CA2392081C - Pharmaceutically active isoindoline derivatives - Google Patents
Pharmaceutically active isoindoline derivatives Download PDFInfo
- Publication number
- CA2392081C CA2392081C CA002392081A CA2392081A CA2392081C CA 2392081 C CA2392081 C CA 2392081C CA 002392081 A CA002392081 A CA 002392081A CA 2392081 A CA2392081 A CA 2392081A CA 2392081 C CA2392081 C CA 2392081C
- Authority
- CA
- Canada
- Prior art keywords
- methoxyphenyl
- ethoxy
- alkyl
- amino
- dioxoisoindolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 201000010099 disease Diseases 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 18
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 142
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 98
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 97
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- -1 imidazoyl Chemical group 0.000 claims description 80
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000003282 alkyl amino group Chemical group 0.000 claims description 61
- 125000001589 carboacyl group Chemical group 0.000 claims description 53
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 51
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 40
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 39
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 21
- 125000001425 triazolyl group Chemical group 0.000 claims description 21
- 125000001118 alkylidene group Chemical group 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- 230000033115 angiogenesis Effects 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 208000030507 AIDS Diseases 0.000 claims description 10
- QKHSAVPFILQVGW-UHFFFAOYSA-N 4,5-diamino-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(N)=CC=C3C2=O)=O)=C1 QKHSAVPFILQVGW-UHFFFAOYSA-N 0.000 claims description 9
- VAZPGDVTTOAULR-UHFFFAOYSA-N 3-[4-[[2-(dimethylamino)acetyl]amino]-1,3-dioxoisoindol-2-yl]-3-(3-ethoxy-4-methoxyphenyl)-n,n-dimethylpropanamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(=O)CN(C)C)C=CC=C3C2=O)=O)=C1 VAZPGDVTTOAULR-UHFFFAOYSA-N 0.000 claims description 8
- HEWRXBRDIAUSKW-UHFFFAOYSA-N 4-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(N)C=CC=C3C2=O)=O)=C1 HEWRXBRDIAUSKW-UHFFFAOYSA-N 0.000 claims description 7
- 206010006895 Cachexia Diseases 0.000 claims description 7
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- MQRUNQYIJQXVLP-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 MQRUNQYIJQXVLP-UHFFFAOYSA-N 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- OXYAFFHMEHZDGM-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4,5-dinitroisoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(C(=CC=C3C2=O)[N+]([O-])=O)[N+]([O-])=O)=O)=C1 OXYAFFHMEHZDGM-UHFFFAOYSA-N 0.000 claims description 6
- AUYSFUSWFJUKMJ-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-4-(1h-pyrrol-2-yl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(C=4NC=CC=4)C=CC=C3C2=O)=O)=C1 AUYSFUSWFJUKMJ-UHFFFAOYSA-N 0.000 claims description 6
- VEXOSRQHSWXFDL-UHFFFAOYSA-N 3-[1,3-dioxo-4-(1h-pyrrol-2-yl)isoindol-2-yl]-3-(3-ethoxy-4-methoxyphenyl)-n,n-dimethylpropanamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(C=4NC=CC=4)C=CC=C3C2=O)=O)=C1 VEXOSRQHSWXFDL-UHFFFAOYSA-N 0.000 claims description 6
- CEUCTMSNRQZUSX-UHFFFAOYSA-N 4-(aminomethyl)-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(CN)C=CC=C3C2=O)=O)=C1 CEUCTMSNRQZUSX-UHFFFAOYSA-N 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
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- 206010003246 arthritis Diseases 0.000 claims description 6
- HHSCRXUCPLPVQX-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 HHSCRXUCPLPVQX-UHFFFAOYSA-N 0.000 claims description 6
- ISPUPFYJUWLMEH-CAWMZFRYSA-N 2-[(1r)-1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]-4-(1h-pyrrol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(C)O)N2C(C3=C(CC=4NC=CC=4)C=CC=C3C2=O)=O)=C1 ISPUPFYJUWLMEH-CAWMZFRYSA-N 0.000 claims description 5
- ZOMMYBFPBGWUAT-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(1h-imidazol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CC=4NC=CN=4)C=CC=C3C2=O)=O)=C1 ZOMMYBFPBGWUAT-UHFFFAOYSA-N 0.000 claims description 5
- LXFIMHZDTHLHOA-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(1h-pyrrol-2-yl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(C=4NC=CC=4)C=CC=C3C2=O)=O)=C1 LXFIMHZDTHLHOA-UHFFFAOYSA-N 0.000 claims description 5
- HPNGOUOSHMENJP-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(1h-pyrrol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CC=4NC=CC=4)C=CC=C3C2=O)=O)=C1 HPNGOUOSHMENJP-UHFFFAOYSA-N 0.000 claims description 5
- KYBGGKMHMYDTDS-UHFFFAOYSA-N 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(5-methyl-1,3,4-oxadiazol-2-yl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(C=4OC(C)=NN=4)C=CC=C3C2=O)=O)=C1 KYBGGKMHMYDTDS-UHFFFAOYSA-N 0.000 claims description 5
- FFOXNTUNASQTMG-UHFFFAOYSA-N 2-amino-n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)CN)C=CC=C3C2=O)=O)=C1 FFOXNTUNASQTMG-UHFFFAOYSA-N 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
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- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- YERMOCFDEPTPGV-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(N(S(C)(=O)=O)S(C)(=O)=O)C=CC=C3C2=O)=O)=C1 YERMOCFDEPTPGV-UHFFFAOYSA-N 0.000 claims description 5
- QDZOBXFRIVOQBR-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 QDZOBXFRIVOQBR-UHFFFAOYSA-N 0.000 claims description 5
- KIRMTFBOUGUJOQ-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxypentyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(O)CC)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 KIRMTFBOUGUJOQ-UHFFFAOYSA-N 0.000 claims description 5
- JGGSUUSWFUVOKY-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxopentyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(=O)CC)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 JGGSUUSWFUVOKY-UHFFFAOYSA-N 0.000 claims description 5
- GNDMDNGVKFJTQD-UHFFFAOYSA-N n-[[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]methyl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CNC(C)=O)C=CC=C3C2=O)=O)=C1 GNDMDNGVKFJTQD-UHFFFAOYSA-N 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- HHZHPBGFUBYKRN-UHFFFAOYSA-N 2-(dimethylamino)-n-[[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]methyl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CNC(=O)CN(C)C)C=CC=C3C2=O)=O)=C1 HHZHPBGFUBYKRN-UHFFFAOYSA-N 0.000 claims description 4
- NAKSEFFBNWKUJH-OAQYLSRUSA-N 2-[(1r)-1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-4-(1h-pyrrol-2-ylmethyl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(C)=O)N2C(C3=C(CC=4NC=CC=4)C=CC=C3C2=O)=O)=C1 NAKSEFFBNWKUJH-OAQYLSRUSA-N 0.000 claims description 4
- KVBKXXOHQDLRLG-UHFFFAOYSA-N 2-chloro-n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)CCl)C=CC=C3C2=O)=O)=C1 KVBKXXOHQDLRLG-UHFFFAOYSA-N 0.000 claims description 4
- ISODCLUTRNLGQU-UHFFFAOYSA-N 2-chloro-n-[[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]methyl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CNC(=O)CCl)C=CC=C3C2=O)=O)=C1 ISODCLUTRNLGQU-UHFFFAOYSA-N 0.000 claims description 4
- RKODPUVUBAWGBM-UHFFFAOYSA-N 3-(dimethylamino)-n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]propanamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)CCN(C)C)C=CC=C3C2=O)=O)=C1 RKODPUVUBAWGBM-UHFFFAOYSA-N 0.000 claims description 4
- XVVPUIFFCFFMBS-UHFFFAOYSA-N C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CONC=O)C=CC=C3C2=O)=O)=C1 Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(CONC=O)C=CC=C3C2=O)=O)=C1 XVVPUIFFCFFMBS-UHFFFAOYSA-N 0.000 claims description 4
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- QDZOBXFRIVOQBR-IBGZPJMESA-N n-[2-[(1r)-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-IBGZPJMESA-N 0.000 claims description 4
- XCCGODHJXOPFSU-HXUWFJFHSA-N n-[2-[(1r)-3-(dimethylamino)-1-(3-ethoxy-4-methoxyphenyl)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(=O)N(C)C)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 XCCGODHJXOPFSU-HXUWFJFHSA-N 0.000 claims description 4
- REHJAEDOIKWMDG-UHFFFAOYSA-N n-[2-[1-(3,4-dimethoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(C)=O)N1C(=O)C2=C(N(S(C)(=O)=O)S(C)(=O)=O)C=CC=C2C1=O REHJAEDOIKWMDG-UHFFFAOYSA-N 0.000 claims description 4
- MVFSISZBKOLEKN-UHFFFAOYSA-N n-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound COC1=CC=C(C(CC(C)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)C=C1OC1CCCC1 MVFSISZBKOLEKN-UHFFFAOYSA-N 0.000 claims description 4
- HTMFPTFPZHDRKM-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]-2,2,2-trifluoroacetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C(F)(F)F)C=CC=C3C2=O)=O)=C1 HTMFPTFPZHDRKM-UHFFFAOYSA-N 0.000 claims description 4
- UXIXMIGOPYWHCQ-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]methanesulfonamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NS(C)(=O)=O)C=CC=C3C2=O)=O)=C1 UXIXMIGOPYWHCQ-UHFFFAOYSA-N 0.000 claims description 4
- BFESEYUXGQAUDS-LJQANCHMSA-N (3r)-3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-(3-ethoxy-4-methoxyphenyl)-n,n-dimethylpropanamide Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(=O)N(C)C)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 BFESEYUXGQAUDS-LJQANCHMSA-N 0.000 claims description 3
- VAZPGDVTTOAULR-LJQANCHMSA-N (3r)-3-[4-[[2-(dimethylamino)acetyl]amino]-1,3-dioxoisoindol-2-yl]-3-(3-ethoxy-4-methoxyphenyl)-n,n-dimethylpropanamide Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(=O)N(C)C)N2C(C3=C(NC(=O)CN(C)C)C=CC=C3C2=O)=O)=C1 VAZPGDVTTOAULR-LJQANCHMSA-N 0.000 claims description 3
- AUVWUWFCGQNERQ-UHFFFAOYSA-N 2-[1-(3,4-dimethoxyphenyl)-2-methylsulfonylethyl]-4-(1h-pyrrol-2-yl)isoindole-1,3-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(CS(C)(=O)=O)N1C(=O)C2=C(C=3NC=CC=3)C=CC=C2C1=O AUVWUWFCGQNERQ-UHFFFAOYSA-N 0.000 claims description 3
- RREPAJHHRAPCQP-UHFFFAOYSA-N 2-chloro-n-[2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CC(C)=O)N2C(C3=C(NC(=O)CCl)C=CC=C3C2=O)=O)=C1 RREPAJHHRAPCQP-UHFFFAOYSA-N 0.000 claims description 3
- JSLPDEPKIWZVKP-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-1h-pyrrol-2-yl]-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(C4=C(C=CN4)CN(C)C)C=CC=C3C2=O)=O)=C1 JSLPDEPKIWZVKP-UHFFFAOYSA-N 0.000 claims description 3
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- 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 description 3
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- CZVNIGALSIBARE-GOSISDBHSA-N n-[2-[(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-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)=O)=C1 CZVNIGALSIBARE-GOSISDBHSA-N 0.000 claims description 2
- CZVNIGALSIBARE-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2=O)=O)=C1 CZVNIGALSIBARE-UHFFFAOYSA-N 0.000 claims description 2
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Applications Claiming Priority (7)
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| US16516899P | 1999-11-12 | 1999-11-12 | |
| US60/165,168 | 1999-11-12 | ||
| US59034400A | 2000-06-08 | 2000-06-08 | |
| US09/590,344 | 2000-06-08 | ||
| US09/708,199 | 2000-11-08 | ||
| US09/708,199 US6667316B1 (en) | 1999-11-12 | 2000-11-08 | Pharmaceutically active isoindoline derivatives |
| PCT/US2000/030770 WO2001034606A1 (en) | 1999-11-12 | 2000-11-09 | Pharmaceutically active isoindoline derivatives |
Publications (2)
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| CA2392081A1 CA2392081A1 (en) | 2001-05-17 |
| CA2392081C true CA2392081C (en) | 2010-01-05 |
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| CA002392081A Expired - Fee Related CA2392081C (en) | 1999-11-12 | 2000-11-09 | Pharmaceutically active isoindoline derivatives |
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-
2000
- 2000-11-08 US US09/708,199 patent/US6667316B1/en not_active Expired - Lifetime
- 2000-11-09 CN CNB00818254XA patent/CN1325497C/zh not_active Expired - Fee Related
- 2000-11-09 ES ES00977095T patent/ES2282147T3/es not_active Expired - Lifetime
- 2000-11-09 AT AT06009632T patent/ATE506058T1/de not_active IP Right Cessation
- 2000-11-09 EP EP00977095A patent/EP1228071B8/en not_active Expired - Lifetime
- 2000-11-09 MX MXPA02004793A patent/MXPA02004793A/es active IP Right Grant
- 2000-11-09 ES ES06009632T patent/ES2363933T3/es not_active Expired - Lifetime
- 2000-11-09 ES ES10176420T patent/ES2380574T3/es not_active Expired - Lifetime
- 2000-11-09 EP EP10176420A patent/EP2263669B1/en not_active Expired - Lifetime
- 2000-11-09 DK DK00977095T patent/DK1228071T3/da active
- 2000-11-09 CA CA002392081A patent/CA2392081C/en not_active Expired - Fee Related
- 2000-11-09 NZ NZ519459A patent/NZ519459A/en not_active IP Right Cessation
- 2000-11-09 JP JP2001536553A patent/JP5116201B2/ja not_active Expired - Fee Related
- 2000-11-09 DE DE60034139T patent/DE60034139T2/de not_active Expired - Lifetime
- 2000-11-09 AU AU14780/01A patent/AU782409B2/en not_active Ceased
- 2000-11-09 DK DK10176420.7T patent/DK2263669T3/da active
- 2000-11-09 AT AT10176390T patent/ATE544451T1/de active
- 2000-11-09 AT AT00977095T patent/ATE357913T1/de active
- 2000-11-09 EP EP10176390A patent/EP2255801B1/en not_active Expired - Lifetime
- 2000-11-09 SI SI200030951T patent/SI1228071T1/sl unknown
- 2000-11-09 PT PT00977095T patent/PT1228071E/pt unknown
- 2000-11-09 ES ES10176390T patent/ES2381174T3/es not_active Expired - Lifetime
- 2000-11-09 PT PT10176420T patent/PT2263669E/pt unknown
- 2000-11-09 HK HK03100819.6A patent/HK1049158A1/zh unknown
- 2000-11-09 AT AT10176420T patent/ATE544452T1/de active
- 2000-11-09 WO PCT/US2000/030770 patent/WO2001034606A1/en not_active Ceased
- 2000-11-09 EP EP06009632A patent/EP1698334B1/en not_active Expired - Lifetime
-
2002
- 2002-05-08 NO NO20022223A patent/NO323633B1/no not_active IP Right Cessation
- 2002-05-10 FI FI20020892A patent/FI119931B/fi not_active IP Right Cessation
-
2005
- 2005-07-07 AU AU2005202964A patent/AU2005202964B2/en not_active Ceased
-
2007
- 2007-03-21 NO NO20071490A patent/NO336210B1/no not_active IP Right Cessation
- 2007-04-05 CY CY20071100487T patent/CY1107610T1/el unknown
-
2012
- 2012-04-26 CY CY20121100399T patent/CY1112707T1/el unknown
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