ZA200407766B - Novel alkoxypyridine-derivatives - Google Patents
Novel alkoxypyridine-derivatives Download PDFInfo
- Publication number
- ZA200407766B ZA200407766B ZA200407766A ZA200407766A ZA200407766B ZA 200407766 B ZA200407766 B ZA 200407766B ZA 200407766 A ZA200407766 A ZA 200407766A ZA 200407766 A ZA200407766 A ZA 200407766A ZA 200407766 B ZA200407766 B ZA 200407766B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkoxy
- imidazo
- alkyl
- methoxypyridin
- pyridine
- Prior art date
Links
- -1 9H-purin-8-yl Chemical group 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical group 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 239000011737 fluorine Substances 0.000 claims description 33
- 150000001204 N-oxides Chemical class 0.000 claims description 31
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- 239000005977 Ethylene Substances 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- GBASBDVGJLVABG-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-(2-phenylethyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(CCC=4C=CC=CC=4)C=C3N=2)=C1 GBASBDVGJLVABG-UHFFFAOYSA-N 0.000 claims description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 3
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- YSOUFXVCDIKGFA-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-(4-phenylmethoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 YSOUFXVCDIKGFA-UHFFFAOYSA-N 0.000 claims 1
- WWVDTVBVAWYLCI-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]benzonitrile Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)C#N)=C1 WWVDTVBVAWYLCI-UHFFFAOYSA-N 0.000 claims 1
- XDMGILFUCNKHEV-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(OC)C(OC)=CC=2)=C1 XDMGILFUCNKHEV-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- JAFQAPZAWKZKSD-UHFFFAOYSA-N n-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]acetamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(NC(C)=O)=CC=2)=C1 JAFQAPZAWKZKSD-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 3
- PPAULTVPKLVLII-UHFFFAOYSA-N 4,5-diaminopyrimidine Chemical class NC1=CN=CN=C1N PPAULTVPKLVLII-UHFFFAOYSA-N 0.000 description 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZHDSCPNAZAJOKO-UHFFFAOYSA-N [O]C(F)F Chemical compound [O]C(F)F ZHDSCPNAZAJOKO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 125000005620 boronic acid group Chemical class 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- YBOCDKFRGBOOFO-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=CC=C3N=2)=C1 YBOCDKFRGBOOFO-UHFFFAOYSA-N 0.000 description 1
- WVUFRVRUFULGGY-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-methyl-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C)C=C3N=2)=C1 WVUFRVRUFULGGY-UHFFFAOYSA-N 0.000 description 1
- FTTIAVRPJGCXAC-UHFFFAOYSA-N 2-methyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CC1=CC([N+]([O-])=O)=CC=[N+]1[O-] FTTIAVRPJGCXAC-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 150000005240 3H-imidazo[4,5-b]pyridines Chemical class 0.000 description 1
- KOFVAOOMAVAGHM-UHFFFAOYSA-N 4,6-dimethylpyridine-2,3-diamine Chemical compound CC1=CC(C)=C(N)C(N)=N1 KOFVAOOMAVAGHM-UHFFFAOYSA-N 0.000 description 1
- LHXCEUPUQVSLLT-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenol Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(O)=CC=2)=C1 LHXCEUPUQVSLLT-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- SFXHWRCRQNGVLJ-UHFFFAOYSA-N 4-methoxy-TEMPO Chemical compound COC1CC(C)(C)N([O])C(C)(C)C1 SFXHWRCRQNGVLJ-UHFFFAOYSA-N 0.000 description 1
- UEVABMBUZNGYQI-UHFFFAOYSA-N 4-methoxypyridine-2-carbaldehyde Chemical compound COC1=CC=NC(C=O)=C1 UEVABMBUZNGYQI-UHFFFAOYSA-N 0.000 description 1
- RWGGFJXJRPCCGD-UHFFFAOYSA-N 4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(N)=C1N RWGGFJXJRPCCGD-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- ZUZYUYISVDZDRI-UHFFFAOYSA-N 6-(3-fluoro-4-phenylmethoxyphenyl)-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(F)C(OCC=3C=CC=CC=3)=CC=2)=C1 ZUZYUYISVDZDRI-UHFFFAOYSA-N 0.000 description 1
- CANPUUOGYAPGDH-UHFFFAOYSA-N 6-(4-bromophenyl)-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(Br)=CC=2)=C1 CANPUUOGYAPGDH-UHFFFAOYSA-N 0.000 description 1
- BKUZSRKWRJKDAU-UHFFFAOYSA-N 6-[(4-bromophenyl)methyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(CC=4C=CC(Br)=CC=4)C=C3N=2)=C1 BKUZSRKWRJKDAU-UHFFFAOYSA-N 0.000 description 1
- XNZJPDGHSRBBKS-UHFFFAOYSA-N 6-iodo-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(I)C=C3N=2)=C1 XNZJPDGHSRBBKS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
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- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- DEEVWIIFCDFVPD-UHFFFAOYSA-N methyl 3-(4-methoxypyridin-2-yl)propanoate Chemical compound COC(=O)CCC1=CC(OC)=CC=N1 DEEVWIIFCDFVPD-UHFFFAOYSA-N 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- WVUCPRGADMCTBN-UHFFFAOYSA-M potassium;3-ethoxy-3-oxopropanoate Chemical compound [K+].CCOC(=O)CC([O-])=O WVUCPRGADMCTBN-UHFFFAOYSA-M 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
Classifications
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02007049 | 2002-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200407766B true ZA200407766B (en) | 2006-06-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200407766A ZA200407766B (en) | 2002-03-27 | 2004-09-27 | Novel alkoxypyridine-derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7138399B2 (zh) |
| EP (1) | EP1490366B1 (zh) |
| JP (1) | JP4448695B2 (zh) |
| KR (1) | KR20050002910A (zh) |
| CN (1) | CN1307176C (zh) |
| AT (1) | ATE384722T1 (zh) |
| AU (1) | AU2003226706A1 (zh) |
| BR (1) | BR0308785A (zh) |
| CA (1) | CA2480385A1 (zh) |
| DE (1) | DE60318826T2 (zh) |
| ES (1) | ES2300599T3 (zh) |
| IL (1) | IL163625A0 (zh) |
| MX (1) | MXPA04009283A (zh) |
| NO (1) | NO20044633L (zh) |
| NZ (1) | NZ535959A (zh) |
| PL (1) | PL372409A1 (zh) |
| WO (1) | WO2003080607A1 (zh) |
| ZA (1) | ZA200407766B (zh) |
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| WO2005061496A1 (en) | 2003-10-01 | 2005-07-07 | Altana Pharma Ag | Aminopyridine-derivatives as inductible no-synthase inhibitors |
| NZ546435A (en) * | 2003-10-01 | 2009-08-28 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| DE602004014523D1 (de) * | 2003-10-01 | 2008-07-31 | Nycomed Gmbh | Imidazoä4,5-büpyridinderivate als inhibitoren der induzierbaren no-synthase |
| KR20060092222A (ko) * | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-합성효소 억제제로서의 이미다조피리딘-유도체 |
| US7468377B2 (en) * | 2003-10-01 | 2008-12-23 | Altana Pharma Ag | Imidazopyridine-derivatives as inductible no-synthase inhibitors |
| WO2005063732A1 (en) * | 2003-12-23 | 2005-07-14 | Microbia, Inc. | Compounds and methods for the treatment of asthma |
| AU2005249718B2 (en) | 2004-05-28 | 2011-01-27 | 4Sc Ag | Tetrahydropyridothiophenes |
| AU2005251485A1 (en) | 2004-06-11 | 2005-12-22 | 4Sc Ag | Tetrahydropyridothiophenes for treating hyperproliferative disorders |
| CA2596202A1 (en) | 2005-02-09 | 2006-08-17 | Altana Pharma Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| AU2006212179A1 (en) | 2005-02-11 | 2006-08-17 | 4Sc Ag | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| EP1866306B1 (en) * | 2005-03-31 | 2009-06-17 | Nycomed GmbH | Imidazopyridine derivatives useful as inos inhibitors |
| US7714136B2 (en) | 2005-05-25 | 2010-05-11 | 4Sc Ag | Tetrahydropyridothiophenes |
| CA2609004A1 (en) | 2005-05-25 | 2006-11-30 | Nycomed Gmbh | Tetrahydropyridothiophenes for use in the treatment of cancer |
| UY29825A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones |
| AR057525A1 (es) * | 2005-10-03 | 2007-12-05 | Astrazeneca Ab | Compuestos inhibidores selectivos de gsk3 y un proceso para su preparacion |
| WO2008031788A1 (en) * | 2006-09-12 | 2008-03-20 | Nycomed Gmbh | Aminoazepine derivatives as highly efficient inhibitors of the inducible nitric oxide synthase |
| US20080139608A1 (en) * | 2006-12-06 | 2008-06-12 | Universiteit Leiden | 2,6,8, Trisubstituted 1-deazapurines and their different uses |
| CN105001219A (zh) * | 2011-02-25 | 2015-10-28 | 默沙东公司 | 用作抗糖尿病药剂的新的环状氮杂苯并咪唑衍生物 |
| JP6108467B2 (ja) | 2011-07-15 | 2017-04-05 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するアザベンズイミダゾール誘導体 |
| GB201512635D0 (en) | 2015-07-17 | 2015-08-26 | Ucl Business Plc | Uses of therapeutic compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| GB8307865D0 (en) | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| GB8515934D0 (en) * | 1985-06-24 | 1985-07-24 | Janssen Pharmaceutica Nv | (4-piperidinomethyl and-hetero)purines |
| SE512835C2 (sv) * | 1996-01-08 | 2000-05-22 | Astrazeneca Ab | Doseringsform innehållande en mångfald enheter alla inneslutande syralabil H+K+ATPas-hämmare |
-
2003
- 2003-03-25 AT AT03744851T patent/ATE384722T1/de not_active IP Right Cessation
- 2003-03-25 ES ES03744851T patent/ES2300599T3/es not_active Expired - Lifetime
- 2003-03-25 WO PCT/EP2003/003076 patent/WO2003080607A1/en active IP Right Grant
- 2003-03-25 JP JP2003578361A patent/JP4448695B2/ja not_active Expired - Fee Related
- 2003-03-25 KR KR10-2004-7015438A patent/KR20050002910A/ko not_active Ceased
- 2003-03-25 DE DE60318826T patent/DE60318826T2/de not_active Expired - Lifetime
- 2003-03-25 NZ NZ535959A patent/NZ535959A/en not_active IP Right Cessation
- 2003-03-25 MX MXPA04009283A patent/MXPA04009283A/es active IP Right Grant
- 2003-03-25 PL PL03372409A patent/PL372409A1/xx not_active Application Discontinuation
- 2003-03-25 IL IL16362503A patent/IL163625A0/xx unknown
- 2003-03-25 BR BR0308785-9A patent/BR0308785A/pt not_active IP Right Cessation
- 2003-03-25 US US10/509,396 patent/US7138399B2/en not_active Expired - Fee Related
- 2003-03-25 CA CA002480385A patent/CA2480385A1/en not_active Abandoned
- 2003-03-25 CN CNB038069172A patent/CN1307176C/zh not_active Expired - Fee Related
- 2003-03-25 EP EP03744851A patent/EP1490366B1/en not_active Expired - Lifetime
- 2003-03-25 AU AU2003226706A patent/AU2003226706A1/en not_active Abandoned
-
2004
- 2004-09-27 ZA ZA200407766A patent/ZA200407766B/en unknown
- 2004-10-27 NO NO20044633A patent/NO20044633L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0308785A (pt) | 2005-01-11 |
| CN1642955A (zh) | 2005-07-20 |
| WO2003080607A1 (en) | 2003-10-02 |
| US20050171125A1 (en) | 2005-08-04 |
| DE60318826D1 (de) | 2008-03-13 |
| NO20044633L (no) | 2004-12-23 |
| MXPA04009283A (es) | 2005-01-25 |
| EP1490366A1 (en) | 2004-12-29 |
| EP1490366B1 (en) | 2008-01-23 |
| CA2480385A1 (en) | 2003-10-02 |
| NZ535959A (en) | 2006-05-26 |
| US7138399B2 (en) | 2006-11-21 |
| HK1078850A1 (zh) | 2006-03-24 |
| DE60318826T2 (de) | 2009-01-22 |
| JP4448695B2 (ja) | 2010-04-14 |
| ATE384722T1 (de) | 2008-02-15 |
| CN1307176C (zh) | 2007-03-28 |
| JP2005525388A (ja) | 2005-08-25 |
| PL372409A1 (en) | 2005-07-25 |
| AU2003226706A1 (en) | 2003-10-08 |
| IL163625A0 (en) | 2005-12-18 |
| KR20050002910A (ko) | 2005-01-10 |
| ES2300599T3 (es) | 2008-06-16 |
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