FI119931B - Farmaseuttisesti aktiivisia isoindolini-johdannaisia - Google Patents

Info

Publication number

FI119931B

FI119931B FI20020892A FI20020892A FI119931B FI 119931 B FI119931 B FI 119931B FI 20020892 A FI20020892 A FI 20020892A FI 20020892 A FI20020892 A FI 20020892A FI 119931 B FI119931 B FI 119931B

Authority

FI

Finland

Prior art keywords

methoxyphenyl

ethoxy

dioxoisoindolin

dione

methylsulfonyl

Prior art date

1999-11-12

Links

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• Global Dossier
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• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 8
• 150000003839 salts Chemical class 0.000 claims abstract description 6
• -1 3-ethoxy-4-methoxyphenyl Chemical group 0.000 claims description 176
• 239000000203 mixture Substances 0.000 claims description 139
• 150000001875 compounds Chemical class 0.000 claims description 79
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 54
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 44
• 206010028980 Neoplasm Diseases 0.000 claims description 42
• 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 39
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 39
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 21
• 230000033115 angiogenesis Effects 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 19
• 238000004519 manufacturing process Methods 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• 201000011510 cancer Diseases 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 10
• 208000030507 AIDS Diseases 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 206010003246 arthritis Diseases 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 230000004054 inflammatory process Effects 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 7
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 239000002775 capsule Substances 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 5
• 150000003857 carboxamides Chemical class 0.000 claims description 5
• 239000002552 dosage form Substances 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 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 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• LLYCQFTTYQQHMI-GOSISDBHSA-N (3r)-3-[4-[(2-chloroacetyl)amino]-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(=O)CCl)C=CC=C3C2)=O)=C1 LLYCQFTTYQQHMI-GOSISDBHSA-N 0.000 claims description 3
• 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 3
• 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 3
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000001118 alkylidene group Chemical group 0.000 claims description 3
• 210000001185 bone marrow Anatomy 0.000 claims description 3
• 208000024908 graft versus host disease Diseases 0.000 claims description 3
• 201000010536 head and neck cancer Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 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 3
• 201000011682 nervous system cancer Diseases 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• 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 2
• RJNHBBSGPDOAND-UHFFFAOYSA-N 2-(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)C(C)N(C)C)C=CC=C3C2=O)=O)=C1 RJNHBBSGPDOAND-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• HGWJEAFEEZXCPG-UHFFFAOYSA-N 2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-oxobutyl]-4-(1h-pyrrol-2-yl)isoindole-1,3-dione Chemical compound COC1=CC=C(C(CC(C)=O)N2C(C3=C(C=4NC=CC=4)C=CC=C3C2=O)=O)C=C1OC1CCCC1 HGWJEAFEEZXCPG-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• AUYSFUSWFJUKMJ-HXUWFJFHSA-N C(C)OC=1C=C(C=CC=1OC)[C@@H](CC(C)=O)N1C(C2=CC=CC(=C2C1=O)C=1NC=CC=1)=O Chemical compound C(C)OC=1C=C(C=CC=1OC)[C@@H](CC(C)=O)N1C(C2=CC=CC(=C2C1=O)C=1NC=CC=1)=O AUYSFUSWFJUKMJ-HXUWFJFHSA-N 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• PAOZAMACNXMCIB-UHFFFAOYSA-N N-[2-[1-(3,4-dimethoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CS(C)(=O)=O)N1C(=O)C2=C(NC(=O)C3CC3)C=CC=C2C1=O PAOZAMACNXMCIB-UHFFFAOYSA-N 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 229940102223 injectable solution Drugs 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 208000032612 Glial tumor Diseases 0.000 claims 4
• 206010018338 Glioma Diseases 0.000 claims 4
• 206010003571 Astrocytoma Diseases 0.000 claims 2
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
• 206010005003 Bladder cancer Diseases 0.000 claims 2
• 206010006187 Breast cancer Diseases 0.000 claims 2
• 208000026310 Breast neoplasm Diseases 0.000 claims 2
• 206010009944 Colon cancer Diseases 0.000 claims 2
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
• 206010033128 Ovarian cancer Diseases 0.000 claims 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
• 102000035195 Peptidases Human genes 0.000 claims 2
• 108091005804 Peptidases Proteins 0.000 claims 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
• 206010060862 Prostate cancer Diseases 0.000 claims 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
• 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
• 208000032383 Soft tissue cancer Diseases 0.000 claims 2
• 206010042971 T-cell lymphoma Diseases 0.000 claims 2
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
• 201000009036 biliary tract cancer Diseases 0.000 claims 2
• 208000020790 biliary tract neoplasm Diseases 0.000 claims 2
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
• 208000029742 colonic neoplasm Diseases 0.000 claims 2
• 230000008034 disappearance Effects 0.000 claims 2
• 208000005017 glioblastoma Diseases 0.000 claims 2
• 210000005229 liver cell Anatomy 0.000 claims 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
• 239000011159 matrix material Substances 0.000 claims 2
• 239000002184 metal Substances 0.000 claims 2
• 201000000050 myeloid neoplasm Diseases 0.000 claims 2
• 230000002071 myeloproliferative effect Effects 0.000 claims 2
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
• 201000002528 pancreatic cancer Diseases 0.000 claims 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
• 235000019833 protease Nutrition 0.000 claims 2
• 208000015347 renal cell adenocarcinoma Diseases 0.000 claims 2
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims 2
• 210000002700 urine Anatomy 0.000 claims 2
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• IOIBFPBEUNZCMX-PVQCJRHBSA-N 4-amino-2-[(1r)-1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(C)O)N2C(C3=C(N)C=CC=C3C2=O)=O)=C1 IOIBFPBEUNZCMX-PVQCJRHBSA-N 0.000 claims 1
• HEWRXBRDIAUSKW-MRXNPFEDSA-N 4-amino-2-[(1r)-1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]isoindole-1,3-dione Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CC(C)=O)N2C(C3=C(N)C=CC=C3C2=O)=O)=C1 HEWRXBRDIAUSKW-MRXNPFEDSA-N 0.000 claims 1
• 208000003950 B-cell lymphoma Diseases 0.000 claims 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
• 206010027406 Mesothelioma Diseases 0.000 claims 1
• AUJIEZAMWPGPDR-UHFFFAOYSA-N N-(1,3-dioxoisoindol-2-yl)-N-methylsulfonylmethanesulfonamide Chemical compound CS(=O)(=O)N(S(=O)(=O)C)N1C(C2=CC=CC=C2C1=O)=O AUJIEZAMWPGPDR-UHFFFAOYSA-N 0.000 claims 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
• 230000003115 biocidal effect Effects 0.000 claims 1
• 125000004663 dialkyl amino group Chemical group 0.000 claims 1
• 201000005202 lung cancer Diseases 0.000 claims 1
• 208000020816 lung neoplasm Diseases 0.000 claims 1
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