IP Library Granted Patent US 7,132,570
Granted Patent B2
US 7,132,570 · App. 10/539,918 · Granted Nov 7, 2006

Method for the production of crystalline forms and crystalline forms of optical enantiomers of modafinil

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Quick Facts
Patent No.
US 7,132,570
App. No.
10/539,918
Granted
Nov 7, 2006
Kind
B2
Abstract

The invention relates to a process for the preparation of crystalline forms of the optical enantiomers of modafinil, comprising stages comprising: i) dissolving one of the optical enantiomers of modafinil in a solvent other than ethanol, ii) crystallising the modafinil enantiomer, iii) recovering the crystalline form of the modafinil enantiomer so obtained. The invention also relates to a process for the preparation of the optical enantiomers of modafinil.

Claims (15)

1. A laevorotatory enantiomer of modafinil in a polymorphic form that produces a powder X-ray diffraction spectrum comprising intensity peaks at the interplanar spacings: 8.54, 4.27, 4.02, 3.98 (Å).

2. The laevorotatory enantiomer of modafinil according to claim 1 , wherein the polymorphic form produces a powder X-ray diffraction spectrum further comprising intensity peaks at the interplanar spacings: 13.40, 6.34, 5.01, 4.68, 4.62, 4.44, 4.20, 4.15, 3.90, 3.80, 3.43 (Å).

3. A laevorotatory enantiomer of modafinil in a polymorphic form that produces a powder X-ray diffraction spectrum comprising reflections at 15.4, 31.1, 33.1 and 33.4 degrees 2θ.

4. The laevorotatory enantiomer of modafinil according to claim 3 , wherein the polymorphic form produces a powder X-ray diffraction spectrum further comprising reflections at 9.8, 20.8, 26.4, 28.3, 28.7, 29.9, 31.6, 32, 34.1, 35.1 and 39 degrees 2θ.

5. A pharmaceutical composition comprising a laevorotatory enantiomer of modafinil according to any one of claims 1 to 4 .

6. A pharmaceutical composition consisting essentially of a laevorotatory enantiomer of modafinil according to according to any one of claims 1 to 4 .

7. A Form I polymorph of (−)-modafinil.

8. A pharmaceutical composition comprising a Form I polymorph of (−)-modafinil according to claim 7 .

9. A pharmaceutical composition consisting essentially of a Form I polymorph of (−)-modafinil according to claim 7 .

10. A process for preparing a Form I polymorph of (−)-modafinil comprising the steps of:

(a) providing a solution of (−)-modafinil dissolved in a hot solvent;

(b) rapidly cooling the solution from step (a) to produce crystals;

(c) filtering the crystals;

(d) drying the crystals; and

(e) obtaining the crystals of said Form I polymorph of (−)-modafinil, wherein the solvent of step (a) is selected from water, methanol, absolute ethanol, absolute ethanol plus 3% water (v/v), and ethanol denatured with toluene plus 3% water, (v/v, based on the total volume of ethanol and toluene).

Assignments (4)
MERGER Recorded Jan 24, 2013
From: CEPHALON FRANCE
To: TEVA SANTE
Reel/Frame 029692/0457 →
MERGER Recorded Mar 22, 2007
From: ORGANISATION DE SYNTHESE MONDIALE ORSYMONDE
To: CEPHALON FRANCE
Reel/Frame 019063/0560 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2006
From: LEPROUST, PIERRE
To: CEPHALON FRANCE
Reel/Frame 017988/0596 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2006
From: NECKEBROCK, OLIVIER; COURVOISIER, LAURENT; GRAF, STEPHANIE; SERRURE, GILLES; COQUEREL, GERARD; ROSE, SEBASTIEN; BESSELIEVRE, CHRISTINE; MALLET, FRANCK; VAN LANGEVELDE, ADRIAAN JAN
To: CEPHALON FRANCE; ORGANISATION DE SYNTHESE MONDIALE ORSYMONDE
Reel/Frame 017132/0061 →