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Novel diphenylethylene compound

A compound and composition technology, applied in the field of diphenylethylene compounds, can solve problems such as insulin receptor desensitization, unclear genetic factors, and defects in polysaccharide metabolism and decomposition

Inactive Publication Date: 2003-08-20
泽瑞克斯公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Insulin secretion and insulin resistance are considered major metabolic defects, but the exact genetic factors involved remain unclear
[0004] Subjects with diabetes typically have one or more of the following deficiencies: Insufficient production of insulin by the pancreas; Excessive secretion of glucose by the liver; Defects in glucose transporters; Desensitization of insulin receptors;

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Synthesis of E-3-(3,5-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-acrylic acid

[0060] To a mixture of 3,5-dimethoxybenzaldehyde (30 mmol) and p-hydroxyphenylacetic acid (30 mmol) was added 5 mL of acetic anhydride and 2.5 mL of triethylamine (TEA). After stirring at 130-140 °C for 24 h, the mixture was allowed to cool to room temperature and quenched with 25 mL of concentrated HCl and washed with CH 2 Cl 2 extraction. The organic extract was further extracted with 1N NaOH, and the NaOH extract was subsequently washed with CH 2 Cl 2 Washed, and the aqueous layer was acidified with conc. HCl and washed with water to give crude product. The crude product was recrystallized from ethanol / water to give acid Ia.

[0061] Four batches of Ia (E-isomer) 40 μl samples prepared above were separated by HPLC on an Intersil ODS-3 (GL Sciences) column, 250×4.6 mm, and 62 vol% eluent A and 38 vol % eluent B eluted. Eluent A is 0.1% formic acid in water; B is 0.1% formic acid in ACN....

Embodiment 2

[0075] Synthesis of 3-(3,4-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-acrylic acid

[0076] To a mixture of 3,4-dimethoxybenzaldehyde (9.97 g, 60 mmol) and p-hydroxyphenylacetic acid (10.0 g, 65 mmol) was added acetic anhydride (12 mL) and triethylamine (8.0 mL, 58 mmol) under argon atmosphere . The mixture was stirred at 140°C for 18 hours. The reaction mixture was cooled to 5 °C and dichloromethane (100 mL) was added. Concentrated HCl (20ml) was added to this yellow suspension and the suspension was stirred for 20 minutes. The solid that separated was filtered, dissolved in aqueous sodium hydroxide (2M, 225 mL) and reprecipitated with concentrated HCl (40 mL). The yellow solid was filtered and washed with water (2 x 30 mL), and the above wet solid was recrystallized from a water-ethanol mixture. 1 H NMR (DMSO-d 6 ): δ12.38 (br, 1H), 9.47 (br, 1H), 7.61 (s, 1H), 6.96 (d, J=8.4Hz, 2H), 6.81-6.77 (overlap, 4H), 6.54 (br, 1H), 3.40(s, 3H) and 3.37(s, 3H).

[0077] Synthesis o...

Embodiment 3

[0084] 60 mg streptozotocin by IV injection induced diabetes in Sprague-Dawley (SD) male rats (average body weight, 180 g). After 5 days, the average glucose concentration was about 350-400 mg / dL. Rats were then divided into 5 groups (n=7) and administered orally with phosphate buffered saline (PBS) (vehicle) or Compound Ia (10, 20, 40 or 80 mg / kg body weight) daily for 8 days. Treatment of Ia at doses of 20, 40 or 80 mg / kg reduced blood glucose concentrations in these rats from day 2 to day 6 (compared to those in vehicle-treated controls). This reduction was statistically significant (p<0.05) on days 4 and 6 in rats given 80 mg / kg. The result is shown in Figure 1.

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Abstract

Novel diphenylethylene compounds that are administered orally to decrease circulating concentrations of glucose are provided. The effect on insulin resistant rats is also shown. The effects on lipid and leptin concentrations are also shown. The compounds are orally effective anti-diabetic agents that may normalize glucose and lipid metabolism in subjects with diabetes.

Description

field of invention [0001] The field of the invention is novel diphenylethylene compounds and their use in the treatment of diabetes and related disorders. Background of the invention [0002] Pterocarpus marsupium Roxb. (Fabaceae) also known as the Indian Kino tree, whose leaves, flower extracts, and gums have been traditionally used for diarrhea, toothache, fever, and urinary and skin Infect. Extracts from its bark have long been known to be effective in treating diabetes. Manickam et al. (J.Nat.Prod.1997; 60:609-610) reported that the natural pterostilbene, trans-1-(3,5-dimethoxyphenyl) isolated from the heartwood of P. -2-(4-Hydroxyphenyl)-ethylene has some hypoglycemic activity. However, this pterostilbene is insoluble in water and has not been shown to be effective in the treatment of diabetes. [0003] The causes of type 1 and type 2 diabetes are still not understood, but both genetic and environmental factors appear to be involved. Type I di...

Claims

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Application Information

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IPC IPC(8): A61P3/10A61K31/192C07C43/23C07C59/64C07C59/68C07C233/54
CPCC07C233/54C07C43/23C07C59/64A61P3/10
Inventor P·尼奥吉B·纳格D·德伊S·麦迪彻拉
Owner 泽瑞克斯公司
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