CZ20032041A3 - Isoindolimidové deriváty - Google Patents

Info

Publication number

CZ20032041A3

CZ20032041A3 CZ20032041A CZ20032041A CZ20032041A3 CZ 20032041 A3 CZ20032041 A3 CZ 20032041A3 CZ 20032041 A CZ20032041 A CZ 20032041A CZ 20032041 A CZ20032041 A CZ 20032041A CZ 20032041 A3 CZ20032041 A3 CZ 20032041A3

Authority

CZ

Czechia

Prior art keywords

alkyl

dioxo

piperidyl

methyl

dioxopiperidin

Prior art date

2000-12-27

Links

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• -1 Isoindole imide Chemical class 0.000 title claims description 236
• 150000001875 compounds Chemical class 0.000 claims abstract description 327
• 241000124008 Mammalia Species 0.000 claims abstract description 69
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 46
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 23
• 238000004519 manufacturing process Methods 0.000 claims abstract description 22
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 11
• 208000019622 heart disease Diseases 0.000 claims abstract description 8
• 239000000203 mixture Substances 0.000 claims description 276
• 125000003118 aryl group Chemical group 0.000 claims description 149
• 125000001072 heteroaryl group Chemical group 0.000 claims description 116
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 114
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 104
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 98
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 97
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 84
• 238000000034 method Methods 0.000 claims description 76
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 25
• 201000011510 cancer Diseases 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 210000001519 tissue Anatomy 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 150000001721 carbon Chemical group 0.000 claims description 14
• 210000004369 blood Anatomy 0.000 claims description 13
• 239000008280 blood Substances 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 210000004962 mammalian cell Anatomy 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 12
• 238000012360 testing method Methods 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 230000001684 chronic effect Effects 0.000 claims description 10
• 230000006378 damage Effects 0.000 claims description 10
• 230000006433 tumor necrosis factor production Effects 0.000 claims description 10
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 7
• 201000008482 osteoarthritis Diseases 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 208000027418 Wounds and injury Diseases 0.000 claims description 6
• GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims description 6
• 210000004185 liver Anatomy 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 210000000664 rectum Anatomy 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• SVSMQAPPCVNXQW-UHFFFAOYSA-N 2-chloro-n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]acetamide Chemical compound O=C1C=2C(NC(=O)CCl)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O SVSMQAPPCVNXQW-UHFFFAOYSA-N 0.000 claims description 5
• 208000034578 Multiple myelomas Diseases 0.000 claims description 5
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 5
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 5
• 210000000988 bone and bone Anatomy 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
• 210000001072 colon Anatomy 0.000 claims description 5
• 210000003128 head Anatomy 0.000 claims description 5
• 208000014674 injury Diseases 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
• 210000000867 larynx Anatomy 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 210000000214 mouth Anatomy 0.000 claims description 5
• 210000003739 neck Anatomy 0.000 claims description 5
• 210000001672 ovary Anatomy 0.000 claims description 5
• 210000003800 pharynx Anatomy 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 5
• 210000000952 spleen Anatomy 0.000 claims description 5
• 210000001550 testis Anatomy 0.000 claims description 5
• 210000004291 uterus Anatomy 0.000 claims description 5
• KIYGXFJOOIEPNO-UHFFFAOYSA-N 1-cyclopentyl-3-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]urea Chemical compound C1CCCC1NC(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O KIYGXFJOOIEPNO-UHFFFAOYSA-N 0.000 claims description 4
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
• 239000002246 antineoplastic agent Substances 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
• 239000007943 implant Substances 0.000 claims description 4
• 230000031261 interleukin-10 production Effects 0.000 claims description 4
• 210000001165 lymph node Anatomy 0.000 claims description 4
• UWNBNIUPNHDFRA-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=CC2=C1C(=O)N(C1C(NC(=O)CC1)=O)C2=O UWNBNIUPNHDFRA-UHFFFAOYSA-N 0.000 claims description 4
• HWKZFWLDUJZNLU-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)N(C1C(NC(=O)CC1)=O)C2=O HWKZFWLDUJZNLU-UHFFFAOYSA-N 0.000 claims description 4
• GNQIBHPPXHWHFQ-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=CC=CC2=C1C(=O)N(C1C(NC(=O)CC1)=O)C2=O GNQIBHPPXHWHFQ-UHFFFAOYSA-N 0.000 claims description 4
• 210000000496 pancreas Anatomy 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 210000003932 urinary bladder Anatomy 0.000 claims description 4
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
• CLGYDNGWRRGLFE-UHFFFAOYSA-N 1-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]-3-octylurea Chemical compound O=C1C=2C(CNC(=O)NCCCCCCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O CLGYDNGWRRGLFE-UHFFFAOYSA-N 0.000 claims description 3
• FKOFRYWZKLLJHJ-UHFFFAOYSA-N 1-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O FKOFRYWZKLLJHJ-UHFFFAOYSA-N 0.000 claims description 3
• HNPGYBNMOZYMJO-UHFFFAOYSA-N 1-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]-3-propylurea Chemical compound O=C1C=2C(CNC(=O)NCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O HNPGYBNMOZYMJO-UHFFFAOYSA-N 0.000 claims description 3
• OWJDKMFZNZKFEZ-UHFFFAOYSA-N 1-butyl-3-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]urea Chemical compound O=C1C=2C(CNC(=O)NCCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O OWJDKMFZNZKFEZ-UHFFFAOYSA-N 0.000 claims description 3
• GYBAWNXMPZVXFQ-UHFFFAOYSA-N 1-cyclohexyl-3-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]urea Chemical compound C1CCCCC1NC(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O GYBAWNXMPZVXFQ-UHFFFAOYSA-N 0.000 claims description 3
• GPEDWDVUPFIAIV-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-4-(2-phenylmethoxyethylamino)isoindole-1,3-dione Chemical compound O=C1C(C(=CC=C2)NCCOCC=3C=CC=CC=3)=C2C(=O)N1C1CCC(=O)NC1=O GPEDWDVUPFIAIV-UHFFFAOYSA-N 0.000 claims description 3
• FTZARLOKGLDDOC-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-4-(heptylamino)isoindole-1,3-dione Chemical compound O=C1C=2C(NCCCCCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O FTZARLOKGLDDOC-UHFFFAOYSA-N 0.000 claims description 3
• VUFGKXWZCASHSG-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-4-(pentylamino)isoindole-1,3-dione Chemical compound O=C1C=2C(NCCCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O VUFGKXWZCASHSG-UHFFFAOYSA-N 0.000 claims description 3
• IQACOJIVZRDPIM-UHFFFAOYSA-N 2-azido-n-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindol-4-yl]acetamide Chemical compound C1C=2C(NC(=O)CN=[N+]=[N-])=CC=CC=2C(=O)N1C1CCC(=O)NC1=O IQACOJIVZRDPIM-UHFFFAOYSA-N 0.000 claims description 3
• RAECDRLOAIXBNG-UHFFFAOYSA-N 2-chloro-n-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindol-4-yl]acetamide Chemical compound C1C=2C(NC(=O)CCl)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O RAECDRLOAIXBNG-UHFFFAOYSA-N 0.000 claims description 3
• XRAYWKDMFVKUTJ-UHFFFAOYSA-N 2-chloro-n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]acetamide Chemical compound O=C1C=2C(CNC(=O)CCl)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O XRAYWKDMFVKUTJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• VWZVRHSJOPXCKC-UHFFFAOYSA-N 3-[7-(benzylamino)-3-oxo-1h-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(C2C(NC(=O)CC2)=O)CC2=C1C=CC=C2NCC1=CC=CC=C1 VWZVRHSJOPXCKC-UHFFFAOYSA-N 0.000 claims description 3
• CTBWWPIIRKWDDL-UHFFFAOYSA-N 3-amino-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(N)=C1 CTBWWPIIRKWDDL-UHFFFAOYSA-N 0.000 claims description 3
• TUMJPYMYNBEMDD-UHFFFAOYSA-N 4-(aminomethyl)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C=2C(CN)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O TUMJPYMYNBEMDD-UHFFFAOYSA-N 0.000 claims description 3
• WUTOYMPPCGEPEL-UHFFFAOYSA-N 4-[(3-chlorophenyl)methylamino]-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound ClC1=CC=CC(CNC=2C=3C(=O)N(C4C(NC(=O)CC4)=O)C(=O)C=3C=CC=2)=C1 WUTOYMPPCGEPEL-UHFFFAOYSA-N 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• 208000019693 Lung disease Diseases 0.000 claims description 3
• OBBCQKHWPYKEMI-UHFFFAOYSA-N [2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methylamino]-2-oxoethyl] acetate Chemical compound O=C1C=2C(CNC(=O)COC(=O)C)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O OBBCQKHWPYKEMI-UHFFFAOYSA-N 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• HADVZQNRDFIJQJ-UHFFFAOYSA-N benzyl n-[6-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]-6-oxohexyl]carbamate Chemical compound C=1C=CC=2C(=O)N(C3C(NC(=O)CC3)=O)C(=O)C=2C=1NC(=O)CCCCCNC(=O)OCC1=CC=CC=C1 HADVZQNRDFIJQJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• 229960004768 irinotecan Drugs 0.000 claims description 3
• KKTLQRZWRNYBRJ-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-2-phenylacetamide Chemical compound C=1C=CC=2C(=O)N(C3C(NC(=O)CC3)=O)C(=O)C=2C=1NC(=O)CC1=CC=CC=C1 KKTLQRZWRNYBRJ-UHFFFAOYSA-N 0.000 claims description 3
• DBFWANUUPKGPFE-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=3C(=O)N(C4C(NC(=O)CC4)=O)C(=O)C=3C=CC=2)=C1 DBFWANUUPKGPFE-UHFFFAOYSA-N 0.000 claims description 3
• DHXDQHFQUPSHMN-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=3C(=O)N(C4C(NC(=O)CC4)=O)C(=O)C=3C=CC=2)=C1 DHXDQHFQUPSHMN-UHFFFAOYSA-N 0.000 claims description 3
• KQFNDICMWIUZEQ-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=3C(=O)N(C4C(NC(=O)CC4)=O)C(=O)C=3C=CC=2)=C1 KQFNDICMWIUZEQ-UHFFFAOYSA-N 0.000 claims description 3
• RVFKAPPWQGGDFX-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)N(C1C(NC(=O)CC1)=O)C2=O RVFKAPPWQGGDFX-UHFFFAOYSA-N 0.000 claims description 3
• GCYCCBRTJYRRNK-UHFFFAOYSA-N n-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O GCYCCBRTJYRRNK-UHFFFAOYSA-N 0.000 claims description 3
• UJZAGPRTRGMLOF-UHFFFAOYSA-N n-[2-(3-methyl-2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]heptanamide Chemical compound O=C1C=2C(NC(=O)CCCCCC)=CC=CC=2C(=O)N1C1(C)CCC(=O)NC1=O UJZAGPRTRGMLOF-UHFFFAOYSA-N 0.000 claims description 3
• JRKZXUJIOPCGGI-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]-2-methoxyacetamide Chemical compound O=C1C=2C(CNC(=O)COC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O JRKZXUJIOPCGGI-UHFFFAOYSA-N 0.000 claims description 3
• XKFHXTMSMUHONX-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O XKFHXTMSMUHONX-UHFFFAOYSA-N 0.000 claims description 3
• RJIQBXMVWAVGFJ-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]cyclopentanecarboxamide Chemical compound C1CCCC1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O RJIQBXMVWAVGFJ-UHFFFAOYSA-N 0.000 claims description 3
• TVOVTRQGKCWEAG-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O TVOVTRQGKCWEAG-UHFFFAOYSA-N 0.000 claims description 3
• UDODWYJNTGKWBS-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]heptanamide Chemical compound O=C1C=2C(CNC(=O)CCCCCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UDODWYJNTGKWBS-UHFFFAOYSA-N 0.000 claims description 3
• FWELFDXVJGXJIY-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]propanamide Chemical compound O=C1C=2C(CNC(=O)CC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O FWELFDXVJGXJIY-UHFFFAOYSA-N 0.000 claims description 3
• BIUYITAPSPGGPW-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O BIUYITAPSPGGPW-UHFFFAOYSA-N 0.000 claims description 3
• MCZGCFYKEVRECX-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O MCZGCFYKEVRECX-UHFFFAOYSA-N 0.000 claims description 3
• IGUDNJLDVFQEGM-UHFFFAOYSA-N n-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCC(C=1C2=O)=CC=CC=1C(=O)N2C1CCC(=O)NC1=O IGUDNJLDVFQEGM-UHFFFAOYSA-N 0.000 claims description 3
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 2
• RBOPGPIIBBSRQO-UHFFFAOYSA-N 1-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]methyl]-3-ethylthiourea Chemical compound O=C1C=2C(CNC(=S)NCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O RBOPGPIIBBSRQO-UHFFFAOYSA-N 0.000 claims description 2
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• IYSIDZMLLKLYIO-UHFFFAOYSA-N 1-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3h-isoindol-4-yl]methyl]-3-ethylurea Chemical compound C1C=2C(CNC(=O)NCC)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O IYSIDZMLLKLYIO-UHFFFAOYSA-N 0.000 claims description 2
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