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Aminoacetamide compound containing benzo-aliphatic ring structure and usage thereof

A technology of aminoacetamide and compounds, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve serious and ineffective control of epileptic seizures, side effects and other problems, and achieve good anticonvulsant effect

Inactive Publication Date: 2018-12-14
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently commonly used drugs for the treatment of epilepsy include phenytoin, carbamazepine, sodium valproate and phenobarbital, etc., but all of them have serious side effects and cannot effectively control epileptic seizures. Therefore, research on new drugs with low side effects Antiepileptic drugs are imperative

Method used

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  • Aminoacetamide compound containing benzo-aliphatic ring structure and usage thereof
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  • Aminoacetamide compound containing benzo-aliphatic ring structure and usage thereof

Examples

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preparation example Construction

[0061] The method for the compound shown in the preparation formula I provided by the invention specifically comprises the following steps:

[0062] Starting from dihydrocoumarin

[0063] (1) Stir the mixture of aluminum chloride, sodium chloride and dihydrocoumarin at 200°C to 210°C for 1 hour to 2 hours, add it to ice water, then add concentrated hydrochloric acid to make the reaction system acidic, After filtering, the filter cake was washed with ethanol and dried to obtain intermediate II (4-hydroxyl-1-indanone);

[0064] (2) Dissolve intermediate II, sodium cyanoborohydride, and zinc iodide in 1,2-dichloroethane, heat to reflux for 4 to 6 hours, filter while hot, collect the filtrate and concentrate, and the residue is passed through Separation by column chromatography to obtain intermediate III (4-indenol);

[0065] (3) Dissolve the intermediate III in dichloromethane, then add tin tetrachloride while stirring under the protection of nitrogen at 0°C, after the system...

Embodiment 1

[0095] (1) Preparation of 4-hydroxyl-1-indanone (intermediate II):

[0096] Stir the mixture of 20 grams of aluminum chloride, 4 grams of sodium chloride and 4 grams of dihydrocoumarin at 200 ° C ~ 210 ° C for 1.5 hours, cool to room temperature, pour the system into an appropriate amount of ice water, add 30 ml concentrated Hydrochloric acid made the system strongly acidic, then suction-filtered with a triangular funnel, retained the filter cake, washed the filter cake with 20 ml of ethanol, and finally dried the filter cake to obtain the title compound (intermediate II), 3.24 g of a brown solid, and rate of 81%.

[0097] 1 H-NMR (400MHz, DMSO-d 6 )δ9.94(s,1H),7.24(t,J=7.6Hz,1H),7.09(d,J=7.4Hz,1H),7.04(d,J=7.8Hz,1H),2.91(t, J=5.8Hz, 2H), 2.60(t, J=5.8Hz, 2H).

[0098] (2) Preparation of 4-indanol (intermediate III):

[0099] Dissolve 2 grams of intermediate II, 2.6 grams of sodium cyanoborohydride, and 13 grams of zinc iodide in 50 milliliters of 1,2-dichloroethane, heat...

Embodiment 2

[0105] (1) 7-(3-fluorobenzyloxy)-2,3-dihydro-1-H-indene-4-carbaldehyde (compound shown in formula V-1, abbreviated as "intermediate V-1", hereinafter the same) preparation:

[0106]

[0107] Add 120 mg of intermediate IV, 107 μl of 3-fluorobenzyl chloride, and 255 mg of potassium carbonate into 3 ml of N,N-dimethylformamide, react at 90°C for 4 hours, cool the system to room temperature, and add Add water and ethyl acetate, extract the aqueous layer twice with ethyl acetate, collect the organic layer, wash the organic layer twice with water, wash once with saturated sodium chloride, add anhydrous magnesium sulfate to dry, filter, concentrate, and the residue is After separation by column chromatography, the title compound (Intermediate V-1) was obtained as a yellow solid (120 mg) with a yield of 65%.

[0108] 1H-NMR (400MHz, CDCl 3 )δ10.02(s,1H),7.63(d,J=7.7Hz,1H),7.42-7.31(m,1H),7.17(dd,J=17.2,8.4Hz,2H),7.03(t,J =8.2Hz, 1H), 6.81(d, J=7.6Hz, 1H), 5.18(s, 2H), 3.32(t, J...

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Abstract

The invention relates to an aminoacetamide compound containing a benzo-aliphatic ring structure and usage thereof. The aminoacetamide compound is a compound shown in the formula I, or an optical isomer or pharmaceutically acceptable salt of the compound, in the formula I, R1 is hydrogen, C1 to C6 linear or branched alkyl or phenyl; R2 is a C1 to C7 linear or branched alkyl, a 5 to 6-membered aromatic ring group, a heteroaryl ring group or cycloalkyl, or a substituted 5 to 6-membered aromatic ring group, an aromatic heterocyclic group or cycloalkyl; A is alkylidene or carbonyl; n is an integerof 1 to 3, wherein the substituted 5 to 6-membered aromatic ring group, heteroaryl ring group or cycloalkyl substituent group is selected from one or more of the following groups: halogen, C1 to C3 alkyl or alkoxy, C1 to C3 fluorine-containing alkyl or fluorine-containing alkoxy, a nitro group or a cyano group; hetero atoms of the aromatic heterocyclic group are nitrogen or sulfur; m is an integerof 1 to 3. The aminoacetamide compound provided by the invention can be used as an anti-epileptic medicine or an ion channel blocker.

Description

technical field [0001] The present invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to aminoacetamide compounds containing benzoaliphatic ring structure and their preparation method and application. Background technique [0002] Epilepsy is a disease of paroxysmal motor, sensory, conscious, mental, and autonomic dysfunction caused by paroxysmal abnormal discharges of brain neuron groups caused by various reasons. Its clinical symptoms include myoclonus, sudden onset Interruption of sexual mental activity, loss of consciousness, paresthesia, and emotional and psychomotor disturbances, in severe cases, sudden loss of consciousness, first tonic and then clonic convulsions, accompanied by screaming, blue complexion, white foaming at the mouth, dilated pupils, etc. , often life-threatening if the episodes are persistent. It is one of the most common diseases in neurology. The death risk of patients with this disease is 2 to 3 times t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/06C07C255/54C07D213/30C07D333/16C07D213/61C07D307/42A61P25/08
CPCA61P25/08C07C237/06C07C255/54C07C2601/14C07C2602/08C07C2602/10C07C2602/12C07D213/30C07D213/61C07D307/42C07D333/16
Inventor 李剑高召兵邱晓霞詹丽许海燕毛斐李晓康朱进
Owner EAST CHINA UNIV OF SCI & TECH
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