JP2944759B2 - Antimicrobial composition - Google Patents
Antimicrobial compositionInfo
- Publication number
- JP2944759B2 JP2944759B2 JP52719495A JP52719495A JP2944759B2 JP 2944759 B2 JP2944759 B2 JP 2944759B2 JP 52719495 A JP52719495 A JP 52719495A JP 52719495 A JP52719495 A JP 52719495A JP 2944759 B2 JP2944759 B2 JP 2944759B2
- Authority
- JP
- Japan
- Prior art keywords
- ciprofloxacin
- composition
- sulfonic acid
- polystyrene sulfonic
- concentration
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 33
- 230000000845 anti-microbial effect Effects 0.000 title description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 50
- 229960003405 ciprofloxacin Drugs 0.000 claims description 24
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000009472 formulation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008213 purified water Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 3
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 239000011885 synergistic combination Substances 0.000 description 2
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- 208000006368 Bacterial Eye Infections Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 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
- 239000000872 buffer Substances 0.000 description 1
- 229940088515 ciloxan Drugs 0.000 description 1
- 229960001229 ciprofloxacin hydrochloride Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 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
- A61K31/74—Synthetic polymeric materials
- A61K31/795—Polymers containing sulfur
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】 発明の分野 本発明は、キノロン、特にシプロフロキサシン（cipr
ofloxacin）、およびポリスチレンスルホン酸ポリマー
（polystyrene sulfonic acid polymer）の共力作用性
の組み合わせを有する薬剤組成物に関する。Description: FIELD OF THE INVENTION The present invention relates to quinolones, especially ciprofloxacin (cipr).
ofloxacin) and a synergistic combination of polystyrene sulfonic acid polymer.
発明の背景 シプロフロキサシン（シロキサン（Ciloxan）TM、Alc
on Laboratories,Inc.,Fort Worth,Texas,U.S.A.）は、
眼の細菌感染症の治療に用いられている。しかし、生理
学的pHまたは高いpHではシプロフロキサシンの溶解性が
低いので、シプロフロキサシン処方物は、酸性のpHで開
発された。これらの処方物は、局所的に眼に投与される
場合、何人かの人にとっては不快であり得る。BACKGROUND OF THE INVENTION Ciprofloxacin (Ciloxan ™ , Alc
on Laboratories, Inc., Fort Worth, Texas, USA)
It is used to treat bacterial eye infections. However, ciprofloxacin formulations were developed at acidic pH due to the low solubility of ciprofloxacin at physiological or high pH. These formulations can be uncomfortable for some people when administered topically to the eye.
発明の要旨 本発明は、シプロフロキサシンおよびポリスチレンス
ルホン酸ポリマーを含有する、改善された局所的な眼用
または耳用組成物に関する。この組成物は、シプロフロ
キサシンと結合するイオン性ポリマー（すなわち、ポリ
スチレンスルホン酸ポリマー）を使用することにより、
高いpHでのシプロフロキサシンの溶解性が向上するよう
に処方される。ポリマーとシプロフロキサシンとの結合
により、眼の組織を刺激する遊離の薬物が少ないので、
眼に入れる際の初期の快適さおよび継続的な快適さが付
加的に提供される。本発明の組成物の他の付加的な利点
は、シプロフロキサシンが徐放されることである。SUMMARY OF THE INVENTION The present invention is directed to an improved topical ophthalmic or otic composition comprising ciprofloxacin and a polystyrene sulfonic acid polymer. The composition is made using an ionic polymer that binds to ciprofloxacin (ie, a polystyrene sulfonic acid polymer).
It is formulated to enhance the solubility of ciprofloxacin at high pH. Due to the combination of the polymer and ciprofloxacin, there is less free drug that irritates the eye tissue,
Initial and continuous comfort on entry into the eye is additionally provided. Another additional advantage of the compositions of the present invention is the sustained release of ciprofloxacin.
発明の詳細な説明 本発明の薬剤組成物は、抗菌活性を有するシプロフロ
キサシンと、ポリスチレンスルホン酸ポリマーとの共力
作用性の組み合わせを、好ましくは生理学的pHまたはほ
ぼ生理学的なpHで有する。これらの組成物は、特に眼に
おいて有用である。なぜなら、これらの組成物は、眼へ
の局所的な投与の際に快適であり、シプロフロキサシン
を徐放するからである。DETAILED DESCRIPTION OF THE INVENTION The pharmaceutical composition of the present invention has a synergistic combination of ciprofloxacin with antimicrobial activity and a polystyrene sulfonic acid polymer, preferably at or near physiological pH . These compositions are particularly useful for the eye. This is because these compositions are comfortable upon topical administration to the eye and provide a sustained release of ciprofloxacin.
本発明の処方物に用いられるポリスチレンスルホン酸
ポリマー（およびこれらの塩）は、下式を有する： ここで、 ＲはＨまたはCH3であり；そして Ｘはポリスチレンスルホン酸ポリマーの分子量が約1
0,000から160万まで変化し得るような整数、である。The polystyrene sulfonic acid polymers (and their salts) used in the formulations of the present invention have the formula: Where R is H or CH 3 ; and X is a polystyrene sulfonic acid polymer having a molecular weight of about 1
An integer, which can vary from 0,000 to 1.6 million.
上記式を有する好ましいポリスチレンスルホン酸で
は、ＲはＨであり、分子量は約500,000と1,000,000との
間であり、好ましくは約600,000である。このポリスチ
レンスルホン酸ポリマーは、本発明の処方物中では、約
8.0重量％（wt％）未満、好ましくは約5.0wt％未満の濃
度で存在するように用いられる。In preferred polystyrene sulfonic acids having the above formula, R is H and the molecular weight is between about 500,000 and 1,000,000, preferably about 600,000. The polystyrene sulfonic acid polymer is present in the formulation of the present invention at about
It is used to be present at a concentration of less than 8.0 wt% (wt%), preferably less than about 5.0 wt%.
シプロフロキサシン、その調製、および抗菌剤として
の使用は、米国特許第4,670,444号（Groheら）に開示さ
れている。その特許全体を本明細書中で参考として援用
する。Ciprofloxacin, its preparation and use as an antimicrobial agent is disclosed in US Patent No. 4,670,444 (Grohe et al.). The entire patent is incorporated herein by reference.
シプロフロキサシンは、以下の構造を有する： シプロフロキサシンの化学名は、１−シクロプロピル
−６−フルオロ−1,4−ジヒドロ−４−オキソ−７−
（１−ピペラジニル）−３−キノリンカルボン酸であ
る。Ciprofloxacin has the following structure: The chemical name of ciprofloxacin is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-
(1-piperazinyl) -3-quinolinecarboxylic acid.
処方物中のシプロフロキサシンの濃度は、全組成物の
約1.0wt％またはそれ未満、好ましくは約0.1wt％と0.75
wt％との間である。最も好ましい濃度は、約0.2wt％と
0.4wt％との間である。The concentration of ciprofloxacin in the formulation should be about 1.0 wt% or less of the total composition, preferably about 0.1 wt% and 0.75 wt%.
wt%. The most preferred concentration is about 0.2 wt%
0.4 wt%.
本発明の組成物は、シプロフロキサシンとポリスチレ
ンスルホン酸ポリマーとを水性媒体中で結合させ、必要
であればpHを調整することにより調製される。本発明の
組成物はまた、保存剤（例えば、塩化ベンザルコニウム
またはチメロサール）、粘度付与剤（例えば、ポリビニ
ルアルコールまたはヒドロキシプロピルメチルセルロー
ス）、および浸透圧調整剤（例えば、塩化ナトリウムま
たはマンニトール）のような、眼用または耳用処方物中
に従来見られる１つまたはそれを超える成分を含有し得
る。この組成物はまた、通常、pHを生理学的pHの範囲
（6.0と7.5との間）に維持するための、リン酸塩および
クエン酸塩のような緩衝剤を含有する。塩酸または水酸
化ナトリウムは、得られる組成物のpHを調整するために
代表的に用いられる。The compositions of the present invention are prepared by combining ciprofloxacin and a polystyrene sulfonic acid polymer in an aqueous medium and adjusting the pH if necessary. The compositions of the present invention may also include a preservative (eg, benzalkonium chloride or thimerosal), a viscosity enhancer (eg, polyvinyl alcohol or hydroxypropylmethylcellulose), and an osmotic agent (eg, sodium chloride or mannitol). It may contain one or more components conventionally found in ophthalmic or otic formulations. The composition also typically contains buffers such as phosphate and citrate to maintain the pH in the physiological pH range (between 6.0 and 7.5). Hydrochloric acid or sodium hydroxide is typically used to adjust the pH of the resulting composition.
この組成物は、眼および耳の細菌感染症を治療する際
に有用であり、そして熟練した臨床医の裁量により毎日
１回〜４回投与される。This composition is useful in treating bacterial infections of the eye and ear, and is administered one to four times daily at the discretion of the skilled clinician.
本発明の好ましい処方物を例示するために、以下の実
施例を示す。The following examples are provided to illustrate preferred formulations of the present invention.
混合の手順 1.撹拌器を備えた混合装置の中に、バッチ容積の約50％
の、20℃〜30℃の精製水を加える。 Mixing procedure 1. In a mixing device equipped with a stirrer, about 50% of the batch volume
Of purified water at 20 ° C to 30 ° C.
2.穏やかに撹拌し続けながら、PSSAを溶解させる。2. Dissolve PSSA with gentle stirring.
3.撹拌器を備えた混合装置の中に、バッチ容積の約30％
の、20℃〜30℃の精製水を加える。3. In a mixing device with a stirrer, about 30% of the batch volume
Of purified water at 20 ° C to 30 ° C.
4.穏やかに撹拌し続けながら、以下を溶解させる： マンニトール ホウ酸 塩酸シプロフロキサシン、一水和物 5.工程４で得たシプロフロキサシン溶液を、PSSA溶液に
かきまぜながらゆっくりと加える（注：沈澱物が短時間
形成され得るが、数分で溶解するはずである）。4. With gentle stirring, dissolve the following: mannitol boric acid ciprofloxacin hydrochloride, monohydrate 5. Add the ciprofloxacin solution obtained in step 4 slowly to the PSSA solution while stirring ( Note: a precipitate may form for a short time, but should dissolve in a few minutes).
6.バッチ容積の10％の冷精製水を用いて、シプロフロキ
サシン混合装置および輸送管をすすぎ、そしてPSSA/シ
プロフロキサシン溶液に加える。6. Using 10% of the batch volume of cold purified water, rinse the ciprofloxacin mixing device and transport tubing and add to the PSSA / ciprofloxacin solution.
7.pHを確認し、そして記録する。6N NaOH溶液または1N
HCl溶液を用いて、6.50の暫定目標にpHを調整する（100
Lのバッチ容積につき、約800mLの6N NaOHが必要であ
る）。（注:NaOHは、ゆっくりと添加されなければなら
ない。） 8.室温の精製水を適量加えて、100％の全バッチ容積と
する。均一になるまで混合する。7. Check and record the pH. 6N NaOH solution or 1N
Adjust the pH to an interim target of 6.50 using HCl solution (100
About 800 mL of 6N NaOH is required for each batch volume of L). (Note: NaOH must be added slowly.) 8. Add an appropriate amount of room temperature purified water to 100% total batch volume. Mix until uniform.
9.pHを確認し、そして記録する。必要であれば、6N NaO
H溶液または1N HCl溶液を用いて、6.70±0.1にpHを調整
する。9. Check and record the pH. 6N NaO if needed
Adjust pH to 6.70 ± 0.1 using H solution or 1N HCl solution.
10.6μｍまたはそれ未満のポリッシングフィルターを通
して、受容用反応器の中に溶液を濾過する。Filter the solution through a 10.6 μm or smaller polishing filter into a receiving reactor.
11.反応器中で最低30分間、最低121℃で生成物を滅菌す
る。11. Sterilize the product in the reactor for a minimum of 30 minutes at a minimum of 121 ° C.
12.反応器ジャケットに冷水を導入することにより、撹
拌しながら、ほぼ室温まで生成物を冷却する。12. Cool the product to approximately room temperature with agitation by introducing cold water into the reactor jacket.
13.バッチ重量が、工程10で測定された重量の99％未満
である場合には、親水性滅菌フィルターを通した精製水
で、工程10の重量まで調整する。均一になるまで混合す
る（最低15分間）。13. If the batch weight is less than 99% of the weight measured in step 10, make up to the weight of step 10 with purified water through a hydrophilic sterile filter. Mix until uniform (minimum 15 minutes).
特定の好ましい実施態様を参照することにより本発明
を記載してきたが、本発明は、その精神または本質的な
特性から逸脱することなく、その他の特定の形態または
変形に具体化されることが理解されるべきである。従っ
て、上記の実施態様は、あらゆる点で例示的なものであ
り、限定的なものでなく、本発明の範囲は、上記の説明
ではなく、添付の請求の範囲により示されると考えられ
る。Although the invention has been described by reference to certain preferred embodiments, it is understood that the invention can be embodied in other specific forms or modifications without departing from the spirit or essential characteristics thereof. It should be. Therefore, the above embodiments are intended in all respects to be illustrative and not restrictive, and the scope of the invention is intended to be indicated by the appended claims rather than the foregoing description.
フロントページの続き (56)参考文献 特開 昭58−74667（ＪＰ，Ａ) 特開 平７−10776（ＪＰ，Ａ) (58)調査した分野(Int.Cl.6，ＤＢ名) A61K 31/495 A61K 47/32 A61K 9/08 ＣＡ（ＳＴＮ)Continuation of the front page (56) References JP-A-58-74667 (JP, A) JP-A-7-10776 (JP, A) (58) Fields investigated (Int. Cl. 6 , DB name) A61K 31 / 495 A61K 47/32 A61K 9/08 CA (STN)
Claims (10)
ポリスチレンスルホン酸ポリマーを含有する、細菌感染
症の治療に有用な水性組成物。An aqueous composition useful for treating bacterial infections, comprising a pharmaceutically effective amount of ciprofloxacin and a polystyrene sulfonic acid polymer.
はそれ未満の濃度で存在する、請求項１に記載の組成
物。2. The composition of claim 1, wherein said ciprofloxacin is present at a concentration of 1.0 wt% or less.
5wt％との間の濃度で存在する、請求項２に記載の組成
物。3. The method of claim 1, wherein said ciprofloxacin is 0.1 wt% and 0.7 wt%.
3. The composition of claim 2, wherein the composition is present at a concentration between 5 wt%.
0.4wt％の間の濃度で存在する、請求項３に記載の組成
物。4. The method according to claim 1, wherein said ciprofloxacin is contained in an amount of from 0.2 wt%.
4. The composition of claim 3, wherein the composition is present at a concentration between 0.4 wt%.
度で存在する、請求項４に記載の組成物。5. The composition of claim 4, wherein said ciprofloxacin is present at a concentration of 0.3% by weight.
下式を有する、請求項１に記載の組成物： ここで、Ｒは、ＨまたはCH3；そしてＸは、ポリスチレ
ンスルホン酸ポリマーの分子量が10,000から160万まで
変化し得るような整数である。6. The polystyrene sulfonic acid polymer according to claim 1,
The composition of claim 1 having the formula: Where R is H or CH 3 ; and X is an integer such that the molecular weight of the polystyrene sulfonic acid polymer can vary from 10,000 to 1.6 million.
度が、8.0wt％またはそれ未満である、請求項６に記載
の組成物。7. The composition according to claim 6, wherein the concentration of the polystyrene sulfonic acid polymer is 8.0% by weight or less.
度が、5.0wt％またはそれ未満である、請求項６に記載
の組成物。8. The composition according to claim 6, wherein the concentration of the polystyrene sulfonic acid polymer is 5.0% by weight or less.
0と1,000,000との間である、請求項６に記載の組成物。9. R is H and said molecular weight is 500,00
7. The composition according to claim 6, which is between 0 and 1,000,000.
９に記載の組成物。10. The composition according to claim 9, wherein said molecular weight is 600,000.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1995/006587 WO1996037191A1 (en) | 1995-05-24 | 1995-05-24 | Antibacterial compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09507679A JPH09507679A (en) | 1997-08-05 |
| JP2944759B2 true JP2944759B2 (en) | 1999-09-06 |
Family
ID=22249170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52719495A Expired - Fee Related JP2944759B2 (en) | 1995-05-24 | 1995-05-24 | Antimicrobial composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2944759B2 (en) |
| AU (1) | AU705718B2 (en) |
| WO (1) | WO1996037191A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000066126A2 (en) * | 1999-04-29 | 2000-11-09 | Alza Corporation | Liposome compositions for improved drug retention |
| JP2011516503A (en) * | 2008-04-07 | 2011-05-26 | インターフェース バイオロジクス，インコーポレーテッド | Combination therapies to treat bacterial infections |
| JP5624281B2 (en) * | 2009-04-21 | 2014-11-12 | 東亜薬品株式会社 | Liquid formulation containing quinolone antibacterial agent with excellent photostability |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3142854A1 (en) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-CYCLOPROPYL-6-FLUOR-1,4-DIHYDRO-4-OXO-7-PIPERAZINO-CHINOLINE-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR CONTAINING ANTIBACTERIAL AGENTS |
| US4670444B1 (en) * | 1980-09-03 | 1999-02-09 | Bayer Ag | and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds |
| US5104649A (en) * | 1988-05-11 | 1992-04-14 | Monsanto Company | Surface-functionalized biocidal polymers |
| CA2064160C (en) * | 1991-03-27 | 1998-08-11 | Paul J. T. Missel | Use of combinations of gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
-
1995
- 1995-05-24 AU AU27621/95A patent/AU705718B2/en not_active Ceased
- 1995-05-24 JP JP52719495A patent/JP2944759B2/en not_active Expired - Fee Related
- 1995-05-24 WO PCT/US1995/006587 patent/WO1996037191A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996037191A1 (en) | 1996-11-28 |
| JPH09507679A (en) | 1997-08-05 |
| AU2762195A (en) | 1996-12-11 |
| AU705718B2 (en) | 1999-05-27 |
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