ZA200602071B - Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline - Google Patents
Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline Download PDFInfo
- Publication number
- ZA200602071B ZA200602071B ZA200602071A ZA200602071A ZA200602071B ZA 200602071 B ZA200602071 B ZA 200602071B ZA 200602071 A ZA200602071 A ZA 200602071A ZA 200602071 A ZA200602071 A ZA 200602071A ZA 200602071 B ZA200602071 B ZA 200602071B
- Authority
- ZA
- South Africa
- Prior art keywords
- zinc
- present
- salt
- acid
- solution according
- Prior art date
Links
- HUCJFAOMUPXHDK-UHFFFAOYSA-N Xylometazoline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1 HUCJFAOMUPXHDK-UHFFFAOYSA-N 0.000 title claims description 26
- WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 title claims description 23
- 229960000833 xylometazoline Drugs 0.000 title claims description 13
- 229960001528 oxymetazoline Drugs 0.000 title claims description 12
- 239000003186 pharmaceutical solution Substances 0.000 title claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 239000000337 buffer salt Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 150000003751 zinc Chemical class 0.000 claims description 11
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 claims description 9
- 239000011670 zinc gluconate Substances 0.000 claims description 9
- 235000011478 zinc gluconate Nutrition 0.000 claims description 9
- 229960000306 zinc gluconate Drugs 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 229960000314 zinc acetate Drugs 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 229960001939 zinc chloride Drugs 0.000 claims description 2
- 239000011746 zinc citrate Substances 0.000 claims description 2
- 235000006076 zinc citrate Nutrition 0.000 claims description 2
- 229940068475 zinc citrate Drugs 0.000 claims description 2
- 239000011576 zinc lactate Substances 0.000 claims description 2
- 235000000193 zinc lactate Nutrition 0.000 claims description 2
- 229940050168 zinc lactate Drugs 0.000 claims description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- BRKFIPNBXFDCDM-MDTVQASCSA-L zinc;(2s)-2-amino-3-(1h-imidazol-5-yl)propanoate Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CC1=CNC=N1.[O-]C(=O)[C@@H](N)CC1=CNC=N1 BRKFIPNBXFDCDM-MDTVQASCSA-L 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 1
- 229940009098 aspartate Drugs 0.000 claims 1
- 229940046253 zinc orotate Drugs 0.000 claims 1
- YNMDOZLVAPMCBD-UHFFFAOYSA-L zinc;2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound [Zn+2].[O-]C(=O)C1=CC(=O)NC(=O)N1.[O-]C(=O)C1=CC(=O)NC(=O)N1 YNMDOZLVAPMCBD-UHFFFAOYSA-L 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- -1 for example Chemical class 0.000 description 8
- 239000008215 water for injection Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000001509 sodium citrate Substances 0.000 description 7
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960005162 oxymetazoline hydrochloride Drugs 0.000 description 3
- BEEDODBODQVSIM-UHFFFAOYSA-N oxymetazoline hydrochloride Chemical compound Cl.CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 BEEDODBODQVSIM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YGWFCQYETHJKNX-UHFFFAOYSA-N 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCC[NH2+]1 YGWFCQYETHJKNX-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 239000007922 nasal spray Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229960001095 xylometazoline hydrochloride Drugs 0.000 description 2
- 241000237518 Arion Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 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 description 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 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229940062776 zinc aspartate Drugs 0.000 description 1
- POEVDIARYKIEGF-CEOVSRFSSA-L zinc;(2s)-2-aminobutanedioate;hydron Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CC(O)=O.[O-]C(=O)[C@@H](N)CC(O)=O POEVDIARYKIEGF-CEOVSRFSSA-L 0.000 description 1
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
- A61K31/33—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
-
- 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
- A61K31/33—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
-
- 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
- A61K9/0043—Nose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P27/14—Decongestants or antiallergics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Otolaryngology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10337186A DE10337186A1 (de) | 2003-08-13 | 2003-08-13 | Wässrige Wirkstoff-Lösung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200602071B true ZA200602071B (en) | 2007-05-30 |
Family
ID=34201503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200602071A ZA200602071B (en) | 2003-08-13 | 2006-03-10 | Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20060222718A1 (pl) |
| EP (1) | EP1663141B1 (pl) |
| JP (1) | JP4750703B2 (pl) |
| KR (1) | KR20060065677A (pl) |
| CN (1) | CN100531733C (pl) |
| AT (1) | ATE357212T1 (pl) |
| AU (1) | AU2004266443A1 (pl) |
| BR (1) | BRPI0413478A (pl) |
| CA (1) | CA2535533C (pl) |
| CY (1) | CY1107633T1 (pl) |
| DE (2) | DE10337186A1 (pl) |
| DK (1) | DK1663141T3 (pl) |
| ES (1) | ES2282871T3 (pl) |
| MX (1) | MXPA06001596A (pl) |
| PL (1) | PL1663141T3 (pl) |
| PT (1) | PT1663141E (pl) |
| RU (1) | RU2343918C2 (pl) |
| WO (1) | WO2005018601A1 (pl) |
| ZA (1) | ZA200602071B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005075735A (ja) * | 2003-08-28 | 2005-03-24 | Rohto Pharmaceut Co Ltd | オキシメタゾリン含有組成物 |
| DE102007052380A1 (de) † | 2007-10-31 | 2009-05-07 | Bitop Ag | Osmolythaltige Zubereitungen zur Anwendung bei trockenen Schleimhäuten |
| CN101576539B (zh) * | 2009-06-19 | 2012-05-23 | 广东省药品检验所 | 一种盐酸赛洛唑啉中杂质a的测定方法 |
| DE102012005452A1 (de) * | 2011-12-30 | 2013-07-04 | Maria Clementine Martin Klosterfrau Vertriebsgesellschaft Mbh | Zusammensetzung für die nasale Applikation mit verbesserter Stabilität |
| US10598672B2 (en) | 2014-02-18 | 2020-03-24 | Cyrano Therapeutics, Inc. | Methods and compositions for diagnosing and treating loss and/or distortion of taste or smell |
| EP3236933B1 (en) | 2014-12-24 | 2018-11-14 | JADRAN - GALENSKI LABORATORIJ d.d. | A nasal composition containing sea water as stability-improving excipient |
| MX2018013475A (es) * | 2016-05-17 | 2019-08-12 | Proponent Biotech Gmbh | Acido carboxilico para tratar/prevenir congestion nasal. |
| DE102017117987A1 (de) | 2017-07-31 | 2019-01-31 | Maria Clementine Martin Klosterfrau Vertriebsgesellschaft Mbh | Neue Zusammensetzung für die nasale Applikation |
| CN107362141B (zh) * | 2017-08-16 | 2018-06-05 | 深圳大佛药业股份有限公司 | 一种盐酸羟甲唑啉鼻喷雾剂及其制备方法 |
| WO2020009812A1 (en) * | 2018-07-02 | 2020-01-09 | Bayer Healthcare Llc | Stable pharmaceutical formulations of oxymetazoline |
| US10799481B1 (en) * | 2019-05-06 | 2020-10-13 | Rvl Pharmaceuticals, Inc. | Compositions and methods for treating ocular disorders |
| WO2023046590A1 (en) | 2021-09-22 | 2023-03-30 | Jadran - Galenski Laboratorij D.D. | An improved pharmaceutical composition for nasal use, preparation, and use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478565A (en) * | 1990-03-27 | 1995-12-26 | Warner-Lambert Company | Treatment of sinus headache |
| DE19549421C2 (de) * | 1995-11-10 | 1999-11-18 | Klosterfrau Mcm Vetrieb Gmbh | Pharmazeutische Zubereitung zur Behandlung akuter Rhinitiden |
| AU741364B2 (en) * | 1998-01-30 | 2001-11-29 | Novartis Consumer Health S.A. | Nasal solutions |
| JPH11302184A (ja) * | 1998-04-21 | 1999-11-02 | Taisho Pharmaceut Co Ltd | 点鼻用組成物 |
| CA2376121C (en) * | 1999-06-22 | 2008-06-10 | Boehringer Ingelheim International Gmbh | Stable xylometazoline and oxymetazoline solution |
| EP1328214A4 (en) * | 2000-09-20 | 2009-07-29 | Shahinian Lee Jr | NASAL, INHALABLE AND LOCAL OPHTHALMIC PREPARATIONS AND MEDICATIONS WITH SPONTANEOUS CONSERVATION |
-
2003
- 2003-08-13 DE DE10337186A patent/DE10337186A1/de not_active Withdrawn
-
2004
- 2004-07-14 DE DE502004003305T patent/DE502004003305D1/de active Active
- 2004-07-14 MX MXPA06001596A patent/MXPA06001596A/es active IP Right Grant
- 2004-07-14 JP JP2006522915A patent/JP4750703B2/ja not_active Expired - Fee Related
- 2004-07-14 EP EP04740995A patent/EP1663141B1/de active Active
- 2004-07-14 BR BRPI0413478-8A patent/BRPI0413478A/pt not_active IP Right Cessation
- 2004-07-14 CN CNB2004800227931A patent/CN100531733C/zh not_active Expired - Fee Related
- 2004-07-14 ES ES04740995T patent/ES2282871T3/es active Active
- 2004-07-14 RU RU2006107446/15A patent/RU2343918C2/ru not_active IP Right Cessation
- 2004-07-14 AU AU2004266443A patent/AU2004266443A1/en not_active Abandoned
- 2004-07-14 US US10/567,845 patent/US20060222718A1/en not_active Abandoned
- 2004-07-14 WO PCT/EP2004/007780 patent/WO2005018601A1/de active IP Right Grant
- 2004-07-14 PT PT04740995T patent/PT1663141E/pt unknown
- 2004-07-14 AT AT04740995T patent/ATE357212T1/de active
- 2004-07-14 PL PL04740995T patent/PL1663141T3/pl unknown
- 2004-07-14 KR KR1020067002872A patent/KR20060065677A/ko not_active Application Discontinuation
- 2004-07-14 DK DK04740995T patent/DK1663141T3/da active
- 2004-07-14 CA CA2535533A patent/CA2535533C/en not_active Expired - Fee Related
-
2006
- 2006-03-10 ZA ZA200602071A patent/ZA200602071B/en unknown
-
2007
- 2007-05-21 CY CY20071100685T patent/CY1107633T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2282871T3 (es) | 2007-10-16 |
| CN100531733C (zh) | 2009-08-26 |
| CA2535533C (en) | 2011-10-18 |
| JP4750703B2 (ja) | 2011-08-17 |
| CA2535533A1 (en) | 2005-03-03 |
| MXPA06001596A (es) | 2006-05-19 |
| RU2343918C2 (ru) | 2009-01-20 |
| EP1663141B1 (de) | 2007-03-21 |
| ATE357212T1 (de) | 2007-04-15 |
| AU2004266443A1 (en) | 2005-03-03 |
| DE10337186A1 (de) | 2005-03-17 |
| CN1832726A (zh) | 2006-09-13 |
| EP1663141A1 (de) | 2006-06-07 |
| BRPI0413478A (pt) | 2006-10-17 |
| DE502004003305D1 (de) | 2007-05-03 |
| PT1663141E (pt) | 2007-06-27 |
| CY1107633T1 (el) | 2013-03-13 |
| US20060222718A1 (en) | 2006-10-05 |
| WO2005018601A1 (de) | 2005-03-03 |
| JP2007501817A (ja) | 2007-02-01 |
| RU2006107446A (ru) | 2007-09-20 |
| KR20060065677A (ko) | 2006-06-14 |
| PL1663141T3 (pl) | 2007-07-31 |
| DK1663141T3 (da) | 2007-07-30 |
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