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Nitrogenous benzheterocycle derivate and application thereof to treating nervous and mental diseases

A nitrogen heterocycle and derivative technology is applied to benzo nitrogen-containing heterocycle derivatives and their application in the field of drugs for treating neuropsychiatric diseases, and can solve the problems of elevated prolactin, narrow therapeutic spectrum, obvious extrapyramidal symptoms, etc. question

Inactive Publication Date: 2010-05-26
JIANGSU HENGYI PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the technical problems to be solved in the present invention is to disclose a benzo nitrogen-containing heterocyclic derivative to overcome the shortcomings of existing drugs such as slow onset of action, narrow therapeutic spectrum and side effects such as obvious extrapyramidal symptoms and elevated prolactin. Solve clinical problems and meet clinical drug needs;

Method used

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  • Nitrogenous benzheterocycle derivate and application thereof to treating nervous and mental diseases
  • Nitrogenous benzheterocycle derivate and application thereof to treating nervous and mental diseases
  • Nitrogenous benzheterocycle derivate and application thereof to treating nervous and mental diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] I-1 7-(4-(3,4-dihydro-2[1H]isoquinolinyl) n-butoxy)-3,4-dihydro-2(1H)quinolone hydrochloride as 1,2 , 3,4-tetrahydroisoquinoline, 1-bromo-4-chloro-butane and 7-hydroxyl-3,4-dihydro-2 (1H) quinolones are raw materials, and 7-( 4-(3,4-dihydro-2[1H]isoquinolinyl)-n-butoxy)-3,4-dihydro-2(1H)quinolone, dissolve the compound in hot absolute ethanol, drop Add hydrochloric acid ethanol to pH = 3, let cool, precipitate white powder, filter, wash with absolute ethanol, and dry at low temperature to obtain the target compound.

[0100] Elemental Analysis: C 22 h 26 N 2 o 2 .HCl.2H 2 O (Theoretical %: C 62.48, H 7.39, N 6.62; Experimental % C62.40, H 7.41, N 6.67)

[0101] 1 HNMR (DMSO-d 6 ): 7.2-7.4(m, 4H, aromatic ring-H), 7.06(d, 1H), 6.51(d, 1H), 6.47(d, 1H), 4.5(d, 1H), 4.3(d, 1H) , 3.95(t, 2H), 3.7(t, 1H), 3.24(m, 3H), 3.11(d, 1H), 2.79(t, 2H), 2.42(t, 2H), 1.90(m, 2H), 1.78 (m, 2H)

[0102] MS: m / e 350.2.

Embodiment 2

[0104] I-2 7-(3-(3,4-dihydro-2[1H]isoquinolinyl)n-propoxy)-3,4-dihydro-2(1H)quinolone hydrochloride

[0105] Using 1,2,3,4-tetrahydroisoquinoline, 1-bromo-3-chloro-propane and 7-hydroxy-3,4-dihydro-2(1H)quinolone as raw materials, prepared according to General Method IV To obtain 7-(3-(3,4-dihydro-2[1H]isoquinolinyl)-n-propoxy)-3,-dihydro-2(1H)quinolone, the compound was dissolved in hot anhydrous In ethanol, add hydrochloric acid ethanol dropwise to pH = 3, let cool, precipitate white powder, filter, wash with absolute ethanol, and dry at low temperature to obtain the target compound.

[0106] Elemental Analysis: C 21 h 24 N 2 o 2 .HCl.H 2 O (Theoretical %C 64.52, H 6.96, N 7.17; Experimental %C64.58, H 7.03, N 7.12)

[0107] 1 HNMR (DMSO-d 6 ): 7.20-7.41(m, 4H), 7.02(d, 1H), 6.51(dd, 1H), 6.47(d, 1H), 4.52(d, 1H), 4.31(d, 1H), 3.95(t, 2H), 3.7(t, 1H), 3.23(m, 3H), 3.11(d, 1H), 2.75(t, 2H), 2.41(t, 2H), 1.90(m, 2H)

[0108] MS: m / e 336.2.

Embodiment 3

[0110] I-3 7-(2-(3,-dihydro-2[1H]isoquinolinyl)ethoxy)-3,4-dihydro-2(1H)quinolone hydrochloride

[0111] Using 1,2,3,4-tetrahydroisoquinoline, 1-bromo-2-chloro-ethane and 7-hydroxy-3,4-dihydro-2(1H)quinolone as raw materials, according to the general method four To obtain 7-(2-(3,4-dihydro-2[1H]isoquinolyl)ethoxy)-3,4-dihydro-2(1H)quinolone, dissolve the compound in hot absolute ethanol , add hydrochloric acid ethanol dropwise to pH = 3, let cool, precipitate white powder, filter, wash with absolute ethanol, and dry at low temperature to obtain the target compound.

[0112] Elemental Analysis: C 20 h 22 N 2 o 2 .HCl (Theoretical %: C 66.94, H 6.46, N 7.81; Experimental %C 66.90H 6.40, N 7.88)

[0113] 1 HNMR (DMSO-d 6 ): 7.15-7.47(m, 4H), 7.03(d, 1H), 6.53(dd, 1H), 6.45(d, 1H), 4.51(d, 1H), 4.30(d, 1H), 3.96(t, 2H), 3.72(t, 1H), 3.24(m, 3H), 3.10(d, 1H), 2.75(t, 2H), 2.41(t, 2H)

[0114] MS: m / e 322.2.

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Abstract

The invention discloses a nitrogenous benzheterocycle derivate and application thereof to treating nervous and mental diseases. Pharmacology experiments show that the derivate has better anti-schizophrenia action and lower toxicity. The derivate is free alkali or salt having the following structure general formula.

Description

technical field [0001] The invention relates to a benzo nitrogen-containing heterocyclic derivative, a preparation method and application thereof. Background of the invention [0002] Schizophrenia is a common severe mental illness, the most serious and harmful of all mental illnesses, with a global incidence of about 1%. With the deterioration of the social environment and the increasing pressure of life , the incidence rate showed a clear upward trend. Most schizophrenic patients give up treatment due to the long treatment cycle, high cost, and large side effects, which often lead to more serious social consequences. [0003] A large number of studies have shown that the dopamine system and serotonin system in the brain are closely related to the normal mental activities of the human body. For example, the disturbance of the above two neurotransmitters can lead to a variety of neuropsychiatric diseases, such as schizophrenia, neuropathic pain, mania , anxiety disorder, P...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D413/12A61K31/4725A61P25/18
Inventor 李建其彭少平蔡王平
Owner JIANGSU HENGYI PHARMA
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