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Preparation of coumarin derivative and application of coumarin derivative to control of serious cerebral disease

A technology for diseases and drugs, applied in the field of medicine, can solve problems such as side effects and insufficient curative effect

Inactive Publication Date: 2013-12-18
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a wide variety of drugs are used clinically, their application is limited due to the existence or insufficient curative effect, or serious side effects

Method used

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  • Preparation of coumarin derivative and application of coumarin derivative to control of serious cerebral disease
  • Preparation of coumarin derivative and application of coumarin derivative to control of serious cerebral disease
  • Preparation of coumarin derivative and application of coumarin derivative to control of serious cerebral disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] 3-(4-Acetylpiperazin-1-yl)-5,7-dihydroxy-4-methyl-2H-chromen-2-one (5A, R=methyl)

[0107]

[0108] According to Reaction Formula 1, dissolve anhydrous piperazine 1 (0.10mol) and 0.10mol baked potassium carbonate in anhydrous acetonitrile, and slowly add 0.10mol 2 of anhydrous acetonitrile solution dropwise under vigorous stirring at room temperature, the reaction solution changes from milky white to Gradually changed to pale yellow, followed by LC-MS monitoring, after the reaction was completed, potassium carbonate was filtered off, acetonitrile was spun off, the resulting residue was added with water, stirred for 30 min, extracted three times with EA, combined extracts were dried over anhydrous Na2SO4 for 5 hours. Filter to remove Na2SO4, and distill the filtrate to remove the solvent under reduced pressure to obtain brown-red oil 3, which is directly used in the next reaction without purification.

[0109] Mix and dissolve phloroglucinol (0.10mol) and 3 (0.10mol) ...

Embodiment 2

[0113] 5,7-Dihydroxy-4-methyl-3-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-2H-benzopyran-2-one (5B, R=trifluoromethyl)

[0114]

[0115] According to Reaction Formula 1, 4 (27.6mg, 0.1mmol) was dissolved in anhydrous THF, and trifluoroacetic anhydride (0.10mmol) was added for reaction to give 5B as a pale yellow solid with a yield of 88.0%, m.p.274-275°C.

[0116] 1 H NMR (300MHz, DMSO-d 6 ):δ10.457(s,1H),10.220(s,1H),6.258(d,1H,J=1.8Hz),6.127(d,1H,J=1.8Hz),3.314-4.500(m,4H) ,2.800-3.310(m,4H),2.659(s,3H); 13 C NMR (125MHz, DMSO-d 6 ):δ160.323,158.034,157.942,154.540,150.314,127.565,117.495,115.207,102.131,99.354,94.136,49.441,48.731,46.183,43.711,16.995 HR Calcd.For CMS; 16 h 16 f 3 N 2 o 5 (M+H + )373.1011; found 373.1012.

Embodiment 3

[0118] N-Butyl-4-(5,7-dihydroxy-4-methyl-2-oxo-2H-benzopyran-3-yl)piperazine-1-amide (7A, R=n-butyl)

[0119]

[0120] According to Reaction Formula 1, dissolve 4 (0.1mmol) in anhydrous THF, add a small amount of DMF to aid in dissolution, add n-butyl isothiocyanate (0.12mmol), react at 50°C, and track and monitor with LC-MS. After the reaction is completed, evaporate Except for THF and DMF, the product was purified by silica gel column chromatography, the eluent was PE:EA=1:2, and the title compound was obtained as an off-white powder with a yield of 38%, m.p.245-248°C.

[0121] 1 H NMR (300MHz, DMSO-d 6 ): δ10.423(s, 1H), 10.191(s, 1H), 7.639(t, 1H J=5.1Hz), 6.253(d, 1H, J=2.4Hz), 6.118(d, 1H, J=2.4Hz ),3.480(m,2H),4.448(br,4H),2.925(br,4H),2.659(s,3H);1.515(m,2H),1.261(m,2H),0.882(t,3H, J=7.2Hz); HRMS Calcd.For C 19 h 26 N 3 o 4 S(M+H + )392.1644;found.392.1632.

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Abstract

The invention discloses novel coumarin compounds and pharmaceutically acceptable salts thereof, the preparation method of the compounds, pharmaceutical compositions containing the compounds, and application of the compounds to preparation of medicaments for prevention or treatment of cerebral diseases, especially prevention or treatment of diseases related to neuron damage and neuroinflammation, and prevention or treatment of Parkinson's disease, dementia, cerebral ischemia, depression and cerebral apoplexy.

Description

technical field [0001] The present invention relates to coumarin derivatives and a new medical application of such compounds, especially in the prevention and treatment of brain neurological and mental diseases such as stroke, dementia, Parkinson's disease and depression; field of medical technology. Background technique [0002] With the rapid development of modern society, the accelerated pace of life and work, coupled with the aging of the social population, major brain diseases, including neurological diseases and mental disorders (especially stroke, dementia, Parkinson, depression, etc.) Seriously endangering human health, it not only reduces the quality of life of patients, but also brings heavy economic burden to patients' families, which will also become a serious social problem. [0003] Modern medicine believes that the abnormal damage and loss of neurons is a common pathological feature of major brain diseases such as stroke, dementia, Parkinson, and depression. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/18A61K31/496A61P9/10A61P25/16A61P25/24
Inventor 刘刚陈乃宏孙明娜胡金风宋修云
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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