HRP20040148A2 - Solid compositions for selective adsorption from complex mixtures - Google Patents
Solid compositions for selective adsorption from complex mixtures Download PDFInfo
- Publication number
- HRP20040148A2 HRP20040148A2 HR20040148A HRP20040148A HRP20040148A2 HR P20040148 A2 HRP20040148 A2 HR P20040148A2 HR 20040148 A HR20040148 A HR 20040148A HR P20040148 A HRP20040148 A HR P20040148A HR P20040148 A2 HRP20040148 A2 HR P20040148A2
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- Prior art keywords
- substituted
- group
- solid
- inorganic substance
- binding
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 58
- 239000008247 solid mixture Substances 0.000 title 1
- 238000001179 sorption measurement Methods 0.000 title 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 181
- 239000000126 substance Substances 0.000 claims description 108
- 239000007787 solid Substances 0.000 claims description 86
- 239000000377 silicon dioxide Substances 0.000 claims description 82
- 230000027455 binding Effects 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 76
- -1 zirconate Chemical compound 0.000 claims description 58
- 239000012491 analyte Substances 0.000 claims description 54
- 108090000623 proteins and genes Proteins 0.000 claims description 52
- 102000004169 proteins and genes Human genes 0.000 claims description 52
- 239000011230 binding agent Substances 0.000 claims description 43
- 125000005647 linker group Chemical group 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910044991 metal oxide Inorganic materials 0.000 claims description 21
- 150000004706 metal oxides Chemical class 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000003636 chemical group Chemical group 0.000 claims description 15
- 229910002027 silica gel Inorganic materials 0.000 claims description 15
- 239000000741 silica gel Substances 0.000 claims description 15
- 230000009871 nonspecific binding Effects 0.000 claims description 14
- 239000011148 porous material Substances 0.000 claims description 14
- 239000000376 reactant Substances 0.000 claims description 14
- 235000012239 silicon dioxide Nutrition 0.000 claims description 14
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 12
- 238000002955 isolation Methods 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 229960002685 biotin Drugs 0.000 claims description 6
- 235000020958 biotin Nutrition 0.000 claims description 6
- 239000011616 biotin Substances 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 6
- 108090001008 Avidin Proteins 0.000 claims description 5
- 108010090804 Streptavidin Proteins 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 5
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 5
- 239000000427 antigen Substances 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910052914 metal silicate Inorganic materials 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 150000007970 thio esters Chemical class 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 108020004707 nucleic acids Proteins 0.000 claims description 2
- 102000039446 nucleic acids Human genes 0.000 claims description 2
- 150000007523 nucleic acids Chemical class 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 4
- 230000004913 activation Effects 0.000 claims 4
- CXCHEKCRJQRVNG-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonyl chloride Chemical compound FC(F)(F)CS(Cl)(=O)=O CXCHEKCRJQRVNG-UHFFFAOYSA-N 0.000 claims 2
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims 2
- AMGZELLFFNISNA-UHFFFAOYSA-N 2-fluoro-1-methyl-2h-pyridine;4-methylbenzenesulfonic acid Chemical compound CN1C=CC=CC1F.CC1=CC=C(S(O)(=O)=O)C=C1 AMGZELLFFNISNA-UHFFFAOYSA-N 0.000 claims 2
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 claims 2
- 238000010976 amide bond formation reaction Methods 0.000 claims 2
- 238000005576 amination reaction Methods 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims 2
- 239000012954 diazonium Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- ORRXNPKJTGGJNV-UHFFFAOYSA-N n-ethyl-n'-(3-methylbutyl)methanediimine Chemical compound CCN=C=NCCC(C)C ORRXNPKJTGGJNV-UHFFFAOYSA-N 0.000 claims 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 2
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000000523 sample Substances 0.000 description 40
- 238000000926 separation method Methods 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 24
- 230000003993 interaction Effects 0.000 description 20
- 125000004429 atom Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000872 buffer Substances 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 238000001155 isoelectric focusing Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 241000894007 species Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 8
- 125000001769 aryl amino group Chemical group 0.000 description 8
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 8
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000004663 dialkyl amino group Chemical group 0.000 description 8
- 125000004986 diarylamino group Chemical group 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000005504 styryl group Chemical group 0.000 description 8
- 125000003441 thioacyl group Chemical group 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 7
- 230000004151 fermentation Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 125000005372 silanol group Chemical group 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 5
- 238000004113 cell culture Methods 0.000 description 5
- 239000003550 marker Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001502 gel electrophoresis Methods 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910003849 O-Si Inorganic materials 0.000 description 3
- 229910003872 O—Si Inorganic materials 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 3
- 238000001261 affinity purification Methods 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 101710120037 Toxin CcdB Proteins 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000001042 affinity chromatography Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000009881 electrostatic interaction Effects 0.000 description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000005660 hydrophilic surface Effects 0.000 description 2
- 230000005661 hydrophobic surface Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000006249 magnetic particle Substances 0.000 description 2
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Classifications
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/288—Polar phases
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
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| PCT/US2002/025351 WO2003015915A1 (en) | 2001-08-14 | 2002-08-12 | Solid compositions for selective adsorption from complex mixtures |
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Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6987079B2 (en) * | 2001-08-14 | 2006-01-17 | W.R. Grace & Co.-Conn. | Supported catalyst systems |
| US8137548B2 (en) * | 2003-10-17 | 2012-03-20 | Zirchrom Separations, Inc. | Chelator-modified inorganic oxide particles |
| EP1538481A1 (en) * | 2003-12-05 | 2005-06-08 | Sony International (Europe) GmbH | A method of activating a silicon surface for subsequent patterning of molecules onto said surface |
| WO2005089911A1 (en) * | 2004-03-17 | 2005-09-29 | Ciphergen Biosystems, Inc. | Materials, methods, and systems for separating and identifying proteins from mixtures |
| BRPI0513526A (pt) * | 2004-07-19 | 2008-05-06 | Grace Gmbh & Co Kg | componentes de aparelho e métodos de utilizar componentes de aparelho para detectar a presença de um analisado |
| TW200739068A (en) | 2005-09-29 | 2007-10-16 | Alltech Associates Inc | Composite chromatography column |
| EP2137533A2 (en) * | 2007-04-19 | 2009-12-30 | 3M Innovative Properties Company | Uses of water-dispersible silica nanoparticles for attaching biomolecules |
| WO2008131063A1 (en) * | 2007-04-19 | 2008-10-30 | 3M Innovative Properties Company | Methods of use of solid support material for binding biomolecules |
| US20090004231A1 (en) | 2007-06-30 | 2009-01-01 | Popp Shane M | Pharmaceutical dosage forms fabricated with nanomaterials for quality monitoring |
| ES2319063B1 (es) * | 2007-09-28 | 2010-02-12 | Universidad De Granada | Compuesto de silica-vinilsulfona, sintesis y usos del mismo. |
| JP5620902B2 (ja) * | 2009-03-12 | 2014-11-05 | 株式会社 資生堂 | 充填剤の製造方法、充填剤及びカラム |
| US11628381B2 (en) | 2012-09-17 | 2023-04-18 | W.R. Grace & Co. Conn. | Chromatography media and devices |
| JP6853670B2 (ja) | 2014-01-16 | 2021-04-07 | ダブリュー・アール・グレース・アンド・カンパニー−コーンＷ Ｒ Ｇｒａｃｅ ＆ Ｃｏ−Ｃｏｎｎ | 親和性クロマトグラフィー媒体及びクロマトグラフィーデバイス |
| ES2929099T3 (es) | 2014-05-02 | 2022-11-24 | Grace W R & Co | Material de soporte funcionalizado y métodos de fabricación y uso de material de soporte funcionalizado |
| JP2018517559A (ja) | 2015-06-05 | 2018-07-05 | ダブリュー・アール・グレース・アンド・カンパニー−コーンＷ Ｒ Ｇｒａｃｅ ＆ Ｃｏ−Ｃｏｎｎ | 吸着性バイオプロセス清澄化剤並びにその製造及び使用方法 |
| CN110152630B (zh) * | 2019-06-04 | 2022-03-22 | 南京信息工程大学 | 一种高效吸附剂及其应用 |
| WO2021153717A1 (ja) * | 2020-01-31 | 2021-08-05 | 池田 壽文 | 人工核酸に基づくアフィニティークロマトグラフィー |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3715278A (en) | 1970-02-11 | 1973-02-06 | Monsanto Co | Enzyme-polymer product attached to surface of siliceous materials thereof |
| US3669841A (en) | 1970-02-11 | 1972-06-13 | Monsanto Co | Attachment of enzymes to siliceous materials |
| US3795313A (en) * | 1970-05-22 | 1974-03-05 | Du Pont | Chromatographic packing with chemically bonded organic stationary phases |
| US3666530A (en) * | 1970-10-22 | 1972-05-30 | Research Corp | Novel silicious silicone bonded materials |
| US3873426A (en) | 1973-07-02 | 1975-03-25 | Miles Lab | Insoluble enzymes |
| US3983299A (en) * | 1974-03-04 | 1976-09-28 | Purdue Research Foundation | Bonded carbohydrate stationary phases for chromatography |
| FR2267992A1 (es) | 1974-04-19 | 1975-11-14 | Rhone Poulenc Ind | |
| GB1514707A (en) | 1974-06-25 | 1978-06-21 | Atomic Energy Authority Uk | Immobilization of biologically active substances |
| US3954678A (en) | 1974-07-11 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Semipermeable microcapsules containing a silica gel |
| US4043905A (en) * | 1974-08-26 | 1977-08-23 | Indiana University Foundation | Chromatographic separation columns with selectively modified active surfaces and methods for their preparations |
| US4029583A (en) * | 1975-02-28 | 1977-06-14 | Purdue Research Foundation | Chromatographic supports and methods and apparatus for preparing the same |
| US3983000A (en) | 1976-04-01 | 1976-09-28 | Corning Glass Works | Bonding proteins to inorganic supports |
| DE2621974A1 (de) * | 1976-05-18 | 1977-11-24 | Max Planck Gesellschaft | Verfahren zur herstellung eines zur kovalenten bindung mit biologisch aktivem material befaehigten traegermaterials |
| EP0003923B1 (fr) | 1978-02-16 | 1982-10-20 | Rhone-Poulenc Specialites Chimiques | Complexes support-enzyme et leur procédé de préparation |
| US4206259A (en) | 1978-10-16 | 1980-06-03 | Uop Inc. | Support matrices for immobilized enzymes |
| US4268423A (en) | 1979-11-16 | 1981-05-19 | Uop Inc. | Support matrices for immobilized enzymes |
| US4430496A (en) | 1980-01-17 | 1984-02-07 | Varian Associates, Inc. | Strong anion exchange composition and methods |
| US4298500A (en) * | 1980-05-05 | 1981-11-03 | Varian Associates, Inc. | Mixed phase chromatographic compositions |
| CA1130228A (en) | 1980-05-21 | 1982-08-24 | Chiang-Chang Liao | Support matrix for amino-containing biologically active substances |
| ZA827728B (en) | 1981-11-17 | 1983-08-31 | Nestle Sa | A process for the production of enzymatically active biocatalysts and the products obtained |
| US4415663A (en) | 1982-08-25 | 1983-11-15 | Uop Inc. | Support matrix for immobilized enzymes |
| US4540586A (en) * | 1983-07-01 | 1985-09-10 | Moore William P | Method of preserving fodders with a nutritive coating |
| US4540486A (en) | 1983-11-25 | 1985-09-10 | J. T. Baker Chemical Company | Polyethylenimine bound chromatographic packing |
| US4469630A (en) | 1983-11-25 | 1984-09-04 | J. T. Baker Chemical Co. | Purification of monoclonal antibodies |
| DE3342870A1 (de) | 1983-11-26 | 1985-06-05 | Boehringer Mannheim Gmbh, 6800 Mannheim | Digitalis-antikoerper, verfahren zu ihrer herstellung und ihre verwendung zur therapie von digitalis-intoxikationen |
| US4520122A (en) | 1983-12-05 | 1985-05-28 | Uop Inc. | Immobilization of organic species on refractory inorganic oxides |
| US5110784A (en) * | 1984-04-09 | 1992-05-05 | Dow Corning Corporation | Dual surface porous material |
| US4544485A (en) * | 1984-08-31 | 1985-10-01 | Purdue Research Foundation | Chromatographic method and means |
| US5167812A (en) * | 1984-11-28 | 1992-12-01 | Trustees Of The Univ. Of Penna. | Affinity chromatogry using dried calcium alginate-magnetite separation media in a magnetically stabilized fluidized bed |
| US4681870A (en) | 1985-01-11 | 1987-07-21 | Imre Corporation | Protein A-silica immunoadsorbent and process for its production |
| US4606825A (en) | 1985-04-22 | 1986-08-19 | J. T. Baker Chemical Company | Purification of immunoglobulin G |
| US4551245A (en) | 1985-04-22 | 1985-11-05 | J. T. Baker Chemical Co. | Acylated polyethylenimine bound chromatographic packing |
| CH663728A5 (fr) | 1985-06-10 | 1988-01-15 | Battelle Memorial Institute | Procede de purification de substances bioactives par adsorption biospecifique. |
| US4837348A (en) | 1986-04-30 | 1989-06-06 | Varian Associates, Inc. | Bonded phase chromatographic supports |
| US4994429A (en) | 1986-12-29 | 1991-02-19 | Aluminum Company Of America | Active material useful as adsorbent comprising metal oxide/hydroxide particles reacted with phosphorus-containing organic acid group of organic compound having unreacted acid group |
| JP2509542B2 (ja) * | 1987-02-26 | 1996-06-19 | 株式会社ワイエムシィ | 溶質分離用担体 |
| CA1320718C (en) * | 1987-06-08 | 1993-07-27 | Richard Frederick Hammen | Chromatographic material |
| US5240602A (en) | 1987-06-08 | 1993-08-31 | Chromatochem, Inc. | Chromatographic material |
| US6251278B1 (en) | 1987-06-08 | 2001-06-26 | Chromatochem, Inc. | Process for separating a substance from a mixture |
| US4778600A (en) | 1987-06-17 | 1988-10-18 | Dow Corning Corporation | Liquid chromatography dual zone packing materials |
| EP0303406A3 (en) | 1987-08-14 | 1991-07-03 | Hewlett-Packard Company | An immunoaffinity substrate |
| US5118796A (en) | 1987-12-09 | 1992-06-02 | Centocor, Incorporated | Efficient large-scale purification of immunoglobulins and derivatives |
| JPH01181790A (ja) | 1988-01-18 | 1989-07-19 | Toray Silicone Co Ltd | 生理活性物質の固定化方法 |
| US5277813A (en) | 1988-06-17 | 1994-01-11 | S.A.C. Corporation | Shielded stationary phases |
| ES2058538T3 (es) | 1988-07-22 | 1994-11-01 | Imre Corp | Compuestos de proteina a purificados y procedimiento para su preparacion. |
| US5045190A (en) * | 1988-11-08 | 1991-09-03 | Carbonell Ruben G | Chromatography apparatus |
| US5077210A (en) | 1989-01-13 | 1991-12-31 | Eigler Frances S | Immobilization of active agents on substrates with a silane and heterobifunctional crosslinking agent |
| US5035803A (en) | 1989-02-14 | 1991-07-30 | The Regents Of The University Of California | High yield water-soluble polymer silica separation resins |
| US5043062A (en) * | 1989-02-21 | 1991-08-27 | Eastman Kodak Company | High performance affinity chromatography column comprising non-porous, nondisperse polymeric packing material |
| EP0386926A3 (en) | 1989-03-02 | 1991-12-18 | Supelco, Inc. | Silica gel supports suitable for chromatographic separations |
| US5085779A (en) | 1989-06-07 | 1992-02-04 | J. T. Baker, Inc. | Polyethyleneimine matrixes for affinity chromatography |
| US5055194A (en) * | 1989-07-28 | 1991-10-08 | University Of Pennsylvania | Support for high performance liquid chromatography in a magnetically stabilized fluidized bed |
| JPH03218458A (ja) | 1989-10-02 | 1991-09-26 | Shiseido Co Ltd | カラム充填剤及びその製造方法 |
| US5457195A (en) | 1989-12-21 | 1995-10-10 | Board Of Regents, The University Of Texas System | Sapphyrin derivatives and conjugates |
| US5403750A (en) | 1991-03-06 | 1995-04-04 | W. R. Grace & Co.-Conn. | Biocompatible, low protein adsorption affinity matrix |
| DE4130475A1 (de) * | 1991-09-13 | 1993-03-18 | Merck Patent Gmbh | Modifizierte chromatographische traegermaterialien |
| CA2064683A1 (en) | 1992-03-26 | 1993-09-27 | Krishna Mohan Rao Kallury | Formation of thermostable enzymes with extra-ordinary heat tolerance by immobilization on phospholipid matrices |
| US5906734A (en) | 1992-06-19 | 1999-05-25 | Biosepra Inc. | Passivated porous polymer supports and methods for the preparation and use of same |
| US5374755A (en) | 1992-07-17 | 1994-12-20 | Millipore Corporation | Liquid chromatography stationary phases with reduced silanol interactions |
| US5362859A (en) | 1992-07-27 | 1994-11-08 | Sepracor, Inc. | High-capacity affinity supports and methods for the preparation and use of same |
| US5316680A (en) | 1992-10-21 | 1994-05-31 | Cornell Research Foundation, Inc. | Multimodal chromatographic separation media and process for using same |
| US5371262A (en) | 1993-03-10 | 1994-12-06 | Gelest, Inc. | Hydroxymethyltrialkoxysilanes and methods of making and using the same |
| US5406766A (en) * | 1993-07-29 | 1995-04-18 | Monier Roof Tile Inc. | Multi-color concrete tiles and method and apparatus for making same |
| DE4334353A1 (de) * | 1993-10-08 | 1995-04-13 | Merck Patent Gmbh | Verfahren und Träger für die Gelpermeationschromatographie |
| US5527711A (en) | 1993-12-13 | 1996-06-18 | Hewlett Packard Company | Method and reagents for binding chemical analytes to a substrate surface, and related analytical devices and diagnostic techniques |
| JP3333309B2 (ja) | 1994-04-08 | 2002-10-15 | 鐘淵化学工業株式会社 | ケトアミン含有タンパク質吸着体 |
| US5663051A (en) | 1994-08-31 | 1997-09-02 | Activated Cell Therapy, Inc. | Separation apparatus and method |
| US5652348A (en) | 1994-09-23 | 1997-07-29 | Massey University | Chromatographic resins and methods for using same |
| US6025129A (en) | 1995-04-25 | 2000-02-15 | Irori | Remotely programmable matrices with memories and uses thereof |
| US6048964A (en) | 1995-12-12 | 2000-04-11 | Stryker Corporation | Compositions and therapeutic methods using morphogenic proteins and stimulatory factors |
| US5667674A (en) * | 1996-01-11 | 1997-09-16 | Minnesota Mining And Manufacturing Company | Adsorption medium and method of preparing same |
| US6013855A (en) | 1996-08-06 | 2000-01-11 | United States Surgical | Grafting of biocompatible hydrophilic polymers onto inorganic and metal surfaces |
| DE69810080T2 (de) | 1997-01-21 | 2003-10-09 | Grace W R & Co | Siliciumdioxidadsorbent auf magnetischem träger |
| US5998183A (en) | 1997-07-07 | 1999-12-07 | Le Fevre; Gerard N. | Enzyme immobilization on a siliceous support with a polyaldehyde cross-linking agent |
| US5993653C1 (en) | 1997-08-11 | 2001-11-06 | Phenomenex | Composition and column used in hplc |
| FR2777355B1 (fr) * | 1998-04-10 | 2000-05-12 | Bio Merieux | Procede de fixation d'une molecule biologique sur la surface d'un support constitue de silice ou d'oxyde metallique |
| DE10022529A1 (de) | 2000-05-09 | 2001-11-15 | Emtec Magnetics Gmbh | Pigmenthaltiges Aufzeichnungsmaterial |
| US6987079B2 (en) * | 2001-08-14 | 2006-01-17 | W.R. Grace & Co.-Conn. | Supported catalyst systems |
| US6375846B1 (en) * | 2001-11-01 | 2002-04-23 | Harry Wellington Jarrett | Cyanogen bromide-activation of hydroxyls on silica for high pressure affinity chromatography |
-
2001
- 2001-08-14 US US09/929,621 patent/US6802966B2/en not_active Expired - Fee Related
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2002
- 2002-08-12 JP JP2003520463A patent/JP4235547B2/ja not_active Expired - Fee Related
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- 2002-08-12 IL IL16032102A patent/IL160321A0/xx active IP Right Grant
- 2002-08-12 EP EP02794863A patent/EP1423191B1/en not_active Expired - Lifetime
- 2002-08-12 AU AU2002355940A patent/AU2002355940B2/en not_active Ceased
- 2002-08-12 WO PCT/US2002/025351 patent/WO2003015915A1/en active Application Filing
- 2002-08-12 PL PL02367789A patent/PL367789A1/xx not_active Application Discontinuation
- 2002-08-12 EA EA200400310A patent/EA006059B1/ru not_active IP Right Cessation
- 2002-08-12 MX MXPA04001366A patent/MXPA04001366A/es active IP Right Grant
- 2002-08-12 CA CA002457730A patent/CA2457730A1/en not_active Abandoned
- 2002-08-12 BR BR0211927-7A patent/BR0211927A/pt not_active Application Discontinuation
- 2002-08-12 CN CNB028203267A patent/CN100374197C/zh not_active Expired - Fee Related
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- 2004-02-13 NO NO20040652A patent/NO20040652L/no not_active Application Discontinuation
- 2004-02-13 ZA ZA200401183A patent/ZA200401183B/en unknown
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- 2004-07-16 US US10/892,779 patent/US6998042B2/en not_active Expired - Fee Related
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2005
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Also Published As
| Publication number | Publication date |
|---|---|
| EA006059B1 (ru) | 2005-08-25 |
| US6802966B2 (en) | 2004-10-12 |
| US20050003428A1 (en) | 2005-01-06 |
| EP1423191A1 (en) | 2004-06-02 |
| CN100374197C (zh) | 2008-03-12 |
| NO20040652L (no) | 2004-05-14 |
| US20030042203A1 (en) | 2003-03-06 |
| BR0211927A (pt) | 2004-10-26 |
| US6998042B2 (en) | 2006-02-14 |
| MXPA04001366A (es) | 2004-05-27 |
| WO2003015915A1 (en) | 2003-02-27 |
| US7166213B2 (en) | 2007-01-23 |
| JP4235547B2 (ja) | 2009-03-11 |
| US20060011549A1 (en) | 2006-01-19 |
| IL160321A (en) | 2007-05-15 |
| CN1568222A (zh) | 2005-01-19 |
| ZA200401183B (en) | 2004-08-26 |
| AU2002355940B2 (en) | 2008-10-16 |
| KR100955124B1 (ko) | 2010-04-28 |
| KR20040023751A (ko) | 2004-03-18 |
| JP2004538479A (ja) | 2004-12-24 |
| EP1423191B1 (en) | 2013-03-20 |
| EA200400310A1 (ru) | 2004-08-26 |
| CA2457730A1 (en) | 2003-02-27 |
| IL160321A0 (en) | 2004-07-25 |
| PL367789A1 (en) | 2005-03-07 |
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