JP2005514365A5 - - Google Patents
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- JP2005514365A5 JP2005514365A5 JP2003545651A JP2003545651A JP2005514365A5 JP 2005514365 A5 JP2005514365 A5 JP 2005514365A5 JP 2003545651 A JP2003545651 A JP 2003545651A JP 2003545651 A JP2003545651 A JP 2003545651A JP 2005514365 A5 JP2005514365 A5 JP 2005514365A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- indole
- carboxylic acid
- ylmethyl
- amide
- 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.)
- Granted
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- -1 phenylpyridyl groups Chemical group 0.000 claims description 103
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000002950 monocyclic group Chemical group 0.000 claims description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- 150000001408 amides Chemical class 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002619 bicyclic group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052760 oxygen Chemical group 0.000 claims description 21
- 239000001301 oxygen Chemical group 0.000 claims description 21
- 239000011593 sulfur Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- RJCRRLMFYIXJAH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RJCRRLMFYIXJAH-UHFFFAOYSA-N 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 150000003536 tetrazoles Chemical class 0.000 claims description 10
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 7
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 7
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 7
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 7
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 7
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 7
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 7
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims description 6
- AXJHGZQKOZQHQC-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1 AXJHGZQKOZQHQC-UHFFFAOYSA-N 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- XMBHXMWOQCBVDD-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]-5-nitro-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC([N+]([O-])=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1 XMBHXMWOQCBVDD-UHFFFAOYSA-N 0.000 claims description 3
- ALRWWJBPMNKBTQ-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-2-oxoethyl]-n-(1-cyclopropylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)NC1CCN(C2CC2)CC1 ALRWWJBPMNKBTQ-UHFFFAOYSA-N 0.000 claims description 3
- ILRJJEMRKWAJMZ-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ILRJJEMRKWAJMZ-UHFFFAOYSA-N 0.000 claims description 3
- LBQLDTXJHMXFGR-UHFFFAOYSA-N 1-[2-[(5-chlorothiophen-2-yl)amino]-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)S1 LBQLDTXJHMXFGR-UHFFFAOYSA-N 0.000 claims description 3
- DQJGJGNWFRPEHZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DQJGJGNWFRPEHZ-UHFFFAOYSA-N 0.000 claims description 3
- XDHLEMSKBSBEDC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-cyclopropylpiperidin-4-yl)indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C2CC2)=NO1 XDHLEMSKBSBEDC-UHFFFAOYSA-N 0.000 claims description 3
- ZIJGLYMYEJVXBJ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-ethylpiperidin-4-yl)-7-methylindole-2-carboxamide Chemical compound C1CN(CC)CCC1NC(=O)C1=CC2=CC=CC(C)=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZIJGLYMYEJVXBJ-UHFFFAOYSA-N 0.000 claims description 3
- QSORXIOYPRDNJX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-formylpiperidin-4-yl)indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C=O)=NO1 QSORXIOYPRDNJX-UHFFFAOYSA-N 0.000 claims description 3
- GZYLKYFEFKEDRG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-methylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GZYLKYFEFKEDRG-UHFFFAOYSA-N 0.000 claims description 3
- GJUUXHXBHXTVKN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-methylpiperazin-1-yl)indole-2-carboxamide Chemical compound C1CN(C)CCN1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GJUUXHXBHXTVKN-UHFFFAOYSA-N 0.000 claims description 3
- OYIDOIKTXHNHIG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[(1-propan-2-ylpiperidin-4-yl)methyl]indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1CNC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OYIDOIKTXHNHIG-UHFFFAOYSA-N 0.000 claims description 3
- DHCMYQUCCIZFNC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[(3-pyridin-4-yl-4,5-dihydro-1,2-oxazol-5-yl)methyl]indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NCC2ON=C(C2)C=2C=CN=CC=2)=NO1 DHCMYQUCCIZFNC-UHFFFAOYSA-N 0.000 claims description 3
- LXDJGDUZQJAKNT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]indole-2-carboxamide Chemical compound C1CN(CC(F)(F)F)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LXDJGDUZQJAKNT-UHFFFAOYSA-N 0.000 claims description 3
- SVPMYJVMCNPHDZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[1-(oxan-4-yl)piperidin-4-yl]indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C2CCOCC2)=NO1 SVPMYJVMCNPHDZ-UHFFFAOYSA-N 0.000 claims description 3
- UQTLOYNEJNQFNC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC2=CC(C(O)=O)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 UQTLOYNEJNQFNC-UHFFFAOYSA-N 0.000 claims description 3
- BDLMBQRBNPDCSS-UHFFFAOYSA-N 1-{2-[(4-chlorophenyl)amino]-2-oxoethyl}-n-(1-isopropylpiperidin-4-yl)-1h-indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1 BDLMBQRBNPDCSS-UHFFFAOYSA-N 0.000 claims description 3
- VZGXXNKOVRJPAJ-UHFFFAOYSA-N 4-chloro-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=C(Cl)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 VZGXXNKOVRJPAJ-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- MGRCNGCGYRBCHN-UHFFFAOYSA-N [1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indol-2-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)N2CCC(CC2)N2CCCC2)=NO1 MGRCNGCGYRBCHN-UHFFFAOYSA-N 0.000 claims description 3
- RIWBBCOZKYZGPE-UHFFFAOYSA-N [1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indol-2-yl]-[4-(pyridin-4-ylmethyl)piperazin-1-yl]methanone Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)N2CCN(CC=3C=CN=CC=3)CC2)=NO1 RIWBBCOZKYZGPE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- AZKKPVUCXDZBCR-UHFFFAOYSA-N ethyl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-7-methylindole-2-carbonyl]-(1-propan-2-ylpiperidin-4-yl)amino]acetate Chemical compound C=1C2=CC=CC(C)=C2N(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C=1C(=O)N(CC(=O)OCC)C1CCN(C(C)C)CC1 AZKKPVUCXDZBCR-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- WHVRIEBTPHOXEE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-(4-pyrrolidin-1-ylpiperidine-1-carbonyl)indol-1-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)N1CCC(N2CCCC2)CC1 WHVRIEBTPHOXEE-UHFFFAOYSA-N 0.000 claims description 3
- MIJCTFQIMWKOJZ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-[4-(pyridin-4-ylamino)piperidine-1-carbonyl]indol-1-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)N1CCC(NC=2C=CN=CC=2)CC1 MIJCTFQIMWKOJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002829 nitrogen Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- TUJRINRCZRSTKI-UHFFFAOYSA-N 1-[2-(4-chloro-2-fluoroanilino)-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=C1F TUJRINRCZRSTKI-UHFFFAOYSA-N 0.000 claims description 2
- QKTOKVVJQUZKKE-UHFFFAOYSA-N 5,7-dichloro-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Cl)=CC(Cl)=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 QKTOKVVJQUZKKE-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims 8
- ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
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-
2001
- 2001-11-22 EP EP01127809A patent/EP1314733A1/en not_active Withdrawn
-
2002
- 2002-08-11 UA UA20040604882A patent/UA78731C2/uk unknown
- 2002-11-08 KR KR1020107003845A patent/KR101033798B1/ko not_active Expired - Fee Related
- 2002-11-08 RS YUP-404/04A patent/RS40404A/sr unknown
- 2002-11-08 CN CNB028232488A patent/CN1283638C/zh not_active Expired - Fee Related
- 2002-11-08 HR HR20040453A patent/HRP20040453A2/xx not_active Application Discontinuation
- 2002-11-08 CA CA2467374A patent/CA2467374C/en not_active Expired - Fee Related
- 2002-11-08 WO PCT/EP2002/012500 patent/WO2003044014A1/en not_active Ceased
- 2002-11-08 HU HU0402063A patent/HUP0402063A3/hu unknown
- 2002-11-08 ME MEP-430/08A patent/MEP43008A/xx unknown
- 2002-11-08 OA OA1200400142A patent/OA12727A/en unknown
- 2002-11-08 KR KR1020047007838A patent/KR100954508B1/ko not_active Expired - Fee Related
- 2002-11-08 AU AU2002351918A patent/AU2002351918B2/en not_active Ceased
- 2002-11-08 RU RU2004118710/04A patent/RU2299881C2/ru not_active IP Right Cessation
- 2002-11-08 PL PL368949A patent/PL210986B1/pl unknown
- 2002-11-08 EP EP02787604.4A patent/EP1451185B1/en not_active Expired - Lifetime
- 2002-11-08 IL IL16210502A patent/IL162105A0/xx unknown
- 2002-11-08 MX MXPA04004797A patent/MXPA04004797A/es active IP Right Grant
- 2002-11-08 JP JP2003545651A patent/JP4664592B2/ja not_active Expired - Fee Related
- 2002-11-08 BR BR0214396-8A patent/BR0214396A/pt active Search and Examination
- 2002-11-08 NZ NZ533044A patent/NZ533044A/en not_active IP Right Cessation
- 2002-11-19 PE PE2002001105A patent/PE20030593A1/es not_active Application Discontinuation
- 2002-11-20 AR ARP020104452A patent/AR037656A1/es active IP Right Grant
- 2002-11-20 TW TW091133782A patent/TWI291950B/zh not_active IP Right Cessation
- 2002-11-21 US US10/301,397 patent/US6906084B2/en not_active Expired - Lifetime
- 2002-11-22 MY MYPI20024375A patent/MY131516A/en unknown
-
2004
- 2004-04-19 ZA ZA2004/02945A patent/ZA200402945B/en unknown
- 2004-04-22 MA MA27647A patent/MA27350A1/fr unknown
- 2004-05-20 EC EC2004005115A patent/ECSP045115A/es unknown
- 2004-05-20 IL IL162105A patent/IL162105A/en not_active IP Right Cessation
- 2004-05-20 CO CO04046947A patent/CO5580764A2/es active IP Right Grant
- 2004-05-21 TN TNP2004000091A patent/TNSN04091A1/en unknown
- 2004-06-21 NO NO20042592A patent/NO327466B1/no not_active IP Right Cessation
- 2004-08-26 US US10/926,909 patent/US20050043302A1/en not_active Abandoned
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2008
- 2008-05-12 US US12/119,013 patent/US20090069565A1/en not_active Abandoned
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