PT2263669E - Derivados de isoindolina farmaceuticamente activos - Google Patents

Info

Publication number

PT2263669E

PT2263669E PT10176420T PT10176420T PT2263669E PT 2263669 E PT2263669 E PT 2263669E PT 10176420 T PT10176420 T PT 10176420T PT 10176420 T PT10176420 T PT 10176420T PT 2263669 E PT2263669 E PT 2263669E

Authority

PT

Portugal

Prior art keywords

ethoxy

methoxyphenyl

mmol

carbon atoms

mixture

Prior art date

1999-11-12

Links

• Espacenet
• Global Dossier
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• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title description 5
• QDZOBXFRIVOQBR-LJQANCHMSA-N n-[2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 QDZOBXFRIVOQBR-LJQANCHMSA-N 0.000 claims abstract description 17
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 13
• 239000002253 acid Substances 0.000 claims abstract description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 8
• 238000011282 treatment Methods 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 10
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
• 208000024908 graft versus host disease Diseases 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 5
• 125000002345 steroid group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 210
• 125000004432 carbon atom Chemical group C* 0.000 description 150
• 239000007787 solid Substances 0.000 description 150
• 239000000203 mixture Substances 0.000 description 149
• 238000005481 NMR spectroscopy Methods 0.000 description 133
• -1 Z is - NR 6 'R 7' Chemical group 0.000 description 100
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
• 150000001875 compounds Chemical class 0.000 description 86
• 235000019439 ethyl acetate Nutrition 0.000 description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• 239000003921 oil Substances 0.000 description 68
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
• 229910001868 water Inorganic materials 0.000 description 63
• 239000000725 suspension Substances 0.000 description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 57
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
• 239000002904 solvent Substances 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• 125000000217 alkyl group Chemical group 0.000 description 50
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
• 229910052739 hydrogen Inorganic materials 0.000 description 43
• 239000012267 brine Substances 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 239000001257 hydrogen Substances 0.000 description 40
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 33
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• 239000000243 solution Substances 0.000 description 32
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
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• 125000005843 halogen group Chemical group 0.000 description 14
• 150000002431 hydrogen Chemical class 0.000 description 14
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• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• BHJUWEUNUCJYER-UHFFFAOYSA-N 4-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(N)C=CC=C3C2=O)=O)=C1 BHJUWEUNUCJYER-UHFFFAOYSA-N 0.000 description 11
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