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Method for preparing 1-hydroxy-2-(imidazo [1, 2-a] pyridine-3-radical) ethylidene-1, 1-bisphosphonic acid compound

A technology of bisphosphonic acid compounds and compounds, applied in the fields of compounds, chemical instruments and methods, and organic chemistry of Group 5/15 elements of the periodic table, which can solve problems such as unfavorable industrial production, environmental pollution, and cumbersome operations

Inactive Publication Date: 2012-02-08
NANJING CORE TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Not only are there many steps, the operation is cumbersome, but also the highly toxic substance sodium cyanide is used, the operation is dangerous, there are many reaction by-products, it is difficult to purify, and it will cause serious pollution to the environment, so it is very unfavorable for industrial production

Method used

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  • Method for preparing 1-hydroxy-2-(imidazo [1, 2-a] pyridine-3-radical) ethylidene-1, 1-bisphosphonic acid compound
  • Method for preparing 1-hydroxy-2-(imidazo [1, 2-a] pyridine-3-radical) ethylidene-1, 1-bisphosphonic acid compound
  • Method for preparing 1-hydroxy-2-(imidazo [1, 2-a] pyridine-3-radical) ethylidene-1, 1-bisphosphonic acid compound

Examples

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Embodiment

[0028] 1.2-(imidazo[1,2-a]pyridin-3-yl)synthesis of ethyl acetate (formula III)

[0029] 93.8g of 2-aminopyridine and 127.3g of trans-4-oxyl-2-butenoic acid ethyl ester dissolved in 0.5L of acetonitrile were refluxed in 1L of acetonitrile for 5-6h, cooled to about 50°C, and decompressed Evaporate the solvent until no more dripping out, then cool to about 60°C, add 2L of petroleum ether, stir and reflux for 1 hour, cool, pour into a beaker, let stand to separate layers, remove the supernatant, stand to cool and crystallize. Add 2 L of petroleum ether to the lower layer, stir and reflux for 1 h, and repeat the above operation. The precipitated crystals were suction filtered and dried. used directly in the next step. Yield: 50%.

[0030] The synthesis of 2.2-(imidazo[1,2-a]pyridin-3-yl)acetic acid (formula IV)

[0031] Mix 60 g of the yellow needle-shaped crystals obtained above with 10% sodium hydroxide solution, heat to reflux, stir and react for 2-3h (TLC detection), cool,...

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Abstract

The invention discloses a method for preparing a 1-hydroxy-2-(imidazo [1, 2-a] pyridine-3-radical) ethylidene-1,1-bisphosphonic acid compound with high purity, which comprises the following steps of: obtaining a compound as shown in a formula (III) through nucleophilic addition of a compound (trans-4-oxygroup-2-ethyl crotonate) as shown in a formula (II) and 2-aminopyridine; hydrolyzing the compound as shown in the formula (III) under alkali condition to obtain a compound as shown in a formula (IV); and phosphorylating the compound as shown in the formula (IV) by adopting toluene as a solvent to obtain a compound as shown in a formula (I). The synthetic process condition of the product is moderate, the aftertreatment is simple, the purity is high, the reaction cost is low, and the profit is high. The industrialized production can be realized easily.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to a preparation method of compound 1-hydroxyl-2-(imidazo[1,2-a]pyridin-3-yl)ethylene-1,1-bisphosphonic acid. Background technique [0002] 1-Hydroxy-2-(imidazo[1,2-a]pyridin-3-yl)ethylene-1,1-bisphosphonic acid compound, Minodronic acid is the third generation of nitrogen-containing Aromatic heterocyclic bisphosphonates, this product was jointly developed by Ono Pharmaceutical Co., Ltd. and Astellas Pharmaceutical Co., Ltd. of Japan. It submitted an application to the Ministry of Health and Welfare of Japan in July 2006, and was approved for marketing for the first time on January 21, 2009. The trade name is They are Recalbon (Ono Pharmaceuticals) and Bonoteo (Astellas Pharmaceuticals). This product is used for the treatment of osteoporosis, by inhibiting the activity of farnesyl pyrophosphate (FPP) synthase in osteoclasts, inhibiting bone resorption of osteoclasts, ...

Claims

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Application Information

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IPC IPC(8): C07F9/6561
Inventor 王雪根何凌云陈彬辉朱新国吴邵嘉张用杰田春梅
Owner NANJING CORE TECH CO LTD
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