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Doxercalciferol and preparation method thereof

A technology for the chemical reaction of doxercalcidol, applied in the field of doxocalcidol and its preparation, can solve the problems of difficult to control product purity, difficult to standardize operation, unstable yield, etc., and achieve great application value and economic value, Mild reaction and good product purity

Pending Publication Date: 2021-11-19
JIANGSU SIHUAN BIOENGINEERING PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Combining the two routes, the process has merits, but the steps are cumbersome. The two routes also have free radical reactions and other operations that are difficult to standardize. The yield is unstable and the product purity is difficult to control.

Method used

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  • Doxercalciferol and preparation method thereof
  • Doxercalciferol and preparation method thereof
  • Doxercalciferol and preparation method thereof

Examples

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preparation example Construction

[0050] The synthetic reaction chemical equation of the preparation method of described calciferol is:

[0051]

Embodiment 1

[0053] A preparation method of calciferol, comprising the following steps:

[0054] S1 Vitamin D 2 Synthesis of intermediate vitamin D by sulfonylation reaction 2 p-toluenesulfonate ester (IM1), comprising the following steps:

[0055] Under the protection of nitrogen, add 4.0kg of vitamin D to the reaction kettle in sequence 2 , 14L of dichloromethane, 4kg of pyridine, stirred until dissolved, cooled the reaction system to 0°C, added 0.2kg of 4-dimethylaminopyridine and 4.0kg of p-toluenesulfonyl chloride, reacted at 0°C for 71h, and controlled the temperature to 0 ℃, slowly add 10L deionized water to the reaction solution to quench the reaction, after the addition, continue to stir for 10min, let stand to separate the liquid, separate the organic phase, adjust the pH to 1 with 1M sulfuric acid, stand to separate, and use the organic layer The saturated sodium carbonate solution was adjusted to pH = 7, the organic layer was separated, stirred and dried with 2.5 kg of anhyd...

Embodiment 2

[0081] A preparation method of calciferol, comprising the following steps:

[0082] S1 Vitamin D 2 Synthesis of intermediate vitamin D by sulfonylation reaction 2 p-toluenesulfonate ester (IM1), comprising the following steps:

[0083] Under nitrogen protection conditions, add dichloromethane, 5.0kg vitamin D to the reactor 2 , pyridine, stirred until dissolved, cooled the reaction system to 5°C, added 4-dimethylaminopyridine and p-toluenesulfonyl chloride, reacted at 5°C for 48 hours, controlled the temperature at 5°C, and added deionized water dropwise after the reaction was complete Quenching the reaction, adding and continuing to stir to obtain a mixed solution, the mixed solution was left to separate liquids, and the organic phase was separated, adjusted to pH=1 with sulfuric acid, left to separate layers, and the organic layer was adjusted to pH=8 with saturated sodium bicarbonate solution, Separate the organic layer and stir and dry it with anhydrous magnesium sulfat...

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Abstract

The invention provides a doxercalciferol and a preparation method thereof. The preparation method comprises the following steps: sequentially performing sulfonylation reaction, methoxy-bridged ring forming reaction and oxidation reaction on vitamin D2 serving as an initial material to obtain an intermediate 1a-OH-3, 5-cyclized vitamin D2, the intermediate 1a-OH-3, 5-cyclized vitamin D2 is sequentially subjected to a ring-opening reaction, a Diels-Alder reaction, a separation and purification reaction to obtain a doxercalciferol crude product, and a recrystallization reaction is performed on the doxercalciferol crude product to obtain the doxercalciferol. According to the doxercalciferol and the preparation method thereof, the preparation method is simple in process and stable in yield, the prepared product is high in purity, and industrial production is facilitated.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a docalciferol and a preparation method thereof. Background technique [0002] Doxercalciferol, the chemical name is (5Z,7E,22E)-9,10-cycloergosta-5,7,10(19),22-tetraene-1α,3β-diol, its The chemical structural formula is as follows: [0003] [0004] Docalciferol is a selective vitamin D receptor (VDR) agonist, mainly acts on the parathyroid gland, has a higher affinity with the parathyroid gland VDR, metabolizes in the liver, and increases blood calcium and blood phosphorus to a small extent Concentration, less side effects on bones and intestinal tract, approved by FDA to reduce parathyroid hormone (iPTH) levels in patients with secondary hyperparathyroidism (SHPT) undergoing chronic renal dialysis, with good Curative effect and relatively low side effect, have extensive clinical application prospect. [0005] The synthetic route of the docecalcidol reported i...

Claims

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Application Information

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IPC IPC(8): C07C401/00
CPCC07C401/00C07C2601/14C07C2602/24C07B2200/07
Inventor 江永红丁月萍刘红刘蕾陶冬梅
Owner JIANGSU SIHUAN BIOENGINEERING PHARM CO LTD
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