JPS6272688A - Tipepidine citrate-containing composition - Google Patents
Tipepidine citrate-containing compositionInfo
- Publication number
- JPS6272688A JPS6272688A JP60211966A JP21196685A JPS6272688A JP S6272688 A JPS6272688 A JP S6272688A JP 60211966 A JP60211966 A JP 60211966A JP 21196685 A JP21196685 A JP 21196685A JP S6272688 A JPS6272688 A JP S6272688A
- Authority
- JP
- Japan
- Prior art keywords
- tipepidine citrate
- tipepidine
- cyd
- citrate
- cyclodextrin
- 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.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規なりエン酸チペピジン含有組取物に関する
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel composition containing tipepidine enoate.
クエン酸チペピジンはリン酸コディンと同等又はそれ以
上の鎮咳作用を有すると共に去痰作用を併有する物質で
あり、しかも非麻薬性であるため普通薬として扱うこと
ができることから、鎮咳去痰剤等として広く使用されて
いる。Tipepidine citrate is a substance that has an antitussive effect equal to or greater than that of codine phosphate, and also has an expectorant effect. Furthermore, it is non-narcotic and can be treated as an ordinary drug, so it is widely used as an antitussive expectorant. has been done.
しかしながら、クエン酸チペピジンは強い苦味を有する
ため、特に液剤とした場合服用し難いという欠点があ）
、自ずからその剤形は錠剤及びカプセル剤に限られてい
た。However, tipepidine citrate has a strong bitter taste, which makes it difficult to take, especially when made into a liquid form.)
However, its dosage form was naturally limited to tablets and capsules.
しかし、小児等に服用させる場合には、液剤あるいはド
ライシロップ剤等の剤形の方が投与が容易であることか
ら、クエン酸チペピジンの苦味の改善が所望されていた
。However, since it is easier to administer to children and the like in dosage forms such as liquid or dry syrup, it has been desired to improve the bitter taste of tipepidine citrate.
斯かる実状において、本発明者は鋭意研究を行なった結
果、クエン酸チペピジンに特定量のシフロブキス） Ｉ
Ｊンｒｃｙｎ）、を配合すれば当該苦味が著しく低減さ
れ、しかもクエン酸チペピジンの水への溶解速度が促進
されること、従ってクエン酸チペピジンの液剤又はドラ
イシロップの調製が可能となることを見出し、本発明を
完成した。Under such circumstances, the present inventor conducted intensive research and found that tipepidine citrate plus a specific amount of shifrobukis) I
found that the bitterness can be significantly reduced and the rate of dissolution of tipepidine citrate in water can be accelerated by blending with tipepidine citrate, thus making it possible to prepare a liquid preparation or dry syrup of tipepidine citrate. The invention has been completed.
すなわち本発明は、クエン酸チペピジン及びこれ１モル
に対し０．５モル以上のシクロデキストリンを含有する
ことを特徴とするクエン酸チペピジン含有組成物を提供
するものである。That is, the present invention provides a tipepidine citrate-containing composition characterized by containing tipepidine citrate and 0.5 mole or more of cyclodextrin per mole thereof.
本発明に用いられるＣｙＤは、でんぷん、あるいはデキ
ストリンにアミラーゼを作用して得られる、６〜８個の
Ｄ−グルコース単位がＱ−１，４−グルコシド結合によ
り結合した環状構造を有する化合物で、内部に直径６〜
ＩＯＡの空洞を有する。CyD used in the present invention is a compound obtained by acting amylase on starch or dextrin and has a cyclic structure in which 6 to 8 D-glucose units are linked by Q-1,4-glucosidic bonds, and has an internal diameter 6~
It has a cavity of IOA.
Ｄ−グルコースの構成単位の数によシａ−型、β−型及
びγ−型がある。There are a-type, β-type and γ-type depending on the number of constituent units of D-glucose.
ＣｙＤは、クエン酸チペピジン１モルに対し ＣｙＤを
０．５モル以上の割合で使用すれば本発明効果が奏され
るのが、０．５〜４モル使用するのが特に好ましい。The effects of the present invention can be achieved when CyD is used in a proportion of 0.5 mole or more per mole of tipepidine citrate, but it is particularly preferable to use 0.5 to 4 moles.
本発明のクエン酸チペピジン含有組成物は、例えばクエ
ン酸チペピジンとＣｙＤとを前記割合で含む水浴液を調
製した後、溶媒を除去する方法によシ調製される。斯く
して得られる組成物は、塊状あるいは粉末状であり、苦
味がないうえに溶解性の高いものなのでドライシロップ
剤に適している。The tipepidine citrate-containing composition of the present invention is prepared, for example, by a method in which a water bath solution containing tipepidine citrate and CyD in the above ratio is prepared, and then the solvent is removed. The composition thus obtained is in the form of a lump or powder, has no bitter taste, and is highly soluble, making it suitable for use as a dry syrup.
このものは、液剤に使用することができるが、液剤の場
合は溶剤に単にクエン酸チペピジンとＣｙＤを添加する
方法によっても本発明効果を奏することができる。This product can be used in a liquid formulation, but in the case of a liquid formulation, the effects of the present invention can also be achieved by simply adding tipepidine citrate and CyD to the solvent.
本発明組成物に使用されるＣｙＤは、Ｑ −ＣｙＤ 。CyD used in the composition of the present invention is Q-CyD.
β−ＣＹＤ 、γ−ＣｙＤのいずれであってもよく、ま
た２種以上を組合せて使用することができるが、特に苦
味の軽減効果の点ではβ−ＣＹＤが好ましい。Either β-CYD or γ-CyD may be used, and two or more types can be used in combination, but β-CYD is particularly preferred from the viewpoint of reducing bitterness.
本発明組成物には、更に生薬成分、洋薬等の薬物、防腐
剤、矯味剤、安定化剤等の成分を配合することができる
。The composition of the present invention may further contain ingredients such as crude drug ingredients, drugs such as Western medicine, preservatives, flavoring agents, and stabilizers.
しかしながら、本発明組成物にこれら成分を配合する場
合、ＣｙＤとしてβ−ＣｙＤのみを用いると、防腐剤、
矯味剤あるいは安定化剤等の成分、就中パラオキシ安息
香酸エステル類、安息香酸ナトリウム等の防腐剤の存在
によって経時的におり（結晶）が発生する。However, when blending these components into the composition of the present invention, if only β-CyD is used as CyD, preservatives,
Due to the presence of components such as flavoring agents or stabilizers, and preservatives such as paraoxybenzoic acid esters and sodium benzoate, crystals (crystals) are generated over time.
しかし、本発明者は、この場合、ｃｙＤとしてβ−ＣＹ
Ｄにα−ＣＹＤを添加したものを使用することによって
、その防腐効果を損なうことなくおりの発生を防止でき
ることを見出した。Ｑ −（ＪＤの添加割合は、β−Ｃ
ｙＤ１モルニ対しテＱ −ＣｙＤ ０．２モル以上、特
に０．２〜１．０モルが好適である。However, in this case, the inventors determined that β-CY as cyD
It has been found that by using D with α-CYD added, it is possible to prevent the formation of ooze without impairing its antiseptic effect. Q - (The addition ratio of JD is β-C
0.2 mol or more, particularly 0.2 to 1.0 mol of TeQ-CyD per 1 mol of yD is suitable.
本発明に使用されるａ−５β−又はｒ −ＣＹＤはクエ
ン酸チペピジンの溶解性を促進する作用を有する。第１
図に示す如く、溶解性はα−（ＪＤで約４倍、β−Ｃｙ
Ｄ 、 ｒ −ＣｙＤで約６倍向上した。The a-5β- or r-CYD used in the present invention has the effect of promoting the solubility of tipepidine citrate. 1st
As shown in the figure, the solubility is α-(about 4 times JD, β-Cy
D, r-CyD improved about 6 times.
本発明組成物は、苦味が少ないため服用し易いクエン酸
テベピジン含有液剤として有効に利用することができる
。また、溶解性もよいのでドライシロップ剤とすること
ができる。The composition of the present invention can be effectively used as a liquid preparation containing tebepidine citrate, which is easy to take because of its low bitterness. In addition, since it has good solubility, it can be made into a dry syrup.
次に実施例を挙げて説明する。 Next, an example will be given and explained.
試験例１
４Ｘ１０ Ｍクエン酸チペピジン溶液に、クエン酸チ
ペピジンに対して０〜４倍モルのＱ−、β−又はｒ−（
ＪＤを添加した。この溜液の苦味をパネラ−１０名が官
能計画した。結果を次の表１−ａ−Ｃに示す。Test Example 1 Q-, β- or r-(
JD was added. Ten panelists conducted a sensory evaluation of the bitterness of this collected liquid. The results are shown in Table 1-a-C below.
表１−ａ
表１−ｂ
表１−ｃ
：−
表１−ａ−ｃから、いずれのＣＹＤでも苦味軽減効果は
あるが、特にβ−ＣＪＤの効果が顕著なこと、そして配
合割合はクエン酸チペピジン１モルに対し０．５モル以
上、更に実用的な観点から０．５〜４モルの範囲が好ま
しいことが分かる。Table 1-a Table 1-b Table 1-c:- Table 1-a-c shows that all CYDs have the effect of reducing bitterness, but the effect of β-CJD is particularly remarkable, and that the blending ratio is citric acid It can be seen that the amount is preferably 0.5 mol or more per 1 mol of tipepidine, and more preferably in the range of 0.5 to 4 mol from a practical standpoint.
試験例２
クエン酸チペピジン１２０ｑとα−９β−又はｒ −Ｃ
ＹＤを精製水１０ｄに加え単に混合する方法、又は予め
クエン酸チペピジン１２０岬とＱ−、β−又はγ−Ｃｙ
Ｄの包接体を調製し、これを精製水１０−に加え混合す
る方法によりクエン酸チペピジン及びＣＹＤの混合液を
調製し、溶解性を判定した。なお、混合は２５℃、回転
数３０回／分の条件で行なった。結果を表２に示す。Test Example 2 Tipepidine citrate 120q and α-9β- or r-C
A method of simply adding YD to 10 d of purified water and mixing, or preliminarily mixing Q-, β- or γ-Cy with tipepidine citrate 120 d.
A mixed solution of tipepidine citrate and CYD was prepared by preparing a clathrate of D, adding it to purified water 10- and mixing it, and its solubility was determined. Note that the mixing was performed at 25° C. and at a rotation speed of 30 times/min. The results are shown in Table 2.
以下余白
表 ２
来 クエン酸チペピジン
親判定基準
◎ ２分以内で全て溶解した
０ １０分以内で全て溶解した
Ｘ ３０分以上でも不溶分が残存した 、表２から、
ｃｙＤの添加によってクエン酸チペピジンの溶解速度が
上昇すること、単に混合したものでも充分効果はみられ
るが、特に予め固形の包接体を形成させると速やかに溶
解することが分がる。Margin table below 2 From Table 2, Tipepidine Citrate Parent Judgment Criteria ◎ All dissolved within 2 minutes 0 All dissolved within 10 minutes X Insoluble matter remained even after 30 minutes or more.
It has been found that the dissolution rate of tipepidine citrate increases by the addition of cyD, and although a sufficient effect can be seen even when the mixture is simply mixed, the dissolution is particularly rapid when a solid clathrate is formed in advance.
実施例１
゛ クエン酸チペピジン２．４２とａ −ＣｙＤ １０
ｆ Ｋ精製水２０−を加え室温で１２時間攪拌し、そ
の後、減圧で濃縮乾固し、モル比１：２の包接体を得た
。Example 1 ゛ Tipepidine citrate 2.42 and a-CyD 10
f K purified water 20°C was added and stirred at room temperature for 12 hours, and then concentrated to dryness under reduced pressure to obtain a clathrate with a molar ratio of 1:2.
実施例２
クエン酸チペピジン２．０２とβ−（ＪＤ １０ ｆに
精製水２０ ｍｌを加え室温で１２時間攪拌し、その後
、減圧で濃縮乾固し、モル比１：２の包接体を得た。Example 2 20 ml of purified water was added to 2.02 ml of tipepidine citrate and β-(JD 10 f), stirred at room temperature for 12 hours, and then concentrated to dryness under reduced pressure to obtain a clathrate with a molar ratio of 1:2. Ta.
実施例３
クエン酸チペピジン３．６１とｒ −ＣｙＤ １０ ｔ
に精製水２０−を加え室温で１２時間攪拌し、その後、
減圧で濃縮乾固し、モル比１：１の包接体を得た。Example 3 Tipepidine citrate 3.61 and r-CyD 10t
Add 20% of purified water to the solution, stir at room temperature for 12 hours, and then
The mixture was concentrated to dryness under reduced pressure to obtain a clathrate with a molar ratio of 1:1.
実施例４
次に示す組成のクエン酸チペピジン含有液剤（１日ｔ５
０ｄ）を下記方法により調製した。Example 4 A liquid preparation containing tipepidine citrate having the following composition (1 day t5
0d) was prepared by the following method.
（組成）
クエン酸チペピジン １２０”？パラオキ
シ安息香酸ブチル ６白ＩＩ
１２００β−Ｃ）ＦＤ
６００Ｑ−Ｃ’！Ｄ
１２０クエン酸 ３０
香料 ５０精製水
適量
Ｃ調製法）
クエン酸チペピジン、β−ＣｙＤ及びＱ −ＣｙＤを５
０〜６０℃の精製水に攪拌溶解する。別にパラオキシ安
息香酸ブチル、白糖を精製水・に加温しながら溶解する
。両者を合わせ３０℃以下に冷却し香料を加える。(Composition) Tipepidine citrate 120"?Butyl paraoxybenzoate 6 white II
1200β-C) FD
600Q-C'! D
120 citric acid 30
Fragrance 50 Purified water
Appropriate amount C preparation method) Tipepidine citrate, β-CyD and Q-CyD
Stir and dissolve in purified water at 0 to 60°C. Separately, dissolve butyl paraoxybenzoate and white sugar in purified water while heating. Combine the two, cool to below 30°C, and add flavoring.
試験例３
実施例４と同様にして次の表３に示す組成の対照°品及
び本発明品２．３を調製した。次いで実施例４の本発明
品（以下、本発明品１という）及びこれらの苦味、経時
安定性、及び防腐力について試験を行なった。Test Example 3 In the same manner as in Example 4, a control product and a product 2.3 of the present invention having the compositions shown in Table 3 below were prepared. Next, the product of the present invention of Example 4 (hereinafter referred to as "present product 1") and its bitterness, stability over time, and preservative power were tested.
表 ３ 注）いずれも全ｔ５０−となるように調製した。Table 3 Note) All samples were prepared to have a total t50-.
（１） 苦味 パネラ−１０名が官能評価した。結果を表４に示す。(1) Bitterness A sensory evaluation was conducted by 10 panelists. The results are shown in Table 4.
以下余白 表 ４ ◆実施例４で得たもの（以下同じ）。Margin below Table 4 ◆What was obtained in Example 4 (the same applies below).
（１） 経時安定性
４℃で６か月間保存し、経時的なおり（結晶）の発生状
態を視覚的に判定した。結果を表５に示す。(1) Stability over time The product was stored at 4°C for 6 months, and the state of occurrence of crystals (crystals) over time was visually determined. The results are shown in Table 5.
表 ５
注） 判定基準
−発生せず
± やや発生
十 発生
（１１０防腐力
次の表６に示す微生物を本発明品又は比較品の原液に加
え、その防腐力を試験した。初期供試菌数は約５ Ｘ
１０５個／ｄとし、４週間後の菌数を調べた。結果を表
６に示す。Table 5 Note) Judgment criteria - No occurrence ± Slight occurrence 10 Occurrence (110 Preservative power) The microorganisms listed in Table 6 below were added to the stock solution of the inventive product or comparative product, and the preservative power was tested. Initial number of bacteria tested is about 5X
The number of bacteria was determined at 105 cells/d after 4 weeks. The results are shown in Table 6.
表 ６ 注）「−」は１個／＃Ｉ／以下であることを示す。Table 6 Note) "-" indicates 1 piece/#I/ or less.
本発明品２は他の物に比べ防腐力が小さく、前記（１１
）で生じたおりが主としてパラオキシ安息香酸ブチルと
β−ＣｙＤとから成るものであることが分かる。Product 2 of the present invention has a lower preservative power than other products, and has the above-mentioned (11
It can be seen that the sludge produced in ) is mainly composed of butyl paraoxybenzoate and β-CyD.
試験（＋）、（１）及び（ｌｉＤの結果から、クエン酸
チペピジンにａ−又はβ−ＣｙＤを併用すれば、いずれ
の（ＪＤによっても苦味を改善することができるが、場
合によっては、クエン酸チペピジン製剤中の他成分の効
果を損うことがあることが判明した。すなわち、β−Ｃ
ｙＩ）はクエン酸チペピジンの苦味防止の点では他のａ
−又はｒ −ＣＹＤより有効であるが、これ単独でパラ
オキシ安息香酸ブチルと共存させると経時的におりを生
じパラオキシ安息香酸の防腐力を損ってしまう。尤もこ
のような場合には、やはり上記結果から明らかな如く、
更にａ−ＣｙＤを併用することＫより斯かる弊害を除く
ことができる。From the results of Tests (+), (1) and (liD), if tipepidine citrate is used in combination with a- or β-CyD, bitterness can be improved by either (JD), but in some cases It was found that the effects of other ingredients in tipepidine acid preparations may be impaired, i.e., β-C
yI) is superior to other a in terms of preventing the bitterness of tipepidine citrate.
Although it is more effective than - or r-CYD, if it is used alone in the coexistence with butyl paraoxybenzoate, it will cause oozing over time and impair the preservative power of paraoxybenzoic acid. Of course, in such a case, as is clear from the above results,
Further, by using a-CyD in combination with K, such adverse effects can be eliminated.
実施例５
次に示す組成のクエン−酸チペピジン配合製剤（１日量
３０−）を下記方法により調製した。Example 5 A tipepidine citrate-acid combination preparation (daily dose: 30 -) having the composition shown below was prepared by the following method.
（組成）
クエン酸テづピジン ６０■マレイン酸
クロルフェニラミン １２■無水カフエイン
６０安息香酸ナトリウム
３０パラオキシ安息香酸ブチル ３白糖
１０００β−ＣｙＤ
２５０ａ−ｃｙＤ
２００クエン酸 ３
０香料 ４５精製水
適量
（調製法）
実施例４と同様にして調製した。(Composition) Tedupidine citrate 60 ■ Chlorpheniramine maleate 12 ■ Anhydrous caffeine
60 Sodium Benzoate
30-butyl paraoxybenzoate 3-white sugar
1000β-CyD
250a-cyD
200 citric acid 3
0 fragrance 45 purified water
Appropriate amount (preparation method) Prepared in the same manner as in Example 4.
試験例４
実施例５で得たクエン酸チペピジン配合製剤の苦味、及
び経時安定性について試験を行なった。Test Example 4 The tipepidine citrate combination preparation obtained in Example 5 was tested for bitterness and stability over time.
（１）苦味 パネラ−１０名が官能評価した。結果を表７に示す。(1) Bitterness A sensory evaluation was conducted by 10 panelists. The results are shown in Table 7.
表 ７
（１） 経時安定性
４℃で６か月間保存し、経時的なおり（結晶）の発生状
態を視覚的に判定した。結果を表８に示す。Table 7 (1) Stability over time The product was stored at 4°C for 6 months, and the state of occurrence of crystals (crystals) over time was visually determined. The results are shown in Table 8.
表 ８ 注）判定基準は表５と同じ。Table 8 Note) Judgment criteria are the same as Table 5.
第１図はクエン酸チペピジンとＣｙＤの溶解度相図でお
る。
以上Figure 1 shows the solubility phase diagram of tipepidine citrate and CyD. that's all
Claims (1)
ル以上のシクロデキストリンを含有することを特徴とす
るクエン酸チペピジン含有組成物。 ２、シクロデキストリンが、β−シクロデキストリン１
モルとα−シクロデキストリン０．２モル以上の割合の
混合物である特許請求の範囲第１項記載のクエン酸チペ
ピジン含有組成物。 ３、パラオキシ安息香酸エステル類又は／及び安息香酸
塩を含有するものである特許請求の範囲第２項記載のク
エン酸チペピジン含有組成物。[Scope of Claims] 1. A composition containing tipepidine citrate, which contains tipepidine citrate and 0.5 mol or more of cyclodextrin per 1 mol thereof. 2. Cyclodextrin is β-cyclodextrin 1
The tipepidine citrate-containing composition according to claim 1, which is a mixture of mol and α-cyclodextrin in a ratio of 0.2 mol or more. 3. The tipepidine citrate-containing composition according to claim 2, which contains paraoxybenzoic acid esters or/and benzoates.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60211966A JPS6272688A (en) | 1985-09-25 | 1985-09-25 | Tipepidine citrate-containing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60211966A JPS6272688A (en) | 1985-09-25 | 1985-09-25 | Tipepidine citrate-containing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6272688A true JPS6272688A (en) | 1987-04-03 |
| JPH0523244B2 JPH0523244B2 (en) | 1993-04-02 |
Family
ID=16614654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60211966A Granted JPS6272688A (en) | 1985-09-25 | 1985-09-25 | Tipepidine citrate-containing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6272688A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04221379A (en) * | 1990-03-27 | 1992-08-11 | Roussel Uclaf | New composite of thiaprofenic acid or soluble or partially soluble ester thereof with cyclodextrin or derivative thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50116617A (en) * | 1974-02-25 | 1975-09-12 | ||
| JPS5486607A (en) * | 1977-12-23 | 1979-07-10 | Yoshinobu Nakai | Solid pharmaceutical composition |
| JPS59152320A (en) * | 1983-02-17 | 1984-08-31 | Takeda Chem Ind Ltd | Aqueous pharmaceutical preparation |
-
1985
- 1985-09-25 JP JP60211966A patent/JPS6272688A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50116617A (en) * | 1974-02-25 | 1975-09-12 | ||
| JPS5486607A (en) * | 1977-12-23 | 1979-07-10 | Yoshinobu Nakai | Solid pharmaceutical composition |
| JPS59152320A (en) * | 1983-02-17 | 1984-08-31 | Takeda Chem Ind Ltd | Aqueous pharmaceutical preparation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04221379A (en) * | 1990-03-27 | 1992-08-11 | Roussel Uclaf | New composite of thiaprofenic acid or soluble or partially soluble ester thereof with cyclodextrin or derivative thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0523244B2 (en) | 1993-04-02 |
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