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Method for preparing topiramate
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A technology of topiramate and fructopyranose, which is applied in the preparation of sugar derivatives, chemical instruments and methods, esterified saccharides, etc., can solve the problem of difficult commercial application of sulfamoyl chloride, uncontrollable exothermic reaction, and lack of topiramate, etc. problem, to achieve the effect of facilitating industrial production, shortening the reaction time, and reducing the generation of by-products
Inactive Publication Date: 2011-02-23
NANJING UNIV OF SCI & TECH
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But, there are two big defects in this route: 1, require NaH to be combined with DMF, and this is an uncontrollable exothermic reaction, therefore is potential explosive; Toxic and highly corrosive chlorosulfonyl isocyanate (CSI) preparation
However, on the other hand, 2,3:4,5-bis-O-(1-methylethylene)-β-D fructopyranose chlorosulfonate is easily hydrolyzed to 2,3 : 4,5-bis-O-(1-methylethylene)-β-D fructopyranose, so that the amount of topiramate finally obtained is very small or even no topiramate is obtained
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[0031] The route of the synthetic topiramate of a kind of preparation method of topiramate of the present invention is as follows:
[0032]
[0033] A kind of preparation method of topiramate of the present invention, 2,3:4,5-bis-O-(1-methylethylidene)-D-fructopyranose chlorosulfonate is dissolved in organic solvent and solidammonium carbonate The reaction, the specific steps are as follows: at 35 ~ 95 ° C, the compound 2,3:4,5-bis-O-(1-methylethylidene)-D-fructopyranose chlorosulfonate was fully dissolved in organic After being added to the mixture of solid ammonium carbonate and an appropriate amount of dehydrating agent in the solvent, after reacting for 0.5-24 hours, concentrate to remove the solvent, add an appropriate amount of ethyl acetate and activated carbon for decolorization, then filter to remove the activated carbon and concentrate the filtrate to dryness to obtain crude topiramate. The crude topiramate is recrystallized by adding a mixed solvent of isopropan...
Embodiment 1
[0038] Embodiment 1: 2,3:4, the preparation of 5-bis-O-(1-methylethylene)-D-fructopyranose sulfamate
[0039] At 65°C, 2,3:4,5-bis-O-(1-methylethylene)-D-fructopyranose chlorosulfonate (5 g, 13.9 mmol) was dissolved in THF solution (50 mL), Solidammonium carbonate (2.67g, 27.8mmol) and anhydroussodiumsulfate (0.79g, 5.6mmol) were added, and the reaction was complete after 24 hours. The reaction was concentrated to remove THF, and 20mL of ethyl acetate and 1g of activated carbon were added for decolorization. Activated carbon was filtered off, the filtrate was concentrated to dryness, and a mixture of isopropanol and n-hexane was added for recrystallization. Cool to crystallize, filter and fully dry the filter cake to obtain 3.75 g of white crystals, with a yield of 80%. mp122~123℃, 1 H-NMR (300MHz, CDCl 3 ), δ: 5.03 (br s, 2H, NH 2 ), 3.77-4.64 (m, 7H), 1.35, 1.43 (2s, 6, 4, 5-CH 3 ), 1.49, 1.56 (2s, 6, 2, 3-CH 3 ).
Embodiment 2
[0040] Example 2: Preparation of 2,3:4,5-bis-O-(1-methylethylene)-D-fructopyranose sulfamate
[0041] At 35°C, according to the operation of Example 1, the yield was 68%.
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Abstract
The invention discloses a method for preparing toiramate. In the method, 2,3:4,5-di-O-(1-methylethylidene)-D-fructopyranose chlorosulfonic acid ester is dissolved in an organic solvent for reacting with solidammoniumcarbonate. The method comprises the following specific steps of: fully dissolving the 2,3:4,5-di-O-(1-methylethylidene)-D-fructopyranose chlorosulfonic acid ester in the organic solvent; adding the dissolved product into the mixture of the solidammoniumcarbonate and an appropriate amount of dehydrating agent; reacting and concentrating so as to remove the solvent; adding an appropriate amount of ethyl acetate and active carbon for decoloring; filtering the active carbon out and concentrating filtrate so as to obtain crude toiramate; adding a mixed solvent consisting of isopropanol and normal hexane so as to recrystallize the crude toiramate; and filtering after cooling and crystallizing and fully drying a filter cake so as to obtain pure toiramate. In the method, solidammonium carbonate instead of ammonia gas is used in an ammonolysis reaction; and the method is easy, convenient and safe to operate, lowers equipment cost and is beneficial to industrialized production.
Description
technical field [0001] The invention belongs to the field of pharmacy, in particular to a preparation method of epilepsydrugtopiramate. Background technique [0002] Topiramate is a new type of antiepileptic drug that replaces monosaccharide with sulfamate, and its pharmacological effect is to selectively block voltage-dependent sodium channels. Topiramate can also increase the frequency of gamma-aminobutyric acid (GABA) and activate GABA receptors, thereby enhancing the ability of GABA to induce chlorideion influx and enhancing the role of inhibitory neurotransmitters in the nervous system. In addition, topiramate can reduce the activity of glutamate AMPA receptors, thereby weakening the role of excitatory central neurotransmitters in the nervous system. [0003] The chemical name of topiramate is: 2,3:4,5-bis-O-(1-methylethylene)-β-D-fructopyranose sulfamate, and its structural formula is as follows: [0004] [0005] US Patent No. 4,513,006 in 1985, US Patent No. ...
Claims
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