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Fused heterocyclic compound derivatives and their applications

A compound and drug technology, applied in the field of condensed heterocyclic compound derivatives, synthesis of condensed heterocyclic compound derivatives, preparation of drugs for the prevention or treatment of neuropsychiatric diseases, can solve problems such as QT gap prolongation

Active Publication Date: 2021-06-01
NHWA PHARMA CORPORATION +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have adverse effects such as QT gap prolongation, hyperprolactinemia and weight gain

Method used

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  • Fused heterocyclic compound derivatives and their applications
  • Fused heterocyclic compound derivatives and their applications
  • Fused heterocyclic compound derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080]

[0081] 1) Take 1,2,3,4-tetrahydroquinoline (5.0g), add acetone (50ml), then slowly add 3-chloropropionyl chloride (5.1g), stir until reflux, and the reaction is complete after 4 hours. The reaction mixture was cooled to room temperature, concentrated, dissolved in ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered with suction, and concentrated to obtain 8.0 g of an oil. Yield 96.4%.

[0082] 2) Take the product (8 g) of the first step, add anhydrous aluminum trichloride (7.2 g), and react under stirring for 3 hours. After cooling the reaction mixture to room temperature, ice water was added to quench the system. The reaction mixture was filtered, extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered with suction, and concentrated to obtain 6.05 g of solid. Yield 90.3%.

[0083]3) Take the product of the second step (5.0 g), add 2-chloroacetyl chloride (2.30 mL) and 1,2-dichloroethane (2...

Embodiment 2

[0087] The title compound was prepared according to the method of Example 1, but 3-chloropropionyl chloride was used instead of 2-chloroacetyl chloride.

[0088] 1H NMR (600MHz, CDCl3) δ7.76(s,1H),7.72(s,1H),7.21–7.11(m,2H),7.03–6.86(m,1H),3.93(dt,J=12.9,6.4 Hz,4H),3.42(t,J=6.8Hz,2H),3.20(t,J=7.3Hz,2H),3.11(s,4H),3.05–2.89(m,2H),2.87(d,J =6.2Hz,2H),2.79–2.65(m,2H),2.05–1.92(m,3H).

[0089] MS(ESI)m / z462.5([M+H]+)

Embodiment 3

[0091]

[0092] The target compound (0.5 g) of Example 2 was dissolved in anhydrous methanol (20 mL), and the reaction mixture was cooled to zero with an ice-water bath, sodium borohydride (0.08 g) was added thereto, and stirring was continued for 1 h. The reaction was quenched by adding 10 mL of water. The solvent was evaporated to dryness, an appropriate amount of dichloromethane was added, washed with water, and the aqueous layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain a pale yellow oil. Column chromatography gave 0.40 g of white solid.

[0093] 1H NMR (600MHz, CDCl3) δ7.71(dt, J=11.6,5.8Hz,1H),7.68(s,1H),7.66(s,1H),7.26(dd,J=8.5,2.0Hz,1H) ,7.12–7.02(m,1H),3.94–3.88(m,2H),3.20(t,J=7.3Hz,2H),3.10(dd,J=15.3,7.3Hz,3H),3.00–2.95(m ,2H),2.92(t,J=7.3Hz,2H),2.87(t,J=6.2Hz,2H),2.73–2.69(m,2H),2.30(t,J=12.5Hz,2H),2.14 –2.05(m,4H),1.99(dt,J=12.1,6.1Hz,2H),1.86-1.80(m,2H).MS(ESI)m / z464.7([M+H] + )

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to a condensed heterocyclic compound derivative and its application. The condensed heterocyclic compound derivative has a structure of general formula (I), and can be used for treating neuropsychiatric diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to the synthesis and application of a condensed heterocyclic compound derivative. More specifically, the present invention relates to a fused heterocyclic compound derivative, a pharmaceutical composition containing the fused heterocyclic compound derivative, and the preparation of the pharmaceutical composition and the fused heterocyclic compound derivative Or use in drugs for the treatment of neuropsychiatric diseases. Background technique [0002] Schizophrenia is a disorder characterized by deep cognitive and emotional dissociations that affect the most basic human behaviors, such as language, thought, perception, and self-awareness. The symptoms of the disease include a wide range, the most common being mental disorders, such as hallucinations, paranoia and delusions. Schizophrenia is the most serious mental illness, affecting about 1% of people worldwide, and on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/04C07D471/06A61K31/4745A61K31/496A61P25/18
CPCC07D455/04C07D471/06A61K31/4745A61K31/506A61K31/496A61P25/18
Inventor 张桂森曹旭东陈寅张译芳于民权邱印利徐祥清张探刘笔锋刘欣
Owner NHWA PHARMA CORPORATION
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