KR20070057969A - 화학적 화합물 - Google Patents

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Publication number

KR20070057969A

KR20070057969A KR1020077009055A KR20077009055A KR20070057969A KR 20070057969 A KR20070057969 A KR 20070057969A KR 1020077009055 A KR1020077009055 A KR 1020077009055A KR 20077009055 A KR20077009055 A KR 20077009055A KR 20070057969 A KR20070057969 A KR 20070057969A

Authority

KR

South Korea

Prior art keywords

phenyl

piperidinyl

indole

sulfonyl

carboxamide

Prior art date

2004-09-21

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.)

Withdrawn

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 251
• 238000000034 method Methods 0.000 claims abstract description 137
• 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 claims abstract description 53
• 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 claims abstract description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 208000035475 disorder Diseases 0.000 claims abstract description 48
• 230000000694 effects Effects 0.000 claims abstract description 43
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 230000001404 mediated effect Effects 0.000 claims abstract description 19
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 17
• 208000006673 asthma Diseases 0.000 claims abstract description 12
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 12
• -1 -ORc Chemical group 0.000 claims description 277
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 233
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 219
• 125000001424 substituent group Chemical group 0.000 claims description 193
• 125000001072 heteroaryl group Chemical group 0.000 claims description 177
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 143
• 125000005843 halogen group Chemical group 0.000 claims description 104
• 229910003827 NRaRb Inorganic materials 0.000 claims description 99
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 74
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 67
• 229910052799 carbon Inorganic materials 0.000 claims description 63
• 125000004043 oxo group Chemical group O=* 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 125000004429 atom Chemical group 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 32
• 239000000470 constituent Substances 0.000 claims description 30
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 29
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 27
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
• 239000012453 solvate Substances 0.000 claims description 25
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• AWEOCCDQVPBWPZ-UHFFFAOYSA-N 3-[1-(2-aminoethylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 AWEOCCDQVPBWPZ-UHFFFAOYSA-N 0.000 claims description 8
• OWWCZWSAXMTESV-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 OWWCZWSAXMTESV-UHFFFAOYSA-N 0.000 claims description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
• 230000002757 inflammatory effect Effects 0.000 claims description 8
• GMIQJWKIKIPZJZ-UHFFFAOYSA-N 3-[1-(3-morpholin-4-ylpropylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCOCC1 GMIQJWKIKIPZJZ-UHFFFAOYSA-N 0.000 claims description 7
• MJWPHYZQZROWPH-UHFFFAOYSA-N 3-[1-[2-(dimethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 MJWPHYZQZROWPH-UHFFFAOYSA-N 0.000 claims description 7
• ONGHZGNQHUWTAY-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C3=CSC=C3)C=C12 ONGHZGNQHUWTAY-UHFFFAOYSA-N 0.000 claims description 7
• ROHVMXPLAXOWHS-UHFFFAOYSA-N 5-phenyl-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 ROHVMXPLAXOWHS-UHFFFAOYSA-N 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 210000000056 organ Anatomy 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• CAVRRSRWRKKJPD-UHFFFAOYSA-N 3-[1-(2-methoxyethylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 CAVRRSRWRKKJPD-UHFFFAOYSA-N 0.000 claims description 6
• PQPZVWJPKZMXJV-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 PQPZVWJPKZMXJV-UHFFFAOYSA-N 0.000 claims description 6
• KBLLMOCRHWALMG-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C3=CSC=C3)C=C12 KBLLMOCRHWALMG-UHFFFAOYSA-N 0.000 claims description 6
• JXUXTVXXOBFIHD-UHFFFAOYSA-N 3-[1-(3-morpholin-4-ylpropylsulfonyl)piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3SC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCOCC1 JXUXTVXXOBFIHD-UHFFFAOYSA-N 0.000 claims description 6
• FPQWIPSAJFRIKL-UHFFFAOYSA-N 3-[1-(3-morpholin-4-ylpropylsulfonyl)piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C3=CSC=C3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCOCC1 FPQWIPSAJFRIKL-UHFFFAOYSA-N 0.000 claims description 6
• VQIIDCSRXUTGCN-UHFFFAOYSA-N 3-[1-[3-(diethylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(CC)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 VQIIDCSRXUTGCN-UHFFFAOYSA-N 0.000 claims description 6
• GEFQTJSOUFTLDH-SFTDATJTSA-N 3-[1-[3-[(2s,5s)-2,5-dimethylpyrrolidin-1-yl]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C[C@H]1CC[C@H](C)N1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 GEFQTJSOUFTLDH-SFTDATJTSA-N 0.000 claims description 6
• YEQAPFBDOIVVRV-UHFFFAOYSA-N 5-phenyl-3-[1-(2-pyrrolidin-1-ylethylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCN1CCCC1 YEQAPFBDOIVVRV-UHFFFAOYSA-N 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• SVARYXPHSVFBCG-UHFFFAOYSA-N 3-[1-(2-ethoxyethylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 SVARYXPHSVFBCG-UHFFFAOYSA-N 0.000 claims description 5
• ORIMLZAWSAVTJO-UHFFFAOYSA-N 3-[1-(2-hydroxyethylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C1CCN(S(=O)(=O)CCO)CC1 ORIMLZAWSAVTJO-UHFFFAOYSA-N 0.000 claims description 5
• ZCCSQGLWKJAFEJ-UHFFFAOYSA-N 3-[1-(2-pyrrolidin-1-ylethylsulfonyl)piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C3=CSC=C3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCN1CCCC1 ZCCSQGLWKJAFEJ-UHFFFAOYSA-N 0.000 claims description 5
• RHWUMIFHSYILHS-UHFFFAOYSA-N 3-[1-(3-hydroxypropylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C1CCN(S(=O)(=O)CCCO)CC1 RHWUMIFHSYILHS-UHFFFAOYSA-N 0.000 claims description 5
• RNEKLUJSMBDEAU-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-(methylaminomethyl)phenyl]-1h-indole-7-carboxamide Chemical compound CNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 RNEKLUJSMBDEAU-UHFFFAOYSA-N 0.000 claims description 5
• VDLFSWCPNGKSPJ-UHFFFAOYSA-N 3-[1-[2-(cyclopentylamino)ethylsulfonyl]piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3SC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCNC1CCCC1 VDLFSWCPNGKSPJ-UHFFFAOYSA-N 0.000 claims description 5
• LVAVWTZPZUZICV-UHFFFAOYSA-N 3-[1-[2-(dimethylamino)ethylsulfonyl]piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C3=CSC=C3)C=C12 LVAVWTZPZUZICV-UHFFFAOYSA-N 0.000 claims description 5
• URKWDRCDAOQQEN-UHFFFAOYSA-N 3-[1-[3-[di(propan-2-yl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C(C)C)C(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 URKWDRCDAOQQEN-UHFFFAOYSA-N 0.000 claims description 5
• WWFOHLGOAODWDE-UHFFFAOYSA-N 5-[3-[(2,2-dimethylpropylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC(C)(C)C)C=CC=3)C=C12 WWFOHLGOAODWDE-UHFFFAOYSA-N 0.000 claims description 5
• LGBXMJWMQPZHHY-UHFFFAOYSA-N 5-[5-(pyrrolidin-1-ylmethyl)thiophen-2-yl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3SC(CN4CCCC4)=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 LGBXMJWMQPZHHY-UHFFFAOYSA-N 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 206010006895 Cachexia Diseases 0.000 claims description 5
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 150000007942 carboxylates Chemical class 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 230000005855 radiation Effects 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
• 230000017423 tissue regeneration Effects 0.000 claims description 5
• IBHBSLBQSHEYEW-UHFFFAOYSA-N 3-[1-(2-morpholin-4-ylethylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCN1CCOCC1 IBHBSLBQSHEYEW-UHFFFAOYSA-N 0.000 claims description 4
• NHQWNHXUANHIBQ-UHFFFAOYSA-N 3-[1-(3-ethoxypropylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 NHQWNHXUANHIBQ-UHFFFAOYSA-N 0.000 claims description 4
• LMUDDZVWGKMCSO-UHFFFAOYSA-N 3-[1-(3-ethoxypropylsulfonyl)piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3SC=CC=3)C=C12 LMUDDZVWGKMCSO-UHFFFAOYSA-N 0.000 claims description 4
• QWRVROMFVKSABE-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-(propylaminomethyl)phenyl]-1h-indole-7-carboxamide Chemical compound CCCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 QWRVROMFVKSABE-UHFFFAOYSA-N 0.000 claims description 4
• SFIFIOSFVGXFDX-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[(oxolan-2-ylmethylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC4OCCC4)C=CC=3)C=C12 SFIFIOSFVGXFDX-UHFFFAOYSA-N 0.000 claims description 4
• PGHGCVREEDYORO-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[(propan-2-ylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC(C)C)C=CC=3)C=C12 PGHGCVREEDYORO-UHFFFAOYSA-N 0.000 claims description 4
• TYCAVTKSGIQXCY-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[(pyridin-2-ylmethylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC=4N=CC=CC=4)C=CC=3)C=C12 TYCAVTKSGIQXCY-UHFFFAOYSA-N 0.000 claims description 4
• ZZVICLRBPQIWFL-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[(pyridin-4-ylmethylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC=4C=CN=CC=4)C=CC=3)C=C12 ZZVICLRBPQIWFL-UHFFFAOYSA-N 0.000 claims description 4
• SFIFIOSFVGXFDX-RUZDIDTESA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[[[(2r)-oxolan-2-yl]methylamino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC[C@@H]4OCCC4)C=CC=3)C=C12 SFIFIOSFVGXFDX-RUZDIDTESA-N 0.000 claims description 4
• RSGCNFUIAYSKBK-NRFANRHFSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[[[(2s)-3-methylbutan-2-yl]amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN[C@@H](C)C(C)C)C=CC=3)C=C12 RSGCNFUIAYSKBK-NRFANRHFSA-N 0.000 claims description 4
• CMRSANBYQLHZIF-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[[methyl(prop-2-enyl)amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN(C)CC=C)C=CC=3)C=C12 CMRSANBYQLHZIF-UHFFFAOYSA-N 0.000 claims description 4
• JUWVRJPAUHWQSQ-UHFFFAOYSA-N 3-[1-[2-(2-hydroxyethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C1CCN(S(=O)(=O)CCNCCO)CC1 JUWVRJPAUHWQSQ-UHFFFAOYSA-N 0.000 claims description 4
• VYTJESRILHKPAP-UHFFFAOYSA-N 3-[1-[2-(4-acetylpiperazin-1-yl)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(C(=O)C)CCN1CCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 VYTJESRILHKPAP-UHFFFAOYSA-N 0.000 claims description 4
• RIDOVDOUSMRZLW-UHFFFAOYSA-N 3-[1-[2-(4-hydroxybutoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C1CCN(S(=O)(=O)CCOCCCCO)CC1 RIDOVDOUSMRZLW-UHFFFAOYSA-N 0.000 claims description 4
• KEAKQBUGPVKASK-UHFFFAOYSA-N 3-[1-[2-(4-hydroxypiperidin-1-yl)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCN1CCC(O)CC1 KEAKQBUGPVKASK-UHFFFAOYSA-N 0.000 claims description 4
• PRVFBTAIXBATKR-UHFFFAOYSA-N 3-[1-[2-(4-methylpiperazin-1-yl)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(C)CCN1CCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 PRVFBTAIXBATKR-UHFFFAOYSA-N 0.000 claims description 4
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• VTNLMEAPLQOPRY-UHFFFAOYSA-N 3-[1-[2-(diethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(CC)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 VTNLMEAPLQOPRY-UHFFFAOYSA-N 0.000 claims description 4
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• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
• KGWUANRYORTIJK-UHFFFAOYSA-N tert-butyl 4-[3-[4-(7-carbamoyl-5-phenyl-1h-indol-3-yl)piperidin-1-yl]sulfonylpropylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 KGWUANRYORTIJK-UHFFFAOYSA-N 0.000 claims description 3
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• DOOXUTXOZKBSMH-UHFFFAOYSA-N 3-[1-(3-ethoxypropylsulfonyl)piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C3=CSC=C3)C=C12 DOOXUTXOZKBSMH-UHFFFAOYSA-N 0.000 claims description 2
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• FOKZKYYHWAJLTC-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[5-(pyrrolidin-1-ylmethyl)thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCCC4)SC=3)C=C12 FOKZKYYHWAJLTC-UHFFFAOYSA-N 0.000 claims description 2
• CRUCXCUTHWQFEG-UHFFFAOYSA-N 3-[1-(3-phenoxypropylsulfonyl)piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOC1=CC=CC=C1 CRUCXCUTHWQFEG-UHFFFAOYSA-N 0.000 claims description 2
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• CXFXPOVIKRNHOK-UHFFFAOYSA-N 3-[1-(4-methylthiophen-2-yl)sulfonylpiperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC1=CSC(S(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)=C1 CXFXPOVIKRNHOK-UHFFFAOYSA-N 0.000 claims description 2
• HSGAXICRNXDFNV-UHFFFAOYSA-N 3-[1-(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylpiperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 HSGAXICRNXDFNV-UHFFFAOYSA-N 0.000 claims description 2
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• SYELJGQBJCZHGG-UHFFFAOYSA-N 3-[1-[(4-chloro-2,1,3-benzoxadiazol-5-yl)sulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1C=2C(C3CCN(CC3)S(=O)(=O)C3=C(C4=NON=C4C=C3)Cl)=CNC=2C(C(=O)N)=CC=1C1=CC=CC=C1 SYELJGQBJCZHGG-UHFFFAOYSA-N 0.000 claims description 2
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• YEHBHLFUJZENIU-UHFFFAOYSA-N 3-[1-[2-(2-acetamidoethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCNC(=O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 YEHBHLFUJZENIU-UHFFFAOYSA-N 0.000 claims description 2
• JLQVLRKOPPQCNJ-UHFFFAOYSA-N 3-[1-[2-(2-ethoxyethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 JLQVLRKOPPQCNJ-UHFFFAOYSA-N 0.000 claims description 2
• MFFZXLIWCSAOPC-UHFFFAOYSA-N 3-[1-[2-(2-methoxyethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCNCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 MFFZXLIWCSAOPC-UHFFFAOYSA-N 0.000 claims description 2
• KTHCTUGJVOOAQF-UHFFFAOYSA-N 3-[1-[2-(2-methylpropoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCC(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 KTHCTUGJVOOAQF-UHFFFAOYSA-N 0.000 claims description 2
• MVQPSNLDWGXDSF-UHFFFAOYSA-N 3-[1-[2-(2-methylsulfanylethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCSC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 MVQPSNLDWGXDSF-UHFFFAOYSA-N 0.000 claims description 2
• HUQMCNWYQBONOV-UHFFFAOYSA-N 3-[1-[2-(2-methylsulfonylethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCS(=O)(=O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 HUQMCNWYQBONOV-UHFFFAOYSA-N 0.000 claims description 2
• NJNRARLCEASHJH-UHFFFAOYSA-N 3-[1-[2-(2-morpholin-4-ylethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCCN1CCOCC1 NJNRARLCEASHJH-UHFFFAOYSA-N 0.000 claims description 2
• BPWFGSGGUJGSMO-UHFFFAOYSA-N 3-[1-[2-(2-morpholin-4-ylethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCNCCN1CCOCC1 BPWFGSGGUJGSMO-UHFFFAOYSA-N 0.000 claims description 2
• WYWPRQSZLNLMLE-UHFFFAOYSA-N 3-[1-[2-(3-hydroxybutan-2-yloxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOC(C)C(O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 WYWPRQSZLNLMLE-UHFFFAOYSA-N 0.000 claims description 2
• VOAFXUITBDLQKD-UHFFFAOYSA-N 3-[1-[2-(3-morpholin-4-ylpropylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCNCCCN1CCOCC1 VOAFXUITBDLQKD-UHFFFAOYSA-N 0.000 claims description 2
• XXWXSMLBUGHBDJ-UHFFFAOYSA-N 3-[1-[2-(4-carbamoylpiperidin-1-yl)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CC(C(=O)N)CCN1CCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 XXWXSMLBUGHBDJ-UHFFFAOYSA-N 0.000 claims description 2
• VOUVGKGISWAWRV-UHFFFAOYSA-N 3-[1-[2-(benzylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCNCC1=CC=CC=C1 VOUVGKGISWAWRV-UHFFFAOYSA-N 0.000 claims description 2
• QAGKYKLBVUWINY-UHFFFAOYSA-N 3-[1-[2-(cyclobutylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCNC1CCC1 QAGKYKLBVUWINY-UHFFFAOYSA-N 0.000 claims description 2
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• RFMSIPBWNDJQDZ-UHFFFAOYSA-N 3-[1-[2-(furan-2-ylmethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCC1=CC=CO1 RFMSIPBWNDJQDZ-UHFFFAOYSA-N 0.000 claims description 2
• UNGFRUAAHBLSPT-UHFFFAOYSA-N 3-[1-[2-(furan-3-ylmethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCC=1C=COC=1 UNGFRUAAHBLSPT-UHFFFAOYSA-N 0.000 claims description 2
• CMEULOVXFZPQHR-UHFFFAOYSA-N 3-[1-[2-(oxolan-3-ylmethoxy)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCC1CCOC1 CMEULOVXFZPQHR-UHFFFAOYSA-N 0.000 claims description 2
• AKZJCIYWBDJQMB-UHFFFAOYSA-N 3-[1-[2-[(2-methylcyclopropyl)methoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC1CC1COCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 AKZJCIYWBDJQMB-UHFFFAOYSA-N 0.000 claims description 2
• CYOJZOFIFPRBQU-RTBURBONSA-N 3-[1-[2-[(2r,4r)-4-hydroxypentan-2-yl]oxyethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCO[C@H](C)C[C@H](O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 CYOJZOFIFPRBQU-RTBURBONSA-N 0.000 claims description 2
• CYOJZOFIFPRBQU-OALUTQOASA-N 3-[1-[2-[(2s,4s)-4-hydroxypentan-2-yl]oxyethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCO[C@@H](C)C[C@@H](O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 CYOJZOFIFPRBQU-OALUTQOASA-N 0.000 claims description 2
• UBJLEFHNMZOOSU-UHFFFAOYSA-N 3-[1-[2-[2-(2-oxopyrrolidin-1-yl)ethoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCCN1CCCC1=O UBJLEFHNMZOOSU-UHFFFAOYSA-N 0.000 claims description 2
• OKYSJJJXPHBLST-UHFFFAOYSA-N 3-[1-[2-[2-(diethylamino)ethoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCN(CC)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 OKYSJJJXPHBLST-UHFFFAOYSA-N 0.000 claims description 2
• DUCOMDJESHGWMH-UHFFFAOYSA-N 3-[1-[2-[2-(dimethylamino)ethyl-methylamino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)CCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 DUCOMDJESHGWMH-UHFFFAOYSA-N 0.000 claims description 2
• ZQMUCAVEBSMITE-UHFFFAOYSA-N 3-[1-[2-[2-(dimethylamino)ethylamino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCNCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 ZQMUCAVEBSMITE-UHFFFAOYSA-N 0.000 claims description 2
• UCQKKPCHTVGHGN-UHFFFAOYSA-N 3-[1-[2-[2-[(4-methylphenyl)sulfonylamino]ethylamino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCNCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 UCQKKPCHTVGHGN-UHFFFAOYSA-N 0.000 claims description 2
• GRRYTQYWUZQUGF-UHFFFAOYSA-N 3-[1-[2-[2-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]ethoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOCCN(CC1)CCN1CC1=CC=C(F)C=C1 GRRYTQYWUZQUGF-UHFFFAOYSA-N 0.000 claims description 2
• IBTZOZFOSJIKHR-UHFFFAOYSA-N 3-[1-[2-[2-[bis(2-hydroxypropyl)amino]ethoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCN(CC(O)C)CC(C)O)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 IBTZOZFOSJIKHR-UHFFFAOYSA-N 0.000 claims description 2
• VMGNGHPSRHKJQO-UHFFFAOYSA-N 3-[1-[2-[3-(dimethylamino)propoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOCCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 VMGNGHPSRHKJQO-UHFFFAOYSA-N 0.000 claims description 2
• JYVRKCPNBHCJKK-UHFFFAOYSA-N 3-[1-[2-[3-(hydroxymethyl)piperidin-1-yl]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCN1CCCC(CO)C1 JYVRKCPNBHCJKK-UHFFFAOYSA-N 0.000 claims description 2
• PFZKPFSSBOWHJZ-UHFFFAOYSA-N 3-[1-[2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(C)CCN1C1CCN(CCS(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 PFZKPFSSBOWHJZ-UHFFFAOYSA-N 0.000 claims description 2
• GIKBRDGAQMZVFA-UHFFFAOYSA-N 3-[1-[2-[4-(4-methylpiperidin-1-yl)piperidin-1-yl]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CC(C)CCN1C1CCN(CCS(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 GIKBRDGAQMZVFA-UHFFFAOYSA-N 0.000 claims description 2
• RHDQGZBTANGHEX-QGZVFWFLSA-N 3-[1-[2-[[(2r)-1-hydroxypropan-2-yl]amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical class C1CN(S(=O)(=O)CCN[C@@H](CO)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 RHDQGZBTANGHEX-QGZVFWFLSA-N 0.000 claims description 2
• DHWMQRGFDRDFQM-QHCPKHFHSA-N 3-[1-[2-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CN1CCC[C@H]1COCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 DHWMQRGFDRDFQM-QHCPKHFHSA-N 0.000 claims description 2
• VIKROZVATDSCBX-NRFANRHFSA-N 3-[1-[2-[[(2s)-5-oxopyrrolidin-2-yl]methoxy]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCOC[C@@H]1CCC(=O)N1 VIKROZVATDSCBX-NRFANRHFSA-N 0.000 claims description 2
• ZILIVUQYCKWNTR-UHFFFAOYSA-N 3-[1-[2-[hydroxy(methyl)amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 ZILIVUQYCKWNTR-UHFFFAOYSA-N 0.000 claims description 2
• ZVGUHFQTQPPPHA-UHFFFAOYSA-N 3-[1-[2-[methoxy(methyl)amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)OC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 ZVGUHFQTQPPPHA-UHFFFAOYSA-N 0.000 claims description 2
• APPUAZCBCWBAAV-UHFFFAOYSA-N 3-[1-[3-(1,3-benzodioxol-5-yloxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1C=2C(C3CCN(CC3)S(=O)(=O)CCCOC=3C=C4OCOC4=CC=3)=CNC=2C(C(=O)N)=CC=1C1=CC=CC=C1 APPUAZCBCWBAAV-UHFFFAOYSA-N 0.000 claims description 2
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• DLQRWYXOPVNCOL-UHFFFAOYSA-N 3-[1-[3-(2,6-dimethylmorpholin-4-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1C(C)OC(C)CN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 DLQRWYXOPVNCOL-UHFFFAOYSA-N 0.000 claims description 2
• YLUWBYPDBISKDI-UHFFFAOYSA-N 3-[1-[3-(2-acetamido-4-methylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC(=O)NC1=CC(C)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 YLUWBYPDBISKDI-UHFFFAOYSA-N 0.000 claims description 2
• HMVPYWMBQHIQJO-UHFFFAOYSA-N 3-[1-[3-(2-acetamido-5-methylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC(=O)NC1=CC=C(C)C=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 HMVPYWMBQHIQJO-UHFFFAOYSA-N 0.000 claims description 2
• GVERBRYAVNAYLM-UHFFFAOYSA-N 3-[1-[3-(2-acetamidophenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC(=O)NC1=CC=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 GVERBRYAVNAYLM-UHFFFAOYSA-N 0.000 claims description 2
• GDMXQMISCQJXPE-UHFFFAOYSA-N 3-[1-[3-(2-ethylpiperidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CCC1CCCCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 GDMXQMISCQJXPE-UHFFFAOYSA-N 0.000 claims description 2
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• VLMSTVINYRSQPK-UHFFFAOYSA-N 3-[1-[3-(2-methoxyphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound COC1=CC=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 VLMSTVINYRSQPK-UHFFFAOYSA-N 0.000 claims description 2
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• FQSZNOUOTPDYSL-UHFFFAOYSA-N 3-[1-[3-(2-methylsulfonylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 FQSZNOUOTPDYSL-UHFFFAOYSA-N 0.000 claims description 2
• KECWBIDBYDHJDS-UHFFFAOYSA-N 3-[1-[3-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1C=2C(C3CCN(CC3)S(=O)(=O)CCCN3C4CCCCC4CCC3)=CNC=2C(C(=O)N)=CC=1C1=CC=CC=C1 KECWBIDBYDHJDS-UHFFFAOYSA-N 0.000 claims description 2
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• SCIGSSSXMNXEGH-UHFFFAOYSA-N 3-[1-[3-(3-aminopyrrolidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1C(N)CCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 SCIGSSSXMNXEGH-UHFFFAOYSA-N 0.000 claims description 2
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• FAQGXHOMUBHUQT-UHFFFAOYSA-N 3-[1-[3-(3-hydroxyphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOC1=CC=CC(O)=C1 FAQGXHOMUBHUQT-UHFFFAOYSA-N 0.000 claims description 2
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• QRVHYGHNTUTSES-UHFFFAOYSA-N 3-[1-[3-(3-methylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CC1=CC=CC(OCCCS(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)=C1 QRVHYGHNTUTSES-UHFFFAOYSA-N 0.000 claims description 2
• XKTBITZFKXPKRT-UHFFFAOYSA-N 3-[1-[3-(4-acetamidophenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 XKTBITZFKXPKRT-UHFFFAOYSA-N 0.000 claims description 2
• HSYGAUDIMBTSDP-UHFFFAOYSA-N 3-[1-[3-(4-benzylpiperidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN(CC1)CCC1CC1=CC=CC=C1 HSYGAUDIMBTSDP-UHFFFAOYSA-N 0.000 claims description 2
• JKSFSWDOGZIMEQ-UHFFFAOYSA-N 3-[1-[3-(4-carbamoylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 JKSFSWDOGZIMEQ-UHFFFAOYSA-N 0.000 claims description 2
• YPUIFLAXTSTARU-UHFFFAOYSA-N 3-[1-[3-(4-carbamoylpiperidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CC(C(=O)N)CCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 YPUIFLAXTSTARU-UHFFFAOYSA-N 0.000 claims description 2
• GZNQKIYKCODNDL-UHFFFAOYSA-N 3-[1-[3-(4-ethoxyphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(OCC)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 GZNQKIYKCODNDL-UHFFFAOYSA-N 0.000 claims description 2
• RAQNWQUGBIMKBT-UHFFFAOYSA-N 3-[1-[3-(4-fluorophenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOC1=CC=C(F)C=C1 RAQNWQUGBIMKBT-UHFFFAOYSA-N 0.000 claims description 2
• CHHUYGMDEDHQSD-UHFFFAOYSA-N 3-[1-[3-(4-hydroxybutoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C1CCN(S(=O)(=O)CCCOCCCCO)CC1 CHHUYGMDEDHQSD-UHFFFAOYSA-N 0.000 claims description 2
• KVHKDDKCJDZLJH-UHFFFAOYSA-N 3-[1-[3-(4-hydroxyphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOC1=CC=C(O)C=C1 KVHKDDKCJDZLJH-UHFFFAOYSA-N 0.000 claims description 2
• DTAFFUJYABPFMJ-UHFFFAOYSA-N 3-[1-[3-(4-hydroxypiperidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCC(O)CC1 DTAFFUJYABPFMJ-UHFFFAOYSA-N 0.000 claims description 2
• JFOBGCJOGHVMAP-UHFFFAOYSA-N 3-[1-[3-(4-methoxyphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(OC)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 JFOBGCJOGHVMAP-UHFFFAOYSA-N 0.000 claims description 2
• MVYGVFXPSURHCQ-UHFFFAOYSA-N 3-[1-[3-(4-methylphenoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 MVYGVFXPSURHCQ-UHFFFAOYSA-N 0.000 claims description 2
• NEDKHGOUDJXRNM-UHFFFAOYSA-N 3-[1-[3-(cyclobutylmethoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOCC1CCC1 NEDKHGOUDJXRNM-UHFFFAOYSA-N 0.000 claims description 2
• HYSOSSCQWVIBMM-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-5-(3,4-difluorophenyl)-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(F)C(F)=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCNC1CCCC1 HYSOSSCQWVIBMM-UHFFFAOYSA-N 0.000 claims description 2
• ICANIJOGXYUXFR-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-5-(4-ethylphenyl)-1h-indole-7-carboxamide Chemical compound C1=CC(CC)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CCCNC3CCCC3)C2=C1 ICANIJOGXYUXFR-UHFFFAOYSA-N 0.000 claims description 2
• YAROUKMQJHKZCD-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-5-[3-(hydroxymethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(CO)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCNC1CCCC1 YAROUKMQJHKZCD-UHFFFAOYSA-N 0.000 claims description 2
• OLEDQBARMSYNFW-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-5-[4-(dimethylamino)phenyl]-1h-indole-7-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CCCNC3CCCC3)C2=C1 OLEDQBARMSYNFW-UHFFFAOYSA-N 0.000 claims description 2
• XQIGPOYHURHPMV-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCNC1CCCC1 XQIGPOYHURHPMV-UHFFFAOYSA-N 0.000 claims description 2
• RVRAUXRNFFBRHZ-UHFFFAOYSA-N 3-[1-[3-(cyclopropylmethoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOCC1CC1 RVRAUXRNFFBRHZ-UHFFFAOYSA-N 0.000 claims description 2
• GNZHOFWFANDVTA-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-(3-methylsulfonylphenyl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(C=CC=3)S(C)(=O)=O)C=C12 GNZHOFWFANDVTA-UHFFFAOYSA-N 0.000 claims description 2
• ZMKHXHQWEIGYFJ-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-(4-methylphenyl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(C)=CC=3)C=C12 ZMKHXHQWEIGYFJ-UHFFFAOYSA-N 0.000 claims description 2
• ZHPJORBELCIREP-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-[3-(methylaminomethyl)phenyl]-1h-indole-7-carboxamide Chemical compound CNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN(C)C)=CNC3=C(C(N)=O)C=2)=C1 ZHPJORBELCIREP-UHFFFAOYSA-N 0.000 claims description 2
• ONLBNIYLJOZSRJ-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-[3-[(propan-2-ylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound CC(C)NCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN(C)C)=CNC3=C(C(N)=O)C=2)=C1 ONLBNIYLJOZSRJ-UHFFFAOYSA-N 0.000 claims description 2
• ONNBUDSOGWDPRH-FQEVSTJZSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-[3-[[[(2s)-1-hydroxypropan-2-yl]amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound OC[C@H](C)NCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN(C)C)=CNC3=C(C(N)=O)C=2)=C1 ONNBUDSOGWDPRH-FQEVSTJZSA-N 0.000 claims description 2
• GZFHHFZOKLATNI-FQEVSTJZSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-[3-[[[(2s)-2-hydroxypropyl]amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C[C@H](O)CNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN(C)C)=CNC3=C(C(N)=O)C=2)=C1 GZFHHFZOKLATNI-FQEVSTJZSA-N 0.000 claims description 2
• FTVCTUVOGPNMLH-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-[4-(hydroxymethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(CO)=CC=3)C=C12 FTVCTUVOGPNMLH-UHFFFAOYSA-N 0.000 claims description 2
• IOIPDUUKJDOPEL-UHFFFAOYSA-N 3-[1-[3-(ethoxyamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNOCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 IOIPDUUKJDOPEL-UHFFFAOYSA-N 0.000 claims description 2
• VUUUWDRLYXMHFX-UHFFFAOYSA-N 3-[1-[3-(oxolan-3-ylmethoxy)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOCC1CCOC1 VUUUWDRLYXMHFX-UHFFFAOYSA-N 0.000 claims description 2
• HWGIMJRGIIZHNM-RUZDIDTESA-N 3-[1-[3-[(2r)-2-carbamoylpyrrolidin-1-yl]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound NC(=O)[C@H]1CCCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 HWGIMJRGIIZHNM-RUZDIDTESA-N 0.000 claims description 2
• UYWPJPXZKCDSIA-DEOSSOPVSA-N 3-[1-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound COC[C@@H]1CCCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 UYWPJPXZKCDSIA-DEOSSOPVSA-N 0.000 claims description 2
• FVMRWURANWWXHI-UHFFFAOYSA-N 3-[1-[3-[2-[(dimethylamino)methyl]phenoxy]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CN(C)CC1=CC=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 FVMRWURANWWXHI-UHFFFAOYSA-N 0.000 claims description 2
• LVGYVPZRUGLKRM-UHFFFAOYSA-N 3-[1-[3-[2-fluoro-3-(trifluoromethyl)phenoxy]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCOC1=CC=CC(C(F)(F)F)=C1F LVGYVPZRUGLKRM-UHFFFAOYSA-N 0.000 claims description 2
• ABRXNKBKUQAMSJ-UHFFFAOYSA-N 3-[1-[3-[3-(diethylamino)phenoxy]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CCN(CC)C1=CC=CC(OCCCS(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)=C1 ABRXNKBKUQAMSJ-UHFFFAOYSA-N 0.000 claims description 2
• VGDMNYLBFGAPQW-UHFFFAOYSA-N 3-[1-[3-[3-(dimethylamino)phenoxy]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CN(C)C1=CC=CC(OCCCS(=O)(=O)N2CCC(CC2)C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)=C1 VGDMNYLBFGAPQW-UHFFFAOYSA-N 0.000 claims description 2
• FGCLGMHRHUSZBS-UHFFFAOYSA-N 3-[1-[3-[3-(hydroxymethyl)piperidin-1-yl]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC(CO)C1 FGCLGMHRHUSZBS-UHFFFAOYSA-N 0.000 claims description 2
• YBUWROKZDQOWCS-UHFFFAOYSA-N 3-[1-[3-[4-(4-acetylpiperazin-1-yl)phenoxy]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OCCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 YBUWROKZDQOWCS-UHFFFAOYSA-N 0.000 claims description 2
• BNJFRISSGHZWSU-UHFFFAOYSA-N 3-[1-[3-[bis(2-methoxyethyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(CCOC)CCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 BNJFRISSGHZWSU-UHFFFAOYSA-N 0.000 claims description 2
• CFBLJFZURPNKSD-UHFFFAOYSA-N 3-[1-[3-[ethyl(2-methoxyethyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(CC)CCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 CFBLJFZURPNKSD-UHFFFAOYSA-N 0.000 claims description 2
• PMRVVDHGGWLBMZ-UHFFFAOYSA-N 3-[1-[3-[ethyl(methyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 PMRVVDHGGWLBMZ-UHFFFAOYSA-N 0.000 claims description 2
• LDFWTSKLFLYETH-UHFFFAOYSA-N 3-[1-[3-[ethyl(propan-2-yl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(CC)C(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 LDFWTSKLFLYETH-UHFFFAOYSA-N 0.000 claims description 2
• CENJFZKQTMNQKZ-UHFFFAOYSA-N 3-[1-[3-[furan-2-ylmethyl(methyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1C=COC=1CN(C)CCCS(=O)(=O)N(CC1)CCC1C(C1=C2)=CNC1=C(C(N)=O)C=C2C1=CC=CC=C1 CENJFZKQTMNQKZ-UHFFFAOYSA-N 0.000 claims description 2
• HJMVJBYWYWHJJU-UHFFFAOYSA-N 3-[1-[3-[hydroxy(methyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 HJMVJBYWYWHJJU-UHFFFAOYSA-N 0.000 claims description 2
• YXLZVGKFYWYGOJ-UHFFFAOYSA-N 3-[1-[3-[methoxy(methyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)OC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 YXLZVGKFYWYGOJ-UHFFFAOYSA-N 0.000 claims description 2
• FONDWNJZFYDGHJ-UHFFFAOYSA-N 3-[1-[3-[methyl(prop-2-ynyl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)CC#C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 FONDWNJZFYDGHJ-UHFFFAOYSA-N 0.000 claims description 2
• IHNYWBMMUNGVEK-UHFFFAOYSA-N 3-[1-[3-[methyl(propan-2-yl)amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 IHNYWBMMUNGVEK-UHFFFAOYSA-N 0.000 claims description 2
• AXQKVAGVZDWPPT-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[3-(cyclopentylamino)propylsulfonyl]piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(Cl)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCNC1CCCC1 AXQKVAGVZDWPPT-UHFFFAOYSA-N 0.000 claims description 2
• WSYRSRCHCXWHPR-UHFFFAOYSA-N 5-(4-acetamidophenyl)-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CCCN3CCCC3)C2=C1 WSYRSRCHCXWHPR-UHFFFAOYSA-N 0.000 claims description 2
• DFUBXBUIHYNWIV-UHFFFAOYSA-N 5-[3-(ethylaminomethyl)phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical class CCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN4CCCC4)=CNC3=C(C(N)=O)C=2)=C1 DFUBXBUIHYNWIV-UHFFFAOYSA-N 0.000 claims description 2
• UDDGMDKONQHWTD-UHFFFAOYSA-N 5-[3-(morpholin-4-ylmethyl)phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(CN4CCOCC4)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 UDDGMDKONQHWTD-UHFFFAOYSA-N 0.000 claims description 2
• PJDIMJPRQRPVBI-UHFFFAOYSA-N 5-[3-(piperidin-1-ylmethyl)phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(CN4CCCCC4)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 PJDIMJPRQRPVBI-UHFFFAOYSA-N 0.000 claims description 2
• RAAMOYWNTUZOOO-UHFFFAOYSA-N 5-[3-(pyrrolidin-1-ylmethyl)phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(CN4CCCC4)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 RAAMOYWNTUZOOO-UHFFFAOYSA-N 0.000 claims description 2
• DBDHBWVOXLAYLS-UHFFFAOYSA-N 5-[3-[(1-hydroxypropan-2-ylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC(C)CO)C=CC=3)C=C12 DBDHBWVOXLAYLS-UHFFFAOYSA-N 0.000 claims description 2
• LRCKZHANIFDNJR-UHFFFAOYSA-N 5-[3-[(1-methoxybutan-2-ylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound COCC(CC)NCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 LRCKZHANIFDNJR-UHFFFAOYSA-N 0.000 claims description 2
• SBWLKQPWYVSJEQ-UHFFFAOYSA-N 5-[3-[(3,5-dimethylpiperidin-1-yl)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CC(C)CC(C)C4)C=CC=3)C=C12 SBWLKQPWYVSJEQ-UHFFFAOYSA-N 0.000 claims description 2
• JUDAVKNURNHLHQ-UHFFFAOYSA-N 5-[3-[(3-imidazol-1-ylpropylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCCCN4C=NC=C4)C=CC=3)C=C12 JUDAVKNURNHLHQ-UHFFFAOYSA-N 0.000 claims description 2
• GFAPXYHGJNFXIC-UHFFFAOYSA-N 5-[3-[(cyclopentylamino)methyl]phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=C(CNC4CCCC4)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 GFAPXYHGJNFXIC-UHFFFAOYSA-N 0.000 claims description 2
• SJUBSAJCRPWJER-UHFFFAOYSA-N 5-[3-[(propan-2-ylamino)methyl]phenyl]-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound CC(C)NCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCN4CCCC4)=CNC3=C(C(N)=O)C=2)=C1 SJUBSAJCRPWJER-UHFFFAOYSA-N 0.000 claims description 2
• QHAMHPXCSDCTJV-UHFFFAOYSA-N 5-[3-[(tert-butylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC(C)(C)C)C=CC=3)C=C12 QHAMHPXCSDCTJV-UHFFFAOYSA-N 0.000 claims description 2
• HOJLYQQDRPTMSI-MHZLTWQESA-N 5-[3-[[(2s)-2-carbamoylpyrrolidin-1-yl]methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4[C@@H](CCC4)C(N)=O)C=CC=3)C=C12 HOJLYQQDRPTMSI-MHZLTWQESA-N 0.000 claims description 2
• VTARWGFWGFAHMK-UHFFFAOYSA-N 5-[3-[[2-hydroxyethyl(propyl)amino]methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound CCCN(CCO)CC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 VTARWGFWGFAHMK-UHFFFAOYSA-N 0.000 claims description 2
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