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Novel bioactive diphenyl ethene compounds and their therapeutic applications

A compound, alkenyl technology, used in the field of pharmaceutical compositions for treating diseases and immunomodulators

Active Publication Date: 2005-10-26
BEIJING WEN FENG TIANJI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, we have recently discovered that, in addition to this unique substitution pattern on one benzene ring, some special substituents on the other benzene ring, such as fluorine atom, can lead to surprising immunomodulatory activity of the compound

Method used

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  • Novel bioactive diphenyl ethene compounds and their therapeutic applications
  • Novel bioactive diphenyl ethene compounds and their therapeutic applications
  • Novel bioactive diphenyl ethene compounds and their therapeutic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0047] Example 1.4-[2-(3,5-dimethoxy-4-isopropylphenyl)vinyl]benzoic acid (1)

[0048] a). Methyl 3,5-dimethoxy-4-isopropylbenzoate

[0049] This compound was synthesized by the method of patent WO 01 / 42231. 1 HNMR (CDCl 3 , ppm): δ1.32(d, J=7.2Hz, 6H), 3.66(hept, J=7.2Hz, 1H), 3.82(s, 6H), 3.95(s, 3H), 7.25(s, 2H) .

[0050] b).3,5-dimethoxy-4-isopropyl benzyl alcohol

[0051] Suspend 5 g of LiAlH in 100 mL of dry diethyl ether 4 (95%, 125 mmol), under the protection of nitrogen, at 0 ℃, add dropwise 3,5-dimethoxy-4-isopropyl benzoic acid methyl ester (15.7 g, 90.1 mmol) in ether (300 mL) solution, the suspension after the dropwise addition was stirred at 0° C. for one hour, and then at room temperature for another hour. Slowly add about 10 ml of saturated Na to the reaction flask at 0°C 2 SO 4 Aqueous solution, the mixed system continued to stir overnight, the solid matter was filtered off, and the filtrate was evaporated to dryness to obtain 13.8 g of the desired pr...

Embodiment 23

[0058] Example 2.3-[2-(3,5-dimethoxy-4-isopropylphenyl)vinyl]benzoic acid (2)

[0059] This compound was synthesized from 3,5-dimethoxy-4-isopropylphenyl)ethene and 3-bromobenzoic acid by the same synthesis method as compound (1), and the yield was 77%. 1 HNMR (CDCl 3 , ppm): δ1.32(d, J=7.1Hz, 6H), 3.63(qint, J=7.1Hz, 1H), 3.90(s, 6H), 6.76(s, 6H), 7.08(d, J= 17Hz, 1H), 7.25(d, J=17Hz, 1H), 7.50(t, J=7.7Hz, 1H), 7.79(d, J=7.7Hz, 1H), 8.04(d, J=7.7Hz, 1H ), 8.31(s, 1H).

Embodiment 34

[0060] Example 3.4-[2-(3,5-dihydroxy-4-isopropylphenyl)vinyl]benzoic acid (6)

[0061]4-[2-(3,5-dimethoxy-4-isopropylphenyl)vinyl]benzoic acid (0.289 g, 0.886 mmol) and pyridine hydrochloride (0.67 g, 5.9 mmol) The mixture was heated at 200°C for 2 hours under argon flow. After the reaction mixture was lowered to room temperature, 10 ml of 2N hydrochloric acid and 50 ml of ether were added, and the organic phase and the aqueous phase were separated, and the aqueous phase was extracted twice with 50 ml of ether, and the extracts were combined, washed with saturated brine, washed with sodium sulfate dry. After the diethyl ether was distilled off, the residue was separated and purified by column chromatography, and the eluent was ethyl acetate / hexane / acetic acid (40 / 60 / 1) to obtain 4-[2-(3,5-dihydroxy-4-isopropyl phenyl) vinyl] benzoic acid (6) 0.03 g, yield 11%. 1 HNMR (DMSO-d 6 , ppm): δ1.22(d, J=7.0Hz), 6.49(s, 2H), 6.90(d, J=18Hz, 1H), 7.19(d, J=18Hz, 1H), 7.67(d, J =8Hz...

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PUM

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Abstract

The present invention provides a group of new stilbene derivatives and pharmacologically acceptable salts thereof, a method for preparing the compound, a pharmaceutical composition thereof and the compound as a therapeutic agent for immune diseases, inflammation and autoimmunity. Application in immune disease reagents.

Description

Background of the invention [0001] Stilbene compounds are well-known compounds with various activities, which are widely distributed in nature. In recent years, the natural and synthetic derivatives of stilbene have attracted more and more people's interest because of their physiological activities. For example, the stilbene derivative 3,5,4'-trihydroxystilbene is known as resveratrol, and its cis-trans isomers have been reported to have a series of physiological activities, including anti-inflammatory treatment and cancer chemoprevention (Jang, et al. 1997, Science, 275, 218, US 6,008, 260). [0002] It is clear that in the basic structure of stilbene, substitution at two benzene rings leads to a large number of derivatives, for example in the case of one or two substituents on one or both benzene rings (Shudo K ., 1988, US4723028; Hensley, K.L., et al., WO99 / 59561, Kunihiro N., 1983, JP58159410; genji I., 1995, JP07053359 and GB1465661). There are also derivatives with th...

Claims

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Application Information

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IPC IPC(8): A61K31/05A61K31/085A61K31/11A61K31/19C07C39/21C07C39/215C07C39/27C07C39/373C07C43/215C07C43/225C07C43/23C07C45/00C07C47/575C07C65/19C07C65/28
CPCC07C65/19C07C43/215C07C47/575C07C39/21C07C43/225C07C45/00C07C43/23C07C39/373C07C65/28A61P1/04A61P9/10A61P17/02A61P17/06A61P17/14A61P19/02A61P25/00A61P29/00A61P35/00A61P37/02A61P37/08C07C39/215
Inventor 陈庚辉李建雄刘卫约翰·韦伯斯特
Owner BEIJING WEN FENG TIANJI PHARMA CO LTD
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