Modafinil compositions
A technology of a composition and a drug, applied in the field of compositions containing modafinil, can solve problems such as poor solubility
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Embodiment 1
[0155] 2:1 R-(-)-modafinil:S-(+)-modafinil
[0156] Bubble anhydrous ammonia through methanol containing R-benzhydrylsulfinylmethyl ester (8.62 g, 0.0299 mol, about 80:20 R-isomer:S-isomer by weight) (125 mL) solution for 10 minutes. Pressure build-up from the reaction caused sodium bicarbonate to flow back from the retort into the reaction mixture. The reaction was stopped and the precipitate was collected. The filtrate was concentrated under reduced pressure to obtain a yellow solid residue (2.8 g). The yellow solid was columned (silica gel, grade 9385, 230-400 mesh, 60 Angstroms) with 3:1 v / v ethyl acetate:hexane as eluent. The filtrates were then combined and concentrated under reduced pressure to give a slightly yellowish solid (most of the yellow color remained on the column). The solid was then recrystallized from ethanol by heating the mixture until it boiled and then cooled to room temperature to give 2:1 R-(-)-modafinil:S-(+)-modafinil as a colorless solid (580m...
Embodiment 2
[0160] Polymorphs of R-(-)-modafinil
[0161] Several polymorphs of R-(-)-modafinil were observed, each characterized by PXRD. image 3 , 6 , and 9 represent these PXRD diffractograms (data obtained for direct collection) of the Form III, Form IV, and Form V polymorphs.
[0162] Recrystallization has proven to be an efficient technique for forming and obtaining polymorphs of R-(-)-modafinil. Suitable solvents for crystallization of one or more polymorphs of R-(-)-modafinil include, but are not limited to, acetonitrile, dimethylformamide (DMF), methanol, methyl ethyl ketone , N-methylpyrrolidone, ethanol, isopropanol, isobutanol, formamide, isobutyl acetate, 1,4-dioxane, tetrahydrofuran (THF), ethyl acetate, o-xylene, acetic acid Isopropyl ester, methylene chloride, propylene glycol, acetic acid, water, acetone, nitromethane, toluene, and benzyl alcohol. Pure solvents and mixtures of solvents can be used for the crystallization of one or more polymorphs of R-(-)-modafinil. ...
Embodiment 3
[0188] 2:1 R-(-)-modafinil:S-(+)-modafinil
[0189] 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 to dissolve all solids, then cooled to room temperature (25°C). After 15 minutes at room temperature, the solution was allowed to stand overnight at 5°C. The solution was then decanted off and the remaining crystals were dried under nitrogen flow and characterized using HPLC, PXRD, DSC, and thermal microscopy.
[0190] The resulting crystals contained about 63 to about 67% R-(-)-modafinil, with the remainder of the crystals being S-(+)-modafinil. HPLC analysis showed that the crystals were a 2:1 phase containing two R-(-)-modafinil molecules per S-(+)-modafinil molecule.
[0191] PXRD was performed on single crystal samples of 2:1 R-(-)-modafinil:S-(+)-modafinil. 2:1 R-(-)-modafinil:S-(+)-modafinil can pass Figure 11 Any one, any two, any three, any ...
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