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Sulfur pentafluoride substituted benzopyrans and their applications

A technology of sulfur pentafluoride and benzopyran, which is applied in the field of sulfur pentafluoride substituted benzopyran compounds, can solve the problems of withdrawal, cardiovascular risk, and no alternative drugs are found, and achieve the possibility of reducing hypertension Sex, reduce allodynia, inflammation and pain excellent effect

Active Publication Date: 2018-09-14
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But they also have shortcomings, such as rofecoxib was determined to cause cardiovascular risk and was withdrawn globally
Although there are "bad boys" with serious adverse reactions in the COX-2 family, they still play a huge role in relieving the patient's condition, and no better alternative drugs have been found so far

Method used

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  • Sulfur pentafluoride substituted benzopyrans and their applications
  • Sulfur pentafluoride substituted benzopyrans and their applications
  • Sulfur pentafluoride substituted benzopyrans and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Preparation of 6-sulfur-pentafluoride-2-trifluoromethyl-2H-benzopyran-3-carboxylic acid.

[0102]

[0103] Prepare according to the above reaction scheme, comprising the following steps:

[0104] 1. Synthesis of Compound 2

[0105] Dissolve compound 1 (1g, 4.5mmol) in trifluoroacetic acid (20mL), then slowly add hexamethylenetetramine (0.88g, 6.3mmol) to the solution, keep the temperature at 80°C for 4h, stop heating and cool to At room temperature, 10 mL of water was added and stirred for 0.5 h. After the reaction was completed, saturated sodium bicarbonate solution was added, extracted with ethyl acetate, and the extracted organic phase was washed with brine, dried, rotary evaporated under reduced pressure, and compound 2 (0.6 g, yield 52%) was obtained by column chromatography.

[0106] The characterization data of this compound 2 are:

[0107] 1H NMR (400MHz, d-CDCl3), d11.32 (s, 1H), 9.95 (s, 1H), 8.011 (s, 1H), 7.93-7.90 (d, 1H), 6.88-6.86 (d, 1H).

[0108]...

Embodiment 2

[0117] (S) Preparation of 6-sulfur-pentafluoride-8-bromo-2-trifluoromethyl-2H-chromene-3-carboxylic acid.

[0118]

[0119] Prepare according to the above reaction scheme, comprising the following steps:

[0120] 1. Synthesis of Compound 5

[0121] Compound 1 (2g, 9.2mmol) and anhydrous potassium carbonate (3.8g, 27.6mmol) were added to DMF (30ml), and methyl iodide (1.32g, 9.2mmol) was added dropwise under ice cooling, and stirred overnight at room temperature. After the reaction, water was added and extracted with ethyl acetate. The extracted organic phase was washed with saturated brine, dried, and rotary evaporated under reduced pressure. Compound 5 (1 g, yield 93%) was obtained by column chromatography.

[0122] The characterization data of this compound 5 are:

[0123] 1H NMR (400MHz, d-CDCl3), d7.72-7.69 (d, 2H), 6.94-6.92 (d, 2H), 3.3.87 (s, 3H).

[0124] 2. Synthesis of Compound 6

[0125] Compound 5 (2g, 8.56mmol) was dissolved in acetic acid (30ml), and liqui...

Embodiment 3

[0149] (R) Preparation of 6-sulfurpentafluoride-2-trifluoromethyl-2H-chromene-3-carboxylic acid.

[0150]

[0151] According to the above reaction scheme, the above compound 12 was prepared with reference to the method of Example 2. Wherein, the catalyst used in the synthesis of compound 11 is (2R)-2-[diphenyl[(trimethylsilyl)oxy]methyl]-pyrrolidine.

[0152] The characterization data of this product (R) 6-sulfur pentafluoride-2-trifluoromethyl-2H-chromene-3-carboxylic acid is:

[0153] 1HNMR(400MHz,d-CDCl3),d7.85(s,1H),7.77-7.75(d,1H),7.70(s,1H),7.10-7.08(d,1H),5.80-5.78(d,1H ).

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Abstract

The invention discloses a sulfur pentafluoride-substituted benzopyran compound shown in the structural formula I or its pharmaceutically acceptable salt or stereoisomer or prodrug molecule. The sulfur pentafluoride-substituted benzopyran compound has effects of selectively inhibiting COX-2 enzyme and inhibiting inflammation. The compound or its pharmaceutically acceptable salt or stereoisomer or prodrug molecule can be used for preparation of drugs for diminishing inflammation, relieving pain and preventing or treating tumors.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a sulfur pentafluoride substituted benzopyran compound and its application. Background technique [0002] Inflammation is a common and frequently occurring disease that endangers human health and affects the quality of human life. The most common disease is arthritis, and there are currently about 355 million arthritis patients in the world. The number of arthritis patients in my country is estimated to be about 100 million and is increasing every year. Therefore, the research and development of anti-inflammatory analgesic drugs is of great significance. [0003] Traditional non-steroidal anti-inflammatory drugs, including ibuprofen and diclofenac, are the main drugs for the treatment of arthritis. However, while these drugs play an analgesic and anti-inflammatory role, they also bring a variety of serious gastrointestinal adverse reactions and complications, such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58A61K31/352A61P29/00A61P35/00A61P19/02A61P19/08A61P37/02A61P17/06A61P17/00A61P1/00A61P1/04A61P25/06A61P25/04A61P7/06A61P21/00A61P27/02A61P31/12A61P11/00A61P25/28A61P11/02A61P1/16A61P9/10A61P7/02A61P31/04A61P35/02
CPCC07D311/58
Inventor 张艳梅约翰·J·泰勒米琦·托特雷拉涂正超刘小蓉王贻灿刘健齐温鼎生陆鑫陆永志
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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