CA2906238A1 - Compounds and compositions for drug release - Google Patents
Compounds and compositions for drug release Download PDFInfo
- Publication number
- CA2906238A1 CA2906238A1 CA2906238A CA2906238A CA2906238A1 CA 2906238 A1 CA2906238 A1 CA 2906238A1 CA 2906238 A CA2906238 A CA 2906238A CA 2906238 A CA2906238 A CA 2906238A CA 2906238 A1 CA2906238 A1 CA 2906238A1
- Authority
- CA
- Canada
- Prior art keywords
- article
- bio2
- compound
- biologically active
- active agent
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 103
- 239000000203 mixture Substances 0.000 title claims description 64
- 239000003814 drug Substances 0.000 title abstract description 56
- 229940079593 drug Drugs 0.000 title abstract description 53
- 239000013543 active substance Substances 0.000 claims abstract description 77
- 238000000576 coating method Methods 0.000 claims abstract description 46
- 239000011248 coating agent Substances 0.000 claims abstract description 35
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 92
- -1 poly(ethylene glycol) Polymers 0.000 claims description 56
- 229960003405 ciprofloxacin Drugs 0.000 claims description 46
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 26
- 229920005601 base polymer Polymers 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- 150000004985 diamines Chemical class 0.000 claims description 16
- 230000003115 biocidal effect Effects 0.000 claims description 14
- 230000000399 orthopedic effect Effects 0.000 claims description 14
- 230000002792 vascular Effects 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 12
- 239000007943 implant Substances 0.000 claims description 12
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 12
- 239000004599 antimicrobial Substances 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 9
- 239000003242 anti bacterial agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 239000003146 anticoagulant agent Substances 0.000 claims description 7
- 210000003709 heart valve Anatomy 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- 102000004169 proteins and genes Human genes 0.000 claims description 7
- 206010019909 Hernia Diseases 0.000 claims description 6
- 230000001028 anti-proliverative effect Effects 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 claims description 4
- 241001631457 Cannula Species 0.000 claims description 4
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000004071 biological effect Effects 0.000 claims description 4
- 229960003923 gatifloxacin Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229960003376 levofloxacin Drugs 0.000 claims description 4
- 210000003041 ligament Anatomy 0.000 claims description 4
- 229960003702 moxifloxacin Drugs 0.000 claims description 4
- FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims description 4
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- 239000005700 Putrescine Substances 0.000 claims description 3
- 206010052428 Wound Diseases 0.000 claims description 3
- 208000027418 Wounds and injury Diseases 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000227 bioadhesive Substances 0.000 claims description 3
- 229920002988 biodegradable polymer Polymers 0.000 claims description 3
- 239000004621 biodegradable polymer Substances 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 3
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 3
- 239000004053 dental implant Substances 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 230000002500 effect on skin Effects 0.000 claims description 3
- 230000001815 facial effect Effects 0.000 claims description 3
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 238000007747 plating Methods 0.000 claims description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 3
- 210000003491 skin Anatomy 0.000 claims description 3
- 210000002435 tendon Anatomy 0.000 claims description 3
- 230000002861 ventricular Effects 0.000 claims description 3
- 230000029663 wound healing Effects 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 229940127090 anticoagulant agent Drugs 0.000 claims description 2
- 229960004676 antithrombotic agent Drugs 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000004626 polylactic acid Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 239000003306 quinoline derived antiinfective agent Substances 0.000 claims 3
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 claims 1
- 238000005191 phase separation Methods 0.000 abstract description 5
- 230000007774 longterm Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 124
- 239000000243 solution Substances 0.000 description 96
- 229940125782 compound 2 Drugs 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
- 229940126214 compound 3 Drugs 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 28
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 23
- 238000012512 characterization method Methods 0.000 description 19
- 239000012265 solid product Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 16
- WDRFFJWBUDTUCA-UHFFFAOYSA-N chlorhexidine acetate Chemical compound CC(O)=O.CC(O)=O.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WDRFFJWBUDTUCA-UHFFFAOYSA-N 0.000 description 15
- 229960001884 chlorhexidine diacetate Drugs 0.000 description 15
- 229940088516 cipro Drugs 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 230000000845 anti-microbial effect Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 10
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 8
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
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- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 5
- 229940056360 penicillin g Drugs 0.000 description 5
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- 239000002243 precursor Substances 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 230000008901 benefit Effects 0.000 description 4
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- 238000010168 coupling process Methods 0.000 description 4
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- 238000012377 drug delivery Methods 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- MVTQIFVKRXBCHS-SMMNFGSLSA-N N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone Chemical compound CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)n2.CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1 MVTQIFVKRXBCHS-SMMNFGSLSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- 229940124587 cephalosporin Drugs 0.000 description 3
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- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229960005091 chloramphenicol Drugs 0.000 description 3
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 3
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- 238000002648 combination therapy Methods 0.000 description 3
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- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000004626 scanning electron microscopy Methods 0.000 description 3
- 229940083542 sodium Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 description 3
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021005417A1 (en) * | 2019-07-10 | 2021-01-14 | Ripple Therapeutics Corporations | Surface coatings and implantable devices comprising dimeric steroid prodrugs, and uses thereof |
| WO2021014217A1 (en) * | 2019-07-25 | 2021-01-28 | Ripple Therapeutics Corporation | Articles comprising steroid dimers and their use in the delivery of therapeutic agents |
| US10945958B2 (en) | 2018-02-02 | 2021-03-16 | Ripple Therapeutics Corporation | Dexamethasone prodrug compositions and uses thereof |
| US11279729B2 (en) | 2020-05-01 | 2022-03-22 | Ripple Therapeutics Corporation | Heterodimer compositions and methods for the treatment of ocular disorders |
| US12473326B2 (en) | 2019-02-01 | 2025-11-18 | Ripple Therapeutics Corporation | Crystalline forms of dexamethasone dimers and uses thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3796948A4 (en) * | 2018-05-22 | 2022-03-02 | Interface Biologics Inc. | Compositions and methods for delivering drugs to a vessel wall |
| CN108774315A (zh) * | 2018-06-27 | 2018-11-09 | 湖南华腾制药有限公司 | Peg化诺氟沙星及其抑菌应用 |
| CN116763993B (zh) * | 2023-07-04 | 2024-10-08 | 四川大学 | 一种由炎症微环境介导的药物响应释放仿生心脏瓣膜及其制备方法和用途 |
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| DE1768345B2 (de) * | 1968-05-03 | 1976-12-02 | Hoechst Ag, 6000 Frankfurt | Dimere steroid-21-alkylcarbonate und verfahren zu ihrer herstellung |
| US5217493A (en) * | 1992-03-11 | 1993-06-08 | Board Of Regents, The University Of Texas System | Antibacterial coated medical implants |
| DE19521642C2 (de) * | 1995-06-14 | 2000-11-09 | Aesculap Ag & Co Kg | Implantat, seine Verwendung in der Chirurgie und Verfahren zu seiner Herstellung |
| KR0176334B1 (ko) * | 1996-08-19 | 1999-04-01 | 박원훈 | 내인체 감염성 삽입금속표면의 코팅방법 및 그 치료기술 |
| AU2002259045B2 (en) * | 2001-04-26 | 2008-05-22 | Psivida Us Inc. | Sustained release drug delivery system containing codrugs |
| AUPR879601A0 (en) * | 2001-11-09 | 2001-12-06 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| US7541048B2 (en) * | 2004-04-06 | 2009-06-02 | Surmodics, Inc. | Coating compositions for bioactive agents |
| CA2467321A1 (en) * | 2004-05-14 | 2005-11-14 | Paul J. Santerre | Polymeric coupling agents and pharmaceutically-active polymers made therefrom |
| EP1744787A4 (en) * | 2004-05-14 | 2011-04-06 | Interface Biologics Inc | POLYMER COUPLING AGENTS AND PHARMACEUTICALLY ACTIVE POLYMERS MANUFACTURED THEREOF |
| CA2571320C (en) * | 2004-05-14 | 2016-05-10 | Paul J. Santerre | Polymeric coupling agents and pharmaceutically-active polymers made therefrom |
| US8414909B2 (en) * | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8357385B2 (en) * | 2008-04-07 | 2013-01-22 | Interface Biologics Inc. | Combination therapy for the treatment of bacterial infections |
| WO2010040188A1 (en) * | 2008-10-10 | 2010-04-15 | The Bionic Ear Institute | Biodegradable polymer - bioactive moiety conjugates |
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- 2014-03-17 US US14/776,903 patent/US20160038651A1/en not_active Abandoned
- 2014-03-17 CA CA2906238A patent/CA2906238A1/en not_active Abandoned
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- 2014-03-17 JP JP2015561873A patent/JP6518198B2/ja active Active
- 2014-03-17 EP EP14764271.4A patent/EP2968698B1/en not_active Not-in-force
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2018
- 2018-09-07 JP JP2018167744A patent/JP2019030671A/ja active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10945958B2 (en) | 2018-02-02 | 2021-03-16 | Ripple Therapeutics Corporation | Dexamethasone prodrug compositions and uses thereof |
| US10959954B2 (en) | 2018-02-02 | 2021-03-30 | Ripple Therapeutics Corporation | Dexamethasone prodrug compositions and uses thereof |
| US11612567B2 (en) | 2018-02-02 | 2023-03-28 | Ripple Therapeutics Corporation | Ocular inserts comprising a covalently linked steroid dimer |
| US12473326B2 (en) | 2019-02-01 | 2025-11-18 | Ripple Therapeutics Corporation | Crystalline forms of dexamethasone dimers and uses thereof |
| WO2021005417A1 (en) * | 2019-07-10 | 2021-01-14 | Ripple Therapeutics Corporations | Surface coatings and implantable devices comprising dimeric steroid prodrugs, and uses thereof |
| WO2021014217A1 (en) * | 2019-07-25 | 2021-01-28 | Ripple Therapeutics Corporation | Articles comprising steroid dimers and their use in the delivery of therapeutic agents |
| US11279729B2 (en) | 2020-05-01 | 2022-03-22 | Ripple Therapeutics Corporation | Heterodimer compositions and methods for the treatment of ocular disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2773179T3 (es) | 2020-07-09 |
| EP3357522A1 (en) | 2018-08-08 |
| JP2019030671A (ja) | 2019-02-28 |
| EP2968698B1 (en) | 2018-01-10 |
| WO2014139033A1 (en) | 2014-09-18 |
| US20160038651A1 (en) | 2016-02-11 |
| CN105377319A (zh) | 2016-03-02 |
| JP6518198B2 (ja) | 2019-05-22 |
| EP3357522B1 (en) | 2019-10-16 |
| CN105377319B (zh) | 2022-01-28 |
| EP2968698A4 (en) | 2016-11-23 |
| DK3357522T3 (da) | 2020-01-27 |
| EP2968698A1 (en) | 2016-01-20 |
| ES2665425T3 (es) | 2018-04-25 |
| JP2016514001A (ja) | 2016-05-19 |
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| FZDE | Discontinued |
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