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Tetrahydro-proto-berberine compounds, their preparing method, composition and use

A technology of tetrahydroprotoberberine and its compounds, applied in the fields of medicinal chemistry and chemotherapeutics, can solve the problems of uneffective treatment of nervous system diseases and unsatisfactory clinical treatment

Inactive Publication Date: 2007-01-24
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Nervous system diseases are one of the prevalent diseases in contemporary society. However, many neurological diseases have not been effectively treated clinically, especially schizophrenia is a serious mental disease, and its clinical treatment is far from satisfactory

Method used

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  • Tetrahydro-proto-berberine compounds, their preparing method, composition and use
  • Tetrahydro-proto-berberine compounds, their preparing method, composition and use
  • Tetrahydro-proto-berberine compounds, their preparing method, composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1: 3-methoxy-4-benzyloxy-ω-nitrostyrene (compound 1)

[0100] References (a.A.I.Meyeres & Joseph Guiles, Heterocycles, 1989, 28(1), 295-301.b. Paul W.Ford, Mathew R.Narbut, Jack Belli, and Bradley S.Davidson, J.Org.Chem., 1994, 59(20), 5955-5960), starting from vanillin, refluxing with benzyl bromide and potassium carbonate in acetone to obtain a benzyl-protected product, which was refluxed together with nitromethane and ammonium acetate in glacial acetic acid 3-Methoxy-4-benzyloxy-ω-nitrostyrene (1) is produced. M.P.117-119℃. 1 H NMR (CDCl 3 ): δ7.95(d, 1H, J=13.7Hz), 7.52(d, 1H, J=13.5Hz), 7.45-7.31(m, 5H), 7.11-7.02(m, 2H), 6.92(d, 1H, J=8.5Hz), 5.22(s, 2H), 3.93(s, 3H).

Embodiment 2

[0101] Example 2: 3-methoxy-4-benzyloxy-phenethylamine (compound 2)

[0102] Under the protection of argon, lithium aluminum tetrahydride (12.0g, 0.32mol) was suspended in pretreated anhydrous tetrahydrofuran (250ml), and compound 1 (28.5g, 0.10mol) was dissolved in anhydrous tetrahydrofuran (250ml), and stirred , slowly drop the latter into the previous suspension, control the drop rate to prevent the reflux from being too violent, heat and reflux for 2 hours after the dropwise addition, then stir overnight at room temperature, cool with ice water, and slowly drop the mixture under stirring Enter H 2 O (12ml), 15% sodium hydroxide solution (12ml), H 2 O (36ml), the formed turbidity was filtered, the filter cake was repeatedly washed with acetone, the filtrate was concentrated under reduced pressure and dissolved in ether (100-150ml), and the ether solution washed three times with water was dried with potassium carbonate and concentrated to dryness under reduced pressure. , ...

Embodiment 3

[0103] Example 3: 2-Chloro-4-benzyloxy-5-hydroxy-phenylacetic acid (compound 3)

[0104]It is prepared from 3,4-dihydroxybenzaldehyde with reference to literature (B Hegedus, Helv. Chim. Acta., 1963, 46(7), 2604-2612.). mp 100-102°C; 1 H NMR (CDCl 3 ): δ7.42-7.36(m, 5H), 6.90-6.87(m, 2H), 6.74(dd, 1H, J=2.1, 8.1Hz), 5.69(br, 1H), 5.09(s, 2H), 3.56(s, 2H).

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Abstract

The present invention provides tetrahydro protoberberine compounds as shown and their pharmaceutically acceptable inorganic or organic salts, crystallized hydrates, solvates and medicinal compositions. The present invention also provides their preparation process and application in preparing medicine for treating neurological diseases, especially dopamine acceptor related neurological diseases.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and chemotherapeutics, in particular to the synthesis of a class of tetrahydroprotoberberine compounds and their application in the field of preparing drugs for treating nervous system diseases, especially drugs for nervous system diseases related to dopamine receptors. Background technique [0002] Nervous system diseases are one of the prevalent diseases in contemporary society. However, many neurological diseases have not been effectively treated clinically, especially schizophrenia is a serious mental disease, and its clinical treatment is far from satisfactory. In recent years, neuroscientists have applied working memory operation [Working Memory Task] tests in animals and patients and short-term memory experiments that reflect the function of the prefrontal cortex (PFC) in the cerebral cortex [Castner, S.A. Science 2000, 287: 2020; Abi-Dargham, A .The J Neurosciences.2002, 22, 3708], as w...

Claims

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Application Information

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IPC IPC(8): C07D455/03C07D215/20C07C235/34A61K31/473A61P25/00
CPCC07D455/03A61P25/00A61P25/18
Inventor 杨玉社丁宇孙佩华莫骄金国章嵇汝运
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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