EP1830803A2 - Arzneimittel zur hygienischen applikation im ohr - Google Patents
Arzneimittel zur hygienischen applikation im ohrInfo
- Publication number
- EP1830803A2 EP1830803A2 EP05816509A EP05816509A EP1830803A2 EP 1830803 A2 EP1830803 A2 EP 1830803A2 EP 05816509 A EP05816509 A EP 05816509A EP 05816509 A EP05816509 A EP 05816509A EP 1830803 A2 EP1830803 A2 EP 1830803A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- medicament
- medicament according
- weight
- pharmaceutical formulation
- 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.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims abstract description 28
- 241001465754 Metazoa Species 0.000 claims abstract description 15
- 229960001248 pradofloxacin Drugs 0.000 claims description 25
- 229960004022 clotrimazole Drugs 0.000 claims description 23
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 23
- 239000000725 suspension Substances 0.000 claims description 20
- LZLXHGFNOWILIY-APPDUMDISA-N pradofloxacin Chemical compound C12=C(C#N)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 LZLXHGFNOWILIY-APPDUMDISA-N 0.000 claims description 17
- AKUJBENLRBOFTD-HIBZCRSPSA-N [2-[(9r,10s,11s,13s,16r,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)C1C1C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O AKUJBENLRBOFTD-HIBZCRSPSA-N 0.000 claims description 16
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 11
- 235000010199 sorbic acid Nutrition 0.000 claims description 11
- 239000004334 sorbic acid Substances 0.000 claims description 11
- 229940075582 sorbic acid Drugs 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
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- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 claims description 8
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims description 8
- 229960002206 bifonazole Drugs 0.000 claims description 8
- 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 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
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- BPFYOAJNDMUVBL-UHFFFAOYSA-N LSM-5799 Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3N(C)COC1=C32 BPFYOAJNDMUVBL-UHFFFAOYSA-N 0.000 claims description 5
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- 239000004599 antimicrobial Substances 0.000 claims description 5
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- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone 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-DVTGEIKXSA-N 0.000 claims description 5
- 229960002531 marbofloxacin Drugs 0.000 claims description 5
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- 239000002543 antimycotic Substances 0.000 claims description 4
- 229960003957 dexamethasone Drugs 0.000 claims description 4
- 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 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000013583 drug formulation Substances 0.000 claims description 2
- 229960002509 miconazole Drugs 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 2
- 229960003600 silver sulfadiazine Drugs 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 229960005294 triamcinolone Drugs 0.000 claims description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 239000007788 liquid Substances 0.000 claims 1
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- -1 aminoglycosides Chemical class 0.000 description 37
- 238000009472 formulation Methods 0.000 description 33
- 229910021485 fumed silica Inorganic materials 0.000 description 20
- 229940057917 medium chain triglycerides Drugs 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 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
- 239000004480 active ingredient Substances 0.000 description 7
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- 150000004677 hydrates Chemical class 0.000 description 7
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000014655 lactic acid Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- DPHFJXVKASDMBW-RQRKFSSASA-N [2-[(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;hydrate Chemical compound O.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O DPHFJXVKASDMBW-RQRKFSSASA-N 0.000 description 5
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- 229960002117 triamcinolone acetonide Drugs 0.000 description 5
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical group C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 5
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229960002794 prednicarbate Drugs 0.000 description 1
- FNPXMHRZILFCKX-KAJVQRHHSA-N prednicarbate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CC)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O FNPXMHRZILFCKX-KAJVQRHHSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960002800 prednisolone acetate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000003306 quinoline derived antiinfective agent Substances 0.000 description 1
- 229950007734 sarafloxacin Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 229960004954 sparfloxacin Drugs 0.000 description 1
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 description 1
- 229960000268 spectinomycin Drugs 0.000 description 1
- UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 description 1
- 235000019372 spiramycin Nutrition 0.000 description 1
- 229960001294 spiramycin Drugs 0.000 description 1
- 229930191512 spiramycin Natural products 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229960004576 temafloxacin Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- 229960000223 tilmicosin Drugs 0.000 description 1
- JTSDBFGMPLKDCD-XVFHVFLVSA-N tilmicosin Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CCN1C[C@H](C)C[C@H](C)C1)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@@H]1O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]1O JTSDBFGMPLKDCD-XVFHVFLVSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229950008187 tosufloxacin Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
- 235000019375 tylosin Nutrition 0.000 description 1
- JATLJHBAMQKRDH-UHFFFAOYSA-N vebufloxacin Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CCC3=C1N1CCN(C)CC1 JATLJHBAMQKRDH-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- 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
- A61K9/0046—Ear
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
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- A61D—VETERINARY INSTRUMENTS, IMPLEMENTS, TOOLS, OR METHODS
- A61D7/00—Devices or methods for introducing solid, liquid, or gaseous remedies or other materials into or onto the bodies of animals
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines having two or more nitrogen atoms in the same ring, e.g. oxadiazines
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/16—Otologicals
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/10—Antimycotics
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A—HUMAN NECESSITIES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M31/00—Devices for introducing or retaining media, e.g. remedies, in cavities of the body
Definitions
- the invention relates to a system as a medicament for the hygienic application of an ear medication - especially in animals - which is reproducible even at low volumes and which is not ejected even when shaking the head again.
- causes of the complex disease in the dog is usually a combination of predisposing factors (eg lop-eared ears, strong earwax production), primary factors (underlying disease such as atopy or food allergy, seborrhoea) and preserving factors (bacterial and yeast propagation in the ear canal), in a circulus vitiosus from microbial growth on the one hand and inflammation on the other.
- predisposing factors eg lop-eared ears, strong earwax production
- primary factors underlying disease such as atopy or food allergy, seborrhoea
- preserving factors bacterial and yeast propagation in the ear canal
- the treatment of otitis occurs after diagnosis and initial therapy by the veterinarian usually by the owner.
- the object of the invention was therefore to find a drug that allows the dosing accurate, hygienic and easy treatment of the ear.
- thixotropic formulations are described in these documents, they are taken either orally as capsules orally, thereby ensuring reproducible dosing, or the agents are filled in larger containers with higher proportions of active ingredient (FR 2790200) also a reproducible dosage considerably easier.
- the restoring force in the descriptions of the thixotropic formulations is solely for the purpose of filling the capsules, but not the specific application at the patient's ear (WO 00/01371).
- the subject of the invention is therefore:
- a medicament for the treatment of diseases of the ear in humans or animals comprising:
- Anti-infective agents are in particular antibacterial compounds such as penicillins, cephalosporins, aminoglycosides, sulfonamides and especially quinolones.
- Quinolones preferably fluoroquinolones, include compounds as disclosed in the following documents: US 4,670,444 (Bayer AG), US 4,472,405 (Riker Labs), US 4,730,000 (Abbott), US 4,861,779 (Pfizer U.S. 4,382,892 (Daiichi), U.S.
- fluoroquinolones are those of the formula (I) or (IT):
- X is hydrogen, halogen, Ci. 4- alkyl, C 1-4 -alkoxy, NH 2 ,
- R 4 is optionally substituted by hydroxy or methoxy straight or branched Ci-Gi-alkyl, cyclopropyl, acyl having 1 to 3 carbon atoms,
- R 5 is hydrogen, methyl, phenyl, thienyl or pyridyl
- R 6 is hydrogen or C M -alkyl
- R 7 is hydrogen or Ci -4 -alkyl
- R 8 is hydrogen or Ci -4 -alkyl
- R 1 is an alkyl radical having 1 to 3 carbon atoms, cyclopropyl, 2-fluoroethyl, methoxy, 4-fluorophenyl, 2,4-difluorophenyl or methylamino,
- R 2 is hydrogen or optionally methoxy or 2-methoxyethoxy-substituted alkyl having 1 to 6 carbon atoms and cyclohexyl, benzyl, 2-oxopropyl, phenacyl, ethoxycarbonylmethyl, pivaloyloxymethyl,
- R 3 is hydrogen, methyl or ethyl
- the compounds of formulas (I) and (IT) may be in the form of their racemates or in enantiomeric forms.
- R 1 is optionally halogen-substituted C 1 -C 6 -alkyl or cyclopropyl
- R is 2-4 I stands for hydrogen or alkyl C Y for residues of the structures
- R 4 represents optionally hydroxyl-substituted straight or branched C r C 3 alkyl, oxalkyl having 1 to 4 carbon atoms,
- R 5 is hydrogen, methyl or phenyl
- R 7 is hydrogen or methyl
- R 6 and R 8 are hydrogen
- R! represents cyclopropyl
- R 2 is hydrogen, methyl or ethyl
- R 4 is methyl, optionally substituted by hydroxy ethyl, R 5 is hydrogen or methyl,
- R 7 is hydrogen or methyl
- R 6 and R 8 are hydrogen
- Suitable salts are pharmaceutically usable acid addition salts and basic salts.
- Examples of pharmaceutically usable salts are the salts of hydrochloric acid, sulfuric acid, acetic acid, glycolic acid, lactic acid, succinic acid, citric acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, galacturonic acid, gluconic acid, embonic acid, glutamic acid or aspartic acid.
- the compounds according to the invention can be bound to acidic or basic ion exchangers.
- Suitable pharmaceutically usable basic salts are the alkali metal salts, for example the sodium or potassium salts, the alkaline earth metal salts, for example the magnesium or calcium salts; the zinc salts, the silver salts and the guanidinium s' Alze called.
- Hydrates are understood as meaning both the hydrates of the fluoroquinolones themselves and the hydrates of their salts.
- fluoroquinolones which may be mentioned are the compounds described in WO 97/31001, in particular 8-cyano-1-cyclopropyl-7 - ((1S, 6S) -2,8-diazabicyclo [4.3.0] nonan-8-yl) 6-fluoro-l, 4-dihydro-4-oxo-3-quinolinecarboxylic acid (pradofloxacin) having the formula
- Pradofloxacin is preferred in its free form as anhydrate, e.g. In modification B (see WO 00/31076) or as trihydrate (cf., WO 2005/097789).
- the preferred quinolone anti-infective agents are marbofloxacin, orbifloxacin, difloxacin and ibafloxacin.
- Penicillins are e.g. Benzylpenicillin, ampicillin, amoxicillin, oxacillin, piperacillin, ticarcillin.
- Cephalosporins are z. B. Ceefalexin, Cefadroxil, Cefazolin, Cefoxitin, Ceftiofur.
- macrolide is e.g. called erythromycin, spiramycin, tylosin, tilmicosin.
- sulfonamides are, for example: called trimethoprim and " sulfadiazine " (preferably used in Kömbinuschiün).
- aminoglycosides may be mentioned gentamicin, kanamycin, streptomycin, neomycin and spectinomycin.
- antibiotic Lmcosamid called clindamycin.
- the anti-infective agent is typically used in the formulation in an amount of 0.001-6% by weight, preferably 0.01-1.0% by weight, particularly preferably 0.1-0.8% by weight.
- anti-infective agents in the context of this invention are derived from silver, z.
- colloidal silver silver nitrate or silver sulfadiazine.
- these may be used in combination with one of the anti-infective agents described above and / or, as described below, optionally a corticosteroid.
- the drug according to the invention in addition to the anti-infective as another pharmaceutically active ingredient contains an antimycotic, such.
- an imidazole or a triazole in particular z. Clotrimazole, miconazole or bifonazole.
- the antimycotic agent is typically used in the formulation in a proportion of 0.01-10% by weight, preferably 0.1-5% by weight, particularly preferably 0.5-2% by weight. Furthermore, it is advantageous if the medicament according to the invention also contains a corticoid in addition to the anti-infective and optionally the antimycotic. It can be used both the corticosteroids and their derivatives usually used for pharmaceutical purposes, in particular the esters. Examples of corticosteroids are hydrocortisone, prednisolone, betamethasone, mometasone, flumethasone; preferred betamethasone, triamcinolone and especially dexamethasone called.
- the hydroxyl groups on C17 and / or C21 are usually esterified with short-chain organic acids, this increases the potency of the corticosteroids, the higher lipophilicity leads to a better penetration into the cells and at the same time the accumulation in the skin is improved.
- Hydrocortisone for example, is one of the weakest, while hydrocortisone 17-butyrate is one of the strong glucocorticoids. Similar effects are to be expected with the glucocorticoids dexamethasone / dexamethasone 21-acetate and betamethasone / betamethasone 17-valerate.
- Korticoidester are Aclometasonpropionat, beta methasondipropionat, hexanoate betamethasone, clobetasol propionate, clobetasone, Clocortolon-, Clocortolonpivalat, Dexamethasonaceatat, diflucortolone, diflucortolone, flumetasone, Fluocortolonhexanoat, fluocortolone pivalate, fluprednidene, fluticasone propionate, buteprat hydrocortisone, hydrocortisone aceponate, hydrocortisone acetate, hydrocortisone, Methylprednisolone aceponate, mometasone furoate, prednicarbate and prednisolone acetate.
- corticoid esters are betamethasone-17-valerate and especially dexamethasone-21-acetate.
- Another particularly preferred example of a corticosteroid derivative is triamcinolone acetonide, a ketal.
- corticoid in its broadest sense also encompasses derivatives such as the esters and ketals detailed above.
- the corticoid is typically used in the formulation in a proportion of 0.001-2.0% by weight, preferably 0.005-0.5% by weight, particularly preferably 0.05-0.2% by weight.
- pradofloxacin a particularly preferred active ingredient combination
- clotrimazole a particularly preferred active ingredient combination
- dexamethasone preferably in the form of its 21-acetate
- Optically active substances can be used in the form of their stereoisomers or as a mixture of stereoisomers, for example as pure or enriched enantiomers or as racemates.
- the fluid base may be oily or aqueous.
- natural (animal or vegetable), synthetic and semi-synthetic oils or fats can be used. These include soybean, sunflower, cottonseed, olive, peanut, safflower, palm, rapeseed, coconut, corn germ, castor and jojoba oils.
- medium-chain triglycerides triglycerides with saturated fatty acids, preferably the octane and decanoic acid
- propylene glycol diesters of caprylic / capric acid low-viscosity paraffin or sesame oil
- particularly preferably used are the medium-chain triglycerides and propylene glycol diesters of caprylic / capric acid.
- these oils and fats can also be used as mixtures.
- aqueous base water, glycerin, propylene glycol or polyethylene glycols can be used. Mixtures of these substances are also usable.
- An oily foundation is preferred.
- the oily or aqueous base is typically used in an amount of 99.9-72% by weight, preferably 99.4-89.5% by weight, more preferably 97.9-94.0% by weight. used.
- a fluid drug formulation is filled in a primary packaging.
- the formulations may in principle be solutions, emulsions, suspensions, pastes or gels.
- the formulations may contain thickening agents, e.g. Cellulose derivatives such as methylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose,
- Carboxymethyl cellulose microcrystalline cellulose; Bentonites, kaolin, pectin, starches, modified starches, waxes, agar, paraffins, gelatin, alginates, polyvinylpyrrolidone,
- Crospovidone cetyl alcohol, stearates such as magnesium stearate, zinc stearate or glyceryl stearate, saturated or unsaturated long-chain fatty acids (C 8 -C 2) , high molecular weight polyethylene glycols (eg polyethylene glycol 2000) or preferably silicas such as hydrophilic, precipitated, highly dispersed, precompressed or hydrophobic, methylated silicas and mixed oxides
- Silica and alumina and more preferably fumed silicas.
- thickeners is z. B. advantageous if one or more active ingredients do not dissolve sufficiently or in the fluid base, so that a suspension must be used.
- the thickener then serves to stabilize the suspension against sedimentation.
- the thickener is used in the formulations typically in a proportion of 0.1 to 10 wt .-%, preferably 0.5 to 5 wt .-%, particularly preferably 1.0 to 3.0 wt .-%.
- the formulation is adjusted to have thixotropic properties, that is, it becomes thinner by agitation, and at rest the viscosity rebuilds.
- Thixotropic formulations are prepared by adding a corresponding additive to the formulation base (fluid base) insofar as the fluid base is not itself thixotropic.
- a suspension stabilizer or thickener such as e.g. the fumed silicas or hydrophobic silica (eg, methylated silica).
- the degree of thixotropy can be adjusted by varying the concentration.
- the primary packaging means according to the invention are single dose containers. These are filled with a volume of 0.1-5.0 ml, preferably 0.2-4.0 ml, particularly preferably 0.3-2.0 ml of removable content of fluid formulation.
- the formulations may contain other customary, pharmaceutically acceptable additives and auxiliaries. As examples may be mentioned
- Preservatives such as carboxylic acids (sorbic acid, propionic acid, benzoic acid, lactic acid), phenols (cresols, p-hydroxybenzoic acid esters such as methylparaben,
- Propylparaben, etc. aliphatic alcohols (benzyl alcohol, ethanol, butanol, etc.), quaternary ammonium compounds (benzalkonium chloride, cetylpyridinium chloride)
- Antioxidants such as sulfites (Na sulfite, Na-metabisulfite), organic sulfides (cystine, cysteine, cysteamine, methionine, thioglycerol, thioglycolic acid, thiolactic acid) phenols (tocopherols, as well as vitamin E and vitamin E TPGS ( d-alpha-tocopherylpolyethylene glycol 1000 succinate), butylhydroxyanisole, butylhydroxytoluene, gallic acid or its derivatives (propyl, octyl and dodecyl gallate), organic acids (ascorbic acid, citric acid, tartaric acid, lactic acid) and their salts and esters ,
- sulfites Na sulfite, Na-metabisulfite
- organic sulfides cystine, cysteine, cysteamine, methionine, thioglycerol, thiogly
- Wetting agents or emulsifiers for example fatty acid salts, fatty alkyl sulfates, fatty alkyl sulfonates, linear alkylbenzenesulfonates, fatty alkyl polyethylene glycol ether sulfates, fatty alkyl polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, alkyl polyglycosides, fatty acid N-methylglucamides, polysorbates, sorbitan fatty acid esters, lecithins and poloxamers. • Pharmaceutically acceptable dyes such as iron oxides, carotenoids, etc.
- the formulations may also contain co-solvents, which may also lower the viscosity. These are usually used in proportions of 0.1 to 40 wt .-%, preferably from 1 to 10 wt .-%.
- cosolvents which may be mentioned are: pharmaceutically acceptable alcohols, such as ethanol or benzyl alcohol, dimethyl sulfoxide, ethyl lactate,
- Hexyl dodecanol, decyl oleate, dibutyl adipate, dimethicone, glyceryl ricinoleate, octyldodecanol, octyl stearate, propylene glycol dipelargonate and preferably isopropyl myristate or isopropyl palmitate can be used as spreading agents.
- Penetration enhancers improve the transdermal application of drugs and are in principle known in the art (see, for example, Chapter 6 of
- spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils or their copolymers with polyethers, fatty acid esters (for example oleic acid oloxyl esters), triglycerides, fatty alcohols and linolenes.
- DMSO N-methylpyrrolidone, 2-pyrrolidone, dipropylene glycol monomethyl ether, octyldodecanol, oleylmacrogol glycerides or propylene glycolollaurate may also be used.
- acids are basically inorganic and organic acids in question.
- inorganic acids are hydrochloric acid, sulfuric acid, sulfurous acid and phosphoric acid.
- organic acids are formic acid, acetic acid, propionic acid,
- the primary packaging usually has the form of a tube (tube tubes, laminate tubes, Blastuben or spray stretch tubes).
- the disposable container can be made of polypropylene, polyethylene, aluminum (Al), laminate or mixtures of these materials.
- the most common material for plastic tubes in general is currently polyethylene, namely PE-LD (polyethylene low density) and also PE-HD (high density).
- Laminate tubes are multilayer tubes made of aluminum or silicon oxide (SiOx) and plastic laminates. The composites usually consist of PE-LD / AL / PE-LD and other layers.
- the aluminum layer can also be replaced by barrier films such as thermoplastics or barrier plastics, in particular by E / V AL (EfVOH, ethylene-vinyl alcohol) and silicon oxide (SiOx).
- barrier films such as thermoplastics or barrier plastics, in particular by E / V AL (EfVOH, ethylene-vinyl alcohol) and silicon oxide (SiOx).
- Tubes of polyethylene, polypropylene or laminate, more preferably of laminate or in particular polypropylene are preferably used according to the invention.
- Specifically sterilizable polypropylene tubes provide e.g. Tubes made of PP / E / VAL / PP.
- the tubes are by Abmosh, screw or plug with or without additional sealing membrane by means of piercing membrane including mandrel, for example. in the cap, by means of peelable sealing e.g. opened in the form of a film or by means of breakable or tear-off seal.
- the tubes are screwed or screwed on e.g. in the cap Domes open in the sealing membrane of the tube.
- the tip of the applicator should also be of a certain length when opened and be rounded at the front end to prevent injuries.
- Fig. 1 shows an example of a tube according to the invention suitable as a single dose container.
- the described formulations filled in single-dose containers are particularly suitable for the hygienic treatment of otitis externa on dogs and cats. It should be emphasized in particular that the formulation can be taken in a well reproducible manner. If thickeners are used in suspension formulations, sedimentation of the suspended constituents can generally be prevented. Thixotropic formulations are particularly advantageous since, after shaking the single-dose containers, the formulation is taken out particularly well reproducibly, even with low active ingredient concentrations, the formulation is simply and hygienically applied to the animal's ear by the thixotropy and the single-dose container and yet not, for example, by the usual shaking of the head can be thrown out.
- the formulations are prepared by dispersing the active ingredients or adjuvants to be dissolved or suspended in the base. If appropriate, an agitator or preferably a homogenizer or high-pressure homogenizer is used for dispersion. The order of addition of individual ingredients may be varied depending on the formulation. After dispersing all formulation ingredients, the finished formulation is stored intermediately or filled directly into the single-dose containers, which are then sealed.
- the medicaments according to the invention are generally suitable for use in humans and animals. Preferably, they are used in livestock and animal breeding in livestock, breeding, zoo, laboratory, experimental and hobby animals, especially in mammals.
- the livestock and breeding animals include mammals such as e.g. Cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, rabbits, fallow deer, reindeer, fur animals such as e.g. Mink, chinchilla, raccoon, as well as birds such as e.g. Chickens, geese, turkeys, ducks, pigeons and ostriches.
- mammals such as e.g. Cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, rabbits, fallow deer, reindeer, fur animals such as e.g. Mink, chinchilla, raccoon, as well as birds such as e.g. Chickens, geese, turkeys, ducks, pigeons and ostriches.
- preferred farm animals are beef, sheep, pork and chicken.
- Laboratory and experimental animals include dogs, cats, rabbits and rodents such as mice, rats, guinea pigs and golden hamsters.
- the hobby animals include dogs, cats, horses, rabbits, rodents such as golden hamsters, guinea pigs, mice, reptiles, amphibians and birds for home and zoo keeping.
- the medicaments according to the invention are preferably used in pets, in particular in dogs and cats.
- the application can be both prophylactic and therapeutic.
- formulations described here are intended for local application in the ear canals. Other applications are possible but in principle such. As the dermal, oral, rectal, vaginal or nasal application. Examples
- the percentages for the formulations described herein are given by weight per volume (grams of the subject substance per 100 ml of finished formulation).
- the medium-chain triglycerides to be used are the triglycerides of the CapryW capric esters, for example Miglyol® 812 from Sasol / Witten (used, for example, in Examples 3 and 6).
- betamethasone valerate 0.5 g are suspended with 1.5 g of pradofloxacin, 5 g of bifonazole in 973 g Propylenglykoloctanoatdecanoat and then treated with 20 g of fumed silica. Subsequently, the suspension is homogenized with a homogenizer for 10 min.
- 10 g of enrofloxacin are suspended with 2 g of triamcinolone acetonide, 20 g of clotrimazole in 1932 g of medium-chain triglycerides and then mixed with 36 g of fumed silica. Subsequently, the suspension is homogenized with a homogenizer for 10 min.
- dexamethasone 21 acetate 1.0% clotrimazole 0.8% hydroxyethylcellulose 20% lactic acid 19% isopropanol
- 200 g of isopropanol and 16 g of benzyl alcohol are mixed in 500 g of propylene glycol.
- 1 g of dexamethasone acetate, 3 g of pradofloxacin and 10 g of clotrimazole are suspended therein and then treated with 200 g of lactic acid.
- 8 g of hydroxyethyl cellulose are stirred in and adjusted to the final weight with 62 g of propylene glycol. Subsequently, the suspension is homogenized with a homogenizer for 10 min.
- pradofloxacin 3 g are suspended with 0.3 g of dexamethasone acetate and 10 g of clotrimazole in 968.7 g medium-chain triglycerides and then mixed with 18 g of fumed silica. Subsequently, the suspension is homogenized with a homogenizer for 10 min.
- n-butanol 0.5 g is mixed in 241 g of medium chain triglycerides.
- 0.25 g of dexamethasone acetate, 1.25 g of enrofloxacin and 2.5 g of bifonazole are dispersed and then added to the approach with 4.5 g of fumed silica.
- the suspension is then homogenized with a homogenizer for 10 min.
- Silica are dispersed in this solution and the remaining mid-chain triglycerides (22.9 kg) added. Subsequently, the suspension is homogenized with a homogenizer for about 10 min.
- methylated silica (Aerosil® R 972, fumed silica hydrophobized with dimethyldichlorosilane from Degussa) ad 100% medium-chain triglycerides
- sorbic acid 0.5 kg of clotrimazole and 0.05 kg of dexamethasone 21 acetate are dissolved in 95.64 kg of medium-chain triglycerides. 0.114 kg of pradofloxacin trihydrate and 3.6 kg of hydrophobic silica are dispersed in this solution. Subsequently, the suspension is homogenized with a homogenizer for about 10 min.
- methylated silica (Aerosil® R 974, fumed silica hydrophobized with dimethyldichlorosilane from Degussa) ad 100% medium-chain triglycerides 0.1 kg sorbic acid, 0.5 kg clotrimazole and 0.05 kg dexamethasone 21 acetate are reported in 96, 66 kg medium-chain triglycerides dissolved. 0.114 kg of pradofloxacin trihydrate and 2.7 kg of hydrophobic silica are dispersed in this solution. Subsequently, the suspension is homogenized with a homogenizer for about 10 min.
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Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102004059220 | 2004-12-09 | ||
DE102005055385A DE102005055385A1 (de) | 2004-12-09 | 2005-11-17 | Arzneimittel zur hygienischen Applikation im Ohr |
PCT/EP2005/012978 WO2006061156A2 (de) | 2004-12-09 | 2005-12-03 | Arzneimittel zur hygienischen applikation im ohr |
Publications (1)
Publication Number | Publication Date |
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EP1830803A2 true EP1830803A2 (de) | 2007-09-12 |
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EP05816509A Withdrawn EP1830803A2 (de) | 2004-12-09 | 2005-12-03 | Arzneimittel zur hygienischen applikation im ohr |
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US (1) | US20090011045A1 (de) |
EP (1) | EP1830803A2 (de) |
JP (1) | JP2008522998A (de) |
KR (1) | KR20070086799A (de) |
AR (1) | AR052990A1 (de) |
AU (1) | AU2005313602A1 (de) |
BR (1) | BRPI0518855A2 (de) |
CA (1) | CA2594103A1 (de) |
CR (1) | CR9142A (de) |
DE (1) | DE102005055385A1 (de) |
GT (1) | GT200500361A (de) |
IL (1) | IL183744A0 (de) |
MX (1) | MX2007006689A (de) |
NO (1) | NO20073148L (de) |
NZ (1) | NZ555640A (de) |
PE (1) | PE20061145A1 (de) |
RU (1) | RU2431486C2 (de) |
TW (1) | TW200637611A (de) |
WO (1) | WO2006061156A2 (de) |
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DE102006049520A1 (de) | 2006-10-20 | 2008-04-24 | Bayer Healthcare Ag | Verfahren zur Herstellung von Pradofloxacin |
DE102007055341A1 (de) | 2007-11-19 | 2009-05-20 | Bayer Animal Health Gmbh | Stabilisierung öliger Suspensionen enthaltend hydrophobe Kieselsäuren |
GR20090100230A (el) | 2009-04-14 | 2010-11-18 | Casso Pharmaceuticals Ε.Π.Ε, | Απο του στοματος εναιωρημα οξικης δεξαμεθανοζης-συνθεση καλυψης γευσης της δεξαμεθανοζης |
EP2802209B1 (de) * | 2012-01-10 | 2020-12-02 | Entrx LLC | Ohrentherapeutische zusammensetzungen |
US9849126B2 (en) | 2013-01-03 | 2017-12-26 | Entrx LLC | Sterile otic formulations |
MD4291C1 (ro) * | 2013-12-27 | 2015-02-28 | Государственный Медицинский И Фармацевтический Университет "Nicolae Testemitanu" Республики Молдова | Preparat medicamentos pentru tratamentul otitelor |
SI3623390T1 (sl) | 2015-12-29 | 2023-12-29 | Galderma Holding SA | Mrežno povezovanje ogljikovih hidratov |
JP7033789B2 (ja) * | 2016-06-29 | 2022-03-11 | オトノミー,インク. | トリグリセリド耳用製剤とその使用 |
PE20191462A1 (es) * | 2017-02-13 | 2019-10-16 | Bayer Animal Health Gmbh | Composicion liquida que contiene pradofloxacina |
MX2020011280A (es) | 2018-04-25 | 2020-11-13 | Bayer Animal Health Gmbh | Proceso para la hidrolisis de esteres carboxilicos de quinolona. |
TWI834808B (zh) * | 2019-02-19 | 2024-03-11 | 西班牙商薩爾瓦特實驗室有限公司 | 以單劑包裝的克氯黴唑液體組成物 |
US11235087B2 (en) * | 2019-10-28 | 2022-02-01 | Galderma Holding SA | Ready-to-use esthetic compositions |
RU2758056C2 (ru) * | 2019-11-21 | 2021-10-26 | федеральное государственное бюджетное образовательное учреждение высшего образования "Ставропольский государственный аграрный университет" | Препарат для лечения отитов бактериальной и грибковой этиологии у собак |
BR112022010831A2 (pt) | 2019-12-02 | 2022-08-23 | Galderma Holding SA | Composições estéticas de alto peso molecular |
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- 2005-11-17 DE DE102005055385A patent/DE102005055385A1/de not_active Withdrawn
- 2005-12-03 NZ NZ555640A patent/NZ555640A/en not_active IP Right Cessation
- 2005-12-03 RU RU2007125570/15A patent/RU2431486C2/ru not_active IP Right Cessation
- 2005-12-03 US US11/721,204 patent/US20090011045A1/en not_active Abandoned
- 2005-12-03 BR BRPI0518855-5A patent/BRPI0518855A2/pt not_active IP Right Cessation
- 2005-12-03 KR KR1020077014903A patent/KR20070086799A/ko not_active Application Discontinuation
- 2005-12-03 EP EP05816509A patent/EP1830803A2/de not_active Withdrawn
- 2005-12-03 CA CA002594103A patent/CA2594103A1/en not_active Abandoned
- 2005-12-03 WO PCT/EP2005/012978 patent/WO2006061156A2/de active Application Filing
- 2005-12-03 JP JP2007544787A patent/JP2008522998A/ja active Pending
- 2005-12-03 AU AU2005313602A patent/AU2005313602A1/en not_active Abandoned
- 2005-12-03 MX MX2007006689A patent/MX2007006689A/es not_active Application Discontinuation
- 2005-12-07 PE PE2005001419A patent/PE20061145A1/es not_active Application Discontinuation
- 2005-12-08 TW TW094143288A patent/TW200637611A/zh unknown
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Also Published As
Publication number | Publication date |
---|---|
PE20061145A1 (es) | 2006-12-29 |
MX2007006689A (es) | 2007-08-14 |
WO2006061156A3 (de) | 2006-08-24 |
AU2005313602A1 (en) | 2006-06-15 |
JP2008522998A (ja) | 2008-07-03 |
NO20073148L (no) | 2007-08-22 |
GT200500361A (es) | 2006-11-07 |
TW200637611A (en) | 2006-11-01 |
KR20070086799A (ko) | 2007-08-27 |
DE102005055385A1 (de) | 2006-06-14 |
BRPI0518855A2 (pt) | 2008-12-09 |
CA2594103A1 (en) | 2006-06-15 |
IL183744A0 (en) | 2008-04-13 |
AR052990A1 (es) | 2007-04-18 |
US20090011045A1 (en) | 2009-01-08 |
NZ555640A (en) | 2009-12-24 |
RU2007125570A (ru) | 2009-01-20 |
RU2431486C2 (ru) | 2011-10-20 |
CR9142A (es) | 2007-12-04 |
WO2006061156A2 (de) | 2006-06-15 |
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