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Firocoxib preparation method

A technology for felocoxib and acetone, which is applied in the field of synthesizing filocoxib, can solve the problems of poor repeatability and low yield of key steps, and achieve the effects of simple post-processing process, low cost and high yield.

Inactive Publication Date: 2016-08-17
CHINA PHARM UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports on the synthesis of firocoxib, mainly including four documents: US6020343A, WO9716435A1, US5981576A, and CN104803956A, but the repeatability of the key steps is poor and the yield is not high

Method used

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  • Firocoxib preparation method

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Embodiment Construction

[0010] (1) Preparation of 2-methyl-1-(4-methylthiophenyl)-1-propanone

[0011] AlCl 3 (2.0g) was dissolved in chloroform (12mL), stirred and cooled to -10°C, wasobutyryl chloride (1.7mL) was added dropwise, stirred to dissolve, sulfide anisole (1.24g) was added dropwise, and the reaction was completed for about 1.5 hours. TLC monitoring, the reaction ended. It was quenched with water and the organic phase was separated. The organic phase was sequentially washed with saturated NaHCO 3 aqueous solution, saturated NaCl aqueous solution, anhydrous NaCl 2 SO 4 Dried, filtered, and spin-dried to obtain a colorless liquid, which was poured into a crystallization dish and evaporated to dry naturally to obtain a white solid with a yield of 99%. 1 H-NMR (500MHz, CDCl 3 )δ8.11(d, J=8.1Hz, 2H), 7.24(d, J=8.1, 2H), 3.49(m, 1H), 2.55(s, 3H), 1.18(d, 6H).

[0012] (2) Preparation of 2-methyl-1-(4-methylthiophenyl)-2-bromo-1-propanone

[0013] The product from the previous step (0.479...

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Abstract

The invention discloses a firocoxib preparation method and relates to the technical field of chemical synthesis, in particular to a novel method for synthesizing firocoxib. The novel method for synthesizing the firocoxib includes subjecting thioanisole serving as a raw material to acylation reaction, bromination reaction, oxidizing reaction, esterification reaction and cyclization reaction sequentially so as to obtain the firocoxib. Compared with a traditional technology, the novel method for synthesizing the firocoxib has the advantages that an aftertreatment process is simple without column chromatography separation, and the method is high in yield, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a new method for synthesizing firocoxib. Background technique [0002] Firocoxib is a veterinary non-steroidal anti-inflammatory drug, which produces antipyretic, analgesic and anti-inflammatory effects by selectively inhibiting the synthesis of prostaglandins mediated by cyclooxygenase-2 (COX-2). COX-2 is a subtype of cyclooxygenase that is mainly responsible for the synthesis of prostaglandins, which regulate pain, inflammation and fever. Selective inhibition of COX-2 can effectively relieve osteoarthritis pain. Approved by the FDA, firocoxib can currently be used to treat equine osteoarthritis and acute and chronic pain and inflammation caused by clinical operations. Different from other veterinary non-steroidal anti-inflammatory drugs, firocoxib can inhibit COX-2 with high selectivity, and is absorbed rapidly after oral administration. Therefore, it has very high practical ap...

Claims

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Application Information

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IPC IPC(8): C07D307/60
CPCC07D307/60
Inventor 戴振亚徐沛陈胜新余秋涵赵云德
Owner CHINA PHARM UNIV
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