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Application of composition of derivatives of Artalbic acid in preparation of anti-osteoporosis medicine

An anti-osteoporosis and osteoporosis technology, applied in drug combinations, medical preparations containing active ingredients, bone diseases, etc., can solve the problems of low safety and high toxicity

Inactive Publication Date: 2016-11-16
南京海澳斯生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing drugs for the treatment of osteoporosis have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity

Method used

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  • Application of composition of derivatives of Artalbic acid in preparation of anti-osteoporosis medicine
  • Application of composition of derivatives of Artalbic acid in preparation of anti-osteoporosis medicine
  • Application of composition of derivatives of Artalbic acid in preparation of anti-osteoporosis medicine

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Embodiment 1

[0014] The preparation of embodiment 1 compound Artalbic acid

[0015] The preparation method of compound Artalbic acid (I) refers to the literature published by Antonella Maggio et al. (Antonella Maggio et al., 2011. Artalbic acid, a sesquiterpene with an unusual skeleton from Artemisia alba (Asteraceae) from Sicily. Tetrahedron Letters, 52 (2011) 4543–4545) approach.

[0016]

Embodiment 2

[0017] Synthesis of O-bromoethyl derivative (II) of embodiment 2 Artalbic acid

[0018] Compound I (266 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 40 °C for 16 h. After 16 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine for 5 times successively, then dried with anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (272mg, 73%) .

...

Embodiment 3

[0023] The synthesis of the O-(dichloroethylamino) ethyl derivative (III) of embodiment 3 Artalbic acid

[0024] 1. Synthesis of O-(dihydroxyethylamino)ethyl derivatives of Artalbic acid

[0025] Compound II (187 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (690 mg, 5.0 mmol), potassium iodide (252 mg, 1.5 mmol) and diethanolamine (1051 mg, 10 mmol) were added thereto, and the mixture was heated to reflux for 1 h. After the reaction was completed, the reaction solution was poured into 20 mL of ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1.0, v / v), and the ...

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Abstract

The invention discloses application of a composition of an O-(diethylamine chloride)ethyl derivative and an O-(bis(2-methylthio ethyl)amido)ethyl derivative of Artalbic acid in preparation of anti-osteoporosis medicine, relates to the field of organic synthesis and medicinal chemistry, and discloses and provides a composition prepared from the O-(diethylamine chloride)ethyl derivative and the O-(bis(2-methylthio ethyl)amido)ethyl derivative of Artalbic acid according to the mass ratio of 35:65 and a method for mixing the compounds according to the mass ratio of 35:65 to prepare the composition. Pharmacological experiments indicate that the composition can inhibit bone turnover rate enhancement and bone destruction which are caused by ovariectomy, meanwhile, the blood calcium concentration can be improved, and bone deposition is promoted. Therefore, the invention further provides application of the composition of the derivatives of Artalbic acid in preparation of the anti-osteoporosis medicine.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a composition, a preparation method and an application thereof. Background technique [0002] Osteoporosis is a systemic, metabolic bone disease characterized by reduction and loss of bone mass, bone fragility and increased risk of fracture. With the aging of the population, the incidence of osteoporosis has also increased rapidly, and it has become an important disease that endangers human health and has brought a huge social and economic burden to the world. Although relevant experts and scholars at home and abroad attach great importance to the prevention and treatment of this disease, there is still a lack of effective therapeutic drugs for this disease. [0003] At present, commonly used clinical drugs for the prevention and treatment of osteoporosis include estrogen replacement drugs, bisphosphonates, selective estrogen receptor modulators, vitamin...

Claims

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Application Information

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IPC IPC(8): A61K31/195C07C217/12C07C323/25A61P19/10
CPCA61K31/195C07C217/12C07C323/25A61K2300/00
Inventor 丁秋菊
Owner 南京海澳斯生物医药科技有限公司
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