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Imidazole diphosphonie acid compound and pharmaceutically-acceptable salt and medicinal application thereof

A technology of imidazole bisphosphonic acid and compounds, which is applied in the field of preparation of drugs for the treatment of metabolic bone diseases, can solve problems such as major side effects, and achieve the effects of inhibiting angiogenesis, inhibiting bone resorption, and inhibiting growth

Active Publication Date: 2012-09-12
北京清辉联诺生物科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, existing bisphosphonate drugs, while treating conditions such as osteoporosis, are also accompanied by significant side effects

Method used

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  • Imidazole diphosphonie acid compound and pharmaceutically-acceptable salt and medicinal application thereof
  • Imidazole diphosphonie acid compound and pharmaceutically-acceptable salt and medicinal application thereof
  • Imidazole diphosphonie acid compound and pharmaceutically-acceptable salt and medicinal application thereof

Examples

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Comparison scheme
Effect test

Embodiment 1

[0044] An imidazole bisphosphonic acid compound, the chemical name is: 1-hydroxy-2-substituted-2-imidazolyl-ethylidene-1,1-bisphosphonic acid, and its structural formula is as follows:

[0045]

[0046] In the above formula, R 1 =C 1 ~C 6 Alkyl, phenyl, or H, Me, F, Br, Cl, OR 3 (R 3 =C 1 ~C 4 Alkyl) and other substituted phenyl groups.

[0047] The above-mentioned imidazole bisphosphonic acid compound (hereinafter referred to as compound 2) is synthesized by the following route:

[0048]

[0049] A specific preparation process is as follows: in a 25ml round neck flask, add 3mmol compound 1, 15mmol H 3 PO 3 and 8ml of toluene, electromagnetically stirred and heated to 80°C, after the solid was completely melted, slowly added 15mmol of phosphorus oxychloride (POCl 3 ), stirred vigorously for 12 to 24 hours, after cooling, removed the toluene solution, added 6ml 6M hydrochloric acid to the reaction flask, refluxed for 1 hour, after cooling, removed the solvent by ...

Embodiment 2

[0068] An imidazole bisphosphonic acid compound, its chemical name is: 1-hydroxy-2-substituted-2-benzimidazolyl-ethylidene-1,1-bisphosphonic acid, the structural formula is as follows:

[0069]

[0070] R 1 =H,C 1 ~C 6 Alkyl or substituted phenyl; Y=H, Me, F, Cl, Br, OR 1 (R 1 =C 1 ~C 4 Alkyl); the above-mentioned imidazole bisphosphonic acid compound (hereinafter referred to as compound 4) is synthesized by the following route:

[0071]

[0072] A specific preparation process is as follows: in a 25ml round neck flask, add 3mmol compound 3, 15mmol H 3 PO 3 Electromagnetically stir with 8ml of toluene and heat to 80°C. After the solid is completely melted, slowly add 15mmol of phosphorus oxychloride, and stir vigorously for 12-24 hours. After cooling, remove the toluene solution and add 6ml of 6M hydrochloric acid to the reaction flask , refluxed for 1 hour, after cooling, the solvent was removed by rotary evaporation, and an appropriate amount of isopropanol was ...

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Abstract

The invention relates to a novel imidazole diphosphonie acid compound and a pharmaceutically-acceptable salt thereof. The diphosphonie acid compound disclosed by the invention, farnesylpyrophosphate synthetase is treated, and lipotropy is enhanced. The type of compound can be used for treating diseases including osteoporosis, hypercalcinemia and the like, and can be applied to cancer chemotherapy, immunotherapy and the like.

Description

technical field [0001] The invention relates to a novel imidazole bisphosphonic acid compound, its pharmaceutically acceptable salt and its application in the preparation of drugs for treating metabolic bone diseases. Background technique [0002] Bisphosphonic acid is an anti-metabolic bone disease drug, and its birth can be traced back to 40 years ago. Fleisch et al. found that pyrophosphate (pyrophosphate) present in plasma and urine can inhibit ectopic calcification. However, pyrophosphate is ineffective when taken orally, and the injection is rapidly hydrolyzed and inactivated by enzymes. Later studies have found that replacing the P-O-P group in the pyrophosphate structure with a P-C-P group can change the physical and chemical properties of pyrophosphate and increase its resistance. The stability of hydrolytic enzymes will change their biological properties and toxicological effects. On this basis, major pharmaceutical companies have successively developed a series o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506A61K31/675A61P3/14A61P19/08A61P19/10A61P35/04
Inventor 王科杨劲松吴涛张永辉
Owner 北京清辉联诺生物科技有限责任公司
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