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) | CN101845023A (https=) |
| AR (1) | AR047812A1 (https=) |
| AU (1) | AU2005214379B2 (https=) |
| BR (1) | BRPI0507498A (https=) |
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| RU (1) | RU2372347C2 (https=) |
| SG (1) | SG150539A1 (https=) |
| TW (1) | TW200533664A (https=) |
| UA (1) | UA85576C2 (https=) |
| UY (1) | UY28763A1 (https=) |
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| 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 |
| US7964619B2 (en) * | 2005-06-03 | 2011-06-21 | The University Of North Carolina At Chapel Hill | Teraryl components as antiparasitic agents |
| AR058807A1 (es) | 2005-09-29 | 2008-02-27 | Astrazeneca Ab | 5-(fenilisoxazoletoxi)-triazol-3-il piridinas sustituidas, para el tratamiento de trastornos mediados por el receptor mglur5 |
| HUP0500921A2 (en) * | 2005-10-05 | 2007-07-30 | Richter Gedeon Nyrt | Tetrazole derivatives, process for their preparation and their use |
| TWI417095B (zh) * | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200808800A (en) * | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| TW200811157A (en) | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators I |
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| PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
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| JP2013544874A (ja) | 2010-12-08 | 2013-12-19 | オスロ ユニヴァーシティー ホスピタル エイチエフ | Ｗｎｔシグナル伝達経路阻害薬としてのトリアゾール誘導体 |
| KR101235100B1 (ko) * | 2010-12-15 | 2013-02-20 | 서강대학교산학협력단 | 트리아졸을 포함하는 삼중연결고리 3차 아민 화합물, 이의 제조방법 및 응용 |
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| 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 |
| TW201605814A (zh) | 2013-11-07 | 2016-02-16 | 拜奧馬林製藥公司 | 用於合成經保護之ｎ－烷基三唑甲醛的三唑中間體 |
| HUE053734T2 (hu) | 2014-01-21 | 2021-07-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait tartalmazó kombinációk és alkalmazásuk |
| KR20220049612A (ko) | 2014-01-21 | 2022-04-21 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
| 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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- 2005-02-17 CN CN201010113361A patent/CN101845023A/zh active Pending
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| RU2111209C1 (ru) * | 1992-03-11 | 1998-05-20 | Зенека Лимитед | Производные хиназолина, способ их получения и фармацевтическая композиция на их основе |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP5084269B2 (ja) | 2012-11-28 |
| JP2007523182A (ja) | 2007-08-16 |
| AR047812A1 (es) | 2006-02-22 |
| TW200533664A (en) | 2005-10-16 |
| US7691892B2 (en) | 2010-04-06 |
| BRPI0507498A (pt) | 2007-07-10 |
| IL177056A0 (en) | 2006-12-10 |
| CN101845023A (zh) | 2010-09-29 |
| MY145075A (en) | 2011-12-15 |
| NO20063470L (no) | 2006-11-17 |
| CN1918137B (zh) | 2012-08-01 |
| US20070197549A1 (en) | 2007-08-23 |
| AU2005214379A1 (en) | 2005-09-01 |
| ZA200606594B (en) | 2007-11-28 |
| MXPA06009019A (es) | 2007-03-08 |
| KR20070027504A (ko) | 2007-03-09 |
| US20060004021A1 (en) | 2006-01-05 |
| UY28763A1 (es) | 2005-06-30 |
| SG150539A1 (en) | 2009-03-30 |
| EP1716125B1 (en) | 2013-06-19 |
| EP1716125A1 (en) | 2006-11-02 |
| WO2005080356A1 (en) | 2005-09-01 |
| CA2556263A1 (en) | 2005-09-01 |
| AU2005214379B2 (en) | 2012-03-22 |
| RU2006127573A (ru) | 2008-03-27 |
| UA85576C2 (ru) | 2009-02-10 |
| CN1918137A (zh) | 2007-02-21 |
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