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Cytarabine prodrug related substance and application thereof

A technology of cytarabine and related substances, which is applied in the field of medicine, can solve the problems of poor water solubility, achieve low detection limit, good linearity, and improve the quality of medicines

Pending Publication Date: 2021-11-09
XIAN XINTONG PHARM RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the inventors have found that the cytarabine prodrug has poor water solubility and contains phosphate and cytosine structures in its structure, which is easy to process during its (bulk drug) storage, transportation and preparation into (drug) preparations. produce related substances
However, there are few reports on the related substances of cytarabine prodrug in the prior art

Method used

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  • Cytarabine prodrug related substance and application thereof
  • Cytarabine prodrug related substance and application thereof
  • Cytarabine prodrug related substance and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] 4-Amino-1-([5-O-(2R,4R)-2-oxyl-4-(4-pyridine)-1,3,2-dioxaphosphorin-2-yl]- Generation and preparation of β-D-arabinofuranosyl)-2(1H)-pyrimidinone (Formula 5) reference substance:

[0069]

[0070] In a 50mL three-necked flask, add 50g of dimethyl allyl urea solution, add 2g of pyridinediol enantiomer white solid, add 1g of pyridine solution, and put the solid in a water bath at 40°C under the protection of argon. Dissolve completely, remove the water bath, and drop to room temperature (20-25°C) under the protection of argon, the solution is calibrated as A1; then take a 50ml single-necked bottle, add 2g of phosphorus oxychloride solution, add 0.9g of acetonitrile solution, the solution Calibrated as A2. Under the protection of argon, add 3.5g of dimethyl allyl urea solution into a 50ml three-necked flask, stir and cool down to -25~-20℃, keep the temperature below -15℃, and slowly add dropwise A1 and A2 solutions, after the dropwise addition, keep warm at -25--20°C f...

Embodiment 2

[0072] 4-Amino-1-([5-O-(2S,4S)-2-oxyl-4-(4-pyridine)-1,3,2-dioxaphosphorin-2-yl]- Generation and preparation of β-D-arabinofuranosyl)-2(1H)-pyrimidinone (Formula 6) reference substance:

[0073]

[0074] The lyophilized preparation of cytarabine prodrug was placed in sodium chloride solution at room temperature for 30 days, the solid compound was dissolved in water and eluted with acetonitrile-water gradient, the largest peak after the main peak was collected, and concentrated Obtain target compound 0.5g, (C 17 h 21 N 4 o 8 P[M+H]:441.0,[M+Na]:463.0,[M+K]:478.9)

Embodiment 3

[0076] 1-([5-O-(2R,4S)-2-oxyl-4-(4-pyridine)-1,3,2-dioxaphosphorin-2yl]-β-D-arabinofuran base)-2,4(1H,3H)-pyrimidinedione (formula 7) generation and preparation of reference substance:

[0077]

[0078] In a 50mL three-neck flask, add 30g of dimethyl allyl urea solution, add 1.5g of pyridinediol white solid, add 1g of pyridine solution, under the protection of argon, dissolve the solid completely in a water bath at 35°C, remove Water bath, argon protection down to room temperature (20-25 ° C), the solution is calibrated as A1; then take a 50ml single-necked bottle, add 1.8g of phosphorus oxychloride solution, add 0.5g of acetonitrile, the solution is calibrated as A2. Under the protection of argon, add 3.5g of dimethyl propylene urea solution into a 50ml three-necked flask, stir and cool down to -25--20°C, keep the temperature below -15°C, and slowly add A1 and A2 solutions dropwise at the same time After the dropwise addition, keep warm at -25--20°C for 2h. Then, 1 g of ...

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Abstract

The invention provides a separated compound which is a cytarabine prodrug related substance. The invention also provides application of the compound, and the compound is used for preparing a cytarabine prodrug or a composition containing the cytarabine prodrug.

Description

technical field [0001] The invention belongs to the technical field of medicines, specifically, the invention relates to related substances of cytarabine prodrugs and applications thereof. Background technique [0002] Cytarabine prodrug is a targeting compound developed by HepdirectTM technology (see Chinese Patent No. 200380102686.5), which can be prepared by chemical synthesis and is mainly used to treat or prevent liver cancer and colorectal cancer expressing P450. Its chemical The structural formula is as follows: [0003] [0004] Chinese patent CN103393709B discloses a (drug) preparation containing cytarabine prodrug and a preparation method thereof. The pH of the solution is controlled between 3.5 and 4.1, and then freeze-dried. [0005] However, the inventors have found that the cytarabine prodrug has poor water solubility and contains phosphate and cytosine structures in its structure, which is easy to process during its (bulk drug) storage, transportation and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/048C07H19/11C07F9/6574C07D213/30C07D213/55G01N30/02G01N30/06G01N30/86
CPCC07H19/048C07H19/11C07F9/65742C07D213/30C07D213/55G01N30/02G01N30/06G01N30/8679G01N2030/062
Inventor 张艳侠张登科金伟丽黄青玲郭维博高中强
Owner XIAN XINTONG PHARM RES CO LTD
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