Polyethylene glycol derivatives of activated lactone compounds
A technology of PEGylation and compounding, which is applied in the field of active lactone compounds, and can solve problems such as the influence of drug stability
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Embodiment 1
[0039] Example 1 Using penhuning as the starting material to prepare single-site mPEG of dehydroandrographolide disuccinic acid half ester 1100 derivative.
[0040]
[0041] Weigh 2.85g (5mmol) of Chuanhuning and place it in a 500ml reaction bottle, add a mixed solution of 125ml ethanol and 175ml water, after the solid dissolves, add 5.0ml of 1M HC1 aqueous solution dropwise under ice bath conditions, and stir for 10 minutes after the addition is completed. minutes, room temperature (25 ° C) rotary evaporation to remove a large amount of ethanol, extracted with ethyl acetate, dried with anhydrous sodium sulfate, rotary evaporation to remove the solvent, quantitatively obtained dehydroandrographolide disuccinic acid half ester 2.60g.
[0042] Dissolve 2.6g (5mmol) dehydroandrographolide disuccinic acid half ester in 100ml DCM, add 1.95g EDC·HCl (10mmol) to dissolve, stir for 10 minutes, then add 8.25gmPEG 1100 (7.5 mmol). Under ice-bath conditions, 0.061 g DMAP (0.5 mmol) ...
Embodiment 2
[0043] Example 2 Using dehydroandrographolide disuccinate half ester as a starting material to prepare single-site mPEG of dehydroandrographolide disuccinate half ester 1100 derivative.
[0044] Dissolve 2.53g (5mmol) dehydroandrographolide disuccinic acid half ester in 100ml DCM, add 1.95g EDC·HCl (10mmol) to dissolve, stir for 10 minutes, then add 8.25gmPEG 1100 (7.5 mmol). Under ice-bath conditions, 0.061 g DMAP (0.5 mmol) was added. After reacting for 5 hours, after the completion of the reaction was monitored by HPLC, the reaction solution was concentrated and subjected to silica gel column chromatography to obtain a light yellow oily liquid, and a white solid was precipitated with anhydrous ether to obtain 4.42 g of the product, with a yield of 54.2%.
Embodiment 3
[0045] Example 3 Preparation of double-site mPEG of dehydroandrographolide disuccinic acid half-ester using penhuning as starting material 1100 derivative.
[0046]
[0047] Weigh 2.85g (5mmol) of Chuanhuning and place it in a 500ml reaction bottle, add a mixed solution of 125ml ethanol and 175ml water, after the solid dissolves, add 5.0ml 1M aqueous HCl solution dropwise under ice bath conditions, and stir for 10 minutes after the addition is completed. minutes, room temperature (25 ° C) rotary evaporation to remove a large amount of ethanol, extracted with ethyl acetate, dried with anhydrous sodium sulfate, rotary evaporation to remove the solvent, quantitatively obtained dehydroandrographolide disuccinic acid half ester 2.60g.
[0048] Dissolve 2.6g (5mmol) dehydroandrographolide disuccinic acid half ester in 100ml DCM, add 2.14g EDC·HCl (11mmol) to dissolve, stir for 10 minutes, then add 12.12g mPEG 1100 (11 mmol). Under ice-bath conditions, 0.061 g DMAP (0.5 mmol) wa...
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