WO2003020708A1 - Produits intermediaires de zosinamide et synthese y relative - Google Patents

Produits intermediaires de zosinamide et synthese y relative Download PDF

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Publication number
WO2003020708A1
WO2003020708A1 PCT/US2002/027593 US0227593W WO03020708A1 WO 2003020708 A1 WO2003020708 A1 WO 2003020708A1 US 0227593 W US0227593 W US 0227593W WO 03020708 A1 WO03020708 A1 WO 03020708A1
Authority
WO
WIPO (PCT)
Prior art keywords
bos
mixture
benzisoxazole
crystalline
process according
Prior art date
Application number
PCT/US2002/027593
Other languages
English (en)
Inventor
Tamar Nidam
Marioara Mendelovici
Eduard Schwartz
Shlomit Wizel
Original Assignee
Teva Pharmaceutical Industries Ltd.
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 Teva Pharmaceutical Industries Ltd., Teva Pharmaceuticals Usa, Inc. filed Critical Teva Pharmaceutical Industries Ltd.
Priority to CA002458905A priority Critical patent/CA2458905A1/fr
Priority to IL15823902A priority patent/IL158239A0/xx
Priority to JP2003524979A priority patent/JP2005506980A/ja
Priority to EP02768748A priority patent/EP1430037A4/fr
Publication of WO2003020708A1 publication Critical patent/WO2003020708A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems

Definitions

  • the second method described in literature for zomsamide preparation includes the preparation of BOA starting f om 4-hydroxy-coumarin, followed by the sulfonation reaction of BOA to BOS.
  • the sulfonation reaction of the zonisamide intermediate i.e., BOA
  • the reagent chlorosulfonic acid is used in a large excess and it is also the reaction solvent.
  • the reactions of this synthetic method are shown in scheme 2:
  • the present invention provides a novel crystal form of BOS-Na Form ⁇ , characterized by an X-Ray Powder Diffraction (XRD) having the main peaks at about 5.3, 16.6, 21.3 and 26.7 ⁇ 0.2 degrees two theta.
  • XRD X-Ray Powder Diffraction
  • the present invention provides a novel crystal form of BOS-Na Form HI, characterized by a Furier Transform Infra Red Spectroscopy (FTIR) spectrum having the most characteristic peaks at about 3604, 1065, 812 and 696 cm '1 .
  • FTIR Furier Transform Infra Red Spectroscopy
  • Fig. 15 depicts the Furier Transform Infra Red Spectroscopy (FTIR) spectrum of BOS-Ba novel Form I.
  • FTIR Furier Transform Infra Red Spectroscopy
  • the sulfonation process for the Ac 2 O/H SO involves a reaction that is performed in polar and non-polar solvents.
  • the polar solvents include ethylacetate, ethylcellosolve, methylcellosolve, dichloroethane, dichloromethane, chloroform or mixture thereof and the like.
  • the non-polar solvents include toluene, heptane, hexanes, alkanes or mixtures thereof and the like.
  • Example 4 Preparation of BOS-Na: CISO3H in dichloroethane In a 100 mL three necked flask, equipped with thermometer, condenser and mechanical stirrer was charged dichloroethane (25 mL), 2.5 mL ClSO 3 H (1.3 eq.), and BOA (5 grams). The reaction mixture was heated at reflux for 1.5 hours.
  • BOS-Na monohydrate novel form I is characterized by the following X-Ray Diffraction main peaks at about 5.0, 15.7, 16.5, 17.3, 18.6, 19.1, 19.7, 21.5, 22.8, 23.2, 23.5 and 24.3 ⁇ 0.2 degrees two theta.
  • Water content measured by Karl-Fischer (KF) method is in agreement with TGA weight loss step and is about 7%. This water content is coincident with the expected water content of monohydrate.
  • DTG DTG profile of BOS-Ba novel form I is characterized by an endothermic peak at about 200°C. A weight loss step of about 3.5% is observed in this temperature range.
  • reaction mixture was cooled to room temperature and ice was added.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne une nouvelle sulfonation d'un produit intermédiaire de zosinamide. Elle concerne en particulier le processus de sulfonation au moyen d'acide chlorosulfonique, ou d'anhydride acétique et d'acide sulfurique dans un solvant organique. L'invention concerne en outre des formes cristallines de l'acide benzisoxazole méthane sulfonique (BOS-H) et de ses sels (BOS-Na, BOS-Ca, et BOS-Ba) et de nouveaux procédés de préparation de ces composés.
PCT/US2002/027593 2001-08-30 2002-08-29 Produits intermediaires de zosinamide et synthese y relative WO2003020708A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002458905A CA2458905A1 (fr) 2001-08-30 2002-08-29 Produits intermediaires de zosinamide et synthese y relative
IL15823902A IL158239A0 (en) 2001-08-30 2002-08-29 Zonisamide intermediate and synthesis
JP2003524979A JP2005506980A (ja) 2001-08-30 2002-08-29 ゾニスアミド中間体及び合成
EP02768748A EP1430037A4 (fr) 2001-08-30 2002-08-29 Produits intermediaires de zosinamide et synthese y relative

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US31610901P 2001-08-30 2001-08-30
US60/316,109 2001-08-30
US34443901P 2001-10-24 2001-10-24
US60/344,439 2001-10-24

Publications (1)

Publication Number Publication Date
WO2003020708A1 true WO2003020708A1 (fr) 2003-03-13

Family

ID=26980239

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/027593 WO2003020708A1 (fr) 2001-08-30 2002-08-29 Produits intermediaires de zosinamide et synthese y relative

Country Status (5)

Country Link
EP (1) EP1430037A4 (fr)
JP (1) JP2005506980A (fr)
CA (1) CA2458905A1 (fr)
IL (1) IL158239A0 (fr)
WO (1) WO2003020708A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1472236A1 (fr) * 2002-02-22 2004-11-03 Teva Pharmaceutical Industries Ltd. Procede servant a la preparation de chlorure de benzisoxazole methane sulfonyle et a son amidation pour former un zonisamide
WO2005030738A1 (fr) * 2003-09-29 2005-04-07 Suven Life Sciences Limited Procede ameliore de fabrication d'intermediaires utilises pour l'obtention de zonisamide
US6900333B2 (en) 2003-01-13 2005-05-31 Dainippon Pharmaceutical Co., Ltd. Process for the preparation of 1, 2-dichlorethane free crystals of zonisamide
US7375233B2 (en) 2005-12-16 2008-05-20 Apotex Pharmachem Inc. Process for the preparation of zonisamide and the intermediates thereof
US7745471B2 (en) 2004-06-18 2010-06-29 Chemagis Ltd. Derivatives of 1,2-benzisoxazole-3-methane sulfonic acid as novel intermediates for the synthesis of zonisamide

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL376216A1 (en) * 2003-01-10 2005-12-27 Dipharma S.P.A. A process for the preparation of benzo[d]isoxazol-3-yl-methanesulfonic acid and the intermediates thereof
EP1935888A4 (fr) * 2005-09-16 2011-07-13 Dainippon Sumitomo Pharma Co Procédé de sulfonation de l' acide 1,2-benzisoxazole-3-acétique
WO2018004994A1 (fr) 2016-07-01 2018-01-04 Res Usa, Llc Réacteur à membrane à lit fluidisé
WO2018004993A1 (fr) 2016-07-01 2018-01-04 Res Usa, Llc Réduction des émissions de gaz à effet de serre
WO2018004992A1 (fr) 2016-07-01 2018-01-04 Res Usa, Llc Conversion de méthane en diméthyléther

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5377057A (en) * 1976-12-16 1978-07-08 Dainippon Pharmaceut Co Ltd 1,2-benxisoxazole derivatives
US4172896A (en) * 1978-06-05 1979-10-30 Dainippon Pharmaceutical Co., Ltd. Methane-sulfonamide derivatives, the preparation thereof and composition comprising the same
JPS54163570A (en) * 1978-06-12 1979-12-26 Dainippon Pharmaceutical Co Benzooxazole derivative
JPS54163823A (en) * 1978-06-12 1979-12-26 Dainippon Pharmaceutical Co Antiiepileptic agent based on 33sulphamoylmethyll 1*22benzisoxazole
FR2428033A1 (fr) * 1978-06-09 1980-01-04 Dainippon Pharmaceutical Co Nouveaux derives heterocycliques de methanesulfonamide utiles notamment comme anticonvulsivants et leur procede de preparation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002070495A1 (fr) * 2001-03-02 2002-09-12 Teva Pharmaceutical Industries Ltd. Procede de preparation d'acide 1,2-benzisoxazole-3-acetique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5377057A (en) * 1976-12-16 1978-07-08 Dainippon Pharmaceut Co Ltd 1,2-benxisoxazole derivatives
US4172896A (en) * 1978-06-05 1979-10-30 Dainippon Pharmaceutical Co., Ltd. Methane-sulfonamide derivatives, the preparation thereof and composition comprising the same
FR2428033A1 (fr) * 1978-06-09 1980-01-04 Dainippon Pharmaceutical Co Nouveaux derives heterocycliques de methanesulfonamide utiles notamment comme anticonvulsivants et leur procede de preparation
JPS54163570A (en) * 1978-06-12 1979-12-26 Dainippon Pharmaceutical Co Benzooxazole derivative
JPS54163823A (en) * 1978-06-12 1979-12-26 Dainippon Pharmaceutical Co Antiiepileptic agent based on 33sulphamoylmethyll 1*22benzisoxazole

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
See also references of EP1430037A4 *
UNO ET AL.: "Studies on 3-substituted 1,2-benzisoxazole derivatives. VII. Catalytic reduction of 3-sulfamoylmethyl-1,2-benzisoxazole and reactions of the resulting products", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 30, no. 1, 1981, pages 333 - 335, XP002959509 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1472236A1 (fr) * 2002-02-22 2004-11-03 Teva Pharmaceutical Industries Ltd. Procede servant a la preparation de chlorure de benzisoxazole methane sulfonyle et a son amidation pour former un zonisamide
EP1472236A4 (fr) * 2002-02-22 2006-04-19 Teva Pharma Procede servant a la preparation de chlorure de benzisoxazole methane sulfonyle et a son amidation pour former un zonisamide
US6900333B2 (en) 2003-01-13 2005-05-31 Dainippon Pharmaceutical Co., Ltd. Process for the preparation of 1, 2-dichlorethane free crystals of zonisamide
WO2005030738A1 (fr) * 2003-09-29 2005-04-07 Suven Life Sciences Limited Procede ameliore de fabrication d'intermediaires utilises pour l'obtention de zonisamide
US7745471B2 (en) 2004-06-18 2010-06-29 Chemagis Ltd. Derivatives of 1,2-benzisoxazole-3-methane sulfonic acid as novel intermediates for the synthesis of zonisamide
US7375233B2 (en) 2005-12-16 2008-05-20 Apotex Pharmachem Inc. Process for the preparation of zonisamide and the intermediates thereof

Also Published As

Publication number Publication date
JP2005506980A (ja) 2005-03-10
CA2458905A1 (fr) 2003-03-13
IL158239A0 (en) 2004-05-12
EP1430037A1 (fr) 2004-06-23
EP1430037A4 (fr) 2004-11-17

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