Preparing methods of (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4 acetylaminoisoindoline 1,3-dione and its compound
A methanesulfonyl ethyl, methoxyphenyl technology, applied in the direction of drug combination, pharmaceutical formulation, organic active ingredients, etc., can solve the problem of lack of selectivity
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[0075] Preparation and storage of anhydrous pharmaceutical compositions should preserve their anhydrous nature. Accordingly, it is preferred that anhydrous compositions be packaged using materials known to be water repellent so that they can be packaged in suitable prescribed kits. Examples of suitable packaging include, but are not limited to, hermetically sealed foils, plastics, single-dose containers (eg, vials), blister packs, and split packs.
[0076] The present invention further includes pharmaceutical compositions and dosage forms containing one or more compounds that reduce the rate at which the active ingredient will decompose. These compounds, referred to herein as "stabilizers," include, but are not limited to, antioxidants such as ascorbic acid, pH buffers, or salt buffers.
[0077] As with the amount and type of excipients, the amount and specific type of active ingredient in the dosage form will vary depending on factors such as, but not limited to, the route o...
Embodiment 1
[0108] 5.1 Example 1: 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-4-acetylaminoisoindoline-1,3-dione Synthesis
[0109] 1-(3-Ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (1.0 g, 3.7 mmol) and 3-acetamidophthalic anhydride (751 mg, 3.66 mmol) in acetic acid (20 ml) was heated to reflux for 15 hours. The solvent was removed in vacuo to give an oil. The resulting oil was separated by chromatography to give the product (1.0 g, 59% yield) as a yellow solid, mp: 144°C.
[0110]1 H NMR (CDCl 3 )δ1.47(t, J=7.0Hz, 3H, CH 3 ), 2.26(s, 3H, CH 3 ), 2.88 (s, 3H, CH 3 ), 3.75(dd, J=4.4, 14.3Hz, 1H, CHH), 3.85(s, 3H, CH 3 ), 4.11(q, J=7Hz, 2H, CH2), 5.87(dd, J=4.3, 10.5Hz, 1H, NCH), 6.82-6.86(m, 1H, Ar), 7.09-7.11(m, 2H, Ar), 7.47(d, J=7Hz, 1H, Ar), 7.64(t, J=8Hz, 1H, Ar), 8.74(d, J=8Hz, 1H, Ar), 9.49(br s, 1H, NH); 13 C NMR (CDCl 3 )δ14.61,24.85,41.54,48.44,54.34,55.85,64.43,111.37,112.34,115.04,118.11,120.21,124.85,129.17,130.96,136.01,137.52,148.54,149.65,167...
Embodiment 2
[0112] 5.2 Example 2: (+) 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3 - Synthesis of diketones
[0113] Preparation of 3-aminophthalic acid
[0114] Palladium on carbon (10%, 2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were added to a 2.5 L Parr hydrogenator under nitrogen atmosphere. Hydrogen was bubbled into the reaction vessel to a pressure of 55 psi. The mixture was shaken for 13 hours maintaining a hydrogen pressure between 50-55 psi. The hydrogen was vented and the mixture was purged 3 times with nitrogen. The suspension was filtered through a bed of Celite and washed with methanol. The filtrate was concentrated under vacuum. The resulting solid was reslurried with ether and isolated by vacuum filtration. The solid was vacuum dried to constant weight to obtain 54 g (84% yield) of 3-aminophthalic acid as a yellow solid.
[0115] 1 H-NMR (DMSO-d6) δ: 3.17 (s, 2H), 6.67 (d, 1H), 6.82 (d, 1H), 7.17 (t, 1...
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