A solid dosage form of vascular endothelial growth factor inhibitor and its preparation method
A technology of solid dosage forms and growth factors, which can be applied in pill delivery, pharmaceutical formulations, medical preparations of non-active ingredients, etc., and can solve problems such as adverse reactions, mutant tumor signal transduction compensatory, drug resistance, etc.
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[0046] The preparation method of the 1,4-diaminonaphthalene derivative shown in formula (I) can comprise the following steps:
[0047] (a) making the compound shown in formula (1) carry out dealkylation reaction, obtain the compound shown in formula (2);
[0048] (b) making the compound shown in formula (2) carry out nucleophilic substitution reaction, obtain the compound shown in formula (3);
[0049] (c) In the presence of tert-butanol hydroperoxide and potassium hydroxide, a hydroxyl group is introduced into the compound shown in formula (3) to obtain a compound shown in formula (4);
[0050] (d) Substituting the compound shown in formula (4) to obtain the compound shown in formula (5);
[0051] (e) making the compound shown in formula (5) undergo an affinity substitution reaction with an amino substituent to obtain a compound shown in formula (6);
[0052] (f) making the compound shown in formula (6) undergo a hydrogenation reduction reaction to obtain the target compoun...
preparation example 1
[0079] (1) Preparation of 3-methoxy-5-nitro-2-naphthol
[0080]
[0081] Dissolve 6,7-dimethoxy-1-nitronaphthalene (4.66g, 20mmol) and L-methionine (2.98g, 20mmol) in 38.4g of methanesulfonic acid (400mmol), and reflux the oil bath at 90°C Stir the reaction under heating conditions for 8 hours, after TLC detects that the reaction is complete, neutralize the reaction with a saturated sodium bicarbonate solution until no bubbles emerge, the pH test paper detects that it is neutral or weakly alkaline, and then extract the aqueous phase 3 times with ethyl acetate, The ethyl acetate phases were combined, washed three times with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain a yellow powdery solid (1.18 g, yield: 27%).
[0082] (2) Preparation of 4-(3-((3-methoxy-5-nitronaphthalene-2-) oxygen) propyl) morpholine
[0083]
[0084] Dissolve 3-methoxy-5...
Embodiment 1
[0115]
[0116]
[0117] The compound 1, lactose monohydrate, microcrystalline cellulose, sodium carboxymethylcellulose and magnesium stearate were passed through a 100-mesh sieve. The sieved materials were placed in a three-dimensional mixer for total mixing, and the rotation speed of the three-dimensional mixer was 10 rpm for 15 minutes. The mixed materials were directly compressed into tablets or filled into capsules to prepare 100,000 units, each unit containing 20 mg of the compound 1.
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