Title:
METHOD FOR PREPARING NILUTAMIDE AND INTERMEDIATE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/174062
Kind Code:
A1
Abstract:
Disclosed is a method for preparing nilutamide and an intermediate thereof. The method comprises the following steps: at a temperature of 25 °C to 160 °C, using 4-nitro-3-trifluoromethylaniline represented by formula (I) and a compound represented by formula (II) with an amino protecting group PG as raw materials to conduct a condensation reaction and a ring-closing reaction to generate a compound represented by formula (III) and subjecting the compound represented by formula (III) to a direct ring closure without purification to generate nilutamide (formula IV); or subjecting the compound represented by formula (III) to a ring closure to prepare nilutamide. The present invention features short reaction steps, simple operation, high yield, and moderate reaction conditions, and uses cheap and readily available reagents, thus being suitable for both small-scale laboratory preparation and large-scale industrial production. Using the route described above, a new method for constructing a hydantoin ring is provided for the preparation of nilutamide, which is of great significance for the development of drugs comprising this structure.
Inventors:
MENG XIANGGUO (CN)
HU XIAMIN (CN)
SHAO LEI (CN)
WU KAI (CN)
LI CHENYE (CN)
WANG LUYI (CN)
YU SIJIE (CN)
WANG YIJING (CN)
CHANG RENJUN (CN)
SHI YUHAO (CN)
ZENG WANJING (CN)
YIN ZIXIN (CN)
SONG YINGWEI (CN)
LI LINWU (CN)
HU XIAMIN (CN)
SHAO LEI (CN)
WU KAI (CN)
LI CHENYE (CN)
WANG LUYI (CN)
YU SIJIE (CN)
WANG YIJING (CN)
CHANG RENJUN (CN)
SHI YUHAO (CN)
ZENG WANJING (CN)
YIN ZIXIN (CN)
SONG YINGWEI (CN)
LI LINWU (CN)
Application Number:
PCT/CN2023/079243
Publication Date:
September 21, 2023
Filing Date:
March 02, 2023
Export Citation:
Assignee:
SHANGHAI UNIV OF MEDICINE AND HEALTH SCIENCES (CN)
International Classes:
C07D233/72; C07C271/22
Foreign References:
| CN114605331A | 2022-06-10 | |||
| FR2540114A1 | 1984-08-03 | |||
| CN102753533A | 2012-10-24 | |||
| CN109651256A | 2019-04-19 | |||
| US4377522A | 1983-03-22 |
Other References:
LIU HUI, YANG ZHIMIN, PAN ZHENGYING: "Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf 2 O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 16, no. 22, 21 November 2014 (2014-11-21), US , pages 5902 - 5905, XP093091785, ISSN: 1523-7060, DOI: 10.1021/ol502900j
MAJI SAMIR KUMAR, HALDER D., VELMURUGAN D., RAJAKANNAN V., BANERJEE ARINDAM: "A unique example of a pseudo-peptide containing noncoded amino acids self-assembling into a supramolecular β-sheet-like structure in crystals", LETTERS IN PEPTIDE SCIENCE, ESCOM SCIENCE PUBLISHERS, NL, vol. 8, no. 2, 1 March 2001 (2001-03-01), NL , pages 61 - 67, XP093091786, ISSN: 0929-5666, DOI: 10.1007/BF02443606
MAJI SAMIR KUMAR, HALDER D., VELMURUGAN D., RAJAKANNAN V., BANERJEE ARINDAM: "A unique example of a pseudo-peptide containing noncoded amino acids self-assembling into a supramolecular β-sheet-like structure in crystals", LETTERS IN PEPTIDE SCIENCE, ESCOM SCIENCE PUBLISHERS, NL, vol. 8, no. 2, 1 March 2001 (2001-03-01), NL , pages 61 - 67, XP093091786, ISSN: 0929-5666, DOI: 10.1007/BF02443606
Attorney, Agent or Firm:
JEEKAI & PARTNERS (CN)
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