ES2382863T3 - Copolímeros de amina cuaternaria-siloxano polimerizables - Google Patents
Copolímeros de amina cuaternaria-siloxano polimerizables Download PDFInfo
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- ES2382863T3 ES2382863T3 ES07798170T ES07798170T ES2382863T3 ES 2382863 T3 ES2382863 T3 ES 2382863T3 ES 07798170 T ES07798170 T ES 07798170T ES 07798170 T ES07798170 T ES 07798170T ES 2382863 T3 ES2382863 T3 ES 2382863T3
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- ether
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- 229920001577 copolymer Polymers 0.000 title description 5
- 239000000178 monomer Substances 0.000 claims abstract description 92
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- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000000017 hydrogel Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical class CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 9
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000005215 alkyl ethers Chemical class 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 150000008378 aryl ethers Chemical class 0.000 claims description 5
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 4
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- 239000011737 fluorine Substances 0.000 claims description 4
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- 239000007943 implant Substances 0.000 claims description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 4
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000012620 biological material Substances 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
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- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003673 urethanes Chemical class 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
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- 210000000481 breast Anatomy 0.000 claims description 2
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- 238000000502 dialysis Methods 0.000 claims description 2
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- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical class CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 210000000626 ureter Anatomy 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 29
- 229910052710 silicon Inorganic materials 0.000 abstract description 29
- 239000010703 silicon Substances 0.000 abstract description 29
- 125000002091 cationic group Chemical group 0.000 abstract description 14
- 229920000642 polymer Polymers 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 description 26
- 229910052760 oxygen Inorganic materials 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 12
- 230000035699 permeability Effects 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 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 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 125000004446 heteroarylalkyl group Chemical group 0.000 description 4
- 238000003754 machining Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000001425 electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 238000001542 size-exclusion chromatography Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- APUATYFVVUNQRY-UHFFFAOYSA-N 2-butoxy-n,n-dimethylethanamine Chemical compound CCCCOCCN(C)C APUATYFVVUNQRY-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 101800004538 Bradykinin Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 2
- 102100035792 Kininogen-1 Human genes 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000000732 arylene group Chemical group 0.000 description 2
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- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 1
- IEPUABWMJBVAAN-UHFFFAOYSA-N 2-[4-[[4-[4-[2-(2-methylprop-2-enoyloxy)ethyl]anilino]-9,10-dioxoanthracen-1-yl]amino]phenyl]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(CCOC(=O)C(C)=C)C=C1 IEPUABWMJBVAAN-UHFFFAOYSA-N 0.000 description 1
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- BYBORNQRJVLEFV-UHFFFAOYSA-N 4-bromobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCBr BYBORNQRJVLEFV-UHFFFAOYSA-N 0.000 description 1
- RNKKXFZNHLXTNG-UHFFFAOYSA-N 4-bromobutyl-[4-bromobutyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound BrCCCC[Si](C)(C)O[Si](C)(C)CCCCBr RNKKXFZNHLXTNG-UHFFFAOYSA-N 0.000 description 1
- 125000005986 4-piperidonyl group Chemical group 0.000 description 1
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- 241001486234 Sciota Species 0.000 description 1
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- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
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- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Optics & Photonics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
- Silicon Polymers (AREA)
- Prostheses (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
- External Artificial Organs (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| PCT/US2007/070509 WO2008005644A1 (en) | 2006-06-30 | 2007-06-06 | Polymerizable siloxane-quaternary amine copolymers |
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| US20030032874A1 (en) * | 2001-07-27 | 2003-02-13 | Dexcom, Inc. | Sensor head for use with implantable devices |
| WO2005011520A2 (en) | 2003-07-25 | 2005-02-10 | Dexcom, Inc. | Oxygen enhancing membrane systems for implantable devices |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| US8277713B2 (en) * | 2004-05-03 | 2012-10-02 | Dexcom, Inc. | Implantable analyte sensor |
| US7946984B2 (en) | 2004-07-13 | 2011-05-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| US20070045902A1 (en) | 2004-07-13 | 2007-03-01 | Brauker James H | Analyte sensor |
| US8744546B2 (en) | 2005-05-05 | 2014-06-03 | Dexcom, Inc. | Cellulosic-based resistance domain for an analyte sensor |
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| US7759408B2 (en) * | 2005-12-21 | 2010-07-20 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
| US8828420B2 (en) * | 2006-01-06 | 2014-09-09 | Bausch & Lomb Incorporated | Siloxane prepolymer containing pendant cationic and polymerizable groups |
| US7825273B2 (en) * | 2006-01-06 | 2010-11-02 | Bausch & Lomb Incorporated | Process for making cationic hydrophilic siloxanyl monomers |
| US7960447B2 (en) | 2006-04-13 | 2011-06-14 | Bausch & Lomb Incorporated | Cationic end-capped siloxane prepolymer for reduced cross-link density |
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| US7579021B2 (en) * | 2006-09-27 | 2009-08-25 | Bausch & Lomb Incorporated | Drug delivery systems based on degradable cationic siloxanyl macromonomers |
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| US7951897B2 (en) | 2007-01-26 | 2011-05-31 | Bausch & Lomb Incorporated | Synthesis of cationic siloxane prepolymers |
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| US11730407B2 (en) | 2008-03-28 | 2023-08-22 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| EP2257794B1 (en) * | 2008-03-28 | 2018-05-09 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8682408B2 (en) | 2008-03-28 | 2014-03-25 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8583204B2 (en) | 2008-03-28 | 2013-11-12 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8093352B2 (en) * | 2008-08-05 | 2012-01-10 | Alcon Research, Ltd. | Polyalkylene oxide polyquaternary ammonium biocides |
| WO2010033724A2 (en) | 2008-09-19 | 2010-03-25 | Dexcom, Inc. | Particle-containing membrane and particulate electrode for analyte sensors |
| US20110212994A1 (en) | 2009-06-26 | 2011-09-01 | Brian Clem | Small Molecule Choline Kinase Inhibitors, Screening Assays, and Methods for Safe and Effective Treatment of Neoplastic Disorders |
| CA2802486C (en) | 2010-07-30 | 2015-01-06 | Novartis Ag | Amphiphilic polysiloxane prepolymers and uses thereof |
| EP2625217B1 (en) | 2010-10-06 | 2018-07-04 | Novartis AG | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| JP5852659B2 (ja) | 2010-10-06 | 2016-02-03 | ノバルティス アーゲー | 水処理可能なシリコーン含有プレポリマー及びその使用 |
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| US10118994B2 (en) | 2013-01-31 | 2018-11-06 | Momentive Performance Materials Inc. | Water soluble silicone material |
| US9486311B2 (en) | 2013-02-14 | 2016-11-08 | Shifamed Holdings, Llc | Hydrophilic AIOL with bonding |
| EP4257359A3 (en) | 2013-03-21 | 2023-12-06 | Shifamed Holdings, LLC | Accommodating intraocular lens |
| US10195018B2 (en) | 2013-03-21 | 2019-02-05 | Shifamed Holdings, Llc | Accommodating intraocular lens |
| CN107106293B (zh) | 2014-08-26 | 2019-07-12 | 施菲姆德控股有限责任公司 | 调节性人工晶状体 |
| US9976974B2 (en) * | 2015-01-27 | 2018-05-22 | University Of Utah Research Foundation | Osmolarity-responsive hydrogel sensors and method of use |
| CA3005338A1 (en) | 2015-11-18 | 2017-05-26 | Shifamed Holdings, Llc | Multi-piece accommodating intraocular lens |
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| CN110494519B (zh) * | 2017-02-16 | 2021-10-26 | 莫门蒂夫性能材料股份有限公司 | 经离子改性的有机硅、组合物和由其形成的医疗器材 |
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| EP3634309B1 (en) | 2017-06-07 | 2023-05-24 | Shifamed Holdings, LLC | Adjustable optical power intraocular lenses |
| CN119998361A (zh) * | 2022-06-02 | 2025-05-13 | 迈图高新材料公司 | 聚硅氧烷聚合物组合物及其制备方法 |
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-
2006
- 2006-06-30 US US11/479,608 patent/US7468397B2/en not_active Expired - Fee Related
-
2007
- 2007-06-06 EP EP07798170A patent/EP2035486B1/en not_active Not-in-force
- 2007-06-06 WO PCT/US2007/070509 patent/WO2008005644A1/en not_active Ceased
- 2007-06-06 ES ES11177006T patent/ES2428273T3/es active Active
- 2007-06-06 CN CN200780023604.6A patent/CN101479325B/zh not_active Expired - Fee Related
- 2007-06-06 AT AT07798170T patent/ATE555150T1/de active
- 2007-06-06 JP JP2009518430A patent/JP5519277B2/ja not_active Expired - Fee Related
- 2007-06-06 ES ES07798170T patent/ES2382863T3/es active Active
- 2007-06-06 CA CA002652075A patent/CA2652075A1/en not_active Abandoned
- 2007-06-06 BR BRPI0712367-1A patent/BRPI0712367A2/pt not_active Application Discontinuation
- 2007-06-06 EP EP11177006.1A patent/EP2404951B1/en not_active Not-in-force
-
2008
- 2008-11-18 US US12/313,253 patent/US20090143556A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| HK1127621A1 (en) | 2009-10-02 |
| BRPI0712367A2 (pt) | 2012-06-05 |
| HK1164348A1 (en) | 2012-09-21 |
| ES2428273T3 (es) | 2013-11-06 |
| CN101479325B (zh) | 2013-06-26 |
| EP2035486A1 (en) | 2009-03-18 |
| JP5519277B2 (ja) | 2014-06-11 |
| EP2404951A1 (en) | 2012-01-11 |
| EP2404951B1 (en) | 2013-09-11 |
| US20090143556A1 (en) | 2009-06-04 |
| US7468397B2 (en) | 2008-12-23 |
| US20080001318A1 (en) | 2008-01-03 |
| JP2009542855A (ja) | 2009-12-03 |
| EP2035486B1 (en) | 2012-04-25 |
| CN101479325A (zh) | 2009-07-08 |
| ATE555150T1 (de) | 2012-05-15 |
| CA2652075A1 (en) | 2008-01-10 |
| WO2008005644A1 (en) | 2008-01-10 |
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