WO2008067773A1 - Nouveaux types de cristaux de febuxostat et procédés de préparation de ceux-ci - Google Patents

Nouveaux types de cristaux de febuxostat et procédés de préparation de ceux-ci Download PDF

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Publication number
WO2008067773A1
WO2008067773A1 PCT/CN2007/071194 CN2007071194W WO2008067773A1 WO 2008067773 A1 WO2008067773 A1 WO 2008067773A1 CN 2007071194 W CN2007071194 W CN 2007071194W WO 2008067773 A1 WO2008067773 A1 WO 2008067773A1
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WIPO (PCT)
Prior art keywords
febuxostat
solvent
crystal
crystallization
solution
Prior art date
Application number
PCT/CN2007/071194
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English (en)
Chinese (zh)
Inventor
Xingguo Zhou
Xuemin Tang
Jie Deng
Wenrun Ye
Jie Luo
Daolin Zhang
Bin Fan
Original Assignee
Chongqing Pharmaceutical Research Institute Co., Ltd.
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Application filed by Chongqing Pharmaceutical Research Institute Co., Ltd. filed Critical Chongqing Pharmaceutical Research Institute Co., Ltd.
Publication of WO2008067773A1 publication Critical patent/WO2008067773A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic 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
    • C07D277/32—Heterocyclic 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents

Definitions

  • the invention belongs to the technical field of medicinal chemistry, and specifically relates to three novel crystal forms H, I and J of febuxostat and a preparation method thereof, a pharmaceutical composition containing the three new crystal forms, and the same thereof.
  • Febuxostat has been registered with the US FDA for the treatment of diseases associated with high levels of uric acid, such as gout, to lower uric acid in the blood.
  • uric acid such as gout
  • Chinese patent CN1275126 describes polymorphs A, B, C, D, G, and amorphous forms thereof, which are invented by Teijin Corporation, and which are invented by the Japanese Teijin Corporation.
  • crystal A exists in a metastable crystal form
  • crystal B is obtained by hydrated G by drying under reduced pressure
  • crystal C is prepared by solvent-mediated polymorphic conversion
  • crystal D is a decyl alcoholate, which is at a low temperature.
  • crystal A has a characteristic absorption at about 1678 cm- 1 which distinguishes it from other crystal forms
  • crystal B has a difference between 1715, 1701 and 1682 cm- 1 to distinguish it from other crystal forms.
  • crystal G has characteristic absorption at about 1703 and 1684 cm- 1 that distinguishes it from other crystal forms.
  • the present inventors unexpectedly discovered that there are three other crystal forms of febuxostat, which are different from any of the six crystal forms disclosed in CN1275126, the three new crystal forms.
  • the crystal form In the absence of water and other crystalline forms of the solvent, the crystal form has good stability and can be used for the manufacture of a medicament for treating diseases associated with hyperuricemia, and is suitable for the formulation process and long-term storage. Summary of the invention
  • the object of the present invention provides three crystal forms of febuxostat.
  • the first non-busvastatin crystal form of the present invention is named H type, and the x-ray ray powder diffraction (XRPD) characteristic absorption peak (2 ⁇ ) value is about 6.71, 7.19, 10.03, 11.10, 12.96, 13.48, 15.78, 17.60 and 22.15°; see Figure 1.
  • the crystals have characteristic absorption peaks at about 2238, 1701, 1678, and 1116 cm 1 that can be distinguished from other crystal forms by infrared analysis, as shown in FIG.
  • the second non-bustaster new crystal form disclosed by the present invention the crystal form is named I type, and the X-ray ray powder diffraction (XRPD) characteristic absorption peak (2 ⁇ ) value of the crystal form is about 3.28, 6.58, 12.70, 13.34, 19.97, 24.26 and 25.43°, see Figure 3.
  • the crystal was analyzed by infrared, and its infrared spectrum has characteristic absorption peaks at about 1730, 1253 and 1097 cu 1 which can distinguish it from other crystal forms, as shown in Fig. 4.
  • the third novel form of febuxostat disclosed in the present invention the crystal form is named J type, and the X-ray ray powder diffraction (XRPD) characteristic absorption peak (2 ⁇ ) value of the crystal form is about 3.07, 12.25, 13.16, 25.21 and 26.86°, see Figure 5.
  • the crystal was analyzed by infrared, and its infrared spectrum has characteristic absorption at about 1686 and 1655 cm" which distinguishes it from other crystal forms, as shown in Fig. 6.
  • the measurement of the 2 ⁇ value is performed using a CuKa light source with an accuracy of ⁇ 0.2°. Therefore, the above-mentioned "X-ray ray powder diffraction (XRPD) characteristic absorption peak (2 ⁇ ) value of the crystal form is approximately "about” "It should be defined as 2 ⁇ ⁇ 0.2°, which means that the 2 ⁇ value taken above allows a reasonable margin of error with an error range of ⁇ 0.2°.
  • XRPD X-ray ray powder diffraction
  • Another object of the invention is to disclose a process for the preparation of a new form of febuxostat.
  • the preparation method of the febuxostat form H of the present invention comprises: tempering a solution of febuxostat in a solvent of CN at a temperature of about 15 to 50 C, wherein the alkyl group or the alkyl group is represented by an alkyl group or an alkyl group. .
  • the mass to volume ratio (g/ml) of the febuxostat to the RN solvent in the solution is about 1:30 to 1:100, preferably about 1:35 to 1:50.
  • the crystallization tempering temperature is preferably about crystallization and can be filtered if necessary; optionally at about 80-120 C under normal pressure.
  • CN solvent may be acetonitrile, propionitrile, butyronitrile, chloropropionitrile or the like, preferably acetonitrile, propionitrile or a mixture thereof.
  • the method of the febuxostat Form I of the present invention comprises: optionally at rest In the state, a solution of febuxostat in a solvent of CN is decompressed to a crystal at a temperature of 20 to 60, wherein an alkyl group or an alkyl group is represented.
  • the mass to volume ratio (g/ml) of the febuxostat to the CN solvent in the solution is preferably from about 1:30 to 1:100, preferably about 1:50; if heating is required Dissolving; at a standstill, the temperature at which the solvent is withdrawn under reduced pressure is preferably about to be filtered if necessary after crystallization; optionally drying under reduced pressure, preferably under reduced pressure for a suitable period of time, for example 24 hours, to obtain substantially dry Form I; preferably fluorenyl, ethyl, propyl, chloro-substituted ethyl, preferred solvents are acetonitrile, propionitrile or mixtures thereof.
  • the method of the non-buxostat form J of the present invention comprises: heating and melting febuxostat, followed by crystallization by cooling, for example, by natural cooling or forced cooling, especially rapid cooling to room temperature.
  • the febuxostat is dissolved in the RN solvent, and the mass to volume ratio (g/ml) of the febuxostat to the RN solvent is preferably 1:30 to 1:100, more preferably 1 : 30; if necessary, can be dissolved by heating, and then decrystallized, for example, static crystallization; optionally, suction filtration, and then the product obtained by suction filtration, for example, is heated and melted under normal pressure, and then cooled and crystallized to obtain a crystal form J; Alkyl or haloalkyl, preferably decyl, ethyl, propyl, chloro substituted ethyl, preferred solvents are acetonitrile, propionitrile or mixture
  • a further object of the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a therapeutically effective amount of febuxostat Form H, Form I or Form J of the present invention and a pharmaceutically acceptable adjuvant or carrier, wherein
  • the bucystat form preferably has an average particle size suitable for the process, for example, 1 ⁇ m or more and 50 ⁇ m or less.
  • the preparation form of the pharmaceutical composition may be an oral preparation, an injection and an external preparation; and the oral preparation may be, for example, a tablet, capsule, granule, controlled release tablet or capsule, orally disintegrated, dissolved and dispersed. Tablets.
  • the various preparations can be prepared by the corresponding known pharmaceutical preparation techniques using corresponding excipients known to those of ordinary skill in the art.
  • the effective therapeutic amount may be, for example, 10 to 200 mg, preferably 40 to 120 mg.
  • the above-mentioned oral solid dosage form contains 20 mg, 40 mg, 80 mg, or 120 mg of the febuxostat crystal form of the present invention per dose, and the "per dose" means each tablet.
  • each capsule (gelatin), etc. use 1 ⁇ 2 times a day, 1 ⁇ 4 doses each time.
  • the pharmaceutical composition of the present invention may contain a usual excipient such as a binder, a filler, a diluent, a tablet, a lubricant, a disintegrant, a coloring agent, a flavoring agent, and a lubricant when it is a solid oral preparation.
  • a usual excipient such as a binder, a filler, a diluent, a tablet, a lubricant, a disintegrant, a coloring agent, a flavoring agent, and a lubricant when it is a solid oral preparation.
  • the tablets can be coated if necessary.
  • Examples of the filler include lactose, mannitol, xylitol, starch, pregelatinized starch, corn starch, microcrystalline cellulose, sorbitol, which can be used alone It can also be used in combination.
  • the aforementioned filler is preferably lactose, mannitol or microcrystalline cellulose.
  • Examples of the disintegrant include low-substituted hydroxypropylcellulose, crosslinked polyvinylpyrrolidone, polyvinylpyrrolidone, starch, microcrystalline cellulose, and sodium carboxymethylcellulose, which may be used singly or in combination.
  • the above disintegrant is preferably a low-substituted hydroxypropylcellulose, a starch, or a polyvinylpyrrolidone.
  • binder examples include hydroxypropyl decyl cellulose, hydroxypropyl cellulose, polyvinyl pyrrolidone, starch syrup, polyvinyl alcohol, microcrystalline cellulose, water, various concentrations of ethanol solution, which can It can also be used alone or in combination.
  • the aforementioned binder is preferably microcrystalline cellulose, hydroxypropyl decyl cellulose, various concentrations of ethanol solution.
  • lubricant examples include stearic acid, magnesium stearate, stearic acid 5, palmitic acid, aluminum silicate, stearic acid amide, talc, and silica, which may be used singly or in combination.
  • the aforementioned lubricant is preferably magnesium stearate or aluminum silicate.
  • excipients such as sweeteners, colorants, taste masking agents, stabilizers may also be added to the pharmaceutical compositions of the present invention.
  • the pharmaceutical composition of the present invention can be prepared according to any of the conventional methods for preparing an oral solid preparation, such as: wet granulation tablet, direct tablet compression, and granulation.
  • the pharmaceutical composition can be coated into a film-coated tablet or a sugar-coated tablet using a conventional coating device.
  • the coating base includes celluloses, acrylics, saccharides such as hydroxypropyl thioglycolate, Eudragit L, sucrose.
  • a plasticizer, an anti-adhesive agent, and an opacifier may also be added to the coating base.
  • wetting agents which may be added include ethylene glycol, propylene glycol, sorbitol and glycerin and fatty acid esters thereof, and these wetting agents may be used singly or in the form of two or more of them. Use in any combination.
  • the solid pharmaceutical composition of the present invention can be obtained in a conventional dosage form by sequentially performing a granulation step, an encapsulation step or a tableting step, and a coating step (if necessary), usually a tablet or a surface coated tablet, a powder. , granules, surface coated granules or capsule dosage forms.
  • the tablets include conventional tablets, sustained release tablets, buccal tablets, orally disintegrating tablets, chewable tablets, effervescent tablets and the like.
  • the pharmaceutical composition of the present invention can be prepared by conventional techniques of pharmacy. For example, wet granulation tableting and dry powder direct compression can be used for tablets.
  • the present invention also provides the use of the crystalline forms of febuxostat of H, I, and J in the manufacture of a medicament for treating diseases associated with hyperuricemia, said hyperacic acid-related diseases mainly referring to hyperuricemia.
  • diseases associated with hyperuricemia said hyperacic acid-related diseases mainly referring to hyperuricemia.
  • the form of H, Form I or Form J of febuxostat of the present invention It has strong uric acid activity in the blood, and it also has good stability.
  • Figure 1 is an X-ray diffraction pattern of the H-form of febuxostat according to Example 1 of the present invention.
  • Fig. 2 is a chart showing the infrared absorption spectrum of H-form of febuxostat according to Example 1 of the present invention.
  • Figure 3 is a X-ray diffraction pattern of Form I of febuxostat according to Example 2 of the present invention.
  • Fig. 4 is a chart showing the infrared absorption spectrum of Form I of febuxostat according to Example 2 of the present invention.
  • Fig. 5 is a J-type X-ray diffraction pattern of the non-busestat of Example 3 of the present invention.
  • Fig. 6 is a chart showing the infrared absorption spectrum of J crystal form of febuxostat according to Example 3 of the present invention. detailed description
  • the 120 mg febuxostat gum granules were prepared as follows:
  • febuxostat H crystal form 80g pregelatinized starch 110.5g, low-substituted hydroxypropyl decyl cellulose 10.5g, magnesium stearate 0.8g, made into 1000 tablets
  • the total amount of impurities in each polymorph did not change during the entire test period as compared to before the start of the test. It is demonstrated that the crystalline form of the present invention is relatively stable and is suitable for the manufacture of pharmaceutical agents and for long term storage.
  • the form of H, Form I or Form J of febuxostat of the present invention has a strong activity of lowering uric acid in the blood.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne le domaine de la technologie pharmaceutique. L'invention concerne trois nouveaux types de cristaux de l'acide 2-(3-cyano-4-isobutyloxy)phényl-4-méthyl-5-thiazolecarboxylique (febuxostat), c'est-à-dire les types de cristaux H, I et J; et des procédés de préparation de ceux-ci. L'invention concerne également des compositions pharmaceutiques contenant les nouveaux types de cristaux et les utilisations des types de cristaux en tant que médicaments pour le traitement de maladies liées à un excès d'acide urique. En outre, la présente invention indique le pic d'absorption caractéristique en diffraction des rayons X et le pic d'absorption des IR.
PCT/CN2007/071194 2006-12-07 2007-12-06 Nouveaux types de cristaux de febuxostat et procédés de préparation de ceux-ci WO2008067773A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010144685A1 (fr) 2009-06-10 2010-12-16 Teva Pharmaceutical Industries Ltd. Forme cristalline du febuxostat
JP2011020950A (ja) * 2009-07-15 2011-02-03 Mitsutaka Kitamura ２−（３−シアノ−４−イソブチルオキシフェニル）−４−メチル−５−チアゾールカルボン酸の結晶多形体の製造方法
WO2011080651A2 (fr) 2009-12-31 2011-07-07 Ranbaxy Laboratories Limited Formes polymorphes de fébuxostat
WO2011107911A1 (fr) 2010-03-04 2011-09-09 Ranbaxy Laboratories Limited Polymorphe d'acide 2-[3-cyano-4-(2-méthylpropoxy) phényl]-4-méthylthiazole-5-carboxylique
WO2012020272A2 (fr) 2010-08-13 2012-02-16 EGIS GYÓGYSZERGYÁR Nyilvánosan Müködö Részvénytársaság Nouveaux sels, polymorphes et solvates d'un ingrédient pharmaceutiquement actif
WO2012048861A1 (fr) 2010-10-14 2012-04-19 Gador S.A. Nouvelle forme cristalline du febuxostat et son procédé de préparation
WO2013088449A1 (fr) 2011-12-16 2013-06-20 Natco Pharma Limited Forme cristalline stable de febuxostat et procédé de préparation correspondant
EP2692342A1 (fr) 2012-07-30 2014-02-05 Interquim, S.A. Procédé pour la préparation de compositions pharmaceutiques comprenant du Febuxostat sous la forme de comprimés
EP2902016A1 (fr) 2014-01-30 2015-08-05 Alfred E. Tiefenbacher (GmbH & Co. KG) Comprimé Febuxostat

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CN101412700B (zh) * 2007-10-19 2011-06-08 上海医药工业研究院 非布司他的晶型及其制备方法
CN101386605B (zh) * 2008-10-23 2010-09-08 中国科学院上海药物研究所 非布司他新型晶体及其制备方法
CN101474175B (zh) * 2009-01-20 2014-07-02 重庆医药工业研究院有限责任公司 一种高生物利用度非布司他口服固体制剂及其制备方法
CN101862326B (zh) * 2009-04-20 2013-12-04 北京德众万全药物技术开发有限公司 一种含非布索坦的药物组合物
CN101891702B (zh) * 2009-05-22 2012-07-04 重庆圣华曦药业股份有限公司 非布司他的晶体、制备方法及在药物中的应用
CN101929988B (zh) * 2009-06-26 2014-05-07 北京德众万全药物技术开发有限公司 一种用高效液相色谱法测定非布索坦有关物质的方法
CN103936689B (zh) * 2009-07-17 2016-08-17 北京利乐生制药科技有限公司 2-[3-氰基-4-异丁氧基苯基]-4-甲基噻唑-5-甲酸晶型及其制备方法
CN101824005B (zh) * 2010-04-27 2012-06-27 上海凯米侬医药科技有限公司 一种非布索坦的晶型q及其制备方法
CN102018705A (zh) * 2010-12-17 2011-04-20 江苏同禾药业有限公司 一种含有非布司他晶体的药物组合物及制备方法
CN102127033A (zh) * 2011-01-21 2011-07-20 北京虹湾医药技术有限公司 非布索坦晶型及其工业化制备方法
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8609856B2 (en) 2009-06-10 2013-12-17 Teva Pharmaceuticals Usa, Inc. Crystalline forms of Febuxostat
JP2012529537A (ja) * 2009-06-10 2012-11-22 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 フェブキソスタットの結晶形
US8742129B2 (en) 2009-06-10 2014-06-03 Teva Pharmaceutical Industries Ltd. Crystalline forms of febuxostat
WO2010144685A1 (fr) 2009-06-10 2010-12-16 Teva Pharmaceutical Industries Ltd. Forme cristalline du febuxostat
CN102803240A (zh) * 2009-06-10 2012-11-28 特瓦制药工业有限公司 非布索坦的晶形
US8415481B2 (en) 2009-06-10 2013-04-09 Teva Pharmaceuticals Usa, Inc. Crystalline form of febuxostat
EP2532654A1 (fr) 2009-06-10 2012-12-12 Teva Pharmaceutical Industries Ltd. Forme cristalline du febuxostat
DE202010017868U1 (de) 2009-06-10 2012-11-28 Teva Pharmaceutical Industries Ltd. Kristalline Formen von Febuxostat
JP2011020950A (ja) * 2009-07-15 2011-02-03 Mitsutaka Kitamura ２−（３−シアノ−４−イソブチルオキシフェニル）−４−メチル−５−チアゾールカルボン酸の結晶多形体の製造方法
WO2011080651A2 (fr) 2009-12-31 2011-07-07 Ranbaxy Laboratories Limited Formes polymorphes de fébuxostat
WO2011107911A1 (fr) 2010-03-04 2011-09-09 Ranbaxy Laboratories Limited Polymorphe d'acide 2-[3-cyano-4-(2-méthylpropoxy) phényl]-4-méthylthiazole-5-carboxylique
WO2012020272A2 (fr) 2010-08-13 2012-02-16 EGIS GYÓGYSZERGYÁR Nyilvánosan Müködö Részvénytársaság Nouveaux sels, polymorphes et solvates d'un ingrédient pharmaceutiquement actif
WO2012048861A1 (fr) 2010-10-14 2012-04-19 Gador S.A. Nouvelle forme cristalline du febuxostat et son procédé de préparation
WO2013088449A1 (fr) 2011-12-16 2013-06-20 Natco Pharma Limited Forme cristalline stable de febuxostat et procédé de préparation correspondant
EP2692342A1 (fr) 2012-07-30 2014-02-05 Interquim, S.A. Procédé pour la préparation de compositions pharmaceutiques comprenant du Febuxostat sous la forme de comprimés
EP2902016A1 (fr) 2014-01-30 2015-08-05 Alfred E. Tiefenbacher (GmbH & Co. KG) Comprimé Febuxostat

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