form of imatinib mesylate in chloroform and water with heating and distilling off water and filtering to obtain the novel Form I
  • a process for the preparation of the novel imatinib mesylate Form II which comprises lyophilizing an aqueous solution of ⁇ 2 or ⁇ . Polymorph Forms of imatinib mesylate and filtering to obtain the Form II
  • Determination of the presence of Imatinib mesylate Form- ⁇ in Imatinib mesylate Form-I and Form-II prepared by the above defined processes of the present invention may be made by analysis for the presence of various peaks associated with Form- ⁇ particularly at 9.7, 13.9, 18.2, 20.0, 20.6, 21.1, 22.1, 22.7, 23.8, 29.8, 30.8 ⁇ 0.2 degree 2 ⁇ .(WO99/03854).
  • Determination of presence of Imatinib mesylate Form- ⁇ 2 in Imatinib mesylate Form-I and Form-II prepared by the above defined processes of the present invention may be made by analysis for the presence of various peaks associated with Form- ⁇ 2 particularly at 4.84, 10.4, 14.86, 16.40, 17.60, 18.05, 18.57, 19.03, 21.2, 21.58, 23.1, 23.69, 24.85, 28.47 ⁇ 0.2 degree 2 ⁇ [Indian application No. 706/CHE/04]
  • Fig.l represents the X-Ray Powder Diffraction (XRPD) pattern which substantially depicts a typically pure sample of Imatinib Mesylate of Form-I prepared by the process of the present invention.
  • XRPD X-Ray Powder Diffraction
  • the infrared spectrum of Form-I as a KBr tablet has the characteristic absorptions at the following wavelengths (in cm ⁇ -l>, f for weak, m for average, F for strong):
  • the infrared spectrum of Form-II as a KBr tablet has the characteristic absorptions at the following wavelengths (in cm ⁇ -l>, f for weak, m for average, F for strong):
  • excipients or adjutants may be readily determined by a person in the art based upon experience and consideration of standard procedures and reference works in the field.
  • Diluents may also be used to increase the bulk of a solid pharmaceutical composition, and to may make the pharmaceutical dosage form easier for the patient to handle.
  • Diluents which may be employed may include, for example, microcrystalline cellulose (e.g. Avicel(R)), microfine cellulose, lactose, starch, pregelitinized starch, calcium carbonate, calcium sulfate, sugar, dextrates, dextrin, dextrose, dibasic calcium phosphate dihydrate, tribasic calcium phosphate, kaolin, magnesium carbonate, magnesium oxide, maltodextrin, mannitol, polymethacrylates (e.g. Eudragit(R)), potassium chloride, powdered cellulose, sodium chloride, sorbitol and talc.
  • microcrystalline cellulose e.g. Avicel(R)
  • microfine cellulose e.g. Avicel(R)
  • lactose e.g. starch
  • pregelitinized starch calcium
  • Solid pharmaceutical compositions that are compacted into a dosage form, such as capsules may include excipients whose functions include helping to bind the active ingredient and other excipients together after compression.
  • Binders which may be employed for solid pharmaceutical compositions include acacia, alginic acid, carbomer (e.g. carbopol), carboxymethylcellulose sodium, dextrin, ethyl cellulose, gelatin, guar gum, hydrogenated vegetable oil, hydroxyethyl cellulose, hydroxypropyl cellulose (e.g. Klucel(R)), hydroxypropyl methyl cellulose (e.g. Methocel(R)), liquid glucose, magnesium aluminum silicate, maltodextrin, methylcellulose, polymethacrylates, povidone (e.g. Kollidon(R), Plasdone(R)), pregelatinized starch, sodium alginate and starch.
  • carbomer e.g. carbopol
  • carboxymethylcellulose sodium dextrin
  • ethyl cellulose gelatin
  • guar gum hydrogenated vegetable oil
  • hydroxyethyl cellulose hydroxypropyl cellulose
  • hydroxypropyl cellulose e.g
  • the dissolution rate of a compacted solid pharmaceutical composition in the patient's stomach may be increased by the addition of a disintegrant to the composition.
  • Disintegrants which may be employed for the purpose may include alginic acid, carboxymethylcellulose calcium, carboxymethylcellulose sodium (e.g. Ac-Di-SoI(R), Primellose(R)), colloidal silicon dioxide, croscarmellose sodium, crospovidone (e.g. Kollidon(R), Polyplasdone(R)), guar gum, magnesium aluminum silicate, methyl cellulose, macrocrystalline cellulose, polacrilin potassium, powdered cellulose, pregelatinized starch, sodium alginate, sodium starch glycolate (e.g. Explotab(R)) and starch.
  • alginic acid carboxymethylcellulose calcium, carboxymethylcellulose sodium (e.g. Ac-Di-SoI(R), Primellose(R)), colloidal silicon dioxide, croscarmellose sodium, crospovidone (e.g
  • Glidants can be added to improve the flowability of a non-compacted solid composition and to improve the accuracy of dosing.
  • Excipients that may function as glidants and which can be employed in the composition of the present invention may include colloidal silicon dixoide, magnesium trisilicate, powdered cellulose, starch, talc and tribasic calcium phosphate.
  • a dosage form such as a capsule
  • the composition is subjected to pressure from a punch and dye.
  • Some excipients and active ingredients have a tendency to adhere to the surfaces of the punch and dye, which can cause the product to have pitting and other surface irregularities.
  • a lubricant can be added to the composition to reduce the adhesion and ease the release of the product from the dye.
  • Lubricants which can be used may include magnesium stearate, calcium stearate, glyceryl monostearate, glyceryl palmitostearate, hydrogenated castor oil, hydrogenated vegetable oil, mineral oil, polyethylene glycol, sodium benzoate, sodium lauryl sulfate, sodium stearyl fumarate, stearic acid, talc and zinc stearate.
  • Flavoring agents and flavor helps the dosage form more palatable to the patient.
  • Common flavoring agents and flavor enhancers for pharmaceutical products can be employed which include maltol, vanillin, ethyl vanillin, menthol, citric acid, fumaric acid, ethyl maltol, and tartaric acid.
  • Solid compositions may also be dyed using any pharmaceutically acceptable colorant to improve their appearance and/or facilitate patient identification of the product and unit dosage level.
  • the dosage form of the present invention may be a capsule containing the composition, preferably a powdered or granulated solid composition of the invention, within either a hard or soft shell.
  • the shell may be made from gelatin and optionally contain a plasticizer such as glycerin and sorbitol, and an opacifying agent or colorant.
  • compositions and dosage forms may be formulated into compositions and dosage forms according to methods known in the art.
  • a composition for tableting or capsule filling may be prepared by dry blending.
  • dry blending some or all of the active ingredients and excipients in powder form are blended
  • the blend is screened and/or milled, dried and then screened and/or milled to the desired particle size.
  • the granulate may then be tableted, or other excipients may be added prior to tableting, such as a glidant and/or a lubricant
  • a blended composition may be compressed directly into a compacted dosage form using direct compression techniques. Direct compression produces a more uniform tablet without granules.
  • Excipients that are particularly well suited for direct compression tableting include microcrystalline cellulose; spray dried lactose, dicalcium phosphate dihydrate and colloidal silica. The proper use of these and other excipients in direct compression tableting is known to those in the art with experience and skill in particular formulation challenges of direct compression tableting.
  • a capsule filling of the present invention may comprise any of the aforementioned blends and granulates that were described with reference to tableting, however, they are not subjected to a final tableting step.
  • the dosage used is preferably from about 120mg to 360mg of imatinib mesylate, more preferably about 120 mg of imatinib mesylate of form I or form II
  • Imatinib base 200 gms was suspended in 2.5 L of ⁇ sopropanol.
  • Methane sulfonic acid 38.9 gms
  • 400 ml anhydrous Isopropanol was added slowly during 20 minutes at room temperature.
  • the reaction mass was heated to 75-8O 0 C for 30 minutes and slowly cooled to 40-45°C during 45 minutes. Filtered at 40-45 0 C and washed with 250 ml Isopropanol.
  • the wet cake was dried for 6 hours at 8O 0 C.
  • the yield was 170 gms (71%) Melting range - 223-227 0 C, DSC Thermogram 227°C (Peak)
  • Imatinib mesylate ⁇ 2 crystal form obtained by the process described in step A above was suspended in 500 m i water and 5-litre chloroform. Distilled off water completely along with chloroform during 4-6 hours at normal pressure. Cooled to room temperature and stirred at the same temperature till crystal formation is completed. Filtered and washed chloroform. The wet cake was dried under vacuum at 50-60 0 C. The yield was 163 gms of crystalline form I of imatinib mesylate
  • Imatinib base (0.25 Kg) was suspended in 12 L of acetone Methane sulfonic acid (48.6 gms) in 0.5 L acetone was added slowly during 30 minutes at room temperature. The reaction mass was heated to reflux temperature for 30 minutes and was slowly brought to room temperature during 45 minutes. Filtered and washed with 1 L acetone and dried for 6 hours at 65°C. The yield was 255 gms (85%) Melting range- 215-217 0 C, DSC Thermogram 217 0 C (Peak) XRPD as shown in Fig-4, IR spectrum as shown in Fig-5 DSC thermogram as shown in Fig-6
  • Crystalline ⁇ - Form of Imatinib mesylate obtained by the process described in A above was suspended in 750 ml water and 7.5 litre chloroform. Distilled off water completely along with chloroform during 4-6 hours at normal pressure. Cooled to room temperature and stirred at the same temperature till crystal formation is completed. Filtered and washed chloroform. The wet cake was dried under vacuum at 50-60 0 C. The yield was 230 gms of crystalline Form I of imatinib mesylate. Melting range -122.6-138.9 0 C, DSC Thermogram 138.9 0 C (Peak)
  • Preparation of crystalline Form II of imatinib mesylate A) Preparation of crystalline ⁇ - Form of imatinib mesylate: Imatinib base (0.25 Kg) was suspended in 12 L of acetone. Methane sulfonic acid (48.6 gms) in 0.5 L acetone was added slowly during 30 minutes at room temperature. The reaction mass was heated to reflux temperature for 30 minutes and was slowly brought to room temperature during 45 minutes. Filtered and washed with 1 L acetone and dried for 6 hours at 65°C. The yield was 255 gms (85%) Melting range- 215-217°C, DSC Thermogram 217°C (Peak) B) Preparation of crystalline Form II of Imatinib mesylate:
  • Imatinib base 200 gms was suspended in 2.5 L of isopropanol.
  • Methane sulfonic acid 38.9 gms
  • 400 ml anhydrous Isopropanol was added slowly during 20 minutes at room temperature.
  • the reaction mass was heated to 75-80°C for 30 minutes and slowly cooled to 40-45°C during 45 minutes. Filtered at 40-45°C and washed with 250 ml Isopropanol.
  • the wet cake was dried for 6 hours at 80°C.
  • the yield was 170 gms (71%) Melting range - 223-227°C, DSC Thermogram 227°C (Peak)
  • Example-6 Conversion of crystalline Form II of imatinib mesylate to Form-I ;
  • Capsules containing 120 mg of active ingredient of the Form-I described in the Examples 1 and 2 having the following composition are prepared in customary manner.
  • Capsules containing 120 mg of active ingredient of the compound describe in the Examples 3 and 4 having the following composition are prepared in customary manner.

Abstract

Cette invention concerne de nouvelles formes polymorphes cristallines I et II de mésylate d'imatinibe et des procédés servant à la préparation de ces nouvelles formes. On prépare la forme I en constituant une pâte de la forme polymorphe de mésylate d'imatinibe α2 ou ß dans du chloroforme et de l'eau avec chauffage et distillation de l'eau, suivis d'un filtrage. On prépare la forme II en lyophilisant une solution aqueuse du polymorphe α2 ou ß. Cette invention concerne également une composition pharmaceutique contenant ces nouvelles formes, qui est utile dans le traitement de la leucémie myélogène chronique et des états de stress accéléré.
PCT/IN2005/000273 2004-11-17 2005-08-11 Formes polymorphes de mesylate d'imatinibe WO2006054314A1 (fr)

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IN1206CH2004 2004-11-17

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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007023182A1 (fr) * 2005-08-26 2007-03-01 Novartis Ag Formes cristallines delta et epsilon d'imatinib mesylate
WO2007059963A1 (fr) * 2005-11-25 2007-05-31 Novartis Ag Formes cristallines f, g, h, i et k du mésylate d’imatinib
WO2006133046A3 (fr) * 2005-06-03 2007-07-26 Elan Pharma Int Ltd Formulations d'imatinib mesylate nanoparticulaires
WO2008027600A2 (fr) * 2006-09-01 2008-03-06 Teva Pharmaceutical Industries Ltd. Compositions d'imatinib
EP1920767A1 (fr) * 2006-11-09 2008-05-14 Abbott GmbH & Co. KG Forme posologique d'Imatinib préparée à l'état fondu.
EP1988089A1 (fr) 2006-10-26 2008-11-05 Sicor, Inc. Base d'imatinib, et mesylate d'imatinib et son procédé de préparation
WO2008150481A2 (fr) * 2007-05-29 2008-12-11 Sicor Inc. Procédé de préparation de la forme cristalline bêta d'un mésylate d'imatinibe
US7550591B2 (en) 2007-05-02 2009-06-23 Chemagis Ltd. Imatinib production process
WO2010133976A2 (fr) 2009-05-22 2010-11-25 Actavis Group Ptc Ehf Imatinib sensiblement pure ou sel de celui-ci pharmaceutiquement acceptable
JP2010540465A (ja) * 2007-09-25 2010-12-24 テバ ファーマシューティカル インダストリーズ リミティド 安定なイマチニブ組成物
WO2011023146A1 (fr) 2009-08-26 2011-03-03 Zentiva, K.S. Polymorphes de mésylate d'imatinib générés par cristallisation dans des solutions salines inorganiques aqueuses
EP2311821A1 (fr) 2006-04-27 2011-04-20 Sicor, Inc. Forme polymorphique de mesylate d'imatinib et ses procédés de préparation
WO2011049474A1 (fr) 2009-10-22 2011-04-28 Tomasz Kozluk Sels d'imatinib avec des acides tartriques
US7947699B2 (en) 2008-01-10 2011-05-24 Actavis Group Ptc Ehf Anhydrous amorphous imatinib mesylate
US7977348B2 (en) 2006-04-27 2011-07-12 Sicor Inc. Polymorphic forms of imatinib mesylate and processes for preparation of novel crystalline forms as well as amorphous and form α
WO2011095835A1 (fr) 2010-02-02 2011-08-11 Actavis Group Ptc Ehf Imatinib de grande pureté ou un sel pharmaceutiquement acceptable de celui-ci
WO2011099039A1 (fr) 2010-02-15 2011-08-18 Reliance Life Sciences Pvt. Ltd. Procédé pour la préparation d'une forme alpha de mésylate d'imatinib
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
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
WO2011157450A1 (fr) 2010-06-18 2011-12-22 Krka, D. D., Novo Mesto Nouvelle forme polymorphique d'imatinib base et préparation de ses sels
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
WO2012090221A1 (fr) 2010-12-29 2012-07-05 Cadila Healthcare Limited Nouveaux sels d'imatinib
CN102584787A (zh) * 2012-01-19 2012-07-18 山东金城医药化工股份有限公司 甲磺酸伊马替尼晶体的超声制备方法
EA017781B1 (ru) * 2011-05-24 2013-03-29 Тева Канада Лимитед Покрытая пленочной оболочкой таблетка, содержащая иматиниб мезилат, и способ ее получения
EA017782B1 (ru) * 2011-05-24 2013-03-29 Плива Кроэйша Лтд. Капсула, содержащая иматиниб мезилат, и способ ее получения
EP2604596A1 (fr) * 2011-12-16 2013-06-19 Deva Holding Anonim Sirketi Polymorphes d'imatinib
WO2013189910A1 (fr) 2012-06-22 2013-12-27 Basf Se Cristaux multicomposants comprenant du mésilate d'imatinib et des agents de co-cristallisation choisis
CN103864752A (zh) * 2010-05-19 2014-06-18 江苏豪森药业股份有限公司 甲磺酸伊马替尼的晶型及其制备方法
WO2014199244A3 (fr) * 2013-06-12 2015-04-02 Shilpa Medicare Limited Procédé de préparation de mésylate d'imatinib cristallin
WO2015188243A1 (fr) * 2014-06-10 2015-12-17 Cristália Produtos Químicos Farmacêuticos Ltda Procédé de préparation d'imatinib et de mésylate d'imatinib sous forme α2 non aciculaire
WO2017078647A1 (fr) 2015-11-05 2017-05-11 Koçak Farma Ilaç Ve Kimya Sanayi Anonim Şirketi Compositions pharmaceutiques d'imatinib
WO2017129624A1 (fr) 2016-01-25 2017-08-03 Krka, D.D., Novo Mesto Composition pharmaceutique à dispersion rapide comprenant un inhibiteur de la tyrosine kinase
CN107778291A (zh) * 2016-08-31 2018-03-09 亚宝药业集团股份有限公司 一种甲磺酸达比加群酯晶型ⅱ的制备方法
CN115463238A (zh) * 2022-09-16 2022-12-13 海信冰箱有限公司 一种冰箱除臭材料、其制备方法及冰箱

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EP0564409A1 (fr) * 1992-04-03 1993-10-06 Ciba-Geigy Ag Dérivés de pyrimidine et procédé pour leur préparation
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WO2004074502A2 (fr) * 2003-02-18 2004-09-02 Cipla Ltd Procede de preparation d’imatinibe et produit ainsi prepare
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Cited By (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006133046A3 (fr) * 2005-06-03 2007-07-26 Elan Pharma Int Ltd Formulations d'imatinib mesylate nanoparticulaires
EA015102B1 (ru) * 2005-06-03 2011-06-30 Элан Фарма Интернэшнл Лтд. Препараты наночастиц мезилата иматиниба
WO2007023182A1 (fr) * 2005-08-26 2007-03-01 Novartis Ag Formes cristallines delta et epsilon d'imatinib mesylate
US7879860B2 (en) 2005-08-26 2011-02-01 Novartis Ag Delta and epsilon crystal forms of Imatinib mesylate
US8846706B2 (en) 2005-11-25 2014-09-30 Novartis Ag Crystalline form K of imatinib mesylate
US8198289B2 (en) 2005-11-25 2012-06-12 Novartis Ag Crystal form H imatinib mesylate for pharmaceutical use
US8592440B2 (en) 2005-11-25 2013-11-26 Novartis Ag Crystalline form I of imatinib mesylate
US8633213B2 (en) 2005-11-25 2014-01-21 Novartis Ag Crystalline form F of imatinib mesylate
EP2546248A1 (fr) * 2005-11-25 2013-01-16 Novartis AG Forme cristalline H de mésylate d'imatinib
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