Title:
モダフィニルの光学異性体の調製方法及び結晶形
Document Type and Number:
Japanese Patent JP2006511588
Kind Code:
A
Abstract:
Production of crystalline forms (specifically polymorphic forms or solvates) of enantiomers of modafinil (A) involves dissolving an enantiomer of (A) (preferably the levorotatory isomer, (-)-(A)) in a solvent other than ethanol, crystallizing the enantiomer and recovering the obtained crystalline form. Some polymorphic forms and solvates of (-)-(A) are new. Independent claims are included for: (a) the following new polymorphic forms of (-)-(A): (i) Form II, having an X-ray diffraction pattern with maxima corresponding to interplanar spacings of 8.54Å, 7.57Å, 7.44Å, 4.56Å, 3.78Å and 3.71Å; (ii) Form III, having an X-ray diffraction pattern with maxima corresponding to interplanar spacings of 12.58Å, 8.54Å, 5.01Å, 4.10Å, 3.97Å and 3.20Å; and (iii) Form IV, having an X-ray diffraction pattern with maxima corresponding to interplanar spacings of 12.38Å, 8.58Å, 7.34Å, 5.00Å and 4.09Å; (b) a new dimethyl carbonate solvate of (-)-(A), having an X-ray diffraction pattern with maxima corresponding to interplanar spacings of 12.31Å, 9.69Å, 9.09Å, 8.54Å, 7.27Å, 6.21Å, 5.45Å, 5.10Å, 5.00Å, 4.83Å, 4.63Å, 4.46Å, 4.22Å, 4.21Å, 4.09Å, 3.78Å, 3.62Å, 3.53Å, 3.42Å, 3.32Å, 3.24Å, 3.21Å and 3.10Å; (c) a method for converting a first crystalline form of an enantiomer of (A) (specifically Form I of (-)-(A)) into another crystalline form, involving suspending the first crystalline form in a suitable solvent and recovering the second form (the solvate specifically being acetonitrile, with the product being recovered as acetonitrile solvate); (d) a new acetonitrile solvate of (-)-(A), having an X-ray diffraction pattern with maxima corresponding to interplanar spacings of 16.17Å, 14.14Å, 12.32Å, 10.66Å, 9.79Å, 9.29Å, 8.54Å, 8.15Å, 7.80Å, 7.09Å, 6.31Å, 5.83Å, 5.62Å, 5.41Å, 5.10Å, 4.90Å, 4.66Å, 4.58Å, 4.46Å, 4.33Å, 4.20Å, 4.02Å, 3.92Å, 3.835Å, 3.72Å, 3.60Å, 3.57Å, 3.45Å, 3.33Å, 3.24Å, 3.19Å, 3.0Å and 3.03Å; (e) the preparation of optically active (A) from modafinic acid (B) by: (i) optically resolving (+-)-(B) and recovering at least one of the enantiomers; (ii) contacting one of the enantiomers with a lower alkyl haloformate in presence of alcohol and organic base; and (iii) converting the obtained ester into the amide; and (f) the preparation of an enantiomer of (A) by optically resolving (+-)-(B) (or its salt) by preferential crystallization and converting the obtained enantiomer into (A) (optionally via a lower alkyl ester). ACTIVITY : Nootropic; Antiparkinsonian; Cerebroprotective; Nootropic; Tranquilizer; Neuroprotective; Antidepressant; Neuroleptic; MECHANISM OF ACTION : None given in the source material.
Inventors:
Necke block, Olivier
Cour Boissiere, Laurent
Graph, stephanie
Jill
Cocle, Gerard
Rose, Sebastian
Besse Liable, Christine
Mallet, frank
Van Ranheveld, Adrian Yang
Cour Boissiere, Laurent
Graph, stephanie
Jill
Cocle, Gerard
Rose, Sebastian
Besse Liable, Christine
Mallet, frank
Van Ranheveld, Adrian Yang
Application Number:
JP2004564285A
Publication Date:
April 06, 2006
Filing Date:
December 18, 2003
Export Citation:
Assignee:
CEPHALON FRANCE
Organizion de Sainte's Mondial Orsimon
Organizion de Sainte's Mondial Orsimon
International Classes:
C07C315/06; A61K31/165; A61P3/00; A61P3/04; A61P9/10; A61P11/16; A61P25/00; A61P25/14; A61P25/16; A61P25/20; A61P25/24; A61P25/26; A61P25/28; B01D9/02; C07C315/04; C07C317/50; C07B57/00; C07C317/44
Domestic Patent References:
| JPS62190160A | 1987-08-20 |
Foreign References:
| WO2002010125A1 | 2002-02-07 |
Attorney, Agent or Firm:
Atsushi Aoki
Takashi Ishida
Tetsuji Koga
Hiroyuki Onoda
Masaya Nishiyama
Takashi Ishida
Tetsuji Koga
Hiroyuki Onoda
Masaya Nishiyama
Previous Patent: アデニンヌクレオチドトランスロカーゼ（ＡＮＴ）リガンドならびにそれ...
Next Patent: 酢酸を効率良く製造するための及び水バランスを制御するための低含水メ...
Next Patent: 酢酸を効率良く製造するための及び水バランスを制御するための低含水メ...