Conjugate based systems for controlled drug delivery
A technology of conjugates and drugs, applied in the directions of drug combinations, endocrine system diseases, active ingredients of heterocyclic compounds, etc.
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Embodiment 1
[0486] Example 1-Synthesis of Azido Ethyl Glucose (AzEG)
[0487] a. Synthesis of bromoethyl glucose
[0488] Wash DOWEX 50Wx4 resin (Alfa Aesar, Ward Hill, MA) with deionized water to remove color. Use 2.2 L 2-bromoethanol (30.5 mol, 25 equivalents; 124.97 g / mol; 1.762 g / mL; BP = 150°C; Alfa Aesar) to treat 225 grams of D-glucose (1.25 mol; 1 equivalent, Alfa Aesar) and 140 G DOWEX 50Wx4 mixture, and heat the stirred mixture to 80°C for 4 hours. The reaction was monitored by TLC (20% methanol / dichloromethane (DCM)). After about 4 hours, the reaction was over and it was cooled to room temperature. The solution was filtered to remove the resin, and the resin was washed with ethyl acetate and DCM. The filtrate obtained was stripped into an amber oil in a rotary evaporator. A total of 400 g was obtained after evaporation.
[0489] The amber oil was purified on silica gel (4 kg silica, packaged in DCM) in the following manner. The crude product was dissolved in DCM and loaded ont...
Embodiment 2
[0495] Example 2-Synthesis of Azido Ethyl Mannose (AzEM)
[0496] a. Synthesis of bromoethylmannose
[0497] Wash DOWEX 50Wx4 resin (Alfa Aesar, Ward Hill, MA) with deionized water to remove color. Use 2.2 L 2-bromoethanol (30.5 mol, 25 equivalents; 124.97 g / mol; 1.762 g / mL; BP = 150°C; Alfa Aesar) to treat 225 grams of D-mannose (1.25 mol; 1 equivalent, Alfa Aesar) and 140 grams of a mixture of DOWEX 50Wx4, and the stirred mixture was heated to 80°C for 4 hours. The reaction was monitored by TLC (20% methanol / dichloromethane (DCM)). After about 4 hours, the reaction was complete and then cooled to room temperature. The solution was filtered to remove the resin, and the resin was washed with ethyl acetate and DCM. The filtrate obtained was evaporated to an amber oil in a rotary evaporator.
[0498] The amber oil was purified on silica gel (4 kg silica, packaged in DCM) in the following manner. The crude product was dissolved in DCM and loaded onto the column, then eluted with ...
Embodiment 3
[0504] Example 3-Synthesis of Azido Ethyl Mannobiose (AzEBM)
[0505] Using phthalic ether, the AzEM compound from Example 2 was selectively protected, purified by column chromatography, and then reacted with benzyl bromide to obtain 1-α-(2-azidoethyl)-4,6- Benzaldehyde diacetal-3-benzyl-mannopyranoside. Then use the silver triflate chemical method, under strict anhydrous conditions, use 1-α-bromo-2,3,4,6-tetrabenzoyl mannopyranoside, glycosylation product, to obtain the Protected-azidoethyl mannobiose product. The intermediate product is then deprotected to remove the benzoyl group to obtain AzEBM.
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