AU2003237386A1 - Ether substituted imidazopyridines - Google Patents
Ether substituted imidazopyridines Download PDFInfo
- Publication number
- AU2003237386A1 AU2003237386A1 AU2003237386A AU2003237386A AU2003237386A1 AU 2003237386 A1 AU2003237386 A1 AU 2003237386A1 AU 2003237386 A AU2003237386 A AU 2003237386A AU 2003237386 A AU2003237386 A AU 2003237386A AU 2003237386 A1 AU2003237386 A1 AU 2003237386A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkylene
- compound
- imidazo
- aryl
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 116
- 150000005232 imidazopyridines Chemical class 0.000 title description 4
- 125000001033 ether group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 362
- 229910052739 hydrogen Inorganic materials 0.000 claims description 191
- 125000000217 alkyl group Chemical group 0.000 claims description 168
- 239000001257 hydrogen Substances 0.000 claims description 156
- 150000003839 salts Chemical class 0.000 claims description 127
- 125000003342 alkenyl group Chemical group 0.000 claims description 98
- -1 alkyqlamino Chemical group 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000002947 alkylene group Chemical group 0.000 claims description 55
- 241001465754 Metazoa Species 0.000 claims description 54
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
- 125000004450 alkenylene group Chemical group 0.000 claims description 53
- 125000004419 alkynylene group Chemical group 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 32
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 32
- 102000004127 Cytokines Human genes 0.000 claims description 31
- 108090000695 Cytokines Proteins 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 14
- 230000003612 virological effect Effects 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 230000001613 neoplastic effect Effects 0.000 claims description 12
- 230000001939 inductive effect Effects 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 230000002452 interceptive effect Effects 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 102000014150 Interferons Human genes 0.000 claims description 2
- 108010050904 Interferons Proteins 0.000 claims description 2
- 229940079322 interferon Drugs 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 329
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 217
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 193
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 169
- 239000000243 solution Substances 0.000 description 137
- 239000000047 product Substances 0.000 description 132
- 239000011541 reaction mixture Substances 0.000 description 125
- 230000002829 reductive effect Effects 0.000 description 124
- 229960004979 fampridine Drugs 0.000 description 121
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 119
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 112
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 105
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 105
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 95
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- 239000002904 solvent Substances 0.000 description 91
- 239000007787 solid Substances 0.000 description 89
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- 150000001412 amines Chemical class 0.000 description 78
- 238000007796 conventional method Methods 0.000 description 78
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 75
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 66
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 56
- 235000019341 magnesium sulphate Nutrition 0.000 description 56
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 55
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 55
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 54
- 239000003921 oil Substances 0.000 description 53
- 235000019198 oils Nutrition 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 50
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical compound NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- QZLAVKQIKWPEEU-UHFFFAOYSA-N 3,4,5,6,10,12-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaene Chemical compound C1=CN2N=NN=C2C2=C1NC=N2 QZLAVKQIKWPEEU-UHFFFAOYSA-N 0.000 description 37
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- 239000012267 brine Substances 0.000 description 34
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- 238000004458 analytical method Methods 0.000 description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 27
- 238000010438 heat treatment Methods 0.000 description 25
- 238000004128 high performance liquid chromatography Methods 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- 230000009467 reduction Effects 0.000 description 24
- 239000012312 sodium hydride Substances 0.000 description 24
- 229910000104 sodium hydride Inorganic materials 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 22
- 239000005695 Ammonium acetate Substances 0.000 description 22
- 235000019257 ammonium acetate Nutrition 0.000 description 22
- 229940043376 ammonium acetate Drugs 0.000 description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000004809 thin layer chromatography Methods 0.000 description 17
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- HPYDPDYKFJEKPK-UHFFFAOYSA-N 4-phenoxy-1h-imidazo[4,5-c]pyridine Chemical compound N=1C=CC=2NC=NC=2C=1OC1=CC=CC=C1 HPYDPDYKFJEKPK-UHFFFAOYSA-N 0.000 description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 150000001266 acyl halides Chemical class 0.000 description 15
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 9
- SUUZDNBBAQOFQR-UHFFFAOYSA-N 3-nitro-2-phenoxypyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1OC1=CC=CC=C1 SUUZDNBBAQOFQR-UHFFFAOYSA-N 0.000 description 9
- JERQIJCVPYQVLS-UHFFFAOYSA-N 8-nitrotetrazolo[1,5-a]pyridine Chemical compound [O-][N+](=O)C1=CC=CN2N=NN=C12 JERQIJCVPYQVLS-UHFFFAOYSA-N 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 238000011065 in-situ storage Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- KSQNRBBVJBZZTG-UHFFFAOYSA-N 2-phenoxypyridine-3,4-diamine Chemical compound NC1=CC=NC(OC=2C=CC=CC=2)=C1N KSQNRBBVJBZZTG-UHFFFAOYSA-N 0.000 description 8
- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical compound C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- WXBFCJDNQZFOPX-UHFFFAOYSA-N tetrazolo[1,5-a]pyridine-7,8-diamine Chemical compound NC1=C(N)C=CN2N=NN=C21 WXBFCJDNQZFOPX-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- JPEPQJIRNGWRCA-UHFFFAOYSA-N 1-[2-(2-aminoethoxy)ethyl]-2,6,7-trimethylimidazo[4,5-c]pyridin-4-amine Chemical compound N1=C(C)C(C)=C2N(CCOCCN)C(C)=NC2=C1N JPEPQJIRNGWRCA-UHFFFAOYSA-N 0.000 description 7
- CEGLXJGCOGYSFS-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethyl-3-nitropyridine Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=C1C CEGLXJGCOGYSFS-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000002638 heterogeneous catalyst Substances 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 150000002905 orthoesters Chemical class 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 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 6
- 150000003568 thioethers Chemical class 0.000 description 6
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 5
- 125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
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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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- 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
- A61P33/00—Antiparasitic agents
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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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Immunology (AREA)
- Oncology (AREA)
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- Virology (AREA)
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- Biomedical Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Toxicology (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 |
|---|---|---|---|
| US38726802P | 2002-06-07 | 2002-06-07 | |
| US60/387,268 | 2002-06-07 | ||
| PCT/US2003/017659 WO2003103584A2 (en) | 2002-06-07 | 2003-06-06 | Ether substituted imidazopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003237386A1 true AU2003237386A1 (en) | 2003-12-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003237386A Abandoned AU2003237386A1 (en) | 2002-06-07 | 2003-06-06 | Ether substituted imidazopyridines |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US6797718B2 (https=) |
| EP (1) | EP1513524A4 (https=) |
| JP (1) | JP2005538057A (https=) |
| CN (1) | CN1674894A (https=) |
| AU (1) | AU2003237386A1 (https=) |
| BR (1) | BR0311648A (https=) |
| CA (1) | CA2488801A1 (https=) |
| IL (1) | IL165604A0 (https=) |
| MX (1) | MXPA04012199A (https=) |
| NO (1) | NO20045445L (https=) |
| NZ (1) | NZ537054A (https=) |
| WO (1) | WO2003103584A2 (https=) |
| ZA (1) | ZA200500135B (https=) |
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| UA67760C2 (uk) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| US6613318B1 (en) * | 1999-03-25 | 2003-09-02 | The United States Of America As Represented By The Department Of Health And Human Services | Methods for identifying inhibitors of GADD45 polypeptide activity, and inhibitors of such activity |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US20060142202A1 (en) * | 2000-12-08 | 2006-06-29 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
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-
2003
- 2003-06-06 MX MXPA04012199A patent/MXPA04012199A/es not_active Application Discontinuation
- 2003-06-06 NZ NZ537054A patent/NZ537054A/en unknown
- 2003-06-06 US US10/456,308 patent/US6797718B2/en not_active Expired - Fee Related
- 2003-06-06 AU AU2003237386A patent/AU2003237386A1/en not_active Abandoned
- 2003-06-06 EP EP03736844A patent/EP1513524A4/en not_active Withdrawn
- 2003-06-06 WO PCT/US2003/017659 patent/WO2003103584A2/en not_active Ceased
- 2003-06-06 CN CNA038186780A patent/CN1674894A/zh active Pending
- 2003-06-06 JP JP2004510705A patent/JP2005538057A/ja active Pending
- 2003-06-06 BR BR0311648-4A patent/BR0311648A/pt not_active IP Right Cessation
- 2003-06-06 CA CA002488801A patent/CA2488801A1/en not_active Abandoned
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2004
- 2004-08-11 US US10/916,125 patent/US7125890B2/en not_active Expired - Fee Related
- 2004-12-07 IL IL16560404A patent/IL165604A0/xx unknown
- 2004-12-14 NO NO20045445A patent/NO20045445L/no not_active Application Discontinuation
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2005
- 2005-01-06 ZA ZA200500135A patent/ZA200500135B/en unknown
-
2006
- 2006-07-24 US US11/459,489 patent/US7220758B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04012199A (es) | 2005-02-25 |
| EP1513524A4 (en) | 2008-09-03 |
| US6797718B2 (en) | 2004-09-28 |
| JP2005538057A (ja) | 2005-12-15 |
| US20050032830A1 (en) | 2005-02-10 |
| US7220758B2 (en) | 2007-05-22 |
| US7125890B2 (en) | 2006-10-24 |
| US20040010007A1 (en) | 2004-01-15 |
| NZ537054A (en) | 2006-10-27 |
| WO2003103584A3 (en) | 2004-02-26 |
| NO20045445L (no) | 2005-02-18 |
| WO2003103584A2 (en) | 2003-12-18 |
| ZA200500135B (en) | 2006-06-28 |
| EP1513524A2 (en) | 2005-03-16 |
| BR0311648A (pt) | 2005-04-19 |
| CN1674894A (zh) | 2005-09-28 |
| IL165604A0 (en) | 2006-01-15 |
| CA2488801A1 (en) | 2003-12-18 |
| US20060252792A1 (en) | 2006-11-09 |
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