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Preparation method of stiripentol

A technology of stiripentol and dioxole, which is applied in the field of preparation of epilepsy drugs, can solve the problems of difficulty in determining the frequency of epileptic seizures, increase blood concentration, etc., and achieves the effects of easy separation and prevention of disproportionation reaction

Inactive Publication Date: 2014-04-23
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Dr. Edwin Trevathan of Washington University School of Medicine in Missouri, USA believes that it is difficult to determine whether stiripentol reduces the frequency of epilepsy in patients with this combination drug experiment, because the mechanism of action of stiripentol is to increase the concentration of other drugs such as clobazam. and sodium valproate blood concentrations

Method used

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  • Preparation method of stiripentol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 5-(2-methallyl)benzo[d][1,3]dioxole

[0032]

[0033] 30mL of water, 26.1g of dibromomethane, stirred and heated to reflux. Slowly add 16.4g of 4-(2-methylallyl)-1,2-benzenediol, 10.0g of sodium hydroxide and 50mL of water mixture, after the addition is complete, continue the reflux reaction for 2h; cool, add 100mL of ethyl acetate, Layered, washed with a small amount of aqueous sodium hydroxide solution, washed with water (2×100mL); the organic phase was dried with anhydrous sodium sulfate, spin-dried to dry the solvent, and distilled to obtain 12.9g of colorless liquid 5-(2-methallyl)benzo [d][1,3]dioxole, yield 73%, 1 HNMR (CDCl 3 , 300MHz), δ: 1.67(t, J=1.2Hz, 3H, CH 3 ), 3.23 (s, 2H, CH 2 ), 4.73(q, J=1.2Hz, 1H, C=CH), 4.79~4.80(q, J=1.2Hz, 1H, C=CH), 5.93(s, 2H, CH 2 O), 6.63 ~ 6.75 (m, 3H, C 6 h 3 ).GC-MS (m / z): 176 (M + ), 151, 131, 103, 77.

Embodiment 2

[0035] Preparation of 5-(2-methylpropenyl)benzo[d][1,3]dioxole

[0036]

[0037] 21.1g 5-(2-methallyl)benzo[d][1,3]dioxole, 4.2g KOH and 25mL n-butanol, react at 80°C for 6h; In ice water, add dilute hydrochloric acid dropwise until neutral, add 50mL of ethyl acetate to extract, wash with water, dry, and recover the solvent to obtain 18.4g of light yellow liquid 5-(2-methylpropenyl)benzo[d][1,3 ] Dioxole, yield 87%.

Embodiment 3

[0039] Preparation of piperonal

[0040]

[0041] 4.2g (0.024mol) 5-(2-methylpropenyl)benzo[d][1,3]dioxole and 60mL acetic acid, cooled to 0°C in an ice-salt bath, and passed through O 3 , oxidized for 1.0h, TLC monitors that the raw material point disappears; 2 1.0h, slowly add 10.0g Zn powder, continue stirring at 0°C for 2.0h, filter, extract with 20mL ethyl acetate, wash with water, and dry over anhydrous sodium sulfate. Column chromatography gave 3.1 g of a colorless liquid, which was placed in a refrigerator to give a colorless crystal of piperonal with a yield of 74% and a melting point of 36.8-37.7°C.

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Abstract

The invention relates to a method for preparing stiripentol disclosed as a chemical structural formula II from 4-(2-methylallyl)-1,2-phenyldiphenol disclosed as a chemical structural formula I, which comprises the following steps: etherifying 4-(2-methylallyl)-1,2-phenyldiphenol, isomerizing, and carrying out oxidation reaction, condensation reaction and reduction reaction to obtain the stiripentol. The stiripentol is a new drug for treating epilepsy.

Description

technical field [0001] The invention relates to a preparation method of epilepsy drugs, in particular to a method for preparing stiripentol from 4-(2-methallyl)-1,2-benzenediol. Background technique [0002] Stiripentol is a new drug for the treatment of epilepsy that was launched in 2007 [Neurotherapeutics, 2007, (4): 123-125; WO2011 / 011420A2], the chemical name is 4,4-dimethyl-1-(3 ,4-Methylenedioxyphenyl)-1-penten-3-ol [4,4-Dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol]; French researchers reported , Adding stiripentol on the basis of sodium valproate and clobazam can effectively treat severe infantile myoclonic epilepsy (Lancet, 2000, 356:1623-1624, 1638-1642); Amyl alcohol is an inhibitor of cytochrome P450. When combined with clobazam and sodium valproate, stiripentol is effective in the treatment of severe myoclonic epilepsy (SMEI). Dr. Edwin Trevathan of Washington University School of Medicine in Missouri, USA believes that it is difficult to determine whet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/54
Inventor 胡艾希伍智林叶姣
Owner HUNAN UNIV
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