Preparation and refining method of pomalidomide

A technology of polilidomide and its refining method, which is applied in the field of preparation and refining of polilidomide, can solve the problems of low yield, low purity of the final product, and complicated preparation and operation, and achieve high reaction yield and large implementation Value and socio-economic benefits, the effect of reasonable process conditions

A technology of polilidomide and its refining method, which is applied in the field of preparation and refining of polilidomide, can solve the problems of low yield, low purity of the final product, and complicated preparation and operation, and achieve high reaction yield and large implementation Value and socio-economic benefits, the effect of reasonable process conditions

CN103497174AActive Publication Date: 2014-01-08HANGZHOU PIOPHARM PHARMA TECH
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  • Preparation and refining method of pomalidomide
  • Preparation and refining method of pomalidomide
  • Preparation and refining method of pomalidomide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 3-Nitrophthalic anhydride (12.9g), α-aminoglutarimide hydrochloride (11.0g), acetonitrile (50ml), and acetic acid (10ml) were put into the reaction flask, heated and refluxed for 4 hours, Cool to room temperature, recover the solvent, add 50ml of water, precipitate a white solid, filter with suction, wash the solid with water, and dry under reduced pressure to obtain 16.7g, yield 83%, melting point > 200°C; 1 H NMR (DMSO- d6 ) δ: 11.17( s, 1H), 8.36 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz,1H), 8.10 (t, J = 7.5 Hz, 1H), 5.22 (dd, J = 13.0, 5.5 Hz, 1H ), 2.93-2.86 (m, 1H), 2.63-2.58 (m, 1H), 2.47-2.51 (m, 1H), 2.06-2.10 (m, 1H).

Embodiment 2

[0026] Put 3-nitrophthalic anhydride (12.9g), α-aminoglutarimide hydrochloride (11.0g), dioxane (50ml), and formic acid (20ml) into the reaction flask, heat up and reflux After 4 hours, cool to room temperature, recover the solvent, add 50ml of water, precipitate a white solid, filter with suction, wash the solid with water, and dry under reduced pressure to obtain 17.8g, yield 85%, melting point > 200°C;

Embodiment 3

[0028] Put 3-nitrophthalic anhydride (12.9g), α-aminoglutarimide hydrochloride (11.0g), toluene (60ml), p-toluenesulfonic acid (10g) into the reaction flask, and heat up to reflux After 8 hours, it was cooled to room temperature, the solvent was recovered, 150ml of water was added, a white solid was precipitated, filtered with suction, the solid was washed with water, and dried under reduced pressure to obtain 18.8g, yield 93.5%, melting point > 200°C.

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Abstract

The invention discloses a method for preparing pomalidomide [3-amino-N-(2,6-dioxo-3-piperidyl)-phthalimide], which comprises steps of condensation reaction, catalytic hydrogenation, refining, and the like. The process route is novel, short in steps, high in reaction yield, good in product purity, and has great implementation value and social economic benefits.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis, in particular to a method for preparing and refining polilidomide. Background technique [0002] Multiple myeloma (multiplemgeloma, MM) is a malignant B cell disease that is difficult to cure. The malignant cells in the bone marrow of patients continue to proliferate, causing normal cells to fail to function. It is caused by plasma cells in the bone marrow. It is a type of blood cancer. Affects middle-aged and elderly people. Pomalidomide is a new type of immunomodulator developed by Celgene Corporation of the United States. It was approved by the FDA in February 2013, and its trade name is Pomalyst. An immunomodulatory drug used to treat relapsed or refractory multiple myeloma, polilidomide destroys cancer cells by regulating the human immune system and inhibits the growth of cancer cells. [0003] The chemical name of polilidomide is 3-amino-N-(2,6-dioxo-3-piperidinyl)-phthali...

Claims

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Application Information

Patent Timeline
08 Jan 2014
Publication
CN103497174A
IPC
C07D401/04
CPC
C07D401/04
Inventors
陈波; 盛荣