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Alfacalcidol derivative and preparation method thereof

A technology for alfacalcidol and its derivatives, which is applied in the field of alfacalcidol derivatives and their preparation, can solve problems such as poor solubility and dissolution, obstacles to clinical promotion of drugs, and low solubility, and achieve improved water solubility , The effect that is conducive to clinical use

Inactive Publication Date: 2019-03-26
ZHUOHE PHARM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Alfacalcidol has strong lipophilicity, and its solubility in water is extremely low. The poor solubility and dissolution rate lead to a decline in the therapeutic effect, which poses a great obstacle to the clinical promotion of the drug.

Method used

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  • Alfacalcidol derivative and preparation method thereof
  • Alfacalcidol derivative and preparation method thereof
  • Alfacalcidol derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] This embodiment discloses a class of alfacalcidol derivatives, the molecular structural formula of which is:

[0021]

[0022] R selected from

Embodiment 2

[0024] This embodiment discloses a preparation method of a class of alfacalcidol derivatives, the chemical equation is:

[0025]

[0026] The preparation method of intermediate 1 is as follows: add 100ml of dichloromethane, 2ml of pyridine, 4.12g of alfacalcidol, 4g of p-toluenesulfonyl chloride into a 250ml reaction bottle, put in an ice bath, stir the reaction overnight with magnetic force, extract the reaction with 5ml of ice water, pump After filtration, the filtrate was concentrated, and the residue was recrystallized from ethanol to obtain 5.9 g of white solid.

[0027] The molecular structural formula of intermediate 1 is:

[0028]

[0029] The preparation method of intermediate 2 is as follows: add 50ml of dimethyl sulfoxide, 7.22g of intermediate 1, and 2.5g of NBS to a 100ml reaction bottle, put it in an ice bath, react under light conditions for 4 hours, add 50ml of ethyl acetate, and extract the mixed solution with ice water for 3 times. The organic layer wa...

Embodiment 3

[0048] This embodiment discloses a preparation method of a class of alfacalcidol derivatives, the chemical equation is:

[0049]

[0050] The preparation method of intermediate 1 is as follows: add 100ml of dichloromethane, 2ml of pyridine, 4.12g of alfacalcidol, 4g of p-toluenesulfonyl chloride into a 250ml reaction bottle, put in an ice bath, stir the reaction overnight with magnetic force, extract the reaction with 5ml of ice water, pump After filtration, the filtrate was concentrated, and the residue was recrystallized from ethanol to obtain 5.9 g of white solid.

[0051] The molecular structural formula of intermediate 1 is:

[0052]

[0053] The preparation method of intermediate 2 is as follows: add 50ml of dimethyl sulfoxide, 7.22g of intermediate 1, and 2.5g of NBS to a 100ml reaction bottle, put it in an ice bath, react under light conditions for 4 hours, add 50ml of ethyl acetate, and extract the mixed solution with ice water for 3 times. The organic layer wa...

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PUM

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Abstract

The invention provides an alfacalcidol derivative and a preparation method thereof. The molecular structural formula is as follows, wherein R is selected from the follows. According to the alfacalcidol derivative and the preparation method thereof provided by the invention, vitamin D3 is taken as an initiator and is subjected to 7-step reaction, thereby acquiring a target product. Compared with alfacalcidol, the alfacalcidol derivative has higher water solubility and is more beneficial to clinic application of drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a class of alfacalcidol derivatives and a preparation method thereof. Background technique [0002] Alfacalcidol is a synthetic vitamin D that forms active vitamin D when ingested. Vitamin D and parathyroid hormone are elements that regulate calcium levels in the body. If blood calcium levels are too low, the body releases parathyroid hormone. Human bones are the place with the largest amount of calcium, and parathyroid hormone can make bone calcium enter the blood. Calcium plays a key role in human body function, high calcium will seriously affect muscle contraction, nervous system function, bone density and blood coagulation mechanism, etc. Since parathyroid hormone levels may be artificially elevated in dialysis patients, alfacalcidol can be used to stabilize the calcium regulatory system and maintain normal parathyroid hormone levels. Alfacalcidol has strong l...

Claims

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Application Information

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IPC IPC(8): C07C401/00C07D207/08C07D233/02C07D265/30C07D263/06C07D279/12
CPCC07C401/00C07C2601/14C07C2602/24C07D207/08C07D233/02C07D263/06C07D265/30C07D279/12
Inventor 王涛李晓明王庆林王彬彬孙益林
Owner ZHUOHE PHARM GRP CO LTD
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