NZ542153A - Processes for the preparation of N-heteroaryl-N-aryl-amines by reacting an N-aryl carbamic acid ester with a halo-heteroaryl and analogous processes - Google Patents
Processes for the preparation of N-heteroaryl-N-aryl-amines by reacting an N-aryl carbamic acid ester with a halo-heteroaryl and analogous processesInfo
- Publication number
- NZ542153A NZ542153A NZ542153A NZ54215304A NZ542153A NZ 542153 A NZ542153 A NZ 542153A NZ 542153 A NZ542153 A NZ 542153A NZ 54215304 A NZ54215304 A NZ 54215304A NZ 542153 A NZ542153 A NZ 542153A
- Authority
- NZ
- New Zealand
- Prior art keywords
- process according
- formula
- compound
- alkali metal
- metal salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 105
- 230000008569 process Effects 0.000 title claims abstract description 93
- 238000002360 preparation method Methods 0.000 title description 8
- 125000005216 haloheteroaryl group Chemical group 0.000 title description 2
- -1 diaryl amine compound Chemical class 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 37
- 150000003624 transition metals Chemical class 0.000 claims abstract description 36
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 35
- 238000005859 coupling reaction Methods 0.000 claims abstract description 24
- 230000008878 coupling Effects 0.000 claims abstract description 23
- 238000010168 coupling process Methods 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 23
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 19
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 17
- 235000019439 ethyl acetate Nutrition 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims description 7
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 235000019798 tripotassium phosphate Nutrition 0.000 claims description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052792 caesium Inorganic materials 0.000 claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical class [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 239000002904 solvent Substances 0.000 description 35
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000005266 diarylamine group Chemical group 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 15
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000003446 ligand Substances 0.000 description 11
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 11
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
- 150000004982 aromatic amines Chemical class 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 102000043136 MAP kinase family Human genes 0.000 description 7
- 108091054455 MAP kinase family Proteins 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 239000003880 polar aprotic solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000002158 endotoxin Substances 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229920006008 lipopolysaccharide Polymers 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- FODOUIXGKGNSMR-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O FODOUIXGKGNSMR-UHFFFAOYSA-L 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 108010002352 Interleukin-1 Proteins 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000006254 arylation reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- QBRORDIPGULCFR-UHFFFAOYSA-N tert-butyl n-(2,6-difluorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=C(F)C=CC=C1F QBRORDIPGULCFR-UHFFFAOYSA-N 0.000 description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000976900 Homo sapiens Mitogen-activated protein kinase 14 Proteins 0.000 description 2
- 108090001005 Interleukin-6 Proteins 0.000 description 2
- 108090001007 Interleukin-8 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 102000054819 Mitogen-activated protein kinase 14 Human genes 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000036755 cellular response Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- JPJLYIZLSBBOKF-UHFFFAOYSA-N ethyl 6-chloro-2-(2,4-difluorophenyl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)N=C1C1=CC=C(F)C=C1F JPJLYIZLSBBOKF-UHFFFAOYSA-N 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- YKJYKKNCCRKFSL-RDBSUJKOSA-N (-)-anisomycin Chemical compound C1=CC(OC)=CC=C1C[C@@H]1[C@H](OC(C)=O)[C@@H](O)CN1 YKJYKKNCCRKFSL-RDBSUJKOSA-N 0.000 description 1
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| PCT/US2004/003933 WO2004072038A1 (en) | 2003-02-10 | 2004-02-10 | Processes for the preparation of n-heteroaryl-n-aryl-amines by reacting an n-aryl carbamic acid ester with a halo-heteroaryl and analogous processes |
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| JP4675318B2 (ja) * | 2003-02-10 | 2011-04-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | N−アリールカルバミン酸エステルとハロ−ヘテロアリールとを反応させることによるn−ヘテロアリール−n−アリール−アミンの調製のためのプロセスおよび類似のプロセス |
| ATE352550T1 (de) | 2003-09-19 | 2007-02-15 | Astrazeneca Ab | Chinazolinderivate |
| BRPI0608910A2 (pt) * | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| JP2008545696A (ja) * | 2005-05-23 | 2008-12-18 | スミスクライン・ビーチャム・コーポレイション | 肥満の処置のためのp38markの阻害 |
| SI1945632T1 (sl) | 2005-11-08 | 2014-03-31 | Vertex Pharmaceuticals Incorporated | Heterocikliäśni modulatorji za prenaĺ alce z atp-vezavno kaseto |
| MX2008011490A (es) * | 2006-03-07 | 2009-01-07 | Vertex Pharma | Composiciones y metodos para tratar artritis reumatoide. |
| AU2007223797A1 (en) * | 2006-03-08 | 2007-09-13 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole derivatives with anti-HCV activity |
| NZ581259A (en) | 2007-05-09 | 2012-07-27 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| BRPI0811939A2 (pt) * | 2007-05-22 | 2014-11-25 | Achillion Pharmaceuticals Inc | Tiazóis substituídos por heteroarila |
| SI2209778T1 (sl) | 2007-09-21 | 2012-12-31 | Array Biopharma, Inc. | Piridin-2-il-amino-I, 2,4-tiadiazol derivati kot aktivatorji glukokinaze za zdravljenje sladkorne bolezni |
| AU2008333845C1 (en) | 2007-12-07 | 2014-01-16 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3] dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| AU2013205160B2 (en) * | 2007-12-07 | 2016-05-19 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| SI2639224T1 (sl) | 2007-12-07 | 2016-12-30 | Vertex Pharmaceuticals Incorporated | Postopek za pripravo cikloalkilkarboksiamido-piridinskih benzojskih kislin |
| CN102245573B (zh) | 2008-02-28 | 2013-11-20 | 沃泰克斯药物股份有限公司 | 作为cftr调节剂的杂芳基衍生物 |
| CN104262267B9 (zh) * | 2008-03-18 | 2019-04-12 | 艾尼纳制药公司 | 用于治疗前列环素(pgi2)受体相关病症的pgi2受体调节剂 |
| US8106209B2 (en) * | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
| US20110224262A1 (en) | 2008-11-26 | 2011-09-15 | Arena Pharmaceuticals, Inc. | Pyrazolyl substituted carbonic acid derivatives as modulators of the prostacyclin (pgi2) receptor useful for the treatment of disorders related thereto |
| PL2370413T3 (pl) | 2008-12-08 | 2016-01-29 | Arena Pharm Inc | Modulatory receptora prostacykliny (PGI2) użyteczne w leczeniu zaburzeń z nimi związanych |
| EP2396302A2 (en) | 2009-02-13 | 2011-12-21 | Vertex Pharmceuticals Incorporated | Processes for producing phenyl-6-(1-(phenyl)ureido)nicotinamides) |
| CN102378756A (zh) | 2009-02-13 | 2012-03-14 | 沃泰克斯药物股份有限公司 | 2-(2,4-二氟苯基)-6-(1-(2,6-二氟苯基)脲基)烟酰胺的固体形式 |
| AU2010218748B2 (en) * | 2009-02-27 | 2015-03-26 | Teijin Limited | Process for producing phenyl-substituted heterocyclic derivative through coupling using transition metal catalyst |
| GB0908317D0 (en) * | 2009-05-14 | 2009-06-24 | Argenta Discovery Ltd | Pharmaceutical compounds and compositions |
| UY33227A (es) | 2010-02-19 | 2011-09-30 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de la cdk4/6 |
| LT3150198T (lt) | 2010-04-07 | 2021-12-10 | Vertex Pharmaceuticals Incorporated | 3-(6-(1-(2,2-difluorbenzo[d][1,3]dioksol-5-il) ciklopropankarboksamido)-3-metilpiridin-2-il)benzoinės rūgšties farmacinė kompozicija ir jos įvedimas |
| CN103068807B (zh) * | 2010-08-27 | 2016-05-25 | 帝人制药株式会社 | 通过使用钯化合物的偶合法的苯基取代杂环衍生物的制备方法 |
| DE102012003281B4 (de) | 2011-02-24 | 2014-02-13 | Tokai Rubber Industries, Ltd. | Berührungsschalter |
| BR112016010403A2 (pt) | 2013-11-12 | 2017-08-08 | Vertex Pharma | Processo de preparação de composições farmacêuticas para o tratamento de doenças mediadas por cftr |
| RU2537848C1 (ru) * | 2013-12-10 | 2015-01-10 | Федеральное государственное казенное учреждение "33 Центральный научно-исследовательский испытательный институт Министерства обороны Российской Федерации" | Способ получения 2-хлор-5-гидроксиметилпиридина |
| EA201790905A1 (ru) | 2014-10-23 | 2017-09-29 | Арена Фармасьютикалз, Инк. | Способ лечения состояний, связанных с рецептором pgi2 |
| CA2968130C (en) | 2014-11-18 | 2022-08-16 | Vertex Pharmaceuticals Incorporated | Process of conducting high throughput testing high performance liquid chromatography |
| KR20230021186A (ko) | 2016-11-10 | 2023-02-13 | 아레나 파마슈티칼스, 인크. | 라리네팍 및 다른 제제의 조합에 의한 pah의 치료 방법 |
| CN110582271B (zh) | 2017-03-01 | 2022-06-14 | 阿瑞那制药公司 | 包含pgi2受体激动剂的组合物及其制备方法 |
| CA3127373A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| EP3796902A1 (en) | 2018-05-16 | 2021-03-31 | Arena Pharmaceuticals, Inc. | Compositions comprising pgi2-receptor agonists and processes for the preparation thereof |
| TW202112368A (zh) | 2019-06-13 | 2021-04-01 | 荷蘭商法西歐知識產權股份有限公司 | 用於治療有關dux4表現之疾病的抑制劑組合 |
| WO2022175752A1 (en) | 2021-02-19 | 2022-08-25 | Sudo Biosciences Limited | Tyk2 inhibitors and uses thereof |
| AU2022222470A1 (en) | 2021-02-19 | 2023-09-21 | Sudo Biosciences Limited | Tyk2 inhibitors and uses thereof |
| WO2023158634A1 (en) | 2022-02-15 | 2023-08-24 | United Therapeutics Corporation | Crystalline prostacyclin (ip) receptor agonist and uses thereof |
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|---|---|---|---|---|
| GB1385474A (en) * | 1971-04-07 | 1975-02-26 | Ici Ltd | Process for reducing the primary amine content of diarylamines |
| NZ302117A (en) | 1995-01-12 | 1999-10-28 | Smithkline Beecham Corp | 1-cycloalkyl or cycloalkylalkyl 4,5-trisubstituted imidazole derivatives and medicaments |
| MY132496A (en) | 1998-05-11 | 2007-10-31 | Vertex Pharma | Inhibitors of p38 |
| AU762245B2 (en) | 1998-09-18 | 2003-06-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| AU8323701A (en) * | 2000-08-11 | 2002-02-25 | John Cochran | Inhibitors of p38 |
| WO2003000189A2 (en) * | 2001-06-21 | 2003-01-03 | Baylor College Of Medicine | Prediction, diagnosis and treatment of endocrine resistant breast cancer, using p38 mapk pathway |
| JP4675318B2 (ja) * | 2003-02-10 | 2011-04-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | N−アリールカルバミン酸エステルとハロ−ヘテロアリールとを反応させることによるn−ヘテロアリール−n−アリール−アミンの調製のためのプロセスおよび類似のプロセス |
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2004
- 2004-02-10 JP JP2006503471A patent/JP4675318B2/ja not_active Expired - Fee Related
- 2004-02-10 WO PCT/US2004/003933 patent/WO2004072038A1/en not_active Ceased
- 2004-02-10 EP EP12193459A patent/EP2562158A1/en not_active Withdrawn
- 2004-02-10 US US10/775,687 patent/US7115746B2/en not_active Expired - Fee Related
- 2004-02-10 CN CN200910252643A patent/CN101723891A/zh active Pending
- 2004-02-10 CA CA2755297A patent/CA2755297A1/en not_active Abandoned
- 2004-02-10 EP EP04709916A patent/EP1603878B1/en not_active Expired - Lifetime
- 2004-02-10 MX MXPA05008450A patent/MXPA05008450A/es active IP Right Grant
- 2004-02-10 NZ NZ542153A patent/NZ542153A/en unknown
- 2004-02-10 KR KR1020057014640A patent/KR20050101200A/ko not_active Ceased
- 2004-02-10 RU RU2005128274/04A patent/RU2351590C2/ru not_active IP Right Cessation
- 2004-02-10 CA CA002515669A patent/CA2515669A1/en not_active Abandoned
- 2004-02-10 AU AU2004212494A patent/AU2004212494B2/en not_active Ceased
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- 2005-09-09 NO NO20054201A patent/NO20054201L/no unknown
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2006
- 2006-08-15 US US11/504,543 patent/US8034950B2/en not_active Expired - Fee Related
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2010
- 2010-11-26 JP JP2010264371A patent/JP2011037908A/ja active Pending
- 2010-11-26 JP JP2010264372A patent/JP2011037909A/ja active Pending
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2011
- 2011-08-24 US US13/216,530 patent/US8686157B2/en not_active Expired - Lifetime
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- 2014-01-22 JP JP2014009078A patent/JP2014133745A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7115746B2 (en) | 2006-10-03 |
| US8686157B2 (en) | 2014-04-01 |
| AU2004212494B2 (en) | 2011-03-17 |
| CA2755297A1 (en) | 2004-08-26 |
| EP1603878B1 (en) | 2013-01-02 |
| US20120157684A1 (en) | 2012-06-21 |
| NO20054201D0 (no) | 2005-09-09 |
| CA2515669A1 (en) | 2004-08-26 |
| JP2014133745A (ja) | 2014-07-24 |
| JP4675318B2 (ja) | 2011-04-20 |
| RU2005128274A (ru) | 2006-01-27 |
| EP2562158A1 (en) | 2013-02-27 |
| HK1087117A1 (zh) | 2006-10-06 |
| KR20050101200A (ko) | 2005-10-20 |
| JP2011037909A (ja) | 2011-02-24 |
| US20040230058A1 (en) | 2004-11-18 |
| RU2351590C2 (ru) | 2009-04-10 |
| US20070173649A1 (en) | 2007-07-26 |
| CN101723891A (zh) | 2010-06-09 |
| MXPA05008450A (es) | 2005-10-18 |
| JP2006517235A (ja) | 2006-07-20 |
| NO20054201L (no) | 2005-10-06 |
| WO2004072038A1 (en) | 2004-08-26 |
| JP2011037908A (ja) | 2011-02-24 |
| EP1603878A1 (en) | 2005-12-14 |
| US8034950B2 (en) | 2011-10-11 |
| AU2004212494A1 (en) | 2004-08-26 |
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