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New method of synthesizing thalidomide and its derivative

A compound and mixture technology, applied in the field of preparing phthalamide piperidone and derivatives thereof, can solve the problems of difficult post-processing purification, long reaction steps, low yield and the like

Inactive Publication Date: 2005-03-23
TIANJIN HEMAY BIO TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, glutamic acid or glutamine with protected amino groups is used to prepare glutamic acid lactam, and the latter is reacted with phthalic anhydride or the corresponding Neaf reagent to obtain thalidomide derivatives. Usually this method reaction step is long, and overall yield is lower (Muller, G.W.et al, Bioorg.Med ChemLett., 1999,9,1625)
[0007] Recently, reports such as Seijas obtain a small amount of thalidomide (Seijas, J.A. et al Synthesis 2001 (7), 999) by the reaction of phthalic anhydride and glutamine at high temperature as by-products, however, the method yield Extremely low, post-processing purification is difficult, so the cost of industrial production is extremely high

Method used

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  • New method of synthesizing thalidomide and its derivative
  • New method of synthesizing thalidomide and its derivative
  • New method of synthesizing thalidomide and its derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 3-(1,3-Dihydroisoindol-1,3-dione-2-yl)piperidine-2,6-dione(phthalamidinone)phthalic anhydride (1.48 g, 10 mmole ) and glutamine (1.40 g, 9.5 mmole) in the mixture of water (5ml) and triethylamine (5ml), stirred at room temperature for 6 hours, and evaporated under reduced pressure to remove water and triethylamine to obtain (IIIA) (R 1 H, Z is a triethylamine salt of a benzene ring), the latter and carbonyldiimidazole (3.56 grams, 20 mmole) were refluxed in dry THF (15 ml) for 14 hours, cooled to room temperature and filtered, and the filter cake was washed with THF ( 10 mL) and dried in vacuo overnight to obtain 1.82 g of a white solid with a yield of 76%. M.p. 269°C-272°C. 1 H NMR (CDCl 3 , ppm) δ8.05 (br, 1H), 7.88-7.90 (m, 2H), 7.76-7.79 (m, 2H), 4.97-5.03 (m, 1H), 2.72-2.95 (m, 3H), 2.14- 2.20 (m, 2H).

Embodiment 2

[0032] 3-(1,3-Dihydroisoindol-1,3-dione-2-yl)piperidine-2,6-dione (phthalamidinone)

[0033] The reaction procedure is the same as that in Example 1. In the first step, dimethylformamide is used instead of water to obtain 1.26 g of white solid with a yield of 49%. M.p. 269°C-272°C.

Embodiment 3

[0035] 3-(1,3-Dihydroisoindol-1,3-dione-2-yl)piperidine-2,6-dione (phthalamidinone)

[0036] The reaction procedure was the same as that in Example 1. In the first step, dimethylformamide was used instead of THF to obtain 1.36 g of a white solid with a yield of 53%. M.p.268°C-270°C.

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Abstract

A process for synthesizing sedalis and its derivative is disclosed.

Description

technical field [0001] The invention relates to a new method for preparing thalidomide and its derivatives. technical background [0002] Thalidomide, because it inhibits the release of tumor necrosis factor, promotes and activates CD 8+ It has been used to treat skin lupus erythematosus (Arch.Dermatol, 1993, Vol.129.p.1548-1550) and refractory lupus erythematosus (The Journal of Rheumatology, 1989, 16, p923-92), Behcet's syndrome (Arch.Dermatol.1990, vol.126, p.923-927), Crohn's disease (Journal of pediatr.Gastroenerol. Nurt.1999, vol.28, p.214-216) and rheumatoid arthritis (Journal of Rheumatology, 1998, vol.25, p.964-969) have good curative effect, and can be used to treat various cancers , especially multiple myeloma. [0003] The most commonly used method for the preparation of thalidomide and its derivatives is to obtain phthalic amidoglutamic acid by reacting phthalic anhydride with glutamic acid, which then obtains internal acid anhydride under the action of a con...

Claims

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Application Information

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IPC IPC(8): C07D211/88C07D401/04C07D405/04C07D409/04
Inventor 张和胜
Owner TIANJIN HEMAY BIO TECH CO LTD
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