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WO2005003104A3 - Crystalline forms of lamotrigine monohydrate and anhydrous lamotrigine and a process for their preparation - Google Patents

Crystalline forms of lamotrigine monohydrate and anhydrous lamotrigine and a process for their preparation Download PDF

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Publication number
WO2005003104A3
WO2005003104A3 PCT/IN2004/000186 IN2004000186W WO2005003104A3 WO 2005003104 A3 WO2005003104 A3 WO 2005003104A3 IN 2004000186 W IN2004000186 W IN 2004000186W WO 2005003104 A3 WO2005003104 A3 WO 2005003104A3
Authority
WO
WIPO (PCT)
Prior art keywords
lamotrigine
monohydrate
anhydrous
dichlorophenyl
preparation
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/IN2004/000186
Other languages
French (fr)
Other versions
WO2005003104A2 (en
Inventor
Charugundla Kishore
Bokka Ravisankar
Sulur G Manjunatha
Ashok Krishna Kulkarni
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.)
Jubilant Organosys Ltd
Original Assignee
Jubilant Organosys 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 Jubilant Organosys Ltd filed Critical Jubilant Organosys Ltd
Publication of WO2005003104A2 publication Critical patent/WO2005003104A2/en
Publication of WO2005003104A3 publication Critical patent/WO2005003104A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to lamotrigine (3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine) monohydrate (Ia) and anhydrous lamotrigine, and a process for preparing the same. An improved process is provided for manufacturing the lamotrigine (I). The process comprises of reacting 2,3-dichlorobenzoyl cyanide (II) with aminoguanidine bicarbonate in aqueous mineral acid, optionally together with a water miscible organic solvent, at 30 - 80 °C to produce the 2-(2,3-dichlorophenyl)-2-(guanidinylamino)acetonitrile (Schiff base). The Schiff base is further cyclised in aqueous alcohol to produce pure lamotrigine of a pharmaceutically acceptable quality which on further drying at 45 - 50 °C under vacuum yields lamotrigine monohydrate, and/or on further drying at 100 - 110 °C yields anhydrous lamotrigine. The lamotrigine monohydrate or anhydrous lamotrigine thereby produced may then be brought into association with a pharmaceutically acceptable carrier for administration to a patient in need thereof.
PCT/IN2004/000186 2003-07-03 2004-06-28 Crystalline forms of lamotrigine monohydrate and anhydrous lamotrigine and a process for their preparation Ceased WO2005003104A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0315608.0 2003-07-03
GB0315608A GB2395483A (en) 2003-07-03 2003-07-03 Crystalline lamotrigine and its monohydrate

Publications (2)

Publication Number Publication Date
WO2005003104A2 WO2005003104A2 (en) 2005-01-13
WO2005003104A3 true WO2005003104A3 (en) 2005-09-22

Family

ID=27741536

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2004/000186 Ceased WO2005003104A2 (en) 2003-07-03 2004-06-28 Crystalline forms of lamotrigine monohydrate and anhydrous lamotrigine and a process for their preparation

Country Status (2)

Country Link
GB (1) GB2395483A (en)
WO (1) WO2005003104A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005027149A1 (en) * 2005-06-11 2006-12-14 Lanxess Deutschland Gmbh Process for the preparation of substituted benzoyl cyanides
US20120142919A1 (en) * 2006-08-02 2012-06-07 Medichem, S.A. Method for synthesizing lamotrigine
CN103570637A (en) * 2013-09-13 2014-02-12 盐城凯利药业有限公司 Preparation method of lamotrigine
CN106083753B (en) * 2016-06-07 2019-04-02 浙江奇彩环境科技股份有限公司 A kind of improved Lamotrigine synthesis technology
CN114948868B (en) 2021-04-16 2023-04-14 上海奥科达医药科技股份有限公司 Crystal form of lamotrigine hydrate, preparation method thereof and composition containing crystal form
CN116942606A (en) * 2022-04-18 2023-10-27 上海奥科达医药科技股份有限公司 Preparation method of lamotrigine suspension and dry suspension
CN115068422B (en) * 2022-08-19 2022-11-29 上海奥科达生物医药科技有限公司 Lamotrigine wet suspension and preparation method and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0247892A1 (en) * 1986-05-30 1987-12-02 The Wellcome Foundation Limited Triazine salt
EP0963980A2 (en) * 1998-06-10 1999-12-15 The Wellcome Foundation Limited 1,2,4-Triazine derivative, its preparation and its use as reference marker for testing purity and stability of "lamotrigine"
WO2000035888A1 (en) * 1998-12-14 2000-06-22 Sharad Kumar Vyas An improved process for the preparation of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
EP1127873A2 (en) * 2000-02-25 2001-08-29 Chemagis Ltd. Process for preparing substituted Benzoyl Cyanide Amidinohydrazones
WO2002068398A1 (en) * 2001-02-27 2002-09-06 Teva Pharmaceutical Industries Ltd. New crystal forms of lamotrigine and processes for their preparations
WO2003078407A1 (en) * 2001-12-24 2003-09-25 Apotex Pharmachem Inc. A new and efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines
WO2004083191A1 (en) * 2003-03-17 2004-09-30 Hetero Drugs Limited Novel crystalline forms of lamotrigine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU530999B2 (en) * 1979-06-01 1983-08-04 Wellcome Foundation Limited, The Substituted amino triazines and their use in treatment of cns disorders

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0247892A1 (en) * 1986-05-30 1987-12-02 The Wellcome Foundation Limited Triazine salt
EP0963980A2 (en) * 1998-06-10 1999-12-15 The Wellcome Foundation Limited 1,2,4-Triazine derivative, its preparation and its use as reference marker for testing purity and stability of "lamotrigine"
WO2000035888A1 (en) * 1998-12-14 2000-06-22 Sharad Kumar Vyas An improved process for the preparation of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine
EP1127873A2 (en) * 2000-02-25 2001-08-29 Chemagis Ltd. Process for preparing substituted Benzoyl Cyanide Amidinohydrazones
WO2002068398A1 (en) * 2001-02-27 2002-09-06 Teva Pharmaceutical Industries Ltd. New crystal forms of lamotrigine and processes for their preparations
WO2003078407A1 (en) * 2001-12-24 2003-09-25 Apotex Pharmachem Inc. A new and efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines
WO2004083191A1 (en) * 2003-03-17 2004-09-30 Hetero Drugs Limited Novel crystalline forms of lamotrigine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KUBICKI, M. ET AL: "Hydrogen bonding patterns in 3,5-diamino-6-aryl triazines", JOURNAL OF MOLECULAR STRUCTURE , 570(1-3), 53-60 CODEN: JMOSB4; ISSN: 0022-2860, 2001, XP002308632 *

Also Published As

Publication number Publication date
GB0315608D0 (en) 2003-08-13
WO2005003104A2 (en) 2005-01-13
GB2395483A (en) 2004-05-26

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