WO2000010570A1 - Preparations liquides aqueuses - Google Patents
Preparations liquides aqueuses Download PDFInfo
- Publication number
- WO2000010570A1 WO2000010570A1 PCT/JP1999/004483 JP9904483W WO0010570A1 WO 2000010570 A1 WO2000010570 A1 WO 2000010570A1 JP 9904483 W JP9904483 W JP 9904483W WO 0010570 A1 WO0010570 A1 WO 0010570A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- gatifloxacin
- sodium edetate
- sodium
- salt
- aqueous solution
- Prior art date
Links
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
- A61K31/495—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
- A61K31/495—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
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the present invention relates to a quinolone carboxylic acid derivative, gatifloxacin (chemical name: (sat) -11-cyclopropyl-16-fluoro-1,4-dihydro-8-methoxy-17- (3-methyl-1-11) -Piperazinyl) -14-oxo-13-quinoline carboxylic acid).
- the present invention also relates to a method for enhancing the corneal permeability of gatifloxacin, a method for preventing gatifloxacin from crystal precipitation, and a method for preventing gatifloxacin from coloring.
- Gatifloxacin is a new quinolone synthetic antibacterial agent that has been shown to exhibit strong antibacterial activity not only against gram-negative bacteria but also against gram-positive bacteria, anaerobic bacteria, and mycoplasmas. It has been proposed to be applied to ophthalmological infections such as lacrimal cystitis and stye, and otological infections such as otitis externa, otitis media and sinusitis (see Japanese Patent Publication No. Hei 8-95597).
- gatifloxacin has been proposed for use in ophthalmological or otolaryngological infections, it is important to note, for example, that aqueous solutions for topical administration to be applied, such as transfer into the eye and stability. No studies have been reported.
- the present invention relates to gatifloxacin in the field of ophthalmology or otorhinolaryngology.
- An object of the present invention is to provide an aqueous formulation containing gatifloxacin as an active ingredient, in particular, to enable actual application to pharmaceuticals.
- the present inventors have conducted intensive studies on the application of gatifloxacin to the ophthalmic field, and have found that the object can be achieved by coexisting with edetate sodium.
- Sodium edetate is thought to reduce the calcium concentration in corneal epithelial cells and increase the intercellular space, thereby promoting the ability of water-soluble biopharmaceuticals to enter the eye.
- the enhancement of drug permeability to the cornea depends on sodium edetate concentration.
- solubility of gatifloxacin depends on pH, and the solubility near physiological pH is very low. For this reason, in order to dissolve a sufficient amount of the drug, the pH of the aqueous solution must be adjusted to the acidic side or the alkaline side. In these pH regions, irritation at the time of topical administration is a problem. Becomes However, it was found that coexistence with sodium edetate improved the solubility of gachifu-oxaxin near physiological pH.
- the present invention has been completed based on these new findings of the present inventors, and provides an aqueous solution containing gatifloxacin or a salt thereof and sodium edetate.
- the aqueous liquid preparation of the present invention is an aqueous solution containing gatifloxacin or a salt thereof and sodium edetate.
- the present invention provides a method for enhancing corneal permeability of gatifloxacin by adding sodium edetate to an eye drop containing gatifloxacin or a salt thereof.
- Sodium edetate in solution To prevent the precipitation of gatifloxacin crystals and a method of preventing coloring of gatifloxacin by mixing sodium edetate with an aqueous solution containing gatifloxacin or a salt thereof. I do.
- the present invention uses gatifloxacin or a salt thereof as an active ingredient.
- the salt of gachifu-oxaxin include salts with inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, salts with organic acids such as methanesulfonic acid, lactic acid, oxalic acid, and acetic acid, or sodium, potassium, magnesium, and the like. Salts such as calcium, anoremium, cerium, chromium, konole, copper, iron, zinc, platinum and silver can be used.
- gatifloxacin a salt thereof (hereinafter sometimes simply referred to as “gatifloxacin”) used in the aqueous liquid preparation of the present invention varies depending on the degree of infection to be treated. ! -1. Ow / v 0 / o, preferably 0.1-0.8 w / v%, more preferably 0.3-0.5 wZv%.
- the mixing amount of sodium edetate used in the present invention is usually 0.001 to 0.2 Z, preferably 0.005 to 0.1 Lw / v%, and more preferably 0.01 to 0.1 Lw / v%. It is.
- the pH of the aqueous liquid preparation of the present invention is usually adjusted to 5 to 8, preferably 5.5 to 7.5, and more preferably 6 to 7.
- the aqueous liquid preparation of the present invention may further contain, if necessary, a tonicity agent (eg, sodium chloride, potassium chloride, boric acid, glycerin, propylene glycol, mannitol, sorbitol, glucose, etc.), a buffering agent ( For example, phosphate buffer, acetate buffer, borate buffer, citrate buffer, glutamic acid, ⁇ -aminocaproic acid, etc., preservatives (benzalkonium chloride, benzethonium chloride, chlorhexidine dalconate, chlorobutanol, Benzyl alcohol, sodium dehydroacetate, paraoxybenzoic acid esters, etc., viscous agents (methylcellulose, hydroxyethyl cellulose, hydroxypropylmethylcellulose, carboxymethylsenololose, sodium hyanolenolate, carboxyvinyl polymer, Po Ribul Arco I , Polyvinylpyrrolidone, macrogol, etc
- the aqueous liquid preparation of the present invention may be manufactured by a method known per se, and for example, can be manufactured by a method described in Eye drops or liquid preparations in the Japanese Pharmacopoeia 13th Edition, General Rules for Preparations.
- the ophthalmic solution of the present invention has an antibacterial effect, and one drop at a time for the prevention and treatment of blepharitis, stye, lacrimal inflammation, conjunctivitis, blepharitis, keratitis, corneal ulcer, postoperative infection, etc. It should be instilled about three times a day.
- otitis externa and otitis media usually 6 to 10 drops are administered twice a day.
- sinusitis usually 2 to 4 ml is sprayed and inhaled three times a week every other day, or 1 ml is injected into the maxillary sinus once a week. do it.
- the frequency can be increased or decreased as appropriate depending on the severity of the symptoms.
- Gatifloxacin eye drops (Formulations A to C) were prepared according to the formulations in Table 1. One 50 ⁇ l drop was instilled once into Japanese white male rabbits weighing about 2 kg. One hour after the instillation, the aqueous humor was collected, and the concentration of gatifloxacin in the aqueous humor was measured by HPLC.
- Table 2 shows the concentration of gachifu-oxacin in aqueous humor 1 hour after instillation.
- pH decreases Gatifloxacin aqueous humor transfer decreased.
- Formulations containing sodium edetate and adjusted to pH 6.0 (formulation C) had about 1.2 times the aqueous humor transfer compared to formulations A (pH 7.0) and B (pH 6.0) as controls. , Increased by 1.5 times. Since the sodium edetate concentration normally used to enhance corneal permeability is 0.5 w Zv%, this result indicates that the corneal permeability of Is enhanced.
- gatifloxacin aqueous solutions (formulations B to D) were prepared. Each formulation solution was filled into a 5 ml glass ampoule, frozen at 130 ° C. (overnight), and thawed at room temperature, and the operation of melting at room temperature was repeated.
- aqueous solutions for eye drops, ear drops, and nasal drops were prepared according to the following formulation.
- aqueous solutions for eye drops, ear drops, and nasal drops were prepared according to the following formulation.
- aqueous solutions for eye drops, ear drops, and nasal drops were prepared according to the following formulation.
- Example 4 Usual manner, by the following formulation, eye drops, c to prepare an aqueous solution for ear and nasal gatifloxacin 0. 3 g
- aqueous solutions for eye drops, ear drops, and nasal drops were prepared according to the following formulation.
- an aqueous solution for eye drops, ear drops, and nasal drops was prepared according to the following formulation: c Gatifloxacin 0.5 g
- aqueous solutions for eye drops, ear drops, and nasal drops were prepared according to the following formulation.
- an aqueous solution for eye drops, ear drops, and nasal drops was prepared according to the following formulation.
- the ophthalmic solution of the present invention can enhance the corneal permeability of the active ingredient gatifloxacin even at a commonly used sodium edetate concentration of 10 to 10%. Can be. Further, as shown in Experimental Example 2, the aqueous solution of the present invention can also prevent precipitation of gachifloxacin under low-temperature storage conditions, and as shown in Experimental Example 3, the metal solution of gatifloxacin It is an extremely useful aqueous liquid that can prevent coloring due to ions.
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69932313T DE69932313T2 (de) | 1998-08-21 | 1999-08-20 | Wässerige flüssige zubereitungen |
AU53026/99A AU761040B2 (en) | 1998-08-21 | 1999-08-20 | Aqueous liquid preparations |
KR1020007004221A KR100595956B1 (ko) | 1998-08-21 | 1999-08-20 | 수성액 제약학적 조성물 |
US09/529,882 US6333045B1 (en) | 1998-08-21 | 1999-08-20 | Aqueous liquid pharmaceutical composition comprised of gatifloxacin |
NZ504017A NZ504017A (en) | 1998-08-21 | 1999-08-20 | Preparation of gatifloxacin and disodium edetate |
BRPI9906735A BRPI9906735B8 (pt) | 1998-08-21 | 1999-08-20 | 'composição farmacêutica líquida aquosa e método para prevenção de precipitações de cristais e para prevenção da coloração de gatifloxacina.' |
CA002307632A CA2307632C (en) | 1998-08-21 | 1999-08-20 | Aqueous liquid pharmaceutical composition |
EP99938550A EP1025846B1 (en) | 1998-08-21 | 1999-08-20 | Aqueous liquid preparations |
JP2000565891A JP5138128B2 (ja) | 1998-08-21 | 1999-08-20 | 水性液剤 |
HK01100837A HK1029934A1 (en) | 1998-08-21 | 2001-02-06 | Aqueous liquid preparations |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10/235432 | 1998-08-21 | ||
JP23543298 | 1998-08-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000010570A1 true WO2000010570A1 (fr) | 2000-03-02 |
Family
ID=16986030
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1999/004483 WO2000010570A1 (fr) | 1998-08-21 | 1999-08-20 | Preparations liquides aqueuses |
Country Status (17)
Country | Link |
---|---|
US (1) | US6333045B1 (ja) |
EP (1) | EP1025846B1 (ja) |
JP (1) | JP5138128B2 (ja) |
KR (1) | KR100595956B1 (ja) |
CN (1) | CN1133432C (ja) |
AT (1) | ATE332692T1 (ja) |
AU (1) | AU761040B2 (ja) |
BR (1) | BRPI9906735B8 (ja) |
CA (1) | CA2307632C (ja) |
DE (1) | DE69932313T2 (ja) |
DK (1) | DK1025846T3 (ja) |
ES (1) | ES2264266T3 (ja) |
HK (1) | HK1029934A1 (ja) |
NZ (1) | NZ504017A (ja) |
PT (1) | PT1025846E (ja) |
TW (1) | TW537895B (ja) |
WO (1) | WO2000010570A1 (ja) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001057017A1 (fr) * | 2000-02-01 | 2001-08-09 | Kyorin Pharmaceutical Co., Ltd. | Sel de sulfate de quinolone d'acide carboxylique et son utilisation |
WO2001089496A3 (en) * | 2000-05-19 | 2002-04-25 | Alcon Lab Inc | Compositions and methods for treating otic, ophthalmic and nasal infections comprising quinolone antibiotics |
JP2004528369A (ja) * | 2001-05-03 | 2004-09-16 | アラーガン、インコーポレイテッド | 向上した薬物動態特性を有する組成物 |
JP2005008625A (ja) * | 2003-05-23 | 2005-01-13 | Santen Pharmaceut Co Ltd | キノロン系抗菌化合物を含有する点眼液 |
WO2008044733A1 (fr) | 2006-10-12 | 2008-04-17 | Kyorin Pharmaceutical Co., Ltd. | Préparation liquide aqueuse à pénétration de gatifloxacine intraoculaire améliorée |
WO2008044734A1 (fr) | 2006-10-12 | 2008-04-17 | Kyorin Pharmaceutical Co., Ltd. | Préparation liquide aqueuse comprenant de la gatifloxacine |
JP2008247828A (ja) * | 2007-03-30 | 2008-10-16 | Wakamoto Pharmaceut Co Ltd | ラタノプロストを含有する水性医薬組成物。 |
JP2009209069A (ja) * | 2008-03-03 | 2009-09-17 | Rohto Pharmaceut Co Ltd | 光安定性が改善されたニューキノロン系抗菌剤含有医薬組成物 |
WO2009123098A1 (ja) * | 2008-03-31 | 2009-10-08 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤、その製造方法、および、該水性液剤の低温保存および凍結融解時の沈殿生成を抑制する方法 |
JP2010132681A (ja) * | 2001-05-03 | 2010-06-17 | Allergan Inc | 向上した薬物動態特性を有する組成物 |
JP4578576B2 (ja) * | 2008-03-31 | 2010-11-10 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤 |
JP2016164183A (ja) * | 2009-02-18 | 2016-09-08 | アラダイム コーポレーション | 肺送達のためのpH調節された製剤 |
JP2021113236A (ja) * | 2016-03-25 | 2021-08-05 | 興和株式会社 | 眼科用組成物 その2 |
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US6716830B2 (en) | 1998-09-30 | 2004-04-06 | Alcon, Inc. | Ophthalmic antibiotic compositions containing moxifloxacin |
US6740664B2 (en) | 1998-09-30 | 2004-05-25 | Alcon, Inc. | Methods for treating otic and ophthalmic infections |
PE20010635A1 (es) | 1999-10-08 | 2001-08-15 | Smithkline Beecham Corp | Inhibidores de fab i utiles para el tratamiento de infecciones bacterianas |
ES2320984T3 (es) | 2001-04-06 | 2009-06-01 | Affinium Pharmaceuticals, Inc. | Inhibidores de fab i. |
ES2518316T3 (es) | 2002-12-06 | 2014-11-05 | Debiopharm International Sa | Compuestos heterocíclicos, métodos de fabricación de los mismos y su uso en terapia |
CA2519429C (en) | 2003-03-17 | 2013-08-06 | Affinium Pharmaceuticals, Inc. | Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics |
US20040202687A1 (en) * | 2003-04-14 | 2004-10-14 | Babu M.K. Manoj | Ciprofloxacin formulations and methods of making and using the same |
US20050085446A1 (en) * | 2003-04-14 | 2005-04-21 | Babu M.K. M. | Fluoroquinolone formulations and methods of making and using the same |
ES2515101T3 (es) | 2004-06-04 | 2014-10-29 | Debiopharm International Sa | Derivados de acrilamida como agentes antibióticos |
WO2006099325A2 (en) | 2005-03-10 | 2006-09-21 | 3M Innovative Properties Company | Methods of treating ear infections |
US8524734B2 (en) | 2005-05-18 | 2013-09-03 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
US7838532B2 (en) * | 2005-05-18 | 2010-11-23 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
EP2054422B1 (en) | 2006-07-20 | 2017-06-14 | Debiopharm International SA | Acrylamide derivatives as fab i inhibitors |
US8263613B2 (en) | 2007-02-16 | 2012-09-11 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab I inhibitors |
CA2621616A1 (en) * | 2007-02-19 | 2008-08-19 | Alcon Research, Ltd. | Topical gatifloxacin formulations |
CA2739893C (en) | 2008-10-07 | 2016-10-04 | Mpex Pharmaceuticals, Inc. | Inhalation of levofloxacin for reducing lung inflammation |
KR20110091510A (ko) | 2008-10-07 | 2011-08-11 | 엠펙스 파마슈티컬즈, 인코포레이티드 | 약동학 개선을 위한 에어로졸 플루오로퀴놀론 제형 |
UA92423C2 (ru) * | 2009-07-24 | 2010-10-25 | Анатолій Альбертович Кузьмін | Антибактериальная композиция |
RU2015130524A (ru) | 2009-09-04 | 2018-12-21 | Раптор Фармасьютикалз Инк. | Применение левофлоксацина в форме аэрозоля для лечения муковисцидоза |
UA113981C2 (xx) | 2012-03-26 | 2017-04-10 | Офтальмологічний розчин, що містить диквафасол | |
NZ702695A (en) | 2012-06-19 | 2015-10-30 | Debiopharm Int Sa | Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
US10751351B2 (en) | 2016-02-26 | 2020-08-25 | Debiopharm International S.A. | Medicament for treatment of diabetic foot infections |
KR102275012B1 (ko) | 2016-08-12 | 2021-07-07 | 실크 테크놀로지스 리미티드 | 염증 치료용 실크 유래 단백질 |
US11382910B2 (en) | 2020-08-26 | 2022-07-12 | Somerset Therapeutics, Llc. | Loteprednol and moxifloxacin compositions and methods |
US11510930B2 (en) | 2020-08-26 | 2022-11-29 | Somerset Therapeutics, Llc | Gatifloxacin, prednisolone, and bromfenac compositions and methods |
US11523987B2 (en) | 2020-08-26 | 2022-12-13 | Somerset Therapeutics, Llc | Trimcinolone and moxifloxacin methods |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62252772A (ja) * | 1986-01-21 | 1987-11-04 | Kyorin Pharmaceut Co Ltd | 選択毒性に優れた8−アルコキシキノロンカルボン酸およびその塩並びにその製造方法 |
JPS63174930A (ja) * | 1987-01-14 | 1988-07-19 | Hokuriku Seiyaku Co Ltd | キノロンカルボン酸の水性組成物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU553415B2 (en) * | 1983-09-19 | 1986-07-17 | Abbott Japan Co., Ltd. | 6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids |
JP2549285B2 (ja) * | 1987-02-02 | 1996-10-30 | 第一製薬株式会社 | 鼻用噴霧剤 |
JPH01258620A (ja) * | 1988-04-08 | 1989-10-16 | Dai Ichi Seiyaku Co Ltd | 耳疾患用局所製剤 |
JP3996659B2 (ja) * | 1995-10-25 | 2007-10-24 | 千寿製薬株式会社 | 血管新生抑制剤 |
JPH09124484A (ja) * | 1995-10-27 | 1997-05-13 | Schering Purau Kk | 点眼剤 |
AU5342498A (en) * | 1997-01-10 | 1998-08-03 | Wakamoto Pharmaceutical Co., Ltd. | Difluprednate-containing ophthalmic o/w emulsion composition |
-
1999
- 1999-08-20 ES ES99938550T patent/ES2264266T3/es not_active Expired - Lifetime
- 1999-08-20 DK DK99938550T patent/DK1025846T3/da active
- 1999-08-20 DE DE69932313T patent/DE69932313T2/de not_active Expired - Lifetime
- 1999-08-20 CA CA002307632A patent/CA2307632C/en not_active Expired - Lifetime
- 1999-08-20 AT AT99938550T patent/ATE332692T1/de active
- 1999-08-20 WO PCT/JP1999/004483 patent/WO2000010570A1/ja active IP Right Grant
- 1999-08-20 KR KR1020007004221A patent/KR100595956B1/ko not_active IP Right Cessation
- 1999-08-20 TW TW088114247A patent/TW537895B/zh not_active IP Right Cessation
- 1999-08-20 JP JP2000565891A patent/JP5138128B2/ja not_active Expired - Lifetime
- 1999-08-20 AU AU53026/99A patent/AU761040B2/en not_active Expired
- 1999-08-20 US US09/529,882 patent/US6333045B1/en not_active Expired - Lifetime
- 1999-08-20 CN CNB998014087A patent/CN1133432C/zh not_active Expired - Lifetime
- 1999-08-20 EP EP99938550A patent/EP1025846B1/en not_active Expired - Lifetime
- 1999-08-20 PT PT99938550T patent/PT1025846E/pt unknown
- 1999-08-20 BR BRPI9906735A patent/BRPI9906735B8/pt not_active IP Right Cessation
- 1999-08-20 NZ NZ504017A patent/NZ504017A/xx not_active IP Right Cessation
-
2001
- 2001-02-06 HK HK01100837A patent/HK1029934A1/xx not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62252772A (ja) * | 1986-01-21 | 1987-11-04 | Kyorin Pharmaceut Co Ltd | 選択毒性に優れた8−アルコキシキノロンカルボン酸およびその塩並びにその製造方法 |
JPS63174930A (ja) * | 1987-01-14 | 1988-07-19 | Hokuriku Seiyaku Co Ltd | キノロンカルボン酸の水性組成物 |
Non-Patent Citations (3)
Title |
---|
KUBO SHUTA ET AL.: "Enhanced Chemiluminescence Response of Polymorphonuclear Leukocytes by New Quinolone Antimicrobials", CHEMOTHERAPY, vol. 40, no. 5, 1994, pages 333 - 336, XP002925557 * |
SASAKI HITOSHI ET AL.: "Different Effects of Absorption Promoters on Corneal and Conjunctival Penetration of Ophthalmic beta-Blockers", PHARMACEUTICAL RESEARCH, vol. 12, no. 8, 1995, pages 1146 - 1150, XP002925558 * |
TANAKA MASATOSHI ET AL.: "Emergence of In Vitro Resistance to Fluoroquinolones in Neisseria gonorrhoeae Isolated in Japan", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 39, no. 10, 1995, pages 2367 - 2370, XP002925556 * |
Cited By (16)
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US6582609B2 (en) | 2000-02-01 | 2003-06-24 | Kyorin Pharmaceutical Co., Ltd. | Sulfate salt of quinolonecarboxylic acid derivatives and the use thereof |
WO2001057017A1 (fr) * | 2000-02-01 | 2001-08-09 | Kyorin Pharmaceutical Co., Ltd. | Sel de sulfate de quinolone d'acide carboxylique et son utilisation |
WO2001089496A3 (en) * | 2000-05-19 | 2002-04-25 | Alcon Lab Inc | Compositions and methods for treating otic, ophthalmic and nasal infections comprising quinolone antibiotics |
JP2010132681A (ja) * | 2001-05-03 | 2010-06-17 | Allergan Inc | 向上した薬物動態特性を有する組成物 |
JP2004528369A (ja) * | 2001-05-03 | 2004-09-16 | アラーガン、インコーポレイテッド | 向上した薬物動態特性を有する組成物 |
JP2005008625A (ja) * | 2003-05-23 | 2005-01-13 | Santen Pharmaceut Co Ltd | キノロン系抗菌化合物を含有する点眼液 |
WO2008044733A1 (fr) | 2006-10-12 | 2008-04-17 | Kyorin Pharmaceutical Co., Ltd. | Préparation liquide aqueuse à pénétration de gatifloxacine intraoculaire améliorée |
WO2008044734A1 (fr) | 2006-10-12 | 2008-04-17 | Kyorin Pharmaceutical Co., Ltd. | Préparation liquide aqueuse comprenant de la gatifloxacine |
JP2008247828A (ja) * | 2007-03-30 | 2008-10-16 | Wakamoto Pharmaceut Co Ltd | ラタノプロストを含有する水性医薬組成物。 |
JP2009209069A (ja) * | 2008-03-03 | 2009-09-17 | Rohto Pharmaceut Co Ltd | 光安定性が改善されたニューキノロン系抗菌剤含有医薬組成物 |
WO2009123098A1 (ja) * | 2008-03-31 | 2009-10-08 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤、その製造方法、および、該水性液剤の低温保存および凍結融解時の沈殿生成を抑制する方法 |
JP4578576B2 (ja) * | 2008-03-31 | 2010-11-10 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤 |
JPWO2009123099A1 (ja) * | 2008-03-31 | 2011-07-28 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤 |
JP5535900B2 (ja) * | 2008-03-31 | 2014-07-02 | 杏林製薬株式会社 | ガチフロキサシン含有水性液剤、その製造方法、および、該水性液剤の低温保存および凍結融解時の沈殿生成を抑制する方法 |
JP2016164183A (ja) * | 2009-02-18 | 2016-09-08 | アラダイム コーポレーション | 肺送達のためのpH調節された製剤 |
JP2021113236A (ja) * | 2016-03-25 | 2021-08-05 | 興和株式会社 | 眼科用組成物 その2 |
Also Published As
Publication number | Publication date |
---|---|
AU5302699A (en) | 2000-03-14 |
DE69932313T2 (de) | 2007-07-19 |
JP5138128B2 (ja) | 2013-02-06 |
AU761040B2 (en) | 2003-05-29 |
CA2307632C (en) | 2007-05-22 |
US6333045B1 (en) | 2001-12-25 |
NZ504017A (en) | 2001-09-28 |
CA2307632A1 (en) | 2000-03-02 |
BR9906735A (pt) | 2000-08-15 |
EP1025846A4 (en) | 2004-12-29 |
KR20010031240A (ko) | 2001-04-16 |
DE69932313D1 (de) | 2006-08-24 |
EP1025846A1 (en) | 2000-08-09 |
BRPI9906735B1 (pt) | 2015-09-01 |
TW537895B (en) | 2003-06-21 |
CN1275081A (zh) | 2000-11-29 |
CN1133432C (zh) | 2004-01-07 |
BRPI9906735B8 (pt) | 2021-05-25 |
PT1025846E (pt) | 2006-10-31 |
KR100595956B1 (ko) | 2006-07-03 |
DK1025846T3 (da) | 2006-11-06 |
ATE332692T1 (de) | 2006-08-15 |
HK1029934A1 (en) | 2001-04-20 |
ES2264266T3 (es) | 2006-12-16 |
EP1025846B1 (en) | 2006-07-12 |
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