Synthetic method of tropisetron and prepare method of hydrochloric acid tropisetron

A synthetic method, the technology of tropisetron, applied in the field of chemical pharmaceuticals, to achieve the effects of simplified synthesis steps, less pollution, and easy preparation process

Active Publication Date: 2012-07-04
NEW FOUNDER HLDG DEV LLC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] At present, there is no method for preparing tropisetron or tropi...

Method used

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  • Synthetic method of tropisetron and prepare method of hydrochloric acid tropisetron
  • Synthetic method of tropisetron and prepare method of hydrochloric acid tropisetron
  • Synthetic method of tropisetron and prepare method of hydrochloric acid tropisetron

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preparation example Construction

[0049] The present invention also provides a simple method for preparing high-purity tropisetron hydrochloride. The method first realizes direct esterification synthesis of tropisetron through suitable catalyst and reaction conditions (specific conditions as described above), and then through acidification Step (including extracting the tropisetron obtained by esterification into an aqueous mineral acid solution), alkali adjustment step (including adjusting the pH value to 9-10, so that the crude product of tropisetron is precipitated from water), refining step (including using hydrochloric acid ethanol solution for salt formation and crystallization) to obtain Tropisetron Hydrochloride.

[0050] After the reaction for synthesizing tropisetron is completed, tropisetron is placed in an organic solvent, and the tropisetron is extracted into an aqueous solvent through an acidification step, preferably using an aqueous mineral acid solution to extract tropisetron. The aqueous inor...

Embodiment 1

[0068] Add indole-3-carboxylic acid (20 g, 0.124 mol), p-toluenesulfonic acid (0.75 g, 0.00434 mol), ethyl acetate (230 ml), freshly activated 4A molecular sieves (0.5-1.0 mm) (3 g) In a 500ml three-necked reaction flask equipped with a thermometer and a reflux condenser, start to heat up after stirring evenly, and the temperature is controlled at 75-77°C, then slowly add tropinol (19.3 grams, 0.137mol) dropwise, and reflux after the dropwise addition React for 10 hours.

[0069] Stop the reaction, extract the product three times with 100ml of 1mol / L hydrochloric acid in the organic layer, combine the aqueous phases, and wash once with 50ml of ethyl acetate. The aqueous phase was adjusted to pH 9-10 with 4 mol / L sodium hydroxide aqueous solution, and a light yellow solid was precipitated. The filter cake was suction filtered and washed with distilled water until neutral, and dried under reduced pressure to obtain 32.7 g of crude tropisetron. Dissolve the above crude product i...

Embodiment 2

[0071] Indole-3-carboxylic acid (20 g, 0.124 mol), benzenesulfonic acid (0.791 g, 0.005 mol), ethyl acetate (230 ml), freshly activated 4A molecular sieves (0.5-1.0 mm) (3 g) were added to In the 500ml three-necked reaction flask equipped with a thermometer and a reflux condenser, start to heat up after stirring evenly, and the temperature is controlled at 75°C-77°C, then slowly add tropinol (19.3 grams, 0.137mol) dropwise, and reflux after the dropwise addition React for 11 hours.

[0072] Stop the reaction, extract the product three times with 100ml of 1mol / L hydrochloric acid in the organic layer, combine the aqueous phases, and wash once with 50ml of ethyl acetate. The aqueous phase was adjusted to a pH of 9-10 with 4 mol / L sodium hydroxide aqueous solution, and a yellow solid was precipitated. The filter cake was suction filtered and washed with distilled water until neutral, and dried under reduced pressure to obtain 33.1 g of crude tropisetron. Dissolve the above crude...

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Abstract

The invention relates to a synthetic method of tropisetron and a preparing method of hydrochloric acid tropisetron. The synthetic method of the tropisetron hydrochloride comprises enabling benzpyrole-3-formic acid and tropine to directly conduct esterification in atent solvent under effects of an aromatic organic sulfoacid compound catalytic agent. The tropisetron synthesized by using the method is then acidized, alkali adjusted, and refined to obtain the target product hydrochloric acid tropisetron. The synthetic method is simple in process, convenient to operate, small in pollution, high in product purity, ideal in yield, and applicable to large-scale industrialization production.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a synthesis method of tropisetron and a preparation method of tropisetron hydrochloride. Background technique [0002] Tropisetron hydrochloride (Tropisetron hydrochloride) chemical name is endo-1H-indole-3-carboxylic acid-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester hydrochloride, structural formula As shown in Formula 1 below: [0003] [0004] Tropisetron hydrochloride is a potent and highly selective competitive antagonist of peripheral neurons and central nervous system 5-hydroxytryptamine 3 (5-HT3) receptors, mainly by selectively blocking the presynaptic 5-HT3 receptors inhibit the gag reflex. It is indicated for the prevention and treatment of nausea and vomiting after cancer chemotherapy, radiotherapy and surgery in children and adults. [0005] Patent documents on the preparation method of tropisetron hydrochloride include (for example): US4797406, US 4789673, CN 10...

Claims

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Application Information

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IPC IPC(8): C07D451/12
Inventor 王威付彪
Owner NEW FOUNDER HLDG DEV LLC
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