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Preparation method of prostaglandin analogue midbody Corey aldehyde for treating glaucoma

A technology for prostaglandins and analogs, applied in the field of preparation of pharmaceutical intermediates, can solve the problems of not being able to store for a long time, inconvenient to use, complicated to handle, etc., and achieve the effects of low cost, convenient post-processing and good selectivity

Active Publication Date: 2013-12-18
ZHONGSHUAI PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing technical route for preparing Corey aldehyde, Dess-Martin oxidant is mostly used to complete this process. Dess-Martin oxidant has high cost, cannot be stored for a long time, must be prepared before use, and the post-treatment after oxidation is complicated. Disadvantages such as inconvenience and low yield

Method used

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  • Preparation method of prostaglandin analogue midbody Corey aldehyde for treating glaucoma
  • Preparation method of prostaglandin analogue midbody Corey aldehyde for treating glaucoma
  • Preparation method of prostaglandin analogue midbody Corey aldehyde for treating glaucoma

Examples

Experimental program
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Effect test

Embodiment 1

[0022] The present invention is used for the preparation method of the prostaglandin analog intermediate Corey aldehyde for the treatment of glaucoma, the detailed steps of this preparation method are as follows:

[0023] a, with dibenzoyl Corey lactone and 2-iodoylbenzoic acid as basic raw materials, the molar ratio between the two of said dibenzoyl Corey lactone and 2-iodoylbenzoic acid is 1:2, first Weigh 50.0g (142mmol) of dibenzoyl Corey lactone and 80.0g (284mmol) of 2-iodoylbenzoic acid according to the proportioning ratio and add them to a 1000mL reaction vessel, and add 520.0g of solvent ethyl acetate, which is combined with the The mass ratio between the benzoyl Corey lactone and the two is 10.4:1; connect the reflux condensation stirring device, heat the oil bath to 85°C for reflux reaction, reflux reaction for 8 hours, TLC board detects that there is no raw material remaining, stop heating and react Finished, after the reaction system was cooled to room temperature...

Embodiment 2

[0026] The present invention is used for the preparation method of the prostaglandin analog intermediate Corey aldehyde for the treatment of glaucoma, the detailed steps of this preparation method are as follows:

[0027] a, with benzoyl Corey lactone and 2-iodoylbenzoic acid as the basic raw material, the molar ratio between the benzoyl Corey lactone and 2-iodoylbenzoic acid is 1:2, first according to the formula Ratio Weigh 1.5kg (5.4mol) of benzoyl Corey lactone and 3.05kg (10.8mol) of 2-iodoylbenzoic acid into a 50 liter reactor, and add 27kg of solvent dichloromethane, the solvent and benzene The mass ratio of formyl Corey lactone between the two is 18:1; heat to 50°C for reflux reaction, reflux reaction for 18 hours, TLC plate detection no raw materials remaining, stop heating, the reaction is over, wait for the reaction system to cool to room temperature to proceed Filtrate to obtain the filtrate after filtration (the filter cake obtained after filtration is fully washe...

Embodiment 3

[0030] The present invention is used for the preparation method of the prostaglandin analog intermediate Corey aldehyde for the treatment of glaucoma, the detailed steps of this preparation method are as follows:

[0031] a. Taking tetrahydropyranyl Corey lactone and 2-iodoylbenzoic acid as basic raw materials, the molar ratio between the tetrahydropyranyl Corey lactone and 2-iodoylbenzoic acid is 1:1.5 100.0g (390mmol) of tetrahydropyranyl Corey lactone and 163.8g (585mmol) of 2-iodanoylbenzoic acid were weighed according to the proportioning ratio and added to a 3L reaction vessel, and 1500g of solvent toluene was added. The mass ratio of hydropyranyl Corey lactone between the two is 15:1, connect the reflux condensation stirring device, heat to 120°C for reflux reaction, reflux reaction for 12 hours, TLC plate detection no raw materials remaining, stop heating, the reaction is over , after the reaction system is cooled to room temperature and filtered, the filtrate is obtai...

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Abstract

The invention discloses a preparation method of prostaglandin analogue midbody Corey aldehyde for treating glaucoma. The preparation method comprises the following steps: by taking Corey lactones and 2-iodoxybenzoic acid as basic raw materials, adding the raw materials and a solvent to a reaction container in sequence, heating for a reflux reaction, and after reaction, and cooling to a room temperature for filtration; and sequentially filtering and drying obtained filtrate, after drying, filtering, and removing the solvent from the filtrate by adopting conventional reduced pressure distillation, thus obtaining the product Corey aldehyde. The preparation method is used for preparing the midbody Corey aldehyde and has the characteristics that the operation is simple, the cost is relatively low, an adopted oxidizing agent is mild in property, stable in air, easy to store and the like; the whole operation process is relatively simple and convenient, and the purity and the yield of product are high.

Description

1. Technical field: [0001] The invention relates to a preparation method of a drug intermediate, in particular to a preparation method of a prostaglandin analog intermediate Corey aldehyde used for treating glaucoma. 2. Background technology: [0002] Glaucoma is a common eye disease for which there is currently no cure. However, early diagnosis and treatment can prevent further deterioration and even blindness. Elevated intraocular pressure is considered one of the main risk factors for glaucoma and one of the few symptoms that can be alleviated by clinical intervention. Therefore, the treatment of glaucoma usually starts with lowering intraocular pressure to prevent optic nerve damage and maintain vision. Studies have found that topical application of prostaglandin (PG) and its analogs can promote the outflow of aqueous humor through the uveal sclera and reduce intraocular pressure. Among them, latanoprost, bimatoprost, travoprost and tafluprost have all been marketed a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/935
Inventor 孙卫东李锐
Owner ZHONGSHUAI PHARMA SCI & TECH CO LTD
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