JP2010505809A5 - - Google Patents
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- JP2010505809A5 JP2010505809A5 JP2009530956A JP2009530956A JP2010505809A5 JP 2010505809 A5 JP2010505809 A5 JP 2010505809A5 JP 2009530956 A JP2009530956 A JP 2009530956A JP 2009530956 A JP2009530956 A JP 2009530956A JP 2010505809 A5 JP2010505809 A5 JP 2010505809A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triazol
- ethoxy
- isoxazol
- compound according
- 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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- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 230000003287 optical effect Effects 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 2
- QWWDUYBNUCKRGC-UHFFFAOYSA-N 4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)-2-phenylmethoxypyridine Chemical compound N1=C(S(C)(=O)=O)N(C)C(C=2C=C(OCC=3C=CC=CC=3)N=CC=2)=N1 QWWDUYBNUCKRGC-UHFFFAOYSA-N 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- NQBOKVREWGZKJU-MRVPVSSYSA-N (1r)-1-[2-(3-methylphenyl)tetrazol-5-yl]ethanol Chemical compound N1=C([C@H](O)C)N=NN1C1=CC=CC(C)=C1 NQBOKVREWGZKJU-MRVPVSSYSA-N 0.000 claims 1
- MOXKXNZAWFECME-SECBINFHSA-N (1r)-1-[5-(3-methylphenyl)-1,2-oxazol-3-yl]ethanol Chemical compound O1N=C([C@H](O)C)C=C1C1=CC=CC(C)=C1 MOXKXNZAWFECME-SECBINFHSA-N 0.000 claims 1
- -1 (5- {1- [2- (3-chloro-phenyl) -2H-tetrazol-5-yl] -ethoxy} -4-methyl-4H- [1,2,4] triazol-3-yl) -2- (2-trimethylsilanyl-ethoxymethyl) -2H-pyridazin-3-one Chemical compound 0.000 claims 1
- BGBUSNJDAHNJOH-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)tetrazol-5-yl]ethanone Chemical compound N1=C(C(=O)C)N=NN1C1=CC=CC(Cl)=C1 BGBUSNJDAHNJOH-UHFFFAOYSA-N 0.000 claims 1
- MOXKXNZAWFECME-UHFFFAOYSA-N 1-[5-(3-methylphenyl)-1,2-oxazol-3-yl]ethanol Chemical compound O1N=C(C(O)C)C=C1C1=CC=CC(C)=C1 MOXKXNZAWFECME-UHFFFAOYSA-N 0.000 claims 1
- XOXMZXVWQRVRSA-UHFFFAOYSA-N 1-methyl-4-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyridin-2-one Chemical compound CN1C(SC)=NN=C1C1=CC(=O)N(C)C=C1 XOXMZXVWQRVRSA-UHFFFAOYSA-N 0.000 claims 1
- FCVJZDCOFMWIKT-UHFFFAOYSA-N 1-methyl-4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)pyridin-2-one Chemical compound N1=C(S(C)(=O)=O)N(C)C(C2=CC(=O)N(C)C=C2)=N1 FCVJZDCOFMWIKT-UHFFFAOYSA-N 0.000 claims 1
- KNJWIPWDADOGSM-UHFFFAOYSA-N 1-methyl-4-(4-methyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)pyridin-2-one Chemical compound CN1C(S)=NN=C1C1=CC(=O)N(C)C=C1 KNJWIPWDADOGSM-UHFFFAOYSA-N 0.000 claims 1
- JHJGFOZHTWQUDS-UHFFFAOYSA-N 2-methoxy-4-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)pyridine Chemical compound C1=NC(OC)=CC(C=2N(C(SC)=NN=2)C)=C1 JHJGFOZHTWQUDS-UHFFFAOYSA-N 0.000 claims 1
- XAKCXLMMOPJCIS-UHFFFAOYSA-N 2-methoxy-4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)pyridine Chemical compound C1=NC(OC)=CC(C=2N(C(=NN=2)S(C)(=O)=O)C)=C1 XAKCXLMMOPJCIS-UHFFFAOYSA-N 0.000 claims 1
- YIPORKHUENVACK-UHFFFAOYSA-N 2-oxo-1-(2-trimethylsilylethoxymethyl)pyridine-4-carbohydrazide Chemical compound C[Si](C)(C)CCOCN1C=CC(C(=O)NN)=CC1=O YIPORKHUENVACK-UHFFFAOYSA-N 0.000 claims 1
- CEYSPSIHSYJOCT-UHFFFAOYSA-N 3-(2-methoxypyridin-4-yl)-4-methyl-1h-1,2,4-triazole-5-thione Chemical compound C1=NC(OC)=CC(C=2N(C(S)=NN=2)C)=C1 CEYSPSIHSYJOCT-UHFFFAOYSA-N 0.000 claims 1
- XUQSZCBVPRMQRJ-UHFFFAOYSA-N 4-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)-1-(2-trimethylsilylethoxymethyl)pyridin-2-one Chemical compound CN1C(SC)=NN=C1C1=CC(=O)N(COCC[Si](C)(C)C)C=C1 XUQSZCBVPRMQRJ-UHFFFAOYSA-N 0.000 claims 1
- VDGMLENFLKKBGQ-UHFFFAOYSA-N 4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)-1-(2-trimethylsilylethoxymethyl)pyridin-2-one Chemical compound N1=C(S(C)(=O)=O)N(C)C(C2=CC(=O)N(COCC[Si](C)(C)C)C=C2)=N1 VDGMLENFLKKBGQ-UHFFFAOYSA-N 0.000 claims 1
- BMYBHKLAZPHMAP-UHFFFAOYSA-N 4-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)-1h-pyridin-2-one Chemical compound N1=C(S(C)(=O)=O)N(C)C(C2=CC(=O)NC=C2)=N1 BMYBHKLAZPHMAP-UHFFFAOYSA-N 0.000 claims 1
- XJSVMNXUSRGOOH-UHFFFAOYSA-N 4-(4-methyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)-1-(2-trimethylsilylethoxymethyl)pyridin-2-one Chemical compound CN1C(S)=NN=C1C1=CC(=O)N(COCC[Si](C)(C)C)C=C1 XJSVMNXUSRGOOH-UHFFFAOYSA-N 0.000 claims 1
- UBBUIIAEFUPFIG-LLVKDONJSA-N 4-[4-methyl-5-[(1r)-1-[2-(3-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]-1h-pyridazin-6-one Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(C)C=CC=1)C(N1C)=NN=C1C=1C=NNC(=O)C=1 UBBUIIAEFUPFIG-LLVKDONJSA-N 0.000 claims 1
- AKSJTVFPGONAJS-GFCCVEGCSA-N 4-[4-methyl-5-[(1r)-1-[5-(3-methylphenyl)-1,2-oxazol-3-yl]ethoxy]-1,2,4-triazol-3-yl]-1h-pyridazin-6-one Chemical compound O([C@H](C)C1=NOC(=C1)C=1C=C(C)C=CC=1)C(N1C)=NN=C1C=1C=NNC(=O)C=1 AKSJTVFPGONAJS-GFCCVEGCSA-N 0.000 claims 1
- WLAQJSSHXXRCKV-MRXNPFEDSA-N 4-[5-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1-(2-trimethylsilylethoxymethyl)pyridin-2-one Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CN(COCC[Si](C)(C)C)C(=O)C=1 WLAQJSSHXXRCKV-MRXNPFEDSA-N 0.000 claims 1
- UQTVAGCWRJSYCG-SECBINFHSA-N 4-[5-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridazin-6-one Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=NNC(=O)C=1 UQTVAGCWRJSYCG-SECBINFHSA-N 0.000 claims 1
- NKTIPELEHVFXSE-SNVBAGLBSA-N 4-[5-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CNC(=O)C=1 NKTIPELEHVFXSE-SNVBAGLBSA-N 0.000 claims 1
- MOGLHUQBUBAXOY-MRXNPFEDSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1-(2-trimethylsilylethoxymethyl)pyridin-2-one Chemical compound O([C@H](C)C=1N=C(ON=1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CN(COCC[Si](C)(C)C)C(=O)C=1 MOGLHUQBUBAXOY-MRXNPFEDSA-N 0.000 claims 1
- XQYXLIFREHEULU-LLVKDONJSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1-methylpyridin-2-one Chemical compound O([C@H](C)C=1N=C(ON=1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CN(C)C(=O)C=1 XQYXLIFREHEULU-LLVKDONJSA-N 0.000 claims 1
- QKTWXIVEHVZYMX-SECBINFHSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridazin-6-one Chemical compound O([C@H](C)C=1N=C(ON=1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=NNC(=O)C=1 QKTWXIVEHVZYMX-SECBINFHSA-N 0.000 claims 1
- AQPUHGUBCHMZEI-SNVBAGLBSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound O([C@H](C)C=1N=C(ON=1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CNC(=O)C=1 AQPUHGUBCHMZEI-SNVBAGLBSA-N 0.000 claims 1
- TYRVSFQDVZAMBW-GFCCVEGCSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1-methylpyridin-2-one Chemical compound O([C@H](C)C1=NOC(=C1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CN(C)C(=O)C=1 TYRVSFQDVZAMBW-GFCCVEGCSA-N 0.000 claims 1
- IWNKYSQGZHRHNW-SNVBAGLBSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridazin-6-one Chemical compound O([C@H](C)C1=NOC(=C1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=NNC(=O)C=1 IWNKYSQGZHRHNW-SNVBAGLBSA-N 0.000 claims 1
- YGGDHMSWIMDIPD-LLVKDONJSA-N 4-[5-[(1r)-1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound O([C@H](C)C1=NOC(=C1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C=1C=CNC(=O)C=1 YGGDHMSWIMDIPD-LLVKDONJSA-N 0.000 claims 1
- YGGDHMSWIMDIPD-UHFFFAOYSA-N 4-[5-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound C1=C(C=2C=C(Cl)C=CC=2)ON=C1C(C)OC(N1C)=NN=C1C=1C=CNC(=O)C=1 YGGDHMSWIMDIPD-UHFFFAOYSA-N 0.000 claims 1
- UUPRDNMOMBWQCQ-UHFFFAOYSA-N 4-[5-[[5-(3-chlorophenyl)-1,2-oxazol-3-yl]methoxy]-4-methyl-1,2,4-triazol-3-yl]-1h-pyridin-2-one Chemical compound N=1N=C(C2=CC(=O)NC=C2)N(C)C=1OCC(=NO1)C=C1C1=CC=CC(Cl)=C1 UUPRDNMOMBWQCQ-UHFFFAOYSA-N 0.000 claims 1
- WUPDUHQGDYEYAJ-QGZVFWFLSA-N 5-(3-chlorophenyl)-3-[(1r)-1-[[4-methyl-5-(2-phenylmethoxypyridin-4-yl)-1,2,4-triazol-3-yl]oxy]ethyl]-1,2-oxazole Chemical compound O([C@H](C)C1=NOC(=C1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C(C=1)=CC=NC=1OCC1=CC=CC=C1 WUPDUHQGDYEYAJ-QGZVFWFLSA-N 0.000 claims 1
- WUPDUHQGDYEYAJ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[1-[[4-methyl-5-(2-phenylmethoxypyridin-4-yl)-1,2,4-triazol-3-yl]oxy]ethyl]-1,2-oxazole Chemical compound C1=C(C=2C=C(Cl)C=CC=2)ON=C1C(C)OC(N1C)=NN=C1C(C=1)=CC=NC=1OCC1=CC=CC=C1 WUPDUHQGDYEYAJ-UHFFFAOYSA-N 0.000 claims 1
- YKBHRVPYBXPAEG-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[[4-methyl-5-(2-phenylmethoxypyridin-4-yl)-1,2,4-triazol-3-yl]oxymethyl]-1,2-oxazole Chemical compound N=1N=C(C=2C=C(OCC=3C=CC=CC=3)N=CC=2)N(C)C=1OCC(=NO1)C=C1C1=CC=CC(Cl)=C1 YKBHRVPYBXPAEG-UHFFFAOYSA-N 0.000 claims 1
- OPADHMIOKMGTAZ-UHFFFAOYSA-N 5-(3-methylphenyl)-1,2-oxazole-3-carbaldehyde Chemical compound CC1=CC=CC(C=2ON=C(C=O)C=2)=C1 OPADHMIOKMGTAZ-UHFFFAOYSA-N 0.000 claims 1
- CVBHPUUMGPIEAI-UHFFFAOYSA-N 5-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound CN1C(SC)=NN=C1C1=CC(=O)N(COCC[Si](C)(C)C)N=C1 CVBHPUUMGPIEAI-UHFFFAOYSA-N 0.000 claims 1
- KGSBBPYZHOLCIO-UHFFFAOYSA-N 5-(4-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound N1=C(S(C)(=O)=O)N(C)C(C2=CC(=O)N(COCC[Si](C)(C)C)N=C2)=N1 KGSBBPYZHOLCIO-UHFFFAOYSA-N 0.000 claims 1
- FJYMHPBYZFTMPZ-UHFFFAOYSA-N 5-[4-methyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)OC(N1C)=NN=C1C=1C=NN(COCC[Si](C)(C)C)C(=O)C=1 FJYMHPBYZFTMPZ-UHFFFAOYSA-N 0.000 claims 1
- JZCJAGQBCYZIIE-UHFFFAOYSA-N 5-[4-methyl-5-[1-[5-(3-methylphenyl)-1,2-oxazol-3-yl]ethoxy]-1,2,4-triazol-3-yl]-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound C1=C(C=2C=C(C)C=CC=2)ON=C1C(C)OC(N1C)=NN=C1C=1C=NN(COCC[Si](C)(C)C)C(=O)C=1 JZCJAGQBCYZIIE-UHFFFAOYSA-N 0.000 claims 1
- VFPYYCGBLZHPLK-UHFFFAOYSA-N 5-[5-[1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound N=1OC(C=2C=C(Cl)C=CC=2)=NC=1C(C)OC(N1C)=NN=C1C=1C=NN(COCC[Si](C)(C)C)C(=O)C=1 VFPYYCGBLZHPLK-UHFFFAOYSA-N 0.000 claims 1
- WVTNTIHLDRHKFN-UHFFFAOYSA-N 5-[5-[1-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]-2-(2-trimethylsilylethoxymethyl)pyridazin-3-one Chemical compound C1=C(C=2C=C(Cl)C=CC=2)ON=C1C(C)OC(N1C)=NN=C1C=1C=NN(COCC[Si](C)(C)C)C(=O)C=1 WVTNTIHLDRHKFN-UHFFFAOYSA-N 0.000 claims 1
- XQJZSOSJQLTTAB-UHFFFAOYSA-N 6-oxo-1-(2-trimethylsilylethoxymethyl)pyridazine-4-carbohydrazide Chemical compound C[Si](C)(C)CCOCN1N=CC(C(=O)NN)=CC1=O XQJZSOSJQLTTAB-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 102000001708 Protein Isoforms Human genes 0.000 claims 1
- 108010029485 Protein Isoforms Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- QJVBPSHLWUDCBS-UHFFFAOYSA-N ethyl 2-oxo-1-(2-trimethylsilylethoxymethyl)pyridine-4-carboxylate Chemical compound CCOC(=O)C=1C=CN(COCC[Si](C)(C)C)C(=O)C=1 QJVBPSHLWUDCBS-UHFFFAOYSA-N 0.000 claims 1
- WBNLDAGDJAGFGF-UHFFFAOYSA-N ethyl 6-oxo-1-(2-trimethylsilylethoxymethyl)pyridazine-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(COCC[Si](C)(C)C)C(=O)C=1 WBNLDAGDJAGFGF-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 210000000111 lower esophageal sphincter Anatomy 0.000 claims 1
- LTLTWPKMZBCLFK-UHFFFAOYSA-N methyl 5-(3-methylphenyl)-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OC)C=C1C1=CC=CC(C)=C1 LTLTWPKMZBCLFK-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82832506P | 2006-10-05 | 2006-10-05 | |
| PCT/IB2007/002784 WO2008041075A1 (en) | 2006-10-05 | 2007-09-25 | Mglur5 modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010505809A JP2010505809A (ja) | 2010-02-25 |
| JP2010505809A5 true JP2010505809A5 (enExample) | 2010-11-11 |
Family
ID=39032082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009530956A Pending JP2010505809A (ja) | 2006-10-05 | 2007-09-25 | ｍＧｌｕＲ５調節因子 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7772235B2 (enExample) |
| EP (1) | EP2079730A1 (enExample) |
| JP (1) | JP2010505809A (enExample) |
| KR (1) | KR20090060328A (enExample) |
| CN (1) | CN101547916A (enExample) |
| AR (1) | AR062965A1 (enExample) |
| AU (1) | AU2007303889B2 (enExample) |
| BR (1) | BRPI0719155A2 (enExample) |
| CA (1) | CA2665083A1 (enExample) |
| CL (1) | CL2007002757A1 (enExample) |
| CO (1) | CO6220935A2 (enExample) |
| IL (1) | IL197722A0 (enExample) |
| MX (1) | MX2009003227A (enExample) |
| NO (1) | NO20091626L (enExample) |
| NZ (1) | NZ575657A (enExample) |
| PE (1) | PE20081378A1 (enExample) |
| RU (1) | RU2439068C2 (enExample) |
| SA (1) | SA07280518B1 (enExample) |
| TW (1) | TW200821305A (enExample) |
| UY (1) | UY30610A1 (enExample) |
| WO (1) | WO2008041075A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009054790A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | Amide linked heteroaromatic derivatives as modulators of mglur5 |
| TW200922586A (en) * | 2007-10-26 | 2009-06-01 | Astrazeneca Ab | Thiophene 1,2,4-triazole derivatives as modulators of mGluR5 |
| WO2009054786A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole aryl n-oxides derivatives as modulators of mglur5 |
| TW200922585A (en) * | 2007-10-26 | 2009-06-01 | Astrazeneca Ab | Amino 1,2,4-triazole derivatives as modulators of mGluR5 |
| WO2009054785A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole ether derivatives as modulators of mglur5 |
| WO2009054787A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole carboxylic acid derivatives as modulators of mglur5 |
| TW201011016A (en) * | 2008-08-12 | 2010-03-16 | Astrazeneca Ab | New compounds 501 |
| UY32044A (es) * | 2008-08-12 | 2010-03-26 | Astrazeneca Ab | Nueva forma cristalina a de 4-(5-{ (1r)-1-[5-(3-clorofenil)isoxazol-3-il]etoxi} -4-metil-4h-1,2,4-triazol-3-il)piridina |
| SG171755A1 (en) * | 2008-12-18 | 2011-07-28 | Astrazeneca Ab | New process for the preparation of 1- [5- (3-chloro-phenyl) - isooxazol-3-yl] -ethanone and (r) -1- [5- (3-chloro-phenyl) - isooxazol-3-yl] -ethanol |
| US20100273805A1 (en) * | 2009-04-23 | 2010-10-28 | Astrazeneca Ab | Sulphide bridged derivatives as modulators of mglur5 733 |
| IN2012DN03322A (enExample) * | 2009-09-21 | 2015-10-23 | Univ Vanderbilt | |
| WO2012058128A2 (en) * | 2010-10-28 | 2012-05-03 | Merck Sharp & Dohme Corp. | Caprolactam mglur5 receptor modulators |
| EP2648723A4 (en) | 2010-12-08 | 2014-04-02 | Univ Vanderbilt | Bicyclic pyrazole compounds as allergic Mglur5 receptor modulators |
| WO2012083224A1 (en) * | 2010-12-17 | 2012-06-21 | Vanderbilt University | Bicyclic triazole and pyrazole lactams as allosteric modulators of mglur5 receptors |
| US8471027B2 (en) | 2011-04-06 | 2013-06-25 | Hoffmann-La Roche Inc. | Adamantyl compounds |
| EP2857387A1 (en) | 2013-10-07 | 2015-04-08 | Boehringer Ingelheim International Gmbh | Process for manufacturing 1,6-dihydro-6-oxo-4-pyridazine carboxylic acid |
| CN109311823B (zh) * | 2016-07-15 | 2023-01-24 | 泸州东方农化有限公司 | 一种1,2,4-三唑-3-硫酮化合物的合成方法及其中间体 |
| EP3684364A4 (en) | 2017-09-18 | 2021-06-02 | Goldfinch Bio, Inc. | PYRIDAZINONE AND METHOD OF USE THEREOF |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1894241A (zh) * | 2002-08-09 | 2007-01-10 | 阿斯利康(瑞典)有限公司 | 作为代谢型谷氨酸受体－5调节剂的“1,2,4” 噁二唑 |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| GB0514296D0 (en) | 2005-07-12 | 2005-08-17 | Novartis Ag | Organic compounds |
| 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 |
| TW200811157A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators I |
| TW200808800A (en) * | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
-
2007
- 2007-09-21 TW TW096135382A patent/TW200821305A/zh unknown
- 2007-09-24 SA SA07280518A patent/SA07280518B1/ar unknown
- 2007-09-25 CA CA002665083A patent/CA2665083A1/en not_active Abandoned
- 2007-09-25 EP EP07804973A patent/EP2079730A1/en not_active Withdrawn
- 2007-09-25 JP JP2009530956A patent/JP2010505809A/ja active Pending
- 2007-09-25 RU RU2009111113/04A patent/RU2439068C2/ru not_active IP Right Cessation
- 2007-09-25 AU AU2007303889A patent/AU2007303889B2/en not_active Ceased
- 2007-09-25 WO PCT/IB2007/002784 patent/WO2008041075A1/en not_active Ceased
- 2007-09-25 KR KR1020097006875A patent/KR20090060328A/ko not_active Withdrawn
- 2007-09-25 BR BRPI0719155-3A patent/BRPI0719155A2/pt not_active IP Right Cessation
- 2007-09-25 CL CL200702757A patent/CL2007002757A1/es unknown
- 2007-09-25 AR ARP070104214A patent/AR062965A1/es not_active Application Discontinuation
- 2007-09-25 NZ NZ575657A patent/NZ575657A/en not_active IP Right Cessation
- 2007-09-25 PE PE2007001288A patent/PE20081378A1/es not_active Application Discontinuation
- 2007-09-25 MX MX2009003227A patent/MX2009003227A/es not_active Application Discontinuation
- 2007-09-25 UY UY30610A patent/UY30610A1/es not_active Application Discontinuation
- 2007-09-25 US US11/902,784 patent/US7772235B2/en not_active Expired - Fee Related
- 2007-09-25 CN CNA2007800451517A patent/CN101547916A/zh active Pending
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2009
- 2009-03-19 IL IL197722A patent/IL197722A0/en unknown
- 2009-04-23 NO NO20091626A patent/NO20091626L/no not_active Application Discontinuation
- 2009-04-29 CO CO09043380A patent/CO6220935A2/es not_active Application Discontinuation
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