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Preparation method of high-purity apremilast B crystal form

A high-purity, crystal-form technology, applied in the field of medicine, can solve problems such as low purity, and achieve the effects of safety, simplicity, strong operability, and easy industrial implementation

Inactive Publication Date: 2015-04-08
HANGZHOU XINBOSI BIOMEDICAL CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Solved the problem of low purity in the existing preparation method of Apremilast B crystal form

Method used

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  • Preparation method of high-purity apremilast B crystal form
  • Preparation method of high-purity apremilast B crystal form
  • Preparation method of high-purity apremilast B crystal form

Examples

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Embodiment 1

[0025] Add 2000 mL of acetic acid and 400.0 g of (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)-ethan-2-ylamine to a 10 L three-necked flask in sequence - N-acetyl-L-leucine salt and 220.6 g of 3-acetylaminophthalic anhydride, heated to reflux for 4 hours. Cool in a water bath and filter. After distilling off the solvent, add 4000mL of ethyl acetate, followed by 4000mL of water and 4000mL of saturated NaHCO 3 Solution wash. The organic phase was transferred to a 10 L three-necked flask, and 3500 mL of toluene was added dropwise. After the dropwise addition was completed, stir for 30 min and filter. The filter cake was air-dried in a drying oven at 80°C to obtain 391g of a light yellow solid, i.e. Apremilast C crystal form (the reflection angle 2θ of the X-ray powder diffraction pattern of the obtained crystal is at 7.5°, 11.3°, 16.4°, 17.8° , there is a characteristic peak at 26.4°, which is confirmed to be the crystal form of Apremilast C, see the attached figu...

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Abstract

The invention relates to a preparation method of an apremilast B crystal form, and particularly relates to a preparation method of a high-purity apremilast B crystal form. The preparation method specifically comprises the following steps: (a) preparing an apremilast C crystal form; and (b) converting the C crystal form into a B crystal form. The HPLC purity of the apremilast B crystal form prepared by using the preparation method is greater than 99.9%, the maximum individual impurity is less than 0.1%, and the chiral purity is greater than 99.8%; and the preparation method is safe, simple, and strong in operability.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of Apremilast B crystal form. Background technique [0002] Apremilast, chemical name S-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-4-acetylaminoisoind Indoline-1,3-dione, its chemical structure is: [0003] [0004] Apremilast was approved by the US FDA on March 25, 2014, with a trade name of Otezla for the treatment of psoriatic arthritis. Apremilast is the first new type of phosphodiesterase (PDE4) inhibitor-type oral drug approved for marketing, manufactured by Celgene in Summit, New Jersey. It has good efficacy and high safety, and has changed the global psoriasis Current status of the treatment of arthritis. [0005] Apremilast has multiple crystal forms. Chinese patent CN102046167A has reported 7 crystal forms of Apremilast A, B, C, D, E, F and G, among which the B crystal form of Apremilast is relatively stable and is also The only...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 杜焕达何永富丁建圣王万青刘艳华
Owner HANGZHOU XINBOSI BIOMEDICAL CO LTD
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