ZA200602071B - Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline - Google Patents

Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline Download PDF

Info

Publication number: ZA200602071B
Authority: ZA; South Africa
Prior art keywords: zinc; present; salt; acid; solution according
Prior art date: 2003-08-13

Application number

ZA200602071A

Other languages

English (en)

Inventor

Boehmke Frank

Forber Dagmar

Pfaff Barbara

Eschenbach Bernd

Hey Claudia

Tschaikin Marion

Original Assignee

Merck Patent Gmbh

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.)

2003-08-13

Filing date

2006-03-10

Publication date

2007-05-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34201503&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200602071(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-03-10 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2007-05-30 Publication of ZA200602071B publication Critical patent/ZA200602071B/en

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)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Otolaryngology (AREA)
Bioinformatics & Cheminformatics (AREA)
Ophthalmology & Optometry (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

ZA200602071A 2003-08-13 2006-03-10 Aqueous pharmaceutical solution containing oxymetazoline and/or xylometazoline ZA200602071B (en)

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 (fr)
EP (1)	EP1663141B1 (fr)
JP (1)	JP4750703B2 (fr)
KR (1)	KR20060065677A (fr)
CN (1)	CN100531733C (fr)
AT (1)	ATE357212T1 (fr)
AU (1)	AU2004266443A1 (fr)
BR (1)	BRPI0413478A (fr)
CA (1)	CA2535533C (fr)
CY (1)	CY1107633T1 (fr)
DE (2)	DE10337186A1 (fr)
DK (1)	DK1663141T3 (fr)
ES (1)	ES2282871T3 (fr)
MX (1)	MXPA06001596A (fr)
PL (1)	PL1663141T3 (fr)
PT (1)	PT1663141E (fr)
RU (1)	RU2343918C2 (fr)
WO (1)	WO2005018601A1 (fr)
ZA (1)	ZA200602071B (fr)

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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
US8580801B2 (en)	2008-07-23	2013-11-12	Robert I. Henkin	Phosphodiesterase inhibitor treatment
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
US20120225918A1 (en) *	2011-03-03	2012-09-06	Voom, Llc	Compositions and Methods for Non-Surgical Treatment of Ptosis
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 (fr)	2014-12-24	2018-11-14	JADRAN - GALENSKI LABORATORIJ d.d.	Composition nasale contenant de l'eau de mer en tant qu'excipient d'amélioration de stabilité
RU2018143564A (ru) *	2016-05-17	2020-06-17	Пропонент Байотек Гмбх	Карбоновая кислота, предназначенная для лечения/предупреждения заложенности носа
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
US20210244710A1 (en) *	2018-07-02	2021-08-12	Kangping Xiao	Stable pharmaceutical formulations of oxymetazoline
US10799481B1 (en) *	2019-05-06	2020-10-13	Rvl Pharmaceuticals, Inc.	Compositions and methods for treating ocular disorders
WO2021194893A1 (fr)	2020-03-24	2021-09-30	Cyrano Therapeutics, Inc.	Traitement d'un dysfonctionnement chimiosensoriel résultant d'une infection à coronavirus
ES3039833T3 (en)	2021-09-22	2025-10-24	Jadran Galenski Laboratorij D D	An improved pharmaceutical composition for nasal use, preparation, and use thereof
CN117982422B (zh) *	2024-04-03	2024-07-26	深圳大佛药业股份有限公司	一种用于治疗鼻炎的喷雾剂

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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
DE69901936T2 (de) *	1998-01-30	2002-11-28	Novartis Consumer Health S.A., Nyon	Nasale lösungen
JPH11302184A (ja) *	1998-04-21	1999-11-02	Taisho Pharmaceut Co Ltd	点鼻用組成物
NL1011016C2 (nl) *	1999-01-13	2000-07-14	Dagra Pharma Bv	Neusspray op basis van xylometazoline en kamille-extract.
WO2000078297A2 (fr) *	1999-06-22	2000-12-28	Boehringer Ingelheim International Gmbh	Solution de xylometazoline et d'oxymetazoline stable
CA2423354C (fr) *	2000-09-20	2009-12-15	Lee Shahinian Jr.	Preparations et medications nasales, inhalables et ophtalmiques locales a conservation spontanee
RU2212235C1 (ru) *	2001-12-24	2003-09-20	Закрытое акционерное общество "Брынцалов-А"	Капли назальные бризолин, обладающие сосудосуживающим, противовоспалительным и противоотечным действием

2003
- 2003-08-13 DE DE10337186A patent/DE10337186A1/de not_active Withdrawn
2004
- 2004-07-14 PL PL04740995T patent/PL1663141T3/pl unknown
- 2004-07-14 PT PT04740995T patent/PT1663141E/pt unknown
- 2004-07-14 CN CNB2004800227931A patent/CN100531733C/zh not_active Expired - Fee Related
- 2004-07-14 CA CA2535533A patent/CA2535533C/fr not_active Expired - Fee Related
- 2004-07-14 KR KR1020067002872A patent/KR20060065677A/ko not_active Ceased
- 2004-07-14 US US10/567,845 patent/US20060222718A1/en not_active Abandoned
- 2004-07-14 DE DE502004003305T patent/DE502004003305D1/de not_active Expired - Lifetime
- 2004-07-14 BR BRPI0413478-8A patent/BRPI0413478A/pt not_active IP Right Cessation
- 2004-07-14 RU RU2006107446/15A patent/RU2343918C2/ru not_active IP Right Cessation
- 2004-07-14 MX MXPA06001596A patent/MXPA06001596A/es active IP Right Grant
- 2004-07-14 EP EP04740995A patent/EP1663141B1/fr not_active Expired - Lifetime
- 2004-07-14 ES ES04740995T patent/ES2282871T3/es not_active Expired - Lifetime
- 2004-07-14 AT AT04740995T patent/ATE357212T1/de active
- 2004-07-14 DK DK04740995T patent/DK1663141T3/da active
- 2004-07-14 WO PCT/EP2004/007780 patent/WO2005018601A1/fr not_active Ceased
- 2004-07-14 AU AU2004266443A patent/AU2004266443A1/en not_active Abandoned
- 2004-07-14 JP JP2006522915A patent/JP4750703B2/ja 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
ATE357212T1 (de)	2007-04-15
RU2006107446A (ru)	2007-09-20
WO2005018601A1 (fr)	2005-03-03
DE502004003305D1 (de)	2007-05-03
EP1663141B1 (fr)	2007-03-21
CY1107633T1 (el)	2013-03-13
DK1663141T3 (da)	2007-07-30
US20060222718A1 (en)	2006-10-05
RU2343918C2 (ru)	2009-01-20
ES2282871T3 (es)	2007-10-16
CA2535533C (fr)	2011-10-18
BRPI0413478A (pt)	2006-10-17
CN100531733C (zh)	2009-08-26
AU2004266443A1 (en)	2005-03-03
CN1832726A (zh)	2006-09-13
JP4750703B2 (ja)	2011-08-17
PL1663141T3 (pl)	2007-07-31
JP2007501817A (ja)	2007-02-01
KR20060065677A (ko)	2006-06-14
PT1663141E (pt)	2007-06-27
MXPA06001596A (es)	2006-05-19
CA2535533A1 (fr)	2005-03-03
EP1663141A1 (fr)	2006-06-07
DE10337186A1 (de)	2005-03-17

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