DE60118714T2 - Festphasensynthese und reagentien hierfür - Google Patents
Festphasensynthese und reagentien hierfür Download PDFInfo
- Publication number
- DE60118714T2 DE60118714T2 DE60118714T DE60118714T DE60118714T2 DE 60118714 T2 DE60118714 T2 DE 60118714T2 DE 60118714 T DE60118714 T DE 60118714T DE 60118714 T DE60118714 T DE 60118714T DE 60118714 T2 DE60118714 T2 DE 60118714T2
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- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 46
- 238000010532 solid phase synthesis reaction Methods 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 21
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 9
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 8
- 150000004676 glycans Chemical class 0.000 claims abstract description 4
- 108091033319 polynucleotide Proteins 0.000 claims abstract description 4
- 102000040430 polynucleotide Human genes 0.000 claims abstract description 4
- 239000002157 polynucleotide Substances 0.000 claims abstract description 4
- 229920001184 polypeptide Polymers 0.000 claims abstract description 4
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 4
- 239000005017 polysaccharide Substances 0.000 claims abstract description 4
- 239000010703 silicon Substances 0.000 claims abstract description 4
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 30
- 239000004793 Polystyrene Substances 0.000 claims description 12
- 229920002223 polystyrene Polymers 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- -1 Polypropylene Polymers 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 239000011324 bead Substances 0.000 claims description 5
- 150000001282 organosilanes Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 239000002773 nucleotide Substances 0.000 claims description 3
- 125000003729 nucleotide group Chemical group 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 13
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- 230000003252 repetitive effect Effects 0.000 abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
- 125000000524 functional group Chemical group 0.000 description 26
- 238000007792 addition Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 8
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 8
- 229920002401 polyacrylamide Polymers 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 238000000502 dialysis Methods 0.000 description 7
- VOUNAOIVMLUNHP-JOHDSVJWSA-N n'-[(3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]prop-2-enehydrazide Chemical compound OC[C@H]1OC(O)[C@H](NNC(=O)C=C)[C@@H](O)[C@@H]1O VOUNAOIVMLUNHP-JOHDSVJWSA-N 0.000 description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 229950000688 phenothiazine Drugs 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- 229910052734 helium Inorganic materials 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
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- 238000001228 spectrum Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
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- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000936 Agarose Polymers 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 208000033365 congenital hypomelinating neuropathy Diseases 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
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- 239000007790 solid phase Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RFENWGBCFDTELK-UHFFFAOYSA-N 4-benzoyl-n-[5-[(4-benzoylbenzoyl)amino]-6-oxo-6-(2-sulfanylethylamino)hexyl]benzamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)NCCS)CCCCNC(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 RFENWGBCFDTELK-UHFFFAOYSA-N 0.000 description 2
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 2
- OZCULFZQSHFJNI-UHFFFAOYSA-N 4-benzoylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C1=CC=CC=C1 OZCULFZQSHFJNI-UHFFFAOYSA-N 0.000 description 2
- FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
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- CPGRMGOILBSUQC-UHFFFAOYSA-N phosphoryl azide Chemical class [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-] CPGRMGOILBSUQC-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QLWQBUVPOLBDCD-UHFFFAOYSA-N tert-butyl n-[3-(2-methylprop-2-enoylamino)propyl]carbamate Chemical compound CC(=C)C(=O)NCCCNC(=O)OC(C)(C)C QLWQBUVPOLBDCD-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 235000012431 wafers Nutrition 0.000 description 2
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- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/11—Compounds covalently bound to a solid support
Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Catalysts (AREA)
- Laminated Bodies (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
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| PCT/US2001/003780 WO2001066554A2 (en) | 2000-03-09 | 2001-02-06 | Solid phase synthesis method and reagent |
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| DE60118714D1 DE60118714D1 (de) | 2006-05-24 |
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| MX (1) | MXPA02007445A (enExample) |
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| DE60322000D1 (de) * | 2002-08-16 | 2008-08-21 | Rohm & Haas | Harze mit niedrigem Leerraum und Verfahren zu deren Herstellung |
| EP1394196A1 (en) * | 2002-08-16 | 2004-03-03 | Rohm And Haas Company | Resin for solid phase synthesis |
| US20040063856A1 (en) * | 2002-09-30 | 2004-04-01 | Bohling James Charles | Resin for solid phase synthesis |
| AU2002368411A1 (en) | 2002-11-29 | 2004-06-23 | Marcella Chiari | Method for immobilizing biologic molecules on solid surfaces |
| US20070082019A1 (en) * | 2003-02-21 | 2007-04-12 | Ciphergen Biosystems Inc. | Photocrosslinked hydrogel surface coatings |
| US7309593B2 (en) | 2003-10-01 | 2007-12-18 | Surmodics, Inc. | Attachment of molecules to surfaces |
| WO2005037338A1 (en) * | 2003-10-14 | 2005-04-28 | Cook Incorporated | Hydrophilic coated medical device |
| JP2007525571A (ja) | 2004-01-07 | 2007-09-06 | ソレクサ リミテッド | 修飾分子アレイ |
| US20060018948A1 (en) * | 2004-06-24 | 2006-01-26 | Guire Patrick E | Biodegradable implantable medical devices, methods and systems |
| WO2006002366A2 (en) * | 2004-06-24 | 2006-01-05 | Surmodics, Inc. | Biodegradable ocular devices, methods and systems |
| US20060147847A1 (en) * | 2004-12-30 | 2006-07-06 | Guire Patrick E | Antimicrobial compositions and methods |
| CA2927921C (en) | 2006-01-17 | 2019-06-04 | Transcend Medical, Inc. | Glaucoma treatment device |
| US8968396B2 (en) | 2007-07-23 | 2015-03-03 | Powervision, Inc. | Intraocular lens delivery systems and methods of use |
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-
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- 2000-03-09 US US09/521,552 patent/US6410643B1/en not_active Expired - Lifetime
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2001
- 2001-02-06 EP EP01907009A patent/EP1268505B1/en not_active Expired - Lifetime
- 2001-02-06 JP JP2001565370A patent/JP5048193B2/ja not_active Expired - Lifetime
- 2001-02-06 CA CA2399043A patent/CA2399043C/en not_active Expired - Fee Related
- 2001-02-06 AT AT01907009T patent/ATE323098T1/de not_active IP Right Cessation
- 2001-02-06 WO PCT/US2001/003780 patent/WO2001066554A2/en not_active Ceased
- 2001-02-06 DE DE60118714T patent/DE60118714T2/de not_active Expired - Lifetime
- 2001-02-06 MX MXPA02007445A patent/MXPA02007445A/es unknown
- 2001-02-06 AU AU34845/01A patent/AU3484501A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE323098T1 (de) | 2006-04-15 |
| US6410643B1 (en) | 2002-06-25 |
| JP2003525945A (ja) | 2003-09-02 |
| EP1268505A2 (en) | 2003-01-02 |
| AU3484501A (en) | 2001-09-17 |
| CA2399043A1 (en) | 2001-09-13 |
| MXPA02007445A (es) | 2003-01-28 |
| WO2001066554A3 (en) | 2002-03-14 |
| WO2001066554A2 (en) | 2001-09-13 |
| DE60118714D1 (de) | 2006-05-24 |
| JP5048193B2 (ja) | 2012-10-17 |
| CA2399043C (en) | 2012-07-17 |
| EP1268505B1 (en) | 2006-04-12 |
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