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Application of composition of artalbic acid benzimidazolyl and dihydroxyethylamino derivatives in preparing anti-osteoporosis drugs

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: 2016-11-09
南京海澳斯生物医药科技有限公司
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  • Summary
  • 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 artalbic acid benzimidazolyl and dihydroxyethylamino derivatives in preparing anti-osteoporosis drugs
  • Application of composition of artalbic acid benzimidazolyl and dihydroxyethylamino derivatives in preparing anti-osteoporosis drugs
  • Application of composition of artalbic acid benzimidazolyl and dihydroxyethylamino derivatives in preparing anti-osteoporosis drugs

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Experimental program
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Effect test

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] Example 3 Synthesis of O-(benzimidazolyl) ethyl derivatives (III) of Artalbic acid

[0024] Compound II (187mg, 0.5mmol) was dissolved in 20mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and benzimidazole (1180mg, 10mmol) were added thereto, and the mixture was heated to reflux for 2h . After the reaction, the reaction solution was poured into ice water, extracted twice 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 concentrated brown elution band was collected and concentrated to give compound III as a brown solid (80.0 mg, 39%).

[0025] 1 H NMR(5...

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry. The invention discloses and provides a composition, which is prepared from O-(benzimidazolyl) ethyl and (dihydroxyethylamino) ethyl derivatives of Artalbic acid according to a mass ratio of 30 to 70, and a method for preparing the composition by mixing the compounds according to the mass ratio of 30 to 70. Pharmacological experiments show that the composition provided by the invention can inhibit ovary-caused bone conversion rate enhancing and bone destruction, and meanwhile, the composition is capable of increasing a blood calcium concentration and is conducive to bone deposition. The composition has an effect on preventing and treating osteoporosis caused by estrogen deficiency and the composition is free from estrogen-like side effects. Therefore, the invention also provides an application of the composition, which is prepared from the O-(benzimidazolyl) ethyl and (dihydroxyethylamino) ethyl derivatives of the Artalbic acid according to the mass ratio of 30 to 70, in preparing anti-osteoporosis drugs.

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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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4184A61K31/195A61P19/10A61P5/30C07D235/06C07C217/12
CPCA61K31/195A61K31/4184C07C217/12C07D235/06A61K2300/00
Inventor 丁秋菊
Owner 南京海澳斯生物医药科技有限公司
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