JP2006504656A5 - - Google Patents
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- JP2006504656A5 JP2006504656A5 JP2004523585A JP2004523585A JP2006504656A5 JP 2006504656 A5 JP2006504656 A5 JP 2006504656A5 JP 2004523585 A JP2004523585 A JP 2004523585A JP 2004523585 A JP2004523585 A JP 2004523585A JP 2006504656 A5 JP2006504656 A5 JP 2006504656A5
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- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- alkoxy
- halogen
- 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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- 125000004432 carbon atom Chemical group C* 0.000 claims 1521
- 125000000217 alkyl group Chemical group 0.000 claims 762
- 229910052736 halogen Inorganic materials 0.000 claims 376
- 150000002367 halogens Chemical class 0.000 claims 369
- -1 cyano, hydroxy Chemical group 0.000 claims 279
- 125000004093 cyano group Chemical group *C#N 0.000 claims 274
- 125000003545 alkoxy group Chemical group 0.000 claims 248
- 125000004043 oxo group Chemical group O=* 0.000 claims 187
- 125000003118 aryl group Chemical group 0.000 claims 176
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 166
- 125000006413 ring segment Chemical group 0.000 claims 138
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 136
- 229920006395 saturated elastomer Polymers 0.000 claims 102
- 125000004663 dialkyl amino group Chemical group 0.000 claims 97
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 82
- 229910052799 carbon Inorganic materials 0.000 claims 66
- 150000001721 carbon Chemical group 0.000 claims 64
- 125000000623 heterocyclic group Chemical group 0.000 claims 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 61
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 60
- 125000003282 alkyl amino group Chemical group 0.000 claims 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims 59
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 58
- 229910052760 oxygen Inorganic materials 0.000 claims 58
- 125000004430 oxygen atom Chemical group O* 0.000 claims 58
- 125000004434 sulfur atom Chemical group 0.000 claims 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 56
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 55
- 239000002253 acid Substances 0.000 claims 55
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 55
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 55
- 125000004103 aminoalkyl group Chemical group 0.000 claims 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 55
- 125000004414 alkyl thio group Chemical group 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 53
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 53
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 52
- 125000003710 aryl alkyl group Chemical group 0.000 claims 48
- 125000002837 carbocyclic group Chemical group 0.000 claims 47
- 125000001072 heteroaryl group Chemical group 0.000 claims 47
- 125000003435 aroyl group Chemical group 0.000 claims 46
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 46
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 46
- 125000001589 carboacyl group Chemical group 0.000 claims 45
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 43
- 239000003814 drug Substances 0.000 claims 38
- 238000004519 manufacturing process Methods 0.000 claims 37
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 35
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 24
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 23
- 125000005842 heteroatom Chemical group 0.000 claims 22
- 125000004429 atom Chemical group 0.000 claims 20
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 208000010877 cognitive disease Diseases 0.000 claims 14
- 230000001149 cognitive effect Effects 0.000 claims 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims 11
- 206010027175 memory impairment Diseases 0.000 claims 9
- 208000028698 Cognitive impairment Diseases 0.000 claims 7
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 7
- 102000004190 Enzymes Human genes 0.000 claims 7
- 108090000790 Enzymes Proteins 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 206010020751 Hypersensitivity Diseases 0.000 claims 7
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 7
- 230000007815 allergy Effects 0.000 claims 7
- 230000007423 decrease Effects 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 7
- 230000002708 enhancing effect Effects 0.000 claims 7
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 208000027866 inflammatory disease Diseases 0.000 claims 7
- 230000002401 inhibitory effect Effects 0.000 claims 7
- 239000003937 drug carrier Substances 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 208000026935 allergic disease Diseases 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- ZIZIJHBSNITYBE-UHFFFAOYSA-N 3-[3-hydroxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(O)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 ZIZIJHBSNITYBE-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 2
- IKYOLUBQNJKMBC-UHFFFAOYSA-N 2-acetamido-5-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C(NC(C)=O)=CC=2)C(O)=O)C=C1OC1CCCC1 IKYOLUBQNJKMBC-UHFFFAOYSA-N 0.000 claims 1
- JFPNKPINPVNQKD-UHFFFAOYSA-N 2-amino-5-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C(N)=CC=2)C(O)=O)C=C1OC1CCCC1 JFPNKPINPVNQKD-UHFFFAOYSA-N 0.000 claims 1
- GVESADABUIVATI-UHFFFAOYSA-N 2-chloro-4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(Cl)C(C(O)=O)=CC=2)C=C1OC1CCCC1 GVESADABUIVATI-UHFFFAOYSA-N 0.000 claims 1
- ONQYIIVOAHLMJC-OZAIVSQSSA-N 2-chloro-5-[2-[(3R)-4-methoxyoxolan-3-yl]oxy-N-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1[C@@H](COC1)OC1=C(N(CC=2C=NC=CC=2)C2=CC(=C(C=C2)Cl)C(=O)O)C=CC=C1 ONQYIIVOAHLMJC-OZAIVSQSSA-N 0.000 claims 1
- JBOHJDIOSKJSEP-UHFFFAOYSA-N 2-chloro-5-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C(Cl)=CC=2)C(O)=O)C=C1OC1CCCC1 JBOHJDIOSKJSEP-UHFFFAOYSA-N 0.000 claims 1
- WWYNKQTWLCQREJ-OZAIVSQSSA-N 3-[2-[(3R)-4-methoxyoxolan-3-yl]oxy-N-(pyridin-4-ylmethyl)anilino]benzoic acid Chemical compound COC1[C@@H](COC1)OC1=C(N(CC2=CC=NC=C2)C2=CC(=CC=C2)C(=O)O)C=CC=C1 WWYNKQTWLCQREJ-OZAIVSQSSA-N 0.000 claims 1
- ZZPYGPLGVWYGQN-UHFFFAOYSA-N 3-[3,4-bis(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC(N(CC=2C=NC=CC=2)C=2C=C(OC(F)F)C(OC(F)F)=CC=2)=C1 ZZPYGPLGVWYGQN-UHFFFAOYSA-N 0.000 claims 1
- JOHMSZBFSOCBHW-UHFFFAOYSA-N 3-[3-(2-cyclopropylethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OCCC1CC1 JOHMSZBFSOCBHW-UHFFFAOYSA-N 0.000 claims 1
- YQMXJQLDUFDCSG-UHFFFAOYSA-N 3-[3-(cyclobutylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OCC1CCC1 YQMXJQLDUFDCSG-UHFFFAOYSA-N 0.000 claims 1
- BPAMXLJNRKSMEZ-UHFFFAOYSA-N 3-[3-cyclobutyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCC1 BPAMXLJNRKSMEZ-UHFFFAOYSA-N 0.000 claims 1
- PVIZKCDYYHQHFS-UHFFFAOYSA-N 3-[3-cycloheptyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCCCC1 PVIZKCDYYHQHFS-UHFFFAOYSA-N 0.000 claims 1
- FKBXEXYECLAJEG-UHFFFAOYSA-N 3-[3-cyclohexyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCCC1 FKBXEXYECLAJEG-UHFFFAOYSA-N 0.000 claims 1
- ZQVJRONONNYCSU-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC(N(CC=2C=NC=CC=2)C=2C=C(OC3CCCC3)C(OC(F)F)=CC=2)=C1 ZQVJRONONNYCSU-UHFFFAOYSA-N 0.000 claims 1
- OIOJVANAGFBYFG-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-5-fluorobenzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=C(F)C=2)C(O)=O)C=C1OC1CCCC1 OIOJVANAGFBYFG-UHFFFAOYSA-N 0.000 claims 1
- FLLCGZGQBUPYCA-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-(2-hydroxyethyl)benzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(=O)NCCO)C=C1OC1CCCC1 FLLCGZGQBUPYCA-UHFFFAOYSA-N 0.000 claims 1
- CDUIOUDOCKFVCV-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-(2-methylphenyl)sulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)C=C1OC1CCCC1 CDUIOUDOCKFVCV-UHFFFAOYSA-N 0.000 claims 1
- GFAOXAVMWZPBOM-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 GFAOXAVMWZPBOM-UHFFFAOYSA-N 0.000 claims 1
- LBKFHDGISJQJFO-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-methylsulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(=O)NS(C)(=O)=O)C=C1OC1CCCC1 LBKFHDGISJQJFO-UHFFFAOYSA-N 0.000 claims 1
- WUPPXHSCTGNONT-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(N)=O)C=C1OC1CCCC1 WUPPXHSCTGNONT-UHFFFAOYSA-N 0.000 claims 1
- YJKRSUSXIRYJEJ-UHFFFAOYSA-N 3-[3-cyclopentyloxy-n-[(2,6-difluorophenyl)methyl]-4-methoxyanilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C(=CC=CC=2F)F)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 YJKRSUSXIRYJEJ-UHFFFAOYSA-N 0.000 claims 1
- WOJYWTBANNNKLV-UHFFFAOYSA-N 3-[3-cyclopentyloxy-n-[(5-fluoropyridin-3-yl)methyl]-4-methoxyanilino]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=C(F)C=NC=2)C=2C=C(C=CC=2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)C=C1OC1CCCC1 WOJYWTBANNNKLV-UHFFFAOYSA-N 0.000 claims 1
- GHVNTTDGOXVIHP-UHFFFAOYSA-N 3-[3-cyclopentyloxy-n-[(5-fluoropyridin-3-yl)methyl]-4-methoxyanilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=C(F)C=NC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 GHVNTTDGOXVIHP-UHFFFAOYSA-N 0.000 claims 1
- RVSHDISGIWENMA-UHFFFAOYSA-N 3-[4-methoxy-3-(2h-pyran-4-yloxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1=CCOC=C1 RVSHDISGIWENMA-UHFFFAOYSA-N 0.000 claims 1
- FEMNPQLRKFWLAW-UHFFFAOYSA-N 3-amino-5-[(1,3-dimethylpyrazol-4-yl)methyl]benzoic acid Chemical compound CC1=NN(C)C=C1CC1=CC(N)=CC(C(O)=O)=C1 FEMNPQLRKFWLAW-UHFFFAOYSA-N 0.000 claims 1
- GBOMDBPTDBFTII-UHFFFAOYSA-N 3-cyclopentyloxy-4-methoxy-n-(3-morpholin-4-ylsulfonylphenyl)-n-(pyridin-3-ylmethyl)aniline Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)S(=O)(=O)N2CCOCC2)C=C1OC1CCCC1 GBOMDBPTDBFTII-UHFFFAOYSA-N 0.000 claims 1
- PHMBUKGEPZESLG-UHFFFAOYSA-N 3-cyclopentyloxy-4-methoxy-n-(4-morpholin-4-ylsulfonylphenyl)-n-(pyridin-3-ylmethyl)aniline Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)C=C1OC1CCCC1 PHMBUKGEPZESLG-UHFFFAOYSA-N 0.000 claims 1
- PHBRPGFKBJGQPE-UHFFFAOYSA-N 3-cyclopentyloxy-4-methoxy-n-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-(pyridin-3-ylmethyl)aniline Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1OC1CCCC1 PHBRPGFKBJGQPE-UHFFFAOYSA-N 0.000 claims 1
- MZJFGWOGYZXLKJ-UHFFFAOYSA-N 3-cyclopentyloxy-4-methoxy-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-n-(pyridin-3-ylmethyl)aniline Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1OC1CCCC1 MZJFGWOGYZXLKJ-UHFFFAOYSA-N 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- UJEXGVXQUAGKLK-UHFFFAOYSA-N 4-[(3,5-dichloropyridin-2-yl)methyl]aniline Chemical compound ClC=1C(=NC=C(C=1)Cl)CC1=CC=C(N)C=C1 UJEXGVXQUAGKLK-UHFFFAOYSA-N 0.000 claims 1
- CNANRMBVLDWZGK-UHFFFAOYSA-N 4-[(3-chloropyridin-2-yl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=NC=CC=C1Cl CNANRMBVLDWZGK-UHFFFAOYSA-N 0.000 claims 1
- MJEMMFJBQMIKAY-UHFFFAOYSA-N 4-[3,4-bis(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N(C=1C=C(OC(F)F)C(OC(F)F)=CC=1)CC1=CC=CN=C1 MJEMMFJBQMIKAY-UHFFFAOYSA-N 0.000 claims 1
- ZLCSVNIINHAHOF-UHFFFAOYSA-N 4-[3-(cyclopropylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-(3-fluorophenyl)sulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(=O)(=O)C=2C=C(F)C=CC=2)C=C1OCC1CC1 ZLCSVNIINHAHOF-UHFFFAOYSA-N 0.000 claims 1
- JMKRXXVFFHRDPI-UHFFFAOYSA-N 4-[3-(cyclopropylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)C=C1OCC1CC1 JMKRXXVFFHRDPI-UHFFFAOYSA-N 0.000 claims 1
- HZCREOSJQXPSJW-UHFFFAOYSA-N 4-[3-(cyclopropylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-ethylsulfonylbenzamide Chemical compound C1=CC(C(=O)NS(=O)(=O)CC)=CC=C1N(C=1C=C(OCC2CC2)C(OC)=CC=1)CC1=CC=CN=C1 HZCREOSJQXPSJW-UHFFFAOYSA-N 0.000 claims 1
- ONHDAUIJKHRUGL-UHFFFAOYSA-N 4-[3-cyclobutyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCC1 ONHDAUIJKHRUGL-UHFFFAOYSA-N 0.000 claims 1
- UTBGICCEGURIGQ-UHFFFAOYSA-N 4-[3-cyclohexyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCCC1 UTBGICCEGURIGQ-UHFFFAOYSA-N 0.000 claims 1
- FWIJTJIIROVXLW-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]-n-(3-fluorophenyl)sulfonylbenzamide Chemical compound FC(F)OC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(=O)(=O)C=2C=C(F)C=CC=2)C=C1OC1CCCC1 FWIJTJIIROVXLW-UHFFFAOYSA-N 0.000 claims 1
- KOLMTKWPQSOFLV-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound FC(F)OC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)C=C1OC1CCCC1 KOLMTKWPQSOFLV-UHFFFAOYSA-N 0.000 claims 1
- JWKWDLKITOJRJB-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-2-fluorobenzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(F)C(C(O)=O)=CC=2)C=C1OC1CCCC1 JWKWDLKITOJRJB-UHFFFAOYSA-N 0.000 claims 1
- HKYAIVSQNSOYRR-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-2-methylbenzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C)C(C(O)=O)=CC=2)C=C1OC1CCCC1 HKYAIVSQNSOYRR-UHFFFAOYSA-N 0.000 claims 1
- PLPHAIFSCJDPNH-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-methylsulfonylbenzamide Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(C)(=O)=O)C=C1OC1CCCC1 PLPHAIFSCJDPNH-UHFFFAOYSA-N 0.000 claims 1
- NSHPFJPSUOYGMY-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-4-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=CN=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 NSHPFJPSUOYGMY-UHFFFAOYSA-N 0.000 claims 1
- DOGXBUWLYGJKNK-UHFFFAOYSA-N 4-[3-cyclopentyloxy-n-[(5-fluoropyridin-3-yl)methyl]-4-methoxyanilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=C(F)C=NC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 DOGXBUWLYGJKNK-UHFFFAOYSA-N 0.000 claims 1
- RABPMEPQIKVUDY-UHFFFAOYSA-N 4-[3-ethoxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]-n-(4-fluorophenyl)sulfonylbenzamide Chemical compound C1=C(OC)C(OCC)=CC(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)=C1 RABPMEPQIKVUDY-UHFFFAOYSA-N 0.000 claims 1
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-
2003
- 2003-07-21 WO PCT/US2003/022543 patent/WO2004009552A1/en not_active Ceased
- 2003-07-21 CA CA002492907A patent/CA2492907A1/en not_active Abandoned
- 2003-07-21 RU RU2005104819/04A patent/RU2368604C2/ru not_active IP Right Cessation
- 2003-07-21 CN CNA038223546A patent/CN1688545A/zh active Pending
- 2003-07-21 EP EP03765748A patent/EP1539697A1/en not_active Withdrawn
- 2003-07-21 BR BR0312999-3A patent/BR0312999A/pt not_active IP Right Cessation
- 2003-07-21 HR HR20050083A patent/HRP20050083A2/hr not_active Application Discontinuation
- 2003-07-21 MX MXPA05000827A patent/MXPA05000827A/es active IP Right Grant
- 2003-07-21 JP JP2004523585A patent/JP2006504656A/ja active Pending
- 2003-07-21 US US10/622,833 patent/US7405230B2/en not_active Expired - Fee Related
- 2003-07-21 NZ NZ537724A patent/NZ537724A/en unknown
- 2003-07-21 AU AU2003256616A patent/AU2003256616B2/en not_active Ceased
-
2005
- 2005-01-05 IL IL16616305A patent/IL166163A0/xx unknown
- 2005-01-18 ZA ZA200500488A patent/ZA200500488B/xx unknown
- 2005-01-19 CO CO05003869A patent/CO5680399A2/es not_active Application Discontinuation
- 2005-02-18 NO NO20050870A patent/NO20050870L/no unknown
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