KR20070027503A - 트리아졸 화합물 및 대사성 글루타메이트 수용체길항제로서 이들의 용도 - Google Patents
트리아졸 화합물 및 대사성 글루타메이트 수용체길항제로서 이들의 용도 Download PDFInfo
- Publication number
- KR20070027503A KR20070027503A KR1020067015941A KR20067015941A KR20070027503A KR 20070027503 A KR20070027503 A KR 20070027503A KR 1020067015941 A KR1020067015941 A KR 1020067015941A KR 20067015941 A KR20067015941 A KR 20067015941A KR 20070027503 A KR20070027503 A KR 20070027503A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- triazol
- group
- compound
- methyl
- 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.)
- Withdrawn
Links
- -1 Triazole compounds Chemical class 0.000 title claims description 54
- 230000002503 metabolic effect Effects 0.000 title description 10
- 239000003825 glutamate receptor antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 238000011282 treatment Methods 0.000 claims abstract description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 28
- 230000001404 mediated effect Effects 0.000 claims abstract description 17
- 150000004677 hydrates Chemical class 0.000 claims abstract description 11
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims abstract description 10
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 468
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 24
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 22
- 102000005962 receptors Human genes 0.000 claims description 21
- 108020003175 receptors Proteins 0.000 claims description 21
- 230000004913 activation Effects 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- LDPBANLLWPELSD-UHFFFAOYSA-N 4-[5-[[1-(3-chlorophenyl)triazol-4-yl]methylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(N2N=NC(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=C2)=C1 LDPBANLLWPELSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- MMJDGAKOJHOGOU-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-[1-[methyl-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)amino]ethyl]-1h-1,2,4-triazol-3-one Chemical compound N=1N(C=2C=C(Cl)C=CC=2)C(=O)NC=1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 MMJDGAKOJHOGOU-UHFFFAOYSA-N 0.000 claims description 3
- BNWCCYMBVOENBV-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[(4-methyl-5-pyridin-3-yl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3,4-oxadiazol-2-one Chemical compound N=1N=C(C=2C=NC=CC=2)N(C)C=1SCC(OC1=O)=NN1C1=CC=CC(Cl)=C1 BNWCCYMBVOENBV-UHFFFAOYSA-N 0.000 claims description 3
- QVJHKDQDIDLCAR-UHFFFAOYSA-N 4-[5-[1-[1-(3-chlorophenyl)pyrazol-4-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound C1=NN(C=2C=C(Cl)C=CC=2)C=C1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 QVJHKDQDIDLCAR-UHFFFAOYSA-N 0.000 claims description 3
- OFVMQJXJOIMQNQ-UHFFFAOYSA-N 4-[5-[1-[2-(3-chlorophenyl)triazol-4-yl]ethylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound C1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 OFVMQJXJOIMQNQ-UHFFFAOYSA-N 0.000 claims description 3
- XTCYVWKPHZLRAF-UHFFFAOYSA-N 4-[5-[[1-(3-chlorophenyl)-1,2,4-triazol-3-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=C2)=C1 XTCYVWKPHZLRAF-UHFFFAOYSA-N 0.000 claims description 3
- ZTEZLFTXZTWVRA-UHFFFAOYSA-N 4-[5-[[1-(3-chlorophenyl)-1,2,4-triazol-3-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=C2)=C1 ZTEZLFTXZTWVRA-UHFFFAOYSA-N 0.000 claims description 3
- KQQIMASSHVEHLH-UHFFFAOYSA-N 4-[5-[[1-(3-chlorophenyl)triazol-4-yl]methoxy]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(N2N=NC(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)=C2)=C1 KQQIMASSHVEHLH-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 18
- 238000002360 preparation method Methods 0.000 abstract description 17
- 230000000926 neurological effect Effects 0.000 abstract description 6
- 230000002496 gastric effect Effects 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 89
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 238000005481 NMR spectroscopy Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 125000005843 halogen group Chemical group 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
- 150000002431 hydrogen Chemical class 0.000 description 20
- 125000004093 cyano group Chemical group *C#N 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000012267 brine Substances 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 210000000111 lower esophageal sphincter Anatomy 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000556 agonist Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 102000018899 Glutamate Receptors Human genes 0.000 description 11
- 108010027915 Glutamate Receptors Proteins 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 10
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 10
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 229930195712 glutamate Natural products 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 9
- 239000007995 HEPES buffer Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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- 230000006870 function Effects 0.000 description 7
- MTVWFVDWRVYDOR-UHFFFAOYSA-N 3,4-Dihydroxyphenylglycol Chemical compound OCC(O)C1=CC=C(O)C(O)=C1 MTVWFVDWRVYDOR-UHFFFAOYSA-N 0.000 description 6
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
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- 230000001052 transient effect Effects 0.000 description 5
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- WYLYCKVEMTYWML-UHFFFAOYSA-N 4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)pyridine Chemical compound N1=C(S(C)(=O)=O)N(C)C(C=2C=CN=CC=2)=N1 WYLYCKVEMTYWML-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/12—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54528904P | 2004-02-18 | 2004-02-18 | |
| USUS60/545,289 | 2004-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070027503A true KR20070027503A (ko) | 2007-03-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067015941A Withdrawn KR20070027503A (ko) | 2004-02-18 | 2005-02-17 | 트리아졸 화합물 및 대사성 글루타메이트 수용체길항제로서 이들의 용도 |
Country Status (17)
| Country | Link |
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| US (2) | US20070185178A1 (https=) |
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| ZA (1) | ZA200606313B (https=) |
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| 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 |
| TW200811156A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators IV |
| PE20090875A1 (es) * | 2007-10-19 | 2009-08-08 | Astrazeneca Ab | Derivados de tetrazol como moduladores de los receptores de glutamato metabotropicos |
| WO2009054785A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole ether derivatives as modulators of mglur5 |
| EP2212316A4 (en) * | 2007-10-26 | 2012-06-27 | Astrazeneca Ab | DERIVATIVES OF AMINO1,2,4-TRIAZOLES AS MODULATORS OF MGLUR5 |
| WO2009054790A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | Amide linked heteroaromatic derivatives as modulators of mglur5 |
| CN101643451B (zh) * | 2008-08-07 | 2013-03-06 | 浙江海正药业股份有限公司 | 过氧化物酶增殖物激活受体亚型δ类激动剂化合物及其制备方法 |
| US20100114146A1 (en) * | 2008-10-30 | 2010-05-06 | Albrecht Thomas E | Methods and devices for predicting intra-gastric satiety and satiation creation device system performance |
| 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. |
| 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 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| KR20130100348A (ko) * | 2010-11-09 | 2013-09-10 | 에프. 호프만-라 로슈 아게 | Gaba 수용체에 대한 리간드로서의 트라이아졸 유도체 |
| WO2013134562A1 (en) | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| AU2013363398B2 (en) | 2012-12-20 | 2017-06-01 | Tempest Therapeutics, Inc. | Triazolone compounds and uses thereof |
| US9776976B2 (en) | 2013-09-06 | 2017-10-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| CN105636945B (zh) | 2013-10-14 | 2017-11-17 | 卫材R&D管理有限公司 | 选择性取代的喹啉化合物 |
| JP6223563B2 (ja) | 2013-10-14 | 2017-11-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
| ES2791252T3 (es) | 2014-08-15 | 2020-11-03 | Janssen Pharmaceuticals Inc | Pirazoles |
| WO2016025917A1 (en) | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Triazoles as nr2b receptor inhibitors |
| HRP20200410T1 (hr) | 2015-07-09 | 2020-08-21 | Janssen Pharmaceutica Nv | Supstituirani 4-azaindoli i njihova upotreba kao modulatora glun2b receptora |
| BR112018016329A2 (pt) | 2016-02-10 | 2018-12-18 | Janssen Pharmaceutica Nv | 1,2,3-triazóis substituídos como moduladores de nmda seletivos para nr2b |
| AR108838A1 (es) | 2016-06-21 | 2018-10-03 | Bristol Myers Squibb Co | Ácidos de carbamoiloximetil triazol ciclohexilo como antagonistas de lpa |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之1H-咪唑並[4,5-b]吡啶-2(3H)-酮及其作為GLUN2B受體調節劑之用途 |
| BR112020003725A2 (pt) | 2017-10-06 | 2020-11-03 | Forma Therapeutics, Inc. | inibição da peptidase 30 específica de ubiquitina |
| WO2019193516A2 (en) | 2018-04-04 | 2019-10-10 | Janssen Pharmaceutica Nv | Substituted pyridine and pyrimidines and their use as glun2b receptor modulators |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス,インコーポレイテッド | ユビキチン特異的ペプチダーゼ30(usp30)阻害剤として有用な縮合二環化合物 |
| LT3860989T (lt) | 2018-10-05 | 2023-06-12 | Forma Therapeutics, Inc. | Sulieti pirolinai, kurie veikia kaip ubikvitinui specifinės proteazės 30 (ups30) inhibitoriai |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN113950357A (zh) | 2019-06-14 | 2022-01-18 | 詹森药业有限公司 | 吡嗪氨基甲酸酯及其作为GluN2B受体调节剂的用途 |
| SG11202112405VA (en) | 2019-06-14 | 2021-12-30 | Janssen Pharmaceutica Nv | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
| KR20220024403A (ko) | 2019-06-14 | 2022-03-03 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로-피라진 및 이들의 glun2b 수용체 조절제로서의 용도 |
| AU2020293642A1 (en) | 2019-06-14 | 2022-01-20 | Janssen Pharmaceutica Nv | Substituted pyrazolo[4,3-b]pyridines and their use as GluN2B receptor modulators |
| CN113993868A (zh) | 2019-06-14 | 2022-01-28 | 詹森药业有限公司 | 取代的吡唑并吡啶酰胺以及它们作为glun2b受体调节剂的用途 |
| MX2021015508A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Carbamatos de piridina y su uso como moduladores del receptor glun2b. |
| JP7667097B2 (ja) | 2019-06-14 | 2025-04-22 | ヤンセン ファーマシューティカ エヌ.ベー. | 置換ピラゾロ-ピリジンアミド及びglun2b受容体調節因子としてのその使用 |
| CN110669017B (zh) * | 2019-10-11 | 2023-08-04 | 成都麻沸散医药科技有限公司 | 多取代三唑甲酸酯类衍生物及其用途 |
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| DE60226756D1 (de) * | 2001-10-04 | 2008-07-03 | Merck & Co Inc | Heteroarylsubstituierte tetrazolmodulatoren des metabotropischen glutamatrezeptors-5 |
| AU2002363250A1 (en) * | 2001-11-01 | 2003-05-12 | Icagen, Inc. | Pyrazole-amides and-sulfonamides |
| DE60334781D1 (de) * | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Di-aryl-substituierte tetrazol-modulatoren des metabotropen glutamat-rezeptors-5 |
| IL166510A0 (en) * | 2002-08-09 | 2006-01-15 | Nps Pharma Inc | 1,2,4"oxadiazole as modulators of metabotropic glutamate receptor-5 |
| AU2003264018A1 (en) * | 2002-08-09 | 2004-02-25 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
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2005
- 2005-02-17 EP EP05723281A patent/EP1720860A1/en not_active Withdrawn
- 2005-02-17 US US10/588,751 patent/US20070185178A1/en not_active Abandoned
- 2005-02-17 AR ARP050100570A patent/AR047744A1/es not_active Application Discontinuation
- 2005-02-17 AU AU2005214375A patent/AU2005214375A1/en not_active Abandoned
- 2005-02-17 KR KR1020067015941A patent/KR20070027503A/ko not_active Withdrawn
- 2005-02-17 TW TW094104645A patent/TW200604183A/zh unknown
- 2005-02-17 BR BRPI0507501-7A patent/BRPI0507501A/pt not_active IP Right Cessation
- 2005-02-17 JP JP2006554231A patent/JP2007523178A/ja active Pending
- 2005-02-17 WO PCT/US2005/005200 patent/WO2005080379A1/en not_active Ceased
- 2005-02-17 CA CA002554894A patent/CA2554894A1/en not_active Abandoned
- 2005-02-17 EA EA200601266A patent/EA200601266A1/ru unknown
- 2005-02-17 RU RU2006127575/04A patent/RU2006127575A/ru not_active Application Discontinuation
- 2005-02-17 CN CNA2005800102818A patent/CN101018779A/zh active Pending
- 2005-02-18 UY UY28760A patent/UY28760A1/es unknown
- 2005-02-18 US US11/060,366 patent/US20060019997A1/en not_active Abandoned
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2006
- 2006-07-25 IL IL177057A patent/IL177057A0/en unknown
- 2006-07-28 NO NO20063468A patent/NO20063468L/no not_active Application Discontinuation
- 2006-07-28 ZA ZA200606313A patent/ZA200606313B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006127575A (ru) | 2008-03-27 |
| BRPI0507501A (pt) | 2007-06-26 |
| CA2554894A1 (en) | 2005-09-01 |
| UY28760A1 (es) | 2005-06-30 |
| CN101018779A (zh) | 2007-08-15 |
| TW200604183A (en) | 2006-02-01 |
| WO2005080379A1 (en) | 2005-09-01 |
| JP2007523178A (ja) | 2007-08-16 |
| NO20063468L (no) | 2006-11-15 |
| US20070185178A1 (en) | 2007-08-09 |
| AR047744A1 (es) | 2006-02-15 |
| EP1720860A1 (en) | 2006-11-15 |
| AU2005214375A1 (en) | 2005-09-01 |
| ZA200606313B (en) | 2007-03-28 |
| EA200601266A1 (ru) | 2007-02-27 |
| IL177057A0 (en) | 2006-12-10 |
| US20060019997A1 (en) | 2006-01-26 |
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