JP2007523182A5 - - Google Patents
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- JP2007523182A5 JP2007523182A5 JP2006554236A JP2006554236A JP2007523182A5 JP 2007523182 A5 JP2007523182 A5 JP 2007523182A5 JP 2006554236 A JP2006554236 A JP 2006554236A JP 2006554236 A JP2006554236 A JP 2006554236A JP 2007523182 A5 JP2007523182 A5 JP 2007523182A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrazol
- alkyl
- methyl
- ethyl
- triazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 84
- 150000001875 compounds Chemical class 0.000 claims 23
- -1 C 0-6 alkylcyano Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 150000003852 triazoles Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 5
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- YPYUIVBSDKNLQK-UHFFFAOYSA-N 4-[5-[2-[2-(3-chlorophenyl)tetrazol-5-yl]ethenyl]-4-ethyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(CC)C=1C=CC(=N1)N=NN1C1=CC=CC(Cl)=C1 YPYUIVBSDKNLQK-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- CLJVAJIVLWFAJD-UHFFFAOYSA-N ethyl 4-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NN(C=2C=C(Cl)C=CC=2)N=N1 CLJVAJIVLWFAJD-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- HBTWXQLKSAOIPA-NSHDSACASA-N 4-[5-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound O([C@@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C1=CC=NC=C1 HBTWXQLKSAOIPA-NSHDSACASA-N 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- MONSKCOKXVTTBO-UHFFFAOYSA-N n,4-dimethyl-n-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethyl]-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 MONSKCOKXVTTBO-UHFFFAOYSA-N 0.000 claims 2
- DPVHQPGVGADSNV-UHFFFAOYSA-N n,4-dimethyl-n-[[2-(3-methylphenyl)tetrazol-5-yl]methyl]-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(C)=C1 DPVHQPGVGADSNV-UHFFFAOYSA-N 0.000 claims 2
- MTGWILXIKBIHEP-UHFFFAOYSA-N n-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 MTGWILXIKBIHEP-UHFFFAOYSA-N 0.000 claims 2
- YXVILKGFMGECJM-UHFFFAOYSA-N n-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 YXVILKGFMGECJM-UHFFFAOYSA-N 0.000 claims 2
- VLWCHPQMDNHKFE-UHFFFAOYSA-N n-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC(C)=CC=C1F VLWCHPQMDNHKFE-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- DQVWOISJGINRAS-UHFFFAOYSA-N 1-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-4-(3-nitropyridin-2-yl)piperazine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N(CC1)CCN1C1=NC=CC=C1[N+]([O-])=O DQVWOISJGINRAS-UHFFFAOYSA-N 0.000 claims 1
- ZQOTYMUJVHFJMO-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)tetrazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethanol Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(O)CC(N1C2CC2)=NN=C1C1=CC=NC=C1 ZQOTYMUJVHFJMO-UHFFFAOYSA-N 0.000 claims 1
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
- BKKWKXDUSCUVDZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(1-phenylprop-1-en-2-yl)tetrazole Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)=CC1=CC=CC=C1 BKKWKXDUSCUVDZ-UHFFFAOYSA-N 0.000 claims 1
- BMOGSBKIRGTSIJ-SNVBAGLBSA-N 2-(3-chlorophenyl)-5-[(1r)-1-[[5-(3,5-difluorophenyl)-4-methyl-1,2,4-triazol-3-yl]oxy]ethyl]tetrazole Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C1=CC(F)=CC(F)=C1 BMOGSBKIRGTSIJ-SNVBAGLBSA-N 0.000 claims 1
- YRKGWCXYMUDYGM-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)tetrazol-5-yl]-1-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethanol Chemical compound N=1N=C(C=2C=CN=CC=2)N(C2CC2)C=1C(O)CC(=N1)N=NN1C1=CC=CC(Cl)=C1 YRKGWCXYMUDYGM-UHFFFAOYSA-N 0.000 claims 1
- ITQPPSBTMMYLLO-UHFFFAOYSA-N 2-[4-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N(CC1)CCN1C1=NC=CC=C1C#N ITQPPSBTMMYLLO-UHFFFAOYSA-N 0.000 claims 1
- DQBKXYAMRHSZII-UHFFFAOYSA-N 3-(2-chloro-6-methoxypyridin-4-yl)-8-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound ClC1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)C(C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)=C1 DQBKXYAMRHSZII-UHFFFAOYSA-N 0.000 claims 1
- ZXCMVOMJHFQABJ-CYBMUJFWSA-N 3-[4-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound C1CN([C@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=NC=CN=C1C#N ZXCMVOMJHFQABJ-CYBMUJFWSA-N 0.000 claims 1
- ZXCMVOMJHFQABJ-ZDUSSCGKSA-N 3-[4-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound C1CN([C@@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=NC=CN=C1C#N ZXCMVOMJHFQABJ-ZDUSSCGKSA-N 0.000 claims 1
- ZXCMVOMJHFQABJ-UHFFFAOYSA-N 3-[4-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N(CC1)CCN1C1=NC=CN=C1C#N ZXCMVOMJHFQABJ-UHFFFAOYSA-N 0.000 claims 1
- DUWWRSFBHUBVGQ-UHFFFAOYSA-N 3-[4-methyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-1,2,4-triazol-3-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)SC(N1C)=NN=C1C1=CC=CC(C#N)=C1 DUWWRSFBHUBVGQ-UHFFFAOYSA-N 0.000 claims 1
- UAEKNXTUBOOSAU-UHFFFAOYSA-N 3-[4-methyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methylsulfanyl]-1,2,4-triazol-3-yl]benzonitrile Chemical compound CC1=CC=CC(N2N=C(CSC=3N(C(C=4C=C(C=CC=4)C#N)=NN=3)C)N=N2)=C1 UAEKNXTUBOOSAU-UHFFFAOYSA-N 0.000 claims 1
- HRTYJIIATXTUSW-LLVKDONJSA-N 3-[5-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C1=CC=CN=C1 HRTYJIIATXTUSW-LLVKDONJSA-N 0.000 claims 1
- PCXSZTOBRWASBW-CQSZACIVSA-N 3-[5-[(1r)-1-[3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl]ethyl]tetrazol-2-yl]benzonitrile Chemical compound C1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)[C@H](C)C2=NN(N=N2)C=2C=C(C=CC=2)C#N)=C1 PCXSZTOBRWASBW-CQSZACIVSA-N 0.000 claims 1
- PCXSZTOBRWASBW-AWEZNQCLSA-N 3-[5-[(1s)-1-[3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl]ethyl]tetrazol-2-yl]benzonitrile Chemical compound C1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)[C@@H](C)C2=NN(N=N2)C=2C=C(C=CC=2)C#N)=C1 PCXSZTOBRWASBW-AWEZNQCLSA-N 0.000 claims 1
- YKMQYRLZYIFWBU-UHFFFAOYSA-N 3-[5-[(3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepin-9-yl)methyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCCC3)N=N2)=C1 YKMQYRLZYIFWBU-UHFFFAOYSA-N 0.000 claims 1
- KNUPDYJEUFQYLB-UHFFFAOYSA-N 3-[5-[(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)methyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCC3)N=N2)=C1 KNUPDYJEUFQYLB-UHFFFAOYSA-N 0.000 claims 1
- RRGSLQHYXCPORA-UHFFFAOYSA-N 3-[5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxymethyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 RRGSLQHYXCPORA-UHFFFAOYSA-N 0.000 claims 1
- QAWNJLHEHASGJD-UHFFFAOYSA-N 3-[5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 QAWNJLHEHASGJD-UHFFFAOYSA-N 0.000 claims 1
- QVHFWIURBFHEIS-UHFFFAOYSA-N 3-[5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxymethyl]tetrazol-2-yl]benzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1OCC(=N1)N=NN1C1=CC=CC(C#N)=C1 QVHFWIURBFHEIS-UHFFFAOYSA-N 0.000 claims 1
- WQFWORISFHFDSU-UHFFFAOYSA-N 3-[5-[1-(3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepin-9-yl)ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)N1CCCCN2C1=NN=C2C1=CC=NC=C1 WQFWORISFHFDSU-UHFFFAOYSA-N 0.000 claims 1
- SHJRYGHPCXSPDP-UHFFFAOYSA-N 3-[5-[1-(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)N1CCCN2C1=NN=C2C1=CC=NC=C1 SHJRYGHPCXSPDP-UHFFFAOYSA-N 0.000 claims 1
- RRUFGIVOAHHNNN-UHFFFAOYSA-N 3-[5-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxy]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 RRUFGIVOAHHNNN-UHFFFAOYSA-N 0.000 claims 1
- BFNIILUBQDRTGP-UHFFFAOYSA-N 3-[5-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 BFNIILUBQDRTGP-UHFFFAOYSA-N 0.000 claims 1
- CMNBYTKKQRMLOJ-UHFFFAOYSA-N 3-[5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxy]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 CMNBYTKKQRMLOJ-UHFFFAOYSA-N 0.000 claims 1
- DNGCEZVKZWLLOW-UHFFFAOYSA-N 3-[5-[1-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanyl]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 DNGCEZVKZWLLOW-UHFFFAOYSA-N 0.000 claims 1
- PCXSZTOBRWASBW-UHFFFAOYSA-N 3-[5-[1-[3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl]ethyl]tetrazol-2-yl]benzonitrile Chemical compound C1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)C(C)C2=NN(N=N2)C=2C=C(C=CC=2)C#N)=C1 PCXSZTOBRWASBW-UHFFFAOYSA-N 0.000 claims 1
- GKPBQXKXCXURER-UHFFFAOYSA-N 3-[5-[1-[methyl-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)amino]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 GKPBQXKXCXURER-UHFFFAOYSA-N 0.000 claims 1
- IUPOLWYCXUJISC-UHFFFAOYSA-N 3-[5-[[3-(2,6-dimethoxypyrimidin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl]methyl]tetrazol-2-yl]benzonitrile Chemical compound COC1=NC(OC)=CC(C=2N3CCCN(CC4=NN(N=N4)C=4C=C(C=CC=4)C#N)C3=NN=2)=N1 IUPOLWYCXUJISC-UHFFFAOYSA-N 0.000 claims 1
- REIRCBSYUKMVNY-UHFFFAOYSA-N 3-[5-[[3-(2-methoxypyridin-4-yl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepin-9-yl]methyl]tetrazol-2-yl]benzonitrile Chemical compound C1=NC(OC)=CC(C=2N3CCCCN(CC4=NN(N=N4)C=4C=C(C=CC=4)C#N)C3=NN=2)=C1 REIRCBSYUKMVNY-UHFFFAOYSA-N 0.000 claims 1
- PVIRBSOHWVJPTQ-UHFFFAOYSA-N 3-[5-[[3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl]methyl]tetrazol-2-yl]benzonitrile Chemical compound C1=NC(OC)=CC(C=2N3CCCN(CC4=NN(N=N4)C=4C=C(C=CC=4)C#N)C3=NN=2)=C1 PVIRBSOHWVJPTQ-UHFFFAOYSA-N 0.000 claims 1
- YNYJLGIRFUGDEY-UHFFFAOYSA-N 3-[5-[[methyl-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)amino]methyl]tetrazol-2-yl]benzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(C#N)=C1 YNYJLGIRFUGDEY-UHFFFAOYSA-N 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- BZTXEMPYJURSGN-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 BZTXEMPYJURSGN-UHFFFAOYSA-N 0.000 claims 1
- KUWCVGDHTYYBSL-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 KUWCVGDHTYYBSL-UHFFFAOYSA-N 0.000 claims 1
- HMBGXKUWLFCCOG-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(I)C=CC=2)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 HMBGXKUWLFCCOG-UHFFFAOYSA-N 0.000 claims 1
- JRSQOTYVSVQHBW-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 JRSQOTYVSVQHBW-UHFFFAOYSA-N 0.000 claims 1
- GXRZVIJKAXQXQD-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 GXRZVIJKAXQXQD-UHFFFAOYSA-N 0.000 claims 1
- YEGUVXPNFFXTHC-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=C(F)C(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 YEGUVXPNFFXTHC-UHFFFAOYSA-N 0.000 claims 1
- WGPNVMJAZIFZHJ-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=C(F)C(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 WGPNVMJAZIFZHJ-UHFFFAOYSA-N 0.000 claims 1
- OPRJFHQMQBEOEB-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 OPRJFHQMQBEOEB-UHFFFAOYSA-N 0.000 claims 1
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- BKAIMRACVVBEGA-UHFFFAOYSA-N 4-[5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 BKAIMRACVVBEGA-UHFFFAOYSA-N 0.000 claims 1
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| US54529104P | 2004-02-18 | 2004-02-18 | |
| US60/545,291 | 2004-02-18 | ||
| PCT/US2005/005217 WO2005080356A1 (en) | 2004-02-18 | 2005-02-17 | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
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| JP2007523182A JP2007523182A (ja) | 2007-08-16 |
| JP2007523182A5 true JP2007523182A5 (https=) | 2008-04-03 |
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| US (2) | US20070197549A1 (https=) |
| EP (1) | EP1716125B1 (https=) |
| JP (1) | JP5084269B2 (https=) |
| KR (1) | KR20070027504A (https=) |
| CN (2) | CN1918137B (https=) |
| AR (1) | AR047812A1 (https=) |
| AU (1) | AU2005214379B2 (https=) |
| BR (1) | BRPI0507498A (https=) |
| CA (1) | CA2556263A1 (https=) |
| IL (1) | IL177056A0 (https=) |
| MX (1) | MXPA06009019A (https=) |
| MY (1) | MY145075A (https=) |
| NO (1) | NO20063470L (https=) |
| RU (1) | RU2372347C2 (https=) |
| SG (1) | SG150539A1 (https=) |
| TW (1) | TW200533664A (https=) |
| UA (1) | UA85576C2 (https=) |
| UY (1) | UY28763A1 (https=) |
| WO (1) | WO2005080356A1 (https=) |
| ZA (1) | ZA200606594B (https=) |
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| TW200538108A (en) | 2004-02-19 | 2005-12-01 | Astrazeneca Ab | Fused heterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| JPWO2006080533A1 (ja) * | 2005-01-31 | 2008-06-19 | 持田製薬株式会社 | ３−アミノ−１，２，４−トリアゾール誘導体 |
| US7964619B2 (en) * | 2005-06-03 | 2011-06-21 | The University Of North Carolina At Chapel Hill | Teraryl components as antiparasitic agents |
| US8101636B2 (en) * | 2005-06-03 | 2012-01-24 | The University Of North Carolina At Chapel Hill | Linear dicationic terphenyls and their aza analogues as antiparasitic agents |
| UY29796A1 (es) | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| HUP0500921A2 (en) * | 2005-10-05 | 2007-07-30 | Richter Gedeon Nyrt | Tetrazole derivatives, process for their preparation and their use |
| AR059898A1 (es) * | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200811179A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators VI |
| TW200811157A (en) | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators I |
| TW200808800A (en) * | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
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| TW200900065A (en) * | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
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| SI2203439T1 (sl) | 2007-09-14 | 2011-05-31 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni |
| CN101801930B (zh) * | 2007-09-14 | 2013-01-30 | 奥梅-杨森制药有限公司 | 1,3-二取代的-4-苯基-1h-吡啶-2-酮 |
| BRPI0818448A2 (pt) * | 2007-10-19 | 2015-05-12 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos para o tratamento ou prevenção de um distúrbio madiano pelo receptor mglur5. |
| TW200922585A (en) * | 2007-10-26 | 2009-06-01 | Astrazeneca Ab | Amino 1,2,4-triazole derivatives as modulators of mGluR5 |
| WO2009054785A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole ether derivatives as modulators of mglur5 |
| CN101861316B (zh) | 2007-11-14 | 2013-08-21 | 奥梅-杨森制药有限公司 | 咪唑并[1,2-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| CN104478875B (zh) | 2008-08-06 | 2017-04-12 | 麦迪韦逊科技有限公司 | 聚(adp‑核糖)聚合酶(parp)的二氢吡啶并酞嗪酮抑制剂 |
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| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
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| ES2443578T3 (es) * | 2009-12-29 | 2014-02-19 | Eli Lilly And Company | Compuestos de tetrahidrotriazolopiridina como potenciadores de receptores selectivos de mGlu5 útiles para el tratamiento de la esquizofrenia |
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| JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | ＣＲＦ−１受容体アンタゴニストとしてのピラゾロ［５，１ｂ］オキサゾール誘導体 |
| JP5748777B2 (ja) | 2010-02-02 | 2015-07-15 | ノバルティス アーゲー | Ｃｒｆ受容体アンタゴニストとしてのシクロヘキシルアミド誘導体 |
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| KR101826652B1 (ko) | 2010-02-08 | 2018-02-07 | 메디베이션 테크놀로지즈, 인크. | 디히드로피리도프탈라지논 유도체의 합성 방법 |
| KR20190120458A (ko) | 2010-10-21 | 2019-10-23 | 메디베이션 테크놀로지즈 엘엘씨 | 결정질의 (8s,9r)-5-플루오로-8-(4-플루오로페닐)-9-(1-메틸-1h-1,2,4-트리아졸-5-일)-8,9-디하이드로-2h-피리도[4,3,2-de]프탈라진-3(7h)-온 토실레이트 염 |
| ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
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| AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| RU2013128448A (ru) | 2010-12-08 | 2015-01-20 | Осло Юниверсити Хоспитал Хф | Производные триазола в качестве ингибиторов сигнального пути wnt |
| KR101235100B1 (ko) * | 2010-12-15 | 2013-02-20 | 서강대학교산학협력단 | 트리아졸을 포함하는 삼중연결고리 3차 아민 화합물, 이의 제조방법 및 응용 |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| CN105916846A (zh) * | 2013-11-07 | 2016-08-31 | 麦迪韦逊科技有限公司 | 用于合成经保护的n-烷基三唑甲醛的三唑中间体 |
| MX386697B (es) | 2014-01-21 | 2025-03-19 | Janssen Pharmaceutica Nv | Combinaciones que comprenden agonistas ortostericos o moduladores alostericos positivos del receptor glutamatergico metabotropico de subtipo 2 y su uso |
| ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
| CN111269192A (zh) * | 2020-02-25 | 2020-06-12 | 成都睿智化学研究有限公司 | 一种5-羟甲基四氮唑及其衍生物的合成方法 |
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| US3509153A (en) * | 1967-03-24 | 1970-04-28 | Miles Lab | 5-phenyl (or 5-phenylalkyl)-2-(omega-(4-phenyl-1-piperazinyl)alkyl)tetrazoles |
| US4663332A (en) * | 1985-10-10 | 1987-05-05 | Hoffman-La Roche Inc. | 5-substituted N-alkylated tetrazoles |
| EP0596933A1 (en) | 1991-08-03 | 1994-05-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| GB9205320D0 (en) * | 1992-03-11 | 1992-04-22 | Ici Plc | Anti-tumour compounds |
| TW544448B (en) * | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
| DE10023430A1 (de) | 2000-05-12 | 2001-11-15 | Bayer Ag | Substituierte N-Benzoyl-N'-(tetrazolylphenyl)-harnstoffe |
| GB0115862D0 (en) | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
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| DE60223720T2 (de) * | 2001-12-18 | 2008-10-30 | Merck & Co., Inc. | Heteroaryl-substituierte pyrazol-modulatoren des metabotropen glutamatrezeptors-5 |
| EP1485093B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| KR100557093B1 (ko) * | 2003-10-07 | 2006-03-03 | 한미약품 주식회사 | 다약제 내성 저해 활성을 갖는 테트라졸 유도체 및 그의제조방법 |
| WO2005080356A1 (en) * | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
-
2005
- 2005-02-17 WO PCT/US2005/005217 patent/WO2005080356A1/en not_active Ceased
- 2005-02-17 CA CA002556263A patent/CA2556263A1/en not_active Abandoned
- 2005-02-17 MX MXPA06009019A patent/MXPA06009019A/es active IP Right Grant
- 2005-02-17 KR KR1020067015943A patent/KR20070027504A/ko not_active Ceased
- 2005-02-17 SG SG200901214-7A patent/SG150539A1/en unknown
- 2005-02-17 MY MYPI20050601A patent/MY145075A/en unknown
- 2005-02-17 BR BRPI0507498-3A patent/BRPI0507498A/pt not_active IP Right Cessation
- 2005-02-17 RU RU2006127573/04A patent/RU2372347C2/ru not_active IP Right Cessation
- 2005-02-17 EP EP05713793.7A patent/EP1716125B1/en not_active Expired - Lifetime
- 2005-02-17 TW TW094104641A patent/TW200533664A/zh unknown
- 2005-02-17 US US10/588,756 patent/US20070197549A1/en not_active Abandoned
- 2005-02-17 AU AU2005214379A patent/AU2005214379B2/en not_active Expired - Fee Related
- 2005-02-17 CN CN2005800043701A patent/CN1918137B/zh not_active Expired - Fee Related
- 2005-02-17 JP JP2006554236A patent/JP5084269B2/ja not_active Expired - Fee Related
- 2005-02-17 CN CN201010113361A patent/CN101845023A/zh active Pending
- 2005-02-17 UA UAA200608678A patent/UA85576C2/ru unknown
- 2005-02-18 AR ARP050100615A patent/AR047812A1/es unknown
- 2005-02-18 UY UY28763A patent/UY28763A1/es unknown
- 2005-02-18 US US11/060,463 patent/US7691892B2/en not_active Expired - Fee Related
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- 2006-07-25 IL IL177056A patent/IL177056A0/en unknown
- 2006-07-28 NO NO20063470A patent/NO20063470L/no not_active Application Discontinuation
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