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Tandospirone citrate, preparation method thereof, formulations and quality control method

A tandospirone citrate, quality technology, applied in the field of high-purity tandospirone citrate, can solve the problem of unfavorable large-scale production, no tandospirone synthesis process impurity components, structure and properties, high production costs

Active Publication Date: 2009-02-11
SICHUAN CREDIT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But its synthetic method is compared with this patent, and its production cost is high, and yield is low, is unfavorable for large-scale production
[0005] At present, there is no synthetic method for preparing tandospirone by condensation of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide and quaternary ammonium salt, nor does it use maleic acid imide and cyclic Pentadiene is reacted and hydrogenated to make cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide, and there is no use of high-purity cis-exo-bicyclo[2.2.1] ]heptane-2.3-dicarboximide to prepare high-purity tandospirone report, and there is no HPLC method for cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide Untransformed cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide and unreduced cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide There is no report on the analysis and quality control of tandospirone, and there is no report on the composition, structure and properties of impurities in the synthesis process of tandospirone, and there is no specific report on the impact of which impurity on the efficacy and safety of tandospirone. to report

Method used

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  • Tandospirone citrate, preparation method thereof, formulations and quality control method
  • Tandospirone citrate, preparation method thereof, formulations and quality control method
  • Tandospirone citrate, preparation method thereof, formulations and quality control method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Preparation of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide of the present invention

[0056]

[0057] The transformation product is obtained by transformation of norbornene diacid anhydride at 190-210 ° C, and the transformation product is hydrogenated under the condition of palladium carbon as a catalyst to obtain a hydride, and the hydride is ammoniated with ammonia water to obtain cis-exo-bicyclic [2.2.1 ] Heptane-2.3-dicarboximide.

Embodiment 2

[0058] Example 2 Another preparation scheme of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide of the present invention:

[0059]

[0060] Add 97g of maleimide to the reaction flask, add 1000ml of ethyl acetate, stir to dissolve, add 93g of cyclopentadiene, stir for 24 hours, evaporate 75% of the solvent under reduced pressure, filter, wash and filter with an appropriate amount of ether Cake to obtain 163 g of the specific configuration, with a yield of about 86%. Dissolve 163g of the specific configuration in 2500ml of THF, add 163g of cyclohexene and 5g of 5% palladium carbon, feed hydrogen at a pressure greater than 0.01MPa, and reflux the reactant for 9h. After cooling, evaporate the solvent under reduced pressure. The residue was recrystallized from toluene to obtain 161 g of the product, with a yield of about 98%. The purity of the cis-outer-bicyclo[2.2.1]heptane-2.3-dicarboximide obtained by this method meets the high-purity cis-outer-bicyclo[2.2.1]heptane described...

Embodiment 3

[0061] Example 3 The quality control method of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide of the present invention

[0062] The quality of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide prepared in Examples 1 and 2 was measured.

[0063] The purity of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide was determined according to the "Operating Procedures for High Performance Liquid Chromatography".

[0064] Chromatographic conditions and system suitability test use octadecylsilane bonded silica gel as filler; 0.01mol / L potassium dihydrogen phosphate solution (adjust pH to 7.5 with 10% sodium hydroxide solution)-acetonitrile (80:20) is Mobile phase; detection wavelength is 243nm. The number of theoretical plates calculated based on the peak of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide should not be less than 1500.

[0065] Determination method Take about 0.1g of cis-exo-bicyclo[2.2.1]heptane-2.3-dicarboximide, put it in a 10ml measuring bottle, add mobile phase to di...

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Abstract

The invention provides citrate tandospirone which is characterized by comprising a compound I with the weight percent content not more than 0.5 percent and a compound II with the weight percent content not more than 0.5 percent. The structure formulas of the compound I and the compound II are as the right formulas. The invention also provides a preparation method and a quality control method of the citrate tandospirone. The results of a pharmacodynamic test and clinical observation show that after the quality standard of the citrate tandospirone is improved, the effect of clinical antianxiety is obviously improved and untoward effect is obviously reduced.

Description

technical field [0001] The invention relates to tandospirone citrate, in particular to high-purity tandospirone citrate, and belongs to the field of medicines. Background technique [0002] Tandospirone belongs to the spirone class of drugs and is a 5-HT receptor agonist, which is highly selective to 5-HT 1A receptor binding. 5-HT 1A Receptors are mainly concentrated in the hippocampus, septum, interpeduncular nucleus, amygdala and other brain limbic systems and suture gland nuclei. Tandospirone selectively stimulates 5-HT in postsynaptic membranes. Inhibit hyperactive 5-hydroxytryptaminergic nerve activity, make 5-HT and 5-HT of post-synaptic membrane 1A and 5-HT 2A The combination of receptors restores the balance state, thereby exerting an anti-anxiety effect, and does not produce side effects such as muscle relaxation and anti-convulsions of benzodiazepine anti-anxiety drugs. Preclinical test data show that the anti-anxiety effect of tandospirone is similar to that...

Claims

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Application Information

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IPC IPC(8): C07D403/12A61P25/00
Inventor 陈功政胡和平王永朝陈刚
Owner SICHUAN CREDIT PHARMA
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