AU2006287157A1 - Hydroxy substituted 1H-imidazopyridines and methods - Google Patents
Hydroxy substituted 1H-imidazopyridines and methods Download PDFInfo
- Publication number
- AU2006287157A1 AU2006287157A1 AU2006287157A AU2006287157A AU2006287157A1 AU 2006287157 A1 AU2006287157 A1 AU 2006287157A1 AU 2006287157 A AU2006287157 A AU 2006287157A AU 2006287157 A AU2006287157 A AU 2006287157A AU 2006287157 A1 AU2006287157 A1 AU 2006287157A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- alkyl
- compound
- alkylenyl
- amino
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 67
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims 9
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 147
- 150000003839 salts Chemical class 0.000 claims description 94
- 125000005466 alkylenyl group Chemical group 0.000 claims description 89
- -1 arylalkylenyl Chemical group 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 241001465754 Metazoa Species 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 102000004127 Cytokines Human genes 0.000 claims description 46
- 108090000695 Cytokines Proteins 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 201000010099 disease Diseases 0.000 claims description 30
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 125000004450 alkenylene group Chemical group 0.000 claims description 16
- 125000004419 alkynylene group Chemical group 0.000 claims description 16
- 125000005549 heteroarylene group Chemical group 0.000 claims description 16
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 16
- 230000003612 virological effect Effects 0.000 claims description 14
- 230000001939 inductive effect Effects 0.000 claims description 12
- 230000001613 neoplastic effect Effects 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 150000008575 L-amino acids Chemical class 0.000 claims description 10
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 213
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 199
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
- 239000000243 solution Substances 0.000 description 137
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 114
- 239000007787 solid Substances 0.000 description 89
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 79
- 239000000203 mixture Substances 0.000 description 69
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- 239000000463 material Substances 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 239000003921 oil Substances 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 55
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- 238000003818 flash chromatography Methods 0.000 description 46
- 239000002904 solvent Substances 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
- 238000010992 reflux Methods 0.000 description 32
- 239000000741 silica gel Substances 0.000 description 31
- 229910002027 silica gel Inorganic materials 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 239000000725 suspension Substances 0.000 description 30
- 239000012279 sodium borohydride Substances 0.000 description 29
- 229910000033 sodium borohydride Inorganic materials 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- 239000012267 brine Substances 0.000 description 28
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 27
- 239000010410 layer Substances 0.000 description 27
- 102100040247 Tumor necrosis factor Human genes 0.000 description 24
- 239000012043 crude product Substances 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 23
- 238000001914 filtration Methods 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 22
- 238000000746 purification Methods 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 230000006698 induction Effects 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 19
- 229920006395 saturated elastomer Polymers 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 125000001309 chloro group Chemical group Cl* 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 18
- 238000002390 rotary evaporation Methods 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- ZJSVBILSBHWRTN-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]pyridin-2-one Chemical compound C1=NC=C2NC(=O)NC2=C1 ZJSVBILSBHWRTN-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- NFMMTHTXOVXHFW-UHFFFAOYSA-N 2,4-dichloro-3-nitro-6-pentylpyridine Chemical compound CCCCCC1=CC(Cl)=C([N+]([O-])=O)C(Cl)=N1 NFMMTHTXOVXHFW-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- HBKPDEWGANZHJO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[(4-methoxyphenyl)methyl]methanamine Chemical group C1=CC(OC)=CC=C1CNCC1=CC=C(OC)C=C1 HBKPDEWGANZHJO-UHFFFAOYSA-N 0.000 description 10
- 230000028993 immune response Effects 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 210000000265 leukocyte Anatomy 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 6
- APXBXAJWVZTKSE-UHFFFAOYSA-N pyridine-2,3,4-triamine Chemical compound NC1=CC=NC(N)=C1N APXBXAJWVZTKSE-UHFFFAOYSA-N 0.000 description 6
- KJVKGYRFRFXCQQ-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridin-4-amine Chemical class NC1=CC(Cl)=NC(Cl)=C1[N+]([O-])=O KJVKGYRFRFXCQQ-UHFFFAOYSA-N 0.000 description 5
- VEJMLGQIVQLVTM-UHFFFAOYSA-N 4-amino-6-pentyl-1-(piperidin-4-ylmethyl)-3h-imidazo[4,5-c]pyridin-2-one Chemical compound OC1=NC=2C(N)=NC(CCCCC)=CC=2N1CC1CCNCC1 VEJMLGQIVQLVTM-UHFFFAOYSA-N 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
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- 125000006239 protecting group Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 4
- RTXYIHGMYDJHEU-UHFFFAOYSA-N 2,4-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=C(Cl)C=CN=C1Cl RTXYIHGMYDJHEU-UHFFFAOYSA-N 0.000 description 4
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 238000001514 detection method Methods 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- AIMCUTZXDCCWFQ-UHFFFAOYSA-N ethanol hydrate Chemical compound O.C(C)O.C(C)O.C(C)O.C(C)O AIMCUTZXDCCWFQ-UHFFFAOYSA-N 0.000 description 4
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- ZEZJPIDPVXJEME-UHFFFAOYSA-N 2,4-Dihydroxypyridine Chemical compound OC=1C=CNC(=O)C=1 ZEZJPIDPVXJEME-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 150000008574 D-amino acids Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- 102000003814 Interleukin-10 Human genes 0.000 description 3
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- 229930194542 Keto Natural products 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000010934 O-alkylation reaction Methods 0.000 description 3
- 241000725643 Respiratory syncytial virus Species 0.000 description 3
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
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- FLGMAMYMYDIKLE-UHFFFAOYSA-N chloro hypochlorite;phosphane Chemical compound P.ClOCl FLGMAMYMYDIKLE-UHFFFAOYSA-N 0.000 description 3
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- 201000005404 rubella Diseases 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- NCVDTZUTTBBFCE-UHFFFAOYSA-N tert-butyl 3,5-dioxodecanoate Chemical compound CCCCCC(=O)CC(=O)CC(=O)OC(C)(C)C NCVDTZUTTBBFCE-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- RCRCVGVTGMAKIK-UHFFFAOYSA-N tert-butyl 4-[[[2-[bis[(4-methoxyphenyl)methyl]amino]-3-nitro-6-pentylpyridin-4-yl]amino]methyl]piperidine-1-carboxylate Chemical compound [O-][N+](=O)C=1C(N(CC=2C=CC(OC)=CC=2)CC=2C=CC(OC)=CC=2)=NC(CCCCC)=CC=1NCC1CCN(C(=O)OC(C)(C)C)CC1 RCRCVGVTGMAKIK-UHFFFAOYSA-N 0.000 description 1
- FXKWOBDAKKKUCL-UHFFFAOYSA-N tert-butyl 4-[[[3-amino-2-[bis[(4-methoxyphenyl)methyl]amino]-6-pentylpyridin-4-yl]amino]methyl]piperidine-1-carboxylate Chemical compound NC=1C(N(CC=2C=CC(OC)=CC=2)CC=2C=CC(OC)=CC=2)=NC(CCCCC)=CC=1NCC1CCN(C(=O)OC(C)(C)C)CC1 FXKWOBDAKKKUCL-UHFFFAOYSA-N 0.000 description 1
- POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
- OQTSNKZEZIUDAF-UHFFFAOYSA-N tert-butyl n-[(2-chloro-3-nitropyridin-4-yl)amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC1=CC=NC(Cl)=C1[N+]([O-])=O OQTSNKZEZIUDAF-UHFFFAOYSA-N 0.000 description 1
- RYNCNMVBPNHRLM-UHFFFAOYSA-N tert-butyl n-[3-[(2-chloro-3-nitro-6-pentylpyridin-4-yl)amino]propyl]carbamate Chemical compound CCCCCC1=CC(NCCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C(Cl)=N1 RYNCNMVBPNHRLM-UHFFFAOYSA-N 0.000 description 1
- RSEIDSKOBOWSEQ-UHFFFAOYSA-N tert-butyl n-[3-[[2-[bis[(4-methoxyphenyl)methyl]amino]-3-nitro-6-pentylpyridin-4-yl]amino]propyl]carbamate Chemical compound CCCCCC1=CC(NCCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C(N(CC=2C=CC(OC)=CC=2)CC=2C=CC(OC)=CC=2)=N1 RSEIDSKOBOWSEQ-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71370405P | 2005-09-02 | 2005-09-02 | |
| US60/713,704 | 2005-09-02 | ||
| PCT/US2006/034427 WO2007028129A1 (en) | 2005-09-02 | 2006-09-01 | Hydroxy substituted 1h-imidazopyridines and methods |
Publications (1)
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|---|---|
| AU2006287157A1 true AU2006287157A1 (en) | 2007-03-08 |
Family
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Family Applications (1)
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| AU2006287157A Abandoned AU2006287157A1 (en) | 2005-09-02 | 2006-09-01 | Hydroxy substituted 1H-imidazopyridines and methods |
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| BR (1) | BRPI0615250A2 (enExample) |
| CA (1) | CA2620933A1 (enExample) |
| CR (1) | CR9781A (enExample) |
| EA (1) | EA200800396A1 (enExample) |
| EC (1) | ECSP088225A (enExample) |
| IL (1) | IL189262A0 (enExample) |
| MA (1) | MA29759B1 (enExample) |
| MX (1) | MX2008002414A (enExample) |
| NO (1) | NO20081393L (enExample) |
| RS (1) | RS20080128A (enExample) |
| SV (1) | SV2009002832A (enExample) |
| TN (1) | TNSN08099A1 (enExample) |
| WO (1) | WO2007028129A1 (enExample) |
| ZA (1) | ZA200801645B (enExample) |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2005018551A2 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| CA2536136C (en) | 2003-08-27 | 2012-10-30 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| WO2005023190A2 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| EP1696912B1 (en) | 2003-10-03 | 2016-05-11 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| MY161812A (en) | 2003-11-25 | 2017-05-15 | 3M Innovative Properties Co | Substituted imidazo ring systems and methods |
| JP2007517035A (ja) | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| JP2007517044A (ja) | 2003-12-30 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | イミダゾキノリニル、イミダゾピリジニル、およびイミダゾナフチリジニルスルホンアミド |
| TW200612932A (en) | 2004-03-24 | 2006-05-01 | 3M Innovative Properties Co | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| WO2006009826A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| ES2384390T3 (es) | 2004-09-02 | 2012-07-04 | 3M Innovative Properties Company | Sistemas cíclicos 1-alcoxi-1H-imidazo y métodos asociados |
| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| CA2592904C (en) | 2004-12-30 | 2015-04-07 | 3M Innovative Properties Company | Chiral fused [1,2]imidazo[4,5-c] ring compounds |
| AU2006210392A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune response modifiers |
| CA2602083A1 (en) | 2005-02-09 | 2006-08-09 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| WO2006086449A2 (en) | 2005-02-09 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| JP2008532933A (ja) | 2005-02-11 | 2008-08-21 | コーリー ファーマシューティカル グループ，インコーポレイテッド | 置換イミダゾキノリン類および置換イミダゾナフチリジン類 |
| WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| US8846710B2 (en) | 2005-02-23 | 2014-09-30 | 3M Innovative Properties Company | Method of preferentially inducing the biosynthesis of interferon |
| WO2006098852A2 (en) | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| JP2008531567A (ja) | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキル置換イミダゾキノリン化合物および方法 |
| EP1863814A1 (en) | 2005-04-01 | 2007-12-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| WO2006107853A2 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
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| CN101309687A (zh) | 2005-11-04 | 2008-11-19 | 科勒制药集团公司 | 经羟基和烷氧基取代的1h-咪唑并喹啉及其方法 |
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| EP1997805A1 (en) * | 2007-06-01 | 2008-12-03 | Commissariat à l'Energie Atomique | Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans |
| ATE501136T1 (de) * | 2007-08-03 | 2011-03-15 | Pfizer Ltd | Imidazopyridinone |
| US8802684B2 (en) | 2008-08-11 | 2014-08-12 | Glaxosmithkline Llc | Adenine derivatives |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
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| PE20120106A1 (es) | 2008-12-09 | 2012-02-20 | Gilead Sciences Inc | Moduladores de receptores tipo toll |
| JP2013503187A (ja) | 2009-08-28 | 2013-01-31 | アレイ バイオファーマ、インコーポレイテッド | Ｒａｆ阻害化合物およびその使用方法 |
| EA020488B1 (ru) | 2009-10-22 | 2014-11-28 | Джилид Сайэнс, Инк. | Производные пурина или деазапурина для применения при лечении вирусных инфекций и других заболеваний |
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| WO2014081644A1 (en) | 2012-11-20 | 2014-05-30 | Glaxosmithkline Llc | Novel compounds |
| WO2014081643A1 (en) | 2012-11-20 | 2014-05-30 | Glaxosmithkline Llc | Novel compounds |
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| CN115151546A (zh) | 2020-01-27 | 2022-10-04 | 百时美施贵宝公司 | 作为Toll样受体7(TLR7)激动剂的C3-取代的1H-吡唑并[4,3-d]嘧啶化合物 |
| KR20220132602A (ko) | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
| JP7712941B2 (ja) | 2020-01-27 | 2025-07-24 | ブリストル－マイヤーズ スクイブ カンパニー | トール様受容体７（ＴＬＲ７）アゴニストとしての１Ｈ－ピラゾロ［４，３－ｄ］ピリミジン化合物 |
| US20230131192A1 (en) | 2020-01-27 | 2023-04-27 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| KR20220132593A (ko) | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
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| CN117466808B (zh) * | 2023-12-27 | 2024-03-12 | 烟台新药创制山东省实验室 | 一种6-烷基-2,4-二羟基吡啶类衍生物的制备方法 |
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|---|---|---|---|---|
| CZ288182B6 (en) * | 1993-07-15 | 2001-05-16 | Minnesota Mining & Mfg | Imidazo[4,5-c]pyridine-4-amines and pharmaceutical preparations based thereon |
| ATE283855T1 (de) * | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| JP4331944B2 (ja) * | 2001-04-17 | 2009-09-16 | 大日本住友製薬株式会社 | 新規アデニン誘導体 |
| BR0209252A (pt) * | 2001-04-27 | 2004-07-20 | Eisai Co Ltd | Pirazolo[1,5-a]piridinas e medicamentos contendo as mesmas |
| AU2003237386A1 (en) * | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| WO2004076450A1 (en) * | 2003-02-27 | 2004-09-10 | J. Uriach Y Compañia S.A. | Pyrazolopyridine derivates |
| US7517887B2 (en) * | 2003-04-09 | 2009-04-14 | General Atomics | Reversible inhibitors of S-adenosyl-L-homocysteine hydrolase and uses thereof |
| JP2005089334A (ja) * | 2003-09-12 | 2005-04-07 | Sumitomo Pharmaceut Co Ltd | ８−ヒドロキシアデニン化合物 |
| KR101137311B1 (ko) * | 2003-09-22 | 2012-04-23 | 얀센 파마슈티카 엔.브이. | 7-아미노알킬리데닐-헤테로사이클릭 퀴놀론 및 나프티리돈 |
| FR2860514A1 (fr) * | 2003-10-03 | 2005-04-08 | Sanofi Synthelabo | Derives d'arylalkylcarbamates, leur preparation et leur application en therapeutique |
| EP1685129A4 (en) * | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| MY161812A (en) * | 2003-11-25 | 2017-05-15 | 3M Innovative Properties Co | Substituted imidazo ring systems and methods |
| TW200616604A (en) * | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| KR20080085232A (ko) * | 2006-02-17 | 2008-09-23 | 화이자 리미티드 | Ｔｌｒ7 조절제로서 3-데아자퓨린 유도체 |
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2006
- 2006-09-01 EP EP06802901A patent/EP1924581A1/en not_active Withdrawn
- 2006-09-01 BR BRPI0615250-3A patent/BRPI0615250A2/pt not_active IP Right Cessation
- 2006-09-01 JP JP2008529359A patent/JP4584335B2/ja not_active Expired - Fee Related
- 2006-09-01 CA CA002620933A patent/CA2620933A1/en not_active Abandoned
- 2006-09-01 MX MX2008002414A patent/MX2008002414A/es unknown
- 2006-09-01 CN CNA2006800319190A patent/CN101253173A/zh active Pending
- 2006-09-01 US US12/065,490 patent/US20100152230A1/en not_active Abandoned
- 2006-09-01 AU AU2006287157A patent/AU2006287157A1/en not_active Abandoned
- 2006-09-01 RS RSP-2008/0128A patent/RS20080128A/sr unknown
- 2006-09-01 EA EA200800396A patent/EA200800396A1/ru unknown
- 2006-09-01 WO PCT/US2006/034427 patent/WO2007028129A1/en not_active Ceased
- 2006-09-01 KR KR1020087005146A patent/KR20080031496A/ko not_active Ceased
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2008
- 2008-02-04 IL IL189262A patent/IL189262A0/en unknown
- 2008-02-19 ZA ZA200801645A patent/ZA200801645B/xx unknown
- 2008-02-26 EC EC2008008225A patent/ECSP088225A/es unknown
- 2008-02-29 MA MA30694A patent/MA29759B1/fr unknown
- 2008-02-29 TN TNP2008000099A patent/TNSN08099A1/fr unknown
- 2008-02-29 CR CR9781A patent/CR9781A/es not_active Application Discontinuation
- 2008-02-29 SV SV2008002832A patent/SV2009002832A/es not_active Application Discontinuation
- 2008-03-17 NO NO20081393A patent/NO20081393L/no not_active Application Discontinuation
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2011
- 2011-10-20 US US13/277,619 patent/US20120035209A1/en not_active Abandoned
Also Published As
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| WO2007028129A1 (en) | 2007-03-08 |
| NO20081393L (no) | 2008-05-28 |
| SV2009002832A (es) | 2009-02-19 |
| EP1924581A1 (en) | 2008-05-28 |
| KR20080031496A (ko) | 2008-04-08 |
| US20120035209A1 (en) | 2012-02-09 |
| RS20080128A (sr) | 2009-05-06 |
| CR9781A (es) | 2008-03-26 |
| MX2008002414A (es) | 2008-03-27 |
| ECSP088225A (es) | 2008-03-26 |
| BRPI0615250A2 (pt) | 2011-05-10 |
| US20100152230A1 (en) | 2010-06-17 |
| ZA200801645B (en) | 2010-08-25 |
| TNSN08099A1 (fr) | 2009-07-14 |
| CN101253173A (zh) | 2008-08-27 |
| MA29759B1 (fr) | 2008-09-01 |
| IL189262A0 (en) | 2008-06-05 |
| CA2620933A1 (en) | 2007-03-08 |
| JP2009507036A (ja) | 2009-02-19 |
| EA200800396A1 (ru) | 2008-08-29 |
| JP4584335B2 (ja) | 2010-11-17 |
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