WO2006082598A2 - Nouvelles formes cristallines de rizatriptane benzoate - Google Patents

Nouvelles formes cristallines de rizatriptane benzoate Download PDF

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Publication number
WO2006082598A2
WO2006082598A2 PCT/IN2006/000028 IN2006000028W WO2006082598A2 WO 2006082598 A2 WO2006082598 A2 WO 2006082598A2 IN 2006000028 W IN2006000028 W IN 2006000028W WO 2006082598 A2 WO2006082598 A2 WO 2006082598A2
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WO
WIPO (PCT)
Prior art keywords
rizatriptan benzoate
rizatriptan
solvent
benzoate
process according
Prior art date
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PCT/IN2006/000028
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English (en)
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WO2006082598A3 (fr
Inventor
Muddasani Pulla Reddy
Hanumara Satyasrinivas
Nannapaneni Venkaiah Chowdary
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Natco Pharma Limited
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Publication date
Application filed by Natco Pharma Limited filed Critical Natco Pharma Limited
Publication of WO2006082598A2 publication Critical patent/WO2006082598A2/fr
Publication of WO2006082598A3 publication Critical patent/WO2006082598A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • Present invention relates to novel crystalline forms of rizatriptan benzoate, process for their preparation and pharmaceutical compositions containing them.
  • Patent EP 497512 describes derivatives of imidazole, triazole, and tetrazole, which act, on 5-HT receptor. Notable among them is the compound 3-(2-(dimethylamino)ethyl)-5- (1 ,2,4-triazol- 1 -ylmethyl)-indole, of formula-I,
  • This compound is known by the INN rizatriptan and is marketed as an anti-migraine product.
  • EP 497512 also discloses the benzoate salt as suitable for pharmaceutical preparations. No crystalline forms of rizatriptan benzoate were reported.
  • the main objective of the present invention is to provide stable, novel crystalline forms of rizatriptan benzoate, process for preparation of the novel crystalline forms and pharmaceutical compositions containing these novel crystalline forms.
  • a novel crystalline form of rizatriptan benzoate designated as Form I, characterized by an X-ray powder diffraction pattern having peaks expressed as 2 ⁇ 9.10, 12.81, 15.84, 16.98, 17.74, 18.38, 18.81, 19.23, 20.98, 22.15, 22.65, 23.86, 24.96, 26.09, and 29.18 degrees.
  • Figure 1 shows typical Form I X-ray powder diffraction pattern.
  • a process for preparation of Form I of rizatriptan benzoate is provided.
  • rizatriptan of formula I is dissolved in methanol and benzoic acid is added to the solution.
  • the Form I of rizatriptan benzoate is crystallized from the solution by techniques such as cooling, partial removal of solvent or addition of anti-solvent and isolated by conventional techniques such as filtration.
  • rizatriptan benzoate a process for the preparation of Form I of rizatriptan benzoate.
  • rizatriptan of formula I is dissolved in acetone and benzoic acid is added to the solution.
  • the resultant rizatriptan benzoate is isolated by filtration.
  • This salt is recrystallized from alcoholic solvents such as methanol, ethanol, isopropanol, isobutanol to get Form I crystals of rizatriptan benzoate.
  • the rizatriptan benzoate described in, for example EP 497512 or other forms of rizatriptan benzoate may be used.
  • a novel crystalline form of rizatriptan benzoate designated as Form II, characterized by an X-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 8.23, 9.14, 11.58, 12.82, 14.48, 15.89, 16.49, 17.03, 17.77, 18.44, 18.84, 19.30, 20.23, 21.00, 22.16, 22.71, 23.32, 23.87, 25.00, 26.19, 28.85, 31.59, and 32.00 degrees.
  • Figure 2 shows the typical Form II X-ray powder diffraction pattern.
  • a process for the preparation of Form II of rizatriptan benzoate is provided.
  • rizatriptan of formula I is dissolved in a suitable solvent and benzoic acid is added to the solution.
  • the Form II of rizatriptan benzoate is crystallized from the solution by techniques such as cooling, partial removal of solvent.
  • the suitable solvent is selected from a group consisting of acetone, methyl ethyl ketone, 3-propanone, methyl isobutyl ketone, methyl tert-butyl ketone, tetrahydrofuran, preferably acetone or methyl ethyl ketone.
  • rizatriptan benzoate prepared by the process described in, for example EP 497512 or other forms of rizatriptan benzoate (preparation by the process described below) is dissolved in a solvent selected from a group consisting of acetone, methyl ethyl ketone, 3-propanone, methyl isobutyl ketone, methyl tert-butyl ketone, preferably acetone or methyl ethyl ketone acetone at reflux temperature.
  • a solvent selected from a group consisting of acetone, methyl ethyl ketone, 3-propanone, methyl isobutyl ketone, methyl tert-butyl ketone, preferably acetone or methyl ethyl ketone acetone at reflux temperature.
  • a novel crystalline form of rizatriptan benzoate designated as Form III, characterized by an X-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 8.02, 8.94, 11.38, 12.61, 13.34, 15.69, 16.29, 16.84, 17.65, 18.21, 18.65, 19.09, 20.01, 20.81, 21.97, 22.51, 23.12, 23.69, 24.80, 26.02, 27.02, 28.63, and 31.41 degrees.
  • Figure 3 shows the typical Form III X-ray powder diffraction pattern.
  • rizatriptan benzoate prepared by the process. described in, for example EP 497512 or other forms of rizatriptan benzoate (preparation by the process described below) is dissolved in water. Water is removed from the reaction mass by techniques such as freeze-drying, spray drying, or vaccum distillation to get the Form III crystals of rizatriptan benzoate.
  • the Form III crystals of of rizatriptan benzoate are isolated from the reaction mass by cooling, partial removal of solvent or addition of anti-solvent.
  • the suitable anti-solvent for isolation includes alcohols like methanol, ethanol, isopropanol, ketones like acetone, methyl ethyl ketone, nitriles like acetonitrile.
  • a pharmaceutical composition comprising Form I or From II or Form III of rizatriptan benzoate.
  • the forms of rizatriptan benzoate may be formulated in a form suitable for oral administration or injection.
  • Figure 1 is an X-ray powder diffraction pattern of Form I rizatriptan benzoate.
  • Figure 2 is an X-ray powder diffraction pattern of Form II rizatriptan benzoate.
  • Figure 3 is an X-ray powder diffraction pattern of Form III rizatriptan benzoate.
  • X-ray powder diffraction spectra were measured on a Siemens D5000 x-ray powder diffractometer having a copper-K ⁇ radiation (1.5406A).
  • Rizatriptan (5g) was taken into a 250-ml, three-necked RB flask and added methanol (30ml). The reaction mass heated to reflux temperature to get a clear solution. Solid benzoic acid (2.3g) was added to the reaction mass all at once. After maintaining at reflux for lOmin, reaction mass was allowed to cool to 25-30 0 C. The reaction mass was further cooled to 0-5 0 C and maintained for lhr. Rizatriptan benzoate was isolated by filtration and dried the wet compound at 50-60 0 C to give Form I of rizatriptan benzoate.
  • Example 2 Rizatriptan (5g) was taken into a 250-ml, three-necked RB flask and added acetone (50 ml). The reaction mass heated to reflux temperature to get a clear solution. Solid benzoic acid (2.3g) was added to the reaction mass all at once. After maintaining at reflux for lOmin, reaction mass was allowed to cool to 25-30 0 C. The reaction mass was maintained for lhr. Rizatriptan benzoate was isolated by filtration and dried the wet compound at 50- 60 0 C to give Form II of rizatriptan benzoate.
  • Rizatriptan (5g) was taken into a 100-ml, three-necked RB flask and added water (150 ml). Solid benzoic acid (2.3g) was added to the reaction mass all at once. The reaction mass was heated to 60-70 0 C and maintained for 30min. Water was removed from the reaction mass by freeze-drying technique to get Form III of rizatriptan benzoate.
  • Rizatriptan benzoate (5g) prepared according to Example 1 above was taken into a 100- ml, three-necked RB flask and added water (15ml). The reaction mass heated to 60-70 0 C temperature to get a clear solution. The reaction mass was cooled to 5-10 °C and maintained for lhr. Rizatriptan benzoate was isolated by filtration and dried the wet compound at 50-60 0 C to get Form II of rizatriptan benzoate.
  • Example 5 Rizatriptan (5g) was taken into a 250-ml, three-necked RB flask and added tetrahydrofuran (30 ml). The reaction mass heated to reflux temperature to get a clear solution. Solid benzoic acid (2.3 g) was added to the reaction mass all at once After maintaining at reflux for lOmin reaction mass was allowed to cool to 25-30 0 C. Rizatriptan benzoate was isolated by filtration and dried the wet compound at 50-60 °C to get Form II of rizatriptan benzoate.
  • reaction mass (30ml). The reaction mass heated to reflux temperature to get a clear solution. Solid benzoic acid (2.3 g) was added to the reaction mass all at once. After maintaining at reflux for lOmin, reaction mass was allowed to cool to 40-45 0 C. The reaction mass was maintained at 40-45 0 C for 2hr. Rizatriptan benzoate was isolated by filtration and dried the wet compound at 50-60 0 C to get Form I of rizatriptan benzoate.
  • Rizatriptan benzoate (10Og) prepared according to the process described in Example 2 above was dissolved in ethanol (700ml) at reflux temperature.
  • Activated carbon (1Og) was added to the solution and filtered while hot.
  • the filter bed was washed with 200ml of hot ethanol.
  • the combined filtrate was gradually cooled to 0-5 0 C and maintained for lhr.
  • reaction mass was filtered and the wet cake dried at 50-60 0 C to get 85g of white
  • Present invention discloses three novel crystalline forms, designated as Form I, Form II, and Form III of rizatriptan benzoate.
  • Novel crystalline forms of rizatriptan benzoate disclosed in present invention are stable and suitable for pharmaceutical formulations.

Abstract

La présente invention a trait à de nouvelles formes cristallines, désignées Forme I, II, et III de rizatriptane benzoate, leur procédé de préparation et des compositions pharmaceutiques les contenant.
PCT/IN2006/000028 2005-02-01 2006-01-27 Nouvelles formes cristallines de rizatriptane benzoate WO2006082598A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN82CH2005 2005-02-01
IN82/CHE/2005 2005-02-01

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WO2006082598A2 true WO2006082598A2 (fr) 2006-08-10
WO2006082598A3 WO2006082598A3 (fr) 2006-10-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017130141A1 (fr) 2016-01-27 2017-08-03 Instar Technologies A.S. Supports nanofibreux oromumuqueux pour traitement thérapeutique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0497512A2 (fr) * 1991-02-01 1992-08-05 Merck Sharp & Dohme Ltd. Dérivés d'imidazole, triazole et tétrazole
US5567824A (en) * 1994-05-24 1996-10-22 Merck & Co., Inc. Palladium catalyzed ring closure of triazolyltryptamine
GB2315673A (en) * 1996-08-01 1998-02-11 Merck & Co Inc Treatment of migraine
WO2005068453A2 (fr) * 2004-01-09 2005-07-28 Ratiopharm Gmbh Formes cristallines de benzoate de rizatriptan

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0497512A2 (fr) * 1991-02-01 1992-08-05 Merck Sharp & Dohme Ltd. Dérivés d'imidazole, triazole et tétrazole
US5567824A (en) * 1994-05-24 1996-10-22 Merck & Co., Inc. Palladium catalyzed ring closure of triazolyltryptamine
GB2315673A (en) * 1996-08-01 1998-02-11 Merck & Co Inc Treatment of migraine
WO2005068453A2 (fr) * 2004-01-09 2005-07-28 Ratiopharm Gmbh Formes cristallines de benzoate de rizatriptan

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017130141A1 (fr) 2016-01-27 2017-08-03 Instar Technologies A.S. Supports nanofibreux oromumuqueux pour traitement thérapeutique

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