Conjugates of saturated aliphatic chain alcohol, dexamethasone, and His-Gly-Glu, preparation, nano structure, and applications thereof
A technology of -his-gly-glu and dexamethasone, applied in the field of research on ear swelling caused by 10a-f p-xylene in mice, can solve the side effects of osteoporosis, the limitations of treatment objects and regimens, and strong toxic and side effects and other problems, to achieve wide application prospects and excellent immunosuppressive effects
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Embodiment 1
[0032] Embodiment 1 prepares dexamethasone 3-carboxypropionate (1)
[0033] 3.93g (10mmol) dexamethasone and 1.3g (13mmol) succinic anhydride reacted in the dark in 150ml tetrahydrofuran (THF) in the presence of 1.46g (12mmol) 4-dimethylaminopyridine (DMAP) for 48 hours, TLC ( CH 2 Cl 2 :CH 3 OH:HOAC, 20:1:0.15) showed complete disappearance of starting material. Add 30ml H to the reaction mixture 2 O, concentrated under reduced pressure, the residue was added KHSO 4 The pH was adjusted to 2, and the precipitated colorless powder was washed with acetone / petroleum ether to obtain 4.64 g (94%) of the title compound as a colorless powder. ES I / MS(m / z)491[M-H] - . 1 H NMR (300MHZ, DMSO-d6): δ / ppm=7.29(d, J=10.2Hz, 1H), 6.23(d, J=9.3Hz, 1H), 6.01(s, 1H), 5.42(s, 1H ), 5.17(s, 1H), 5.05(d, J=17.7Hz, 1H), 4.80(d, J=17.7Hz, 1H), 4.15(m, 1H), 2.88(m, 1H), 2.52(m , 2H), 2.61(m, 3H), 2.34(m, 2H), 2.15(m, 2H), 1.77(m, 1H), 1.61(m, 2H), 1.49(s, 3H), 1.35(m, 1H), 1.08 (m, 1H), 0.8...
Embodiment 2
[0034] Embodiment 2 prepares dexamethasone 3-N-formylsuccinimidyl propionate (2)
[0035] 4.92g (10mmol) dexamethasone succinate (1) was present in 2.50g (13mmol) 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (HCl·EDC) Under reaction with 1.50g (13mmol) N-hydroxysuccinimide (HOSu) in the solvent of 100ml THF and 10ml DMF dark reaction 24 hours, TLC (CH 2 Cl 2 :CH 3 OH:HOAC, 30:1:0.15) showed complete disappearance of starting material. The reaction mixture was concentrated under reduced pressure, 150ml of ethyl acetate was added to the residue, and the resulting solution was washed with 20ml of saturated NaHCO 3 Wash 3 times with aqueous solution, wash 2 times with 20ml saturated NaCl aqueous solution, wash with 20ml saturated KHSO 4 The aqueous solution was washed 3 times, then washed 2 times with 20ml saturated NaCl aqueous solution, the ethyl acetate layer was dried with anhydrous sodium sulfate, filtered, the filtrate was concentrated to dryness under reduc...
Embodiment 3
[0036] Example 3 Preparation of Boc-Glu(OBzl)-O-(CH 2 ) 7 CH 3 (3a)
[0037] Dissolve 1.49g (5mmol) Boc-Glu (OBzl) in 20mL of anhydrous THF, add 0.675g (5mmol) N-hydroxybenzotriazole (HO Bt) to the resulting solution under ice-cooling, and make it completely dissolve. After 10 minutes, 1.236 g (6 mmol) of dicyclohexylcarbodiimide (DCC) was added to obtain reaction solution I. Put 0.78g (6mmol) CH in ice bath 3 (CH 2 ) 7 OH was suspended in 20 mL of anhydrous dichloromethane, and then 1 mL of N-methylmorpholine (NMM) was added to adjust the pH to 9. Stir for 35 minutes to obtain reaction solution II. The reaction solution I was added to the reaction solution II under ice-cooling, first stirred under ice-cooling for 1 h, and then stirred at room temperature for 12 h, TLC (ethyl acetate:petroleum ether, 2:1) showed that Boc-Gly disappeared. Dicyclohexylurea (DCU) was filtered off and concentrated under reduced pressure. The residue was dissolved with 50 mL of ethyl acet...
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