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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| 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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| 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 |
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| AU2008317544A1 (en) * | 2007-10-26 | 2009-04-30 | 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 |
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| CN102725281A (zh) * | 2009-06-05 | 2012-10-10 | 奥斯陆大学医院公司 | 作为wtn通路抑制剂的氮杂茂类衍生物 |
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| 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 |
| US8541403B2 (en) | 2010-02-03 | 2013-09-24 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(ADP-ribose)polymerase (PARP) for use in treatment of diseases associated with a PTEN deficiency |
| DK2533640T3 (en) | 2010-02-08 | 2017-01-23 | Medivation Technologies Inc | METHODS OF SYNTHESIS OF DIHYDROPYRIDOPHTHALAZINE DERIVATIVES |
| TWI557123B (zh) | 2010-10-21 | 2016-11-11 | 梅迪維新技術公司 | 結晶型（８Ｓ，９Ｒ）－５－氟－８－（４－氟苯基）－９－（１－甲基－１Ｈ－１，２，４－三唑－５－基）－８，９－二氫－２Ｈ－吡啶并［４，３，２－ｄｅ］呔－３（７Ｈ）－酮甲苯磺酸鹽 |
| CN103298809B (zh) | 2010-11-08 | 2016-08-31 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| CA2814998C (en) | 2010-11-08 | 2019-10-29 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| ES2552455T3 (es) | 2010-11-08 | 2015-11-30 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| CA2820800A1 (en) | 2010-12-08 | 2012-06-14 | Oslo University Hospital Hf | Triazole derivatives as wnt signaling pathway inhibitors |
| 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 |
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| IL279202B2 (en) | 2014-01-21 | 2023-09-01 | Janssen Pharmaceutica Nv | Combinations containing positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic subtype 2 receptor and their use |
| US10537573B2 (en) | 2014-01-21 | 2020-01-21 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| 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 |
| WO1993002677A1 (en) | 1991-08-03 | 1993-02-18 | 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 |
| GB0121033D0 (en) | 2001-08-30 | 2001-10-24 | Novartis Ag | Organic compounds |
| WO2003029210A2 (en) * | 2001-10-04 | 2003-04-10 | Merck & Co. Inc. | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| JP4286146B2 (ja) * | 2001-12-18 | 2009-06-24 | メルク エンド カムパニー インコーポレーテッド | メタボトロピックグルタミン酸受容体−５のヘテロアリール置換ピラゾール系調節剤 |
| WO2003077918A1 (en) * | 2002-03-12 | 2003-09-25 | Merck & Co., Inc. | 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 |
| US20070197549A1 (en) * | 2004-02-18 | 2007-08-23 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonists |
-
2005
- 2005-02-17 US US10/588,756 patent/US20070197549A1/en not_active Abandoned
- 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 JP JP2006554236A patent/JP5084269B2/ja not_active Expired - Fee Related
- 2005-02-17 AU AU2005214379A patent/AU2005214379B2/en not_active Expired - Fee Related
- 2005-02-17 KR KR1020067015943A patent/KR20070027504A/ko not_active Ceased
- 2005-02-17 UA UAA200608678A patent/UA85576C2/ru unknown
- 2005-02-17 CN CN2005800043701A patent/CN1918137B/zh not_active Expired - Fee Related
- 2005-02-17 CA CA002556263A patent/CA2556263A1/en not_active Abandoned
- 2005-02-17 TW TW094104641A patent/TW200533664A/zh unknown
- 2005-02-17 CN CN201010113361A patent/CN101845023A/zh active Pending
- 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 MX MXPA06009019A patent/MXPA06009019A/es active IP Right Grant
- 2005-02-17 WO PCT/US2005/005217 patent/WO2005080356A1/en not_active Ceased
- 2005-02-18 US US11/060,463 patent/US7691892B2/en not_active Expired - Fee Related
- 2005-02-18 UY UY28763A patent/UY28763A1/es unknown
- 2005-02-18 AR ARP050100615A patent/AR047812A1/es unknown
-
2006
- 2006-07-25 IL IL177056A patent/IL177056A0/en unknown
- 2006-07-28 NO NO20063470A patent/NO20063470L/no not_active Application Discontinuation
- 2006-08-08 ZA ZA200606594A patent/ZA200606594B/en unknown
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