JPH03287535A - Aqueous solution of pranoprofen - Google Patents
Aqueous solution of pranoprofenInfo
- Publication number
- JPH03287535A JPH03287535A JP2086670A JP8667090A JPH03287535A JP H03287535 A JPH03287535 A JP H03287535A JP 2086670 A JP2086670 A JP 2086670A JP 8667090 A JP8667090 A JP 8667090A JP H03287535 A JPH03287535 A JP H03287535A
- Authority
- JP
- Japan
- Prior art keywords
- pranoprofen
- aqueous solution
- necessary
- water
- acid
- 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.)
- Pending
Links
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229960003101 pranoprofen Drugs 0.000 title claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000008213 purified water Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- 239000012929 tonicity agent Substances 0.000 claims description 3
- 229920003169 water-soluble polymer Polymers 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000006172 buffering agent Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000007924 injection Substances 0.000 abstract description 6
- 238000002347 injection Methods 0.000 abstract description 6
- 239000000243 solution Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000007921 spray Substances 0.000 abstract description 4
- 239000003889 eye drop Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 208000008035 Back Pain Diseases 0.000 abstract description 2
- 208000003947 Knee Osteoarthritis Diseases 0.000 abstract description 2
- 208000008930 Low Back Pain Diseases 0.000 abstract description 2
- 206010034464 Periarthritis Diseases 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000007923 nasal drop Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940100656 nasal solution Drugs 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（Ａ） 産業上の利用分野
本発明は非ステロイド性の抗炎症剤として有用なプラノ
プロフェンを有効成分として含有する水溶液製剤に関す
るものである。DETAILED DESCRIPTION OF THE INVENTION (A) Field of Industrial Application The present invention relates to an aqueous solution formulation containing pranoprofen, which is useful as a non-steroidal anti-inflammatory agent, as an active ingredient.
（Ｂ） 従来の技術
プラノプロフェンは抗炎症作用を有し、変形性膝関節症
、リウマチ、肩関節周囲炎、腰痛症などの治療に有用な
化合物である。(B) Prior Art Pranoprofen has an anti-inflammatory effect and is a compound useful for treating knee osteoarthritis, rheumatism, shoulder periarthritis, low back pain, and the like.
プラノプロフェンはフェニルプロピオン酸誘導体である
が水にきわめて溶けにくく、このため貼付剤として製造
するために１〜３価の脂肪族低級アルコール、平均分子
量２００〜１０００のポリエチレングリコール及びメチ
ルエチルケトン等の有機溶剤に溶解したり、（特開昭５
９−８９６９２号公報）点眼剤として製造するためにホ
ウ酸を等張化剤として０５〜２（ｗ／ｖ）使用する方法
（特開昭６０−１８４０１３号公報）などがある。Pranoprofen is a phenylpropionic acid derivative, but it is extremely difficult to dissolve in water. Therefore, in order to manufacture it as a patch, organic solvents such as mono- to trivalent aliphatic lower alcohol, polyethylene glycol with an average molecular weight of 200-1000, and methyl ethyl ketone are used. (Unexamined Japanese Patent Publication No. 5
9-89692)) There is a method in which boric acid is used as an isotonizing agent in an amount of 05 to 2 (w/v) to produce eye drops (Japanese Patent Application Laid-open No. 184013/1983).
（Ｃ） 発明が解決しようとする問題点近年ドラッグ
デリバリ−システムという薬剤の投与方法が研究されて
いる。これは人間の疾患部位に、より選択的に薬剤を到
達させ、できる限り副作用を減らそうとするもので、投
与経路を変更し、経口的に投与されていた物を注射剤と
して量を減らしたり、点鼻薬や液剤として直接炎症部位
に投与しようというものである。(C) Problems to be Solved by the Invention In recent years, a method of administering drugs called drug delivery systems has been studied. This aims to more selectively deliver drugs to diseased areas in humans and reduce side effects as much as possible by changing the route of administration and reducing the amount of drugs that were previously administered orally by using injections. The idea is to administer it directly to the site of inflammation as a nasal spray or liquid.
本発明の目的は今までに得られているプラノプロフェン
の貼付剤や点眼剤では注射剤や噴霧剤、吸入剤として必
要な薬剤の濃度や安全性が得られないので、注射剤、噴
霧剤、吸入剤として有用なプラノプロフェン水溶液を提
供することにある。The purpose of the present invention is to provide injections, sprays, and inhalers, since the pranoprofen patches and eye drops that have been obtained so far do not have the drug concentration and safety required for injections, sprays, and inhalers. An object of the present invention is to provide an aqueous pranoprofen solution useful as an inhalant.
（Ｄ） 問題点を解決するための手段本発明者らは、
水に極めて難溶のプラノプロフェン水溶液製剤を製造す
べく鋭意検討した結果、ポリビニルピロリドンやポリエ
チレングリコール等の水溶性高分子を用いることにより
その目的を達成できることを見出だし、本発明を完成す
るに至った。(D) Means for solving the problem The inventors:
As a result of intensive studies aimed at producing an aqueous solution of pranoprofen that is extremely sparingly soluble in water, it was discovered that the objective could be achieved by using water-soluble polymers such as polyvinylpyrrolidone and polyethylene glycol, and the present invention was completed. It's arrived.
すなわち本発明は、抗炎症剤として有用なプラノプロフ
ェンを有効成分として含有する水溶液製剤においてプラ
ノプロフェンが水に澄明に溶解しており、しかも放置し
ても浮遊物や沈殿物などを生じることのない安定な液剤
であり、内用液剤または注射剤としてのみでなく眼用液
剤、点鼻液等の耳鼻用液剤、注射剤、噴霧剤、吸入剤な
どのような外用液としてきわめて有用である。That is, the present invention provides an aqueous solution formulation containing pranoprofen, which is useful as an anti-inflammatory agent, as an active ingredient, in which pranoprofen is clearly dissolved in water, and which does not produce floating matter or precipitates even if left standing. It is a stable liquid preparation with no oxidation, and is extremely useful not only as an internal solution or injection, but also as an eye solution, an otorhinolaryngology solution such as a nasal solution, and an external solution such as an injection, spray, or inhalation. .
さらに本発明の水溶液製剤はローション剤、軟膏剤、パ
スタ剤、リニメント剤などの外用製剤の製造において適
用することもできる。Furthermore, the aqueous solution preparation of the present invention can also be applied in the production of external preparations such as lotions, ointments, paste preparations, and liniments.
（Ｅ） 実施例 １ 点鼻液
ｐＨ７，ｏ Ｏ，５％ 水溶液
プラノプロフェン・・・・・・０．５ｇポリビニルピロ
リドン・・・・５．０ｇツイーン ８０・・・・・・
０．０１ｇ塩化ナトリウム・・・・・・ ０．８５ｇリ
ン酸緩衝液・・・・・・・・適量
プラノプロフェン０．５ｇをｐＨ７，０のリン酸緩衝液
８０ｍ１に分散し、ポリビニルピロリドン５．０ｇ。(E) Example 1 Nasal solution pH 7, o O, 5% Aqueous solution pranoprofen...0.5g Polyvinylpyrrolidone...5.0g Tween 80...
0.01g sodium chloride...0.85g phosphate buffer...Appropriate amount 0.5g of pranoprofen was dispersed in 80ml of phosphate buffer at pH 7.0, and polyvinylpyrrolidone 5 .0g.
ツイーン８００．０１ｇ、塩化ナトリウム０．８５ｇを
加え、加温溶解し、更にリン酸緩衝液を適量加え、全量
を１００ｍ１としてプラノプロフェン０．５％水溶液１
８０ｍ１を得た。Add 800.01 g of Tween and 0.85 g of sodium chloride, dissolve by heating, and then add an appropriate amount of phosphate buffer to make a total volume of 100 ml, and prepare 1 part of a 0.5% pranoprofen aqueous solution.
80ml was obtained.
実施例 ２ 噴霧剤
ｐＨ７，ｏ Ｏ，５％水溶液
主剤 プラノプロフェン・・・・−〇、５ｇ溶解
剤 ポリビニルピロリドン・・・ｓ、 Ｏｇ界面活
性剤 ツイーン８０・・・・・・・ｏ、 ０１ｇ保存剤
塩化ベンザルコニウム・・・Ｏ，０１ｇ等張化剤
塩化ナトリウム・・・・・・０．９ｇ精製水・・・
・・・・・・・・・・・・・適量プラノプロフェン０．
５ｇを精製水８０１１に分散し、溶解剤ポリビニルピロ
リドン５．０ｇ、界面活性剤ツイーン８００．０１ｇ、
保存剤 塩化ベンザルコニウム０．０１ｇ、等張化剤
塩化ナトリウム０．９ｇを加え、加温溶解後１Ｎ−Ｎａ
ＯＨにてｐｎを７．０に調整したのち精製水を適量追加
して１００ｍ１とし、ｐＨ７，ｏ。Example 2 Spraying agent pH 7, o O, 5% aqueous solution Main ingredient Pranoprofen...-〇, 5g Solubilizer Polyvinylpyrrolidone...s, Og Surfactant Tween 80......o, 01g Preservative: Benzalkonium chloride...O, 01g Isotonicity agent: Sodium chloride...0.9g Purified water...
・・・・・・・・・・・・・Adequate amount of pranoprofen 0.
Disperse 5g in purified water 8011, dissolve agent polyvinylpyrrolidone 5.0g, surfactant Tween 800.01g,
Preservative: benzalkonium chloride 0.01g, tonicity agent
Add 0.9 g of sodium chloride and dissolve by heating, then 1N-Na
After adjusting pn to 7.0 with OH, add an appropriate amount of purified water to make 100 ml, and pH 7.o.
プラノプロフェン０．５％水溶液を得た。A 0.5% aqueous solution of pranoprofen was obtained.
Claims (2)
ｂ）ピリジン−７−酢酸（以 下プラノプロフェン）水溶液製剤において、ポリビニル
ピロリドン、ポリエチレングリ コール等の水溶性高分子物質及び必要に応 じ酸又は塩基性物質を用いることを特徴と する水溶液製剤。(1) a-methyl-5H[1]benzopyrano(2,3-
b) An aqueous solution preparation of pyridine-7-acetic acid (hereinafter referred to as pranoprofen), characterized in that it uses a water-soluble polymeric substance such as polyvinylpyrrolidone or polyethylene glycol, and an acid or basic substance as necessary.
エチレングリコール等の水溶性 高分子物質および必要に応じ酸又は塩基性 物質を添加した精製水に加温溶解し、必要 に応じ緩衝剤、保存剤、安定化剤、等張化 剤などを加えることを特徴とするプラノプ ロフェン水溶液製剤。(2) Pranoprofen is heated and dissolved in purified water to which a water-soluble polymer substance such as polyvinylpyrrolidone or polyethylene glycol and an acid or basic substance is added as necessary, and buffering agents, preservatives, and stabilization are added as necessary. Pranoprofen aqueous solution formulation characterized by adding a tonicity agent, tonicity agent, etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2086670A JPH03287535A (en) | 1990-03-31 | 1990-03-31 | Aqueous solution of pranoprofen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2086670A JPH03287535A (en) | 1990-03-31 | 1990-03-31 | Aqueous solution of pranoprofen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03287535A true JPH03287535A (en) | 1991-12-18 |
Family
ID=13893471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2086670A Pending JPH03287535A (en) | 1990-03-31 | 1990-03-31 | Aqueous solution of pranoprofen |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03287535A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07304670A (en) * | 1994-03-15 | 1995-11-21 | Senju Pharmaceut Co Ltd | Stabilization of pranoprofen and stable aqueous pranoprofen liquid |
| WO1999004818A1 (en) * | 1997-07-24 | 1999-02-04 | Eisai Co., Ltd. | Preparation composition and process for producing the same |
| EP1108422A3 (en) * | 1999-12-18 | 2001-09-26 | Krewel Meuselbach GmbH | Medical product for moisturising and cleansing the nasal mucosa |
| US6316483B1 (en) | 1994-02-03 | 2001-11-13 | Schering Corporation | Oxymetazoline HCI and/or chlorpheniramine maleate nasal spray compositions |
| US6576677B1 (en) | 1998-08-28 | 2003-06-10 | Eisai Co., Ltd. | Medicinal compositions with relieved bitterness |
| JP2005239658A (en) * | 2004-02-27 | 2005-09-08 | Taisho Pharmaceut Co Ltd | Ophthalmic agent |
| JP2005272462A (en) * | 2004-02-27 | 2005-10-06 | Taisho Pharmaceut Co Ltd | Composition for ophthalmic solution |
| JP2006232823A (en) * | 2005-01-26 | 2006-09-07 | Rohto Pharmaceut Co Ltd | Pranoprofen-containing composition |
| US7727548B2 (en) | 2000-03-01 | 2010-06-01 | Eisai R&D Management Co., Ltd. | Rapidly disintegrable tablet containing polyvinyl alcohol |
| US7727552B1 (en) | 1997-03-28 | 2010-06-01 | Eisai R&D Management Co., Ltd. | Oral pharmaceutical preparations decreased in bitterness by masking |
| JP2012126734A (en) * | 2012-03-19 | 2012-07-05 | Taisho Pharmaceutical Co Ltd | Eyedrop medicine |
| JP2017105752A (en) * | 2015-08-31 | 2017-06-15 | ロート製薬株式会社 | Ophthalmic composition |
| JP2020506930A (en) * | 2017-02-02 | 2020-03-05 | オトラーヌム アーゲー | Intranasal composition containing betahistine |
-
1990
- 1990-03-31 JP JP2086670A patent/JPH03287535A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6316483B1 (en) | 1994-02-03 | 2001-11-13 | Schering Corporation | Oxymetazoline HCI and/or chlorpheniramine maleate nasal spray compositions |
| US6824762B2 (en) | 1994-02-03 | 2004-11-30 | Schering-Plough Healthcare Products Inc. | Nasal spray compositions |
| JPH07304670A (en) * | 1994-03-15 | 1995-11-21 | Senju Pharmaceut Co Ltd | Stabilization of pranoprofen and stable aqueous pranoprofen liquid |
| US7727552B1 (en) | 1997-03-28 | 2010-06-01 | Eisai R&D Management Co., Ltd. | Oral pharmaceutical preparations decreased in bitterness by masking |
| WO1999004818A1 (en) * | 1997-07-24 | 1999-02-04 | Eisai Co., Ltd. | Preparation composition and process for producing the same |
| US6576677B1 (en) | 1998-08-28 | 2003-06-10 | Eisai Co., Ltd. | Medicinal compositions with relieved bitterness |
| EP1108422A3 (en) * | 1999-12-18 | 2001-09-26 | Krewel Meuselbach GmbH | Medical product for moisturising and cleansing the nasal mucosa |
| US7727548B2 (en) | 2000-03-01 | 2010-06-01 | Eisai R&D Management Co., Ltd. | Rapidly disintegrable tablet containing polyvinyl alcohol |
| US8263123B2 (en) | 2000-03-01 | 2012-09-11 | Eisai R&D Management Co., Ltd. | Rapidly disintegrating tablet containing polyvinyl alcohol |
| JP2005272462A (en) * | 2004-02-27 | 2005-10-06 | Taisho Pharmaceut Co Ltd | Composition for ophthalmic solution |
| JP2005239658A (en) * | 2004-02-27 | 2005-09-08 | Taisho Pharmaceut Co Ltd | Ophthalmic agent |
| JP2006232823A (en) * | 2005-01-26 | 2006-09-07 | Rohto Pharmaceut Co Ltd | Pranoprofen-containing composition |
| JP2012126734A (en) * | 2012-03-19 | 2012-07-05 | Taisho Pharmaceutical Co Ltd | Eyedrop medicine |
| JP2017105752A (en) * | 2015-08-31 | 2017-06-15 | ロート製薬株式会社 | Ophthalmic composition |
| JP2020506930A (en) * | 2017-02-02 | 2020-03-05 | オトラーヌム アーゲー | Intranasal composition containing betahistine |
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