OA10570A - Ophtalmic solution based on diclofenac and tobramycin and its applications - Google Patents

Ophtalmic solution based on diclofenac and tobramycin and its applications Download PDF

Info

Publication number: OA10570A
Authority: OA; OAPI
Prior art keywords: agent; optionally; tobramycin; diclofenac; solution according
Prior art date: 1994-05-17

Application number

OA60766A

Other languages

English (en)

Inventor

Antonio Lopez Cabrera

Gemma Torrela Cabello

Alberto Jose Vallet Mas

Michael Van Wie Bergamini

Original Assignee

Laboratiorios Cusi S A

Priority date (The priority date 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 date listed.)

1994-05-17

Filing date

1996-01-17

Publication date

2002-06-20

1996-01-17 Application filed by Laboratiorios Cusi S A filed Critical Laboratiorios Cusi S A

2002-06-20 Publication of OA10570A publication Critical patent/OA10570A/en

Links

229960001259 diclofenac Drugs 0.000 title claims abstract description 22
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 title claims abstract description 22
229960000707 tobramycin Drugs 0.000 title claims description 47
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[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@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 title claims description 45
239000003755 preservative agent Substances 0.000 claims abstract description 15
208000015181 infectious disease Diseases 0.000 claims abstract description 11
230000004054 inflammatory process Effects 0.000 claims abstract description 10
206010061218 Inflammation Diseases 0.000 claims abstract description 9
239000002738 chelating agent Substances 0.000 claims abstract description 5
239000002904 solvent Substances 0.000 claims abstract description 5
239000000017 hydrogel Substances 0.000 claims abstract description 4
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
238000011282 treatment Methods 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 44
238000009472 formulation Methods 0.000 claims description 37
239000000243 solution Substances 0.000 claims description 31
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
239000011780 sodium chloride Substances 0.000 claims description 9
239000002997 ophthalmic solution Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
-1 Poly(N-vinylpyrrolidone) Polymers 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
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 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
OBFSQMXGZIYMMN-UHFFFAOYSA-N 3-chloro-2-hexadecylpyridine Chemical compound CCCCCCCCCCCCCCCCC1=NC=CC=C1Cl OBFSQMXGZIYMMN-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
239000004475 Arginine Substances 0.000 claims description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims description 2
229920002125 Sokalan® Polymers 0.000 claims description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
238000013016 damping Methods 0.000 claims description 2
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 claims description 2
PDTFCHSETJBPTR-UHFFFAOYSA-N phenylmercuric nitrate Chemical compound [O-][N+](=O)O[Hg]C1=CC=CC=C1 PDTFCHSETJBPTR-UHFFFAOYSA-N 0.000 claims description 2
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 2
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical group CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
235000011152 sodium sulphate Nutrition 0.000 claims description 2
239000000600 sorbitol Substances 0.000 claims description 2
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical class [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
229940079593 drug Drugs 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 claims 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
239000004372 Polyvinyl alcohol Substances 0.000 claims 1
150000001860 citric acid derivatives Chemical class 0.000 claims 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
229960005323 phenoxyethanol Drugs 0.000 claims 1
229940096826 phenylmercuric acetate Drugs 0.000 claims 1
229920002451 polyvinyl alcohol Polymers 0.000 claims 1
KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
230000003993 interaction Effects 0.000 description 10
238000001914 filtration Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000003242 anti bacterial agent Substances 0.000 description 8
239000000306 component Substances 0.000 description 8
ZGTMUACCHSMWAC-UHFFFAOYSA-N disodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid Chemical compound [Na+].[Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O ZGTMUACCHSMWAC-UHFFFAOYSA-N 0.000 description 8
235000002639 sodium chloride Nutrition 0.000 description 8
239000002260 anti-inflammatory agent Substances 0.000 description 7
230000003115 biocidal effect Effects 0.000 description 7
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
235000010338 boric acid Nutrition 0.000 description 7
239000004327 boric acid Substances 0.000 description 7
229960002645 boric acid Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
229940054534 ophthalmic solution Drugs 0.000 description 6
239000000047 product Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 5
229940121363 anti-inflammatory agent Drugs 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000005755 formation reaction Methods 0.000 description 5
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
229920004914 octoxynol-40 Polymers 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
229910021538 borax Inorganic materials 0.000 description 3
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 3
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 description 3
238000002329 infrared spectrum Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229940068968 polysorbate 80 Drugs 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
239000004328 sodium tetraborate Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000047703 Nonion Species 0.000 description 2
208000037273 Pathologic Processes Diseases 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940126575 aminoglycoside Drugs 0.000 description 2
229940124599 anti-inflammatory drug Drugs 0.000 description 2
229960003957 dexamethasone Drugs 0.000 description 2
206010014801 endophthalmitis Diseases 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
229960000905 indomethacin Drugs 0.000 description 2
229960004752 ketorolac Drugs 0.000 description 2
OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
229920002113 octoxynol Polymers 0.000 description 2
229940066429 octoxynol Drugs 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
229940068977 polysorbate 20 Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 2
229940066675 ricinoleate Drugs 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
YDEWSOMDUFRHFE-UHFFFAOYSA-N 2-amino-2-(2,6-dichlorophenyl)-2-phenylacetic acid Chemical compound ClC=1C=CC=C(Cl)C=1C(C(O)=O)(N)C1=CC=CC=C1 YDEWSOMDUFRHFE-UHFFFAOYSA-N 0.000 description 1
101100459438 Caenorhabditis elegans nac-1 gene Proteins 0.000 description 1
208000002177 Cataract Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000950314 Figura Species 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
208000002847 Surgical Wound Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
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239000003470 adrenal cortex hormone Substances 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000003515 anti-microbian Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
229960001716 benzalkonium Drugs 0.000 description 1
CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
238000013461 design Methods 0.000 description 1
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 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000006196 drop Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
230000009881 electrostatic interaction Effects 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
229940023064 escherichia coli Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
XMCTYDOFFXSNQJ-UHFFFAOYSA-N hexadecyl(methyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[NH2+]C XMCTYDOFFXSNQJ-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
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229960004384 ketorolac tromethamine Drugs 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
229940045505 klebsiella pneumoniae Drugs 0.000 description 1
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230000002535 lyotropic effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000000693 micelle Substances 0.000 description 1
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125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- 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
- 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
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Ophthalmology & Optometry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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OA60766A 1994-05-17 1996-01-17 Ophtalmic solution based on diclofenac and tobramycin and its applications OA10570A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES09401078A ES2079320B1 (es)	1994-05-17	1994-05-17	Disolucion oftalmica a base de un diclofenaco y tobramicina y sus aplicaciones.

Publications (1)

Publication Number	Publication Date
OA10570A true OA10570A (en)	2002-06-20

Family

ID=8286285

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60766A OA10570A (en)	1994-05-17	1996-01-17	Ophtalmic solution based on diclofenac and tobramycin and its applications

Country Status (20)

Country	Link
US (1)	US5597560A (es)
EP (1)	EP0711546B1 (es)
KR (1)	KR100353377B1 (es)
CN (1)	CN1098678C (es)
AT (1)	ATE198417T1 (es)
AU (1)	AU696853B2 (es)
BG (1)	BG100289A (es)
BR (1)	BR9407330A (es)
CA (1)	CA2167383C (es)
DE (1)	DE69426529T2 (es)
DK (1)	DK0711546T3 (es)
ES (1)	ES2079320B1 (es)
FI (1)	FI116884B (es)
GR (1)	GR3035633T3 (es)
HU (1)	HUT74164A (es)
NO (1)	NO308645B1 (es)
OA (1)	OA10570A (es)
PL (1)	PL312615A1 (es)
PT (1)	PT711546E (es)
WO (1)	WO1995031179A1 (es)

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1994
- 1994-05-17 ES ES09401078A patent/ES2079320B1/es not_active Expired - Fee Related
- 1994-09-07 EP EP94926248A patent/EP0711546B1/en not_active Expired - Lifetime
- 1994-09-07 AU AU76160/94A patent/AU696853B2/en not_active Ceased
- 1994-09-07 PT PT94926248T patent/PT711546E/pt unknown
- 1994-09-07 PL PL94312615A patent/PL312615A1/xx unknown
- 1994-09-07 CA CA002167383A patent/CA2167383C/en not_active Expired - Fee Related
- 1994-09-07 KR KR1019960700285A patent/KR100353377B1/ko not_active Expired - Fee Related
- 1994-09-07 DE DE69426529T patent/DE69426529T2/de not_active Expired - Fee Related
- 1994-09-07 WO PCT/ES1994/000084 patent/WO1995031179A1/es not_active Ceased
- 1994-09-07 HU HU9600095A patent/HUT74164A/hu unknown
- 1994-09-07 BR BR9407330A patent/BR9407330A/pt not_active Application Discontinuation
- 1994-09-07 CN CN94193294A patent/CN1098678C/zh not_active Expired - Fee Related
- 1994-09-07 AT AT94926248T patent/ATE198417T1/de not_active IP Right Cessation
- 1994-09-07 DK DK94926248T patent/DK0711546T3/da active
1995
- 1995-04-10 US US08/419,387 patent/US5597560A/en not_active Expired - Lifetime
1996
- 1996-01-17 BG BG100289A patent/BG100289A/xx unknown
- 1996-01-17 FI FI960232A patent/FI116884B/fi active IP Right Grant
- 1996-01-17 NO NO960207A patent/NO308645B1/no not_active IP Right Cessation
- 1996-01-17 OA OA60766A patent/OA10570A/en unknown
2001
- 2001-03-23 GR GR20010400478T patent/GR3035633T3/el unknown

Also Published As

Publication number	Publication date
HK1017806A1 (en)	1999-11-26
US5597560A (en)	1997-01-28
ES2079320A1 (es)	1996-01-01
DK0711546T3 (da)	2001-04-23
AU696853B2 (en)	1998-09-17
CA2167383C (en)	2001-11-20
CN1098678C (zh)	2003-01-15
NO960207D0 (no)	1996-01-17
CA2167383A1 (en)	1995-11-23
PL312615A1 (en)	1996-04-29
EP0711546A1 (en)	1996-05-15
AU7616094A (en)	1995-12-05
FI116884B (fi)	2006-03-31
FI960232A0 (fi)	1996-01-17
DE69426529T2 (de)	2001-08-09
NO308645B1 (no)	2000-10-09
KR100353377B1 (ko)	2002-12-26
HUT74164A (en)	1996-11-28
GR3035633T3 (en)	2001-06-29
PT711546E (pt)	2001-06-29
BG100289A (bg)	1996-12-31
WO1995031179A1 (es)	1995-11-23
FI960232L (fi)	1996-03-15
NO960207L (no)	1996-03-15
ES2079320B1 (es)	1996-10-16
EP0711546B1 (en)	2001-01-03
ATE198417T1 (de)	2001-01-15
CN1130351A (zh)	1996-09-04
DE69426529D1 (de)	2001-02-08
BR9407330A (pt)	1996-06-18
KR960703581A (ko)	1996-08-31

Publication	Publication Date	Title
OA10570A (en)	2002-06-20	Ophtalmic solution based on diclofenac and tobramycin and its applications
US5414011A (en)	1995-05-09	Preservative system for ophthalmic formulations
US5110493A (en)	1992-05-05	Ophthalmic NSAID formulations containing a quaternary ammonium preservative and a nonionic surfactant
EP0592348B1 (en)	1998-01-07	Pharmaceutical formulation comprised of polymyxin-trimethoprim and an anti-inflammatory drug for ophthalmic and optic topical use
JP2769253B2 (ja)	1998-06-25	水性液剤
US9114168B2 (en)	2015-08-25	Pharmaceutical compositions containing a fluoroquinolone antibiotic drug
HU199072B (en)	1990-01-29	Antimicrobal conserving composition and process for production of compositions for oculist purpuses
AU5302699A (en)	2000-03-14	Aqueous liquid preparations
EP2785328A1 (en)	2014-10-08	Novel slow-releasing ophthalmic compositions comprising povidone iodine
JPH069383A (ja)	1994-01-18	Ｎ−アセチル−システイン及びポリビニルアルコールを含有する眼医薬組成物
AU2002322002B2 (en)	2007-01-25	Quinolone carboxylic acid compositions and related methods of treatment
KR20010012521A (ko)	2001-02-15	방부 조성물
AU2002322002A1 (en)	2003-05-15	Quinolone carboxylic acid compositions and related methods of treatment
CA3197797A1 (en)	2022-05-12	Ophthalmic composition containing levofloxacin and ketorolac, method for the preparation and use thereof
EP0082546B2 (en)	1992-03-25	Pharmaceutical mixture and method for making the mixture
Kramer et al.	2002	Formulation requirements for the ophthalmic use of antiseptics
EP0212927B1 (en)	1991-10-23	Pharmaceutical composition comprising sodium cromoglycate and a mucolytic agent
EA051764B1 (ru)	2025-12-04	Офтальмологическая композиция, содержащая левофлоксацин и кеторолак, способ ее получения и ее применение
HK1017806B (en)	2001-07-20	Ophthalmic solution based on diclofenac and tobramcine and its applications
HK1063721B (en)	2014-06-20	Quinolone carboxylic acid compositions and related methods of treatment