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Bisphosphonate compounds as well as preparation method and application thereof

Technology of a compound, bisphosphonic acid, applied in the field of biomedicine

Active Publication Date: 2016-11-09
CHENGDU YUNKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 2. Long-term use of bisphosphonic acid currently on the market will have certain toxic and side effects such as liver and kidney toxicity. Therefore, the development of bisphosphonic acid with high efficiency, low toxicity and small side effects is the gospel for the majority of osteoporosis patients and has a broad application prospect

Method used

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  • Bisphosphonate compounds as well as preparation method and application thereof
  • Bisphosphonate compounds as well as preparation method and application thereof
  • Bisphosphonate compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: Synthetic SCDP-1 compound

[0056] In this example, the diphosphonic acid compound is: 3-selenohydroxy-2-amino-1-hydroxypropylene-1,1-diphosphonic acid. The structural formula is as follows

[0057]

[0058] The specific preparation method of this compound is as follows:

[0059] Add 1.68 g of 3-selenohydroxy 2-amino-propionic acid into a 50 mL three-necked flask. Add 10 mL of tetrahydrofuran, stir and add 2.4 g of catecholborane, react for 2 hours, then add 9.0 g of tris-(trimethylsilyl) phosphite, react for 2 hours, add methanol 40 mL and react for 2 hours. Distill under reduced pressure until an oily substance was produced, then add 300 mL of diethyl ether to precipitate a precipitate, and recrystallize the precipitate with water to obtain a white solid 3-selenohydroxy-2-amino-1-hydroxypropylidene-1,1-diphosphonic acid.

[0060] The white solid was identified by:

[0061] 1 H-NMR (400MHz, D 2 O) δ 2.65 (T, 1H), δ 1.41-1.72 (D, 2H). MS (ESI, m / ...

Embodiment 2

[0063] Embodiment 2: Synthetic SCDP-2 compound

[0064] In this example, the diphosphonic acid compound is: 3-methylselenyl-2 amino-1 hydroxypropylene-1,1-diphosphonic acid. The structural formula is as follows

[0065]

[0066] The specific preparation method of this compound is as follows:

[0067] Add 1.82 g of 3-methylselenyl-2-amino-propionic acid into a 50 mL three-necked flask. Add 10 mL of tetrahydrofuran, stir and add 2.4 g of catecholborane, react for 2 hours, then add 9.0 g of tris-(trimethylsilyl) phosphite, react for 2 hours, add methanol 40 mL and react for 2 hours. Distill under reduced pressure until an oily substance was produced, then add 300 mL of diethyl ether to precipitate a precipitate, and recrystallize the precipitate with water to obtain a white solid 3-methylseleno-2amino-1-hydroxypropylidene-1,1-diphosphonic acid.

[0068] The white solid was identified by:

[0069] 1 H-NMR (400MHz, D 2 O) δ 2.68 (T, 1H), δ 1.43-1.74 (D, 2H), δ, 0.98 (S, 3H...

Embodiment 3

[0071] Embodiment 3: Synthetic SCDP-3 compound

[0072] In this example, the diphosphonic acid compound is: 4-methylselenyl-2-amino-1 hydroxypropylene-1,1-diphosphonic acid. The structural formula is as follows:

[0073]

[0074] The specific preparation method of this compound is as follows:

[0075] Add 1.96 g of 4-methylselenyl-2-amino-butyric acid into a 50 mL three-necked flask. Add 10 mL of tetrahydrofuran, stir and add 2.4 g of catecholborane, react for 2 hours, then add 9.0 g of tris-(trimethylsilyl) phosphite, react for 2 hours, add methanol 40 mL and react for 2 hours. Distill under reduced pressure until an oily substance was produced, then add 300 mL of diethyl ether to precipitate a precipitate, and recrystallize the precipitate with water to obtain a white solid 4-methylselenyl-amino-1-hydroxybutylene-1,1-diphosphonic acid.

[0076] The white solid was identified by:

[0077] 1 H-NMR (400MHz, D 2 O) δ 2.68 (T, 1H), δ 1.53 (Q, 2H), δ 1.32 (T, 2H) δ, 0.99 ...

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PUM

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Abstract

The invention discloses bisphosphonate compounds. The bisphosphonate compounds have a structure shown in a formula II, wherein R1 is H, OH or halogen; R2 is an alkyl group M adopting a linear structure or a structure with a branched chain, a ring or an aromatic ring, and the alkyl group M contains 1 20 carbon atoms; R3 is H, OH, CN or an alkyl group N containing 1 20 carbon atoms. The novel bisphosphonate compounds enable bone formation and bone destruction of osteocytes to be kept in relatively ideal dynamic equilibrium for a patient suffering from senile osteoporosis.

Description

technical field [0001] The invention relates to a novel bisphosphonate compound and a method for preparing the novel bisphosphonate compound, belonging to the field of biomedicine. Background technique [0002] Osteoporosis (OP) is a systemic bone disease characterized by low bone mass and damage to bone microstructure, resulting in increased bone fragility and susceptibility to fracture. At present, osteoporosis ranks 7th among common diseases and frequently-occurring diseases in the world, with a total of more than 200 million patients. More than 90 million people in my country suffer from different degrees of osteoporosis. The prevalence of osteoporosis in the elderly over 60 years old is about 50%~ 60%. [0003] Bisphosphonic acid has been widely used in the treatment of osteoporosis, malignant tumor-related diseases such as hypercalcemia and bone pain, osteitis deformans and other metabolic bone diseases. The basic molecular structure of bisphosphonic acid is two phosp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38A61P19/10
CPCC07F9/3808C07F9/3817C07F9/3882
Inventor 李明起潘俊男王翰曾永龙曹刚文德仲程作用邓启民段玉春蒋雪刘媛媛
Owner CHENGDU YUNKE PHARMA
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