CA2222646C - Compositions and methods for stabilizing polymers - Google Patents
Compositions and methods for stabilizing polymers Download PDFInfo
- Publication number
- CA2222646C CA2222646C CA002222646A CA2222646A CA2222646C CA 2222646 C CA2222646 C CA 2222646C CA 002222646 A CA002222646 A CA 002222646A CA 2222646 A CA2222646 A CA 2222646A CA 2222646 C CA2222646 C CA 2222646C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight percent
- chelating agent
- poly
- mixtures
- 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 abstract description 152
- 238000000034 method Methods 0.000 title claims abstract description 24
- 229920000642 polymer Polymers 0.000 title claims description 48
- 230000000087 stabilizing effect Effects 0.000 title claims description 11
- 239000002738 chelating agent Substances 0.000 claims abstract description 68
- -1 poly(acrylic acids) Polymers 0.000 claims abstract description 55
- 239000003623 enhancer Substances 0.000 claims abstract description 29
- 239000000227 bioadhesive Substances 0.000 claims abstract description 24
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 21
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910021645 metal ion Inorganic materials 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 22
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 20
- 229920002125 Sokalan® Polymers 0.000 claims description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 16
- 229920001222 biopolymer Polymers 0.000 claims description 16
- 239000008103 glucose Substances 0.000 claims description 16
- 229940124447 delivery agent Drugs 0.000 claims description 15
- 230000000536 complexating effect Effects 0.000 claims description 14
- 230000002708 enhancing effect Effects 0.000 claims description 14
- 230000003197 catalytic effect Effects 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- 229920002307 Dextran Polymers 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- DKPHLYCEFBDQKM-UHFFFAOYSA-H hexapotassium;1-phosphonato-n,n-bis(phosphonatomethyl)methanamine Chemical group [K+].[K+].[K+].[K+].[K+].[K+].[O-]P([O-])(=O)CN(CP([O-])([O-])=O)CP([O-])([O-])=O DKPHLYCEFBDQKM-UHFFFAOYSA-H 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 4
- FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 claims description 4
- 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 claims description 4
- 229960004194 lidocaine Drugs 0.000 claims description 4
- 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 claims description 3
- CMQAMENQCKNUPB-UHFFFAOYSA-N NC1CCOP(=O)O1 Chemical class NC1CCOP(=O)O1 CMQAMENQCKNUPB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000009286 beneficial effect Effects 0.000 claims description 3
- 239000000032 diagnostic agent Substances 0.000 claims description 3
- 229940039227 diagnostic agent Drugs 0.000 claims description 3
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002674 hyaluronan Polymers 0.000 claims description 3
- 229960003160 hyaluronic acid Drugs 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 235000015097 nutrients Nutrition 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- 239000011782 vitamin Substances 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 2
- YLXIPWWIOISBDD-NDAAPVSOSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;4-[(1r)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CNC[C@H](O)C1=CC=C(O)C(O)=C1 YLXIPWWIOISBDD-NDAAPVSOSA-N 0.000 claims description 2
- RDEIXVOBVLKYNT-VQBXQJRRSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]o Chemical compound OS(O)(=O)=O.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)C(C)N)N)[C@@H](N)C[C@H]1N.O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N RDEIXVOBVLKYNT-VQBXQJRRSA-N 0.000 claims description 2
- HBXAVWDHOQFJAH-JGVFFNPUSA-N (2r,3s)-3-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C[C@H]1CCN(C(=O)OC(C)(C)C)[C@H]1C(O)=O HBXAVWDHOQFJAH-JGVFFNPUSA-N 0.000 claims description 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 2
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 claims description 2
- GFRUPHOKLBPHTQ-UHFFFAOYSA-N 2-(2-cyclohexyl-2-hydroxy-1-oxo-2-phenylethoxy)ethyl-diethyl-methylammonium Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC[N+](C)(CC)CC)C1CCCCC1 GFRUPHOKLBPHTQ-UHFFFAOYSA-N 0.000 claims description 2
- BFUUJUGQJUTPAF-UHFFFAOYSA-N 2-(3-amino-4-propoxybenzoyl)oxyethyl-diethylazanium;chloride Chemical compound [Cl-].CCCOC1=CC=C(C(=O)OCC[NH+](CC)CC)C=C1N BFUUJUGQJUTPAF-UHFFFAOYSA-N 0.000 claims description 2
- SDEXVKFYBBHUKN-UHFFFAOYSA-N 2-(dibutylcarbamoyloxy)ethyl-ethyl-dimethylazanium Chemical compound CCCCN(CCCC)C(=O)OCC[N+](C)(C)CC SDEXVKFYBBHUKN-UHFFFAOYSA-N 0.000 claims description 2
- OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 claims description 2
- QSAVEGSLJISCDF-UHFFFAOYSA-N 2-hydroxy-2-phenylacetic acid (1,2,2,6-tetramethyl-4-piperidinyl) ester Chemical compound C1C(C)(C)N(C)C(C)CC1OC(=O)C(O)C1=CC=CC=C1 QSAVEGSLJISCDF-UHFFFAOYSA-N 0.000 claims description 2
- QAIRPCMWTLMPCW-UHFFFAOYSA-N 4-bromo-2,6-diethylpyridine Chemical compound CCC1=CC(Br)=CC(CC)=N1 QAIRPCMWTLMPCW-UHFFFAOYSA-N 0.000 claims description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 2
- BLGXFZZNTVWLAY-DKJBZYCGSA-N Corynanthine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-DKJBZYCGSA-N 0.000 claims description 2
- DDRUVFKWNXGBTK-UHFFFAOYSA-N Corynanthine Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)OC(=O)C)=C3NC2=C1 DDRUVFKWNXGBTK-UHFFFAOYSA-N 0.000 claims description 2
- VTUSIVBDOCDNHS-UHFFFAOYSA-N Etidocaine Chemical compound CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C VTUSIVBDOCDNHS-UHFFFAOYSA-N 0.000 claims description 2
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 2
- GZENKSODFLBBHQ-ILSZZQPISA-N Medrysone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 GZENKSODFLBBHQ-ILSZZQPISA-N 0.000 claims description 2
- DJDFFEBSKJCGHC-UHFFFAOYSA-N Naphazoline Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 DJDFFEBSKJCGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- SSOXZAQUVINQSA-BTJKTKAUSA-N Pheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=CC=C1 SSOXZAQUVINQSA-BTJKTKAUSA-N 0.000 claims description 2
- 229920002413 Polyhexanide Polymers 0.000 claims description 2
- 108010093965 Polymyxin B Proteins 0.000 claims description 2
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 claims description 2
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004098 Tetracycline Substances 0.000 claims description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims description 2
- BGDKAVGWHJFAGW-UHFFFAOYSA-N Tropicamide Chemical compound C=1C=CC=CC=1C(CO)C(=O)N(CC)CC1=CC=NC=C1 BGDKAVGWHJFAGW-UHFFFAOYSA-N 0.000 claims description 2
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 claims description 2
- MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 claims description 2
- JUGOREOARAHOCO-UHFFFAOYSA-M acetylcholine chloride Chemical compound [Cl-].CC(=O)OCC[N+](C)(C)C JUGOREOARAHOCO-UHFFFAOYSA-M 0.000 claims description 2
- 229960004266 acetylcholine chloride Drugs 0.000 claims description 2
- 229960004150 aciclovir Drugs 0.000 claims description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 2
- 229960002684 aminocaproic acid Drugs 0.000 claims description 2
- 229960003420 antazoline phosphate Drugs 0.000 claims description 2
- 229940114079 arachidonic acid Drugs 0.000 claims description 2
- 235000021342 arachidonic acid Nutrition 0.000 claims description 2
- 229940045232 benoxinate hydrochloride Drugs 0.000 claims description 2
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 claims description 2
- CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 claims description 2
- 229960004347 betaxolol hydrochloride Drugs 0.000 claims description 2
- 229960003150 bupivacaine Drugs 0.000 claims description 2
- 229960004484 carbachol Drugs 0.000 claims description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
- LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 claims description 2
- 229960001222 carteolol Drugs 0.000 claims description 2
- DWSGTFTVBLXELC-RDYJJYPNSA-N chembl1319362 Chemical compound Br.O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(O)C1=CC=CC=C1 DWSGTFTVBLXELC-RDYJJYPNSA-N 0.000 claims description 2
- 229960005091 chloramphenicol Drugs 0.000 claims description 2
- 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 claims description 2
- 229960003185 chlortetracycline hydrochloride Drugs 0.000 claims description 2
- 229960002896 clonidine Drugs 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 229960000265 cromoglicic acid Drugs 0.000 claims description 2
- 229960001815 cyclopentolate Drugs 0.000 claims description 2
- SKYSRIRYMSLOIN-UHFFFAOYSA-N cyclopentolate Chemical compound C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 SKYSRIRYMSLOIN-UHFFFAOYSA-N 0.000 claims description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003715 demecarium bromide Drugs 0.000 claims description 2
- YHKBUDZECQDYBR-UHFFFAOYSA-L demecarium bromide Chemical compound [Br-].[Br-].C=1C=CC([N+](C)(C)C)=CC=1OC(=O)N(C)CCCCCCCCCCN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 YHKBUDZECQDYBR-UHFFFAOYSA-L 0.000 claims description 2
- 229960003957 dexamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 2
- 229960001259 diclofenac Drugs 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- 229960005081 diclofenamide Drugs 0.000 claims description 2
- GJQPMPFPNINLKP-UHFFFAOYSA-N diclofenamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 GJQPMPFPNINLKP-UHFFFAOYSA-N 0.000 claims description 2
- MUCZHBLJLSDCSD-UHFFFAOYSA-N diisopropyl fluorophosphate Chemical compound CC(C)OP(F)(=O)OC(C)C MUCZHBLJLSDCSD-UHFFFAOYSA-N 0.000 claims description 2
- VKFAUCPBMAGVRG-UHFFFAOYSA-N dipivefrin hydrochloride Chemical compound [Cl-].C[NH2+]CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 VKFAUCPBMAGVRG-UHFFFAOYSA-N 0.000 claims description 2
- 229940090570 dipivefrin hydrochloride Drugs 0.000 claims description 2
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims description 2
- 229960002179 ephedrine Drugs 0.000 claims description 2
- 229960003157 epinephrine bitartrate Drugs 0.000 claims description 2
- 229960003276 erythromycin Drugs 0.000 claims description 2
- 229960000285 ethambutol Drugs 0.000 claims description 2
- XRJIGJFEKPXBTD-UHFFFAOYSA-N ethyl-[2-(2-hydroxy-2,2-diphenylacetyl)oxyethyl]-dimethylazanium Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC[N+](C)(C)CC)C1=CC=CC=C1 XRJIGJFEKPXBTD-UHFFFAOYSA-N 0.000 claims description 2
- 229960003976 etidocaine Drugs 0.000 claims description 2
- 229950002420 eucatropine Drugs 0.000 claims description 2
- 229960001048 fluorometholone Drugs 0.000 claims description 2
- 229960005051 fluostigmine Drugs 0.000 claims description 2
- ZWCXYZRRTRDGQE-SORVKSEFSA-N gramicidina Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-SORVKSEFSA-N 0.000 claims description 2
- 229960002106 homatropine hydrobromide Drugs 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229960004716 idoxuridine Drugs 0.000 claims description 2
- 229960000367 inositol Drugs 0.000 claims description 2
- 229960002479 isosorbide Drugs 0.000 claims description 2
- 229940085269 lachesine Drugs 0.000 claims description 2
- 229960000831 levobunolol Drugs 0.000 claims description 2
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 claims description 2
- 229960001120 levocabastine Drugs 0.000 claims description 2
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 claims description 2
- 229960001011 medrysone Drugs 0.000 claims description 2
- 229960002409 mepivacaine Drugs 0.000 claims description 2
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 2
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 claims description 2
- 229960002329 methacholine Drugs 0.000 claims description 2
- 229960004083 methazolamide Drugs 0.000 claims description 2
- FLOSMHQXBMRNHR-DAXSKMNVSA-N methazolamide Chemical compound CC(=O)\N=C1/SC(S(N)(=O)=O)=NN1C FLOSMHQXBMRNHR-DAXSKMNVSA-N 0.000 claims description 2
- 229960004760 naphazoline hydrochloride Drugs 0.000 claims description 2
- 229960003255 natamycin Drugs 0.000 claims description 2
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 claims description 2
- 235000010298 natamycin Nutrition 0.000 claims description 2
- 239000004311 natamycin Substances 0.000 claims description 2
- OIXVKQDWLFHVGR-WQDIDPJDSA-N neomycin B sulfate Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO OIXVKQDWLFHVGR-WQDIDPJDSA-N 0.000 claims description 2
- 229940053050 neomycin sulfate Drugs 0.000 claims description 2
- 229960002362 neostigmine Drugs 0.000 claims description 2
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 claims description 2
- 229960002748 norepinephrine Drugs 0.000 claims description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960001699 ofloxacin Drugs 0.000 claims description 2
- 229960003502 oxybuprocaine Drugs 0.000 claims description 2
- CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 claims description 2
- 229960002740 oxyphenonium Drugs 0.000 claims description 2
- 229960001339 pheniramine maleate Drugs 0.000 claims description 2
- 229960003733 phenylephrine hydrochloride Drugs 0.000 claims description 2
- OCYSGIYOVXAGKQ-FVGYRXGTSA-N phenylephrine hydrochloride Chemical compound [H+].[Cl-].CNC[C@H](O)C1=CC=CC(O)=C1 OCYSGIYOVXAGKQ-FVGYRXGTSA-N 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003907 phosphatidylinositol monophosphates Chemical class 0.000 claims description 2
- 229960002139 pilocarpine hydrochloride Drugs 0.000 claims description 2
- RNAICSBVACLLGM-GNAZCLTHSA-N pilocarpine hydrochloride Chemical compound Cl.C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C RNAICSBVACLLGM-GNAZCLTHSA-N 0.000 claims description 2
- 229920000024 polymyxin B Polymers 0.000 claims description 2
- 229960005266 polymyxin b Drugs 0.000 claims description 2
- JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 claims description 2
- 229960002943 prednisolone sodium phosphate Drugs 0.000 claims description 2
- 229960001371 proparacaine hydrochloride Drugs 0.000 claims description 2
- 229960004499 scopolamine hydrobromide Drugs 0.000 claims description 2
- WTGQALLALWYDJH-MOUKNHLCSA-N scopolamine hydrobromide (anhydrous) Chemical compound Br.C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-MOUKNHLCSA-N 0.000 claims description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 2
- LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 claims description 2
- 229950004311 sorbinil Drugs 0.000 claims description 2
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 claims description 2
- 229960002673 sulfacetamide Drugs 0.000 claims description 2
- 229960000654 sulfafurazole Drugs 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 229960001603 tamoxifen Drugs 0.000 claims description 2
- 229960002372 tetracaine Drugs 0.000 claims description 2
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 2
- 229960002494 tetracaine hydrochloride Drugs 0.000 claims description 2
- 229960002180 tetracycline Drugs 0.000 claims description 2
- 229930101283 tetracycline Natural products 0.000 claims description 2
- 235000019364 tetracycline Nutrition 0.000 claims description 2
- 150000003522 tetracyclines Chemical class 0.000 claims description 2
- 229940021790 tetrahydrozoline hydrochloride Drugs 0.000 claims description 2
- BJORNXNYWNIWEY-UHFFFAOYSA-N tetrahydrozoline hydrochloride Chemical compound Cl.N1CCN=C1C1C2=CC=CC=C2CCC1 BJORNXNYWNIWEY-UHFFFAOYSA-N 0.000 claims description 2
- 229940104230 thymidine Drugs 0.000 claims description 2
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 claims description 2
- 229960003962 trifluridine Drugs 0.000 claims description 2
- 229960004791 tropicamide Drugs 0.000 claims description 2
- 229960003636 vidarabine Drugs 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 claims 1
- JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 claims 1
- 229930003347 Atropine Natural products 0.000 claims 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 claims 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims 1
- 229960000396 atropine Drugs 0.000 claims 1
- 229960000905 indomethacin Drugs 0.000 claims 1
- 229960001697 physostigmine Drugs 0.000 claims 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 claims 1
- 229940018203 pyrilamine maleate Drugs 0.000 claims 1
- 229960000454 timolol hemihydrate Drugs 0.000 claims 1
- 229960005221 timolol maleate Drugs 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 6
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 description 5
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 5
- 229940119743 dextran 70 Drugs 0.000 description 5
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012929 tonicity agent Substances 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 229920000148 Polycarbophil calcium Polymers 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 229950005134 polycarbophil Drugs 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical class OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002997 ophthalmic solution Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Materials For Medical Uses (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/493,761 | 1995-06-22 | ||
| US08/493,761 US5683993A (en) | 1995-06-22 | 1995-06-22 | Compositions and methods for stabilizing polymers |
| PCT/EP1996/002539 WO1997000669A1 (en) | 1995-06-22 | 1996-06-12 | Compositions and methods for stabilizing polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2222646A1 CA2222646A1 (en) | 1997-01-09 |
| CA2222646C true CA2222646C (en) | 2009-12-08 |
Family
ID=23961593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002222646A Expired - Fee Related CA2222646C (en) | 1995-06-22 | 1996-06-12 | Compositions and methods for stabilizing polymers |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5683993A (enExample) |
| EP (1) | EP0833609B1 (enExample) |
| JP (3) | JP4260881B2 (enExample) |
| AT (1) | ATE208189T1 (enExample) |
| AU (1) | AU715686B2 (enExample) |
| CA (1) | CA2222646C (enExample) |
| CY (1) | CY2323B1 (enExample) |
| DE (1) | DE69616791T2 (enExample) |
| DK (1) | DK0833609T3 (enExample) |
| ES (1) | ES2167581T3 (enExample) |
| PT (1) | PT833609E (enExample) |
| TW (1) | TW358109B (enExample) |
| WO (1) | WO1997000669A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2284202T3 (es) * | 1997-05-14 | 2007-11-01 | Senju Pharmaceutical Co., Ltd. | Preparaciones acuosas en suspension con excelente redispersabilidad. |
| DK0893121T3 (da) * | 1997-06-27 | 2002-06-17 | Akzo Nobel Nv | Flydende oral medicinopløsning |
| DE19744113A1 (de) * | 1997-10-06 | 1999-04-15 | Mann Gerhard Chem Pharm Fab | Dexamethason-Gel |
| EP0938896A1 (en) * | 1998-01-15 | 1999-09-01 | Novartis AG | Autoclavable pharmaceutical compositions containing a chelating agent |
| US5885550A (en) * | 1998-07-02 | 1999-03-23 | Vallier; Deandra K. | Ophthalmic whitening solution |
| US6627660B1 (en) * | 1999-11-16 | 2003-09-30 | New River Pharmaceuticals Inc. | Stabilized thyroxine compounds |
| WO2002070648A2 (en) | 2000-11-17 | 2002-09-12 | Hematech, Llc | Expression of xenogenous (human) immunoglobulins in cloned, transgenic ungulates |
| AU2002360939A1 (en) * | 2001-11-21 | 2003-06-10 | Novartis Ag | Composition for stabilizing hyaluronic acid |
| US20040115160A1 (en) * | 2002-12-13 | 2004-06-17 | Salamone Joseph C. | Quaternary ammonium esters for disinfection and preservation |
| US20050084468A1 (en) * | 2003-10-17 | 2005-04-21 | Colgate-Palmolive Company | Antimicrobial cleaning composition |
| TWI454286B (zh) | 2006-03-17 | 2014-10-01 | Johnson & Johnson Vision Care | 安定氧化性不安定組合物之方法 |
| JP5160757B2 (ja) * | 2006-09-01 | 2013-03-13 | ホーユー株式会社 | 毛髪脱染剤組成物 |
| TWI394564B (zh) * | 2006-09-21 | 2013-05-01 | Alcon Res Ltd | 自行保存型水性藥學組成物 |
| WO2008036855A2 (en) * | 2006-09-21 | 2008-03-27 | Alcon Research, Ltd. | Self-preserved aqueous pharmaceutical compositions |
| PL2066300T5 (pl) * | 2006-09-28 | 2020-03-31 | Novartis Ag | Samokonserwujące wodne kompozycje farmaceutyczne |
| JP5216596B2 (ja) * | 2006-10-26 | 2013-06-19 | 千寿製薬株式会社 | 眼科用水性液剤 |
| WO2008121199A2 (en) | 2007-03-28 | 2008-10-09 | University Of Iowa Research Foundation | Transgenic animal models of disease |
| US8759321B2 (en) | 2007-06-13 | 2014-06-24 | Bausch & Lomb Incorporated | Ophthalmic composition with hyaluronic acid and polymeric biguanide |
| US8119112B2 (en) | 2008-01-31 | 2012-02-21 | Bausch & Lomb Incorporated | Ophthalmic compositions with an amphoteric surfactant and hyaluronic acid |
| PL2254549T5 (pl) * | 2008-03-17 | 2019-12-31 | Alcon Research, Ltd. | Wodne kompozycje farmaceutyczne zawierające kompleksy boran-poliole |
| US8299079B2 (en) | 2009-05-22 | 2012-10-30 | Kaufman Herbert E | Preparations and methods for ameliorating or reducing presbyopia |
| WO2010135731A1 (en) * | 2009-05-22 | 2010-11-25 | Kaufman Herbert E | Preparations and methods for ameliorating or reducing presbyopia |
| TWI489997B (zh) | 2009-06-19 | 2015-07-01 | Alcon Res Ltd | 含有硼酸－多元醇錯合物之水性藥學組成物 |
| PT2709445T (pt) | 2011-05-16 | 2018-11-27 | Univ Missouri | Animais resistentes ao vírus da síntese reprodutiva e respiratória porcino |
| US9661831B2 (en) | 2011-11-03 | 2017-05-30 | University Of Iowa Research Foundation | Transgenic pig models of cystic fibrosis |
| US20130177599A1 (en) * | 2012-01-06 | 2013-07-11 | Insite Vision Incorporated | Methods and kits for extending contact lens use |
| KR101400791B1 (ko) | 2012-10-04 | 2014-05-29 | 주식회사대성미생물연구소 | 동물용 복합 기능성 항생제 조성물 |
| WO2016187426A1 (en) | 2015-05-19 | 2016-11-24 | Amorphex Therapeutics Llc | A device that delivers a sustained low-dose of a myopia-suppressing drug |
| US10231961B1 (en) | 2017-02-07 | 2019-03-19 | Genus Lifesciences Inc. | Pharmaceutical compositions and methods of using the same |
| US10413505B1 (en) | 2017-02-07 | 2019-09-17 | Genus Lifesciences Inc. | Pharmaceutical compositions and methods of using the same |
| US10149843B1 (en) | 2017-02-07 | 2018-12-11 | Gneus Lifescineces Inc. | Pharmaceutical compositions and methods of using the same |
| CN109387622A (zh) * | 2018-03-02 | 2019-02-26 | 国家纳米科学中心 | 一种高分子材料表面修饰方法及其应用 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2322883A1 (de) * | 1973-05-07 | 1974-11-28 | Roehm Gmbh | Wasserloesliche polymerisate |
| DE2743764C2 (de) * | 1977-09-29 | 1982-07-22 | Hoechst Ag, 6000 Frankfurt | Wäßrige Kunststoffdispersion auf Basis von Vinylpolymeren |
| DE2810348A1 (de) * | 1978-03-10 | 1979-09-20 | Hoechst Ag | Waessrige kunststoffdispersion auf basis von vinylpolymeren |
| US4303568A (en) * | 1979-12-10 | 1981-12-01 | Betz Laboratories, Inc. | Corrosion inhibition treatments and method |
| US4474916A (en) * | 1982-07-27 | 1984-10-02 | Basf Aktiengesellschaft | Concentrated aqueous solutions of mixtures of organic complexing agents and dispersing agents based on polymeric aliphatic carboxylic acids |
| ATE151286T1 (de) * | 1983-11-14 | 1997-04-15 | Columbia Lab Inc | Bioadhäsive mittel |
| JPS60184013A (ja) * | 1984-03-01 | 1985-09-19 | Yoshitomi Pharmaceut Ind Ltd | 点眼剤 |
| US4540738A (en) * | 1984-12-07 | 1985-09-10 | The Kendall Company | Acrylic adhesive composition comprising an alpha amino phosphonic acid or salt having improved stability |
| US4889689A (en) * | 1986-10-14 | 1989-12-26 | Ciba-Geigy Corporation | Method of disinfecting a soft contact lens with a diethylene triamine penta(methylenephosphonic acid) stabilized hydrogen peroxide solution |
| US4900469A (en) * | 1986-10-21 | 1990-02-13 | The Clorox Company | Thickened peracid precursor compositions |
| US4812173A (en) * | 1987-05-01 | 1989-03-14 | Ciba-Geigy Corporation | Stabilized hydrogen peroxide contact lens disinfecting solution |
| US5192535A (en) * | 1988-02-08 | 1993-03-09 | Insite Vision Incorporated | Ophthalmic suspensions |
| DE3805663A1 (de) * | 1988-02-24 | 1989-09-07 | Henkel Kgaa | Oxaalkanpolyphosphonsaeuren, ihre verwendung als thresholder sowie diese verbindungen enthaltende, komplexierend wirkende zusammensetzungen |
| ATE141803T1 (de) * | 1988-08-04 | 1996-09-15 | Ciba Geigy Ag | Verfahren zur konservierung ophthalmischer lösungen und zusammensetzungen dafür |
| US4960799A (en) * | 1988-09-13 | 1990-10-02 | Ciba-Geigy Corporation | Stabilized aqueous solutions of pharmaceutically acceptable salts of ortho-(2,6-dichlorophenyl)-aminophenylacetic acid for opthalmic use |
| US5075104A (en) * | 1989-03-31 | 1991-12-24 | Alcon Laboratories, Inc. | Ophthalmic carboxy vinyl polymer gel for dry eye syndrome |
| US5034556A (en) * | 1989-04-03 | 1991-07-23 | Ppg Industries, Inc. | Reaction products of alpha-aminomethylene phosphonic acids and epoxy compounds and their use in coating compositions |
| US5300296A (en) * | 1989-11-06 | 1994-04-05 | Frank J. Holly | Antimicrobial agent for opthalmic formulations |
| JP3008131B2 (ja) * | 1990-11-14 | 2000-02-14 | ロレアル | グリセリンから誘導される非イオン両親媒性化合物、その調製方法、相応する中間体化合物及び前記化合物を含有する組成物 |
| EP0564510A1 (en) * | 1990-12-27 | 1993-10-13 | Allergan, Inc | Method and composition for disinfecting contact lenses |
| JP3107873B2 (ja) * | 1991-09-26 | 2000-11-13 | ユニ・チャーム株式会社 | 高吸水性ポリマーの経時着色防止方法および経時着色防止剤 |
| ES2087437T3 (es) * | 1991-11-26 | 1996-07-16 | Eniricerche Spa | Composicion gelificable acuosa que contiene un agente antisineresis. |
| JP2873530B2 (ja) * | 1991-12-13 | 1999-03-24 | 参天製薬株式会社 | ニュートン型粘性を示すカルボキシビニルポリマー含有点眼液基剤 |
| DE4209722C3 (de) * | 1992-03-25 | 1997-06-19 | Medproject Pharma Entwicklungs | Tropfbares Gel für die Augenheilkunde |
| SE500660C2 (sv) * | 1992-12-03 | 1994-08-01 | Mo Och Domsjoe Ab | Förfarande för framställning av grönlut vid kemikalieåtervinning i sulfat- och sulfitmassafabriker |
| US5340572A (en) * | 1993-02-08 | 1994-08-23 | Insite Vision Incorporated | Alkaline ophthalmic suspensions |
| DE59407521D1 (de) * | 1993-08-10 | 1999-02-04 | Ciba Geigy Ag | Mercerisiernetzmittel |
| FR2726762B1 (fr) * | 1994-11-10 | 1997-01-17 | Oreal | Composition cosmetique ou dermatologique sous forme d'une dispersion d'une phase huileuse dans une phase aqueuse stabilisee a l'aide de particules de gel cubique et son procede d'obtention |
| US5603929A (en) * | 1994-11-16 | 1997-02-18 | Alcon Laboratories, Inc. | Preserved ophthalmic drug compositions containing polymeric quaternary ammonium compounds |
-
1995
- 1995-06-22 US US08/493,761 patent/US5683993A/en not_active Expired - Lifetime
- 1995-12-27 TW TW084113926A patent/TW358109B/zh not_active IP Right Cessation
-
1996
- 1996-06-12 DK DK96922797T patent/DK0833609T3/da active
- 1996-06-12 EP EP96922797A patent/EP0833609B1/en not_active Expired - Lifetime
- 1996-06-12 ES ES96922797T patent/ES2167581T3/es not_active Expired - Lifetime
- 1996-06-12 AU AU63551/96A patent/AU715686B2/en not_active Ceased
- 1996-06-12 CA CA002222646A patent/CA2222646C/en not_active Expired - Fee Related
- 1996-06-12 PT PT96922797T patent/PT833609E/pt unknown
- 1996-06-12 AT AT96922797T patent/ATE208189T1/de active
- 1996-06-12 DE DE69616791T patent/DE69616791T2/de not_active Expired - Lifetime
- 1996-06-12 WO PCT/EP1996/002539 patent/WO1997000669A1/en not_active Ceased
- 1996-06-12 JP JP50343097A patent/JP4260881B2/ja not_active Expired - Fee Related
-
1997
- 1997-05-27 US US08/863,855 patent/US5858996A/en not_active Expired - Lifetime
-
2003
- 2003-04-30 CY CY0300035A patent/CY2323B1/xx unknown
-
2008
- 2008-03-21 JP JP2008072839A patent/JP2008248246A/ja active Pending
-
2012
- 2012-04-09 JP JP2012088780A patent/JP2012153710A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008248246A (ja) | 2008-10-16 |
| TW358109B (en) | 1999-05-11 |
| US5683993A (en) | 1997-11-04 |
| JP4260881B2 (ja) | 2009-04-30 |
| JP2012153710A (ja) | 2012-08-16 |
| DK0833609T3 (da) | 2002-02-18 |
| AU715686B2 (en) | 2000-02-10 |
| JPH11510480A (ja) | 1999-09-14 |
| DE69616791D1 (de) | 2001-12-13 |
| PT833609E (pt) | 2002-04-29 |
| DE69616791T2 (de) | 2002-05-29 |
| WO1997000669A1 (en) | 1997-01-09 |
| US5858996A (en) | 1999-01-12 |
| EP0833609B1 (en) | 2001-11-07 |
| CY2323B1 (en) | 2003-11-14 |
| ES2167581T3 (es) | 2002-05-16 |
| ATE208189T1 (de) | 2001-11-15 |
| AU6355196A (en) | 1997-01-22 |
| CA2222646A1 (en) | 1997-01-09 |
| EP0833609A1 (en) | 1998-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2222646C (en) | Compositions and methods for stabilizing polymers | |
| EP0844868B1 (en) | Compositions including O-carboxymethyl chitosan and use in ophthalmics | |
| CA2087420C (en) | Ophthalmic pharmaceutical composition containing n-acetyl-cisteine and polyvinylalcohol | |
| AU756000B2 (en) | Method for stabilizing pharmaceutical compositions by special use of an antioxidant | |
| EP1480677B1 (en) | Composition for stabilizing hyaluronic acid | |
| SK140297A3 (en) | Composition usable in ophthalmic surgery | |
| US20060100173A1 (en) | Ophthalmic solution | |
| EP1372628A2 (de) | Lagerstabile fertiginfusionslösungen des paracetamols | |
| Saettone et al. | Muco-adhesive liquid ophthalmic vehicles-evaluation of macromolecular ionic complexes of pilocarpine | |
| WO1993002663A1 (en) | Ophthalmic compositions based on polyhydric alcohols | |
| US5662919A (en) | Sulfated polyvinyl alcohol polymers to stabilize pharmaceutical drug compounds | |
| JPH02164829A (ja) | ヒアルロン酸点眼液 | |
| CA2179419C (en) | Sulfated polyvinyl alcohol polymers to stabilize pharmaceutical drug compounds | |
| EP0342297A1 (en) | Aqueous solution with low surface tension forming a wettable layer over a hydrophobic surface | |
| HK1030748B (en) | Dexamethasone gel | |
| HK1030748A1 (en) | Dexamethasone gel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140612 |