CN101845023A - 四唑化合物及其作为代谢型谷氨酸受体拮抗剂的应用 - Google Patents
四唑化合物及其作为代谢型谷氨酸受体拮抗剂的应用 Download PDFInfo
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- CN101845023A CN101845023A CN201010113361A CN201010113361A CN101845023A CN 101845023 A CN101845023 A CN 101845023A CN 201010113361 A CN201010113361 A CN 201010113361A CN 201010113361 A CN201010113361 A CN 201010113361A CN 101845023 A CN101845023 A CN 101845023A
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- China
- Prior art keywords
- tetrazolium
- alkyl
- methyl
- triazole
- phenyl
- 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.)
- Pending
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- -1 Tetrazole compound Chemical class 0.000 title claims abstract description 227
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims abstract description 44
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims abstract description 44
- 239000003825 glutamate receptor antagonist Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 339
- 238000011282 treatment Methods 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 169
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 113
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 103
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 46
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 42
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 41
- 125000004494 ethyl ester group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000003852 triazoles Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- DOLWUAMIJZGVTC-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N1=CC=CN2C=NN=C21 DOLWUAMIJZGVTC-UHFFFAOYSA-N 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 238000001994 activation Methods 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 18
- 230000004913 activation Effects 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 8
- 150000001538 azepines Chemical class 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 230000001684 chronic effect Effects 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 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 description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- GBOKSAOTLOBVGX-UHFFFAOYSA-N 4-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazine-1-carboxylic acid Chemical compound CC(C1=NN(N=N1)C2=CC(=CC=C2)Cl)N3CCN(CC3)C(=O)O GBOKSAOTLOBVGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 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 description 3
- UANUEMSFWMEFRQ-UHFFFAOYSA-N 2h-tetrazol-5-ylmethanethiol Chemical compound SCC1=NN=NN1 UANUEMSFWMEFRQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- ODVVAVWUWZPJIS-UHFFFAOYSA-N 4-[1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethyl]piperazine-1-carboxylic acid Chemical compound CC(C1=NN(N=N1)C2=C(C=CC(=C2)Cl)F)N3CCN(CC3)C(=O)O ODVVAVWUWZPJIS-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- SPEIJELPACDYIR-UHFFFAOYSA-N ClC=1C=CC(=C(C=1)N1N=C(N=N1)CN1CCN(CC1)C(=O)O)F Chemical compound ClC=1C=CC(=C(C=1)N1N=C(N=N1)CN1CCN(CC1)C(=O)O)F SPEIJELPACDYIR-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004480 active ingredient Substances 0.000 claims description 3
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- ODVVAVWUWZPJIS-SECBINFHSA-N 4-[(1R)-1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethyl]piperazine-1-carboxylic acid Chemical compound C[C@H](C1=NN(N=N1)C2=C(C=CC(=C2)Cl)F)N3CCN(CC3)C(=O)O ODVVAVWUWZPJIS-SECBINFHSA-N 0.000 claims description 2
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- 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 description 2
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- CPIMLQSFGIXVKQ-UHFFFAOYSA-N 1-[4-(4-acetylphenyl)piperazin-1-yl]-2-[5-(5-methylfuran-2-yl)tetrazol-2-yl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(C(=O)CN2N=C(N=N2)C=2OC(C)=CC=2)CC1 CPIMLQSFGIXVKQ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- 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
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- 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)
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- 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)
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| CN2005800043701A Expired - Fee Related CN1918137B (zh) | 2004-02-18 | 2005-02-17 | 四唑化合物及其作为代谢型谷氨酸受体拮抗剂的应用 |
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| 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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| IL (1) | IL177056A0 (https=) |
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| WO (1) | WO2005080356A1 (https=) |
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| TW200533664A (en) * | 2004-02-18 | 2005-10-16 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonists |
| 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 |
| WO2006080533A1 (ja) * | 2005-01-31 | 2006-08-03 | Mochida Pharmaceutical Co., Ltd. | 3-アミノ-1,2,4-トリアゾール誘導体 |
| 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 |
| TW200811179A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators VI |
| TW200900065A (en) * | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200900391A (en) * | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-phenyl-piperidin-1-yl)-pyridin-2-one derivatives |
| TW200845978A (en) * | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| US8252937B2 (en) | 2007-09-14 | 2012-08-28 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
| PL2203439T3 (pl) | 2007-09-14 | 2011-06-30 | Addex Pharmaceuticals Sa | 1',3'-dipodstawione-4-fenylo-3,4,5,6-tetrahydro-2H, 1'H-[1, 4']bipirydynylo-2'-ketony |
| US8722894B2 (en) * | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| PE20090875A1 (es) * | 2007-10-19 | 2009-08-08 | Astrazeneca Ab | Derivados de tetrazol como moduladores de los receptores de glutamato metabotropicos |
| EP2212316A4 (en) * | 2007-10-26 | 2012-06-27 | Astrazeneca Ab | DERIVATIVES OF AMINO1,2,4-TRIAZOLES AS MODULATORS OF MGLUR5 |
| WO2009054785A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole ether derivatives as modulators of mglur5 |
| RU2492170C9 (ru) | 2007-11-14 | 2013-12-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2 |
| ES2625817T3 (es) | 2008-08-06 | 2017-07-20 | Medivation Technologies, Inc. | Inhibidores de tipo Dihidropiridoftalazinona de poli(ADP-ribosa)polimerasa (PARP) |
| JP5547194B2 (ja) | 2008-09-02 | 2014-07-09 | 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3−アザビシクロ[3.1.0]ヘキシル誘導体 |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MX2011005981A (es) * | 2008-12-12 | 2011-06-27 | Astrazeneca Ab | Nuevo proceso para preparar 4-[4-metil-5-(alquiltio c1-10/aril c5-10-alquilto c1-6)-4h-1,2,4-triazol-3-il]piridinas. |
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| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
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| TW200533664A (en) * | 2004-02-18 | 2005-10-16 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonists |
-
2005
- 2005-02-17 TW TW094104641A patent/TW200533664A/zh unknown
- 2005-02-17 EP EP05713793.7A patent/EP1716125B1/en not_active Expired - Lifetime
- 2005-02-17 US US10/588,756 patent/US20070197549A1/en not_active Abandoned
- 2005-02-17 AU AU2005214379A patent/AU2005214379B2/en not_active Expired - Fee Related
- 2005-02-17 MY MYPI20050601A patent/MY145075A/en unknown
- 2005-02-17 JP JP2006554236A patent/JP5084269B2/ja not_active Expired - Fee Related
- 2005-02-17 CA CA002556263A patent/CA2556263A1/en not_active Abandoned
- 2005-02-17 WO PCT/US2005/005217 patent/WO2005080356A1/en not_active Ceased
- 2005-02-17 BR BRPI0507498-3A patent/BRPI0507498A/pt not_active IP Right Cessation
- 2005-02-17 CN CN201010113361A patent/CN101845023A/zh active Pending
- 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 RU RU2006127573/04A patent/RU2372347C2/ru not_active IP Right Cessation
- 2005-02-17 MX MXPA06009019A patent/MXPA06009019A/es active IP Right Grant
- 2005-02-17 KR KR1020067015943A patent/KR20070027504A/ko not_active Ceased
- 2005-02-17 SG SG200901214-7A patent/SG150539A1/en unknown
- 2005-02-18 UY UY28763A patent/UY28763A1/es unknown
- 2005-02-18 US US11/060,463 patent/US7691892B2/en not_active Expired - Fee Related
- 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
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 |
| 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 |
| RU2372347C2 (ru) | 2009-11-10 |
| 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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