Separation and identification of an impurity from the istradefylline intermediate

Haojie Xu; Yiyun Wang; Hongyi Wang; Zhonghui Zheng; Zihui Meng; Min Xue; Zhibin Xu

doi:10.1039/c9ra09074f

Separation and identification of an impurity from the istradefylline intermediate

Haojie Xu, Yiyun Wang, Hongyi Wang, Zhonghui Zheng, Zihui Meng, Min Xue, Zhibin Xu

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Istradefylline is a selective adenosine antagonist for the A_2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A₁ (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A₁. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.

Original language	English
Pages (from-to)	14493-14499
Number of pages	7
Journal	RSC Advances
Volume	10
Issue number	25
DOIs	https://doi.org/10.1039/c9ra09074f
Publication status	Published - 8 Apr 2020

Access to Document

10.1039/c9ra09074f

Cite this

@article{e5035dbfb0a14699be16b1df931e0e13,

title = "Separation and identification of an impurity from the istradefylline intermediate",

abstract = "Istradefylline is a selective adenosine antagonist for the A2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A1 (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A1. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.",

author = "Haojie Xu and Yiyun Wang and Hongyi Wang and Zhonghui Zheng and Zihui Meng and Min Xue and Zhibin Xu",

note = "Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

month = apr,

day = "8",

doi = "10.1039/c9ra09074f",

language = "English",

volume = "10",

pages = "14493--14499",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "25",

}

TY - JOUR

T1 - Separation and identification of an impurity from the istradefylline intermediate

AU - Xu, Haojie

AU - Wang, Yiyun

AU - Wang, Hongyi

AU - Zheng, Zhonghui

AU - Meng, Zihui

AU - Xue, Min

AU - Xu, Zhibin

PY - 2020/4/8

Y1 - 2020/4/8

N2 - Istradefylline is a selective adenosine antagonist for the A2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A1 (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A1. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.

AB - Istradefylline is a selective adenosine antagonist for the A2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A1 (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A1. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.

UR - http://www.scopus.com/inward/record.url?scp=85083549846&partnerID=8YFLogxK

U2 - 10.1039/c9ra09074f

DO - 10.1039/c9ra09074f

M3 - Article

AN - SCOPUS:85083549846

SN - 2046-2069

VL - 10

SP - 14493

EP - 14499

JO - RSC Advances

JF - RSC Advances

IS - 25

ER -

Separation and identification of an impurity from the istradefylline intermediate

Abstract

Access to Document

Other files and links

Fingerprint

Cite this