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WO2004099140A1 - Nouvelles formes cristallines de succinate de sumatriptan - Google Patents

Nouvelles formes cristallines de succinate de sumatriptan Download PDF

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Publication number
WO2004099140A1
WO2004099140A1 PCT/IN2003/000180 IN0300180W WO2004099140A1 WO 2004099140 A1 WO2004099140 A1 WO 2004099140A1 IN 0300180 W IN0300180 W IN 0300180W WO 2004099140 A1 WO2004099140 A1 WO 2004099140A1
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WO
WIPO (PCT)
Prior art keywords
sumatriptan succinate
sumatriptan
succinate form
methyl
tert
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IN2003/000180
Other languages
English (en)
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Kesireddy Subash Chander Reddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hetero Drugs Ltd
Original Assignee
Hetero Drugs Ltd
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 Hetero Drugs Ltd filed Critical Hetero Drugs Ltd
Priority to PCT/IN2003/000180 priority Critical patent/WO2004099140A1/fr
Priority to AU2003238678A priority patent/AU2003238678A1/en
Publication of WO2004099140A1 publication Critical patent/WO2004099140A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Definitions

  • the present invention relates to novel crystalline forms of sumatriptan succinate, to processes for their preparation and to pharmaceutical compositions containing them.
  • Sumatriptan succinate is a selective 5-Hydroxy tryptamine-i receptor subtype agonist.
  • Sumatriptan succinate is chemically designated as 3-[2- (dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide succinate (1:1).
  • Sumatriptan succinate is currently used in the treatment of migraine.
  • Sumatriptan is represented by the following structure:
  • sumatriptan succinate can be prepared in two well-defined, stable and consistently reproducible crystalline forms.
  • the object of the present invention is to provide stable, consistently reproducible crystalline forms of sumatriptan succinate, processes for preparing these forms and pharmaceutical compositions comprising them.
  • sumatriptan succinate form I a novel crystalline form of sumatriptan succinate.
  • This crystalline form is designated as sumatriptan succinate form I and typical form I x-ray powder diffraction spectrum of sumatriptan succinate form I is shown in figure 1.
  • Sumatriptan succinate form I is characterized by peaks in the powder x- ray diffraction spectrum having two-theta angle positions at about 9.3, 12.4, 12.8, 13.4, 15.6, 15.8, 16.3, 16.5, 18.2, 19.0, 20.0, 20.4, 20.7, 21.5, 22.2, 22.9, 26.1 , 27.1, 28.7 and 29.8 degrees.
  • Sumatriptan succinate form I is prepared by dissolving sumatriptan free base in a suitable solvent, adding succinic acid to the solution and then isolating sumatriptan succinate form I from the solution.
  • Sumatriptan free base may be dissolved in a sufficient volume of the suitable solvent at elevated temperature (up to reflux).
  • the amount of succinic acid is not critical, but 0.5 - 2.0 moles per mole of sumatriptan free base is preferable.
  • the 'suitable solvents' are selected from acetone, diethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, methyl propyl ketone, methanol, ethanol, isopropyl alcohol, tert-butyl alcohol, n-butyl alcohol, tetrahydrofuran, ethyl acetate, methyl acetate, isopropyl acetate, tert-butyl acetate, ethyl formate, methyl formate, diethyl ether, diisopropyl ether and tert-butyl methyl ether.
  • a mixture of these solvents may also be used.
  • sumatriptan succinate form II a novel crystalline form of sumatriptan succinate.
  • This crystalline form is designated as sumatriptan succinate form II and typical form II x-ray powder diffraction spectrum of sumatriptan succinate form II is shown in figure 2.
  • Sumatriptan succinate form II is characterized by peaks in the powder x- ray diffraction spectrum having two-theta angle positions at about 6.2, 7.7, 13.9, 15.1, 17.5, 17.9, 19.1, 19.4, 20.3, 20.8, 21.5, 22.4, 23.2, 23.9, 26.4 and 31.8 degrees.
  • a process is provided for preparation of sumatriptan succinate form II.
  • Sumatriptan succinate form II is prepared by dissolving sumatriptan free base in a chlorinated solvent, adding succinic acid to the solution and then isolating sumatriptan succinate form II from the solution.
  • Sumatriptan free base may be dissolved in a sufficient volume of the chlorinated solvent at elevated temperature (up to reflux).
  • the amount of succinic acid is not critical, but 0.5 - 2.0 moles per mole of sumatriptan free base is preferable.
  • the chlorinated solvents are selected from methylene dichloride, chloroform, carbon tetrachloride and ethylene dichloride. A mixture of these solvents may also be used. Preferable solvents are chloroform and methylene dichloride.
  • Sumatriptan obtained by a previously known method may be used in the above processes.
  • a pharmaceutical composition comprising sumatriptan succinate form I and a pharmaceutically acceptable carrier or diluent.
  • a pharmaceutical composition comprising sumatriptan succinate form II and a pharmaceutically acceptable carrier or diluent.
  • Figure 1 is a x-ray powder diffraction spectrum of sumatriptan succinate form I.
  • Figure 2 is a x-ray powder diffraction spectrum of sumatriptan succinate form II. x-Ray powder diffraction spectrum was measured on a Bruker axs D8 advance x-ray powder diffractometer having a copper-K ⁇ radiation.
  • Example 1 Sumatriptan free base (5.0 gm) is added to acetone (50 ml), the contents are heated to reflux to form a clear solution and then succinic acid (2.0 gm) is added to the solution. The contents are stirred for 2 hours at reflux temperature, allowed to cool to 25°C and filtered to give 5.6 gm of sumatriptan succinate form I.
  • Example 2 Sumatriptan free base (10.0 gm) is mixed with methanol (120 ml), heated to reflux to form a clear solution and then succinic acid (4.0 gm) is added to the solution. The contents are stirred for 5 hours at reflux temperature, cooled slowly to 25°C and filtered to give 10.8 gm of sumatriptan succinate form I.
  • Example 3 Sumatriptan free base (5.0 gm) is mixed with chloroform (50 ml), the contents are heated to reflux to form a clear solution and then succinic acid (2 gm) is added to the solution. The reaction mixture is stirred for 3 hours at reflux temperature, allowed to cool to 25°C and filtered to give 5.1 gm of sumatriptan succinate form II.
  • Example 4 Sumatriptan free base (10.0 gm) is mixed with methylene dichloride (150 ml), the contents are heated to reflux and then succinic acid (4.0 gm) is added to the clear solution formed. The contents are stirred for 4 hours at reflux temperature, cooled slowly to 25°C and filtered to give 10.5 gm of sumatriptan succinate form II.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention a trait à des nouvelles formes cristallines de succinate de sumatriptan, à leurs procédés de préparation et à des compositions pharmaceutiques les contenant.
PCT/IN2003/000180 2003-05-08 2003-05-08 Nouvelles formes cristallines de succinate de sumatriptan Ceased WO2004099140A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000180 WO2004099140A1 (fr) 2003-05-08 2003-05-08 Nouvelles formes cristallines de succinate de sumatriptan
AU2003238678A AU2003238678A1 (en) 2003-05-08 2003-05-08 Novel crystalline forms of sumatriptan succinate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000180 WO2004099140A1 (fr) 2003-05-08 2003-05-08 Nouvelles formes cristallines de succinate de sumatriptan

Publications (1)

Publication Number Publication Date
WO2004099140A1 true WO2004099140A1 (fr) 2004-11-18

Family

ID=33428279

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000180 Ceased WO2004099140A1 (fr) 2003-05-08 2003-05-08 Nouvelles formes cristallines de succinate de sumatriptan

Country Status (2)

Country Link
AU (1) AU2003238678A1 (fr)
WO (1) WO2004099140A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009128089A3 (fr) * 2008-02-11 2010-03-11 Matrix Laboratories Limited Nouvelle forme de solvate de succinate de sumatriptan et procédé de préparation d'un sel de sumatriptan l'utilisant
US20160263224A1 (en) * 2015-03-09 2016-09-15 Theaprin Pharmaceuticals Inc. Platform drug delivery system utilizing crystal engineering and theanine dissolution

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2162522A (en) * 1984-08-01 1986-02-05 Glaxo Group Ltd An indole derivative
ES2033578A1 (es) * 1991-06-06 1993-03-16 Inke Sa Procedimiento para la obtencion de 3-(2-(dimetilamino)etil)-n-metil-1h-indol-5-metanosulfonamida.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2162522A (en) * 1984-08-01 1986-02-05 Glaxo Group Ltd An indole derivative
ES2033578A1 (es) * 1991-06-06 1993-03-16 Inke Sa Procedimiento para la obtencion de 3-(2-(dimetilamino)etil)-n-metil-1h-indol-5-metanosulfonamida.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009128089A3 (fr) * 2008-02-11 2010-03-11 Matrix Laboratories Limited Nouvelle forme de solvate de succinate de sumatriptan et procédé de préparation d'un sel de sumatriptan l'utilisant
US20160263224A1 (en) * 2015-03-09 2016-09-15 Theaprin Pharmaceuticals Inc. Platform drug delivery system utilizing crystal engineering and theanine dissolution
US9603937B2 (en) * 2015-03-09 2017-03-28 Theaprin Pharmaceuticals Inc. Platform drug delivery system utilizing crystal engineering and theanine dissolution
US12268783B2 (en) 2015-03-09 2025-04-08 Theaprin Pharmaceuticals, Inc. Platform drug delivery system utilizing crystal engineering and theanine dissolution

Also Published As

Publication number Publication date
AU2003238678A1 (en) 2004-11-26

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