JPH04159228A - Preparation for drug - Google Patents
Preparation for drugInfo
- Publication number
- JPH04159228A JPH04159228A JP2281930A JP28193090A JPH04159228A JP H04159228 A JPH04159228 A JP H04159228A JP 2281930 A JP2281930 A JP 2281930A JP 28193090 A JP28193090 A JP 28193090A JP H04159228 A JPH04159228 A JP H04159228A
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- methoxyphenylazo
- imidazole
- derivative
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000003814 drug Substances 0.000 title abstract description 3
- 229940079593 drug Drugs 0.000 title abstract description 3
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 229920000858 Cyclodextrin Polymers 0.000 abstract description 13
- OQIIGZDXXJHFOW-UHFFFAOYSA-N 1H-imidazol-2-yl-(2-methoxyphenyl)diazene Chemical class COC1=CC=CC=C1N=NC1=NC=CN1 OQIIGZDXXJHFOW-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 2
- -1 (2'-methoxyphenylazo)-1H-imidazole derivative Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- IXQGZPLNCYHNKT-UHFFFAOYSA-N chembl1435053 Chemical compound COC1=CC=C(Cl)C=C1N=NC1=NC=CN1 IXQGZPLNCYHNKT-UHFFFAOYSA-N 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002949 hemolytic effect Effects 0.000 description 2
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 206010065334 Mucosal hyperaemia Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 238000009933 burial Methods 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、新規な医薬用製剤、さらに詳しくしは、種々
の薬理作用を有する２−（２’−メトキシフェニルアゾ
）−１Ｈ−イミダゾール誘導体をシクロデキストリン誘
導体で包接して水溶性化したものを含む注射剤、点滴剤
、経口投与剤などの医薬用製剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention provides novel pharmaceutical preparations, more specifically, 2-(2'-methoxyphenylazo)-1H-imidazole derivatives having various pharmacological actions. The present invention relates to pharmaceutical preparations such as injections, infusions, and oral preparations that are made water-soluble by inclusion with dextrin derivatives.
従来の技術
製薬分野においては、医薬としての薬理作用を有する水
不溶性物質を水溶性化してその有用性を高めるとともに
、調剤の容易化を図ることが重要な課題となっており、
そのため、例えば界面活性剤ミセルへの可溶化やリポソ
ーム脂質二分子膜への包埋、シクロデキストリンなどへ
の包接、合成高分子化合物又は生体内分解性高分子物質
との化学結合やマトリックスによる包埋などの手段が講
じられている。特にシクロデキストリンにより水不溶性
物質を包接して水溶性化することが積極的に試みられて
いる〔「有機合成化学協会誌」第３５巻、第１１６ペー
ジ（１９７７年）、「化学工業」第３５巻、第７１０ペ
ージ（１９８２年）〕。Conventional technology In the pharmaceutical field, it is an important issue to make water-insoluble substances that have pharmacological effects as medicines water-soluble to increase their usefulness and to facilitate their preparation.
Therefore, for example, solubilization in surfactant micelles, embedding in liposome lipid bilayer membranes, inclusion in cyclodextrins, chemical bonding with synthetic polymer compounds or biodegradable polymer substances, and encapsulation in matrices. Measures such as burial are being taken. In particular, attempts have been made to make water-insoluble substances water-soluble by including them with cyclodextrins [Journal of the Society of Organic Synthetic Chemistry, Vol. 35, p. 116 (1977), Kagaku Kogyo, No. 35 Volume, page 710 (1982)].
ところで、２−（２’−メトキシフェニルアゾ） −１
Ｈ−イミダゾール誘導体は子宮収縮作用を有することや
（特開昭５７−１５４１３０号公報）、浮腫、低血圧、
心不全及び粘膜充血などの治療に有効であること（特公
昭６０−５６１２３号公報）が知られている。By the way, 2-(2'-methoxyphenylazo) -1
H-imidazole derivatives have a uterine contraction effect (Japanese Unexamined Patent Publication No. 57-154130), edema, hypotension,
It is known to be effective in treating heart failure, mucosal hyperemia, etc. (Japanese Patent Publication No. 56123/1983).
しかしながら、この２−（２’−メトキシフェニルアゾ
）−１トイミダゾ一ル誘導体は水に溶解しにくいという
欠点を有し、シｔ；がって、その薬効を高めたり、調剤
を容易化するために、水溶性を向上させる必要がある。However, this 2-(2'-methoxyphenylazo)-1 toimidazoyl derivative has the drawback of being difficult to dissolve in water, and therefore it is difficult to improve its medicinal efficacy or facilitate preparation. Therefore, it is necessary to improve water solubility.
一般に水溶性を向上させる手段の１つしてシクロデキス
トリンで包接することが行われるが、この際用いられる
天然シクロデキストリンは、包接能や水への溶解性を左
右する空洞の径において、２−（２’−メトキシフェニ
ルアゾ）−１Ｈ−゛イミダゾール誘導体に対して適合せ
ず、その水溶性化用としては必ずしも満足しうるもので
はない。Generally, one way to improve water solubility is to include it with cyclodextrin, but the natural cyclodextrin used at this time has a cavity diameter of 2, which affects inclusion ability and water solubility. It is not compatible with -(2'-methoxyphenylazo)-1H-imidazole derivatives and is not necessarily satisfactory for making them water-soluble.
発明が解決しようとする課題
本発明は、医薬品としての種々の薬理作用を有する２−
（２’−メトキシフェニルアゾ）−１Ｈ−イミダゾール
誘導体を水溶性化して、経口的又は非経口的に投与可能
で、しかも、経時変化のない安定な医薬用製剤を提供す
ることを目的としてなされたものである。Problems to be Solved by the Invention The present invention aims to solve the following problems:
The purpose of this invention was to make a (2'-methoxyphenylazo)-1H-imidazole derivative water-soluble and to provide a stable pharmaceutical preparation that can be administered orally or parenterally and does not change over time. It is something.
課題を解決するための手段
本発明者らは、２−（２’−メトキシフェニルアゾ）−
ＩＨ−イミダゾール誘導体の製剤化について種々研究を
重ねた結果、シクロデキストリンの少なくとも１つのヒ
ドロキシル基が特定の基により修飾されたシクロデキス
トリン誘導体は、該イミダゾール誘導体に対する包接能
が非修飾シクロデキストリンに比べて著しく大きく、水
溶性化能に優れる上、非修飾シクロデキストリンよりも
溶血作用力が弱いなどの特徴を有し、このものを用いて
該イミダゾール誘導体を包接することにより、水溶性化
することができ、容易に製剤化しうろことを見い出し、
この知見に基づいて本発明を完成するに至った。Means for Solving the Problems The present inventors have discovered that 2-(2'-methoxyphenylazo)-
As a result of various studies on the formulation of IH-imidazole derivatives, it has been found that cyclodextrin derivatives in which at least one hydroxyl group of cyclodextrin is modified with a specific group have a higher inclusion ability for the imidazole derivative than unmodified cyclodextrin. It is extremely large in size, has excellent water solubilization ability, and has weaker hemolytic action than unmodified cyclodextrin.By clathrating the imidazole derivative with this substance, it can be made water-soluble. discovered scales that can be easily formulated into formulations,
Based on this knowledge, we have completed the present invention.
すなわち、本発明は、０−アルキルシクロデキストリン
、０−ヒドロキシアルキルシクロデキストリン及びＯ−
アシルシクロデキストリンの中から選ばれた少なくとも
１種のシクロデキストリン誘導体により包接された２−
（２’−メトキシフェニルアゾ）−ＩＨ−イミダゾール
誘導体を含有して成る医薬用製剤を提供するものである
。That is, the present invention provides 0-alkylcyclodextrin, 0-hydroxyalkylcyclodextrin and O-
2-
A pharmaceutical preparation containing a (2'-methoxyphenylazo)-IH-imidazole derivative is provided.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明製剤において用いられる２−（２’−メトキシフ
ェニルアゾ）−１Ｈ−イミダゾール誘導体は、−数式
（式中のＸは水素原子又はハロゲン原子である）で表わ
されるアゾ化合物又はその塩であり、このようなものと
しては、例えば２−（２’−メトキシフェニルアゾ）−
１Ｈ−イミダゾール、２−（５’−フルオロ−２′−メ
トキシフェニルアゾ）−１Ｈ−イミダゾール、２−（５
’−クロロ−２′−メトキシフェニルアゾ）−１Ｈ−イ
ミダゾール、２−（５’−ブロモ−２′−メトキシフェ
ニルアゾ）−ＩＨ−イミダゾール、２−（５’−ヨード
−２′−メトキシフェニルアゾ）−１Ｈ−イミダゾール
を挙げることができる。これらのイミダゾール誘導体は
１種用いてもよいし、２種以上を組み合わせて用いても
よい。The 2-(2'-methoxyphenylazo)-1H-imidazole derivative used in the formulation of the present invention is an azo compound or a salt thereof represented by the formula (wherein X is a hydrogen atom or a halogen atom), As such, for example, 2-(2'-methoxyphenylazo)-
1H-imidazole, 2-(5'-fluoro-2'-methoxyphenylazo)-1H-imidazole, 2-(5
'-chloro-2'-methoxyphenylazo)-1H-imidazole, 2-(5'-bromo-2'-methoxyphenylazo)-IH-imidazole, 2-(5'-iodo-2'-methoxyphenylazo) )-1H-imidazole. One type of these imidazole derivatives may be used, or two or more types may be used in combination.
本発明製剤において用いられるシクロデキストリン誘導
体は、その少なくとも１つのヒドロキシル基が、アルキ
ル基、ヒドロキシアルキル基又はアシル基で修飾されて
いればよく、特に制限されず、ａ型、２塁、γ型のいず
れであってもよい。The cyclodextrin derivative used in the preparation of the present invention is not particularly limited as long as at least one hydroxyl group is modified with an alkyl group, a hydroxyalkyl group, or an acyl group. It may be either.
該修飾基としては、例えばメチル、エチルなどのアルキ
ル基、２−ヒドロキシエテノ１２−ヒドロキシグロビル
、２．３−ジヒドロキシプロピルなどのヒドロキシアル
キル基、アセチル、プロピオニル、ブチリル、ペンタノ
イル、ヘキサノイル、ヘキサノイル、オクタノイル、ノ
ナノイル、デカノイル、ドデカノイルなどのアシル基な
どが挙げられ、これらの修飾基は１個導入されていても
よいし、同一のものが２個以上導入されていてもよく、
また、異種のものが２個以上導入されていてもよい。Examples of the modifying group include alkyl groups such as methyl and ethyl, hydroxyalkyl groups such as 2-hydroxyetheno-12-hydroxyglobyl and 2,3-dihydroxypropyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, hexanoyl, and octanoyl. , acyl groups such as nonanoyl, decanoyl, dodecanoyl, etc., and one of these modifying groups may be introduced, or two or more of the same one may be introduced,
Moreover, two or more different types may be introduced.
前記シクロデキストリン誘導体の具体例としては、アセ
チル−σ−シクロデキストリン（６）、（２，３−ジヒ
ドロキシプロピル）−ａ−シクロデキストリン（１）及
び（２）、２．６−シメチルーσ−シクロデキストリン
（６）、２．３．６−ドリメチルーａ−シクロデキスト
リン（６）、２．６−ジニチルーσ・シクロデキストリ
ン（６）などが好ましく挙げられるが、これらの中で特
に２．６−シメチルーａ−シクロデキストリン（６）が
好適である。なお、末尾の０内の数字はシクロデキスト
リン環１個に対する修飾基の導入数である。Specific examples of the cyclodextrin derivatives include acetyl-σ-cyclodextrin (6), (2,3-dihydroxypropyl)-a-cyclodextrin (1) and (2), and 2,6-dimethyl-σ-cyclodextrin. (6), 2.3.6-dimethyl-a-cyclodextrin (6), 2.6-dinityl-a-cyclodextrin (6), etc., among which 2.6-dimethyl-a-cyclodextrin (6) is particularly preferred. Cyclodextrin (6) is preferred. Note that the number within 0 at the end is the number of modifying groups introduced into one cyclodextrin ring.
シクロデキストリンに修飾基を導入する方法については
特に制限はなく、例えばアシル基を導入する場合には対
応するカルボン酸とのエステル化° 反応により、導入
することができるし、アルキル基やヒドロキシアルキル
基を導入する場合には対応する一価アルコールや多価ア
ルコールとの脱水縮合反応により導入してもよいし、エ
ポキシ環の開環反応や置換脱離反応により導入してもよ
い。There are no particular restrictions on the method of introducing a modifying group into cyclodextrin; for example, when introducing an acyl group, it can be introduced by an esterification reaction with the corresponding carboxylic acid, or an alkyl group or hydroxyalkyl group can be introduced. When introducing, it may be introduced by a dehydration condensation reaction with a corresponding monohydric alcohol or polyhydric alcohol, or may be introduced by a ring-opening reaction of an epoxy ring or a substitution/elimination reaction.
このようにして得られたシクロデキストリン誘導体は、
非修飾シクロデキストリンに比べて、修飾されることに
より２−（２’−メトキシフェニルアゾ）−ＩＨ−イミ
ダゾール誘導体の包接能、すなわちホスト−ゲスト複合
体の安定度定数が向上するとともに、複合体の水に対す
る溶解度が向上するために、より少量でより多量の２−
（２’−メトキシフェニルアゾ）−１Ｈ−イミダゾール
誘導体を可溶化することが可能となる。The cyclodextrin derivative thus obtained is
Compared to unmodified cyclodextrin, modification improves the inclusion ability of the 2-(2'-methoxyphenylazo)-IH-imidazole derivative, that is, the stability constant of the host-guest complex, and improves the stability constant of the host-guest complex. Because of the improved water solubility of 2-
It becomes possible to solubilize the (2'-methoxyphenylazo)-1H-imidazole derivative.
本発明製剤においては、前記シクロデキストリン誘導体
は１種用いてもよいし、２種以上を組み合わせて用いて
もよい。In the formulation of the present invention, one type of the cyclodextrin derivative may be used, or two or more types may be used in combination.
本発明の医薬用製剤は、−前記シクロデキストリン誘導
体の含有量が通常０．１〜２０重量％、好ましくは１〜
１５重量％の水溶液に、２−（２’−メトキシフェニル
アゾ）−１Ｈ−イミダゾール誘導体を、溶液中の濃度が
通常０．００１〜０．２重量％、好ましくは０、Ｏ１〜
０．１５重量％になるような割合で加えることにより調
製することができる。The pharmaceutical preparation of the present invention is characterized in that - the content of the cyclodextrin derivative is usually 0.1 to 20% by weight, preferably 1 to 20% by weight;
A 2-(2'-methoxyphenylazo)-1H-imidazole derivative is added to a 15% by weight aqueous solution so that the concentration in the solution is usually 0.001 to 0.2% by weight, preferably 0.
It can be prepared by adding it in a proportion such that it becomes 0.15% by weight.
発明の効果
本発明によると、特定の修飾基が導入されたシクロデキ
ストリン誘導体で２−（２’−メトキシフェニルアゾ）
−１Ｈ−イミダゾール誘導体を包接することにより、非
修飾シクロデキストリンで包接するのに比べて、より少
量で該イミダゾール誘導体を所望の濃度にまで可溶化す
ることができる上、極めて優れた長期保存安定性を有す
る医薬用製剤を与えることができる。Effects of the Invention According to the present invention, 2-(2'-methoxyphenylazo) is a cyclodextrin derivative into which a specific modifying group has been introduced.
By including the -1H-imidazole derivative, it is possible to solubilize the imidazole derivative to a desired concentration with a smaller amount than when including it with unmodified cyclodextrin, and it also has extremely excellent long-term storage stability. It is possible to provide a pharmaceutical formulation having the following.
本発明の医薬用製剤は、注射剤、点滴剤、経口投与剤な
どの形で容易に投与することができるが、該シクロデキ
ストリン誘導体の溶血作用力が非修飾シクロデキストリ
ンよりも弱いことから、特に注射剤や点滴剤として用い
る場合、人体に対する作用の上で有利である。The pharmaceutical preparation of the present invention can be easily administered in the form of an injection, a drip, an oral preparation, etc. However, since the hemolytic action of the cyclodextrin derivative is weaker than that of unmodified cyclodextrin, When used as an injection or infusion, it is advantageous in terms of its effect on the human body.
実施例
次に、実施例により本発明をさらに詳細に説明するが、
本発明はこれらの例によってなんら限定されるものでは
ない。Examples Next, the present invention will be explained in more detail with reference to examples.
The present invention is not limited in any way by these examples.
実施例１
アセチル−σ−シクロデキストリン（６）１重量％濃度
の水溶液を調製し、これに過剰の２−（５’−クロロ−
２′−メトキシフェニルアゾ）−１Ｈ−イミダゾールを
加え、室温で１５分間超音波処理したのち、０．４５μ
ｍのフィルターでろ過した。このろ液及びさらにろ液を
４０℃で３か月間保存したものに含まれる２−（５’−
クロロ−２′・メトキシフェニルアゾ）−１８−イミダ
ゾールをＨＰＬＣにより定量した。その結果を表に示す
。Example 1 A 1% by weight aqueous solution of acetyl-σ-cyclodextrin (6) was prepared, and an excess of 2-(5'-chloro-
After adding 2'-methoxyphenylazo)-1H-imidazole and sonicating at room temperature for 15 minutes, 0.45μ
It was filtered with a filter of m. The 2-(5'-
Chloro-2'.methoxyphenylazo)-18-imidazole was determined by HPLC. The results are shown in the table.
実施例２〜１６
表に示す種類と濃度シクロデキストリン誘導体水溶液を
調製し、実施例１と同様にして実施した。Examples 2 to 16 Aqueous solutions of cyclodextrin derivatives of types and concentrations shown in the table were prepared and carried out in the same manner as in Example 1.
その結果を表に示す。The results are shown in the table.
比較例
ａ−シクロデキストリン１重量％濃度の水溶液を調製し
、実施例１と同様にして実施した。その結果を表に示す
。Comparative Example a - An aqueous solution of cyclodextrin having a concentration of 1% by weight was prepared and carried out in the same manner as in Example 1. The results are shown in the table.
２） ＣＭＰＡＩ ： ２−（５’−クロロ−２′−
メトキシフェニルアゾ）−１Ｈ−イミダゾール
３） ＣＭＰＡＩの可溶化量の数値は高い方がよい。2) CMPAI: 2-(5'-chloro-2'-
Methoxyphenylazo)-1H-imidazole 3) The higher the value of the solubilized amount of CMPAI, the better.
表から明らかなように、本発明に係るシクロデキストリ
ン誘導体は、２−（５’−クロロ−２′メトキシフエニ
ルアゾ）−ＬＨ−イミダゾールの可溶化に対して有効で
あることが分かる。As is clear from the table, the cyclodextrin derivative according to the present invention is effective in solubilizing 2-(5'-chloro-2'methoxyphenylazo)-LH-imidazole.
Claims (1)
アルキルシクロデキストリン及び０−アシルシクロデキ
ストリンの中から選ばれた少なくとも１種のシクロデキ
ストリン誘導体により包接された２−（２′−メトキシ
フェニルアゾ）−１Ｈ−イミダゾール誘導体を含有して
成る医薬用製剤。1 2-(2'-methoxyphenylazo)-1H- clathrated with at least one cyclodextrin derivative selected from 0-alkylcyclodextrin, 0-hydroxyalkylcyclodextrin, and 0-acylcyclodextrin A pharmaceutical preparation comprising an imidazole derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2281930A JPH04159228A (en) | 1990-10-22 | 1990-10-22 | Preparation for drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2281930A JPH04159228A (en) | 1990-10-22 | 1990-10-22 | Preparation for drug |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04159228A true JPH04159228A (en) | 1992-06-02 |
Family
ID=17645923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2281930A Pending JPH04159228A (en) | 1990-10-22 | 1990-10-22 | Preparation for drug |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04159228A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999005110A1 (en) * | 1997-07-25 | 1999-02-04 | Ishihara Sangyo Kaisha Ltd. | Amorphous benzoylurea and vermicides for warm-blooded animals containing the same as the active ingredient |
-
1990
- 1990-10-22 JP JP2281930A patent/JPH04159228A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999005110A1 (en) * | 1997-07-25 | 1999-02-04 | Ishihara Sangyo Kaisha Ltd. | Amorphous benzoylurea and vermicides for warm-blooded animals containing the same as the active ingredient |
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