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Novel preparation method of lenalidomide

A technology of lenalidomide and reflux temperature, which is applied in the field of new preparation of chemical drugs, can solve the problems of high industrialization cost, environmental pollution, and long route, and achieve the effects of low production cost, environmental friendliness, and high total reaction yield

Inactive Publication Date: 2014-02-26
湖南华腾制药有限公司
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Problems solved by technology

This process has the disadvantages of long route, low yield, serious environmental pollution and high industrialization cost

Method used

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  • Novel preparation method of lenalidomide

Examples

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Embodiment 1

[0029] (1) Preparation of 3-bromo-2,6-piperidinedione

[0030] Add 10.2 g of glutarimide to 20 ml of acetic acid, add 4.5 ml of bromine, heat to reflux, stir for 3 hours, cool to room temperature, remove excess acetic acid and bromine under reduced pressure, and add the residue to chloroform and Extracted in water, the organic phase was dried, concentrated, and recrystallized from ethanol to obtain 17.1 g of white solid compound 3 (yield 99%), 1H-NMR (CDCl3, 400MHz) δ: 8.34 (s, 1H), 4.64 (t, 1H ),2.91-3.00(m,1H),2.66-2.73(m,1H),2.28-2.47(m,2H).

[0031] (2) 3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

[0032] 8.9g 4-nitro-isoindoline-1-one and 9.5g compound 3 were added to 150ml N,N'-dimethylformamide, and then 13.8g K 2 CO 3 , stirred and heated to reflux, reacted for 8 hours, stopped heating, cooled to room temperature, added 1000ml of water, stirred thoroughly, then added 300ml of ethyl acetate, extracted and separated, collected the organic phase,...

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Abstract

The invention discloses a novel preparation method of lenalidomide. Glutarimide and 4-nitro-isoindolin-1-one are used as raw materials of the lenalidomide. The lenalidomide is prepared by (1) performing bromination in the alpha position of the carbonyl of the glutarimide to obtain 3; (2) condensing 4-nitro-isoindolin-1-one and the 3 to obtain 4; and (3) subjecting the 4 to reduction to obtain 5, namely the lenalidomide. The preparation method has easily available raw materials, short steps, simple operation, high reaction yield and low production cost, and is environmental friendly. The preparation method has large implement value and social and economic benefit.

Description

technical field [0001] The invention relates to a novel preparation method of a chemical drug, in particular to a novel preparation method of the compound lenalidomide. technical background [0002] Lenalidomide (Lenalidomide), brand name REVLIMID TM , chemical name 3-(7-amino-3-oxo-1h-isoin-dol-2-yl) piperidine-2,6-dione, CAS: 191732-72-6, structural formula: [0003] [0004] Lenalidomide is a new immunomodulatory oral preparation developed by Celgene Corporation of the United States, which is used to treat fatal blood diseases and cancer drugs. Lenalidomide has effects on multiple biological pathways in cells. Celgene is still evaluating the hematology and oncology treatment of this product, including multiple myeloma, myelodysplastic syndrome, chronic lymphocytic leukemia and solid tumors. Myelodysplastic syndrome is a hematologic malignancy affecting approximately 300,000 patients worldwide. MDS occurs when blood cells in the bone marrow remain immature and canno...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 邓泽平陈芳军蒋江平
Owner 湖南华腾制药有限公司
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