Compounds with anti-inflammatory activity
A compound and ester sub-technology, applied in the field of macrolide complexes with anti-inflammatory activity, can solve the problems of no related reports
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[0068] The acid addition salts of said basic compounds are prepared by bringing the free base form into contact with a sufficient amount of the desired acid to prepare the corresponding salt by conventional methods. The free base form can be recovered by contacting the corresponding salt with a base and isolated by conventional methods. The free base forms differ from their corresponding salts in certain physical properties, such as solubility in polar solvents, but these salts are equivalent to the corresponding free bases for the purposes of the present invention.
[0069] Pharmaceutically acceptable base addition salts can be formed with metals or amines, such as alkali and alkaline earth metals or organic amines. Examples of metals used as cations are sodium, potassium, magnesium, calcium and the like. Examples of suitable amines are N,N'-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, dicyclohexylamine, ethylenediamine, N-methylglucamine and procaine C...
Embodiment 1
[0206] Compound 1: (I; M=M4, D=D1)
[0207]
[0208] Compound D1 (825 mg; 2.18 mmol) was dissolved in 15 mL of dry dichloromethane under argon flow. Subsequently, 2.86 mL of triethylamine, 601 mg of hydroxybenzotriazole, 1.82 g of macrolide M4 (2.18 mmol) and 3.1 g of 1-(3-dimethylaminopropyl)-3 were added to the solution -Ethylcarbodiimide hydrochloride. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. The resulting mixture was purified by silica gel column, eluent was CHCl 3 :MeOH:NH 4 OH=6:1:0.1. 1.44 g of compound 1 was obtained; MS (m / z): 837.5 [MH] + . IR(KBr)cm -1 : 3422, 2938, 2874, 1710, 1663, 1624, 1560, 1528, 1458, 1376, 1302, 1245, 1176, 1139, 1089, 1052, 1036, 1012, 959, 929, 894, 816, 754, 706, 669 .
Embodiment 2
[0210] Compound 2: (I; M=M4, D=D5)
[0211]
[0212] Compound D5 (57.8 mg; 0.16 mmol) was dissolved in 5 mL of dry dichloromethane under argon flow. Add 0.209 mL of triethylamine to the solution to clarify the solution. Subsequently, 43.9 mg of hydroxybenzotriazole, macrolide M4 (76 mg, 0.1595 mmol) and 129.2 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added . The reaction mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure. The resulting mixture was purified by silica gel column, eluent was CHCl 3 :MeOH:NH 4 OH=6:1:0.1. Obtained 32 mg of compound 2; MS (m / z): 821.4 [MH] + IR(KBr)cm -1 : 3423, 2939, 2876, 1718, 1664, 1625, 1560, 1541, 1458, 1376, 1353, 1296, 1249, 1178, 1089, 1054, 975, 959, 928, 889, 828, 811, 750, 669.
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