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Preparation method of oxybutynin hydrochloride

A technology of oxybutynin hydrochloride and hydroxyphenylacetic acid, which is applied in the field of preparation of oxybutynin hydrochloride, can solve the problems of being unsuitable for industrial production, and the requirement of anhydrous reagents is extremely high, and achieves low cost, low price and stable quality. reliable results

Pending Publication Date: 2022-07-29
南京亿华药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The first step reaction of this process route uses the explosive precursor dangerous chemical potassium permanganate, and the second step uses the explosive precursor dangerous chemical magnesium chips, which are strictly regulated by the country for its purchase and use; and the second step It is a Grignard reaction with extremely high anhydrous requirements for reagents and is not suitable for industrial production

Method used

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  • Preparation method of oxybutynin hydrochloride
  • Preparation method of oxybutynin hydrochloride
  • Preparation method of oxybutynin hydrochloride

Examples

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Embodiment 1

[0032] (1) Synthesis of α-cyclohexyl-α-hydroxyphenylacetic acid propynyl ester (intermediate)

[0033] In a 1000ml three-necked flask, 117.15g (0.5mol) of cyclohexylmandelic acid, 650ml of ethyl acetate, 125g (0.9mol) of potassium carbonate, and 74.51g (1mol) of propyne chloride were sequentially added, and stirred at room temperature (25-35°C) for 25 hours , pour the reactant into 1300 g of cold water, stir for 10 minutes and stand to extract the organic layer, the aqueous layer is extracted once more with 325 ml of ethyl acetate, the organic layers are combined, washed once with water (650 ml), dried over anhydrous magnesium sulfate for 2 hours, filtered, The solvent was evaporated under reduced pressure to obtain a pale yellow oil: 118.3 g, yield: 86.8%.

[0034] (2) Synthesis of free form of oxybutynin

[0035] Add 118g (0.43mol) α-cyclohexyl-α-hydroxyphenylacetate propargyl (intermediate), 34.4g (0.47mol) diethylamine, 43ml 36% formaldehyde solution (0.56mol) to a 500ml ...

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Abstract

The invention discloses a preparation method of oxybutynin hydrochloride (the chemical name of the oxybutynin hydrochloride is alpha-cyclohexyl-alpha-hydroxy-phenylacetic acid-4-diethylamino-2-butyne ester hydrochloride). Comprising the following steps: carrying out esterification reaction on alpha-cyclohexyl-alpha-hydroxyphenylacetic acid and 3-propargyl chloride in the presence of a proper solvent and a basic catalyst to generate an intermediate, namely alpha-cyclohexyl-alpha-hydroxyphenylacetic acid propargyl ester, and then carrying out Mannich reaction on the alpha-cyclohexyl-alpha-hydroxyphenylacetic acid propargyl ester, a 36% formaldehyde solution and diethylamine to generate oxybutynin, and finally salifying with hydrochloric acid to generate oxybutynin hydrochloride. The method has simple reaction routes, does not involve reactions under harsh chemical reaction conditions, does not involve a high-risk chemical reaction process, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of oxybutynin hydrochloride, and belongs to the field of pharmaceutical synthesis. Background technique [0002] Oxybutynin hydrochloride (oxybutynin hydrochloride) is a third-generation drug for the treatment of urinary incontinence developed by the American Marion Pharmaceutical Company, with the trade name "Ditropan". Oxybutynin hydrochloride has the dual effects of direct antispasmodic and anticholinergic, can increase bladder capacity and volume of each urination, reduce involuntary bladder contraction, and prolong the interval between two urinations. It is clinically used to treat urgency, frequency and urination. incontinence. It has good oral effect and few side effects, and is a commonly used drug for patients with detrusor hyperreflexia. [0003] Regarding the synthesis of Oxybutynin hydrochloride, with different starting materials, there are mainly two synthetic routes reported in the literatur...

Claims

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Application Information

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IPC IPC(8): C07C225/18C07C221/00C07C49/252C07C45/45A61P13/00
CPCC07C221/00C07C45/455A61P13/00C07C2601/14C07C225/18C07C49/252
Inventor 杨鹏辉袁和亮周明健
Owner 南京亿华药业有限公司
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