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Process for preparation of isotretinoin

A technology of isotretinoin and retinoic acid, which is applied in the direction of carboxylate preparation, organic compound preparation, chemical instruments and methods, etc., and can solve problems such as high energy costs

Inactive Publication Date: 2002-09-25
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is limited by the need for two different bases (sodium hydride and lithium diisopropylamide), and in addition, the production of dienolates requires prolonged low temperature (-78°C), which is not feasible on a commercial scale. will require very high energy costs

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A solution of n-butyllithium in hexane (321ml, 15%) was added to a solution of diisopropylamine (48.6g, 0.48mol) in tetrahydrofuran (1000ml) at -30°C under nitrogen atmosphere, The resulting mixture was stirred for 1 hour. The reaction mixture was then cooled to -72°C and methyl 3,3-dimethacrylate (55 g, 0.48 mol) was added. Stirring was continued at -65°C to -75°C for 30 minutes. A solution of β-pinylidene acetaldehyde (100 g, 0.458 mol, 9-trans isomer content: 80%) was added to the resulting mixture, and the reaction mixture was stirred at -65°C to -75°C for 1 hour. The reaction mixture was then warmed to 40°C and stirred at this temperature for 3 hours. The solvent was removed in vacuo and the reaction mixture was diluted with water (700ml) and methanol (300ml). Activated carbon (4 g) was then added and the mixture was refluxed for 30 minutes. The heterogeneous mixture was filtered on hyflo and the hyflo bed was washed with methanol (300ml) and water (150ml). Th...

Embodiment 2

[0019] In a nitrogen atmosphere, a solution of n-butyllithium in hexane (20ml, 15%) was added to diisopropylamine (2.7g, 0.027mol) in diisopropyl ether (10ml) at -74°C solution, the resulting reaction mixture was stirred for 0.5 hours. Methyl 3,3-dimethacrylate (2.51 g, 0.022 mol) was added to this mixture at -74°C. Stirring was continued at -70°C ± 2°C for 30 minutes, and then the mixture was added to β-geranylidene acetaldehyde (5 g, 0.022 moles, 9-trans isomer content: 80%) at -74°C diiso Propyl ether (20ml) solution. The resulting mixture was stirred at -72°C ± 2°C for 1 hour, then slowly warmed to room temperature. The reaction mixture was stirred overnight at ambient temperature and worked up as in Example 1 to obtain 1.03 g of pure isotretinoin.

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PUM

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Abstract

The invention relates to a single-step method for preparing the 13-cis isomer of retinoic acid (commonly known as isotretinoin).

Description

technical field [0001] The invention relates to a method for single-step preparation of the 13-cis isomer of tretinoin, commonly known as isotretinoin. Background technique [0002] Isotretinoin (13-cis retinoic acid) belongs to the family of vitamin A (retinol) related compounds. It inhibits the function and keratinization of the sebaceous glands and is used in the treatment of skin disorders such as acne. It is very effective against very severe and nodulocytic acne and prevents the formation of scars. Recently, isotretinoin has also been evaluated for its potential use in certain cancerous conditions. [0003] Structurally, isotretinoin is a highly conjugated molecule consisting of a substituted cyclohexene moiety and a 9-carbon polyene side chain with a terminal carboxyl group. Of all the double bonds in the side chain, only one double bond (C-13 double bond) is trans, and this double bond is the stereospecific structure of the polyene side ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/353C07C403/20C07D309/32
CPCC07C51/353C07C403/20C07D309/32C07C2601/16C07C57/26
Inventor M·萨勒曼V·K·考尔J·S·巴比N·库马尔
Owner RANBAXY LAB LTD
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