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Title:
SYNTHESIS METHODS OF FIROCOXIB AND INTERMEDIATE THEREOF
Document Type and Number:
WIPO Patent Application WO/2019/062561
Kind Code:
A1
Abstract:
Provided herein the synthesis methods of firocoxib and an intermediate thereof. The synthesis of the first intermediate is performed through methylation of p-bromopropiophenone or through Friedel-Crafts acylation of bromobenzene, avoiding the use of environmental unfriendly thioethers as starting materials. The second intermediate is directly obtained by sulfonation of the first intermediate, wherein the sulfidation reaction and the oxidization reaction are shortened to one-step reaction. The sulfonation step greatly simplifies the reaction steps, shortens the reaction time, and improves the reaction efficiency. Meanwhile, an N-bromosuccinimide(NBS) catalyst system is also adopted in the hydroxylation of the second intermediate to directly obtain the firocoxib intermediate. Such an environmental friendly method is suitable for large-scale production, and the reaction rate is increased. In addition, the firocoxib synthesis method comprises the synthesis method of the firocoxib intermediate and can prepare firocoxib in a milder and more environmentally friendly manner.

Inventors:
WANG, Ying (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
LI, Xiaoxun (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
LIU, Shikui (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
LU, Tiegang (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
DENG, Xianhua (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
Application Number:
CN2018/105661
Publication Date:
April 04, 2019
Filing Date:
September 14, 2018
Export Citation:
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Assignee:
SICHUAN QINGMU PHARMACEUTICAL CO., LTD. (No. 55, South Shunjiang AvenueEast Economic Development Zon, Meishan Sichuan 0, 612100, CN)
International Classes:
C07C49/233; C07C45/46; C07C45/68; C07C315/04; C07C317/24; C07D307/60
Foreign References:
CN107686471A2018-02-13
CN107345140A2017-11-14
CN104803956A2015-07-29
CN107778204A2018-03-09
Other References:
XU QUAN ET AL.: "C-C Coupling of ketones with Methanol Catalyzed by a N-Heterocyclic Carbene-Phosphine Iridium Complex", CHEM. EUR. J., vol. 21, no. 9, 14 January 2015 (2015-01-14), pages 3576 - 3579, XP055587734, ISSN: 0947-6539
Attorney, Agent or Firm:
BEIJING SUNHOPE INTELLECTUAL PROPERTY LTD. (Suite 1106, Kunxun PlazaZhichun Road 9, Haidian District, Beijing 1, 100191, CN)
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