Artemisinin-base combination compound or pharmaceutically acceptable salt thereof, pharmaceutical preparation and application
A compound and artemisinin technology, applied in the field of medicine, can solve the problems of significant toxic and side effects, and achieve the effects of good drug resistance, good anti-tumor activity, and low toxic and side effects
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[0066] Artemisinin - Preparation of base The main reaction was split programs are:
[0067]
[0068] Means Het Het as defined hereinbefore 1 Or Het 2 ;
[0069]
[0070] Wherein, BF 3 · Et 2 O is boron trifluoride diethyl ether, TFA is trifluoroacetic acid, Het 1 As hereinbefore defined;
[0071]
[0072] DIAD is diisopropyl azodicarboxylate, TPP is triphenylphosphine, X is as hereinbefore defined.
Example Embodiment
[0073] Example 1: 10-O- [2- (9H-9- purin-yl) - ethyl] - Preparation of dihydroartemisinin - (10S)
[0074] Step A: 10-O- (2- bromo-ethyl) - (10S) - Preparation of dihydroartemisinin
[0075]
[0076] Lower 5g (17.6mmol) dihydroartemisinin (DHA) and 1.25mL (17.6mmol) 2- bromoethanol was dissolved in 100mL purified THF (tetrahydrofuran) in a nitrogen atmosphere, an ice bath was slowly added dropwise 3.5mL (0.50g , 3.5mmol) of boron trifluoride diethyl ether (BF 3 · Et 2 O), the reaction was stirred for 6 hours. The reaction by TLC (ethyl acetate: petroleum ether = 1: 4) monitoring. After completion of the reaction, saturated NaHCO 3 Solution. The organic layer was collected delamination, the aqueous layer (25mL × 2) separated and extracted with ethyl acetate, and the combined organic layers. The organic layer was washed with 20mL saturated saline solution, then dried over anhydrous Na 2 SO 4 Sulfate, and the solvent was removed by distillation under reduced pressure a crude produc...
Example Embodiment
[0082] Example 2: 10-O- [2- (6- Amino-purin--9H-9- yl) - ethyl] - Preparation of dihydroartemisinin - (10S)
[0083] Prepared according to Example 1, the raw material instead of an adenine The title compound was prepared in Example 1 starting material 9H- purin embodiment;
[0084] LC-MS (m / z): 446.2 [M + H] +
[0085] 1 H NMR (CDCL 3 , Δ (ppm)): δ8.34 (s, 1H, Pur-H), 7.88 (s, 1H, Pur-H), 6.26 (s, 2H, -NH 2 ), 5.01 (s, 1H, H-12), 4.77 (d, J = 3.5Hz, 1H, H-10), 4.59-4.46 (m, 1H, -OCH 2 C H 2 -), 4.41-4.24 (m, 2H, -OC H 2 C H 2 -), 3.76 (ddd, J = 10.2,6.5,3.6Hz, 1H, -OC H 2 CH 2 -), 2.63-2.57 (m, 1H, H-9), 2.38-2.30 (m, 1H, H-4), 1.42 (s, 3H, H-14), 0.94 (d, J = 6.2Hz, 3H , H-16), 0.80 (d, J = 7.4Hz, 3H, H-15).
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