Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use thereof
A kind of composition, the technology of medicine, is applied in the prodrug of methyl hydrogen fumarate, its pharmaceutical composition, and its use field, can solve problems such as poor water solubility
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Embodiment 1
[0480] (N,N-Diethylcarbamoyl)methylmethyl(2E)but-2-ene-1,4-dioate (1)
[0481]
[0482] According to General Procedure A, methyl hydrogen fumarate (MHF) (0.39 g, 3.00 mmol) dissolved in NMP was mixed with 2-chloro-N,N-diethylacetamide (0.44 g, 3.00 mmol) at about 55 °C ) in CsHCO 3 (0.69 g, 3.60 mmol) gave 0.37 g ( 51% yield) of the title compound (1). M.p.: 53-56°C. 1 H NMR (CDCl 3 , 400MHz): δ6.99-6.90(m, 2H), 4.83(s, 2H), 3.80(s, 3H), 3.39(q, J=7.2Hz, 2H), 3.26(q, J=7.2Hz, 2H), 1.24(t, J=7.2Hz, 3H), 1.14(t, J=7.2Hz, 3H). MS(ESI):m / z244.13(M+H) + .
Embodiment 2
[0484] Methyl[N-benzylcarbamoyl]methyl(2E)but-2-ene-1,4-dioate (2)
[0485]
[0486] According to General Procedure A, methyl hydrogen fumarate (MHF) (0.50 g, 3.85 mmol) dissolved in NMP was mixed with N-benzylchloroacetamide (0.84 g, 4.61 mmol) in CsHCO at about 55 °C. 3 Reaction in the presence of (0.89 g, 4.61 mmol) afforded 0.56 g (53% yield) of the title compound (2) as a white solid after purification by mass-directed preparative HPLC and lyophilization. 1 H NMR (CDCl 3 , 400MHz): δ7.36-7.26(m, 5H), 6.94-6.88(m, 2H), 6.19(br s, 1H), 4.73(s, 2H), 4.51(d, J=5.6Hz, 2H) , 3.81(s, 3H). MS(ESI): m / z 278.04(M+H) + .
Embodiment 3
[0488] Methyl 2-morpholin-4-yl-2-oxoethyl(2E)but-2-ene-1,4-dioate (3)
[0489]
[0490] According to General Procedure A, methyl hydrogen fumarate (MHF) (0.50 g, 3.84 mmol) dissolved in NMP was mixed with 4-(chloroacetyl)morpholine (0.75 g, 4.61 mmol) in CsHCO at about 55 °C. 3 Reaction in the presence of (0.89 g, 4.61 mmol) afforded 0.34 g (35% yield) of the title compound (3) as a white solid after purification by mass-directed preparative HPLC and lyophilization. M.p.: 124-126°C; 1 H NMR (CDCl 3 , 400MHz): δ6.97-6.91(m, 2H), 4.84(s, 2H), 3.82(s, 3H), 3.72-3.70(m, 4H), 3.64-3.62(m, 2H), 3.46-3.41 (m, 2H). MS(ESI): m / z 258.04(M+H) + .
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