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Sulfonamide derivative and application thereof in osteoporosis drugs

A technology of derivatives and sulfonamide, applied in the field of sulfonamide derivatives and their application in osteoporosis drugs, can solve problems such as heavy economic burden on patients

Inactive Publication Date: 2018-05-08
刘双伟
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] BMP-2 is of great significance to the treatment of osteoporosis, but the use of recombinant human BMP-2 protein will bring heavy economic burden to patients

Method used

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  • Sulfonamide derivative and application thereof in osteoporosis drugs
  • Sulfonamide derivative and application thereof in osteoporosis drugs
  • Sulfonamide derivative and application thereof in osteoporosis drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] : Embodiment 1: the synthesis of N-(furan-2-yl)-3-nitrobenzenesulfonamide:

[0026]

[0027] 3-Nitrobenzenesulfonyl chloride (1.22 mmol) was slowly added dropwise to a solution of furan-2-amine (0.812 mmol) in pyridine (10 mL) previously cooled in an ice-water bath. The mixture was stirred at 0 °C overnight. use CH 2 Cl 2 (20 mL) and extract the mixture with 3N HCl. use CH 2 Cl 2 The aqueous part was extracted once, then washed with Na 2 SO 4 The organic layer was dried and concentrated. The mixture was purified by column chromatography using ethyl acetate and hexane to afford N-(furan-2-yl)-3-nitrobenzenesulfonamide with a purity of 99%. Alternatively add water (100ml) to collect the solid and remove from MeOH:CH 2 Cl 2 Medium recrystallization gave 0.190 g of white crystals with a yield of 87%. 1 H-NMR (400 MHz, CDCl3) δ:6.67(t,1H), 6.99(dd, 1H), 7.87(dd, 1H), 7.96(t,1H), 8.42(s, 1H), 8.53(d, 1H), 8.88(s, 1H). 13 C-NMR (125 MHz, CDCl3) δ:103.06,108.09,...

Embodiment 2

[0028] Example 2: Synthesis of 3-amino-N-(furan-2-yl)benzenesulfonamide:

[0029]

[0030] A Pd-C (5 mmol) catalyst was added to a solution of N-(furan-2-yl)-3-nitrobenzenesulfonamide (10 mmol) in ethanol. In the presence of hydrazine hydrate (50 mmol), the mixture was reacted at 100°C under 150W microwave irradiation for 20 minutes. The progress of the reaction was monitored by TLC. After the reaction was complete the catalyst was isolated by filtration. The reaction solvent was evaporated under reduced pressure to obtain 2.18 g of a liquid product, 3-amino-N-(furan-2-yl)benzenesulfonamide, with a yield of 92%. 1 H-NMR (400 MHz, CDCl3) δ:3.61(s,2H), 6.66(t, 1H), 6.87(d, 1H), 6.98(d, 1H), 7.06(s, 1H), 7.27(d, 1H), 7.35(t,1H), 7.86(d, 1H). 13 C-NMR (125 MHz, CDCl3) δ:103.06, 108.09, 114.70, 121.15,124.39, 126.99, 137.34, 141.60, 145.61,160.02. LC-MS(ESI, pos, ion) m / z: 239[M+1 ].

Embodiment 3

[0031] Example 3: Synthesis of N-(furan-2-yl)-3-(((tetrahydro-2H-pyran-3-yl)methyl)amino)benzenesulfonamide

[0032]

[0033]In a glass flask with a capacity of 200 ml equipped with a stirring device, a thermometer, a reflux condenser and a dropping funnel, 11.39 g (47.8 mmol) of 3-amino-N-(furan-2-yl) benzenesulfonamide, 6.93 g of potassium carbonate g (50.1 mmol) and 60 ml of N,N-dimethylformamide were added under nitrogen atmosphere. While stirring at room temperature, 8.99 g (50.2 mmol) of 3-methyl bromide-tetrahydropyran was added, and the mixture was reacted at 70-80°C for 3-4 hours. After the reaction was completed, the mixture was cooled to room temperature, and then 200 ml of toluene was added. After washing twice with water (180 ml), it was dried over magnesium sulfate. After filtration, it was concentrated under reduced pressure. The obtained yellow oil was then purified using silica gel column chromatography (filler: Wakogel C-200, eluent: hexane / ethyl acetat...

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Abstract

The invention belongs to the field of pharmacy research, and particularly discloses a sulfonamide derivative and application thereof in osteoporosis drugs. The specific structure is shown in the description. It is found through pharmacy research that the compound has relatively good in-vitro BMP-2 raising activity, can further serve as the osteoporosis drugs for pharmacological toxicology experiments, drug dosage form development, drug clinical tests and other deeper research and development till the drugs appear in the market, so that problems of patients suffering from osteoporosis are solved.

Description

technical field [0001] The invention relates to a sulfonamide derivative and its application in osteoporosis medicine, in particular to the application of a BMP-2 up-regulating active medicine in the preparation of osteoporosis medicine. Background technique [0002] Osteoporosis (Osteoporosis, OP) is a systemic bone disease, characterized by decreased bone mass and destruction of bone microstructure, manifested as increased bone fragility, thus greatly increasing the risk of fracture, even if it is mild Fractures are also prone to occur with or without trauma. Osteoporosis is a multifactorial chronic disease. Before the fracture occurs, there are usually no special clinical manifestations. The disease is more common in women than in men and is common in postmenopausal women and the elderly. With the increase of the elderly population in my country, the incidence of osteoporosis is on the rise, and it is a health problem worthy of attention in my country and even in the w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/12A61K31/351A61P19/10
CPCC07D407/12
Inventor 刘双伟
Owner 刘双伟
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