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Heterocyclic analog of diphenylethlene compound and application thereof

A compound, alkenyl technology, applied in the field of new compounds, can solve the problems of hypoglycemia, limited curative effect, inability to prevent and treat complications, etc.

Inactive Publication Date: 2010-02-03
SHENZHEN NEPTUNUS PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently clinically used diabetes treatment drugs have shortcomings such as limited curative effect, hypoglycemia, and inability to prevent and treat its complications.

Method used

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  • Heterocyclic analog of diphenylethlene compound and application thereof
  • Heterocyclic analog of diphenylethlene compound and application thereof
  • Heterocyclic analog of diphenylethlene compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0199] General method: Melting point was measured on RT-1 melting point apparatus (Tianjin Analytical Instrument Factory), and the temperature was corrected. Recorded in Bruker AV400(400MHz) spectrometer 1 HNMR spectra and are illustrated in parts per million (ppm) downfield of TMS. Infrared spectra were recorded on a Nicolet Magna 550 FT-IR Fourier Spectrophotometer. Mass spectra were recorded with an HP1100 Esquire2000 liquid chromatography / mass spectrometer. UV spectra were recorded on a Shimadzu UV2410 UV spectrophotometer. TLC was carried out on a silica gel GF254 high-efficiency plate (Yantai Zhifu Silica Gel Development and Experimental Factory). The polarimetry was performed on a WZZ-1S polarimeter (Shanghai Precision Scientific Instrument Co., Ltd.).

[0200] 3-(3,5-Dimethoxyphenyl)-2-(3-hydroxyphenyl)-acrylic acid (7). Acetic anhydride (20 mL, 0.212 mol) and Triethylamine (8.4 mL, 0.06 mol). After stirring at 130-140° C. for 6 h, the mixture was cooled to room...

Embodiment 2

[0239]3-(3,5-Dimethoxyphenyl)-2-{3-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}- Acrylamide(24)

[0240] Compound 24 can be represented by the following structural formula:

[0241]

[0242] The following describes the preparation of compound 24 from compound 14. To a clean dry flask with a stir bar was added compound 14 (2.12 g, 4.18 mmol) and dry DMF (50 mL). Carbonyldiimidazole (1.36 g, 8.35 mmol) was then added with stirring and the reaction was heated to 60 °C for 1 h while venting through an oil bubbler. The reaction mixture was then cooled to 0 °C and 2M ammonia in methanol (10.5 mL, 21 mmol) was added. The reaction was worked up by partitioning the mixture with 10% citric acid (50 mL), ethyl acetate (250 mL), and water (200 mL). Then the organic phase was washed sequentially with water (2×150 mL), brine (1×150 mL) and washed with anhydrous MgSO 4 dry. Concentration of the organics provided crude product. The crude product was purified by silica gel c...

Embodiment 3

[0244] 3-(3,5-Dimethoxyphenyl)-2-{3-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}- N,N-Dimethacrylamide (25)

[0245] Compound 25 which can be represented by the following structural formula:

[0246]

[0247] Prepared as follows: To a clean dry flask with a stir bar was added compound 14 (2.11 g, 4.18 mmol) and dry DMF (5 mL). Carbonyldiimidazole (1.36 g, 8.35 mmol) was then added with stirring and the reaction was heated to 60 °C for 1 h while venting through an oil bubbler. The reaction mixture was then cooled to 0 °C and a solution of 2M dimethylamine (10.5 mL, 21 mmol) in THF was added. The reaction was worked up by partitioning the mixture with 10% citric acid (50 mL), ethyl acetate (250 mL), and water (200 mL). Then the organic phase was washed sequentially with water (2×150 mL), brine (1×100 mL) and washed with anhydrous MgSO 4 dry. Concentration of the organics provided crude product. The crude product was purified by silica gel chromatography eluting...

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Abstract

The invention discloses a novel compound formed by the chemical coupling of a diphenylethlene compound and derivatives thereof as well as thiazolidine or oxazolidine midbody and a preparation method thereof. The invention also discloses a plurality of pharmaceutical applications of the compounds: reducing blood sugar, serum insulin level and triglycercide level of a diabete II animal model, treating diseases related to the insulin tolerance, such as polycystic ovary syndrome, hyperlipemia, coronary disease and ambient vascular diseases, and also treating inflammations and immunological diseases, especially diseases mediated by cytokines and cyclooxygenase cox, such as THF-Alpha, IL-1, IL-6 and / or COX-2.

Description

technical field [0001] The present invention relates to novel compounds formed by chemically coupling diphenylethylene compounds and derivatives thereof with thiazolidine or oxazolidine intermediates. [0002] The present invention also relates to various pharmaceutical uses of these compounds. They effectively provide various useful pharmacological effects. For example, these compounds are useful in reducing blood glucose, serum insulin and triglyceride levels in animal models of type II diabetes. In addition, these compounds are also useful in the treatment of conditions related to insulin resistance, such as polycystic ovary syndrome, as well as hyperlipidemia, coronary heart disease and peripheral vascular disease, and also in the treatment of inflammatory and immune diseases, especially Those diseases are mediated by cytokines and cyclooxygenases such as THF-α, IL-1, IL-6 and / or COX-2. technical background [0003] With the improvement of people's living standards, m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/34C07D417/12C07D263/44A61K31/426A61K31/427A61K31/421A61K31/5377A61P3/10A61P29/00A61P37/02A61P5/48A61P3/06A61P15/00A61P9/10A61P25/00A61P35/00
Inventor 唐田蔡敏英赵金华王彦青朱丹吴筱昆黄传贵刘碧秀
Owner SHENZHEN NEPTUNUS PHARM CO LTD
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