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Preparation method of tetrahydropyrrole compound

The technology of a compound and tetrahydrofuran is applied in the field of preparation of tetrahydropyrrole compounds to achieve the effects of improving negative symptoms of schizophrenia and cognitive function, simple operation and inhibitory effect

Inactive Publication Date: 2020-11-24
MEDICONNS SHANGHAI BIOPHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports of other compounds with similar structures as dual antagonists or inhibitors of D2 receptors and DAT receptors

Method used

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  • Preparation method of tetrahydropyrrole compound
  • Preparation method of tetrahydropyrrole compound
  • Preparation method of tetrahydropyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0070] step one

[0071] Synthesis of 3-methoxyvinylbenzene

[0072]

[0073] Dissolve methyltriphenylphosphine iodide (39.19g, 96.95mmol, 1.2eq) in 1,4-dioxane (500ml), and add potassium carbonate (16.75g, 121.19mmol, 1.5eq) under nitrogen protection , stirred at room temperature for 1 hour. 3-Methoxybenzaldehyde (11 g, 80.79 mmol, 1.0 eq) was added to the reaction system. Stir at 110° C. for 16 hours under nitrogen protection. The solvent was removed under reduced pressure, ethyl acetate (200ml) was added, washed with water (80ml×3), the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was purified by column chromatography (n-hexane) to obtain a yellow oily liquid (10g , yield 92%).

[0074] step two

[0075] Synthesis of 1-Benzyl-3-(3-methoxyphenyl)pyrrolidine

[0076]

[0077] 3-Methoxyvinylbenzene (10g, 74.5mmol, 1eq) was dissolved in dichloromethane (250mL), trifluoroacetic acid (0.85g, 7.45mmol, 0.1eq) was added,...

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Abstract

The invention discloses a preparation method of a tetrahydropyrrole compound. According to the preparation method, common easily available 3-methoxybenzaldehyde is used as an initial raw material, a compound 002 is obtained through a Wttig reaction, a cyclization reaction, a debenzylation reaction, a reductive amination reaction and a deprotection reaction, and the operation is simple. In addition, the compound 002 provided by the invention has a relatively good inhibition effect on positive symptoms of schizophrenia, and also has very good improvement on negative symptoms of schizophrenia andcognitive functions.

Description

technical field [0001] The invention relates to a preparation method of tetrahydropyrrole compounds. Background technique [0002] Schizophrenic disorder is an extremely serious mental illness, which can be classified into three types: positive symptoms, negative symptoms, and impairment of recognition and memory. Positive symptoms, manifested as hallucinations and delusions, restlessness, paranoia, thought disturbance and abnormal behavior; Negative symptoms, manifested as blunted affect, reticence, lack of interest, anhedonia, and withdrawn and withdrawn; identification Cognitive Deficits, manifested as inability to concentrate, severe memory loss, and inability to act as planned. [0003] The first-generation and second-generation schizophrenia drugs currently in clinical use have a relatively good therapeutic effect on positive symptoms, and can reduce or eliminate symptoms such as delusions, hallucinations, and thinking disorders. However, almost all clinical drugs ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A61P25/18
CPCA61P25/18C07D403/06
Inventor 党柱克里斯汀·珏蔡雒震王刘刚鲍丹
Owner MEDICONNS SHANGHAI BIOPHARM CO LTD