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Vitamin D3 compound and preparation method thereof

A compound and vitamin technology, applied in organic chemistry and other directions, can solve the problems of low solubility, obstacles to clinical promotion of drugs, and decreased therapeutic effect, and achieve the effect of improving water solubility and benefiting clinical use.

Inactive Publication Date: 2019-03-12
WUXI FORTUNE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Vitamin D 3 Belonging to the fat-soluble vitamin D family, the solubility in water is low, and 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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  • Vitamin D3 compound and preparation method thereof
  • Vitamin D3 compound and preparation method thereof
  • Vitamin D3 compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] This example discloses a compound A1 prepared according to the above method, its structural formula is as follows:

[0029]

[0030] The preparation method of compound A1:

[0031] 1.1) Synthesis of Intermediate 1

[0032]

[0033] Add 100ml of dichloromethane, 2ml of pyridine, and vitamin D to a 250ml reaction bottle 3 4.12g, 4g p-toluenesulfonyl chloride, ice bath, magnetic stirring reaction overnight, 5ml ice water extraction to quench the reaction, suction filtration, the filtrate was concentrated, and the residue was recrystallized from ethanol to obtain 5.9g of white solid, namely Intermediate 1.

[0034] 1.2) Synthesis of Intermediate 2

[0035]

[0036] Add 50ml of dimethyl sulfoxide, 7.22g of intermediate 1, 2.5g of NBS to a 100ml reaction bottle, and react in an ice bath for 4 hours under light conditions, add 50ml of ethyl acetate, extract the mixed solution with ice water for 3 times, and concentrate the organic layer to obtain the intermediate 2...

Embodiment 2

[0047] This embodiment discloses a compound A6 prepared according to the above method, and its structural formula is as follows:

[0048]

[0049] Preparation of Compound A6:

[0050] 2.1) Synthesis of intermediate 1

[0051]

[0052] Add 100ml of dichloromethane, 2ml of pyridine, and vitamin D to a 250ml reaction bottle 3 4.12g, 4g p-toluenesulfonyl chloride, ice bath, magnetic stirring reaction overnight, 5ml ice water extraction to quench the reaction, suction filtration, the filtrate was concentrated, and the residue was recrystallized from ethanol to obtain 5.9g of white solid, namely Intermediate 1.

[0053] 2.2) Synthesis of intermediate 2

[0054]

[0055] Add 50ml of dimethyl sulfoxide, 7.22g of intermediate 1, 2.5g of NBS to a 100ml reaction bottle, and react in an ice bath for 4 hours under light conditions, add 50ml of ethyl acetate, extract the mixed solution with ice water for 3 times, and concentrate the organic layer to obtain the intermediate 2, di...

Embodiment 3

[0066] This embodiment discloses a compound A8 prepared according to the above method, and its structural formula is as follows:

[0067]

[0068] Preparation of Compound A8:

[0069] 3.1) Synthesis of intermediate 1

[0070]

[0071] Add 100ml of dichloromethane, 2ml of pyridine, and vitamin D to a 250ml reaction bottle 3 4.12g, 4g p-toluenesulfonyl chloride, ice bath, magnetic stirring reaction overnight, 5ml ice water extraction to quench the reaction, suction filtration, the filtrate was concentrated, and the residue was recrystallized from ethanol to obtain 5.9g of white solid, namely Intermediate 1.

[0072] 3.2) Synthesis of intermediate 2

[0073]

[0074] Add 50ml of dimethyl sulfoxide, 7.22g of intermediate 1, 2.5g of NBS to a 100ml reaction bottle, and react in an ice bath for 4 hours under light conditions, add 50ml of ethyl acetate, extract the mixed solution with ice water for 3 times, and concentrate the organic layer to obtain the intermediate 2, di...

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Abstract

The invention provides a vitamin D3 compound. A structural formula of the vitamin D3 compound is shown in the following formula (the formula is shown in the description). The water solubility of the vitamin D3 compound improved and the vitamin D3 compound is more beneficial to clinic use of drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a vitamin D3 compound and a preparation method thereof. Background technique [0002] Vitamin D 3 (Vitamin D 3 ) also known as cholecalciferol is a kind of vitamin D, the 7-dehydrocholesterol generated after cholesterol dehydrogenation can form vitamin D after ultraviolet irradiation 3 , so that vitamin D 3 The provitamin D is 7-dehydrocholesterol. [0003] Vitamin D 3 It can improve the body's absorption of calcium and phosphorus, and make the levels of plasma calcium and phosphorus reach saturation; promote growth and bone calcification, and promote tooth health; increase phosphorus absorption through the intestinal wall, and increase phosphorus reabsorption through the renal tubules; Maintains normal levels of citrate in the blood and prevents loss of amino acids through the kidneys. Clinically, it is mainly used for rickets, osteomalacia and infantile tetany...

Claims

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Application Information

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IPC IPC(8): C07C401/00C07D265/32C07D207/12C07D279/12C07D241/04C07D233/02C07D263/06
CPCC07C401/00C07C2601/14C07C2602/24C07D207/12C07D233/02C07D241/04C07D263/06C07D265/32C07D279/12
Inventor 王涛王彬彬王庆林游本加蒲建新
Owner WUXI FORTUNE PHARMA
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