JP2008513500A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008513500A5 JP2008513500A5 JP2007532632A JP2007532632A JP2008513500A5 JP 2008513500 A5 JP2008513500 A5 JP 2008513500A5 JP 2007532632 A JP2007532632 A JP 2007532632A JP 2007532632 A JP2007532632 A JP 2007532632A JP 2008513500 A5 JP2008513500 A5 JP 2008513500A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- group
- alkyl
- substituted
- piperidinyl
- 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.)
- Pending
Links
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 101
- 125000001424 substituent group Chemical group 0.000 claims 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 80
- 125000001072 heteroaryl group Chemical group 0.000 claims 79
- 229910003827 NRaRb Inorganic materials 0.000 claims 52
- 125000005843 halogen group Chemical group 0.000 claims 51
- -1 -ORc Chemical group 0.000 claims 36
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims 34
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 28
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 5
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- JAARXRBVYNQFCZ-UHFFFAOYSA-N 2-tert-butyl-4-(7-carbamoyl-5-thiophen-2-yl-1H-indol-3-yl)piperidine-1-carboxylic acid Chemical compound C1CN(C(O)=O)C(C(C)(C)C)CC1C1=CNC2=C(C(N)=O)C=C(C=3SC=CC=3)C=C12 JAARXRBVYNQFCZ-UHFFFAOYSA-N 0.000 claims 1
- LHEWMBUFYLDXRR-UHFFFAOYSA-N 2-tert-butyl-4-(7-carbamoyl-5-thiophen-3-yl-1H-indol-3-yl)piperidine-1-carboxylic acid Chemical compound C1CN(C(O)=O)C(C(C)(C)C)CC1C1=CNC2=C(C(N)=O)C=C(C3=CSC=C3)C=C12 LHEWMBUFYLDXRR-UHFFFAOYSA-N 0.000 claims 1
- OZMCVPNASJLVTM-UHFFFAOYSA-N 3-(1-ethenylsulfonylpiperidin-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)C=C)CC1 OZMCVPNASJLVTM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FSMXULRZWBGMAR-UHFFFAOYSA-N 3-[1-(2-chloroethylsulfonyl)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)CCCl)CC1 FSMXULRZWBGMAR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- FGZOAPSCWGEAHY-UHFFFAOYSA-N 3-[1-(3-chloropropylsulfonyl)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)CCCCl)CC1 FGZOAPSCWGEAHY-UHFFFAOYSA-N 0.000 claims 1
- XSEDYBNFRPWUPE-UHFFFAOYSA-N 3-[1-(3-chloropropylsulfonyl)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=1C1CCN(S(=O)(=O)CCCCl)CC1 XSEDYBNFRPWUPE-UHFFFAOYSA-N 0.000 claims 1
- DSRKFMRGYRGPOQ-UHFFFAOYSA-N 3-[1-(3-chloropropylsulfonyl)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=1C1CCN(S(=O)(=O)CCCCl)CC1 DSRKFMRGYRGPOQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RETBTQNBVBDKHK-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-[3-[[(5-methylfuran-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(CNCC=4OC(C)=CC=4)C=CC=3)C=C12 RETBTQNBVBDKHK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- JKEGWZMIZMRIBD-UHFFFAOYSA-N 3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3SC=CC=3)C=C12 JKEGWZMIZMRIBD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JKFFFTQGEYSOEU-UHFFFAOYSA-N 3-[1-(3-pyrrolidin-1-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)CCCN1CCCC1 JKFFFTQGEYSOEU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZFDXHNNDKIRZON-UHFFFAOYSA-N 3-[1-[2-(4-hydroxypiperidin-1-yl)ethylsulfonyl]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)CCN1CCC(O)CC1 ZFDXHNNDKIRZON-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LCCBWWBXSIGSMS-UHFFFAOYSA-N 3-[1-[2-(azepan-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)CCN1CCCCCC1 LCCBWWBXSIGSMS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WGJGKCAGQVPEGN-UHFFFAOYSA-N 3-[1-[2-(cyclopentylamino)ethylsulfonyl]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)CCNC1CCCC1 WGJGKCAGQVPEGN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- LUYYCKBSMDOEDG-UHFFFAOYSA-N 3-[1-[2-(ethylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCNCC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 LUYYCKBSMDOEDG-UHFFFAOYSA-N 0.000 claims 1
- VHAKGAMMAGIEMZ-UHFFFAOYSA-N 3-[1-[2-(methylamino)ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCNC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 VHAKGAMMAGIEMZ-UHFFFAOYSA-N 0.000 claims 1
- XWJWBZVRUFRHKL-QFIPXVFZSA-N 3-[1-[2-[(2s)-2-(hydroxymethyl)pyrrolidin-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[C@H]1CO XWJWBZVRUFRHKL-QFIPXVFZSA-N 0.000 claims 1
- TZOXXHAVFRVKIG-DEOSSOPVSA-N 3-[1-[2-[(2s)-2-carbamoylpyrrolidin-1-yl]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1CCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 TZOXXHAVFRVKIG-DEOSSOPVSA-N 0.000 claims 1
- LTJSKCCXLGVNJM-UHFFFAOYSA-N 3-[1-[2-[2-(dimethylcarbamoyl)pyrrolidin-1-yl]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound CN(C)C(=O)C1CCCN1CCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 LTJSKCCXLGVNJM-UHFFFAOYSA-N 0.000 claims 1
- ZEFMFHWTSYWKAK-UHFFFAOYSA-N 3-[1-[2-[3-(dimethylamino)propyl-methylamino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 ZEFMFHWTSYWKAK-UHFFFAOYSA-N 0.000 claims 1
- WQLYHIYMXDUZJF-UHFFFAOYSA-N 3-[1-[2-[4-(2-hydroxyethyl)piperazin-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)CCN1CCN(CCO)CC1 WQLYHIYMXDUZJF-UHFFFAOYSA-N 0.000 claims 1
- FSZYSJLGKAGYRP-UHFFFAOYSA-N 3-[1-[2-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-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)CCN(CC1)CCN1CC(=O)N1CCCC1 FSZYSJLGKAGYRP-UHFFFAOYSA-N 0.000 claims 1
- RHDQGZBTANGHEX-KRWDZBQOSA-N 3-[1-[2-[[(2s)-1-hydroxypropan-2-yl]amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound 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-KRWDZBQOSA-N 0.000 claims 1
- BBMSLOZFILFLPG-KRWDZBQOSA-N 3-[1-[2-[[(2s)-2-hydroxypropyl]amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCNC[C@@H](O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 BBMSLOZFILFLPG-KRWDZBQOSA-N 0.000 claims 1
- LWPHSCRMOFFNKZ-UHFFFAOYSA-N 3-[1-[2-[ethyl(methyl)amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 LWPHSCRMOFFNKZ-UHFFFAOYSA-N 0.000 claims 1
- IZSJQTKUDBBFSR-UHFFFAOYSA-N 3-[1-[2-[methyl-[2-(methylamino)ethyl]amino]ethylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCN(C)CCNC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 IZSJQTKUDBBFSR-UHFFFAOYSA-N 0.000 claims 1
- HPDWVZPBSHSNQF-UHFFFAOYSA-N 3-[1-[3-(1-hydroxypropan-2-ylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNC(CO)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 HPDWVZPBSHSNQF-UHFFFAOYSA-N 0.000 claims 1
- MORTZTRVMUQYGI-UHFFFAOYSA-N 3-[1-[3-(1-methoxypropan-2-ylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNC(C)COC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 MORTZTRVMUQYGI-UHFFFAOYSA-N 0.000 claims 1
- JRSNJFBHEILWNZ-UHFFFAOYSA-N 3-[1-[3-(2-hydroxybutylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNCC(O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 JRSNJFBHEILWNZ-UHFFFAOYSA-N 0.000 claims 1
- PKCYLBBPQOCAQS-UHFFFAOYSA-N 3-[1-[3-(2-hydroxypropylamino)propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNCC(O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 PKCYLBBPQOCAQS-UHFFFAOYSA-N 0.000 claims 1
- VRXVNIYQUOWFOB-UHFFFAOYSA-N 3-[1-[3-(2-methylpyrrolidin-1-yl)propylsulfonyl]piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound CC1CCCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2SC=CC=2)CC1 VRXVNIYQUOWFOB-UHFFFAOYSA-N 0.000 claims 1
- WGOPFNFAVMYIBW-UHFFFAOYSA-N 3-[1-[3-(3-hydroxypyrrolidin-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)C1 WGOPFNFAVMYIBW-UHFFFAOYSA-N 0.000 claims 1
- GPCALZUGZQXFIU-UHFFFAOYSA-N 3-[1-[3-(4-hydroxypiperidin-1-yl)propylsulfonyl]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)CCCN1CCC(O)CC1 GPCALZUGZQXFIU-UHFFFAOYSA-N 0.000 claims 1
- ZMIODWQUEQJQRY-UHFFFAOYSA-N 3-[1-[3-(4-methylpiperazin-1-yl)propylsulfonyl]piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C1CN(C)CCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2SC=CC=2)CC1 ZMIODWQUEQJQRY-UHFFFAOYSA-N 0.000 claims 1
- LBTSTCOTIVCLFQ-UHFFFAOYSA-N 3-[1-[3-(4-methylpiperazin-1-yl)propylsulfonyl]piperidin-4-yl]-5-thiophen-3-yl-1h-indole-7-carboxamide Chemical compound C1CN(C)CCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C2=CSC=C2)CC1 LBTSTCOTIVCLFQ-UHFFFAOYSA-N 0.000 claims 1
- RZYUQVVDRRDXNT-UHFFFAOYSA-N 3-[1-[3-(azepan-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)CCCN1CCCCCC1 RZYUQVVDRRDXNT-UHFFFAOYSA-N 0.000 claims 1
- ZUVKDXRTARJACU-UHFFFAOYSA-N 3-[1-[3-(cyclohexylamino)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)CCCNC1CCCCC1 ZUVKDXRTARJACU-UHFFFAOYSA-N 0.000 claims 1
- IFOVPMIWVNNDJB-UHFFFAOYSA-N 3-[1-[3-(cyclopentylamino)propylsulfonyl]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)CCCNC1CCCC1 IFOVPMIWVNNDJB-UHFFFAOYSA-N 0.000 claims 1
- XOMOJYZAVDKQPK-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-(1h-pyrazol-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C3=CNN=C3)C=C12 XOMOJYZAVDKQPK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VVRGLRJOJQZVQK-UHFFFAOYSA-N 3-[1-[3-(dimethylamino)propylsulfonyl]piperidin-4-yl]-5-thiophen-2-yl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3SC=CC=3)C=C12 VVRGLRJOJQZVQK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KBJCTUCNQIVVEZ-QHCPKHFHSA-N 3-[1-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-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[C@H]1CO KBJCTUCNQIVVEZ-QHCPKHFHSA-N 0.000 claims 1
- VVEGLBSSFBTRMD-UHFFFAOYSA-N 3-[1-[3-[2-(dimethylamino)ethylamino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNCCN(C)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 VVEGLBSSFBTRMD-UHFFFAOYSA-N 0.000 claims 1
- BYMFOMFPRKSKSS-UHFFFAOYSA-N 3-[1-[3-[2-(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)CCCN1CCCCC1CO BYMFOMFPRKSKSS-UHFFFAOYSA-N 0.000 claims 1
- KLZUVMOFUKTEHD-UHFFFAOYSA-N 3-[1-[3-[4-[2-oxo-2-(propan-2-ylamino)ethyl]piperazin-1-yl]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1CCCS(=O)(=O)N1CCC(C=2C3=CC(=CC(=C3NC=2)C(N)=O)C=2C=CC=CC=2)CC1 KLZUVMOFUKTEHD-UHFFFAOYSA-N 0.000 claims 1
- PKCYLBBPQOCAQS-GOSISDBHSA-N 3-[1-[3-[[(2r)-2-hydroxypropyl]amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCNC[C@H](O)C)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 PKCYLBBPQOCAQS-GOSISDBHSA-N 0.000 claims 1
- MUJZYJFTWFRVDN-QFIPXVFZSA-N 3-[1-[3-[[(2s)-1-hydroxybutan-2-yl]amino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCCN[C@H](CO)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC=CC=3)C=C12 MUJZYJFTWFRVDN-QFIPXVFZSA-N 0.000 claims 1
- CJZJGQBLYAHNHA-UHFFFAOYSA-N 3-[1-[3-[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methylamino]propylsulfonyl]piperidin-4-yl]-5-phenyl-1h-indole-7-carboxamide Chemical compound C=1C=C(O)C=CC=1C(O)CN(C)CCCS(=O)(=O)N(CC1)CCC1C(C1=C2)=CNC1=C(C(N)=O)C=C2C1=CC=CC=C1 CJZJGQBLYAHNHA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FNCPPPMDFONPFE-UHFFFAOYSA-N 3-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=1C1CCNCC1 FNCPPPMDFONPFE-UHFFFAOYSA-N 0.000 claims 1
- WTEAZAGTFXNGBW-UHFFFAOYSA-N 3-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=1C1CCNCC1 WTEAZAGTFXNGBW-UHFFFAOYSA-N 0.000 claims 1
- PBNMPFZODQRVNT-UHFFFAOYSA-N 5-(3-formylphenyl)-3-[1-(2-methoxyethylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(C=O)C=CC=3)C=C12 PBNMPFZODQRVNT-UHFFFAOYSA-N 0.000 claims 1
- YSQWJVBWJPQJPY-UHFFFAOYSA-N 5-(3-formylphenyl)-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(C=O)C=CC=3)C=C12 YSQWJVBWJPQJPY-UHFFFAOYSA-N 0.000 claims 1
- FULAGCPTSQZALE-UHFFFAOYSA-N 5-(4-fluorophenyl)-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(F)=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 FULAGCPTSQZALE-UHFFFAOYSA-N 0.000 claims 1
- YWPJTAUOKIPHEK-UHFFFAOYSA-N 5-(4-methylphenyl)-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CCCN3CCCC3)C2=C1 YWPJTAUOKIPHEK-UHFFFAOYSA-N 0.000 claims 1
- RQNOFUHMSWQMJM-UHFFFAOYSA-N 5-(5-chlorothiophen-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(Cl)=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 RQNOFUHMSWQMJM-UHFFFAOYSA-N 0.000 claims 1
- CBYQDSQGZQSPML-UHFFFAOYSA-N 5-(5-formylthiophen-3-yl)-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(C=O)SC=3)C=C12 CBYQDSQGZQSPML-UHFFFAOYSA-N 0.000 claims 1
- WZZDKHXGPNPARU-UHFFFAOYSA-N 5-[3-(ethylaminomethyl)phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound CCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 WZZDKHXGPNPARU-UHFFFAOYSA-N 0.000 claims 1
- PDGOXJPIYZSOGH-UHFFFAOYSA-N 5-[3-(hydroxymethyl)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(CO)C=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 PDGOXJPIYZSOGH-UHFFFAOYSA-N 0.000 claims 1
- XDIUYHMEFOQEDV-UHFFFAOYSA-N 5-[3-[(1-methoxypropan-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)COC)C=CC=3)C=C12 XDIUYHMEFOQEDV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IJJLIVKMCYRTPB-UHFFFAOYSA-N 5-[3-[(2-ethoxyethylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound CCOCCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 IJJLIVKMCYRTPB-UHFFFAOYSA-N 0.000 claims 1
- DIHOWXVDCCQBSI-UHFFFAOYSA-N 5-[3-[(2-methoxyethylamino)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(CNCCOC)C=CC=3)C=C12 DIHOWXVDCCQBSI-UHFFFAOYSA-N 0.000 claims 1
- WPBSCWQTEGSFRF-UHFFFAOYSA-N 5-[3-[(3-methoxypropylamino)methyl]phenyl]-3-[1-(3-methoxypropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound COCCCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CCCOC)=CNC3=C(C(N)=O)C=2)=C1 WPBSCWQTEGSFRF-UHFFFAOYSA-N 0.000 claims 1
- WOJPDCUKFATTGA-UHFFFAOYSA-N 5-[3-[(cyclopropylmethylamino)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(CNCC4CC4)C=CC=3)C=C12 WOJPDCUKFATTGA-UHFFFAOYSA-N 0.000 claims 1
- YYERDCDGVHQVMR-XMMPIXPASA-N 5-[3-[[(3r)-3-hydroxypyrrolidin-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(CN4C[C@H](O)CC4)C=CC=3)C=C12 YYERDCDGVHQVMR-XMMPIXPASA-N 0.000 claims 1
- JTIVLGNSVMPNJY-NRFANRHFSA-N 5-[3-[[[(2s)-3,3-dimethylbutan-2-yl]amino]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(CN[C@@H](C)C(C)(C)C)C=CC=3)C=C12 JTIVLGNSVMPNJY-NRFANRHFSA-N 0.000 claims 1
- MQJLOOMFYYDRCY-UHFFFAOYSA-N 5-[5-(hydroxymethyl)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(CO)=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 MQJLOOMFYYDRCY-UHFFFAOYSA-N 0.000 claims 1
- JLCDFUFAQXYXGR-UHFFFAOYSA-N 5-bromo-3-(1-ethenylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(Br)=CC=2C=1C1CCN(S(=O)(=O)C=C)CC1 JLCDFUFAQXYXGR-UHFFFAOYSA-N 0.000 claims 1
- DLDFITGBQJJTFD-UHFFFAOYSA-N 5-bromo-3-[1-(2-methoxyethylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CCOC)CCC1C1=CNC2=C(C(N)=O)C=C(Br)C=C12 DLDFITGBQJJTFD-UHFFFAOYSA-N 0.000 claims 1
- ZUTPMWWVFOHPDM-UHFFFAOYSA-N 5-bromo-3-[1-(3-chloropropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(Br)=CC=2C=1C1CCN(S(=O)(=O)CCCCl)CC1 ZUTPMWWVFOHPDM-UHFFFAOYSA-N 0.000 claims 1
- PVMQSBIBQIJHPA-UHFFFAOYSA-N 5-bromo-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(Br)C=C12 PVMQSBIBQIJHPA-UHFFFAOYSA-N 0.000 claims 1
- IDCYBVZCFZIBFR-UHFFFAOYSA-N 5-bromo-3-[1-(3-morpholin-4-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(Br)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCOCC1 IDCYBVZCFZIBFR-UHFFFAOYSA-N 0.000 claims 1
- AJOJYXJQBSYAHU-UHFFFAOYSA-N 5-bromo-3-[1-(3-pyrrolidin-1-ylpropylsulfonyl)piperidin-4-yl]-1h-indole-7-carboxamide Chemical compound C=1NC=2C(C(=O)N)=CC(Br)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN1CCCC1 AJOJYXJQBSYAHU-UHFFFAOYSA-N 0.000 claims 1
- BNDWZKXEDJIHKQ-UHFFFAOYSA-N 5-phenyl-3-[1-(2-piperidin-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)CCN1CCCCC1 BNDWZKXEDJIHKQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FFARPIKHOHKEMS-UHFFFAOYSA-N 5-phenyl-3-[1-[2-(2-pyrrolidin-1-ylethoxy)ethylsulfonyl]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)CCOCCN1CCCC1 FFARPIKHOHKEMS-UHFFFAOYSA-N 0.000 claims 1
- MUYPXSKLACAXLI-UHFFFAOYSA-N 5-phenyl-3-[1-[2-(4-piperidin-1-ylpiperidin-1-yl)ethylsulfonyl]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)CCN(CC1)CCC1N1CCCCC1 MUYPXSKLACAXLI-UHFFFAOYSA-N 0.000 claims 1
- MQOUIEQCPDGTEL-UHFFFAOYSA-N 5-phenyl-3-[1-[3-(4-piperidin-1-ylpiperidin-1-yl)propylsulfonyl]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)CCCN(CC1)CCC1N1CCCCC1 MQOUIEQCPDGTEL-UHFFFAOYSA-N 0.000 claims 1
- ZSRPBQJDHXCBGL-RQNOJGIXSA-N C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN[C@H]1CC[C@H](O)CC1 Chemical compound C=1NC=2C(C(=O)N)=CC(C=3C=CC=CC=3)=CC=2C=1C(CC1)CCN1S(=O)(=O)CCCN[C@H]1CC[C@H](O)CC1 ZSRPBQJDHXCBGL-RQNOJGIXSA-N 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61176104P | 2004-09-21 | 2004-09-21 | |
| US69545405P | 2005-06-30 | 2005-06-30 | |
| PCT/US2005/033752 WO2006034317A2 (en) | 2004-09-21 | 2005-09-21 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008513500A JP2008513500A (ja) | 2008-05-01 |
| JP2008513500A5 true JP2008513500A5 (https=) | 2008-11-06 |
Family
ID=36090636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532632A Pending JP2008513500A (ja) | 2004-09-21 | 2005-09-21 | 化学物質 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7858796B2 (https=) |
| EP (1) | EP1793826A4 (https=) |
| JP (1) | JP2008513500A (https=) |
| KR (1) | KR20070057969A (https=) |
| AR (1) | AR054084A1 (https=) |
| AU (1) | AU2005286795A1 (https=) |
| BR (1) | BRPI0515524A (https=) |
| CA (1) | CA2581180A1 (https=) |
| IL (1) | IL181877A0 (https=) |
| MA (1) | MA28912B1 (https=) |
| MX (1) | MX2007003283A (https=) |
| NO (1) | NO20071988L (https=) |
| PE (1) | PE20060748A1 (https=) |
| SG (1) | SG155932A1 (https=) |
| TW (1) | TW200626142A (https=) |
| WO (1) | WO2006034317A2 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0400895D0 (en) * | 2004-01-15 | 2004-02-18 | Smithkline Beecham Corp | Chemical compounds |
| AR050253A1 (es) * | 2004-06-24 | 2006-10-11 | Smithkline Beecham Corp | Compuesto derivado de indazol carboxamida, composicion que lo comprende y su uso para la preparacion de un medicamento |
| AR055343A1 (es) * | 2005-06-30 | 2007-08-22 | Smithkline Beecham Corp | Derivados de indolcarboxamida inhibidores de quinasas ikk2 |
| US8063071B2 (en) * | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| US20080269291A1 (en) * | 2005-11-18 | 2008-10-30 | Kerns Jeffrey K | Chemical Compounds |
| EP1959737A4 (en) * | 2005-12-16 | 2010-12-08 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS |
| TWI403320B (zh) * | 2005-12-16 | 2013-08-01 | Infinity Discovery Inc | 用於抑制ｂｃｌ蛋白和結合夥伴間之交互作用的化合物及方法 |
| PE20081889A1 (es) * | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| US8084620B2 (en) | 2008-12-19 | 2011-12-27 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| EP2370407B1 (en) * | 2008-12-19 | 2014-06-18 | Bristol-Myers Squibb Company | Carbazole and carboline kinase inhibitors |
| WO2010102968A1 (en) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| EA023788B1 (ru) | 2010-05-07 | 2016-07-29 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Производные индола и фармацевтические композиции на их основе |
| WO2011159857A1 (en) | 2010-06-16 | 2011-12-22 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| WO2014210255A1 (en) * | 2013-06-26 | 2014-12-31 | Abbvie Inc. | Primary carboxamides as btk inhibitors |
| KR102272792B1 (ko) | 2013-09-30 | 2021-07-05 | 광저우 이노케어 파마 테크 씨오., 엘티디. | Ｂｔｋ의 치환된 니코틴이미드 저해제 및 그의 제조 방법 및 암, 염증 및 자가면역 질환에의 용도 |
| PE20190710A1 (es) | 2014-10-24 | 2019-05-17 | Bristol Myers Squibb Co | Compuestos de indol carboxamida utiles como inhibidores de cinasas |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA44075A (fr) | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| JP7101678B2 (ja) | 2016-12-22 | 2022-07-15 | インサイト・コーポレイション | 免疫調節剤としての複素環式化合物 |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| SMT202500157T1 (it) | 2018-03-30 | 2025-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Ｐｄ－１／ｐｄ－ｌ１阻害剤の塩 |
| PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
| CA3160131A1 (en) | 2019-11-11 | 2021-05-20 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4775761A (en) | 1983-08-22 | 1988-10-04 | Hoechst-Roussel Pharmaceuticals, Inc. | 3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles |
| DE3342632A1 (de) | 1983-11-25 | 1985-06-05 | Merck Patent Gmbh, 6100 Darmstadt | Indolderivate |
| US5256673A (en) | 1983-11-25 | 1993-10-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Indole-3-yl-A-tetrahydropyridyl or piperidyl compounds |
| ES2059408T3 (es) | 1987-02-10 | 1994-11-16 | Abbott Lab | Un proceso para la preparacion de un compuesto. |
| IE903206A1 (en) | 1989-09-07 | 1991-03-13 | Abbott Lab | Indole-, benzofuran-, and benzothiophene-containing¹lipoxygenase-inhibiting compounds |
| US5330986A (en) * | 1992-11-24 | 1994-07-19 | Hoechst-Roussel Pharmaceuticals Inc. | Indole-7-carboxamide derivatives |
| FR2701026B1 (fr) | 1993-02-02 | 1995-03-31 | Adir | Nouveaux dérivés de l'indole, de l'indazole et du benzisoxazole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| DE19500689A1 (de) | 1995-01-12 | 1996-07-18 | Merck Patent Gmbh | Indolpiperidin-Derivate |
| US5846982A (en) | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| EP1077213A3 (en) | 1996-06-14 | 2001-06-13 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| AR013669A1 (es) | 1997-10-07 | 2001-01-10 | Smithkline Beecham Corp | Compuestos y metodos |
| DE19807993A1 (de) | 1998-02-26 | 1999-09-02 | Bayer Ag | Verwendung von ß-Carbolinderivaten zur Bekämpfung von TNF-alpha-abhängigen Krankheiten |
| ID29028A (id) * | 1998-09-18 | 2001-07-26 | Basf Ag | Pirolopirimidina sebagai penghambat protein kinase |
| DE19928424A1 (de) | 1999-06-23 | 2000-12-28 | Aventis Pharma Gmbh | Substituierte Benzimidazole |
| DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| JP2003513970A (ja) | 1999-11-08 | 2003-04-15 | ワイス | 中枢神経系障害の治療のための［（インドール−３−イル）−シクロアルキル］−３−置換アゼチジン |
| US6245799B1 (en) | 1999-11-08 | 2001-06-12 | American Home Products Corp | [(Indol-3-yl)-cycloalkyl]-3-substituted azetidines for the treatment of central nervous system disorders |
| GB0003154D0 (en) | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| EP1268477B1 (en) | 2000-03-15 | 2010-04-21 | Sanofi-Aventis Deutschland GmbH | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| EP1134221A1 (en) | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
| EP1209158A1 (en) | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
| AR028385A1 (es) | 2000-04-28 | 2003-05-07 | Acadia Pharm Inc | Agonistas muscarinicos |
| EP1293206A4 (en) | 2000-05-15 | 2005-09-21 | Kissei Pharmaceutical | LIQUID PREPARATION BASED ON WATER |
| US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| HK1052705B (en) | 2000-08-14 | 2006-09-29 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted pyrazole |
| AU2001279958A1 (en) | 2000-08-17 | 2002-03-04 | Celltech R And D Limited | Bicyclic heteroaromatic derivatives for the treatment of immune and inflammatorydisorders |
| US6369032B1 (en) | 2000-09-06 | 2002-04-09 | Ortho-Mcneil Pharmaceutical, Inc. | Method for treating allergies |
| JP4272338B2 (ja) | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
| US6869956B2 (en) | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
| CA2424303A1 (en) | 2000-10-03 | 2002-04-11 | Bristol-Myers Squibb Company | Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same |
| EP1324759A4 (en) * | 2000-10-12 | 2004-05-12 | Smithkline Beecham Corp | NF - G (K) B INHIBITORS |
| JP2004532797A (ja) | 2000-10-12 | 2004-10-28 | スミスクライン・ビーチャム・コーポレイション | ＮＦ−κＢ阻害剤 |
| ES2305125T3 (es) | 2000-10-26 | 2008-11-01 | Amgen Inc. | Agentes anti-inflamatorios. |
| JP2002193938A (ja) | 2000-12-01 | 2002-07-10 | Bayer Ag | ４−アリールピリジン誘導体 |
| US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
| WO2002051837A2 (en) | 2000-12-22 | 2002-07-04 | Wyeth | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| PL364111A1 (en) | 2001-02-01 | 2004-12-13 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of ikappab kinase (ikk) |
| DE10112151A1 (de) | 2001-03-14 | 2002-09-19 | Merck Patent Gmbh | Substituierte Benzofuran-2-carbonsäureamide |
| US20030045515A1 (en) | 2001-05-24 | 2003-03-06 | Lise Binderup | Combination medicament for treatment of neoplastic diseases |
| WO2002094265A1 (en) | 2001-05-24 | 2002-11-28 | Leo Pharma A/S | A method of modulating nf-$g(k)b activity |
| ATE442362T1 (de) | 2001-05-24 | 2009-09-15 | Leo Pharma As | Pyridylcyanoguanidin verbindungen |
| SE0102617D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| US20030127204A1 (en) | 2001-09-06 | 2003-07-10 | Varnell Daniel F. | Amphoteric polymer resins that increase the rate of sizing development |
| BR0212613A (pt) * | 2001-09-19 | 2004-08-31 | Pharmacia Corp | Compostos de indazol substituìdos para o tratamento de inflamação |
| ATE363473T1 (de) | 2001-09-19 | 2007-06-15 | Pharmacia Corp | Substituierte pyrazoloverbindungen zur behandlung von entzündungen |
| WO2003027075A2 (en) | 2001-09-19 | 2003-04-03 | Pharmacia Corporation | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
| EP1444207A2 (en) | 2001-09-19 | 2004-08-11 | Pharmacia Corporation | Substituted pyrazolyl-compounds for the treatment of inflammation |
| JP2005509645A (ja) | 2001-10-30 | 2005-04-14 | ファルマシア・コーポレーション | 炎症処置用のヘテロ芳香族カルボキサミド誘導体 |
| CA2476665A1 (en) | 2002-02-19 | 2003-08-28 | Pharmacia Corporation | Tricyclic pyrazole derivatives for the treatment of inflammation |
| US6933294B2 (en) | 2002-04-03 | 2005-08-23 | Bristol-Myers Squibb Company | Thiophene-based tricyclic compounds and pharmaceutical compositions comprising same |
| MXPA04010952A (es) | 2002-05-09 | 2005-01-25 | Pharmacia Corp | Compuestos de pirazolilo sustituidos para el tratamiento de la inflamacion. |
| DE60325051D1 (de) | 2002-06-06 | 2009-01-15 | Boehringer Ingelheim Pharma | SUBSTITUIERTE 3-AMINO-THIENO(2,3-b)PYRIDINE-2-AMIDE UND HERSTELLUNGSVERFAHREN SOWIE DEREN VERWENDUNG |
| US6900206B2 (en) * | 2002-06-20 | 2005-05-31 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic sulfonylureido piperazine derivatives |
| DE10237722A1 (de) | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| WO2004019935A1 (en) | 2002-08-29 | 2004-03-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | -3 (sulfonamidoethyl) -indole derivaties for use as glucocorticoid mimetics in the treatment of inflammatory, allergic and proliferative diseases |
| SE0202693D0 (sv) * | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| US7135479B2 (en) | 2002-09-12 | 2006-11-14 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of heterocycle-fused benzodioxans |
| US6919334B2 (en) | 2002-09-12 | 2005-07-19 | Wyeth | Antidepressant azaheterocyclymethyl derivatives of 4,5-dihydroimidazo[1,4,5-de][1,4]benzoxazine |
| US6911445B2 (en) | 2002-09-12 | 2005-06-28 | Wyeth | Antidepressant cycloalkylamine derivatives of heterocycle-fused benzodioxans |
| DE10259244A1 (de) | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| WO2004075846A2 (en) | 2003-02-25 | 2004-09-10 | Bristol-Myers Squibb Company | Pyrazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| US7329764B2 (en) | 2003-07-31 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substitute benzothiophene compounds |
| US7291733B2 (en) | 2003-10-10 | 2007-11-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted tricyclic heterocycles and their uses |
| GB0400895D0 (en) * | 2004-01-15 | 2004-02-18 | Smithkline Beecham Corp | Chemical compounds |
| AR050253A1 (es) * | 2004-06-24 | 2006-10-11 | Smithkline Beecham Corp | Compuesto derivado de indazol carboxamida, composicion que lo comprende y su uso para la preparacion de un medicamento |
| AR055343A1 (es) * | 2005-06-30 | 2007-08-22 | Smithkline Beecham Corp | Derivados de indolcarboxamida inhibidores de quinasas ikk2 |
-
2005
- 2005-09-19 PE PE2005001077A patent/PE20060748A1/es not_active Application Discontinuation
- 2005-09-19 TW TW094132222A patent/TW200626142A/zh unknown
- 2005-09-20 AR ARP050103900A patent/AR054084A1/es unknown
- 2005-09-21 WO PCT/US2005/033752 patent/WO2006034317A2/en not_active Ceased
- 2005-09-21 AU AU2005286795A patent/AU2005286795A1/en not_active Abandoned
- 2005-09-21 BR BRPI0515524-0A patent/BRPI0515524A/pt not_active IP Right Cessation
- 2005-09-21 US US11/575,416 patent/US7858796B2/en not_active Expired - Fee Related
- 2005-09-21 EP EP05798511A patent/EP1793826A4/en not_active Withdrawn
- 2005-09-21 JP JP2007532632A patent/JP2008513500A/ja active Pending
- 2005-09-21 KR KR1020077009055A patent/KR20070057969A/ko not_active Withdrawn
- 2005-09-21 MX MX2007003283A patent/MX2007003283A/es unknown
- 2005-09-21 CA CA002581180A patent/CA2581180A1/en not_active Abandoned
- 2005-09-21 SG SG200906215-9A patent/SG155932A1/en unknown
-
2007
- 2007-03-12 IL IL181877A patent/IL181877A0/en unknown
- 2007-03-29 MA MA29785A patent/MA28912B1/fr unknown
- 2007-04-18 NO NO20071988A patent/NO20071988L/no not_active Application Discontinuation