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WO2012051246A1 - Bromhydrate de tapentadol et formes cristallines de celui-ci - Google Patents

Bromhydrate de tapentadol et formes cristallines de celui-ci Download PDF

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Publication number
WO2012051246A1
WO2012051246A1 PCT/US2011/055893 US2011055893W WO2012051246A1 WO 2012051246 A1 WO2012051246 A1 WO 2012051246A1 US 2011055893 W US2011055893 W US 2011055893W WO 2012051246 A1 WO2012051246 A1 WO 2012051246A1
Authority
WO
WIPO (PCT)
Prior art keywords
tapentadol
hydrobromide
tapentadol hydrobromide
salt
crystalline
Prior art date
Application number
PCT/US2011/055893
Other languages
English (en)
Inventor
Alexandre Mathieu
Original Assignee
Ratiopharm Gmbh
Teva Pharmaceuticals Usa, 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 Ratiopharm Gmbh, Teva Pharmaceuticals Usa, Inc. filed Critical Ratiopharm Gmbh
Publication of WO2012051246A1 publication Critical patent/WO2012051246A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention concerns the hydrobromide salt of Tapentadol, solid state forms of Tapentadol hydrobromide, processes for their preparation, and pharmaceutical
  • compositions comprising Tapentadol hydrobromde or a solid state form thereof.
  • Tapentadol is marketed under the trade name Nucynta for the treatment of moderate to severe pain.
  • EP 1390023 discloses pharmaceutical salts of 1- phenyl-3-dimethylamino-propane compounds and sugar substitutes.
  • International patent application publication no. WO2008/110323 discloses the salts of l-phenyl-3- dimemylamino-propane and their use in treating neuropathic pain.
  • Different salts of an active pharmaceutical ingredient may possess different properties. Such variations in the properties of different salts may provide a basis for improving formulation. Different salts of an active pharmaceutical ingredient may also give rise to a variety of polymorphs or crystalline forms.
  • Polymorphism the occurrence of different crystal forms, is a property of some molecules and molecular complexes.
  • a single molecule like Tapentadol and its salts, may give rise to a variety of polymorphs having distinct crystal structures and physical properties like melting point, thermal behaviours (e.g., measured by capillary melting point, thermogravimetric analysis (TGA), or differential scanning calorimetry (DSC), as well as content of solvent in the polymorphic form), powder x-ray diffraction pattern (PXRD), infrared absorption and Raman fingerprints, and solid state NMR spectrum.
  • TGA thermogravimetric analysis
  • DSC differential scanning calorimetry
  • PXRD powder x-ray diffraction pattern
  • Raman fingerprints solid state NMR spectrum
  • polymorphs are distinct solids sharing the same molecular formula yet having distinct physical properties compared to other polymorphic forms of the same compound or complex.
  • the present invention provides a salt of Tapentadol, Tapentadol hydrobromide, isolated and solid state forms of Tapentadol hydrobromide, and provides pharmaceutical compositions comprising Tapentadol hydrobromide or at least one solid state form (or solid state forms) thereof, and at least one pharmaceutically acceptable excipient.
  • the solid state forms of Tapentadol hydrobromide include the hydrates and solvates of Tapentadol hydrobromide.
  • the invention further provides the use of Tapentadol hydrobromide, and the solid state forms described below for the manufacture of a medicament for the treatment of moderate to severe pain, and provides for a method of treatment of moderate to severe pain comprising administering a therapeutically effective dose of at least one of the solid state forms described herein to a person suffering from moderate to severe pain.
  • the invention provides a method for treating moderate to severe pain comprising administering the pharmaceutical composition comprising Tapentadol hydrobromide or at least one solid state form thereof and at least one pharmaceutically acceptable excipient.
  • Figure 1 shows a powder XRD pattern of Tapentadol hydrobromide.
  • Figure 2 shows a DSC thermogram of Tapentadol hydrobromide.
  • Figure 3 shows a powder XRD pattern of Tapentadol free base.
  • a crystal form may be referred to herein as being characterized by graphical data "as shown in,” or “as depicted in,” or “substantially as depicted in” a Figure.
  • Such data include, for example, powder X-ray diffractograms and solid state NMR spectra.
  • the skilled person will understand that such graphical representations of data may be subject to small variations, e.g., in peak relative intensities and peak positions due to factors such as variations in instrument response and variations in sample concentration and purity, which are well known to the skilled person. Nonetheless, the skilled person would readily be capable of comparing the graphical data in the Figure disclosed herein with graphical data generated for an unknown crystal form, and confirm whether the two sets of data are characterizing the same crystal form or two different crystal forms.
  • the crystal form characterized by the graphical data "as shown in,” or “as depicted in,” or “substantially as depicted in” a Figure disclosed herein includes a crystal form characterized by graphical data with small variations, which are well known to the skilled person, in comparison to the graphical data in the Figure.
  • a crystal form, crystalline form or polymorph may be referred to herein as pure or polymorphically pure, or substantially free of any other crystalline or polymorphic forms.
  • the expression “substantially free” will be understood to mean that the crystalline form contains 20% or less, 10% or less, 5% or less, 2% or less, or 1% or less of any other crystalline forms of the subject compound as measured, for example, by PXRD.
  • crystalline forms of Tapentadol salts described herein as substantially free of any other crystalline forms would be understood to contain greater than 80% (w/w), greater than 90% (w/w), greater than 95% (w/w), greater than 98% (w/w), or greater than 99% (w/w) of the subject crystalline form of Tapentadol salt. Accordingly, in some embodiments of the invention, the described crystalline form may contain from 1% to 20% (w/w), from 5% to 20% (w/w), or from 5% to 10% (w/w) of one or more other crystal forms of the same compound.
  • the present invention provides Tapentadol hydrobromide.
  • the Tapentadol hydrobromide of the present invention can be crystalline.
  • the present invention provides a crystalline form of Tapentadol hydrobromide characterized by data selected from: a powder XRD pattern with peaks at 9.9, 14.3, 15.3, 19.1 and 20.9 + 0.2° 2 ⁇ ; apowder XRD pattern substantially as depicted in Figure 1; a DSC thermogram substantially as depicted in Figure 2; and any combinations thereof.
  • a person skilled in the art would be able to characterize the above form by identifying one or more characteristic peaks in a powder X-ray diffraction analysis of that form.
  • the skilled person would be able to characterize the above form by selecting one or more characteristic peaks in the diffractogram provided in Figure 1.
  • the Tapentadol hydrobromide salt and its crystalline forms in the present invention have advantageous properties selected from at least one of: high crystallinity, solubility, dissolution rate, morphology, thermal and mechanical stability to polymorphic conversion and/or to dehydration, storage stability, low content of residual solvent, a lower degree of hygroscopicity, flowability, and advantageous processing and handling characteristics such as compressibility, and bulk density.
  • These properties may provide a basis for improving formulation, for example, by facilitating better processing or handling characteristics, improving the dissolution profile, or improving stability and shelf-life. They may also provide improvements to the final dosage form, for instance, if they serve to improve bioavailability, or shelf-live or storage etc.
  • the present invention further encompasses 1) a pharmaceutical composition comprising Tapentadol hydrobromide salt, or a composition comprising at least one solid state form of Tapentadol hydrobromide, as described above, and at least one
  • Tapentadol hydrobromide salt and its solid state forms to a subject in need of the treatment.
  • the pharmaceutical composition can be useful for preparing a medicament.
  • the present invention also provides Tapentadol hydrobromide salt or at least one of its solid state forms as described above for use as a medicament.
  • the Tapentadol hydrobromide and its crystalline forms of the present invention are useful for preparing different Tapentadol salts or Tapentadol free base.
  • the above described salt of Tapentadol, Tapentadol hydrobromide, and in particular the above described crystalline forms of Tapentadol hydrobromide can be used to prepare a pharmaceutical composition.
  • Such pharmaceutical compositions can be useful for treating pain, such as moderate to severe pain.
  • the samples were, if necessary, ground in an agate mortar and properly prepared (flatted surface in zO) on a specimen holder made from PMMA.
  • the samples were then analyzed on a Bruker-AXS D8 Advance powder X-ray diffractometer (Bruker-AXS, Düsseldorf, Germany).
  • the specimen holder was rotated in the zO plane at 20 rpm during measurement.
  • the measurement conditions were as follows: Radiation: Cu Ka of wavelength 1.54A , Source 40 kV / 40 mA, divergence slit 0.6 mm, detector: Vantec-1 anti- scattering slit 5.59 mm, detector slit 10.28 mm, start angle 3°2Theta, end angle 55°2Theta, Step 0.017° 2Theta.
  • Raw data were evaluated using the program EVA (Brulcer-AXS, Düsseldorf, Germany).
  • DSC Differential scanning calorimetry
  • a Mettler Toledo 822e DSC instrument was used to record the DSC curves. A sample amount of approx. 3.6 mg was placed in the calorimeter cell and heated from 30°C to 300°C with a rate of 10°C/min and a nitrogen flow of 50 ml/min.
  • Methoxy-Tapentadol hydrochloride (1 eq) was set free as Tapentadol base with 8 eq aqueous hydrobromic acid (47%) under reflux and subsequently sodium bicarbonate was added until pH 8 to 9 was reached. The solution was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulphate and distilled under reduced pressure.
  • Tapentadol base (0.52 g, 2.35 mmol) was dissolved in acetone (5 ml) at room temperature.
  • aqueous hydrobromic acid (47 wt.%, 1.21 g, 7 mmol) was added and the mixture was thereafter kept in the fumehood for 3 days in an open flask.
  • a solid precipitate formed and was separated out and filtered.
  • the solid material was washed with acetone, and dried overnight at 40 mbars and 40°C yielding tapentadol hydrobromide 0.38 g crystals (1.3 mmol, 53.5 %yield).
  • Example 4 Preparation of Tapentadol hydrochloride from Tapentadol hydrobromide Tapentadol hydrobromide was dissolved in acetone. Gaseous hydrogen chloride was bubbled through this clear solution, and the precipitate that formed was then filtered off.
  • Tapentadol base (1 eq) was dissolved in 2-butanone at room temperature. To this solution, 1 eq of trimethylsilyl bromide and leq of water were added. Tapentadol hydrobromide crystallized overnight in an open flask resultmg in a solid form, which did not undergo polymorphic conversion.
  • Tapentadol base (1 eq) was dissolved in 2-butanone at room temperature. To this solution, 1 eq of trimethylsilyl chloride and leq of water were added, whereupon Tapentadol hydrochloride crystallized. Depending on ambient conditions, either polymorphic Form A or Form B or mixtures thereof were obtained.
  • Tapentadol base (1 eq) was dissolved in an organic solvent selected from acetone, hexane, 2-butanone, diethylether, and butanol.
  • An acid (1 eq) selected from the table below was dissolved in the same solvent. The two solutions were combined and heated to about

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne un sel de Tapentadol, du bromhydrate de Tapentadol, et des formes cristallines de bromhydrate de Tapentadol.
PCT/US2011/055893 2010-10-12 2011-10-12 Bromhydrate de tapentadol et formes cristallines de celui-ci WO2012051246A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US39230810P 2010-10-12 2010-10-12
US61/392,308 2010-10-12

Publications (1)

Publication Number Publication Date
WO2012051246A1 true WO2012051246A1 (fr) 2012-04-19

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013120466A1 (fr) * 2012-02-17 2013-08-22 Zentiva, K.S. Nouvelle forme solide du tapentadol et procédé pour sa préparation
WO2015075678A1 (fr) * 2013-11-21 2015-05-28 Unimark Remedies Ltd. Nouveau procédé pour la préparation de dérivés de 1-phényl-3-aminopropane
WO2015117576A1 (fr) 2014-02-04 2015-08-13 Zentiva, K.S. Forme solide du maléate de tapentadol et son procédé de préparation
GB2523089A (en) * 2014-02-12 2015-08-19 Azad Pharmaceutical Ingredients Ag Stable polymorph form B of tapentadol hydrochloride
WO2017085734A1 (fr) * 2015-11-17 2017-05-26 Msn Laboratories Private Limited Formes cristallines de sels de tapentadol et leur procédé de préparation
WO2017182438A1 (fr) 2016-04-19 2017-10-26 Ratiopharm Gmbh Phosphate de tapentadol cristallin
EP3287447A1 (fr) * 2010-07-23 2018-02-28 Grünenthal GmbH Sels ou co-cristaux de 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)- phénol
DE202021100040U1 (de) 2020-07-24 2021-08-16 Grünenthal GmbH Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure
EP3875080A1 (fr) 2020-03-02 2021-09-08 Grünenthal GmbH Forme posologique à libération prolongée de sel d'acide phosphorique de tapentadol
EP3875077A1 (fr) 2020-03-02 2021-09-08 Grünenthal GmbH Forme posologique à libération prolongée de sel d'acide phosphorique de tapentadol
WO2021175773A1 (fr) 2020-03-02 2021-09-10 Grünenthal GmbH Forme posologique assurant une libération prolongée de sel d'acide phosphorique de tapentadol

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0693475A1 (fr) 1994-07-23 1996-01-24 Grünenthal GmbH Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique
EP1390023A2 (fr) 2001-02-28 2004-02-25 Grünenthal GmbH Sels pharmaceutiques
EP1612203A1 (fr) 2004-06-28 2006-01-04 Grünenthal GmbH Formes cristallines de chlorhydrate de (-)-(1R,2R)-3-(3-diméthylamino-1-ethyl-2-méthylpropyl)-phénol
WO2008110323A1 (fr) 2007-03-12 2008-09-18 Grünenthal GmbH Utilisation de composés de 1-phényl-3-diméthylamino-propane pour traiter la douleur neuropathique
WO2009071310A1 (fr) 2007-12-07 2009-06-11 Grünenthal GmbH Modifications cristallines de (1r,2r)-3-(3-diméthylamino-1-éthyl-2-méthyl-propyl)-phénol
US20100190752A1 (en) * 2008-09-05 2010-07-29 Gruenenthal Gmbh Pharmaceutical Combination
WO2010096045A1 (fr) * 2008-10-30 2010-08-26 Nectid, Inc. Nouvelles formes galéniques puissantes du tapentadol
US20110071120A1 (en) * 2009-09-22 2011-03-24 Actavis Group Ptc Ehf Solid state forms of tapentadol salts

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0693475A1 (fr) 1994-07-23 1996-01-24 Grünenthal GmbH Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique
US6248737B1 (en) 1994-07-23 2001-06-19 Gruenenthal Gmbh 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
EP1390023A2 (fr) 2001-02-28 2004-02-25 Grünenthal GmbH Sels pharmaceutiques
EP1612203A1 (fr) 2004-06-28 2006-01-04 Grünenthal GmbH Formes cristallines de chlorhydrate de (-)-(1R,2R)-3-(3-diméthylamino-1-ethyl-2-méthylpropyl)-phénol
WO2008110323A1 (fr) 2007-03-12 2008-09-18 Grünenthal GmbH Utilisation de composés de 1-phényl-3-diméthylamino-propane pour traiter la douleur neuropathique
WO2009071310A1 (fr) 2007-12-07 2009-06-11 Grünenthal GmbH Modifications cristallines de (1r,2r)-3-(3-diméthylamino-1-éthyl-2-méthyl-propyl)-phénol
US20100190752A1 (en) * 2008-09-05 2010-07-29 Gruenenthal Gmbh Pharmaceutical Combination
WO2010096045A1 (fr) * 2008-10-30 2010-08-26 Nectid, Inc. Nouvelles formes galéniques puissantes du tapentadol
US20110071120A1 (en) * 2009-09-22 2011-03-24 Actavis Group Ptc Ehf Solid state forms of tapentadol salts

Non-Patent Citations (1)

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Title
WADE W E ET AL: "Tapentadol hydrochloride: A centrally acting oral analgesic", CLINICAL THERAPEUTICS, EXCERPTA MEDICA, PRINCETON, NJ, US, vol. 31, no. 12, 1 December 2009 (2009-12-01), pages 2804 - 2818, XP026872214, ISSN: 0149-2918, [retrieved on 20100112] *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3656765B1 (fr) 2010-07-23 2021-04-14 Grünenthal GmbH Sels ou co-cristaux de 3-(3-dimethylamino-1-éthyl-2-méthyl-propyl)-phénol
EP3287447A1 (fr) * 2010-07-23 2018-02-28 Grünenthal GmbH Sels ou co-cristaux de 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)- phénol
EP3597628A1 (fr) * 2010-07-23 2020-01-22 Grünenthal GmbH Sels ou co-cristaux de 3-(3-dimethylamino-1-éthyl-2-méthyl-propyl)-phénol
EP3636629A1 (fr) * 2010-07-23 2020-04-15 Grünenthal GmbH Sels ou co-cristaux de 3-(3-dimethylamino-1-éthyl-2-méthyl-propyl)-phénol
WO2013120466A1 (fr) * 2012-02-17 2013-08-22 Zentiva, K.S. Nouvelle forme solide du tapentadol et procédé pour sa préparation
WO2015075678A1 (fr) * 2013-11-21 2015-05-28 Unimark Remedies Ltd. Nouveau procédé pour la préparation de dérivés de 1-phényl-3-aminopropane
WO2015117576A1 (fr) 2014-02-04 2015-08-13 Zentiva, K.S. Forme solide du maléate de tapentadol et son procédé de préparation
GB2523089A (en) * 2014-02-12 2015-08-19 Azad Pharmaceutical Ingredients Ag Stable polymorph form B of tapentadol hydrochloride
EP3377049B1 (fr) 2015-11-17 2021-01-06 MSN Laboratories Private Limited Formes cristallines de sels de tapentadol et leur procédé de préparation
WO2017085734A1 (fr) * 2015-11-17 2017-05-26 Msn Laboratories Private Limited Formes cristallines de sels de tapentadol et leur procédé de préparation
EP3377049A4 (fr) * 2015-11-17 2019-06-12 MSN Laboratories Private Limited Formes cristallines de sels de tapentadol et leur procédé de préparation
EP3653599A1 (fr) 2016-04-19 2020-05-20 ratiopharm GmbH Phosphate tapentadol cristallin
WO2017182438A1 (fr) 2016-04-19 2017-10-26 Ratiopharm Gmbh Phosphate de tapentadol cristallin
EP3819287A1 (fr) 2016-04-19 2021-05-12 ratiopharm GmbH Phosphate tapentadol amorphe
EP3875080A1 (fr) 2020-03-02 2021-09-08 Grünenthal GmbH Forme posologique à libération prolongée de sel d'acide phosphorique de tapentadol
EP3875079A1 (fr) 2020-03-02 2021-09-08 Grünenthal GmbH Forme posologique fournissant une libération prolongée de sel d'acide phosphorique de tapentadol
EP3875077A1 (fr) 2020-03-02 2021-09-08 Grünenthal GmbH Forme posologique à libération prolongée de sel d'acide phosphorique de tapentadol
WO2021175773A1 (fr) 2020-03-02 2021-09-10 Grünenthal GmbH Forme posologique assurant une libération prolongée de sel d'acide phosphorique de tapentadol
DE202021003994U1 (de) 2020-03-02 2022-04-12 Grünenthal GmbH Dosierungsform mit verlängerter Freisetzung von Tapentadol-Phosphorsäuresalz
DE202021100040U1 (de) 2020-07-24 2021-08-16 Grünenthal GmbH Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure
DE202021100039U1 (de) 2020-07-24 2021-09-30 Grünenthal GmbH Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure
DE102021119130A1 (de) 2020-07-24 2022-01-27 Grünenthal GmbH Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure

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