CA2391817C - Biomedical compositions - Google Patents
Biomedical compositions Download PDFInfo
- Publication number
- CA2391817C CA2391817C CA2391817A CA2391817A CA2391817C CA 2391817 C CA2391817 C CA 2391817C CA 2391817 A CA2391817 A CA 2391817A CA 2391817 A CA2391817 A CA 2391817A CA 2391817 C CA2391817 C CA 2391817C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- ethylenically unsaturated
- macromonomer
- range
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- -1 polydimethyl-aminopropylsiloxane copolymer Polymers 0.000 claims description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 201000010041 presbyopia Diseases 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- QKPKBBFSFQAMIY-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=C(C=C)OC1=O QKPKBBFSFQAMIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 229920001400 block copolymer Polymers 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 17
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 238000002347 injection Methods 0.000 abstract description 4
- 239000007924 injection Substances 0.000 abstract description 4
- 210000000695 crystalline len Anatomy 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 14
- 239000002775 capsule Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 230000007423 decrease Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002350 accommodative effect Effects 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000000560 biocompatible material Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- QRWAIZJYJNLOPG-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)C1=CC=CC=C1 QRWAIZJYJNLOPG-UHFFFAOYSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- NQPFSLCGTDFWAW-UHFFFAOYSA-N CC(C)C1=CC=C(CC(C)(O)C(=O)C(C)(C)O)C=C1 Chemical compound CC(C)C1=CC=C(CC(C)(O)C(=O)C(C)(C)O)C=C1 NQPFSLCGTDFWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HLJYBXJFKDDIBI-UHFFFAOYSA-N O=[PH2]C(=O)C1=CC=CC=C1 Chemical class O=[PH2]C(=O)C1=CC=CC=C1 HLJYBXJFKDDIBI-UHFFFAOYSA-N 0.000 description 1
- 206010036346 Posterior capsule opacification Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- ZNZDJSGUWLGTLA-UHFFFAOYSA-N [(1-oxo-1-phenylpropan-2-ylidene)amino] benzoate Chemical compound C=1C=CC=CC=1C(=O)C(C)=NOC(=O)C1=CC=CC=C1 ZNZDJSGUWLGTLA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- JVASZXZJOJUKDT-UHFFFAOYSA-N bis(1-aminocyclohexa-2,4-dien-1-yl)methanone Chemical class C1C=CC=CC1(N)C(=O)C1(N)CC=CC=C1 JVASZXZJOJUKDT-UHFFFAOYSA-N 0.000 description 1
- CQAIBOSCGCTHPV-UHFFFAOYSA-N bis(1-hydroxycyclohexa-2,4-dien-1-yl)methanone Chemical class C1C=CC=CC1(O)C(=O)C1(O)CC=CC=C1 CQAIBOSCGCTHPV-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 210000001542 lens epithelial cell Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000002407 tissue scaffold Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- 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
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPQ1978 | 1999-08-02 | ||
| AUPQ1978A AUPQ197899A0 (en) | 1999-08-02 | 1999-08-02 | Biomedical compositions |
| PCT/AU2000/000915 WO2001008603A1 (en) | 1999-08-02 | 2000-08-02 | Biomedical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2391817A1 CA2391817A1 (en) | 2001-02-08 |
| CA2391817C true CA2391817C (en) | 2010-07-20 |
Family
ID=3816158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2391817A Expired - Fee Related CA2391817C (en) | 1999-08-02 | 2000-08-02 | Biomedical compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7348022B1 (enExample) |
| EP (1) | EP1207816A4 (enExample) |
| JP (1) | JP2003505584A (enExample) |
| AU (1) | AUPQ197899A0 (enExample) |
| CA (1) | CA2391817C (enExample) |
| HK (1) | HK1048055A1 (enExample) |
| WO (1) | WO2001008603A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ197899A0 (en) * | 1999-08-02 | 1999-08-26 | Commonwealth Scientific And Industrial Research Organisation | Biomedical compositions |
| AU2002950469A0 (en) * | 2002-07-30 | 2002-09-12 | Commonwealth Scientific And Industrial Research Organisation | Improved biomedical compositions |
| US6703378B1 (en) * | 2002-09-19 | 2004-03-09 | Bausch & Lomb Incorporated | Vitreoretinal tamponades based on fluorosilicone fluids |
| US8802651B2 (en) | 2004-06-30 | 2014-08-12 | Abbott Medical Optics Inc. | Hyaluronic acid in the enhancement of lens regeneration |
| EP2010100B1 (en) * | 2006-04-27 | 2018-11-28 | Johnson & Johnson Surgical Vision, Inc. | Materials comprising polysiloxane polymers for enhancement of lens regeneration |
| US7559949B2 (en) * | 2006-04-28 | 2009-07-14 | Leonard Pinchuk | Injectable intraocular lens that minimizes posterior capsule opacification and methods and materials for realizing same |
| EP2020970A4 (en) | 2006-05-03 | 2013-11-13 | Vision Crc Ltd | EYE TREATMENT |
| WO2007128051A1 (en) * | 2006-05-03 | 2007-11-15 | Vision Crc Limited | Biological polysiloxanes |
| SG192187A1 (en) * | 2011-02-28 | 2013-08-30 | Coopervision Int Holding Co Lp | Phosphine-containing hydrogel contact lenses |
| EP2672926B1 (en) | 2011-03-21 | 2017-05-31 | Adventus Technology, Inc. | Restoration of accommodation by lens refilling |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136250A (en) | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
| US4616045A (en) * | 1983-06-23 | 1986-10-07 | Gbf, Inc. | Process of preparing an oxygen permeable, styrene based, contact lens material |
| US4542542A (en) * | 1983-07-21 | 1985-09-24 | Innovative Surgical Products, Inc. | Correction of defects in the eye and compositions therefor |
| JPS6121134A (ja) * | 1984-07-10 | 1986-01-29 | Yokohama Rubber Co Ltd:The | 新規アクリル変性シリコ−ン樹脂 |
| US4605712A (en) * | 1984-09-24 | 1986-08-12 | Ciba-Geigy Corporation | Unsaturated polysiloxanes and polymers thereof |
| US4563539A (en) | 1984-12-18 | 1986-01-07 | Dow Corning Corporation | Acrylofunctional silicones |
| US5236970A (en) | 1987-02-05 | 1993-08-17 | Allergan, Inc. | Optically clear reinforced silicone elastomers of high optical refractive index and improved mechanical properties for use in intraocular lenses |
| JPS63209648A (ja) * | 1987-02-27 | 1988-08-31 | セイコーエプソン株式会社 | 眼内レンズ |
| JPS63216574A (ja) | 1987-03-06 | 1988-09-08 | キヤノン株式会社 | 眼内レンズ用組成物 |
| US4852969A (en) * | 1988-03-17 | 1989-08-01 | Minnesota Mining And Manufacturing Company | Silyl 2-amidoacetate and silyl 3-amidopropionate compositions and optical fiber made therefrom |
| JPH0761357B2 (ja) | 1988-03-28 | 1995-07-05 | ホーヤ株式会社 | 眼内レンズ |
| AU630732B2 (en) * | 1989-09-22 | 1992-11-05 | Minnesota Mining And Manufacturing Company | Radiation-curable silicone elastomers and pressure sensitive adhesives |
| US5079319A (en) | 1989-10-25 | 1992-01-07 | Ciba-Geigy Corporation | Reactive silicone and/or fluorine containing hydrophilic prepolymers and polymers thereof |
| EP0455585B1 (en) * | 1990-04-26 | 1994-03-23 | Ciba-Geigy Ag | Unsaturated urea polysiloxanes |
| US5397848A (en) * | 1991-04-25 | 1995-03-14 | Allergan, Inc. | Enhancing the hydrophilicity of silicone polymers |
| US5246979A (en) | 1991-05-31 | 1993-09-21 | Dow Corning Corporation | Heat stable acrylamide polysiloxane composition |
| WO1993002639A1 (en) * | 1991-08-06 | 1993-02-18 | Autogenesis Technologies, Inc. | Injectable collagen-based compositions for making intraocular lens |
| JPH05117332A (ja) * | 1991-10-30 | 1993-05-14 | Kao Corp | 放射線硬化性組成物 |
| US5233007A (en) | 1992-04-14 | 1993-08-03 | Allergan, Inc. | Polysiloxanes, methods of making same and high refractive index silicones made from same |
| DE69220950T2 (de) | 1992-04-21 | 1997-12-04 | Kabi Pharmacia Opthalmics Inc | Siloxanzusammensetzung mit hohem brechungsindex |
| US5444106A (en) | 1992-04-21 | 1995-08-22 | Kabi Pharmacia Ophthalmics, Inc. | High refractive index silicone compositions |
| US5278258A (en) | 1992-05-18 | 1994-01-11 | Allergan, Inc. | Cross-linked silicone polymers, fast curing silicone precursor compositions, and injectable intraocular lenses |
| JP3335216B2 (ja) | 1992-06-29 | 2002-10-15 | 株式会社メニコン | 眼用レンズ材料 |
| JP2774233B2 (ja) * | 1992-08-26 | 1998-07-09 | 株式会社メニコン | 眼用レンズ材料 |
| US5391590A (en) * | 1993-01-12 | 1995-02-21 | Allergan, Inc. | Injectable intraocular lens compositions and precursors thereof |
| US5468246A (en) | 1993-07-02 | 1995-11-21 | Iovision, Inc. | Intraocular lens injector |
| EP0748232B8 (en) | 1994-03-02 | 2009-03-25 | Boston Scientific Limited | Block copolymer elastomer catheter balloons |
| FR2726562B1 (fr) | 1994-11-08 | 1996-12-27 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| US5647409A (en) | 1995-04-04 | 1997-07-15 | Allergan | On-site syringe filling apparatus for viscoelastic materials, and corresponding method for on-site syringe filling |
| AUPN354595A0 (en) | 1995-06-14 | 1995-07-06 | Ciba-Geigy Ag | Novel materials |
| DE19649844C1 (de) | 1996-12-02 | 1997-12-18 | Goldschmidt Ag Th | Mit Acrylatgruppen modifizierte Organosiloxanylderivate von Alkandiolmonovinylethern, Verfahren zu deren Herstellung und deren Verwendung als strahlenhärtbare Bindemittel |
| AU7533696A (en) | 1996-12-13 | 1998-06-18 | Ciba-Geigy Ag | New materials |
| SE9800853D0 (sv) | 1998-03-16 | 1998-03-16 | Pharmacia & Upjohn Bv | Intraocular lens |
| US6361561B1 (en) | 1998-10-13 | 2002-03-26 | Pharmacia & Upjohn Ab | Injectable intraocular lens |
| US6066172A (en) * | 1998-10-13 | 2000-05-23 | Pharmacia & Upjohn Ab | Injectable intraocular lens |
| SE9803481D0 (sv) * | 1998-10-13 | 1998-10-13 | Pharmacia & Upjohn Ab | Photocurable siloxane polymers |
| EA005114B1 (ru) | 1998-10-13 | 2004-10-28 | Фармация Гронинген Бв | Полисилоксаны для изготовления внутриглазной линзы и способы изготовления внутриглазной линзы |
| AUPQ197799A0 (en) | 1999-08-02 | 1999-08-26 | Commonwealth Scientific And Industrial Research Organisation | Hydrophilic biomedical compositions |
| AUPQ197899A0 (en) | 1999-08-02 | 1999-08-26 | Commonwealth Scientific And Industrial Research Organisation | Biomedical compositions |
| US6432137B1 (en) | 1999-09-08 | 2002-08-13 | Medennium, Inc. | High refractive index silicone for use in intraocular lenses |
| SE0001352D0 (sv) | 2000-04-12 | 2000-04-12 | Pharmacia & Upjohn Bv | Injectable intraocular accommodating lens |
| ATE270611T1 (de) | 2000-04-21 | 2004-07-15 | Advanced Medical Optics Inc | Methode zur herstellung einer akkomodierfähigen intraokularlinse |
| JP4686839B2 (ja) | 2000-10-23 | 2011-05-25 | 東レ株式会社 | モノマー、ポリマーおよびそれを用いた眼用レンズ |
| EP1364663A1 (en) | 2002-05-21 | 2003-11-26 | Commonwealth Scientific And Industrial Research Organisation | Ocular devices with functionalized surface with adhesive properties |
| AU2002950469A0 (en) | 2002-07-30 | 2002-09-12 | Commonwealth Scientific And Industrial Research Organisation | Improved biomedical compositions |
-
1999
- 1999-08-02 AU AUPQ1978A patent/AUPQ197899A0/en not_active Abandoned
-
2000
- 2000-08-02 HK HK02107589.0A patent/HK1048055A1/zh unknown
- 2000-08-02 JP JP2001513340A patent/JP2003505584A/ja not_active Ceased
- 2000-08-02 US US10/048,700 patent/US7348022B1/en not_active Expired - Fee Related
- 2000-08-02 WO PCT/AU2000/000915 patent/WO2001008603A1/en not_active Ceased
- 2000-08-02 EP EP00947678A patent/EP1207816A4/en not_active Withdrawn
- 2000-08-02 CA CA2391817A patent/CA2391817C/en not_active Expired - Fee Related
-
2008
- 2008-01-24 US US12/019,321 patent/US7556822B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2391817A1 (en) | 2001-02-08 |
| AUPQ197899A0 (en) | 1999-08-26 |
| US7556822B2 (en) | 2009-07-07 |
| WO2001008603A1 (en) | 2001-02-08 |
| HK1048055A1 (zh) | 2003-03-21 |
| JP2003505584A (ja) | 2003-02-12 |
| US20080114090A1 (en) | 2008-05-15 |
| EP1207816A4 (en) | 2008-12-24 |
| EP1207816A1 (en) | 2002-05-29 |
| US7348022B1 (en) | 2008-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140804 |