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Optical isomer of phencynonate and its use in preparing medicine

A technology of phencyclonyl ester and medicine, which is applied in the field of phencyclonyl ester optical isomers and their use for preparing medicines, and can solve problems such as physical and chemical properties of phencyclyl nonyl ester isomers that are not related to optical purity.

Active Publication Date: 2008-11-19
BEIJING AOHE DRUG RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these reports did not refer to a single optically pure phencyclononate isomer or any of its physicochemical properties

Method used

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  • Optical isomer of phencynonate and its use in preparing medicine
  • Optical isomer of phencynonate and its use in preparing medicine
  • Optical isomer of phencynonate and its use in preparing medicine

Examples

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preparation example 1

[0033] Preparation example 1. Preparation of ethyl cyclopentylglyoxylate (II)

[0034] Place dried 117g (0.80mol) diethyl oxalate and 120ml anhydrous ether in a 1L three-necked flask, cool in an ice bath, protect with dry nitrogen, and add dropwise 350ml of newly prepared cyclopentylmagnesium bromide Grignard reagent ( 0.40mol) of anhydrous ether solution, the reaction temperature does not exceed 0°C, and the drop is completed within about 2.5 hours. Stir at room temperature for 2 hours, add 120 mL of aqueous solution containing 21 g of ammonium chloride dropwise to the reaction mixture under cooling, stir at room temperature for 20 minutes, separate the ether layer, wash with water, dry over anhydrous magnesium sulfate, filter, recover the solvent, and distill the residue under reduced pressure , and collected fractions at 122-124° C. / 15 mmHg to obtain 37.3 g of the title compound (II) as a colorless oil, with a yield of 53%. Mass Spectrum m / z: 170(M + ).

preparation example 2

[0035] Preparation Example 2. Preparation of α-phenyl-α-cyclopentyl-α-hydroxyacetic acid ethyl ester (III) and α-phenyl-α-cyclopentyl-α-glycolic acid (IV)

[0036] Put 41g (0.24mol) of ethyl cyclopentylglyoxylate (II) and 350ml of anhydrous ether in a 1L flask, cool in an ice bath, protect with dry nitrogen, and add 300ml of newly prepared phenylmagnesium bromide Grignard dropwise. Reagent (0.27mol) in anhydrous ether solution, the reaction temperature does not exceed 0°C, and the drop is completed within about 2 hours. Stir at room temperature for 1 hour, add dropwise 100 mL of an aqueous solution containing 20 g of ammonium chloride to the reaction mixture under cooling, stir at room temperature for 20 minutes, separate the ether layer, wash with water, dry over anhydrous magnesium sulfate, filter, recover the solvent, and distill the residue under reduced pressure , and collected 94-96°C / 20μmHg fractions to obtain the yellow oily title compound (III), which was mixed with 400...

preparation example 3

[0037] Preparation Example 3. Preparation of (+)-α-phenyl-α-cyclopentyl-α-glycolic acid (V)

[0038] 22g (0.10mol) of the racemized α-phenyl-α-cyclopentyl-α-hydroxyacetic acid obtained in Preparation Example 2 was dissolved in 120mL of ethyl acetate, heated to boiling, and 14g (0.104mol) (+ )-1-methyl-2-phenylethylamine in ethyl acetate (50 mL). After the dropwise addition, the reaction solution was cooled to room temperature and left overnight. Filtration collected 25 g of (+)-α-phenyl-α-cyclopentyl-α-glycolic acid (+)-1-methyl-2-phenylethylamine salt. The resulting salt was recrystallized from ethanol (10 mL / g) until the optical rotation was stable, yielding 8.7 g of the salt. The resulting salt was suspended in 50 mL of water, treated with 6N sodium hydroxide solution, and washed three times with ether. The aqueous layer was acidified with 6N hydrochloric acid, cooled and crystallized to obtain 5.3 g of (+)-α-phenyl-α-cyclopentyl-α-glycolic acid (V), with a recovery rate...

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Abstract

The present invention relates to the optically pure isomer of phencynonate, levorotary phencynonate isomer, or its pharmaceutically acceptable salt, its preparation process and the medicinal use in preparing medicine for car sickness, sea sickness and other motion sickness, Meniere's syndrome and other kinds one dizziness. The said levorotary phencynonate isomer and its pharmaceutically acceptable salt may be also used in treating or remitting Parkinson's disease or Parkinson's syndrome with less side effect than phencynonate.

Description

Technical field: [0001] The invention relates to an optically pure isomer of levophencyclononate and a pharmaceutically acceptable salt thereof, a preparation method thereof and an application thereof for preparing medicines for preventing and / or treating diseases such as vertigo. Background technique [0002] Formula (I) phencyclononyl hydrochloride (systematically named as 2'-cyclopentyl-2'-phenyl-2'-hydroxyacetic acid-9α-[3-methyl-3-azabicyclo (3.3.1) Nonyl ester hydrochloride) is a selective anticholinergic drug, which is clinically used to prevent and treat various motion sicknesses such as motion sickness and seasickness. CN1089838A and US6028198 disclose the use of phencyclonyl hydrochloride as an anti-motion sickness (motion sickness, boat, machine, etc.) drug; CN97125424.9, GB2297255 and ES549796A disclose the preparation method of phencyclonyl hydrochloride. WO02067933 discloses the use of phencyclonyl hydrochloride for treating Parkinson's disease / syndrome and it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/22A61K31/216A61P25/16A61P1/08A61P9/02C07C69/732
CPCY02P20/582
Inventor 仲伯华郑建全刘河刘克良谢剑炜刘利平李万华陈兰福刘卫王亚平盖晓丹翁谢川
Owner BEIJING AOHE DRUG RES INST
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