Sustained-release analgesic compounds
A technology of compounds and pharmaceutical compounds, applied in the direction of non-central analgesics, anhydride/acid/halide active ingredients, drug combinations, etc., can solve problems such as unsatisfactory pain control
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Embodiment 1
[0131] Compound (1) of the present invention {morphine and 1 equivalent of naproxen} (scheme 1)
[0132] To a stirred suspension of morphine (50 mg, 0.175 mmol) in acetonitrile (3 ml) was added naproxen (44 mg, 0.192 mmol) followed by EDCI (37 mg, 0.192 mmol) under argon. ) and a catalytic amount of DMAP. The resulting cloudy mixture was stirred overnight at room temperature, then the solvent was removed under vacuum. The residue was dissolved in ethyl acetate and washed successively with water, sodium bicarbonate solution, water, brine, then dried over sodium sulfate. After evaporating the solvent, the crude product was purified using column chromatography on silica gel to obtain 45 mg of the present compound (1).
[0133] 1 H-NMR (CDCl 3 ), 1.65(d, 3H), 2.40(s, 3H), 3.88(s, 3H), 4.10(m, 2H), 4.85(d, 1H), 5.26(m, 1H), 5.74(m, 1H) , 6.55(d, 1H), 6.67(d, 1H), 7.12(m, 2H), 7.48(dd, 1H), 7.74(m, 3H).
Embodiment 2
[0135] Diesters (2) of compounds of the present invention {morphine and naproxen} (Scheme 1)
[0136] To a stirred suspension of morphine (89 mg) in acetonitrile (5 ml) under argon was added (180 mg, 2.5 eq) naproxen, to which was then added EDCI (150 mg, 2.5 eq) and a catalytic amount of DMAP. The reaction was carried out and the product was isolated as described in Example 1 to give the diester (2) of the compound of the invention (173 mg).
[0137] 1 H-NMR (CDCl 3 ), 1.58(d, 3H), 1.60(d, 3H), 2.41(s, 3H), 3.86(s, 3H), 3.88(s, 3H), 5.12(m, 2H), 5.36(m, 1H) , 5.54(m, 1H), 6.51(d, 1H), 6.60(d, 1H), 7.07(m, 4H), 7.44(m, 2H), 7.66(m, 6H).
Embodiment 3
[0139] Compound (4) of the present invention {diester of morphine and succinic acid} (Scheme 2)
[0140] Morphine (50 mg, 0.175 mmol) was dissolved in 1.5 ml of anhydrous pyridine at room temperature, and then DMAP (3 mg) was added to the solution. The reaction mixture was left at room temperature overnight, then it was evaporated to dryness. The crude residue containing the monoester (3) was co-evaporated with toluene to remove traces of pyridine and then dissolved in 3.5 ml dry acetonitrile. To this was added morphine (50 mg), followed by EDCI (34 mg, 0.175 mmol) and DMAP (2 mg). The reaction mixture was stirred overnight at room temperature, then it was evaporated to dryness. The residue was dissolved in ethyl acetate, washed with water, sodium bicarbonate solution, water and brine. Evaporation of the solvent left a crude product, which was purified by column chromatography to obtain 25 mg of the present compound (4) as a colorless foam.
[0141] 1 H-NMR (CDCl 3 ), 2....
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