JP2008508307A5 - - Google Patents
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- Publication number
- JP2008508307A5 JP2008508307A5 JP2007523826A JP2007523826A JP2008508307A5 JP 2008508307 A5 JP2008508307 A5 JP 2008508307A5 JP 2007523826 A JP2007523826 A JP 2007523826A JP 2007523826 A JP2007523826 A JP 2007523826A JP 2008508307 A5 JP2008508307 A5 JP 2008508307A5
- Authority
- JP
- Japan
- Prior art keywords
- dipyridin
- ylethyl
- pyridin
- benzonitrile
- phenyl
- 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 (±) -tert-butyl Chemical group 0.000 claims 40
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 14
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 claims 7
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 claims 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- HVJKUXXNDRXBLD-UHFFFAOYSA-N 3-[1-[2-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]-2-pyrazin-2-yl-2-pyridin-3-ylethyl]benzonitrile Chemical compound CC1=NOC(C2N(CCC2)C(C(C=2C=NC=CC=2)C=2N=CC=NC=2)C=2C=C(C=CC=2)C#N)=N1 HVJKUXXNDRXBLD-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- MILIDRSGJZPHTG-UHFFFAOYSA-N (2-benzylpyrazol-3-yl)-dipyridin-3-ylmethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C1=CC=NN1CC1=CC=CC=C1 MILIDRSGJZPHTG-UHFFFAOYSA-N 0.000 claims 1
- VKXYZIUZIYTRFA-GOSISDBHSA-N (2r)-2-cyclopropyl-1,1-dipyridin-3-yl-2-pyrrolidin-1-ylethanol Chemical compound C1([C@H](C(O)(C=2C=NC=CC=2)C=2C=NC=CC=2)N2CCCC2)CC1 VKXYZIUZIYTRFA-GOSISDBHSA-N 0.000 claims 1
- ZIEUODNBWXPPAL-LFQPHHBNSA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n,n-dimethylpyrrolidine-2-carboxamide Chemical compound CN(C)C(=O)[C@@H]1CCCN1C(C=1C=C(C=CC=1)C#N)C(C=1C=NC=CC=1)C1=CC=CN=C1 ZIEUODNBWXPPAL-LFQPHHBNSA-N 0.000 claims 1
- ZVCDPKJNRHTQOG-PVCWFJFTSA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n-(2-methylpropyl)pyrrolidine-2-carboxamide Chemical compound CC(C)CNC(=O)[C@@H]1CCCN1C(C=1C=C(C=CC=1)C#N)C(C=1C=NC=CC=1)C1=CC=CN=C1 ZVCDPKJNRHTQOG-PVCWFJFTSA-N 0.000 claims 1
- LWCFQYWLHHNYDE-PVCWFJFTSA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n-cyclobutylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C(C=1C=NC=CC=1)C=1C=NC=CC=1)C=1C=C(C=CC=1)C#N)NC1CCC1 LWCFQYWLHHNYDE-PVCWFJFTSA-N 0.000 claims 1
- SZYVHOOKOXUBPX-BVOOQYFDSA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n-cyclohexylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C(C=1C=NC=CC=1)C=1C=NC=CC=1)C=1C=C(C=CC=1)C#N)NC1CCCCC1 SZYVHOOKOXUBPX-BVOOQYFDSA-N 0.000 claims 1
- JOBFHXFLUUDQNA-QODXOHEASA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n-cyclopentylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C(C=1C=NC=CC=1)C=1C=NC=CC=1)C=1C=C(C=CC=1)C#N)NC1CCCC1 JOBFHXFLUUDQNA-QODXOHEASA-N 0.000 claims 1
- QYUAVJRNZBSVEW-BVOOQYFDSA-N (2s)-1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-n-phenylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(CCC1)C(C(C=1C=NC=CC=1)C=1C=NC=CC=1)C=1C=C(C=CC=1)C#N)NC1=CC=CC=C1 QYUAVJRNZBSVEW-BVOOQYFDSA-N 0.000 claims 1
- CNBGNWSFQXECRK-BBQAJUCSSA-N (2s)-1-[1-(4-fluorophenyl)-2,2-dipyridin-3-ylethyl]-n-methylpyrrolidine-2-carboxamide Chemical compound CNC(=O)[C@@H]1CCCN1C(C=1C=CC(F)=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 CNBGNWSFQXECRK-BBQAJUCSSA-N 0.000 claims 1
- KOAAIGAWCCSQDQ-BXXZMZEQSA-N (2s)-1-[1-(4-fluorophenyl)-2,2-dipyridin-3-ylethyl]-n-pyridin-2-ylpyrrolidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(N1[C@@H](CCC1)C(=O)NC=1N=CC=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 KOAAIGAWCCSQDQ-BXXZMZEQSA-N 0.000 claims 1
- UMTCRDWWUNFGRQ-MRNPYCGKSA-N (2s)-1-[1-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]piperidin-2-yl]pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1C1N(C(C(C=2C=NC=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C#N)CCCC1 UMTCRDWWUNFGRQ-MRNPYCGKSA-N 0.000 claims 1
- XNWQXPQCJSZQHA-UHFFFAOYSA-N 1,2-diphenyl-2-pyrazol-1-yl-1-pyridin-4-ylethanol Chemical compound C=1C=CC=CC=1C(C=1C=CN=CC=1)(O)C(N1N=CC=C1)C1=CC=CC=C1 XNWQXPQCJSZQHA-UHFFFAOYSA-N 0.000 claims 1
- QWNAKPOJXOHRGZ-UHFFFAOYSA-N 1-(1,2,2-tripyridin-3-ylethyl)pyridin-2-one Chemical compound O=C1C=CC=CN1C(C=1C=NC=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 QWNAKPOJXOHRGZ-UHFFFAOYSA-N 0.000 claims 1
- FFZLONJIESKUIH-UHFFFAOYSA-N 1-(1-pyridin-2-yl-2,2-dipyridin-3-ylethyl)pyridin-2-one Chemical compound O=C1C=CC=CN1C(C=1N=CC=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 FFZLONJIESKUIH-UHFFFAOYSA-N 0.000 claims 1
- PXNYTRQCSJVIIO-UHFFFAOYSA-N 1-(2-hydroxy-1-phenyl-2,2-dipyridin-3-ylethyl)piperidin-3-ol Chemical compound C1C(O)CCCN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=CC=C1 PXNYTRQCSJVIIO-UHFFFAOYSA-N 0.000 claims 1
- CHDFZTHJSACPIJ-UHFFFAOYSA-N 1-(2-hydroxy-2-phenyl-1,2-dipyridin-3-ylethyl)pyridin-2-one Chemical compound C=1C=CC=CC=1C(C=1C=NC=CC=1)(O)C(N1C(C=CC=C1)=O)C1=CC=CN=C1 CHDFZTHJSACPIJ-UHFFFAOYSA-N 0.000 claims 1
- CUUAMACQKULUAB-UHFFFAOYSA-N 1-(2-hydroxy-2-phenyl-2-pyridin-2-yl-1-pyridin-3-ylethyl)pyrazin-2-one Chemical compound C=1C=CC=CC=1C(C=1N=CC=CC=1)(O)C(N1C(C=NC=C1)=O)C1=CC=CN=C1 CUUAMACQKULUAB-UHFFFAOYSA-N 0.000 claims 1
- RHEYZDBPRLDIQQ-UHFFFAOYSA-N 1-(2-hydroxy-2-phenyl-2-pyridin-2-yl-1-pyridin-3-ylethyl)pyridin-2-one Chemical compound C=1C=CC=CC=1C(C=1N=CC=CC=1)(O)C(N1C(C=CC=C1)=O)C1=CC=CN=C1 RHEYZDBPRLDIQQ-UHFFFAOYSA-N 0.000 claims 1
- MLMXLWGMBWYDSF-UHFFFAOYSA-N 1-(2-morpholin-4-ylpyridin-3-yl)-2,2-dipyridin-3-ylethanol Chemical compound C=1C=CN=C(N2CCOCC2)C=1C(O)C(C=1C=NC=CC=1)C1=CC=CN=C1 MLMXLWGMBWYDSF-UHFFFAOYSA-N 0.000 claims 1
- FFZLONJIESKUIH-QFIPXVFZSA-N 1-[(1r)-1-pyridin-2-yl-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound O=C1C=CC=CN1[C@@H](C=1N=CC=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 FFZLONJIESKUIH-QFIPXVFZSA-N 0.000 claims 1
- WKMARJGPHPTLSW-OAQYLSRUSA-N 1-[(1r)-2-hydroxy-1-pyridin-2-yl-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound C1([C@H](C(O)(C=2C=NC=CC=2)C=2C=NC=CC=2)N2C(C=CC=C2)=O)=CC=CC=N1 WKMARJGPHPTLSW-OAQYLSRUSA-N 0.000 claims 1
- FFZLONJIESKUIH-JOCHJYFZSA-N 1-[(1s)-1-pyridin-2-yl-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound O=C1C=CC=CN1[C@H](C=1N=CC=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 FFZLONJIESKUIH-JOCHJYFZSA-N 0.000 claims 1
- WKMARJGPHPTLSW-NRFANRHFSA-N 1-[(1s)-2-hydroxy-1-pyridin-2-yl-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound C1([C@@H](C(O)(C=2C=NC=CC=2)C=2C=NC=CC=2)N2C(C=CC=C2)=O)=CC=CC=N1 WKMARJGPHPTLSW-NRFANRHFSA-N 0.000 claims 1
- QRDMBUYVVONKKF-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2,2-dipyridin-3-ylethyl]-4-methylpiperazine-2,3-dione Chemical compound O=C1C(=O)N(C)CCN1C(C=1C=C(Br)C=CC=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 QRDMBUYVVONKKF-UHFFFAOYSA-N 0.000 claims 1
- FTAXIKCDPRNISM-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2,2-dipyridin-3-ylethyl]pyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C(N1C(CCC1)=O)C(C=1C=NC=CC=1)C1=CC=CN=C1 FTAXIKCDPRNISM-UHFFFAOYSA-N 0.000 claims 1
- KKICULWQUQVVSO-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]-3-methylimidazolidin-2-one Chemical compound O=C1N(C)CCN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=C(F)C=C1 KKICULWQUQVVSO-UHFFFAOYSA-N 0.000 claims 1
- FGAIFLTZSGGIFN-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]azetidin-3-ol Chemical compound C1C(O)CN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=C(F)C=C1 FGAIFLTZSGGIFN-UHFFFAOYSA-N 0.000 claims 1
- WAUPDTKWKGIIFO-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]pyrazin-2-one Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(N1C(C=NC=C1)=O)C1=CC=C(F)C=C1 WAUPDTKWKGIIFO-UHFFFAOYSA-N 0.000 claims 1
- CXPCUZTVWFJTAI-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(N1C(C=CC=C1)=O)C1=CC=C(F)C=C1 CXPCUZTVWFJTAI-UHFFFAOYSA-N 0.000 claims 1
- VSDOWOBMEWOLSS-UHFFFAOYSA-N 1-[1-(6-chloropyridin-2-yl)-2,2-dipyridin-3-ylethyl]pyridin-2-one Chemical compound ClC1=CC=CC(C(C(C=2C=NC=CC=2)C=2C=NC=CC=2)N2C(C=CC=C2)=O)=N1 VSDOWOBMEWOLSS-UHFFFAOYSA-N 0.000 claims 1
- RJYJLRCNUSBSSY-UHFFFAOYSA-N 1-[2-[methyl(pyridin-3-yl)amino]pyridin-3-yl]-2,2-dipyridin-3-ylethanol Chemical compound N=1C=CC=C(C(O)C(C=2C=NC=CC=2)C=2C=NC=CC=2)C=1N(C)C1=CC=CN=C1 RJYJLRCNUSBSSY-UHFFFAOYSA-N 0.000 claims 1
- QQUDKVBLDFBNBU-UHFFFAOYSA-N 1-phenyl-1-pyridin-2-yl-2-pyridin-3-yl-2-(triazol-1-yl)ethanol Chemical compound C=1C=CC=CC=1C(C=1N=CC=CC=1)(O)C(N1N=NC=C1)C1=CC=CN=C1 QQUDKVBLDFBNBU-UHFFFAOYSA-N 0.000 claims 1
- XLDPJFGICUUUTC-UHFFFAOYSA-N 1-tert-butyl-3-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]imidazolidin-2-one Chemical compound O=C1N(C(C)(C)C)CCN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=C(F)C=C1 XLDPJFGICUUUTC-UHFFFAOYSA-N 0.000 claims 1
- FZGKIQFEPNXHCF-UHFFFAOYSA-N 2,2-dimethylpropyl n-[1-(4-chlorophenyl)-2,2-dipyridin-3-ylethyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1C(NC(=O)OCC(C)(C)C)C(C=1C=NC=CC=1)C1=CC=CN=C1 FZGKIQFEPNXHCF-UHFFFAOYSA-N 0.000 claims 1
- PMUBZRKLMQDDMO-UHFFFAOYSA-N 2,2-dipyridin-3-yl-1-(2-pyridin-3-ylpyridin-3-yl)ethanamine Chemical compound C=1C=CN=C(C=2C=NC=CC=2)C=1C(N)C(C=1C=NC=CC=1)C1=CC=CN=C1 PMUBZRKLMQDDMO-UHFFFAOYSA-N 0.000 claims 1
- GHXYRZWZQQDKIT-UHFFFAOYSA-N 2-(1,4-oxazepan-4-yl)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC=CC=1)N1CCCOCC1 GHXYRZWZQQDKIT-UHFFFAOYSA-N 0.000 claims 1
- SQRKYAPXRKAZAP-UHFFFAOYSA-N 2-(3,3-difluoropyrrolidin-1-yl)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC=CC=1)N1CCC(F)(F)C1 SQRKYAPXRKAZAP-UHFFFAOYSA-N 0.000 claims 1
- TZDWWFMVGXYPON-UHFFFAOYSA-N 2-(3-bromophenyl)-1,1-dipyridin-3-yl-2-pyrrolidin-1-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=C(Br)C=CC=1)N1CCCC1 TZDWWFMVGXYPON-UHFFFAOYSA-N 0.000 claims 1
- BGQWIGOIJUZPHD-UHFFFAOYSA-N 2-(3-fluoropyrrolidin-1-yl)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC=CC=1)N1CCC(F)C1 BGQWIGOIJUZPHD-UHFFFAOYSA-N 0.000 claims 1
- LGKKPLBOBOVCJW-UHFFFAOYSA-N 2-(3-methoxyphenyl)-1,1-dipyridin-3-yl-2-pyrrolidin-1-ylethanol Chemical compound COC1=CC=CC(C(N2CCCC2)C(O)(C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 LGKKPLBOBOVCJW-UHFFFAOYSA-N 0.000 claims 1
- SFBOFDWTMJUNDZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,1-dipyridin-3-yl-2-pyrrolidin-1-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC(F)=CC=1)N1CCCC1 SFBOFDWTMJUNDZ-UHFFFAOYSA-N 0.000 claims 1
- OPBQJUSVRIXWGD-HMTLIYDFSA-N 2-(4-fluorophenyl)-2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-1,1-dipyridin-3-ylethanol Chemical compound OC[C@@H]1CCCN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=C(F)C=C1 OPBQJUSVRIXWGD-HMTLIYDFSA-N 0.000 claims 1
- BAZZAFVBINNLRK-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)-1,1-dipyridin-3-yl-2-pyrrolidin-1-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1SC(Cl)=CC=1)N1CCCC1 BAZZAFVBINNLRK-UHFFFAOYSA-N 0.000 claims 1
- GORDETLYLYBIJN-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-1,1-dipyridin-3-yl-2-(triazol-1-yl)ethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(N1N=NC=C1)C1=CC=C(Br)N=C1 GORDETLYLYBIJN-UHFFFAOYSA-N 0.000 claims 1
- XQDOMXYPBFADSZ-UHFFFAOYSA-N 2-(7-azabicyclo[2.2.1]heptan-7-yl)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(N1C2CCC1CC2)C1=CC=CC=C1 XQDOMXYPBFADSZ-UHFFFAOYSA-N 0.000 claims 1
- RYSJSCZDZPPNGL-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(S(=O)(=O)C=1C=CC=CC=1)C1=CC=CC=C1 RYSJSCZDZPPNGL-UHFFFAOYSA-N 0.000 claims 1
- BPOGZQLRJMYGIF-UHFFFAOYSA-N 2-(cyclobutylamino)-2-(4-fluorophenyl)-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC(F)=CC=1)NC1CCC1 BPOGZQLRJMYGIF-UHFFFAOYSA-N 0.000 claims 1
- JJWNFTHIOIOXBG-UHFFFAOYSA-N 2-(diethylamino)-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(O)(C=1C=NC=CC=1)C(N(CC)CC)C1=CC=CC=C1 JJWNFTHIOIOXBG-UHFFFAOYSA-N 0.000 claims 1
- TZEQVLKBRXSJKC-LGTSYYJHSA-N 2-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=CC=C1 TZEQVLKBRXSJKC-LGTSYYJHSA-N 0.000 claims 1
- VDDKEVZGASKOII-WTQRLHSKSA-N 2-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound COC[C@H]1CCCN1C(C(O)(C=1C=NC=CC=1)C=1C=NC=CC=1)C1=CC=CC=C1 VDDKEVZGASKOII-WTQRLHSKSA-N 0.000 claims 1
- HDMPQGUZWUHWDW-OSBQEZSISA-N 2-[(3r,4r)-3,4-difluoropyrrolidin-1-yl]-2-phenyl-1,1-dipyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(C=1C=CC=CC=1)N1C[C@@H](F)[C@H](F)C1 HDMPQGUZWUHWDW-OSBQEZSISA-N 0.000 claims 1
- HLHAYHIFUWNJFM-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-hydroxy-2,2-dipyridin-3-ylethyl]pyridazin-3-one Chemical compound C=1C=CN=CC=1C(C=1C=NC=CC=1)(O)C(N1C(C=CC=N1)=O)C1=CC=C(F)C=C1 HLHAYHIFUWNJFM-UHFFFAOYSA-N 0.000 claims 1
- HHMYTUJQQLDICS-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-imidazol-1-yl-2-pyridin-3-ylethyl]pyridine Chemical compound C1=CC(F)=CC=C1C(C=1N=CC=CC=1)C(N1C=NC=C1)C1=CC=CN=C1 HHMYTUJQQLDICS-UHFFFAOYSA-N 0.000 claims 1
- CATIVELODMFSTJ-UHFFFAOYSA-N 2-[1-[1-(4-fluorophenyl)-2,2-dipyridin-3-ylethyl]pyrrolidin-2-yl]-1h-benzimidazole Chemical compound C1=CC(F)=CC=C1C(N1C(CCC1)C=1NC2=CC=CC=C2N=1)C(C=1C=NC=CC=1)C1=CC=CN=C1 CATIVELODMFSTJ-UHFFFAOYSA-N 0.000 claims 1
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| AU2006306542B2 (en) * | 2005-10-21 | 2012-04-19 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| US8080543B2 (en) | 2006-02-01 | 2011-12-20 | Merck Sharp & Dohme | Pyridine derivative potassium channel inhibitors |
| AU2007209981B2 (en) * | 2006-02-01 | 2011-11-24 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| AU2007209903B2 (en) * | 2006-02-01 | 2012-09-13 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| AU2009290474A1 (en) | 2008-09-11 | 2010-03-18 | Pfizer Inc. | Heteroaryls amide derivatives and their use as glucokinase activators |
| EP2389374A1 (en) | 2009-01-20 | 2011-11-30 | Pfizer Inc. | Substituted pyrazinone amides |
| EP2604604A1 (en) | 2009-03-11 | 2013-06-19 | Pfizer Inc | Benzofuranyl derivatives used as glucokinase inhibitors |
| CN103328452A (zh) * | 2010-12-13 | 2013-09-25 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
| FR2969606B1 (fr) * | 2010-12-22 | 2013-01-11 | Pf Medicament | Derives de diarylpyridazinones, leur preparation et leur application en therapeutique humaine |
| NZ631258A (en) | 2012-04-25 | 2016-11-25 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| WO2014010732A1 (ja) | 2012-07-13 | 2014-01-16 | 武田薬品工業株式会社 | 複素環化合物 |
| CN104781256B (zh) | 2012-10-29 | 2017-09-29 | 霍夫曼-拉罗奇有限公司 | 3，4‑双取代的噁唑烷酮衍生物和其作为钙激活的钾通道的抑制剂的用途 |
| US9573961B2 (en) | 2012-12-19 | 2017-02-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9604998B2 (en) | 2013-02-18 | 2017-03-28 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2975031A4 (en) | 2013-03-14 | 2017-04-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| WO2014150132A1 (en) | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| CN105121411B (zh) | 2013-04-15 | 2017-10-10 | 杜邦公司 | 杀真菌酰胺 |
| EP3018123B1 (en) | 2013-07-03 | 2023-05-10 | Takeda Pharmaceutical Company Limited | Amide compound |
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| WO2015017305A1 (en) | 2013-07-31 | 2015-02-05 | Merck Sharp & Dohme Corp | Inhibitors of the renal outer medullary potassium channel |
| SI3050878T1 (sl) | 2013-09-24 | 2022-01-31 | Fujifilm Corporation | Nova dušik-vsebujoča spojina ali njena sol ali kovinski kompleks le-te |
| US20160264536A1 (en) | 2013-10-23 | 2016-09-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP3063142B1 (en) | 2013-10-31 | 2019-01-30 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016127358A1 (en) | 2015-02-12 | 2016-08-18 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| CN104926716A (zh) * | 2015-06-10 | 2015-09-23 | 哈尔滨工业大学 | 吡啶衍生物2,6-二[(6-甲氧基吡啶-2-基)甲基]吡啶及其合成方法 |
| CN104844503A (zh) * | 2015-06-10 | 2015-08-19 | 哈尔滨工业大学 | 吡啶衍生物6-[(6-甲氧基吡啶-2-基)甲基]-2,2’-吡啶及其合成方法 |
| US11166940B2 (en) * | 2016-12-22 | 2021-11-09 | Ramot At Tel-Aviv University Ltd. | Treatment of cardiac disorders by blocking SK4 potassium channel |
| JP2021523092A (ja) * | 2018-03-21 | 2021-09-02 | ピラマル・ファーマ・リミテッドＰｉｒａｍａｌ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ | アルファ−（ジアリールメチル）アルキルアミンの改良された不斉合成 |
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| GB765853A (en) * | 1952-04-03 | 1957-01-16 | Abbott Lab | Improvements in or relating to substituted piperidines |
| GB915804A (en) * | 1958-04-12 | 1963-01-16 | Degussa | Process for the production of basically substituted carboxylic acid amides |
| EP0435127A3 (en) * | 1989-12-29 | 1991-12-27 | Basf Aktiengesellschaft | 3-substituted pyridines |
| US6632836B1 (en) | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| AU2002212969B2 (en) | 2000-09-20 | 2006-07-06 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| JP4394451B2 (ja) * | 2002-01-04 | 2010-01-06 | ニューロサーチ、アクティーゼルスカブ | カリウムチャネルモジュレーター |
| WO2005030729A1 (en) | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinoline potassium channel inhibitors |
| CA2539760C (en) | 2003-09-23 | 2011-01-25 | Merck & Co., Inc. | Quinoline potassium channel inhibitors |
| WO2005030130A2 (en) | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinoline potassium channel inhibitors |
| US7723352B2 (en) | 2003-09-23 | 2010-05-25 | Merck Sharp & Dohme | Isoquinolinone potassium channel inhibitors |
| JP4719681B2 (ja) | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | キナゾリンカリウムチャネル阻害剤 |
| CN1856307A (zh) | 2003-09-23 | 2006-11-01 | 默克公司 | 喹啉钾通道抑制剂 |
| EP1667976B1 (en) | 2003-09-23 | 2010-08-04 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| JP4719152B2 (ja) | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | イソキノリノンカリウムチャネル阻害剤 |
| DE102005028845A1 (de) * | 2005-06-22 | 2006-12-28 | Sanofi-Aventis Deutschland Gmbh | Substituierte Heterocyclen, ihre Verwendung als Medikament sowie enthaltende pharmazeutische Zubereitungen |
-
2005
- 2005-07-27 CN CNA2005800255476A patent/CN1993347A/zh active Pending
- 2005-07-27 WO PCT/US2005/026868 patent/WO2006015159A2/en not_active Ceased
- 2005-07-27 JP JP2007523826A patent/JP4719745B2/ja not_active Expired - Fee Related
- 2005-07-27 US US11/658,114 patent/US7879839B2/en active Active
- 2005-07-27 AU AU2005267884A patent/AU2005267884B2/en not_active Ceased
- 2005-07-27 EP EP05776464A patent/EP1781635B1/en not_active Expired - Lifetime
- 2005-07-27 CA CA2575003A patent/CA2575003C/en not_active Expired - Fee Related
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