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Modafinil compositions

a technology of compositions and modafinil, which is applied in the direction of drug compositions, biocide, organic chemistry, etc., can solve the problems of filtration problems, non-uniform mixtures, and needle-like morphologies

Inactive Publication Date: 2009-01-15
CEPHALON INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017]In a still further aspect of the invention, a method is provided for treating a subject, preferably a human subject, suffering from excessive daytime sleepiness associated with narcolepsy, multiple sclerosis related fatigue, infertility, eating disorders, attention deficit hyperactivity disorder (ADHD), Parkinson's disease, incontinence, sleep apnea, or myopathies where modafinil is an effective active pharmaceutical for said disorder. The method comprises adm

Problems solved by technology

For example, needle-like crystal forms or habits of APIs can cause aggregation, even in compositions where the API is mixed with other substances, such that a non-uniform mixture is obtained.
Needle-like morphologies can also give rise to filtration problems (See e.g., Mirmehrabi et al.

Method used

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  • Modafinil compositions
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Examples

Experimental program
Comparison scheme
Effect test

example 1

2:1 R-(−)-modafinil:S-(+)-modafinil

[0146]Anhydrous ammonia gas was bubbled through a solution containing R-benzhydrylsulfinyl methyl ester (8.62 g, 0.0299 mol, about 80:20 R-isomer:S-isomer by weight) in methanol (125 mL) for 10 minutes. The pressure build-up from the reaction caused a back flow of sodium bicarbonate from the trap into the reaction mixture. The reaction was stopped and the precipitate was collected. The filtrate was concentrated under reduced pressure to give a yellow solid residue (2.8 g). The yellow solid was passed through a column (silica gel, grade 9385, 230-400, mesh 60 angstroms), 3:1 v / v ethyl acetate:hexane as eluent). The filtrates were then combined and concentrated under reduced pressure to give a slightly yellow solid (most of the yellow color remained on the column). The solid was then re-crystallized from ethanol by heating the mixture until it was boiling and then cooling to room temperature to give 2:1 R-(−)-modafinil:S-(+)-modafinil as a colorless ...

example 2

Polymorphs of R-(−)-modafinil

[0149]Several polymorphs of R-(−)-modafinil have been observed, each characterized by PXRD. FIGS. 3, 6, and 9 show these PXRD diffractograms (data as collected) of polymorphs Form III, Form IV, and Form V.

[0150]Recrystallization has proved to be an effective technique for the formation and acquisition of the polymorphs of R-(−)-modafinil. Suitable solvents for the crystallization of one or more polymorphs of R-(−)-modafinil include, but are not limited to, acetonitrile, dimethyl formamide (DMF), methanol, methyl ethyl ketone, N-methyl pyrollidone, ethanol, isopropanol, isobutanol, formamide, isobutyl acetate, 1,4-dioxane, tetrahydrofuran (THF), ethyl acetate, o-xylene, isopropyl acetate, dichloromethane, propylene glycol, acetic acid, water, acetone, nitromethane, toluene, and benzyl alcohol. Pure solvents and mixtures of solvents may be used to crystallize one or more polymorphs of R-(−)-modafinil.

R-(−)-modafinil Form III

[0151]Anhydrous ammonia gas was ...

example 3

2:1 R-(−)-modafinil:S-(+)-modafinil

[0172]A solution containing R-(−)-modafinil (80.16 mg, 0.293 mmol) and racemic modafinil (20.04 mg, 0.0366 mmol) in ethanol (2 mL) was prepared. The mixture was heated to boiling in order to dissolve the entire solid and was then cooled to room temperature (25 degrees C.). After remaining at room temperature for 15 minutes, the solution was placed at 5 degrees C. overnight. The solution was then decanted and the remaining crystals were dried under a flow of nitrogen gas and characterized using HPLC, PXRD, DSC, and thermal microscopy.

[0173]The crystals obtained contained between about 63 and about 67 percent R-(−)-modafinil and the remainder of the crystals was S-(+)-modafinil. HPLC analysis indicated that the crystals were a 2:1 phase containing two R-(−)-modafinil molecules for every one S-(+)-modafinil molecule.

[0174]PXRD was completed on a single crystal sample of the 2:1 R-(−)-modafinil:S-(+)-modafinil. 2:1 R-(−)-modafinil:S-(+)-modafinil can b...

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Abstract

Polymorphs and solvates of racemic, enantiomerically pure, and enantiomerically mixed modafinil are formed and discussed. In addition, said forms are described as useful for the treatment of many conditions including, but not limited to, narcolepsy.

Description

FIELD OF THE INVENTION[0001]The present invention relates to modafinil-containing compositions, pharmaceutical compositions comprising modafinil, and methods for preparing the same.BACKGROUND OF THE INVENTION[0002]Active pharmaceutical ingredients (API or APIs (plural)) in pharmaceutical compositions can be prepared in a variety of different forms. Such APIs can be prepared so as to have a variety of different chemical forms including chemical derivatives, solvates, hydrates, co-crystals, or salts. Such APIs can also be prepared to have different physical forms. For example, the APIs may be amorphous, may have different crystalline polymorphs, or may exist in different solvation or hydration states. By varying the form of an API, it is possible to vary the physical properties thereof. For example, crystalline polymorphs typically have different solubilities from one another, such that a more thermodynamically stable polymorph is less soluble than a less thermodynamically stable poly...

Claims

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Application Information

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IPC IPC(8): A61K31/165C07C231/00A61P25/00
CPCA61K31/165C07C317/50C07C317/44A61P25/00A61P25/16A61P25/28
Inventor HICKEY, MAGALI BOURGHOLPETERSON, MATTHEWALMARSSON, ORNOLIVEIRA, MARK
Owner CEPHALON INC
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