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2-(2-Chlorophenyl)quinazolin-4(3h)-one derivatives and their preparation methods and uses

A technology of quinazoline and chlorophenyl, which is applied in the field of pharmaceutical research, can solve problems such as dizziness, cognition and memory impairment, drug daytime sleepiness, abuse, etc., and achieve the reduction of next-day residual effects, strong drug efficacy, and fast metabolism fast effect

Active Publication Date: 2020-10-30
ACADEMY OF MILITARY MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing drugs have daytime drowsiness, dizziness, cognitive and memory impairment, and long-term application is prone to tolerance and dependence (J ClinPsychiatry, 2004, 65(8): 20-25.), and has a tendency to lead to abuse

Method used

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  • 2-(2-Chlorophenyl)quinazolin-4(3h)-one derivatives and their preparation methods and uses
  • 2-(2-Chlorophenyl)quinazolin-4(3h)-one derivatives and their preparation methods and uses
  • 2-(2-Chlorophenyl)quinazolin-4(3h)-one derivatives and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1, 2-(2-Chlorophenyl)-3-(3-Chlorophenyl)quinazolin-4-(3H)one (Compound No.: ZXW9043)

[0070]

[0071] The first step, the preparation of 2-nitro-N-phenylbenzamide

[0072]

[0073] Weigh 2.0g (0.012mol) of o-nitrobenzoic acid and place it in a 100mL reaction flask, add 7.1g (0.06mol) of thionyl chloride, place the reaction flask in an oil bath, heat to reflux at 80°C, and after 2 hours Terminate the reaction, concentrate under reduced pressure to remove the solvent, add 20 mL of dichloromethane, concentrate again under reduced pressure to remove the solvent, and obtain a light yellow oil, add 20 mL of dichloromethane to form an acid chloride solution for use. Add 1.52g (0.012mol) of 3-chloroaniline to a 100mL reaction flask, add 1.42g (0.018mol) of pyridine, dissolve with 20mL of dichloromethane, add a dropping funnel to the reaction flask, vacuum nitrogen protection, put the reaction flask into In an ice bath, put the acid chloride solution in a droppin...

Embodiment 2

[0080] Example 2 2-(2-chlorophenyl)-3-(2,4-dimethoxyphenyl)quinazolin-4-(3H)one (compound number: ZXW9044R2)

[0081]

[0082] Using 2-amino-N-(2,4-dimethoxyphenyl)benzamide and 2-chlorobenzaldehyde as raw materials, according to the synthesis method described in Example 1, 150 mg of white solid was obtained, yield: 71.4%. 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 8.24-8.21 (dd, J 1 =8.1Hz,J 2 =1.1Hz,1H,ArH),7.94–7.90(m,1H,ArH),7.77(d,J=8.1Hz,1H,ArH),7.69-7.56(m,2H,ArH),7.38-7.10(m ,4H,ArH),6.93-6.82(m,2H,ArH),3.68(s,3H,OCH 3 ),3.61(s,3H,OCH 3 ); 13 C NMR (100MHz, CDCl 3 )δ (ppm): 162.3, 153.3, 148.9, 147.2, 134.9, 134.8, 132.0, 130.6, 130.3, 129.6, 127.8, 127.7, 127.3, 126.6, 121.4, 121.2, 121.2, 120.5, 112.1, 111.0; ESI, m / z) calculated value C 22 h 18 ClN 2 o 3 [(M+H) + ], 393.1000; measured value, 393.0999.

Embodiment 3

[0083] Example 3 2-(2-chlorophenyl)-3-[(3-phenylamino)phenyl]quinazolin-4-(3H)one (compound number: ZXW1102R2)

[0084]

[0085] Using 2-amino-N-(3-(phenylamino)phenyl)benzamide and 2-chlorobenzaldehyde as raw materials, according to the synthesis method described in Example 1, 280 mg of white solid was obtained, yield: 65.9%. 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):8.23(d,J 1 =7.8Hz,1H,ArH),7.95-7.89(m,2H,ArH),7.76(d,J=8.1Hz,1H,ArH),7.65-7.61(m,1H,ArH),7.43-7.31(m ,3H,ArH),6.70-6.67(m,4H,ArH),7.09-6.92(m,4H,ArH),6.70-6.67(m,1H,ArH); 13 C NMR (100MHz, DMSO-d 6 )δ (ppm): 161.9, 153.6, 147.7, 142.4, 141.4, 135.0, 134.8, 131.4, 130.2, 129.7, 129.4, 129.3, 127.9, 127.8, 127.0, 126.8, 122.5, 122.1, 120.3, 119.3; ESI, m / z) calculated value C 26 h 19 ClN 3 O[(M+H) + ], 424.1211; measured value, 424.1211.

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Abstract

The invention discloses a 2-(2-chlorophenyl) quinazoline-4 (3H)-one derivative shown in formula (I) or pharmaceutically acceptable salts thereof. Compared with the existing first-line sedative and hypnotic drugs diazepam and midazolam, the compound has stronger drug effect and faster metabolism speed, can reduce the next-day residual effect, and is expected to be developed into a novel high-efficiency low-toxicity sedative and hypnotic drug.

Description

technical field [0001] The present invention belongs to the field of pharmaceutical research, and in particular relates to 2-(2-chlorophenyl)quinazolin-4(3H)-one derivatives, their preparation methods, and their use in the preparation of sedative-hypnotic, anticonvulsant, antidepressant, The use of anti-anxiety and other drugs. Background technique [0002] The global incidence of sleep disorders is as high as 27%, and it has become one of the major health problems of human concern. Sedative and hypnotic drugs commonly used in clinical practice have adverse reactions such as cognitive and memory impairment, fragmented disturbance of consciousness and memory loss. Therefore, it is of great clinical significance to develop sedative-hypnotics with high efficiency, low toxicity and no next-day residue. [0003] GABA A Receptor is an important target of sedative-hypnotics, GABA A Receptor agonists are the most widely used sedative-hypnotic drugs in clinical practice, includin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/91C07D405/04A61K31/517A61P25/20A61P35/00A61P31/04A61P31/18A61P31/06A61P25/16A61P29/00A61P9/00A61P25/08
CPCA61P9/00A61P25/08A61P25/16A61P25/20A61P29/00A61P31/04A61P31/06A61P31/18A61P35/00C07D239/91C07D405/04
Inventor 何新华苏瑞斌俞刚张宪伟曹燕卿庄笑梅
Owner ACADEMY OF MILITARY MEDICAL SCI
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