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Flavonoid derivative and application thereof

A technology of flavonoids and derivatives, applied to flavonoid derivatives and their application fields, can solve problems such as QT interval prolongation

Active Publication Date: 2014-09-24
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the atypical antischizophrenic drugs currently in clinical use all have adverse reactions such as QT interval prolongation and high prolactin to varying degrees]

Method used

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  • Flavonoid derivative and application thereof
  • Flavonoid derivative and application thereof
  • Flavonoid derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)spiro[chroman-2-1'-cyclopentane]-4-one (1)

[0078] Reaction 1

[0079]

[0080] 1) Take 7.6g of 2,4-dihydroxyacetophenone, 8.4g of cyclopentanone, and 7.1g of tetrahydropyrrole, add 50ml of anhydrous acetonitrile, and react at 50°C for 12h. TLC detection, the reaction is completed, cooled to room temperature, the solution is slowly poured into 2M hydrochloric acid ice-water mixture, a solid precipitates, stirred for 30 minutes, filtered to obtain a yellow solid, recrystallized with 95% ethanol to obtain a white solid, and dried to obtain the product 8.4g, melting point 186‐188°C, yield 77.1%.

[0081] 2) Take 4.2g of the first step product, 6g of anhydrous potassium carbonate, 50ml of acetone, 8.2g of 1,4‐dibromobutane, heat and reflux for 6 hours, cool to room temperature, filter, evaporate the solvent to dryness, and use eluent Petroleum ether: ethyl acetate 4:1 was passed through the column to obtain 5.6 ...

Embodiment 2

[0082] Example 2, 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)butoxy)helix [chroman-2-1'- Cyclopentane]‐4‐one (2)

[0083] Replace 2-methoxyphenylpiperazine hydrochloride with 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride, prepared according to the method of Example 1 The target compound 2 was obtained: 7‐(4‐(4‐(6‐fluorobenzo[d]isoxazol‐3‐yl)piperidin‐1‐yl)butoxy)helix [chroman‐2‐1' ‐cyclopentane]‐4‐one.

[0084] Melting point: 103-105°C. 1 H NMR (CDCl 3 )δ1.63‐1.90(m,10H),2.07‐2.19(m,8H),2.48(t,2H,J=8Hz),2.78(s,2H),3.08‐3.12(m,4H),4.04( t, 2H, J=8Hz), 6.38(d, 1H, J=4Hz), 6.54-6.56(m, 1H), 7.04-7.09(m, 1H), 7.24-7.26(m, 1H), 7.69-7.73 (m,1H),7.80(d,1H,J=8Hz).MS (ESI) m / z493.3([M+H] + )

Embodiment 3

[0085] Example 3, 7-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)spiro[chroman-2-1'-cyclopentane-4-one ( 3)

[0086] With 1,3-dibromopropane instead of 1,4-dibromobutane, target compound 3 was prepared according to the method of Example 1: 7-(3-(4-(2-methoxyphenyl)piperazine- 1-yl)propoxy)helix[chroman-2-1'-cyclopentane-4-one.

[0087] Melting point: 128-130°C. 1 H NMR (CDCl 3 )δ1.65‐1.74 (m, 4H), 1.87‐1.91 (m, 2H), 2.03‐2.12 (m, 4H), 2.61 (t, 2H, J=8Hz), 2.71 (s, br, 4H), 2.79(s,2H),3.13(s,br,4H),3.89(s,3H),4.09(t,2H,J=8Hz),6.41(d,1H,J=4Hz),6.55‐6.58(m ,1H),6.88‐7.04(m,4H),7.81(d,1H,J=8Hz).MS (ESI) m / z451.2([M+H] + )

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Abstract

The present invention belongs to the field of pharmaceutical chemistry, and, in particular, disclosed therein are a flavonoid derivative and use thereof. Disclosed is a flavonoid derivative having the structure of general formula (I) or a pharmaceutically acceptable salt thereof. This compound can be used in the preparation of drugs for preventing or treating central nervous system diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to flavonoid derivatives and applications thereof. Background technique [0002] Schizophrenia has a history of more than one hundred years as an independent disease unit. In 1896, on the basis of summarizing the work of predecessors, Kraepelin summarized several clinical phenomena previously proposed into one disease, which he called dementia praecox; Disorders of volition and autism have at their core schizophrenia, which is still used today. [0003] Schizophrenia is the most serious and harmful disease among all mental diseases], with a global incidence of about 1‐2%. Patients with schizophrenia have a lifetime prevalence of 0.7-0.8%, with no apparent relationship to sex, race, or social boundaries, and a mortality rate 2-3 times higher than in the general population. The latest research shows that the social burden of mental illness ranks first among diseases i...

Claims

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Application Information

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IPC IPC(8): C07D311/96C07D413/14C07D417/12C07D491/107A61K31/496A61K31/454A61K31/4545A61P25/00A61P25/18
CPCC07D413/14C07D407/14C07D405/14C07D405/12A61K31/496C07D407/12C07D311/96C07D417/12C07D491/107A61P25/00A61P25/18C07D311/22
Inventor 陈寅徐祥清赵松于民权邱印利张桂森
Owner NHWA PHARMA CORPORATION
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