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Leavo halogenated salt and its preparation process and use

A linoline salt and salt-forming technology, which can be used in nervous system diseases, organic chemistry, drug combination, etc., can solve the problems of unstable free base of levoscurliline, unfavorable pharmacology and pharmaceutical preparation research, and many impurities.

Inactive Publication Date: 2007-10-31
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the Shanghai Institute of Materia Medica, Chinese Academy of Sciences has synthesized levo-closculoline (l-CSL) (ZL94112235.2), the free base of levo-closculoline is unstable and has poor solubility, which is not conducive to subsequent pharmacology and Research on Pharmaceutical Preparations
And the impurity that key two-step reaction produces in its synthetic method is more, and yield is very low, is unfavorable for large-scale production

Method used

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  • Leavo halogenated salt and its preparation process and use
  • Leavo halogenated salt and its preparation process and use
  • Leavo halogenated salt and its preparation process and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1 3-methoxy-4-benzyloxybenzaldehyde (I)

[0077] Vanillin (240g, 1.58mol) was dissolved in ethanol (or other lower alcohols as mentioned above) (500ml); KOH (132.7g, 2.37mol) (or other inorganic bases as mentioned above) was dissolved in In water (90ml), a KOH solution was made. Add the KOH solution into the vanillin ethanol solution, the solution becomes solid, and the temperature is raised to about 80°C to dissolve the solid, and after it is completely dissolved, slowly add benzyl chloride (or other benzyl halides as mentioned above) (1.89mol) dropwise, After dripping, continue to reflux for about 2 hours. After TLC detects that there is basically no raw material, the reaction solution is concentrated and evaporated to remove ethanol, and the residue is poured into a strong alkaline aqueous solution of KOH with stirring. The oil was flocculent first and then solidified. It was filtered by suction, and the obtained solid was washed with an aqueous KOH solut...

Embodiment 2

[0078] Example 2 3-methoxy-4-benzyloxybenzaldehyde (I)

[0079] Vanillin (240g, 1.58mol) was dissolved in 95% ethanol (or the mixed solvent of other lower alcohols and water as mentioned above) (500ml), and potassium carbonate (or other inorganic bases as mentioned above) (3.05mol) was added , the solution became solid, and the temperature was raised to about 80°C to dissolve the solid, and after complete dissolution, benzyl bromide (or other benzyl halides as mentioned above) (1.89 mol) was added slowly, and the reaction was refluxed for 4 hours. Aftertreatment is with embodiment 1.

Embodiment 3

[0080] Example 3 3-methoxyl-4-benzyloxybenzaldehyde (I)

[0081] Vanillin (240g, 1.58mol), DMSO (or other solvents as previously described) (400ml), triethylamine (or other organic bases as previously described) (3.85mol) and benzyl chloride (or other solvents as previously described The above-mentioned other benzyl halides) (1.89mol) were mixed and reacted at 70°C for 6 hours. Aftertreatment is with embodiment 1.

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Abstract

This invention relates to a tetrahydropyranyl ether proto little alkali category compound laevorotation halogenating si ku li lin salt. The salt has anti- schizophrenia effect by medicine theory, especially comparing to laevorotation chlorine si ku li lin, the laevorotation chlorine si ku li lin methanesulfonic acid salt has great solubility and stability. It is propitious to following research and conditions are created to make effective medicine preparation.

Description

technical field [0001] The invention relates to a method for preparing tetrahydroprotoberberine analogues of general formula and pharmaceutically acceptable salts thereof, wherein said compound has brain dopamine D 1 receptor subtype agonist-D 2 Receptor subtype blockade has dual effects and can be used to treat diseases of the central nervous system, such as schizophrenia, ADHD, and migraine. In particular the invention relates to the preparation and use of their physiologically acceptable salts having effective pharmaceutical properties for use as medicaments. Background technique [0002] Recent studies have shown that the prefrontal cortex D in patients with schizophrenia 1 Receptor dysfunction, while subcortical D 2 Receptor hyperfunction. The treatment of schizophrenia should be balanced D 1 、D 2 Functions of two dopamine receptor subtypes. Therefore, with brain dopamine D 1 receptor subtype agonist-D 2 Drugs with dual effects of receptor subtype blockade shou...

Claims

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Application Information

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IPC IPC(8): C07D455/03A61P25/00
Inventor 李剑峰索瑾夏广新金文桥沈敬山
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI