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COMT (catechol-O-methyltransferase) inhibitor containing hydrazide structure and preparation and application methods thereof

A C1-C4, C1-C5 technology, applied in the field of COMT inhibitors, can solve problems such as limited application

Inactive Publication Date: 2018-06-12
FOSHAN SAIWEISI MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although clozapine, Zyprexa, Vistron, and other antipsychotics have been used to treat both positive and negative (controversial) symptoms of schizophrenia and bipolar disorder, these drugs have not been free from side effects such as Cytopenia, sedation, weight gain, hyperlipidemia and hyperglycemia, all of which limit their use

Method used

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  • COMT (catechol-O-methyltransferase) inhibitor containing hydrazide structure and preparation and application methods thereof
  • COMT (catechol-O-methyltransferase) inhibitor containing hydrazide structure and preparation and application methods thereof
  • COMT (catechol-O-methyltransferase) inhibitor containing hydrazide structure and preparation and application methods thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 compound I-1

[0027]

[0028] Step 1. Synthesis of Compound VI-1

[0029] Compound II (1.32g, 20mmol) was dissolved in 20mL DMSO, stirred at room temperature, KOH solid (2.24g, 40mmol) was added, and stirred at room temperature for 1 hour. Further MeI (III-1, 2.84 g, 20 mmol) was added, and stirring was continued overnight at room temperature. Then tert-butyl bromoacetate V-1 (3.90 g, 20 mmol) was added, and the stirring was continued for 12 hours. TLC detection found that the reaction was complete.

[0030] The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed with 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by silica gel column chromatography to obtain compound VI-I,...

Embodiment 2

[0037] The synthesis of embodiment 2 compound 1-2

[0038]

[0039] Step 1. Synthesis of compound VI-2

[0040] Compound II (1.32g, 20mmol) was dissolved in 20mL DMSO, stirred at room temperature, KOH solid (2.24g, 40mmol) was added, and stirred at room temperature for 1 hour. Further MeI (III-1, 2.84 g, 20 mmol) was added, and stirring was continued overnight at room temperature. Then add 20mmol V-2 again, continue stirring for 12 hours, TLC detects that the reaction is complete. The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed with 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by silica gel column chromatography to obtain compound VI-2. ESI-MS, m / z=209 ([M+H] + ).

[0041] Step 2. Synthesis of Com...

Embodiment 3-9

[0046] With reference to the method of embodiment 1,2, synthesized following compound:

[0047]

[0048]

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Abstract

The invention relates to the field of COMT inhibitors, particularly to a COMT inhibitor containing a hydrazide structure, a preparation method of the COMT inhibitor, and application of the COMT inhibitor to preparing schizophrenia treating drugs and the like. The chemical formula of the COMT inhibitor is shown as below, in which R1 is an alkyl selected from C1-C5, R2 is selected from H, an alkyl of C1-C10 or a naphthene of C3-C10.

Description

technical field [0001] The present invention relates to the field of COMT inhibitors. Specifically, the present invention relates to a kind of COMT inhibitor containing a hydrazide structure, which has a therapeutic effect on inhibiting COMT, its preparation method and its use in the treatment of schizophrenia. Background technique [0002] Symptoms of schizophrenia are generally divided into three categories: positive, negative and cognitive. Positive symptoms include hallucinations, delusions, and disorganized behavior, while negative symptoms are characterized by a lack of pleasure and / or interest in life. Cognitive deficits include difficulty organizing thoughts and prioritizing tasks. Patients with bipolar disorder typically display cyclical mood swings (with or without psychotic features) from severe depression to severe mania. Schizophrenia and bipolar disorder are among the most severe types of mental disorders causing overlapping cognitive deficits and the disord...

Claims

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Application Information

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IPC IPC(8): C07D251/50A61P25/18
CPCC07D251/50
Inventor 蔡子洋
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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