JP2007513957A5 - - Google Patents
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- JP2007513957A5 JP2007513957A5 JP2006543943A JP2006543943A JP2007513957A5 JP 2007513957 A5 JP2007513957 A5 JP 2007513957A5 JP 2006543943 A JP2006543943 A JP 2006543943A JP 2006543943 A JP2006543943 A JP 2006543943A JP 2007513957 A5 JP2007513957 A5 JP 2007513957A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- carbon atoms
- halogen
- unsubstituted
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 241
- 125000004432 carbon atoms Chemical group C* 0.000 claims 153
- 229910052736 halogen Inorganic materials 0.000 claims 137
- 150000002367 halogens Chemical class 0.000 claims 125
- 239000000203 mixture Substances 0.000 claims 119
- 125000003545 alkoxy group Chemical group 0.000 claims 93
- -1 nitro, amino Chemical group 0.000 claims 93
- 125000004093 cyano group Chemical group *C#N 0.000 claims 85
- 150000001875 compounds Chemical class 0.000 claims 65
- 125000003118 aryl group Chemical group 0.000 claims 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 57
- 125000004429 atoms Chemical group 0.000 claims 56
- 125000004043 oxo group Chemical group O=* 0.000 claims 53
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims 40
- 125000000623 heterocyclic group Chemical group 0.000 claims 39
- 125000004663 dialkyl amino group Chemical group 0.000 claims 36
- 239000003814 drug Substances 0.000 claims 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 22
- 239000002253 acid Substances 0.000 claims 21
- 125000002252 acyl group Chemical group 0.000 claims 21
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 21
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 21
- 125000004103 aminoalkyl group Chemical group 0.000 claims 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 21
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 21
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 20
- 125000003282 alkyl amino group Chemical group 0.000 claims 18
- 125000004414 alkyl thio group Chemical group 0.000 claims 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 18
- 125000004434 sulfur atoms Chemical group 0.000 claims 18
- 229920000728 polyester Polymers 0.000 claims 16
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 15
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 15
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000002837 carbocyclic group Chemical group 0.000 claims 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 150000001350 alkyl halides Chemical class 0.000 claims 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 6
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 5
- 206010004938 Bipolar disease Diseases 0.000 claims 5
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims 5
- 206010027175 Memory impairment Diseases 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 4
- 239000002552 dosage form Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000005842 heteroatoms Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000000051 modifying Effects 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 206010004939 Bipolar I disease Diseases 0.000 claims 2
- 206010057668 Cognitive disease Diseases 0.000 claims 2
- 206010013663 Drug dependence Diseases 0.000 claims 2
- 208000008013 Morphine Dependence Diseases 0.000 claims 2
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 2
- 108060002038 Pde4 Proteins 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 230000003001 depressive Effects 0.000 claims 2
- 229940079593 drugs Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- NXBQEAYTHZMYEY-UHFFFAOYSA-N 1-[4-[3-chloro-N-(pyridin-3-ylmethyl)anilino]-2-methoxyphenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=C(Cl)C=CC=2)=C1 NXBQEAYTHZMYEY-UHFFFAOYSA-N 0.000 claims 1
- RQLSTSLODCKLON-UHFFFAOYSA-N 3-[(5,6-dimethoxypyridin-2-yl)-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound N1=C(OC)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 RQLSTSLODCKLON-UHFFFAOYSA-N 0.000 claims 1
- BGUDMIDTEMWLLK-UHFFFAOYSA-N 3-[(5-methoxy-6-propan-2-yloxypyridin-2-yl)-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound N1=C(OC(C)C)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 BGUDMIDTEMWLLK-UHFFFAOYSA-N 0.000 claims 1
- YPPIWSASWMFVEQ-UHFFFAOYSA-N 3-[(6-cyclobutyloxy-5-methoxypyridin-2-yl)-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)N=C1OC1CCC1 YPPIWSASWMFVEQ-UHFFFAOYSA-N 0.000 claims 1
- YSVXVFMIZCUBGD-UHFFFAOYSA-N 3-[(6-cyclopentyloxy-5-methoxypyridin-2-yl)-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)N=C1OC1CCCC1 YSVXVFMIZCUBGD-UHFFFAOYSA-N 0.000 claims 1
- JUMZIXGVPWRRIY-UHFFFAOYSA-N 3-[(6-ethoxy-5-methoxypyridin-2-yl)-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC)C(OCC)=NC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 JUMZIXGVPWRRIY-UHFFFAOYSA-N 0.000 claims 1
- FEMNMPVEZVPTHL-UHFFFAOYSA-N 3-[2-chloro-5-cyclopentyloxy-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(Cl)=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 FEMNMPVEZVPTHL-UHFFFAOYSA-N 0.000 claims 1
- GWGQVKLCJOKTAD-UHFFFAOYSA-N 3-[3-chloro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 GWGQVKLCJOKTAD-UHFFFAOYSA-N 0.000 claims 1
- CAUQLAMLVAUUJC-UHFFFAOYSA-N 3-[3-cyclopentyloxy-2-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound FC1=C(OC2CCCC2)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 CAUQLAMLVAUUJC-UHFFFAOYSA-N 0.000 claims 1
- MZHGDMYCCKURCP-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-fluoro-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(OC3CCCC3)C(F)=CC=2)=C1 MZHGDMYCCKURCP-UHFFFAOYSA-N 0.000 claims 1
- JLNMFQRFPNWZNB-UHFFFAOYSA-N 3-[3-fluoro-4-methoxy-N-(1,3-thiazol-5-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CN=CS1 JLNMFQRFPNWZNB-UHFFFAOYSA-N 0.000 claims 1
- JKFDPQTVCXHURQ-UHFFFAOYSA-N 3-[3-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 JKFDPQTVCXHURQ-UHFFFAOYSA-N 0.000 claims 1
- LVQVCASPCQIYMF-UHFFFAOYSA-N 3-[3-methoxy-4-(methylcarbamoyl)-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(OC)C(C(=O)NC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 LVQVCASPCQIYMF-UHFFFAOYSA-N 0.000 claims 1
- DBGVBGBKKWBIEQ-UHFFFAOYSA-N 3-[4-(difluoromethoxy)-3-fluoro-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(F)C(OC(F)F)=CC=2)=C1 DBGVBGBKKWBIEQ-UHFFFAOYSA-N 0.000 claims 1
- PBNKESVVUJKZJB-UHFFFAOYSA-N 3-[4-(difluoromethoxy)-3-fluoro-N-[(3-fluorophenyl)methyl]anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=C(F)C=CC=2)C=2C=C(F)C(OC(F)F)=CC=2)=C1 PBNKESVVUJKZJB-UHFFFAOYSA-N 0.000 claims 1
- RPIXOTXUFZAADL-UHFFFAOYSA-N 3-[4-(difluoromethoxy)-N-[(2,6-difluorophenyl)methyl]-3-fluoroanilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C(=CC=CC=2F)F)C=2C=C(F)C(OC(F)F)=CC=2)=C1 RPIXOTXUFZAADL-UHFFFAOYSA-N 0.000 claims 1
- FXJCXCYGVSPWBO-UHFFFAOYSA-N 3-[4-acetyl-3-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(C(C)=O)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 FXJCXCYGVSPWBO-UHFFFAOYSA-N 0.000 claims 1
- LHEHEAJRLCIEHJ-UHFFFAOYSA-N 3-[4-carbamoyl-3-methoxy-N-(1,3-thiazol-5-ylmethyl)anilino]benzoic acid Chemical compound C1=C(C(N)=O)C(OC)=CC(N(CC=2SC=NC=2)C=2C=C(C=CC=2)C(O)=O)=C1 LHEHEAJRLCIEHJ-UHFFFAOYSA-N 0.000 claims 1
- WWHQYFPECLPSRQ-UHFFFAOYSA-N 3-[4-carbamoyl-3-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(C(N)=O)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 WWHQYFPECLPSRQ-UHFFFAOYSA-N 0.000 claims 1
- FALSLHSRECAJMW-HXUWFJFHSA-N 3-[4-fluoro-3-[(3R)-oxolan-3-yl]oxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(O[C@H]3COCC3)C(F)=CC=2)=C1 FALSLHSRECAJMW-HXUWFJFHSA-N 0.000 claims 1
- BEHGKDOWFGASIV-UHFFFAOYSA-N 3-[4-fluoro-3-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 BEHGKDOWFGASIV-UHFFFAOYSA-N 0.000 claims 1
- HUOAPYQGLYYHTJ-UHFFFAOYSA-N 3-[4-fluoro-3-methoxy-N-(pyridin-4-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N(CC=2C=CN=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 HUOAPYQGLYYHTJ-UHFFFAOYSA-N 0.000 claims 1
- TYLUVBOLKKYDSV-UHFFFAOYSA-N 3-[4-fluoro-N-[(3-fluorophenyl)methyl]-3-methoxyanilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N(CC=2C=C(F)C=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 TYLUVBOLKKYDSV-UHFFFAOYSA-N 0.000 claims 1
- YHPWNNYPGCXHOQ-UHFFFAOYSA-N 3-[4-methoxy-3-(2-methylpropanoylamino)-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(NC(=O)C(C)C)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 YHPWNNYPGCXHOQ-UHFFFAOYSA-N 0.000 claims 1
- SKFMTQVYEVFYJJ-UHFFFAOYSA-N 3-[5-cyclopentyloxy-2-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(F)=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 SKFMTQVYEVFYJJ-UHFFFAOYSA-N 0.000 claims 1
- BBNRMVKLYYCPIH-UHFFFAOYSA-N 3-[5-cyclopentyloxy-4-methoxy-2-methyl-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(C)=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 BBNRMVKLYYCPIH-UHFFFAOYSA-N 0.000 claims 1
- MPHFNEPPLQTNGG-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-6-methoxypyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OC)=NC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 MPHFNEPPLQTNGG-UHFFFAOYSA-N 0.000 claims 1
- IDEGXQCKZIRIJK-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-6-propan-2-yloxypyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound C1=C(OC(F)F)C(OC(C)C)=NC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 IDEGXQCKZIRIJK-UHFFFAOYSA-N 0.000 claims 1
- YGGVXBZNRGCPMC-UHFFFAOYSA-N 3-[[5-methoxy-6-(oxolan-3-yloxy)pyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)N=C1OC1CCOC1 YGGVXBZNRGCPMC-UHFFFAOYSA-N 0.000 claims 1
- KCVDLERXCCNFGS-UHFFFAOYSA-N 3-[[6-(cyclopropylmethoxy)-5-(difluoromethoxy)pyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2N=C(OCC3CC3)C(OC(F)F)=CC=2)=C1 KCVDLERXCCNFGS-UHFFFAOYSA-N 0.000 claims 1
- JJIWXOGQHLUECA-UHFFFAOYSA-N 3-[[6-(cyclopropylmethoxy)-5-methoxypyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)N=C1OCC1CC1 JJIWXOGQHLUECA-UHFFFAOYSA-N 0.000 claims 1
- GCEWXNZDKWVNFP-UHFFFAOYSA-N 3-[[6-cyclobutyloxy-5-(difluoromethoxy)pyridin-2-yl]-(pyridin-3-ylmethyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2N=C(OC3CCC3)C(OC(F)F)=CC=2)=C1 GCEWXNZDKWVNFP-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- ALHGZDYTBIPHKL-UHFFFAOYSA-N 4-[2-chloro-5-cyclopentyloxy-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(Cl)=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 ALHGZDYTBIPHKL-UHFFFAOYSA-N 0.000 claims 1
- SZNLJCFSYGMMHC-UHFFFAOYSA-N 4-[3-chloro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1N(C=1C=CC(=CC=1)C(O)=O)CC1=CC=CN=C1 SZNLJCFSYGMMHC-UHFFFAOYSA-N 0.000 claims 1
- DFZZSFRZECTRSI-UHFFFAOYSA-N 4-[3-chloro-N-(pyridin-3-ylmethyl)anilino]-2-methoxybenzamide Chemical compound C1=C(C(N)=O)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=C(Cl)C=CC=2)=C1 DFZZSFRZECTRSI-UHFFFAOYSA-N 0.000 claims 1
- HNBPLKDMHLNVJW-UHFFFAOYSA-N 4-[3-cyclopentyloxy-2-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound FC1=C(OC2CCCC2)C(OC)=CC=C1N(C=1C=CC(=CC=1)C(O)=O)CC1=CC=CN=C1 HNBPLKDMHLNVJW-UHFFFAOYSA-N 0.000 claims 1
- AEYFNERLHOIBNC-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-fluoro-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(C=1C=C(OC2CCCC2)C(F)=CC=1)CC1=CC=CN=C1 AEYFNERLHOIBNC-UHFFFAOYSA-N 0.000 claims 1
- FRCWRJFMQNJJLT-UHFFFAOYSA-N 4-[3-fluoro-4-methoxy-N-(1,3-thiazol-5-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C=1C=CC(=CC=1)C(O)=O)CC1=CN=CS1 FRCWRJFMQNJJLT-UHFFFAOYSA-N 0.000 claims 1
- GHNKXMBCSCAUQF-UHFFFAOYSA-N 4-[3-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C=1C=CC(=CC=1)C(O)=O)CC1=CC=CN=C1 GHNKXMBCSCAUQF-UHFFFAOYSA-N 0.000 claims 1
- QCNOETVBHRINAV-UHFFFAOYSA-N 4-[4-carbamoyl-3-methoxy-N-(1,3-thiazol-5-ylmethyl)anilino]benzoic acid Chemical compound C1=C(C(N)=O)C(OC)=CC(N(CC=2SC=NC=2)C=2C=CC(=CC=2)C(O)=O)=C1 QCNOETVBHRINAV-UHFFFAOYSA-N 0.000 claims 1
- AWSUIISGAUYEBS-HXUWFJFHSA-N 4-[4-fluoro-3-[(3R)-oxolan-3-yl]oxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(C=1C=C(O[C@H]2COCC2)C(F)=CC=1)CC1=CC=CN=C1 AWSUIISGAUYEBS-HXUWFJFHSA-N 0.000 claims 1
- WWITYXKKSYSJQI-UHFFFAOYSA-N 4-[4-fluoro-3-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)=C1 WWITYXKKSYSJQI-UHFFFAOYSA-N 0.000 claims 1
- RKUYOECQQVZADQ-UHFFFAOYSA-N 4-[5-cyclopentyloxy-2-fluoro-4-methoxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(F)=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 RKUYOECQQVZADQ-UHFFFAOYSA-N 0.000 claims 1
- HCEYGTUCTGWBKW-UHFFFAOYSA-N 4-[5-cyclopentyloxy-4-methoxy-2-methyl-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC(C)=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 HCEYGTUCTGWBKW-UHFFFAOYSA-N 0.000 claims 1
- NOWQWIVYTDTQMY-UHFFFAOYSA-N 5-[3-chloro-N-(pyridin-3-ylmethyl)anilino]-2-methoxybenzamide Chemical compound C1=C(C(N)=O)C(OC)=CC=C1N(C=1C=C(Cl)C=CC=1)CC1=CC=CN=C1 NOWQWIVYTDTQMY-UHFFFAOYSA-N 0.000 claims 1
- QFGMCTRUGUQECK-UHFFFAOYSA-N 5-chloro-N-(3-chlorophenyl)-4,6-difluoro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CN(C=1N=C(F)C(Cl)=C(F)N=1)C1=CC=CC(Cl)=C1 QFGMCTRUGUQECK-UHFFFAOYSA-N 0.000 claims 1
- NEZSKDDWJPDPDA-UHFFFAOYSA-N 5-cyclopentyloxy-2-fluoro-4-methoxy-N-phenyl-N-(pyridin-3-ylmethyl)aniline Chemical compound COC1=CC(F)=C(N(CC=2C=NC=CC=2)C=2C=CC=CC=2)C=C1OC1CCCC1 NEZSKDDWJPDPDA-UHFFFAOYSA-N 0.000 claims 1
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| KR20120062863A (ko) | 2003-07-30 | 2012-06-14 | 리겔 파마슈티칼스, 인크. | 자가면역 질환의 치료 또는 예방에 사용하기 위한 2,4-피리미딘디아민 화합물 |
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| ES2195419T3 (es) * | 1997-11-25 | 2003-12-01 | Warner Lambert Co | Inhibidores bencenosulfonamida de pde-iv y su uso terapeutico. |
| CA2364653A1 (en) * | 1999-02-25 | 2000-08-31 | Merck Frosst Canada & Co. | Pde iv inhibiting compounds, compositions and methods of treatment |
| US6180650B1 (en) * | 1999-04-23 | 2001-01-30 | Merck Frosst Canada & Co. | Heterosubstituted pyridine derivatives as PDE 4 inhibitors |
| US6200993B1 (en) * | 1999-05-05 | 2001-03-13 | Merck Frosst Canada & Co. | Heterosubstituted pyridine derivatives as PDE4 inhibitors |
| AU5020400A (en) * | 1999-05-20 | 2000-12-12 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
| US6699890B2 (en) * | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| AU2002303078B2 (en) | 2001-01-22 | 2007-08-30 | Memory Pharmaceuticals Corporation | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
| FR2827288B1 (fr) * | 2001-07-12 | 2003-10-31 | Servier Lab | Nouveaux derives d'octahydro-2h-pyrido[1,2-a]pyrazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20030149052A1 (en) * | 2002-01-22 | 2003-08-07 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| EP1500643A4 (en) * | 2002-04-03 | 2007-03-28 | Dainippon Sumitomo Pharma Co | BENZAMIDE DERIVATIVES |
| WO2004009552A1 (en) * | 2002-07-19 | 2004-01-29 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including n-substituted aniline and diphenylamine analogs |
| US7087625B2 (en) * | 2002-11-19 | 2006-08-08 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
-
2004
- 2004-12-08 MY MYPI20045068A patent/MY141255A/en unknown
- 2004-12-09 AR ARP040104598A patent/AR046789A1/es not_active Application Discontinuation
- 2004-12-10 MX MXPA06006557A patent/MXPA06006557A/es unknown
- 2004-12-10 AT AT04813392T patent/ATE478049T1/de not_active IP Right Cessation
- 2004-12-10 WO PCT/US2004/041068 patent/WO2005061458A2/en active Application Filing
- 2004-12-10 US US11/008,775 patent/US20050222207A1/en not_active Abandoned
- 2004-12-10 AU AU2004303855A patent/AU2004303855A1/en not_active Abandoned
- 2004-12-10 KR KR1020067013876A patent/KR20060128909A/ko not_active Application Discontinuation
- 2004-12-10 DE DE602004028754T patent/DE602004028754D1/de active Active
- 2004-12-10 RU RU2006124518/04A patent/RU2388750C2/ru not_active IP Right Cessation
- 2004-12-10 CA CA002548824A patent/CA2548824A1/en not_active Abandoned
- 2004-12-10 JP JP2006543943A patent/JP2007513957A/ja active Pending
- 2004-12-10 EP EP04813392A patent/EP1692109B1/en active Active
- 2004-12-10 BR BRPI0417110-1A patent/BRPI0417110A/pt not_active IP Right Cessation
- 2004-12-10 TW TW093138511A patent/TW200602322A/zh unknown
- 2004-12-10 CN CNA2004800412769A patent/CN1922144A/zh active Pending
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