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US20090233932A1 - Novel crystalline forms of lamotrigine - Google Patents

Novel crystalline forms of lamotrigine Download PDF

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Publication number
US20090233932A1
US20090233932A1 US12/407,078 US40707809A US2009233932A1 US 20090233932 A1 US20090233932 A1 US 20090233932A1 US 40707809 A US40707809 A US 40707809A US 2009233932 A1 US2009233932 A1 US 2009233932A1
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Prior art keywords
lamotrigine
novel crystalline
present
ray powder
powder diffraction
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US12/407,078
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Reddy bandi Parthasaradhi
Reddy kura Rathnakar
Reddy Rapolu Raji
Reddy dasari Muralidhara
Reddy Kesireddy Subash Chander
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Hetero Drugs Ltd
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Hetero Drugs Ltd
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Priority to US12/407,078 priority Critical patent/US20090233932A1/en
Assigned to HETERO DRUGS LIMITED reassignment HETERO DRUGS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MURALIDHARA REDDY, DASARI, PARTHASARADHI REDDY, BANDI, RAPOLU REDDY, RAJI, RATHNAKAR REDDY, KURA, SUBASH CHANDER REDDY, KESIREDDY
Publication of US20090233932A1 publication Critical patent/US20090233932A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having 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
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine

Definitions

  • the present invention relates to novel crystalline forms of lamotrigine, to processes for their preparation and pharmaceutical compositions containing them.
  • 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine is an anti-epileptic drug and its therapeutic uses are disclosed in U.S. Pat. No. 4,602,017.
  • lamotrigine The novel forms of lamotrigine are, thus, suitable for pharmaceutical preparations.
  • the object of the present invention is to provide stable novel crystalline forms of lamotrigine, to provide a processes for preparation of the novel crystalline forms and to provide a pharmaceutical compositions comprising these novel crystalline forms.
  • FIG. 1 shows typical Form I x-ray powder diffraction pattern.
  • a novel crystalline Form II of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 8.9, 11.2, 12.3, 13.2, 13.9, 17.0, 17.4, 18.0, 18.2, 18.7, 19.8, 21.4, 22.1, 22.7, 25.1, 25.4, 25.7, 26.4, 26.8, 27.1, 27.5, 28.3, 28.8, 29.2, 30.1, 30.9, 31.4, 32.9, 35.3, 35.7, 36.5 degrees.
  • FIG. 2 shows typical Form II x-ray powder diffraction pattern.
  • a novel crystalline Form III of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 9.9, 12.0, 13.3, 16.1, 17.0, 18.1, 18.7, 19.5, 24.4, 26.0, 26.3, 27-6, 28.1, 37.1 degrees.
  • FIG. 3 shows typical Form III x-ray powder diffraction pattern.
  • the ester is selected from the group consisting of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate.
  • composition comprising Form I or Form II or Form III lamotrigine.
  • FIG. 1 is a x-ray powder diffraction pattern of Form I lamotrigine.
  • FIG. 2 is a x-ray powder diffraction pattern of Form II lamotrigine.
  • FIG. 3 is a x-ray powder diffraction pattern of Form III lamotrigine.
  • FIG. 1 shows typical Form I x-ray powder diffraction pattern.
  • a process for preparation of Form I lamotrigine is provided.
  • lamotrigine is dissolved in an ester.
  • the ester is selected from the group consisting of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate.
  • the Form I lamotrigine is maintained at about 15° C. to about 30° C., preferably at about 20° C. to about 25° C., for about 30 minutes to about 2 hours and filtered.
  • Lamotrigine prepared by any of the known methods can be used in the process.
  • Lamotrigine solvate or hydrate may also be used.
  • a novel crystalline Form II lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 8.9, 11.2, 12.3, 13.2, 13.9, 17.0, 17.4, 18.0, 18.2, 18.7, 19.8, 21.4, 22.1, 22.7, 25.1, 25.4, 25.7, 26.4, 26.8, 27.1, 27.5, 28.3, 28.8, 29.2, 30.1, 30.9, 31.4, 32.9, 35.3, 35.7, 36.5 degrees.
  • FIG. 2 shows typical Form II x-ray powder diffraction pattern.
  • a process for preparation of Form II lamotrigine is provided.
  • lamotrigine is dissolved in dioxane and maintained at about 15° C. to about 30° C. for about 1 hour to 3 hours.
  • the separated Form II lamotrigine is filtered.
  • Lamotrigine prepared by any of the known methods can be used in the process.
  • Lamotrigine solvate or hydrate may also be used.
  • a novel crystalline Form III of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 9.9, 12.0, 13.3, 16.1, 17.0, 18.1, 18.7, 19.5, 24.4, 26.0, 26.3, 27.6, 28.1, 37.1 degrees.
  • FIG. 3 shows typical Form III x-ray powder diffraction pattern.
  • a process for preparation of Form III lamotrigine there is provided a process for preparation of Form III lamotrigine.
  • lamotrigine isopropyl acetate, chloroform and dimethyl formamide are mixed and heated to about 60° C. to about 70° C.
  • the contents are maintained for about 30 minutes and cooled to about 20° C. to about 30° C.
  • the Form III lamotrigine is filtered.
  • Lamotrigine prepared by any of the known methods can be used in the process.
  • Lamotrigine solvate or hydrate may also be used.
  • a pharmaceutical composition comprising Form I or Form II or Form III lamotrigine.
  • the forms of lamotrigine may be formulated in a form suitable for oral administration or injection.
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is mixed with ethyl acetate (100 ml) and maintained at about 70° C. for 30 minutes. Then the contents are cooled to about 20° C. The solid is separated by filtration to give 9.0 gm of Form I lamotrigine.
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is added to dioxane (100 ml), maintained at 50° C. to 55° C. for 30 minutes, cooled to 25° C. and maintained at this temperature for 2 hours. The solid is separated by filtration to give 8.5 gm of Form II lamotrigine.
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is added to isopropyl acetate (150 ml) and the contents are heated to about 65° C. Chloroform (50 ml) and dimethyl formamide (48 ml) are added at this temperature and stirred for 30 minutes. The contents are cooled to 25° C. and filtered to give 9.5 gm of Form III lamotrigine.
  • Example 1 is repeated using Form II lamotrigine instead of lamotrigine to give Form I lamotrigine.
  • Example 1 is repeated using Form III lamotrigine instead of lamotrigine to give Form I lamotrigine.
  • Example 2 is repeated using Form III lamotrigine instead of lamotrigine to give Form II lamotrigine.
  • Example 2 is repeated using Form I lamotrigine instead of lamotrigine to give Form II lamotrigine.
  • Example 3 is repeated using Form II lamotrigine instead of lamotrigine to give Form III lamotrigine.
  • Example 3 is repeated using Form I lamotrigine instead of lamotrigine to give Form III lamotrigine.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (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

The present invention relates to novel crystalline forms of lamotrigine, to processes for their preparation and pharmaceutical compositions containing them.

Description

    FIELD OF THE INVENTION
  • The present invention relates to novel crystalline forms of lamotrigine, to processes for their preparation and pharmaceutical compositions containing them.
    • BACKGROUND OF THE INVENTION Lamotrigine of formula (I)
  • Figure US20090233932A1-20090917-C00001
  • or 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine is an anti-epileptic drug and its therapeutic uses are disclosed in U.S. Pat. No. 4,602,017.
  • Different synthetic methods of lamotrigine are described in WO 01/049669, U.S. Pat. No. 6,111,101, U.S. Pat. No. 6,333,198, U.S. Pat. No. 5,912,345, EP 800521, U.S. Pat. No. 4,602,017.
  • Various polymorphic forms are disclosed in WO 02/068398.
  • We have discovered three novel crystalline forms of lamotrigine. The novel forms have been found to be stable over the time and does not automatically convert into other crystalline forms of lamotrigine.
  • The novel forms of lamotrigine are, thus, suitable for pharmaceutical preparations.
  • Thus the object of the present invention is to provide stable novel crystalline forms of lamotrigine, to provide a processes for preparation of the novel crystalline forms and to provide a pharmaceutical compositions comprising these novel crystalline forms.
    • SUMMARY OF THE INVENTION
  • According to one aspect of the present invention, there is provided a novel crystalline Form I of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 12.5, 13.9, 16.7, 18.0, 22.3, 23.6, 26.8, 27.9, 28.5, 28.9, 29.4, 31.7, 40.2, 42.3 degrees. FIG. 1 shows typical Form I x-ray powder diffraction pattern.
  • According to another aspect of the present invention, there is provided a novel crystalline Form II of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 8.9, 11.2, 12.3, 13.2, 13.9, 17.0, 17.4, 18.0, 18.2, 18.7, 19.8, 21.4, 22.1, 22.7, 25.1, 25.4, 25.7, 26.4, 26.8, 27.1, 27.5, 28.3, 28.8, 29.2, 30.1, 30.9, 31.4, 32.9, 35.3, 35.7, 36.5 degrees. FIG. 2 shows typical Form II x-ray powder diffraction pattern.
  • According to another aspect of the present invention, there is provided a novel crystalline Form III of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 9.9, 12.0, 13.3, 16.1, 17.0, 18.1, 18.7, 19.5, 24.4, 26.0, 26.3, 27-6, 28.1, 37.1 degrees. FIG. 3 shows typical Form III x-ray powder diffraction pattern.
  • According to another aspect of the present invention there is provided a process for preparation of Form I lamotrigine comprising the steps of:
  • a) dissolving lamotrigine in an ester;
    b) maintaining at 15° C. to 30° C. for about 30 minutes to 2 hours;
    c) filtering Form I lamotrigine.
  • The ester is selected from the group consisting of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate.
  • According to another aspect of the present invention there is provided a process for preparation of Form II lamotrigine comprising the steps of:
  • a) dissolving lamotrigine in dioxane;
    b) maintaining at about 15° C. to about 30° C. for about 1 hour to 3 hours;
    c) filtering Form II lamotrigine.
  • According to another aspect of the present invention there is provided a process for preparation of Form III lamotrigine comprising the steps of:
    • a) mixing lamotrigine, isopropyl acetate, chloroform and dimethyl formamide at about 60° C. to about 70° C.;
    • b) filtering the Form III lamotrigine at about 20° C. to about 30° C.
      Lamotrigine prepared by any of the known methods can be used in the above processes. Lamotrigine solvate or hydrate may also be used in the above processes.
  • According to another aspect of the present invention there is provided a pharmaceutical composition comprising Form I or Form II or Form III lamotrigine.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a x-ray powder diffraction pattern of Form I lamotrigine.
  • FIG. 2 is a x-ray powder diffraction pattern of Form II lamotrigine.
  • FIG. 3 is a x-ray powder diffraction pattern of Form III lamotrigine.
    •
  • x-Ray powder diffraction spectrum was measured on a Siemens diffractometer.
    • DETAILED DESCRIPTION OF THE INVENTION
  • According to one aspect of the present invention, there is provided a novel crystalline Form I of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 12.5, 13.9, 16.7, 18.0, 22.3, 23.6, 26.8, 27.9, 28.5, 28.9, 29.4, 31.7, 40.2, 42.3 degrees. FIG. 1 shows typical Form I x-ray powder diffraction pattern.
  • According to another aspect of the present invention, there is provided a process for preparation of Form I lamotrigine. Thus lamotrigine is dissolved in an ester. The ester is selected from the group consisting of ethyl acetate, methyl acetate, ethyl formate, isopropyl acetate. The Form I lamotrigine is maintained at about 15° C. to about 30° C., preferably at about 20° C. to about 25° C., for about 30 minutes to about 2 hours and filtered. Lamotrigine prepared by any of the known methods can be used in the process. Lamotrigine solvate or hydrate may also be used.
  • According to another aspect of the present invention, there is provided a novel crystalline Form II lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 8.9, 11.2, 12.3, 13.2, 13.9, 17.0, 17.4, 18.0, 18.2, 18.7, 19.8, 21.4, 22.1, 22.7, 25.1, 25.4, 25.7, 26.4, 26.8, 27.1, 27.5, 28.3, 28.8, 29.2, 30.1, 30.9, 31.4, 32.9, 35.3, 35.7, 36.5 degrees. FIG. 2 shows typical Form II x-ray powder diffraction pattern.
  • According to another aspect of the present invention there is provided a process for preparation of Form II lamotrigine. Thus lamotrigine is dissolved in dioxane and maintained at about 15° C. to about 30° C. for about 1 hour to 3 hours. The separated Form II lamotrigine is filtered. Lamotrigine prepared by any of the known methods can be used in the process. Lamotrigine solvate or hydrate may also be used.
  • According to another aspect of the present invention, there is provided a novel crystalline Form III of lamotrigine characterized by an x-ray powder diffraction pattern having peaks expressed as 2θ at about 9.9, 12.0, 13.3, 16.1, 17.0, 18.1, 18.7, 19.5, 24.4, 26.0, 26.3, 27.6, 28.1, 37.1 degrees. FIG. 3 shows typical Form III x-ray powder diffraction pattern.
  • According to another aspect of the present invention there is provided a process for preparation of Form III lamotrigine. Thus lamotrigine isopropyl acetate, chloroform and dimethyl formamide are mixed and heated to about 60° C. to about 70° C. The contents are maintained for about 30 minutes and cooled to about 20° C. to about 30° C. The Form III lamotrigine is filtered. Lamotrigine prepared by any of the known methods can be used in the process. Lamotrigine solvate or hydrate may also be used.
  • According to another aspect of the present invention there is provided a pharmaceutical composition comprising Form I or Form II or Form III lamotrigine. The forms of lamotrigine may be formulated in a form suitable for oral administration or injection.
  • The following examples are given for the purpose of illustrating the present invention and should not be considered as limitations on the scope or spirit of the invention.
    • Example 1
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is mixed with ethyl acetate (100 ml) and maintained at about 70° C. for 30 minutes. Then the contents are cooled to about 20° C. The solid is separated by filtration to give 9.0 gm of Form I lamotrigine.
    • Example 2
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is added to dioxane (100 ml), maintained at 50° C. to 55° C. for 30 minutes, cooled to 25° C. and maintained at this temperature for 2 hours. The solid is separated by filtration to give 8.5 gm of Form II lamotrigine.
    • Example 3
  • Lamotrigine (10 gm) (obtained by the process described in example 1 of U.S. Pat. No. 4,602,017) is added to isopropyl acetate (150 ml) and the contents are heated to about 65° C. Chloroform (50 ml) and dimethyl formamide (48 ml) are added at this temperature and stirred for 30 minutes. The contents are cooled to 25° C. and filtered to give 9.5 gm of Form III lamotrigine.
    • Example 4
  • Example 1 is repeated using Form II lamotrigine instead of lamotrigine to give Form I lamotrigine.
    • Example 5
  • Example 1 is repeated using Form III lamotrigine instead of lamotrigine to give Form I lamotrigine.
    • Example 6
  • Example 2 is repeated using Form III lamotrigine instead of lamotrigine to give Form II lamotrigine.
    • Example 7
  • Example 2 is repeated using Form I lamotrigine instead of lamotrigine to give Form II lamotrigine.
    • Example 8
  • Example 3 is repeated using Form II lamotrigine instead of lamotrigine to give Form III lamotrigine.
    • Example 9
  • Example 3 is repeated using Form I lamotrigine instead of lamotrigine to give Form III lamotrigine.

Claims (4)

1-13. (canceled)
14. A pharmaceutical composition comprising a crystalline form of lamotrigine and a pharmaceutically acceptable carrier, wherein the crystalline form of lamotrigine is Form I lamotrigine.
15. A pharmaceutical composition comprising a crystalline form of lamotrigine and a pharmaceutically acceptable carrier, wherein the crystalline form of lamotrigine is Form II lamotrigine.
16. A pharmaceutical composition comprising a crystalline form of lamotrigine and a pharmaceutically acceptable carrier, wherein the crystalline form of lamotrigine is Form III lamotrigine.
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WO2004083191A1 (en) * 2003-03-17 2004-09-30 Hetero Drugs Limited Novel crystalline forms of lamotrigine
US7504516B2 (en) 2003-03-27 2009-03-17 Hetero Drugs Limited Crystalline forms of candesartan cilexetil
GB2395483A (en) * 2003-07-03 2004-05-26 Jubilant Organosys Ltd Crystalline lamotrigine and its monohydrate
US8486927B2 (en) * 2007-11-09 2013-07-16 Thar Pharmaceuticals Crystalline forms of lamotrigine

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4602017A (en) * 1979-06-01 1986-07-22 Sawyer David A Substituted aromatic compounds
US7132570B2 (en) * 2002-12-20 2006-11-07 Cephalon France Method for the production of crystalline forms and crystalline forms of optical enantiomers of modafinil
US7521553B2 (en) * 2003-03-17 2009-04-21 Hetero Drugs Limited Crystalline forms of lamotrigine

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CA2439468A1 (en) * 2001-02-27 2002-09-06 Teva Pharmaceutical Industries Ltd. New crystal forms of lamotrigine and processes for their preparations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4602017A (en) * 1979-06-01 1986-07-22 Sawyer David A Substituted aromatic compounds
US7132570B2 (en) * 2002-12-20 2006-11-07 Cephalon France Method for the production of crystalline forms and crystalline forms of optical enantiomers of modafinil
US7521553B2 (en) * 2003-03-17 2009-04-21 Hetero Drugs Limited Crystalline forms of lamotrigine

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US20050119265A1 (en) 2005-06-02
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AU2003217437A1 (en) 2004-10-11
WO2004083191A1 (en) 2004-09-30

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