RU2372347C2 - Соединения тетразола и их применение в качестве антагонистов метаботропного рецептора глутамата - Google Patents
Соединения тетразола и их применение в качестве антагонистов метаботропного рецептора глутамата Download PDFInfo
- Publication number
- RU2372347C2 RU2372347C2 RU2006127573/04A RU2006127573A RU2372347C2 RU 2372347 C2 RU2372347 C2 RU 2372347C2 RU 2006127573/04 A RU2006127573/04 A RU 2006127573/04A RU 2006127573 A RU2006127573 A RU 2006127573A RU 2372347 C2 RU2372347 C2 RU 2372347C2
- Authority
- RU
- Russia
- Prior art keywords
- tetrazol
- methyl
- ethyl
- triazol
- phenyl
- Prior art date
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- -1 Tetrazole compounds Chemical class 0.000 title claims abstract 22
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims abstract 3
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims abstract 3
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 3
- 150000003852 triazoles Chemical group 0.000 claims abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
- 230000002401 inhibitory effect Effects 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 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
- 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
- REOSJUXCEHHINO-UHFFFAOYSA-N 2-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethylsulfanyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=NC=CC=C2NC=1SC(C)C(=N1)N=NN1C1=CC=CC(Cl)=C1 REOSJUXCEHHINO-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
- 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
- RLOOOHWJTLPJOK-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-iodophenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound IC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 RLOOOHWJTLPJOK-UHFFFAOYSA-N 0.000 claims 1
- RAYPHVILNUIXPW-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 RAYPHVILNUIXPW-UHFFFAOYSA-N 0.000 claims 1
- OEMCJXURCVTYQL-UHFFFAOYSA-N 4-[4-methyl-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(N1C)=NN=C1C1=CC=NC=C1 OEMCJXURCVTYQL-UHFFFAOYSA-N 0.000 claims 1
- HBTWXQLKSAOIPA-LLVKDONJSA-N 4-[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=NC=C1 HBTWXQLKSAOIPA-LLVKDONJSA-N 0.000 claims 1
- 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
- HBTWXQLKSAOIPA-UHFFFAOYSA-N 4-[5-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 HBTWXQLKSAOIPA-UHFFFAOYSA-N 0.000 claims 1
- IUJVCUPZEAGDSU-UHFFFAOYSA-N 4-[5-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 IUJVCUPZEAGDSU-UHFFFAOYSA-N 0.000 claims 1
- BMIOWNCHKUHJKT-UHFFFAOYSA-N 4-[5-[1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(Cl)C=2)F)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 BMIOWNCHKUHJKT-UHFFFAOYSA-N 0.000 claims 1
- ANOCVGIRTXMBMF-UHFFFAOYSA-N 4-[5-[1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(Cl)C=2)F)N=C1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 ANOCVGIRTXMBMF-UHFFFAOYSA-N 0.000 claims 1
- HEAYPIQIJLFAIF-UHFFFAOYSA-N 4-[5-[2-[5-(3-chlorophenyl)tetrazol-2-yl]propyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NC(C=2C=C(Cl)C=CC=2)=NN1C(C)CC(N1C)=NN=C1C1=CC=NC=C1 HEAYPIQIJLFAIF-UHFFFAOYSA-N 0.000 claims 1
- ZRPKSYNMJBJRIX-UHFFFAOYSA-N 4-[5-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methoxy]-4-methyl-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)C)N=N2)=C1 ZRPKSYNMJBJRIX-UHFFFAOYSA-N 0.000 claims 1
- KQRVYHXHRQDGOX-UHFFFAOYSA-N 4-[5-[[2-(3-chlorophenyl)tetrazol-5-yl]methoxy]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 KQRVYHXHRQDGOX-UHFFFAOYSA-N 0.000 claims 1
- IIGFWFGPJPEQAS-UHFFFAOYSA-N 4-[5-[[2-(3-chlorophenyl)tetrazol-5-yl]methylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 IIGFWFGPJPEQAS-UHFFFAOYSA-N 0.000 claims 1
- NSZVNIQGBGZITM-UHFFFAOYSA-N 4-[5-[[2-(3-iodophenyl)tetrazol-5-yl]methoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1OCC(=N1)N=NN1C1=CC=CC(I)=C1 NSZVNIQGBGZITM-UHFFFAOYSA-N 0.000 claims 1
- JAHBCKUCQCXRRL-UHFFFAOYSA-N 4-[5-[[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]methylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound FC1=CC=C(Cl)C=C1N1N=C(CSC=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)N=N1 JAHBCKUCQCXRRL-UHFFFAOYSA-N 0.000 claims 1
- NEXXZJKDYDTXEJ-UHFFFAOYSA-N 4-[5-[[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]methylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(=N1)N=NN1C1=CC(Cl)=CC=C1F NEXXZJKDYDTXEJ-UHFFFAOYSA-N 0.000 claims 1
- JVEHTPLJWBUZQH-UHFFFAOYSA-N 4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound CN1C(N)=NN=C1C1=CC=NC=C1 JVEHTPLJWBUZQH-UHFFFAOYSA-N 0.000 claims 1
- BSWZFKOFLUNZSS-UHFFFAOYSA-N 5-[1-[[5-(3,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-2-(3-methylphenyl)tetrazole Chemical compound N=1N=C(C=2C=C(F)C=C(F)C=2)N(CC)C=1SC(C)C(=N1)N=NN1C1=CC=CC(C)=C1 BSWZFKOFLUNZSS-UHFFFAOYSA-N 0.000 claims 1
- BFTYPTVEAUOSMJ-UHFFFAOYSA-N 5-[[5-(3,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-2-(3-methylphenyl)tetrazole Chemical compound N=1N=C(C=2C=C(F)C=C(F)C=2)N(CC)C=1SCC(=N1)N=NN1C1=CC=CC(C)=C1 BFTYPTVEAUOSMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- ZOMNBCKZYULUDN-CQSZACIVSA-N 6-[4-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN([C@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=CC=C(C#N)C=N1 ZOMNBCKZYULUDN-CQSZACIVSA-N 0.000 claims 1
- ZOMNBCKZYULUDN-AWEZNQCLSA-N 6-[4-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN([C@@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=CC=C(C#N)C=N1 ZOMNBCKZYULUDN-AWEZNQCLSA-N 0.000 claims 1
- ZOMNBCKZYULUDN-UHFFFAOYSA-N 6-[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=CC=C(C#N)C=N1 ZOMNBCKZYULUDN-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- RKCVBQKWPOEHKK-UHFFFAOYSA-N 8-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-3-(3,5-difluorophenyl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N1CCCN2C1=NN=C2C1=CC(F)=CC(F)=C1 RKCVBQKWPOEHKK-UHFFFAOYSA-N 0.000 claims 1
- AWNIJWWAGKQJNA-UHFFFAOYSA-N 8-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-3-(4-methoxyphenyl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1CCCN2C(C)C1=NN(C=2C=C(Cl)C=CC=2)N=N1 AWNIJWWAGKQJNA-UHFFFAOYSA-N 0.000 claims 1
- DIOOLZYLVLEVNL-UHFFFAOYSA-N 8-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethyl]-3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound C1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)C(C)C2=NN(N=N2)C=2C=C(I)C=CC=2)=C1 DIOOLZYLVLEVNL-UHFFFAOYSA-N 0.000 claims 1
- SZOBTIJQKLEDAK-UHFFFAOYSA-N 8-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethyl]-3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N1=NN(C=2C=C(I)C=CC=2)N=C1C(C)N1CCCN2C1=NN=C2C1=CC=NC=C1 SZOBTIJQKLEDAK-UHFFFAOYSA-N 0.000 claims 1
- UHGALFACSQZCHU-UHFFFAOYSA-N 8-[[2-(3-chlorophenyl)tetrazol-5-yl]methyl]-3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound C1=NC(OC)=CC(C=2N3CCCN(CC4=NN(N=N4)C=4C=C(Cl)C=CC=4)C3=NN=2)=C1 UHGALFACSQZCHU-UHFFFAOYSA-N 0.000 claims 1
- RMCXBFFVYMLSBO-UHFFFAOYSA-N 8-[[2-(3-iodophenyl)tetrazol-5-yl]methyl]-3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound IC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCC3)N=N2)=C1 RMCXBFFVYMLSBO-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 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 1
- LESKYBRZEZJQOS-UHFFFAOYSA-N ethyl 4-[1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C)C1=NN(C=2C(=CC=C(Cl)C=2)F)N=N1 LESKYBRZEZJQOS-UHFFFAOYSA-N 0.000 claims 1
- HOUFSJNBIFUWKT-UHFFFAOYSA-N ethyl 4-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C(=CC=C(C)C=2)F)N=N1 HOUFSJNBIFUWKT-UHFFFAOYSA-N 0.000 claims 1
- FLINNCJLYXBVMD-UHFFFAOYSA-N ethyl 4-[[2-(3-chlorophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(Cl)C=CC=2)N=N1 FLINNCJLYXBVMD-UHFFFAOYSA-N 0.000 claims 1
- VMGBXXDDLLFQDH-UHFFFAOYSA-N ethyl 4-[[2-(3-cyanophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(C=CC=2)C#N)N=N1 VMGBXXDDLLFQDH-UHFFFAOYSA-N 0.000 claims 1
- YSVIACGQDSBPCZ-UHFFFAOYSA-N ethyl 4-[[2-(3-iodophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(I)C=CC=2)N=N1 YSVIACGQDSBPCZ-UHFFFAOYSA-N 0.000 claims 1
- XBNAVIBRBWYJDK-UHFFFAOYSA-N ethyl 4-[[2-(3-methylphenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(C)C=CC=2)N=N1 XBNAVIBRBWYJDK-UHFFFAOYSA-N 0.000 claims 1
- SKSUCCHHYXGTKI-UHFFFAOYSA-N ethyl 4-[[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C(=CC=C(Cl)C=2)F)N=N1 SKSUCCHHYXGTKI-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- ZELWWLDSSVWOGK-UHFFFAOYSA-N n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound CN1C(NC)=NN=C1C1=CC=NC=C1 ZELWWLDSSVWOGK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- 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
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54529104P | 2004-02-18 | 2004-02-18 | |
| US60/545,291 | 2004-02-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006127573A RU2006127573A (ru) | 2008-03-27 |
| RU2372347C2 true RU2372347C2 (ru) | 2009-11-10 |
Family
ID=34886129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006127573/04A RU2372347C2 (ru) | 2004-02-18 | 2005-02-17 | Соединения тетразола и их применение в качестве антагонистов метаботропного рецептора глутамата |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20070197549A1 (https=) |
| EP (1) | EP1716125B1 (https=) |
| JP (1) | JP5084269B2 (https=) |
| KR (1) | KR20070027504A (https=) |
| CN (2) | CN1918137B (https=) |
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| TW (1) | TW200533664A (https=) |
| UA (1) | UA85576C2 (https=) |
| UY (1) | UY28763A1 (https=) |
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Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005080356A1 (en) * | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| 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 |
| AR065622A1 (es) * | 2007-03-07 | 2009-06-17 | Ortho Mcneil Janssen Pharm | Derivados de 3-ciano -4- (4-fenil- piperidin -1- il) piridin -2- ona |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) * | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| PL2200985T3 (pl) | 2007-09-14 | 2011-12-30 | Ortho Mcneil Janssen Pharmaceuticals Inc | 1,3-Dipodstawione-4-(arylo-X-fenylo)-1H-pirydyn-2-ony |
| 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 |
| EP2344470B1 (en) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| WO2010043396A1 (en) | 2008-10-16 | 2010-04-22 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| JP5690277B2 (ja) | 2008-11-28 | 2015-03-25 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体の調節因子としてのインドールおよびベンゾオキサジン誘導体 |
| BRPI0923215A2 (pt) * | 2008-12-12 | 2017-06-06 | Astrazeneca Ab | método para fabricar um composto. |
| EP2379531A1 (en) * | 2008-12-18 | 2011-10-26 | AstraZeneca AB | Processes for the manufacture of 3-{4-methyl-5- [ (ir) -1- (2- (3-methylphenyl) -2h-tetrazol-5-yl) -ethoxy]-4h- [1,2, 4]triazol-3-yl} -pyridine, 4-methyl-3-methylthio-5- (3- pyridyl)-l,2,4-triazole, and (ir) -1- [2- (3-methylphenyl) -2h- tetrazol-5-yl]ethanol |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US20100273805A1 (en) * | 2009-04-23 | 2010-10-28 | Astrazeneca Ab | Sulphide bridged derivatives as modulators of mglur5 733 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| 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 |
| CA2764339A1 (en) * | 2009-06-05 | 2010-12-09 | Oslo University Hospital Hf | Azole derivatives as wtn pathway inhibitors |
| 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 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| 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 |
| EP2531033A4 (en) | 2010-02-03 | 2013-07-31 | Biomarin Pharm Inc | POLY (ADP-RIBOSE) POLYMERASE (PARP) DIHYDROPYRIDOPHTHALAZINE HEMMER FOR USE IN THE TREATMENT OF PTEN-LACK ASSOCIATED DISEASES |
| 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 |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663332A (en) * | 1985-10-10 | 1987-05-05 | Hoffman-La Roche Inc. | 5-substituted N-alkylated tetrazoles |
| RU2111209C1 (ru) * | 1992-03-11 | 1998-05-20 | Зенека Лимитед | Производные хиназолина, способ их получения и фармацевтическая композиция на их основе |
| RU2203889C2 (ru) * | 1997-07-11 | 2003-05-10 | Новартис Аг | Производные пиридина, фармацевтическая композиция, обладающая антагонистическим действием на mglu r5 человека |
| RU2317985C1 (ru) * | 2003-10-07 | 2008-02-27 | Ханми Фарм. Ко., Лтд. | Соединения, способ их получения и фармацевтическая композиция на их основе |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509153A (en) * | 1967-03-24 | 1970-04-28 | Miles Lab | 5-phenyl (or 5-phenylalkyl)-2-(omega-(4-phenyl-1-piperazinyl)alkyl)tetrazoles |
| EP0596933A1 (en) | 1991-08-03 | 1994-05-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| 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 |
| JP4303109B2 (ja) * | 2001-10-04 | 2009-07-29 | メルク エンド カムパニー インコーポレーテッド | 代謝共役型グルタミン酸受容体−５のヘテロアリール置換テトラゾール調節剤 |
| 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 |
| WO2005080356A1 (en) * | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
-
2005
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- 2005-02-17 CA CA002556263A patent/CA2556263A1/en not_active Abandoned
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- 2005-02-17 KR KR1020067015943A patent/KR20070027504A/ko not_active Ceased
- 2005-02-17 SG SG200901214-7A patent/SG150539A1/en unknown
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- 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
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- 2005-02-18 AR ARP050100615A patent/AR047812A1/es unknown
- 2005-02-18 UY UY28763A patent/UY28763A1/es unknown
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- 2006-07-28 NO NO20063470A patent/NO20063470L/no not_active Application Discontinuation
- 2006-08-08 ZA ZA200606594A patent/ZA200606594B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663332A (en) * | 1985-10-10 | 1987-05-05 | Hoffman-La Roche Inc. | 5-substituted N-alkylated tetrazoles |
| RU2111209C1 (ru) * | 1992-03-11 | 1998-05-20 | Зенека Лимитед | Производные хиназолина, способ их получения и фармацевтическая композиция на их основе |
| RU2203889C2 (ru) * | 1997-07-11 | 2003-05-10 | Новартис Аг | Производные пиридина, фармацевтическая композиция, обладающая антагонистическим действием на mglu r5 человека |
| RU2317985C1 (ru) * | 2003-10-07 | 2008-02-27 | Ханми Фарм. Ко., Лтд. | Соединения, способ их получения и фармацевтическая композиция на их основе |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200533664A (en) | 2005-10-16 |
| US20070197549A1 (en) | 2007-08-23 |
| IL177056A0 (en) | 2006-12-10 |
| MXPA06009019A (es) | 2007-03-08 |
| SG150539A1 (en) | 2009-03-30 |
| CN1918137B (zh) | 2012-08-01 |
| JP5084269B2 (ja) | 2012-11-28 |
| KR20070027504A (ko) | 2007-03-09 |
| CA2556263A1 (en) | 2005-09-01 |
| US7691892B2 (en) | 2010-04-06 |
| WO2005080356A1 (en) | 2005-09-01 |
| CN1918137A (zh) | 2007-02-21 |
| RU2006127573A (ru) | 2008-03-27 |
| EP1716125B1 (en) | 2013-06-19 |
| AU2005214379A1 (en) | 2005-09-01 |
| UY28763A1 (es) | 2005-06-30 |
| JP2007523182A (ja) | 2007-08-16 |
| US20060004021A1 (en) | 2006-01-05 |
| AU2005214379B2 (en) | 2012-03-22 |
| UA85576C2 (ru) | 2009-02-10 |
| AR047812A1 (es) | 2006-02-22 |
| BRPI0507498A (pt) | 2007-07-10 |
| EP1716125A1 (en) | 2006-11-02 |
| ZA200606594B (en) | 2007-11-28 |
| NO20063470L (no) | 2006-11-17 |
| MY145075A (en) | 2011-12-15 |
| CN101845023A (zh) | 2010-09-29 |
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