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Preparation method and application of fluorocalciferol CD ring

A technology for calcidol and compounds is applied in the field of preparation of the CD ring of fluorocalcidol, which can solve the problems of expensive raw materials, low safety and high cost, and achieve the effects of high reaction yield, simplified reaction steps and shortened synthesis cycle.

Pending Publication Date: 2022-02-15
甘肃皓天医药科技有限责任公司
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  • Abstract
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Problems solved by technology

[0016] The present invention aims at the above-mentioned existing fluorocalcidol synthesis in which raw materials are expensive, photoreaction ring-opening and thermal isomerization reactions are required, or dangerous reagents such as tert-butyllithium, sodium amalgam, or tri-n-butyltin hydrogen and carbon disulfide are required The phenomenon of causing high cost and low safety problems provides a preparation method and application of an intermediate for the preparation of fluorocalcidol

Method used

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  • Preparation method and application of fluorocalciferol CD ring
  • Preparation method and application of fluorocalciferol CD ring
  • Preparation method and application of fluorocalciferol CD ring

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Experimental program
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Embodiment

[0047] A method for preparing the CD ring of flucalcidol intermediate, the synthetic route of the method is as follows:

[0048]

[0049] Wherein, R in compound VII is a hydroxyl protecting group, especially a hydroxyl protecting group that can be removed by fluorine-containing inorganic salts, fluorine-containing organic salts, or hydrofluoric acid.

[0050] Compound I was prepared by the method disclosed in the literature Journal of Medicinal Chemistry, 2018, 61(15), 6658-6673, and the rest of the raw materials and reagents were obtained from commercial sources.

[0051] Preparation of compound Ⅱ

[0052] Add compound I (136.0g, 275.1mmol) and tetrahydrofuran (1360.0ml) into a 3000ml four-neck flask, cool the reaction down to -70°C to -80°C, and add n-butyl lithium (439.0ml, 1100.3 mmol), keep the temperature for 1 h, quench the reaction with water, separate the organic phase, dry and concentrate to obtain the crude product, the crude product is 70.2 g by column chromato...

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Abstract

The invention discloses a preparation method and application of a fluorocalciferol CD ring, and relates to the field of synthesis of medical intermediates. The invention discloses a preparation method of a compound VII with the following structure, and further the compound VII is used for preparing fluorocalciferol. According to the method, a convergence method is used for synthesis, so that the synthesis period is shortened, and the preparation cost is reduced; wherein the reaction yield is high, and the product quality is easy to control; in addition, the use of dangerous reagents is avoided, the preparation risk is reduced, and large-scale preparation is easy to realize.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a preparation method and application of flucalcidol CD ring. Background technique [0002] Fluocciferol is an analogue of vitamin D that has therapeutic effects on hyperparathyroidism and osteoporosis. In a variety of biological detection systems, it shows stronger biological activity than calcitriol. In the in vitro test, the activation effect of flucalcidol and calcitriol on the vitamin D-responsive gene of rat osteoblast cell line ROB-C26 was compared, and 1α, 25(OH)2- D3-24 hydroxylase mRNA expression level, found that the effect of this product is 10 times stronger than that of calcitriol, its residence time in the cell is longer, and it can permanently activate the target gene in the cell; the research results of nephrectomy rats It is suggested that this product has a certain therapeutic effect on secondary hyperparathyroidism and osteodystrophy c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C07C45/29C07C49/513C07C29/10C07C35/52C07C401/00
CPCC07F7/1804C07F7/1892C07C45/292C07C49/513C07C29/10C07C35/52C07C401/00C07C2602/24C07B2200/07
Inventor 魏鹏飞常德山
Owner 甘肃皓天医药科技有限责任公司
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