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First-class phenylmethylamine triazine structural COMT inhibitor, as well as preparation method and application thereof

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

Inactive Publication Date: 2018-06-22
FOSHAN SAIWEISI MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 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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  • First-class phenylmethylamine triazine structural COMT inhibitor, as well as preparation method and application thereof
  • First-class phenylmethylamine triazine structural COMT inhibitor, as well as preparation method and application thereof
  • First-class phenylmethylamine triazine structural COMT inhibitor, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Synthesis of Compound I-1

[0021]

[0022] Step 1. Synthesis of compound VI-1

[0023] Compound II (1.32g, 20mmol) was dissolved in 20mL DMSO, stirred at room temperature, KOH solid (2.24g, 40mmol) was added, and stirring was continued for 1 hour at room temperature. Then MeI (III-1,2.84g, 20mmol) was added, and stirring was continued overnight at room temperature. Then, tert-butyl bromoacetate V-1 (3.90 g, 20 mmol) was added, and stirring was continued for 12 hours. TLC detection revealed that the reaction was complete.

[0024] The reaction mixture was carefully poured into 200mL ice water, stirred, and 50mL×3CH 2 Cl 2 After extraction, the extracts 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, 2.99 g (combined yield 77%)....

Embodiment 2

[0031] Example 2 Synthesis of Compound I-2

[0032]

[0033] Step 1. Synthesis of compound VI-2

[0034] Compound II (1.32g, 20mmol) was dissolved in 20mL DMSO, stirred at room temperature, KOH solid (2.24g, 40mmol) was added, and stirring was continued for 1 hour at room temperature. Then MeI (III-1,2.84g, 20mmol) was added, and stirring was continued overnight at room temperature. Then 20mmol V-2 was added and stirring was continued for 12 hours. TLC detection revealed that the reaction was complete. The reaction mixture was carefully poured into 200mL ice water, stirred, and 50mL×3CH 2 Cl 2 After extraction, the extracts 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] + ).

[0035] Step 2. Synthesis of compound VII-2...

Embodiment 3-5

[0040] With reference to the methods of Examples 1 and 2, the following compounds were synthesized:

[0041]

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PUM

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Abstract

The invention relates to the field of COMT inhibitors, specifically to a first-class phenylmethylamine triazine structural COMT inhibitor as well as a preparation method and application thereof to preparation of drugs for treating schizophrenia. The formula is shown in the description, wherein R is selected from an alkyl group and halogen substituent of H and C1-C5.

Description

Technical field [0001] The present invention relates to the field of COMT inhibitors. Specifically, the present invention relates to a class of COMT inhibitors containing a benzylaminotriazine structure that has a therapeutic effect on COMT inhibition, its preparation method, and its use in the treatment of schizophrenia. Background technique [0002] The symptoms of schizophrenia are usually divided into three categories: positive, negative and cognitive. Positive symptoms include hallucinations, delusions, and confused behavior, while negative symptoms are characterized by a lack of pleasure and / or interest in life. Cognitive deficits include difficulties in organizing ideas and prioritizing tasks. Patients with bipolar disorder usually show periodic mood changes (with or without features of psychosis) from severe depression to severe mania. Schizophrenia and bipolar disorder are among the most serious types of mental disorders that cause overlapping cognitive deficits and t...

Claims

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Application Information

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