WO2013030722A1 - Chlorhydrate de lurasidone cristallin - Google Patents

Chlorhydrate de lurasidone cristallin Download PDF

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Publication number
WO2013030722A1
WO2013030722A1 PCT/IB2012/054248 IB2012054248W WO2013030722A1 WO 2013030722 A1 WO2013030722 A1 WO 2013030722A1 IB 2012054248 W IB2012054248 W IB 2012054248W WO 2013030722 A1 WO2013030722 A1 WO 2013030722A1
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WO
WIPO (PCT)
Prior art keywords
lurasidone hydrochloride
crystalline
crystalline lurasidone
hydrochloride
present
Prior art date
Application number
PCT/IB2012/054248
Other languages
English (en)
Inventor
Suresh Babu Jayachandra
Tarun Kumar SINGH
Udaibhan Singh GAHLOT
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 WO2013030722A1 publication Critical patent/WO2013030722A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Definitions

  • the present invention provides crystalline lurasidone hydrochloride, processes for its preparation, a pharmaceutical composition comprising it and its use for the treatment of schizophrenia.
  • Lurasidone hydrochloride is chemically (3aR,4S,7R,7aS)-2- ⁇ (lR,2R)-2-[4-(l,2- benzisothiazol-3-yl)piperazin- 1 -ylmethyl]cyclohexylmethyl ⁇ hexahydro-4,7-methano-2H- isoindole-l,3-dione hydrochloride, having the structure as represented by Formula I and is known from U.S. Patent No. 5,532,372.
  • the present invention provides crystalline lurasidone hydrochloride, a
  • Crystalline lurasidone hydrochloride of the present invention is a highly pure, easy to filter, free- flowing solid having small average particle size. Crystalline lurasidone hydrochloride of the present invention is stable towards polymorphic conversion and shows little or no variation in dissolution profile.
  • a first aspect of the present invention provides crystalline lurasidone
  • hydrochloride characterized by X-ray diffraction peaks at d-spacing of about 5.87, 5.39, 5.19, 4.55 and 4.05 A.
  • a second aspect of the present invention provides a process for the preparation of crystalline lurasidone hydrochloride characterized by X-ray diffraction peaks at d-spacing of about 5.87, 5.39, 5.19, 4.55 and 4.05 A, comprising adding 7% aqueous hydrochloric acid solution to a reaction mixture containing lurasidone in 2-propanol.
  • a third aspect of the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising crystalline lurasidone hydrochloride characterized by X-ray diffraction peaks at d-spacing of about 5.87, 5.39, 5.19, 4.55 and 4.05 A and one or more pharmaceutically acceptable carriers, diluents or excipients.
  • a fourth aspect of the present invention provides the use of crystalline lurasidone hydrochloride characterized by X-ray diffraction peaks at d-spacing of about 5.87, 5.39, 5.19, 4.55 and 4.05 A for the treatment of schizophrenia.
  • Figure 1 X-ray diffraction (XRD) spectrum of crystalline lurasidone hydrochloride.
  • FIG. 1 Differential Scanning Thermogram (DSC) of crystalline lurasidone hydrochloride.
  • Figure 4 Infra-red (IR) spectrum of crystalline lurasidone hydrochloride.
  • ambient temperature includes temperature in the range of about 20°C to about 35°C.
  • contacting may include dissolving, slurrying, stirring or a combination thereof.
  • Crystalline lurasidone hydrochloride of the present invention may be characterized by XRD peaks at about 15.11 (d-spacing at about 5.87 A), 16.44 (5.39 A), 17.09 (5.19 A), 19.53 (4.55 A) and 21.95 (4.05 A) ⁇ 0.2° 2 ⁇ . It may be further characterized by XRD peaks at about 1 1.41 (7.76 A), 13.89 (6.37 A), 15.49 (5.72 A), 20.78 (4.28 A) and 27.36 (3.26 A) ⁇ 0.2° 2 ⁇ . Crystalline lurasidone hydrochloride may also be characterized by XRD pattern as depicted in Figure 1.
  • Crystalline lurasidone hydrochloride of the present invention may also be characterized by DSC having endotherm at about 284.14°C.
  • Figure 2, Figure 3 and Figure 4 provide DSC, TGA and IR of crystalline lurasidone hydrochloride of the present invention, respectively.
  • Crystalline lurasidone hydrochloride of the present invention has a purity of at least 99%, as determined by High Performance Liquid Chromatography (HPLC).
  • Table 1 XRD peaks of crystalline lurasidone hydrochloride of the present invention
  • Lurasidone to be used for the preparation of crystalline lurasidone hydrochloride of the present invention, may be obtained by the method described in U.S. Patent No. 5,532,372, which is incorporated herein by reference. It may be obtained as a solution directly from the reaction in which it is formed and used as such without isolation.
  • lurasidone may be obtained by refluxing a reaction mixture containing ?ra «5-3a,7a-octahydroisoindolium-2-spiro- -[4'-(l,2-benzisothiazol-3-yl)]piperazine methane sulfonate, bicyclo[2.2.1]heptane-2-exo-3-exo-dicarboximide, dibenzo-18-crown- 6 and potassium carbonate in xylene or toluene for about 16 hours to about 36 hours followed by filtration and distillation of filtrate at about 70°C under reduced pressure.
  • lurasidone may be added to 2-propanol at ambient temperature.
  • the reaction mixture may be cooled to a temperature of between -10°C and 15°C. 7% Aqueous hydrochloric acid solution may be added.
  • the reaction mixture may be stirred from 30 minutes to about 10 hours, filtered, washed with 2-propanol and dried. Drying may be accomplished by any suitable method, such as air drying, drying under reduced pressure, vacuum tray drying or a combination thereof. Drying may be carried out at a temperature of about 35°C to about 60°C for about 5 hours to about 50 hours. In the preferred embodiment of the present invention, drying is carried out at a temperature of about 45°C for about 17 hours under reduced pressure.
  • Solvates, pseudomorphs and hydrates of crystalline forms of the present invention are also included within the scope of the present invention.
  • Crystalline lurasidone hydrochloride of the present invention may be administered as part of a pharmaceutical composition for the treatment of schizophrenia. Accordingly, in a further aspect, there is provided a pharmaceutical composition comprising crystalline lurasidone hydrochloride of the present invention, one or more pharmaceutically acceptable carriers, diluents or excipients, and optionally other therapeutic ingredients. Crystalline lurasidone hydrochloride of the present invention may conventionally be formulated into tablets, capsules, suspensions, dispersions, injectables and other pharmaceutical forms. Any suitable route of administration may be employed, for example, peroral or parental.
  • X-ray diffraction patterns were recorded using Panalytical Expert PRO with Xcelerator as detector, 3-40 as scan range, 0.02 as step size and 3-40° 2 ⁇ as range.
  • HPLC purity was determined by using a YMC Pack ODS-AM (250x4.6)mm, 5 ⁇ column with a flow rate: 1.5 mL/minute; column oven temperature: 45°C; detector: UV at 230nm; injection volume: 10 ⁇ ; run time: 37 minutes, using buffer and acetonitrile as diluent and 1 mL o-phosphoric acid + 100 mL water as buffer.
  • Lurasidone (10 g) was added to 2-propanol (100 mL) at ambient temperature.
  • the reaction mixture was cooled to about 0°C to about 10°C.
  • 7% Aqueous hydrochloric acid solution was slowly added.
  • the reaction mixture was stirred at about 5°C to about 15°C for about 4 hours and 30 minutes.
  • the solid thus obtained, was filtered, washed with 2- propanol (2 x 10 mL) and dried at about 45°C under reduced pressure for about 17 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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 porte sur du chlorhydrate de lurasidone cristallin, sur des procédés pour sa préparation, sur une composition pharmaceutique le comprenant et sur son utilisation pour le traitement de la schizophrénie.
PCT/IB2012/054248 2011-08-26 2012-08-22 Chlorhydrate de lurasidone cristallin WO2013030722A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2438DE2011 2011-08-26
IN2438/DEL/2011 2011-08-26

Publications (1)

Publication Number Publication Date
WO2013030722A1 true WO2013030722A1 (fr) 2013-03-07

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Application Number Title Priority Date Filing Date
PCT/IB2012/054248 WO2013030722A1 (fr) 2011-08-26 2012-08-22 Chlorhydrate de lurasidone cristallin

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WO (1) WO2013030722A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013190455A2 (fr) * 2012-06-18 2013-12-27 Shasun Pharmaceuticals Limited Procédé pour la préparation de chlorhydrate de lurasidone
US9790237B2 (en) 2014-06-16 2017-10-17 Johnson Matthey Public Limited Company Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates
EP3207041A4 (fr) * 2014-10-14 2018-09-26 Jubilant Generics Limited (Formerly Jubilant Life Sciences Division) Procédé amélioré de préparation de chlorhydrate de lurasidone
CN110003195A (zh) * 2019-05-21 2019-07-12 湖北中医药大学 鲁拉西酮晶体及其制备方法和在注射给药系统中的应用
CN111978315A (zh) * 2020-09-02 2020-11-24 中国药科大学 盐酸鲁拉西酮色氨酸/l-脯氨酸共无定形物及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532372A (en) 1990-07-06 1996-07-02 Sumitomo Pharmaceuticals Company, Ltd. Imide derivatives, and their production and use
US7605260B2 (en) 2003-07-29 2009-10-20 Dainippon Sumitomo Pharma Co., Ltd. Process for producing imide compound
WO2012107890A2 (fr) * 2011-02-10 2012-08-16 Ranbaxy Laboratories Limited Formes cristallines de chlorhydrate de lurasidone

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5532372A (en) 1990-07-06 1996-07-02 Sumitomo Pharmaceuticals Company, Ltd. Imide derivatives, and their production and use
US7605260B2 (en) 2003-07-29 2009-10-20 Dainippon Sumitomo Pharma Co., Ltd. Process for producing imide compound
WO2012107890A2 (fr) * 2011-02-10 2012-08-16 Ranbaxy Laboratories Limited Formes cristallines de chlorhydrate de lurasidone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JONATHAN M MEYER ET AL: "Lurasidone: a new drug in development for schizophrenia", EXPERT OPINION ON INVESTIGATIONAL DRUGS, vol. 18, no. 11, 1 November 2009 (2009-11-01), pages 1715 - 1726, XP055045247, ISSN: 1354-3784, DOI: 10.1517/13543780903286388 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013190455A2 (fr) * 2012-06-18 2013-12-27 Shasun Pharmaceuticals Limited Procédé pour la préparation de chlorhydrate de lurasidone
WO2013190455A3 (fr) * 2012-06-18 2014-03-20 Shasun Pharmaceuticals Limited Procédé pour la préparation de chlorhydrate de lurasidone
US9790237B2 (en) 2014-06-16 2017-10-17 Johnson Matthey Public Limited Company Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates
US9957283B1 (en) 2014-06-16 2018-05-01 Johnson Matthey Public Limited Company Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates
EP3207041A4 (fr) * 2014-10-14 2018-09-26 Jubilant Generics Limited (Formerly Jubilant Life Sciences Division) Procédé amélioré de préparation de chlorhydrate de lurasidone
CN110003195A (zh) * 2019-05-21 2019-07-12 湖北中医药大学 鲁拉西酮晶体及其制备方法和在注射给药系统中的应用
CN110003195B (zh) * 2019-05-21 2020-05-26 湖北中医药大学 鲁拉西酮晶体及其制备方法和在注射给药系统中的应用
CN111978315A (zh) * 2020-09-02 2020-11-24 中国药科大学 盐酸鲁拉西酮色氨酸/l-脯氨酸共无定形物及其制备方法和应用
CN111978315B (zh) * 2020-09-02 2023-03-24 中国药科大学 盐酸鲁拉西酮色氨酸/l-脯氨酸共无定形物及其制备方法和应用

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