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Flavonoid derivative for treating osteoporosis as well as pharmaceutical composition and application thereof

A technology of osteoporosis and flavonoids, applied in the field of medicine, can solve the problems of increasing human and financial burden on families and society

Inactive Publication Date: 2018-11-20
RIZHAO PUDA PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This not only caused serious physical and mental damage to the patients, but also added a huge human and financial burden to the family and society.

Method used

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  • Flavonoid derivative for treating osteoporosis as well as pharmaceutical composition and application thereof
  • Flavonoid derivative for treating osteoporosis as well as pharmaceutical composition and application thereof
  • Flavonoid derivative for treating osteoporosis as well as pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Synthesis of 3'-chloro-7-ethoxyisoflavones.

[0076] The synthesis steps are:

[0077]

[0078] ;

[0079] Dissolve 4-ethoxy-2-hydroxyacetophenone B (20g, 6.5mol) in tetrahydrofuran (100ml), add lithium hexamethyldisilazide (LiHMDS) (60ml), stir and mix for 2h to ensure that the acyl Lithium enolate can be completely formed, then add 3-chlorobenzoyl chloride C (22g, 6.5mol) and continue stirring for 3h to generate β-propanedione compound D; add sulfuric acid (30ml) and Acetic acid (20ml), heated at 120°C and refluxed for 4-5h, initially cooled to 22°C, adjusted the pH to 8 with an alkali neutralizer, and solids precipitated; continued to cool the precipitated solids to 5°C, stirred and crystallized for 1h, filtered, and used The filter cake was washed with ethyl acetate, followed by recrystallization with methanol, acetone and pure water, and vacuum-dried to obtain solid compound 3'-chloro-7-ethoxyisoflavone A (1) (37.2g), 94.5%.

Embodiment 2

[0081] Synthesis of 3'-chloro-4'-nitro-7-ethoxyisoflavones.

[0082] The synthesis steps are:

[0083]

[0084] ;

[0085] Dissolve 4-ethoxy-2-hydroxyacetophenone B (20g, 6.5mol) in tetrahydrofuran (100ml), add lithium hexamethyldisilazide (LiHMDS) (60ml), stir and mix for 2h to ensure that the acyl Lithium enolate can be completely formed, then add 3-chloro-4-nitrobenzoyl chloride C (22g, 6.5mol) and continue to stir for 3h to generate β-propanedione compound D; add to the reaction system Sulfuric acid (30ml) and acetic acid (20ml), heat at 100°C and reflux for 4-5h, initially cool down to 20°C, adjust the pH to 9 with an alkali neutralizer, and solids precipitate; continue to cool the precipitated solids to 10°C, stir and crystallize Filter after 1h, wash the filter cake with ethyl acetate, recrystallize with methanol, acetone and pure water successively, and dry in vacuo to obtain the solid compound 3'-chloro-4'-nitro-7-ethoxyisoflavone A ( 2) (32.8g), the yield was...

Embodiment 3

[0087] Synthesis of 3'-chloro-4'-amino-7-ethoxyisoflavones.

[0088] The synthesis steps are:

[0089]

[0090] ;

[0091] Dissolve 4-ethoxy-2-hydroxyacetophenone B (20g, 6.5mol) in tetrahydrofuran (100ml), add lithium hexamethyldisilazide (LiHMDS) (30ml), stir and mix thoroughly for 2h to ensure that the acyl Lithium enolate can be completely formed, then add 3-chloro-4-aminobenzoyl chloride C (22g, 6.5mol) and continue to stir for 3h to generate β-propanedione compound D; add sulfuric acid to the reaction system (30ml) and acetic acid (20ml), heat at 130°C and reflux for 4-5h, initially cool down to 24°C, adjust the pH to 8 with an alkali neutralizer, and solids precipitate; continue to cool the precipitated solids to 7°C, stir and crystallize for 1h After filtration, the filter cake was washed with ethyl acetate, recrystallized with methanol, acetone and pure water in turn, and dried in vacuo to obtain the solid compound 3′-chloro-4′-amino-7-ethoxyisoflavone A (3) (...

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PUM

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Abstract

The invention provides a flavonoid derivative for treating osteoporosis as well as a pharmaceutical composition and application thereof. The flavonoid derivative has a chemical structure shown as thefollowing formula A. The structural formula is as shown in the description. The product disclosed by the invention is the flavonoid derivative. The influence of estrogen on the reproductive system does not exist in the human body, but the activity of the estrogen can be increased, and the flavonoid derivative has the characteristic of estrogenic osteoporosis resistance and can achieve effects of reducing bone loss and increasing bone mineral density. The main anti-osteoporosis mechanisms are that (1) osteocyte proliferation can be promoted, bone collagen synthesis and mineralization of the bone matrix can be promoted, and the bone mass is increased; (2) proliferation and differentiation of osteoclast precursor cells can be reduced, the activity of the osteoclast is inhibited, and bone resorption is reduced; and (3) calcitonin secretion is increased by virtue of the estrogenic effect, and bone resorption resistance is indirectly produced.

Description

Technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a flavonoid derivative for treating osteoporosis and its pharmaceutical composition and application. Background technique [0002] Osteoporosis is a worldwide health problem that attracts more and more attention. At present, about 200 million people in the world suffer from osteoporosis, and its incidence rate has leapt to the seventh among common diseases and frequently-occurring diseases. Osteoporosis is the most common disease of the elderly. In the United States and Western countries, half of postmenopausal women over 55 years old suffer from different degrees of osteoporosis, while over 95% of elderly people over 65 years old suffer from osteoporosis. With the development of science and the progress of mankind, the average life expectancy has been continuously extended, the elderly population has increased rapidly, and the incidence of osteoporosis ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61P19/10A61K31/352
CPCA61P19/10C07D311/36
Inventor 不公告发明人
Owner RIZHAO PUDA PHARMA TECH CO LTD
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