HRP20120225T1 - Novi heterociklični spojevi kao mglu5 antagonisti - Google Patents
Novi heterociklični spojevi kao mglu5 antagonisti Download PDFInfo
- Publication number
- HRP20120225T1 HRP20120225T1 HR20120225T HRP20120225T HRP20120225T1 HR P20120225 T1 HRP20120225 T1 HR P20120225T1 HR 20120225 T HR20120225 T HR 20120225T HR P20120225 T HRP20120225 T HR P20120225T HR P20120225 T1 HRP20120225 T1 HR P20120225T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridyl
- piperidine
- prop
- ynylidene
- methyl
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract 2
- 239000005557 antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- -1 C1-C6alkyl Chemical group 0.000 claims 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052731 fluorine Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000005466 alkylenyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 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
- ZPEVOJQFBXKZRB-UHFFFAOYSA-N (1-methylbenzotriazol-5-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=2C=C3N=NN(C)C3=CC=2)=N1 ZPEVOJQFBXKZRB-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
- OYBWNZHHFZBUQW-UHFFFAOYSA-N (2-chloro-6-methoxypyridin-4-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound ClC1=NC(OC)=CC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 OYBWNZHHFZBUQW-UHFFFAOYSA-N 0.000 claims 1
- ZSGOSJRTWAOZNV-UHFFFAOYSA-N (2-chloro-6-methylpyridin-4-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=2C=C(Cl)N=C(C)C=2)=N1 ZSGOSJRTWAOZNV-UHFFFAOYSA-N 0.000 claims 1
- CPCBQVROYOGMHU-UHFFFAOYSA-N (2-methoxyphenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 CPCBQVROYOGMHU-UHFFFAOYSA-N 0.000 claims 1
- UQGHKOIGZYELRM-UHFFFAOYSA-N (3-bromophenyl)-[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(Br)C=CC=2)=N1 UQGHKOIGZYELRM-UHFFFAOYSA-N 0.000 claims 1
- XOGNAHSODCBNIF-UHFFFAOYSA-N (3-chloro-4-methylthiophen-2-yl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound CC1=CSC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1Cl XOGNAHSODCBNIF-UHFFFAOYSA-N 0.000 claims 1
- PGBLXONVLMXXEL-UHFFFAOYSA-N (3-chlorophenyl)-[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(Cl)C=CC=2)=N1 PGBLXONVLMXXEL-UHFFFAOYSA-N 0.000 claims 1
- MDPMQATZMWHZOW-UHFFFAOYSA-N (3-chlorothiophen-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)C2=C(C=CS2)Cl)=N1 MDPMQATZMWHZOW-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
- MDIBBZYMQUDVAP-UHFFFAOYSA-N (3-fluorophenyl)-[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(F)C=CC=2)=N1 MDIBBZYMQUDVAP-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
- RKYZXRFHJBMXQG-UHFFFAOYSA-N (3-methoxyphenyl)-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 RKYZXRFHJBMXQG-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
- 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
- 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
- YADWZUXTFVSUHB-UHFFFAOYSA-N (5-chlorothiophen-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=2SC(Cl)=CC=2)=N1 YADWZUXTFVSUHB-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
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 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
- IUWWNWGTFOYBMU-UHFFFAOYSA-N 1-[3-[3-[1-(6-methyl-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=C(C)N=2)[N+]([O-])=O)=C1 IUWWNWGTFOYBMU-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
- QDVDEVISNSQSMF-UHFFFAOYSA-N 1-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-4-phenylbutan-1-one Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)CCCC=2C=CC=CC=2)=N1 QDVDEVISNSQSMF-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
- SBZZNULIMIMELH-UHFFFAOYSA-N 1-methyl-4-[[3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=CN=2)[N+]([O-])=O)=C1 SBZZNULIMIMELH-UHFFFAOYSA-N 0.000 claims 1
- YAERAZRWLRLWSA-UHFFFAOYSA-N 2,2-dimethyl-n-[3-[3-[1-(3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]pyridin-2-yl]propanamide Chemical compound CC(C)(C)C(=O)NC1=NC=CC=C1C#CC=C1CCN(C=2C(=CC=CN=2)[N+]([O-])=O)CC1 YAERAZRWLRLWSA-UHFFFAOYSA-N 0.000 claims 1
- RWXNALYEOBQGBB-UHFFFAOYSA-N 2,6-difluoro-4-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]benzonitrile Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C=2C=C(F)C(C#N)=C(F)C=2)=N1 RWXNALYEOBQGBB-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
- 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
- NVSICHZSIOZSHP-UHFFFAOYSA-N 2-[3-[1-(4-bromo-2,5-difluorophenyl)sulfonylpiperidin-4-ylidene]prop-1-ynyl]-6-methylpyridine Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)S(=O)(=O)C=2C(=CC(Br)=C(F)C=2)F)=N1 NVSICHZSIOZSHP-UHFFFAOYSA-N 0.000 claims 1
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- ZEBDEDZCTSIVCE-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(3-phenylphenyl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)=N1 ZEBDEDZCTSIVCE-UHFFFAOYSA-N 0.000 claims 1
- ZGCJBJONYYGXIB-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(4-methylthiophen-2-yl)methanone Chemical compound CC1=CSC(C(=O)N2CCC(CC2)=CC#CC=2N=C(C)C=CC=2)=C1 ZGCJBJONYYGXIB-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
- QPPKVXXPSXYCOS-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-methylsulfanylthiophen-2-yl)methanone Chemical compound S1C(SC)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 QPPKVXXPSXYCOS-UHFFFAOYSA-N 0.000 claims 1
- LJNIRVWQHRMFEI-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 LJNIRVWQHRMFEI-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
- ZXNQPWOFYGZUQF-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-nitrothiophen-2-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2SC(=CC=2)[N+]([O-])=O)=N1 ZXNQPWOFYGZUQF-UHFFFAOYSA-N 0.000 claims 1
- VZAGGTLNLVCVBF-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-(5-phenylfuran-2-yl)methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2OC(=CC=2)C=2C=CC=CC=2)=N1 VZAGGTLNLVCVBF-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
- 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
- QFJXHRJTLUMDBG-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-[3-(trifluoromethoxy)phenyl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(OC(F)(F)F)C=CC=2)=N1 QFJXHRJTLUMDBG-UHFFFAOYSA-N 0.000 claims 1
- NCNWJPDTELTZOW-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2C=C(C=CC=2)C(F)(F)F)=N1 NCNWJPDTELTZOW-UHFFFAOYSA-N 0.000 claims 1
- KTCGQWRXWWYVAJ-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)N2CCOCC2)=N1 KTCGQWRXWWYVAJ-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
- NBKOCVUIYDWMRL-UHFFFAOYSA-N [4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl]-pyrazin-2-ylmethanone Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)C=2N=CC=NC=2)=N1 NBKOCVUIYDWMRL-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
- CWSRVGAEIFSCDS-UHFFFAOYSA-N [5-(furan-2-yl)-1h-pyrazol-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=NNC(=C2)C=2OC=CC=2)=N1 CWSRVGAEIFSCDS-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VAJCYEPHIUALRR-UHFFFAOYSA-N furan-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=CC=2)=N1 VAJCYEPHIUALRR-UHFFFAOYSA-N 0.000 claims 1
- BHFJRTSHKMYHMP-UHFFFAOYSA-N furan-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=COC=C2)=N1 BHFJRTSHKMYHMP-UHFFFAOYSA-N 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
- 239000011630 iodine Substances 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
- 125000002950 monocyclic 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
- BKRZKXKTTVSPMQ-UHFFFAOYSA-N n-[3-[3-[1-(6-methyl-3-nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C#CC=C2CCN(CC2)C=2C(=CC=C(C)N=2)[N+]([O-])=O)=C1 BKRZKXKTTVSPMQ-UHFFFAOYSA-N 0.000 claims 1
- OKYDXDNNCGRANO-UHFFFAOYSA-N n-[3-methyl-4-[4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carbonyl]phenyl]acetamide Chemical compound CC1=CC(NC(=O)C)=CC=C1C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 OKYDXDNNCGRANO-UHFFFAOYSA-N 0.000 claims 1
- DUDLUGRLTVPTNX-UHFFFAOYSA-N n-butyl-n-methyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCCC)CCC1=CC#CC1=CC=CC(C)=N1 DUDLUGRLTVPTNX-UHFFFAOYSA-N 0.000 claims 1
- IWRIPKVWTDSOGO-UHFFFAOYSA-N n-ethyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C(C)C)CC)CCC1=CC#CC1=CC=CC(C)=N1 IWRIPKVWTDSOGO-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
- FRFZTKDETHKTJK-UHFFFAOYSA-N n-methyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]-n-(1-phenylethyl)piperidine-1-carboxamide Chemical compound C=1C=CC=CC=1C(C)N(C)C(=O)N(CC1)CCC1=CC#CC1=CC=CC(C)=N1 FRFZTKDETHKTJK-UHFFFAOYSA-N 0.000 claims 1
- WIEGOXMITHQIFN-UHFFFAOYSA-N n-tert-butyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxamide Chemical compound CC1=CC=CC(C#CC=C2CCN(CC2)C(=O)NC(C)(C)C)=N1 WIEGOXMITHQIFN-UHFFFAOYSA-N 0.000 claims 1
- MBRQXVVRMDOUAR-UHFFFAOYSA-N n-tert-butyl-n-methyl-4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C(C)(C)C)CCC1=CC#CC1=CC=CC(C)=N1 MBRQXVVRMDOUAR-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- WXAFGKCDPPURIY-OVCLIPMQSA-N tert-butyl (3e)-3-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]pyrrolidine-1-carboxylate Chemical compound CC1=CC=CC(C#C\C=C/2CN(CC\2)C(=O)OC(C)(C)C)=N1 WXAFGKCDPPURIY-OVCLIPMQSA-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
- ZTLRBCFUYXAZHX-UHFFFAOYSA-N tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1=CC#CC1=CN=CC(C#N)=C1 ZTLRBCFUYXAZHX-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
- YKAWLNCHRFKROH-UHFFFAOYSA-N tert-butyl 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)(C)C)=N1 YKAWLNCHRFKROH-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
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 101001032845 Homo sapiens Metabotropic glutamate receptor 5 Proteins 0.000 abstract 1
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 abstract 1
- 208000019695 Migraine disease Diseases 0.000 abstract 1
- 208000026723 Urinary tract disease Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
- 102000006239 metabotropic receptors Human genes 0.000 abstract 1
- 108020004083 metabotropic receptors Proteins 0.000 abstract 1
- 206010027599 migraine Diseases 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000002232 neuromuscular Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 208000014001 urinary system disease Diseases 0.000 abstract 1
- 210000001635 urinary tract Anatomy 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95367707P | 2007-08-02 | 2007-08-02 | |
| US4517508P | 2008-04-15 | 2008-04-15 | |
| PCT/EP2008/006351 WO2009015897A1 (en) | 2007-08-02 | 2008-08-01 | Novel heterocyclic compounds as mglu5 antagonists |
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| EP (1) | EP2178858B1 (pt) |
| JP (1) | JP5412430B2 (pt) |
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| CN (1) | CN101821256A (pt) |
| AT (1) | ATE539075T1 (pt) |
| AU (1) | AU2008282032B2 (pt) |
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| WO (1) | WO2009015897A1 (pt) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8937148B2 (en) | 2012-09-07 | 2015-01-20 | Empire Technology Development LLP | Regioregular copolymers and methods for making same |
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| US20100317630A1 (en) * | 2009-02-04 | 2010-12-16 | Recordati Ireland Limited | Novel heterocyclic compounds as mglu5 antagonists |
| WO2011029633A1 (en) * | 2009-09-14 | 2011-03-17 | Recordati Ireland Limited | Heterocyclic mglu5 antagonists |
| WO2012085166A1 (en) * | 2010-12-22 | 2012-06-28 | Merz Pharma Gmbh & Co. Kgaa | Metabotropic glutamate receptor modulators |
| WO2012085167A1 (en) * | 2010-12-22 | 2012-06-28 | Merz Pharma Gmbh & Co. Kgaa | Metabotropic glutamate receptor modulators |
| KR101983421B1 (ko) * | 2011-12-27 | 2019-05-29 | 디에스엠 아이피 어셋츠 비.브이. | 비타민 a 중간체의 촉매 합성법 |
| 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 |
| WO2014117919A1 (en) * | 2013-02-04 | 2014-08-07 | Merck Patent Gmbh | Positive allosteric modulators of mglur3 |
| BR112019027922A2 (pt) * | 2017-06-29 | 2020-08-18 | Recordati Industria Chimica E Farmaceutica Spa | derivados de heterociclilmetilideno e uso dos mesmos como moduladores de receptores de mglur5 |
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| 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 |
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- 2008-08-01 EP EP08785292A patent/EP2178858B1/en active Active
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- 2008-08-01 SI SI200830533T patent/SI2178858T1/sl unknown
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2012
- 2012-03-12 HR HR20120225T patent/HRP20120225T1/hr unknown
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8937148B2 (en) | 2012-09-07 | 2015-01-20 | Empire Technology Development LLP | Regioregular copolymers and methods for making same |
| US9181287B2 (en) | 2012-09-07 | 2015-11-10 | Empire Technology Development Llc | Regioregular copolymers and methods for making same |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2380165T3 (es) | 2012-05-09 |
| EA201000283A1 (ru) | 2010-06-30 |
| AU2008282032A1 (en) | 2009-02-05 |
| CY1112500T1 (el) | 2015-12-09 |
| JP2010535165A (ja) | 2010-11-18 |
| CA2694359A1 (en) | 2009-02-05 |
| ZA201001467B (en) | 2010-11-24 |
| EA018328B1 (ru) | 2013-07-30 |
| CN101821256A (zh) | 2010-09-01 |
| EP2178858A1 (en) | 2010-04-28 |
| KR20100052507A (ko) | 2010-05-19 |
| DK2178858T3 (da) | 2012-03-19 |
| NZ582934A (en) | 2011-10-28 |
| WO2009015897A1 (en) | 2009-02-05 |
| RS52167B (en) | 2012-08-31 |
| SI2178858T1 (sl) | 2012-03-30 |
| PL2178858T3 (pl) | 2012-07-31 |
| PT2178858E (pt) | 2012-02-24 |
| EP2178858B1 (en) | 2011-12-28 |
| BRPI0814182A2 (pt) | 2015-01-27 |
| AU2008282032B2 (en) | 2014-08-07 |
| ATE539075T1 (de) | 2012-01-15 |
| HK1141788A1 (en) | 2010-11-19 |
| JP5412430B2 (ja) | 2014-02-12 |
| IL203659A (en) | 2013-06-27 |
| US8518916B2 (en) | 2013-08-27 |
| US20090042841A1 (en) | 2009-02-12 |
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