JP2010535165A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010535165A5 JP2010535165A5 JP2010518567A JP2010518567A JP2010535165A5 JP 2010535165 A5 JP2010535165 A5 JP 2010535165A5 JP 2010518567 A JP2010518567 A JP 2010518567A JP 2010518567 A JP2010518567 A JP 2010518567A JP 2010535165 A5 JP2010535165 A5 JP 2010535165A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridyl
- piperidine
- prop
- methyl
- ynylidene
- 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
Links
- -1 cyano, phenyl Chemical group 0.000 claims 275
- 150000001875 compounds Chemical class 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- OMYXXSPBDPYMFE-UHFFFAOYSA-N (2-methoxypyridin-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound COC1=NC=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 OMYXXSPBDPYMFE-UHFFFAOYSA-N 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- MIJHAQQBDWIIQY-UHFFFAOYSA-N 3-nitro-2-[4-[3-(6-propan-2-yloxypyridin-3-yl)prop-2-ynylidene]piperidin-1-yl]pyridine Chemical compound C1=NC(OC(C)C)=CC=C1C#CC=C1CCN(C=2C(=CC=CN=2)[N+]([O-])=O)CC1 MIJHAQQBDWIIQY-UHFFFAOYSA-N 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- VBJVWELAWQTFDN-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound C1CN(C)CCC1OC(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 VBJVWELAWQTFDN-UHFFFAOYSA-N 0.000 claims 1
- JIVSLUNOSXHDDM-UHFFFAOYSA-N (2,3,4-trifluorophenyl) 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC=2C(=C(F)C(F)=CC=2)F)=N1 JIVSLUNOSXHDDM-UHFFFAOYSA-N 0.000 claims 1
- RNDLSDSZAWFVSX-UHFFFAOYSA-N (2,5-dichlorothiophen-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C2=C(SC(Cl)=C2)Cl)=N1 RNDLSDSZAWFVSX-UHFFFAOYSA-N 0.000 claims 1
- DXCWJRFKJZNEFA-UHFFFAOYSA-N (2,5-dimethylfuran-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound O1C(C)=CC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1C DXCWJRFKJZNEFA-UHFFFAOYSA-N 0.000 claims 1
- DQMBFUATWQSSKR-UHFFFAOYSA-N (2,6-dimethoxypyridin-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound COC1=NC(OC)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 DQMBFUATWQSSKR-UHFFFAOYSA-N 0.000 claims 1
- HLYYGPXDHZTFNJ-UHFFFAOYSA-N (2-fluoro-4-nitrophenyl) 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC=2C(=CC(=CC=2)[N+]([O-])=O)F)=N1 HLYYGPXDHZTFNJ-UHFFFAOYSA-N 0.000 claims 1
- JWEDDRDNMGBIDH-UHFFFAOYSA-N (3-ethoxythiophen-2-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound C1=CSC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1OCC JWEDDRDNMGBIDH-UHFFFAOYSA-N 0.000 claims 1
- MHHPFSKBUYYGND-UHFFFAOYSA-N (3-iodophenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(I)C=CC=2)=N1 MHHPFSKBUYYGND-UHFFFAOYSA-N 0.000 claims 1
- WDPLWWIVTYHGQW-UHFFFAOYSA-N (3-methyl-2-nitrophenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C(=C(C)C=CC=2)[N+]([O-])=O)=N1 WDPLWWIVTYHGQW-UHFFFAOYSA-N 0.000 claims 1
- LZRUXBNIOGLOTR-UHFFFAOYSA-N (3-methylfuran-2-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound C1=COC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1C LZRUXBNIOGLOTR-UHFFFAOYSA-N 0.000 claims 1
- GNTARZNMPMOBPT-UHFFFAOYSA-N (3-methylphenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 GNTARZNMPMOBPT-UHFFFAOYSA-N 0.000 claims 1
- DEISQJQWSMFXNS-UHFFFAOYSA-N (4,6-dimethylpyrimidin-2-yl) 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC=2N=C(C)C=C(C)N=2)=N1 DEISQJQWSMFXNS-UHFFFAOYSA-N 0.000 claims 1
- YZZMULHNICLQPX-UHFFFAOYSA-N (4-methoxyphenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 YZZMULHNICLQPX-UHFFFAOYSA-N 0.000 claims 1
- UXOCKEHHODLDQN-UHFFFAOYSA-N (5-bromofuran-2-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2OC(Br)=CC=2)=N1 UXOCKEHHODLDQN-UHFFFAOYSA-N 0.000 claims 1
- YIOFSPHPFCXZIZ-UHFFFAOYSA-N (5-bromopyridin-2-yl) 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC=2N=CC(Br)=CC=2)=N1 YIOFSPHPFCXZIZ-UHFFFAOYSA-N 0.000 claims 1
- ZJHPKKQZJXHVJK-UHFFFAOYSA-N (5-chloro-4-methoxythiophen-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound COC1=C(Cl)SC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 ZJHPKKQZJXHVJK-UHFFFAOYSA-N 0.000 claims 1
- DIKAHMSJXQAWGS-UHFFFAOYSA-N (5-methoxy-1h-indol-3-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound C12=CC(OC)=CC=C2NC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 DIKAHMSJXQAWGS-UHFFFAOYSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- MVDWYBAPNOWZDW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC(C(F)(F)F)C(F)(F)F)=N1 MVDWYBAPNOWZDW-UHFFFAOYSA-N 0.000 claims 1
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- AXTNJZANAMZJIO-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-4-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carbonyl]pyrrolidin-2-one Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C2CC(=O)N(C2)C=2C=C(F)C(C)=CC=2)=N1 AXTNJZANAMZJIO-UHFFFAOYSA-N 0.000 claims 1
- NMJVUEOQYJUQLZ-UHFFFAOYSA-N 1-(3-methyl-5-nitroimidazol-4-yl)-4-(4-phenylbut-3-yn-2-ylidene)piperidine Chemical compound C1CN(C=2N(C=NC=2[N+]([O-])=O)C)CCC1=C(C)C#CC1=CC=CC=C1 NMJVUEOQYJUQLZ-UHFFFAOYSA-N 0.000 claims 1
- AIKLEXWZQOVZKE-UHFFFAOYSA-N 1-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyrrolidin-2-one Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CN1C(=O)CCC1 AIKLEXWZQOVZKE-UHFFFAOYSA-N 0.000 claims 1
- ICAPTLMFNWCLJV-UHFFFAOYSA-N 1-[3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 ICAPTLMFNWCLJV-UHFFFAOYSA-N 0.000 claims 1
- ZJRGHFAQHZFQBU-UHFFFAOYSA-N 1-[3-[3-[1-(6-methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]phenyl]propan-2-one Chemical compound CC(=O)CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=C(C)N=2)[N+]([O-])=O)=C1 ZJRGHFAQHZFQBU-UHFFFAOYSA-N 0.000 claims 1
- CTEWKELQIGCQGY-UHFFFAOYSA-N 1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-2-(2-nitrophenoxy)ethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)COC=2C(=CC=CC=2)[N+]([O-])=O)=N1 CTEWKELQIGCQGY-UHFFFAOYSA-N 0.000 claims 1
- HEWBJUZWTAYGRE-UHFFFAOYSA-N 1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]butan-1-one Chemical compound C1CN(C(=O)CCC)CCC1=CC#CC1=CC=CC(C)=N1 HEWBJUZWTAYGRE-UHFFFAOYSA-N 0.000 claims 1
- SFMRYRUMXONSQK-UHFFFAOYSA-N 1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]heptan-1-one Chemical compound C1CN(C(=O)CCCCCC)CCC1=CC#CC1=CC=CC(C)=N1 SFMRYRUMXONSQK-UHFFFAOYSA-N 0.000 claims 1
- CWYSVUXIKXDFMV-UHFFFAOYSA-N 1-[5-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carbonyl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 CWYSVUXIKXDFMV-UHFFFAOYSA-N 0.000 claims 1
- ILZCDEMKALKKKV-UHFFFAOYSA-N 1-[6-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridin-2-yl]ethanone Chemical compound CC(=O)C1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=N1 ILZCDEMKALKKKV-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- BOTMUFZUGBKPME-UHFFFAOYSA-N 2-(1h-indol-3-yl)ethyl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OCCC=2C3=CC=CC=C3NC=2)=N1 BOTMUFZUGBKPME-UHFFFAOYSA-N 0.000 claims 1
- WSBIRNRPZGNDLH-UHFFFAOYSA-N 2-(2,5-dimethylpyrrol-1-yl)-5-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]pyrimidine Chemical compound CC1=CC=C(C)N1C1=NC=C(N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)C=N1 WSBIRNRPZGNDLH-UHFFFAOYSA-N 0.000 claims 1
- SQBVNJRZVOEUGT-UHFFFAOYSA-N 2-(3-bromophenoxy)-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)COC=2C=C(Br)C=CC=2)=N1 SQBVNJRZVOEUGT-UHFFFAOYSA-N 0.000 claims 1
- HSLNHJUZLXPXEL-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CC=2C=C(Br)C=NC=2)=N1 HSLNHJUZLXPXEL-UHFFFAOYSA-N 0.000 claims 1
- CUOMNTSAIKIJBC-UHFFFAOYSA-N 2-(5-fluoro-1h-indol-3-yl)-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]ethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CC=2C3=CC(F)=CC=C3NC=2)=N1 CUOMNTSAIKIJBC-UHFFFAOYSA-N 0.000 claims 1
- RKKIHUSRIFUDKD-UHFFFAOYSA-N 2-[3-(1-benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC=3C=CC=CC=3)CC2)=N1 RKKIHUSRIFUDKD-UHFFFAOYSA-N 0.000 claims 1
- MMLDPNAFXASCHF-UHFFFAOYSA-N 2-[3-(1-benzylsulfonylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)=N1 MMLDPNAFXASCHF-UHFFFAOYSA-N 0.000 claims 1
- WUXAVLLPTFDMSH-UHFFFAOYSA-N 2-[3-(1-butylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine Chemical compound C1CN(CCCC)CCC1=CC#CC1=CC=CC(C)=N1 WUXAVLLPTFDMSH-UHFFFAOYSA-N 0.000 claims 1
- JDDRVVYNQIPVOX-UHFFFAOYSA-N 2-[3-(1-ethylsulfonylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine Chemical compound C1CN(S(=O)(=O)CC)CCC1=CC#CC1=CC=CC(C)=N1 JDDRVVYNQIPVOX-UHFFFAOYSA-N 0.000 claims 1
- DPPGXPBAKZUIKD-UHFFFAOYSA-N 2-[3-[1-(1,2-dimethylimidazol-4-yl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CN1C(C)=NC(S(=O)(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 DPPGXPBAKZUIKD-UHFFFAOYSA-N 0.000 claims 1
- RYONOLMMZJYWEO-UHFFFAOYSA-N 2-[3-[1-(3-bromophenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)C=2C=C(Br)C=CC=2)=N1 RYONOLMMZJYWEO-UHFFFAOYSA-N 0.000 claims 1
- JHGPSWVAEWXDNT-UHFFFAOYSA-N 2-[3-[1-(4-fluoro-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC(F)=CC=2)[N+]([O-])=O)=N1 JHGPSWVAEWXDNT-UHFFFAOYSA-N 0.000 claims 1
- OBEIVXMEVXXSDB-UHFFFAOYSA-N 2-[3-[1-(4-methoxy-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 OBEIVXMEVXXSDB-UHFFFAOYSA-N 0.000 claims 1
- ZMSMHRWTKJCWBW-UHFFFAOYSA-N 2-[3-[1-(4-methoxyphenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 ZMSMHRWTKJCWBW-UHFFFAOYSA-N 0.000 claims 1
- FVMUFHFHIWKMFG-UHFFFAOYSA-N 2-[3-[1-(5-methoxy-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound COC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 FVMUFHFHIWKMFG-UHFFFAOYSA-N 0.000 claims 1
- FIRJWXKMAOGSDA-UHFFFAOYSA-N 2-[3-[1-(5-tert-butyl-2-methoxyphenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound COC1=CC=C(C(C)(C)C)C=C1S(=O)(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 FIRJWXKMAOGSDA-UHFFFAOYSA-N 0.000 claims 1
- BKTNVFHODQILHH-UHFFFAOYSA-N 2-[3-[1-(cyclohexylmethylsulfonyl)piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)CC2CCCCC2)=N1 BKTNVFHODQILHH-UHFFFAOYSA-N 0.000 claims 1
- AQBFXIHCJBUOHU-UHFFFAOYSA-N 2-[3-[1-[(3-fluorophenyl)methylsulfonyl]piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)CC=2C=C(F)C=CC=2)=N1 AQBFXIHCJBUOHU-UHFFFAOYSA-N 0.000 claims 1
- JARJJPQNEFYJOS-UHFFFAOYSA-N 2-[3-[1-[3-(4-methoxyphenoxy)propylsulfonyl]piperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound C1=CC(OC)=CC=C1OCCCS(=O)(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 JARJJPQNEFYJOS-UHFFFAOYSA-N 0.000 claims 1
- WXWQDKULMVDHOE-UHFFFAOYSA-N 2-[3-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-oxopropyl]isoindole-1,3-dione Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CCN2C(C3=CC=CC=C3C2=O)=O)=N1 WXWQDKULMVDHOE-UHFFFAOYSA-N 0.000 claims 1
- DIVFIAUUIIXJRU-UHFFFAOYSA-N 2-[4-[3-(2,5-difluorophenyl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2C(=CC=C(F)C=2)F)=N1 DIVFIAUUIIXJRU-UHFFFAOYSA-N 0.000 claims 1
- HVXNBXHYCKWDPN-UHFFFAOYSA-N 2-[4-[3-(2,5-difluorophenyl)prop-2-ynylidene]piperidin-1-yl]thiophene-3-carbonitrile Chemical compound FC1=CC=C(F)C(C#CC=C2CCN(CC2)C2=C(C=CS2)C#N)=C1 HVXNBXHYCKWDPN-UHFFFAOYSA-N 0.000 claims 1
- XQINHVIPZNATHQ-UHFFFAOYSA-N 2-[4-[3-(2-fluoropyridin-4-yl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2C=C(F)N=CC=2)=N1 XQINHVIPZNATHQ-UHFFFAOYSA-N 0.000 claims 1
- CGHFISRUKPLSDK-UHFFFAOYSA-N 2-[4-[3-(3,5-difluoro-4-methoxyphenyl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound C1=C(F)C(OC)=C(F)C=C1C#CC=C1CCN(C=2C(=CC=CN=2)[N+]([O-])=O)CC1 CGHFISRUKPLSDK-UHFFFAOYSA-N 0.000 claims 1
- KTHGLJPRAUBPNV-UHFFFAOYSA-N 2-[4-[3-(3,5-difluorophenyl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2C=C(F)C=C(F)C=2)=N1 KTHGLJPRAUBPNV-UHFFFAOYSA-N 0.000 claims 1
- HRZPVGAZESTCHS-UHFFFAOYSA-N 2-[4-[3-(3-bromophenyl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC(Br)=C1 HRZPVGAZESTCHS-UHFFFAOYSA-N 0.000 claims 1
- NTDNSTJWFZRSLJ-UHFFFAOYSA-N 2-[4-[3-(3-chlorophenyl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC(Cl)=C1 NTDNSTJWFZRSLJ-UHFFFAOYSA-N 0.000 claims 1
- KGUIHEYGAPOPIR-UHFFFAOYSA-N 2-[4-[3-(3-ethoxyphenyl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CCOC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=C(C)N=2)[N+]([O-])=O)=C1 KGUIHEYGAPOPIR-UHFFFAOYSA-N 0.000 claims 1
- FQFPMFCSOAUYCD-UHFFFAOYSA-N 2-[4-[3-(3-methoxyphenyl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound COC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 FQFPMFCSOAUYCD-UHFFFAOYSA-N 0.000 claims 1
- ZBOXIAVGEVOBKQ-UHFFFAOYSA-N 2-[4-[3-(3-methylphenyl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 ZBOXIAVGEVOBKQ-UHFFFAOYSA-N 0.000 claims 1
- ROXWUXRKUFTXFC-UHFFFAOYSA-N 2-[4-[3-(4-fluoropyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2N=CC=C(F)C=2)=N1 ROXWUXRKUFTXFC-UHFFFAOYSA-N 0.000 claims 1
- OVADJGQOBQKXOE-UHFFFAOYSA-N 2-[4-[3-(5-cyanopyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC(N2CCC(CC2)=CC#CC=2N=CC(=CC=2)C#N)=C1C#N OVADJGQOBQKXOE-UHFFFAOYSA-N 0.000 claims 1
- YMISOLKZKQMWFN-UHFFFAOYSA-N 2-[4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidin-1-yl]-4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC(N2CCC(CC2)=CC#CC=2C=C(C=NC=2)C#N)=C1C#N YMISOLKZKQMWFN-UHFFFAOYSA-N 0.000 claims 1
- JQRHWZCYWSMSAH-UHFFFAOYSA-N 2-[4-[3-(5-fluoropyridin-3-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CN=CC(F)=C1 JQRHWZCYWSMSAH-UHFFFAOYSA-N 0.000 claims 1
- PKPTXNDKQQPOHJ-UHFFFAOYSA-N 2-[4-[3-(5-fluoropyridin-3-yl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2C=C(F)C=NC=2)=N1 PKPTXNDKQQPOHJ-UHFFFAOYSA-N 0.000 claims 1
- NRLUWENGROJHAR-UHFFFAOYSA-N 2-[4-[3-(6-fluoropyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-6-methyl-3-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2N=C(F)C=CC=2)=N1 NRLUWENGROJHAR-UHFFFAOYSA-N 0.000 claims 1
- JTGIVTUWCAXKMD-UHFFFAOYSA-N 2-[4-[3-(6-fluoropyridin-3-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=C(F)N=C1 JTGIVTUWCAXKMD-UHFFFAOYSA-N 0.000 claims 1
- ITLFYSGIGQYHOP-UHFFFAOYSA-N 2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitroimidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C2=C(N3C=CC=CC3=N2)[N+]([O-])=O)=N1 ITLFYSGIGQYHOP-UHFFFAOYSA-N 0.000 claims 1
- RBJYGZUFTCRCJP-UHFFFAOYSA-N 2-ethoxy-3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CCOC1=NC=CC=C1C#CC=C1CCN(C=2C(=CC=CN=2)[N+]([O-])=O)CC1 RBJYGZUFTCRCJP-UHFFFAOYSA-N 0.000 claims 1
- SFKPHIIQVWZOFR-UHFFFAOYSA-N 2-fluoro-6-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC(F)=N1 SFKPHIIQVWZOFR-UHFFFAOYSA-N 0.000 claims 1
- FZPNCLKLGWVCNB-UHFFFAOYSA-N 2-fluoro-6-methyl-3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound FC1=NC(C)=CC=C1C#CC=C1CCN(C=2C(=CC=CN=2)[N+]([O-])=O)CC1 FZPNCLKLGWVCNB-UHFFFAOYSA-N 0.000 claims 1
- MYBIEXFXZYSVQH-UHFFFAOYSA-N 2-methyl-4-(3-piperidin-4-ylideneprop-1-ynyl)-1,3-thiazole Chemical compound S1C(C)=NC(C#CC=C2CCNCC2)=C1 MYBIEXFXZYSVQH-UHFFFAOYSA-N 0.000 claims 1
- URXPWYSTVVDQGP-UHFFFAOYSA-N 2-methyl-4-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]-1,3-thiazole Chemical compound S1C(C)=NC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 URXPWYSTVVDQGP-UHFFFAOYSA-N 0.000 claims 1
- XAWKEEJDXQLANC-UHFFFAOYSA-N 2-methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine Chemical compound CC1=CC=CC(C#CC=C2CCNCC2)=N1 XAWKEEJDXQLANC-UHFFFAOYSA-N 0.000 claims 1
- XDPFGJXAVSHFAW-UHFFFAOYSA-N 2-methyl-6-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]hex-1-en-4-yn-3-one Chemical compound C1CC(=CC#CC(=O)C(=C)C)CCN1C1=NC=CC=C1[N+]([O-])=O XDPFGJXAVSHFAW-UHFFFAOYSA-N 0.000 claims 1
- PGDZTLDIKMARHN-UHFFFAOYSA-N 2-methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C=CC=CC=2)=N1 PGDZTLDIKMARHN-UHFFFAOYSA-N 0.000 claims 1
- RIGCTUNPQGOMFE-UHFFFAOYSA-N 2-methyl-6-[3-(1-pyridin-2-ylpiperidin-4-ylidene)prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2N=CC=CC=2)=N1 RIGCTUNPQGOMFE-UHFFFAOYSA-N 0.000 claims 1
- ISJGFEZRLIFJLL-UHFFFAOYSA-N 2-methyl-6-[3-[1-(2-methyl-5-nitro-1h-imidazol-4-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound N1C(C)=NC([N+]([O-])=O)=C1N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 ISJGFEZRLIFJLL-UHFFFAOYSA-N 0.000 claims 1
- GTADKUQSONAGQH-UHFFFAOYSA-N 2-methyl-6-[3-[1-(2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 GTADKUQSONAGQH-UHFFFAOYSA-N 0.000 claims 1
- NUGVOIODJYKXMA-UHFFFAOYSA-N 2-methyl-6-[3-[1-(3-methyl-5-nitroimidazol-4-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2N(C=NC=2[N+]([O-])=O)C)=N1 NUGVOIODJYKXMA-UHFFFAOYSA-N 0.000 claims 1
- WYDQDVYUIYFOCH-UHFFFAOYSA-N 2-methyl-6-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=N1 WYDQDVYUIYFOCH-UHFFFAOYSA-N 0.000 claims 1
- CMCAPUCLEBUSFX-UHFFFAOYSA-N 2-methyl-6-[3-[1-(3-nitrothiophen-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C2=C(C=CS2)[N+]([O-])=O)=N1 CMCAPUCLEBUSFX-UHFFFAOYSA-N 0.000 claims 1
- FZKKRTPKKMCTAP-UHFFFAOYSA-N 2-methyl-6-[3-[1-(4-methyl-3-nitrophenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=N1 FZKKRTPKKMCTAP-UHFFFAOYSA-N 0.000 claims 1
- QPZYAQBCKBBTPU-UHFFFAOYSA-N 2-methyl-6-[3-[1-(4-methylpyridin-3-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=NC=2)C)=N1 QPZYAQBCKBBTPU-UHFFFAOYSA-N 0.000 claims 1
- DKWYSUSWAFPVPE-UHFFFAOYSA-N 2-methyl-6-[3-[1-(4-propan-2-ylphenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 DKWYSUSWAFPVPE-UHFFFAOYSA-N 0.000 claims 1
- OJMYCYWSXGQYPW-UHFFFAOYSA-N 2-methyl-6-[3-[1-(5-methyl-2-nitrophenyl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 OJMYCYWSXGQYPW-UHFFFAOYSA-N 0.000 claims 1
- FHOYVKUYOMYYOM-UHFFFAOYSA-N 2-methyl-6-[3-[1-(5-nitro-1h-imidazol-4-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C2=C(N=CN2)[N+]([O-])=O)=N1 FHOYVKUYOMYYOM-UHFFFAOYSA-N 0.000 claims 1
- RZRGCEIUNFCTJH-UHFFFAOYSA-N 2-methyl-6-[3-[1-(5-nitrofuran-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2OC(=CC=2)[N+]([O-])=O)=N1 RZRGCEIUNFCTJH-UHFFFAOYSA-N 0.000 claims 1
- LAHVQCPUQMBWLF-UHFFFAOYSA-N 2-methyl-6-[3-[1-(5-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2N=CC(=CC=2)[N+]([O-])=O)=N1 LAHVQCPUQMBWLF-UHFFFAOYSA-N 0.000 claims 1
- BTICSIFOAGMQLX-UHFFFAOYSA-N 2-methyl-6-[3-[1-[3-(trifluoromethyl)pyridin-2-yl]piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=N1 BTICSIFOAGMQLX-UHFFFAOYSA-N 0.000 claims 1
- VZOPPPGGACWEMH-UHFFFAOYSA-N 2-methyl-6-[3-[1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2N=C(C=CC=2)C(F)(F)F)=N1 VZOPPPGGACWEMH-UHFFFAOYSA-N 0.000 claims 1
- HKQCSOHYRBSTFD-UHFFFAOYSA-N 3,3-dimethyl-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]butan-1-one Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CC(C)(C)C)=N1 HKQCSOHYRBSTFD-UHFFFAOYSA-N 0.000 claims 1
- RRMWIPHPNQKQBE-UHFFFAOYSA-N 3-(3-fluorophenoxy)-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]propan-1-one Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CCOC=2C=C(F)C=CC=2)=N1 RRMWIPHPNQKQBE-UHFFFAOYSA-N 0.000 claims 1
- ZEMJGZVAWWXEGI-UHFFFAOYSA-N 3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC(C#N)=C1 ZEMJGZVAWWXEGI-UHFFFAOYSA-N 0.000 claims 1
- UMMKJCGEDFSTGQ-UHFFFAOYSA-N 3-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]pyrazine-2-carbonitrile Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=NC=CN=2)C#N)=N1 UMMKJCGEDFSTGQ-UHFFFAOYSA-N 0.000 claims 1
- XHCSNEWRSXEHRX-UHFFFAOYSA-N 3-bromo-2-chloro-4-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=NC(Cl)=C1Br XHCSNEWRSXEHRX-UHFFFAOYSA-N 0.000 claims 1
- YAGYDSBUBFDXEX-UHFFFAOYSA-N 3-fluoro-4-methyl-2-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine Chemical compound CC1=CC=NC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1F YAGYDSBUBFDXEX-UHFFFAOYSA-N 0.000 claims 1
- FZAXBPZVVJOFKX-UHFFFAOYSA-N 3-methyl-1,2,4-oxadiazole Chemical compound CC=1N=CON=1 FZAXBPZVVJOFKX-UHFFFAOYSA-N 0.000 claims 1
- LEVRBWQHTUZHGP-UHFFFAOYSA-N 3-methyl-2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-5-nitropyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC(=CN=2)[N+]([O-])=O)C)=N1 LEVRBWQHTUZHGP-UHFFFAOYSA-N 0.000 claims 1
- YATZGLPZEVHKJR-UHFFFAOYSA-N 3-nitro-2-[4-(3-phenylprop-2-ynylidene)piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC=C1 YATZGLPZEVHKJR-UHFFFAOYSA-N 0.000 claims 1
- YFKGKOJKLVSGSA-UHFFFAOYSA-N 3-nitro-2-[4-(3-pyridin-2-ylprop-2-ynylidene)piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CC=N1 YFKGKOJKLVSGSA-UHFFFAOYSA-N 0.000 claims 1
- DKOLFWMCGZPRPC-UHFFFAOYSA-N 3-nitro-2-[4-(3-pyridin-3-ylprop-2-ynylidene)piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=CN=C1 DKOLFWMCGZPRPC-UHFFFAOYSA-N 0.000 claims 1
- UGXUMYCOYXNGCX-UHFFFAOYSA-N 3-nitro-2-[4-(3-pyridin-4-ylprop-2-ynylidene)piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=NC=C1 UGXUMYCOYXNGCX-UHFFFAOYSA-N 0.000 claims 1
- QVPWQOAKUYWDRJ-UHFFFAOYSA-N 3-nitro-2-[4-(4-phenylbut-3-yn-2-ylidene)piperidin-1-yl]pyridine Chemical compound C1CN(C=2C(=CC=CN=2)[N+]([O-])=O)CCC1=C(C)C#CC1=CC=CC=C1 QVPWQOAKUYWDRJ-UHFFFAOYSA-N 0.000 claims 1
- FLSGKVGAMDJYPL-XBXARRHUSA-N 3-nitro-2-[4-[(e)-3-phenylprop-2-enylidene]piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=C\C=C\C1=CC=CC=C1 FLSGKVGAMDJYPL-XBXARRHUSA-N 0.000 claims 1
- LMGASOLCFCTEHQ-UHFFFAOYSA-N 3-nitro-2-[4-[3-(3-nitrophenyl)prop-2-ynylidene]piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 LMGASOLCFCTEHQ-UHFFFAOYSA-N 0.000 claims 1
- LTBHQLDFHLVSLR-UHFFFAOYSA-N 3-nitro-2-[4-[3-[6-(trifluoromethyl)pyridin-3-yl]prop-2-ynylidene]piperidin-1-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=C(C(F)(F)F)N=C1 LTBHQLDFHLVSLR-UHFFFAOYSA-N 0.000 claims 1
- LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 claims 1
- FFHJMLIUFNHAFG-UHFFFAOYSA-N 4,4,4-trifluoro-1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]butan-1-one Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CCC(F)(F)F)=N1 FFHJMLIUFNHAFG-UHFFFAOYSA-N 0.000 claims 1
- QOAKDICTMMJSLE-UHFFFAOYSA-N 4-[3-(3,5-difluorophenyl)prop-2-ynylidene]-1-(3-methyl-5-nitroimidazol-4-yl)piperidine Chemical compound CN1C=NC([N+]([O-])=O)=C1N(CC1)CCC1=CC#CC1=CC(F)=CC(F)=C1 QOAKDICTMMJSLE-UHFFFAOYSA-N 0.000 claims 1
- OKCFWFMZHQESJA-UHFFFAOYSA-N 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]-n-(3-nitrophenyl)piperidine-1-carboxamide Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)NC=2C=C(C=CC=2)[N+]([O-])=O)=N1 OKCFWFMZHQESJA-UHFFFAOYSA-N 0.000 claims 1
- SOAOIVIWLZTDCK-UHFFFAOYSA-N 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]-n-phenylpiperidine-1-carboxamide Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)NC=2C=CC=CC=2)=N1 SOAOIVIWLZTDCK-UHFFFAOYSA-N 0.000 claims 1
- TYXJCSZNKVHNQT-UHFFFAOYSA-N 4-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]isoquinoline Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C3=CC=CC=C3C=NC=2)=N1 TYXJCSZNKVHNQT-UHFFFAOYSA-N 0.000 claims 1
- VNJCGBHVKVRDEZ-UHFFFAOYSA-N 4-[5-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridin-2-yl]morpholine Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=C(N2CCOCC2)N=C1 VNJCGBHVKVRDEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- IIUXCODZVSWOQO-UHFFFAOYSA-N 4-methoxy-3-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]benzonitrile Chemical compound COC1=CC=C(C#N)C=C1N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 IIUXCODZVSWOQO-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- AQYQPGZYZNZCFD-UHFFFAOYSA-N 5-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine-2-carbonitrile Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=C(C#N)N=C1 AQYQPGZYZNZCFD-UHFFFAOYSA-N 0.000 claims 1
- QQQPJXWNAUDUDO-UHFFFAOYSA-N 5-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine-3-carbonitrile Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CN=CC(C#N)=C1 QQQPJXWNAUDUDO-UHFFFAOYSA-N 0.000 claims 1
- XNOQXHMGQKGLSV-UHFFFAOYSA-N 5-[3-[1-(6-methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridine-3-carbonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2C=C(C=NC=2)C#N)=N1 XNOQXHMGQKGLSV-UHFFFAOYSA-N 0.000 claims 1
- HWMMKRBEDIBLJG-UHFFFAOYSA-N 5-bromo-2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]pyrimidine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2N=CC(Br)=CN=2)=N1 HWMMKRBEDIBLJG-UHFFFAOYSA-N 0.000 claims 1
- MVDTZWXRZVSUQW-UHFFFAOYSA-N 5-methyl-2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]cyclopent-2-en-1-one Chemical compound O=C1C(C)CC=C1N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 MVDTZWXRZVSUQW-UHFFFAOYSA-N 0.000 claims 1
- ARBPJODSURMBJE-UHFFFAOYSA-N 6-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]quinoxaline Chemical compound [O-][N+](=O)C1=CC=CN=C1N(CC1)CCC1=CC#CC1=CC=C(N=CC=N2)C2=C1 ARBPJODSURMBJE-UHFFFAOYSA-N 0.000 claims 1
- AQTHFSUSNDFPPG-UHFFFAOYSA-N 6-chloro-5-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]sulfonylimidazo[2,1-b][1,3]thiazole Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)C=2N3C=CSC3=NC=2Cl)=N1 AQTHFSUSNDFPPG-UHFFFAOYSA-N 0.000 claims 1
- NKAMGKJRSCXTMZ-UHFFFAOYSA-N 6-methoxy-2-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound COC1=CC=C([N+]([O-])=O)C(N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=N1 NKAMGKJRSCXTMZ-UHFFFAOYSA-N 0.000 claims 1
- NQDVPJBFJIXQOL-IDUWFGFVSA-N 6-methyl-2-[(3z)-3-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitropyridine Chemical compound CC1=CC=CC(C#C\C=C\2CN(CCC/2)C=2C(=CC=C(C)N=2)[N+]([O-])=O)=N1 NQDVPJBFJIXQOL-IDUWFGFVSA-N 0.000 claims 1
- HUXAEZZYYHMSFH-UHFFFAOYSA-N 6-methyl-2-[4-(4-phenylbut-3-yn-2-ylidene)piperidin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(C=2C(=CC=C(C)N=2)C#N)CCC1=C(C)C#CC1=CC=CC=C1 HUXAEZZYYHMSFH-UHFFFAOYSA-N 0.000 claims 1
- QQCKJNQQJDWNHE-UHFFFAOYSA-N 6-methyl-3-nitro-2-[4-(4-phenylbut-3-yn-2-ylidene)piperidin-1-yl]pyridine Chemical compound C1CN(C=2C(=CC=C(C)N=2)[N+]([O-])=O)CCC1=C(C)C#CC1=CC=CC=C1 QQCKJNQQJDWNHE-UHFFFAOYSA-N 0.000 claims 1
- CBYFZHYCFSQIDX-UHFFFAOYSA-N 7-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]pyrido[2,3-b]pyrazine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C=C3N=CC=NC3=NC=2)=N1 CBYFZHYCFSQIDX-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- BYVWGMDPXMUHMR-UHFFFAOYSA-N [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound O1C(C)=NC(C=2C=C(C=CC=2)C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=N1 BYVWGMDPXMUHMR-UHFFFAOYSA-N 0.000 claims 1
- JXILCLCUWHQEMI-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C2CCN(CC2)C=2C=CN=CC=2)=N1 JXILCLCUWHQEMI-UHFFFAOYSA-N 0.000 claims 1
- DPTMAIFCOKWERF-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(2-nitrophenyl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 DPTMAIFCOKWERF-UHFFFAOYSA-N 0.000 claims 1
- FQAHBEVUAHBENQ-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(2-piperidin-1-ylpyrimidin-5-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=NC(=NC=2)N2CCCCC2)=N1 FQAHBEVUAHBENQ-UHFFFAOYSA-N 0.000 claims 1
- GMSHAPLQYPRIQX-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(3-nitrophenyl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=N1 GMSHAPLQYPRIQX-UHFFFAOYSA-N 0.000 claims 1
- PGVBHUVLBJEMBX-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(3-pyrimidin-2-yloxyphenyl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(OC=3N=CC=CN=3)C=CC=2)=N1 PGVBHUVLBJEMBX-UHFFFAOYSA-N 0.000 claims 1
- OIWATMRSSPKULK-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(4-nitrophenyl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=N1 OIWATMRSSPKULK-UHFFFAOYSA-N 0.000 claims 1
- ASSOHBBUIONVNQ-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-nitrofuran-2-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2OC(=CC=2)[N+]([O-])=O)=N1 ASSOHBBUIONVNQ-UHFFFAOYSA-N 0.000 claims 1
- RPQIEWVJCHXAMH-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-phenylthiophen-2-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2SC(=CC=2)C=2C=CC=CC=2)=N1 RPQIEWVJCHXAMH-UHFFFAOYSA-N 0.000 claims 1
- XGVYHZOHXQQZSG-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-thiophen-2-yl-1h-pyrazol-3-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C2=NNC(=C2)C=2SC=CC=2)=N1 XGVYHZOHXQQZSG-UHFFFAOYSA-N 0.000 claims 1
- JZSGXNZGVFCSRU-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-[3-(1,3-thiazol-2-yl)phenyl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(C=CC=2)C=2SC=CN=2)=N1 JZSGXNZGVFCSRU-UHFFFAOYSA-N 0.000 claims 1
- VNQHLIRSXYQCCG-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-[3-(2-methyl-1,3-thiazol-4-yl)phenyl]methanone Chemical compound S1C(C)=NC(C=2C=C(C=CC=2)C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 VNQHLIRSXYQCCG-UHFFFAOYSA-N 0.000 claims 1
- CUGQIYJEIVMVKC-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-phenylmethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=CC=CC=2)=N1 CUGQIYJEIVMVKC-UHFFFAOYSA-N 0.000 claims 1
- DVPFYKUJMQHPHK-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-quinolin-5-ylmethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C3=CC=CN=C3C=CC=2)=N1 DVPFYKUJMQHPHK-UHFFFAOYSA-N 0.000 claims 1
- GXMCUJJLTGZBHC-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-thiophen-2-ylmethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2SC=CC=2)=N1 GXMCUJJLTGZBHC-UHFFFAOYSA-N 0.000 claims 1
- ULBIABZIBIMVRU-UHFFFAOYSA-N [4-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-3-nitrophenyl]methanol Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC(CO)=CC=2)[N+]([O-])=O)=N1 ULBIABZIBIMVRU-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- WVZLFGZLNHDMTD-UHFFFAOYSA-N benzyl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=N1 WVZLFGZLNHDMTD-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- CCKRLEPMYZYNBO-UHFFFAOYSA-N cyclohexyl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC2CCCCC2)=N1 CCKRLEPMYZYNBO-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- SKIWDLQLZWSHPQ-UHFFFAOYSA-N ethyl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1=CC#CC1=CC=CC(C)=N1 SKIWDLQLZWSHPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- QKWCZSGLFMPQJG-UHFFFAOYSA-N n-butyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCCC)CCC1=CC#CC1=CC=CC(C)=N1 QKWCZSGLFMPQJG-UHFFFAOYSA-N 0.000 claims 1
- ROVCWFANMYKPDP-UHFFFAOYSA-N n-ethyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCC)CCC1=CC#CC1=CC=CC(C)=N1 ROVCWFANMYKPDP-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- DJVCTADGCLXALU-UHFFFAOYSA-N pyridin-2-yl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OC=2N=CC=CC=2)=N1 DJVCTADGCLXALU-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- SLCSCWNEFBCTON-UHFFFAOYSA-N tert-butyl 4-(1-fluoro-3-phenylprop-2-ynylidene)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1=C(F)C#CC1=CC=CC=C1 SLCSCWNEFBCTON-UHFFFAOYSA-N 0.000 claims 1
- IKRVLBVMHXLPCV-UHFFFAOYSA-N tert-butyl 4-[3-(2-methyl-1,3-thiazol-4-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound S1C(C)=NC(C#CC=C2CCN(CC2)C(=O)OC(C)(C)C)=C1 IKRVLBVMHXLPCV-UHFFFAOYSA-N 0.000 claims 1
- ZVEKZOGFOKOTDI-UHFFFAOYSA-N tert-butyl 4-[3-(6-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1=CC#CC1=CC=C(C#N)N=C1 ZVEKZOGFOKOTDI-UHFFFAOYSA-N 0.000 claims 1
- OYMKRMUFADAJSN-UHFFFAOYSA-N tert-butyl 4-hept-2-ynylidenepiperidine-1-carboxylate Chemical compound CCCCC#CC=C1CCN(C(=O)OC(C)(C)C)CC1 OYMKRMUFADAJSN-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- KWFYKIUPCOWWRK-UHFFFAOYSA-N thiophen-2-ylmethyl 4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)OCC=2SC=CC=2)=N1 KWFYKIUPCOWWRK-UHFFFAOYSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95367707P | 2007-08-02 | 2007-08-02 | |
| US60/953,677 | 2007-08-02 | ||
| US4517508P | 2008-04-15 | 2008-04-15 | |
| US61/045,175 | 2008-04-15 | ||
| PCT/EP2008/006351 WO2009015897A1 (en) | 2007-08-02 | 2008-08-01 | Novel heterocyclic compounds as mglu5 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010535165A JP2010535165A (ja) | 2010-11-18 |
| JP2010535165A5 true JP2010535165A5 (https=) | 2012-01-12 |
| JP5412430B2 JP5412430B2 (ja) | 2014-02-12 |
Family
ID=39885225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010518567A Expired - Fee Related JP5412430B2 (ja) | 2007-08-02 | 2008-08-01 | ｍＧｌｕ５拮抗薬としての新規複素環系化合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US8518916B2 (https=) |
| EP (1) | EP2178858B1 (https=) |
| JP (1) | JP5412430B2 (https=) |
| KR (1) | KR20100052507A (https=) |
| CN (1) | CN101821256A (https=) |
| AT (1) | ATE539075T1 (https=) |
| AU (1) | AU2008282032B2 (https=) |
| BR (1) | BRPI0814182A2 (https=) |
| CA (1) | CA2694359A1 (https=) |
| CY (1) | CY1112500T1 (https=) |
| DK (1) | DK2178858T3 (https=) |
| EA (1) | EA018328B1 (https=) |
| ES (1) | ES2380165T3 (https=) |
| HR (1) | HRP20120225T1 (https=) |
| IL (1) | IL203659A (https=) |
| NZ (1) | NZ582934A (https=) |
| PL (1) | PL2178858T3 (https=) |
| PT (1) | PT2178858E (https=) |
| RS (1) | RS52167B (https=) |
| SI (1) | SI2178858T1 (https=) |
| WO (1) | WO2009015897A1 (https=) |
| ZA (1) | ZA201001467B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010089119A1 (en) * | 2009-02-04 | 2010-08-12 | Recordati Ireland Limited | Heterocyclic derivatives as m-glu5 antagonists |
| US20120028931A1 (en) * | 2009-09-14 | 2012-02-02 | Recordati Ireland Limited | Heterocyclic m-glu5 antagonists |
| WO2012085166A1 (en) * | 2010-12-22 | 2012-06-28 | Merz Pharma Gmbh & Co. Kgaa | Metabotropic glutamate receptor modulators |
| AR084515A1 (es) * | 2010-12-22 | 2013-05-22 | Merz Pharma Gmbh & Co Kgaa | Derivados heterociclicos nitrogenados, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de enfermedades asociadas al sistema nervioso central tales como parkinson y alzheimer, entre otras |
| CN104011016B (zh) * | 2011-12-27 | 2016-08-17 | 帝斯曼知识产权资产管理有限公司 | 维生素a中间体的催化合成 |
| CN102827056B (zh) * | 2012-09-03 | 2014-07-23 | 华东理工大学 | N-芳基取代吡咯烷酮衍生物及其用途 |
| WO2014039049A1 (en) * | 2012-09-07 | 2014-03-13 | Empire Technology Development Llc | Regioregular copolymers and methods for making same |
| AU2014211727B2 (en) * | 2013-02-04 | 2018-07-26 | Prexton Therapeutics Sa | Positive allosteric modulators of mGluR3 |
| CA3066193A1 (en) * | 2017-06-29 | 2019-01-03 | Recordati Industria Chimica E Farmaceutica Spa | Heterocyclylmethylidene derivatives and their use as modulators of mglur5 receptors |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE24826E (en) * | 1956-08-30 | 1960-05-17 | N-alkylpiperidyl alkynylamines | |
| JPS5995249A (ja) * | 1982-11-24 | 1984-06-01 | Ono Pharmaceut Co Ltd | ロイコトリエンｂ４類似化合物、その製造方法及びそれらを有効成分として含有する治療剤 |
| EP0537993A1 (en) * | 1991-10-17 | 1993-04-21 | Eli Lilly And Company | Nicotinic activity of a series of arecolones and isoarecolones |
| US5990114A (en) * | 1996-02-28 | 1999-11-23 | Recordati, S.A., Chemical And Pharmaceutical Company | Use of 5-HT1A receptor antagonists for the treatment of urinary incontinence |
| AP2005003199A0 (en) * | 1999-04-01 | 2005-03-31 | Pfizer Prod Inc | Aminopyrimidines as sorbitol dehydrogenase inhibitors |
| US6265434B1 (en) * | 1999-04-06 | 2001-07-24 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| TW593241B (en) | 1999-04-20 | 2004-06-21 | Hoffmann La Roche | Carbamic acid derivatives |
| ITMI991452A1 (it) * | 1999-07-01 | 2001-01-01 | Mediolanum Farmaceutici Srl | Antagonisti selettivi per i recettori m2 con struttura 5h-dibenzo b,fazepinica |
| US6387909B1 (en) * | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
| US6306861B1 (en) * | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
| US6548522B1 (en) | 1999-10-12 | 2003-04-15 | Hoffmann-La Roche Inc. | Method for treating conditions related to the glutamate receptor using carboxylic acid amide derivatives |
| US6403594B1 (en) * | 1999-10-18 | 2002-06-11 | Recordati, S.A. Chemical And Pharmaceutical Company | Benzopyran derivatives |
| US6365591B1 (en) * | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
| EP1230225A2 (en) | 1999-11-01 | 2002-08-14 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| ATE273695T1 (de) | 2000-06-28 | 2004-09-15 | Smithkline Beecham Plc | Nassvermahlung |
| US6369222B1 (en) * | 2000-07-18 | 2002-04-09 | Hoffmann-La Roche Inc. | mGluR antagonists and a method for their synthesis |
| WO2003093236A1 (en) * | 2002-05-02 | 2003-11-13 | Euro-Celtique, S.A. | 1-(pyrid-2-yl)-piperazine compounds as metabotropic glutamate receptor inhibitor |
| US7348337B2 (en) * | 2002-05-28 | 2008-03-25 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides |
| DK1539739T3 (da) * | 2002-08-16 | 2011-03-07 | Janssen Pharmaceutica Nv | Piperidinylforbindelser, der selektivt binder integriner |
| WO2004041777A2 (en) | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Heteroarylpiperidine modulators of chemokine receptor activity |
| US7572922B2 (en) * | 2003-01-27 | 2009-08-11 | Merck & Co., Inc. | Substituted pyrazoles, compositions containing such compounds and methods of use |
| ITMI20030151A1 (it) * | 2003-01-30 | 2004-07-31 | Recordati Ind Chimica E Farma Ceutica S P A | Uso di antagonisti selettivi del recettore mglu5 per il trattamento di disfunzioni neuromuscolari del tratto urinario inferiore. |
| US7338954B2 (en) * | 2003-09-17 | 2008-03-04 | Bristol-Myers Squibb Company | Compounds useful as motilin agonists and method |
| FR2866884B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique |
| WO2005097760A1 (en) | 2004-03-26 | 2005-10-20 | Rigel Pharmaceuticals, Inc. | Heterocyclic anti-viral compounds comprising metabolizable moieties and their uses |
| CA2563123A1 (en) * | 2004-04-02 | 2005-10-20 | Adenosine Therapeutics, Llc | Selective antagonists of a2a adenosine receptors |
| GB0503646D0 (en) * | 2005-02-22 | 2005-03-30 | Novartis Ag | Organic compounds |
| AU2006228957A1 (en) * | 2005-04-01 | 2006-10-05 | Methylgene Inc. | Inhibitors of histone deacetylase |
| GB0514296D0 (en) * | 2005-07-12 | 2005-08-17 | Novartis Ag | Organic compounds |
| US8334290B2 (en) * | 2005-10-31 | 2012-12-18 | Merck Sharp & Dohme Corp. | CETP inhibitors |
| KR101495611B1 (ko) * | 2006-04-07 | 2015-02-25 | 메틸진 인코포레이티드 | 히스톤 데아세틸라아제의 억제제 |
| US7985754B2 (en) | 2006-07-17 | 2011-07-26 | Trovis Pharmaceuticals, Llc | Selective antagonists of A2A adenosine receptors |
-
2008
- 2008-08-01 PT PT08785292T patent/PT2178858E/pt unknown
- 2008-08-01 ES ES08785292T patent/ES2380165T3/es active Active
- 2008-08-01 KR KR1020107004641A patent/KR20100052507A/ko not_active Ceased
- 2008-08-01 EA EA201000283A patent/EA018328B1/ru not_active IP Right Cessation
- 2008-08-01 SI SI200830533T patent/SI2178858T1/sl unknown
- 2008-08-01 DK DK08785292.7T patent/DK2178858T3/da active
- 2008-08-01 JP JP2010518567A patent/JP5412430B2/ja not_active Expired - Fee Related
- 2008-08-01 WO PCT/EP2008/006351 patent/WO2009015897A1/en not_active Ceased
- 2008-08-01 AU AU2008282032A patent/AU2008282032B2/en not_active Expired - Fee Related
- 2008-08-01 NZ NZ582934A patent/NZ582934A/en not_active IP Right Cessation
- 2008-08-01 RS RS20120110A patent/RS52167B/sr unknown
- 2008-08-01 AT AT08785292T patent/ATE539075T1/de active
- 2008-08-01 EP EP08785292A patent/EP2178858B1/en active Active
- 2008-08-01 HR HR20120225T patent/HRP20120225T1/hr unknown
- 2008-08-01 BR BRPI0814182-7A2A patent/BRPI0814182A2/pt not_active IP Right Cessation
- 2008-08-01 CA CA2694359A patent/CA2694359A1/en not_active Abandoned
- 2008-08-01 PL PL08785292T patent/PL2178858T3/pl unknown
- 2008-08-01 CN CN200880101389A patent/CN101821256A/zh active Pending
- 2008-08-04 US US12/185,639 patent/US8518916B2/en not_active Expired - Fee Related
-
2010
- 2010-02-02 IL IL203659A patent/IL203659A/en not_active IP Right Cessation
- 2010-03-01 ZA ZA2010/01467A patent/ZA201001467B/en unknown
-
2012
- 2012-03-21 CY CY20121100296T patent/CY1112500T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010535165A5 (https=) | ||
| HRP20120225T1 (hr) | Novi heterociklični spojevi kao mglu5 antagonisti | |
| JP2006500348A5 (https=) | ||
| RU2396269C2 (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) | |
| CA2418656C (en) | Proline derivatives and use thereof as drugs | |
| JP2019523266A5 (https=) | ||
| CN1764650B (zh) | 2,3,6-三取代的-4-嘧啶酮衍生物 | |
| KR20010083055A (ko) | 글리코겐 신타제 키나제 3의 억제제 | |
| RU2426731C2 (ru) | Производные арил-изоксазоло-4-ил-оксадиазола | |
| JP2007517010A5 (https=) | ||
| HRP20140030T1 (hr) | Derivati prolina kao inhibitori katepsina | |
| AU2004209495A1 (en) | Pyrazole derivative | |
| WO2008065626A3 (en) | 3-heteroaryl (amino or amido)-1- (biphenyl or phenylthiazolyl) carbonylpiperidine derivativesas orexin receptor inhibitors | |
| PE20110063A1 (es) | DERIVADOS DE [1, 2, 4]TRIAZOLO[1, 5-a]PIRIDINA COMO INHIBIDORES DE JAK | |
| JP2015510938A5 (https=) | ||
| JPWO2002014271A1 (ja) | プロリン誘導体及びその医薬用途 | |
| RU2005134006A (ru) | Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера | |
| JP2018530591A5 (https=) | ||
| RU2009105829A (ru) | СОЕДИНЕНИЯ И КОМПОЗИЦИИ В КАЧЕСТВЕ ИНГИБИТОРОВ ITPKb | |
| JP2017512184A5 (https=) | ||
| JP2006528942A5 (https=) | ||
| KR100909953B1 (ko) | 항진균 활성을 갖는 트라이아졸 유도체, 이의 제조방법 및이를 함유하는 약학 조성물 | |
| WO2015078949A1 (en) | Compounds, pharmaceutical composition and methods for use in treating inflammatory diseases | |
| JP2018521119A5 (https=) | ||
| JP2008513405A5 (https=) |