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Novel preparation method of lenalidomide

A technology of lenalidomide and glutamine, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems of low total yield, long steps, and difficulty in industrialization, and achieve the effects of low production cost, short reaction steps, and no three wastes

Active Publication Date: 2013-07-10
HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In view of this, in order to solve the shortcomings of the existing lenalidomide preparation technology, such as long steps, low total yield, and difficulty in realizing industrialization, the present invention provides a new preparation method. The preparation process is simple, and the raw materials are cheap and easy to obtain. High efficiency, high safety, suitable for industrial production

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  • Novel preparation method of lenalidomide
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Examples

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Effect test

Embodiment 1

[0027] (1) Preparation of 3-N-Boc-aminopiperidine-2,6-dione

[0028] 41.6 g of N-Boc-L-glutamine was dissolved in 200 mL of 2-methyltetrahydrofuran, and 35.1 g of DCC was added in an ice bath at 0°C, and reacted at room temperature for 10 hours. Recover the solvent, extract three times with ethyl acetate, combine the organic layers, and successively wash with saturated NaHCO 3 , washed with saturated brine, dried over anhydrous sodium sulfate, and recovered the solvent to obtain 28.9 g of a white solid, with a yield of 75%. 1 H NMR (500 MHz, CDCl 3 ) δ: 8.17 (brs, 1H), 5.36 (brs, 1H), 4.33-4.30 (m, 1H), 2.82-2.77 (m, 1H), 2.72-2.64 (m, 1H), 2.54-2.51 (m, 1H), 1.91-1.82 (m, 1H), 1.46 (s, 9H)

Embodiment 2

[0030] 41.6 g of N-Boc-L-glutamine was dissolved in 200 mL of 2-methyltetrahydrofuran, and 35.1 g of DCC was added under ice-cooling at 0°C, and reacted at room temperature of 40°C for 10 hours. Recover the solvent, extract three times with ethyl acetate, combine the organic layers, and successively wash with saturated NaHCO 3 , washed with saturated brine, dried over anhydrous sodium sulfate, and recovered the solvent to obtain a white solid with a yield of 78%.

Embodiment 3

[0032] (2) Preparation of 3-aminopiperidine-2,6-dione hydrochloride

[0033] 10 g of 3-N-Boc-aminopiperidine-2,6-dione was dissolved in 30 mL of HCl-saturated ethyl acetate, stirred at room temperature for 8 hours, and filtered with suction to obtain 6.47 g of a white solid with a yield of 90%. 1 H NMR (500 MHz, DMSO-d 6 ): 11.26 (s, 1H), 8.74 (s, 3H), 4.21 (dd, J 1 =13.0Hz, J 2 = 5.0 Hz, 1H), 2.76-2.68 (m, 1H), 2.61-2.51 (m, 1H), 2.25-2.23 (m, 1H), 2.09-2.00 (m, 1H).

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Abstract

The invention discloses a method for preparing lenalidomide (3-(7-amino-3-oxo-1H-isoindazole-2-yl) piperidine-2,6-diketone). The method comprises the steps of: intramolecular cyclization, deprotection, phase-transfer catalytic reaction, catalytic hydrogenation, alkalization and the like. The technology is novel in path, short in step, high in reaction yield, and low in production cost, and has large implementation value and social and economic benefits.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis, in particular to a new preparation method of lenalidomide. Background technique [0002] Lenalidomide (3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione) is a new type of immune The modulator, which was approved by the US FDA in January 2006, with the trade name Revlimid, is mainly used clinically for the treatment of myelodysplastic syndrome (MDS) subtypes and multiple myeloma. [0003] Multiple myeloma (multiple myeloma, MM) is a refractory malignant B-cell disease, the patients' bone marrow malignant cells continue to proliferate so that normal cells cannot function. Myelodysplastic syndrome (MDS) is a clonal hematopoietic neoplasm that occurs when blood cells in the bone marrow, which fills with immature cells, are unable to perform their necessary functions , inhibiting the development of normal cells. [0004] Chemotherapy for MM and MDS began in the 1960s. In the f...

Claims

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Application Information

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IPC IPC(8): C07D401/04
Inventor 曾智丽盛荣竺彬赵丽英王美红
Owner HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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