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A heterocyclic compound for treating osteoporosis and its preparation method and application

A technology of heterocyclic compounds and compounds, applied in the field of medicine, can solve problems such as efficacy and side effects that have not been fully studied

Active Publication Date: 2019-10-11
MUDANJIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Calcium products are known to have fewer side effects and excellent efficacy, but it is a preventative rather than a therapeutic
In addition, vitamin D preparations such as calcitonin are known, but their efficacy and side effects have not been adequately studied

Method used

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  • A heterocyclic compound for treating osteoporosis and its preparation method and application
  • A heterocyclic compound for treating osteoporosis and its preparation method and application
  • A heterocyclic compound for treating osteoporosis and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: 1-(pyridin-2-yl)-1H-pyrazol-5-ylbenzofuran-2-carboxylate (compound 1)

[0058]

[0059] Step 1) 3-Oxo-propionic acid ethyl ester (2.32g, 20.0mmol) and ethanol (20mL) were placed in a round bottom flask, and slowly added dropwise at 0°C with 2- Hydrazinopyridine (2.58 g, 23.6 mmol). The resulting solution was heated at 100° C. for 3 days at reflux. The solvent was removed by distillation under reduced pressure, and the resulting solid was washed with hexane and ethyl acetate and dried in vacuo to obtain 2.91 g of white solid 1-(pyridin-2-yl)-1H-pyrazol-5-ol, Yield 90%.

[0060] ESI-MS: 162.06[M+H] +

[0061] Step 2) under ice bath condition, mix 2-hydroxyl-benzaldehyde (2.68g, 22.0mmol) and anhydrous K 2 CO 3 (4.4g, 31.2mmol) was dissolved in DMF (40ml), and ethyl bromoacetate (4.1g, 26.0mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at -5°C for 30 minutes, and then reacted in an oil bath at 50°C f...

Embodiment 2

[0067] Example 2: 3-methyl-4-phenyl-1-(pyridin-2-yl)-1H-pyrazol-5-ylbenzofuran-2-carboxylate (compound 2)

[0068]

[0069] Step 1) 3-oxo-2-phenyl-propionic acid ethyl ester (4.12g, 20.0mmol) and ethanol (20mL) were placed in a round bottom flask, and slowly added dropwise with ethanol (20mL ) diluted 2-hydrazinopyridine (2.58 g, 23.6 mmol). The resulting solution was heated at 100° C. for 3 days at reflux. The solvent was removed by distillation under reduced pressure and the resulting solid was washed with hexane and ethyl acetate and dried in vacuo to give 3-methyl-4-phenyl-1-(pyridin-2-yl)-1H as a white solid - 4.42 g of pyrazol-5-ol, yield 88%.

[0070] ESI-MS: 252.11[M+H] +

[0071] Step 2) under ice bath condition, mix 2-hydroxyl-benzaldehyde (2.68g, 22.0mmol) and anhydrous K 2 CO 3 (4.4g, 31.2mmol) was dissolved in DMF (40ml), and ethyl bromoacetate (4.1g, 26.0mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred ...

Embodiment 3

[0077] Example 3: 3-(piperidin-1-yl)-1-(pyridin-2-yl)-1H-pyrazol-5-ylbenzothiophene-2-carboxylate (Compound 3)

[0078]

[0079]Step 1) Place 3-oxo-3-(piperidin-1-yl)-propionic acid ethyl ester (4.02g, 20.0mmol) and ethanol (20mL) in a round bottom flask, and slowly 2-Hydrazinopyridine (2.58 g, 23.6 mmol) diluted with ethanol (20 mL) was added dropwise. The resulting solution was heated at 100° C. for 3 days at reflux. The solvent was removed by distillation under reduced pressure, and the resulting solid was washed with hexane and ethyl acetate and dried in vacuo to give a white solid 3-(piperidin-1-yl)-1-(pyridin-2-yl)- 3.91 g of 1H-pyrazol-5-ol, yield 81%.

[0080] ESI-MS: 245.13[M+H] +

[0081] Step 2) under ice bath condition, mix 2-nitro-benzaldehyde (3.02g, 20mmol) and anhydrous K 2 CO 3 (4.4g, 31.2mmol) was dissolved in DMF (40ml), and ethyl thioglycolate (2.40g, 20mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was sti...

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Abstract

The invention relates to the field of a medicine for preventing and treating osteoporosis. The invention provides a pyrazole heterocyclic compound or pharmaceutically acceptable salt of the compound. An in-vivo test finds out that the pyrazole heterocyclic compound can be used for inhibiting bone turnover rate enhancement and bone destruction, which are caused by ovariectomy; meanwhile, the concentration of blood calcium can be improved and deposition of bones is facilitated, so that the pyrazole heterocyclic compound has remarkable effects of preventing and treating the osteoporosis.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a pyrazole heterocyclic compound. The present invention also relates to the preparation method of the compound, its pharmaceutical composition and its use in the preparation of medicines for preventing or treating osteoporosis. Background technique [0002] Osteoporosis is a disorder characterized by a marked decrease in systemic bone mass characterized by microarchitectural destruction of bone tissue, which leads to increased bone fragility and pathological fractures. Bone mass is affected by various factors such as genetics, nutrition, changes in hormone levels, differences in exercise and lifestyle, etc., and the main causes of osteoporosis are known to be aging, lack of exercise, underweight, smoking, low calcium diet Ingestion, menopause, oophorectomy, etc. For most people, bone mass peaks at age 14-18 and decreases by about 1% per year in old age. At present...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C07D409/14C07D495/04C07D401/14A61K31/4439A61K31/506A61K31/5377A61K31/497A61P19/10
Inventor 于涛孙海峰苏晖陈佳权袁春华李美姗张丹
Owner MUDANJIANG MEDICAL UNIV
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