JPWO2015137327A1 - ジブチルヒドロキシトルエンの安定化方法 - Google Patents
ジブチルヒドロキシトルエンの安定化方法 Download PDFInfo
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- JPWO2015137327A1 JPWO2015137327A1 JP2016507755A JP2016507755A JPWO2015137327A1 JP WO2015137327 A1 JPWO2015137327 A1 JP WO2015137327A1 JP 2016507755 A JP2016507755 A JP 2016507755A JP 2016507755 A JP2016507755 A JP 2016507755A JP WO2015137327 A1 JPWO2015137327 A1 JP WO2015137327A1
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- Prior art keywords
- dibutylhydroxytoluene
- container
- liquid agent
- pouring
- wall surface
- 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.)
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Links
- 235000010354 butylated hydroxytoluene Nutrition 0.000 title claims abstract description 146
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
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- -1 polybutylene terephthalate Polymers 0.000 claims abstract description 82
- 150000003839 salts Chemical class 0.000 claims abstract description 81
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229960003101 pranoprofen Drugs 0.000 claims abstract description 38
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 claims abstract description 36
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- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims abstract description 23
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Abstract
Description
項1. (A)ジブチルヒドロキシトルエンと、
(B)プラノプロフェン及び/又はその薬学的に許容される塩と、
(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロール誘導体よりなる群から選択される少なくとも1種と、
を含有する液剤が、容器に収容されてなるジブチルヒドロキシトルエン含有製品であって、
前記容器が、前記液剤を収容する容器本体部と、前記容器本体部に収容された液剤を注出する注出口を有する注出部と、前記注出口をふさぐ蓋部とを備え、
前記注出部の内部空間の壁面、及び前記蓋部において前記注出口と対向する壁面の少なくとも一方が、ポリブチレンテレフタレートを含む樹脂で構成されていることを特徴とする、
ジブチルヒドロキシトルエン含有製品。
項2. 前記液剤が、更にタウリンを含有する、項1に記載のジブチルヒドロキシトルエン含有製品。
項3. 前記注出部が、前記液剤を液滴状で注出するノズルであり、当該ノズルの内部空間の壁面がポリブチレンテレフタレートを含む樹脂で構成されている、項1又は2に記載のジブチルヒドロキシトルエン含有製品。
項4. 前記容器本体部が、ポリエチレンテレフタレートを含む樹脂で構成されている、項1〜3のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項5. 前記液剤が、更にホウ酸緩衝剤を含む、項1〜4のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項6. 前記(C)成分が、コンドロイチン硫酸エステル、アスパラギン酸、それらの薬学的に許容される塩、及びシアノコバラミンよりなる群から選択される少なくとも1種である、項1〜5のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項7. 前記(C)成分として、コンドロイチン硫酸エステル及び/又はその薬学的に許容される塩と、アスパラギン酸及び/又はその薬学的に許容される塩とを含む、項1〜6のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項8. 前記液剤において、前記(A)成分が0.00001〜0.005w/v%、前記(B)成分が0.005〜0.5w/v%、及び前記(C)成分が0.0005〜5w/v%含まれる、項1〜7のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項9. 前記液剤が点眼剤である、項1〜8のいずれかに記載のジブチルヒドロキシトルエン含有製品。
項10. (A)ジブチルヒドロキシトルエンと、
(B)プラノプロフェン及び/又はその薬学的に許容される塩と、
を含有する液剤におけるジブチルヒドロキシトルエンの安定化方法であって、
前記液剤に、(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロール誘導体よりなる群から選択される少なくとも1種を配合し、且つ
液剤を収容する容器本体部と、前記容器本体部に収容された液剤を注出する注出口を有する注出部と、前記注出口をふさぐ蓋部とを備え、前記注出部の内部空間の壁面、及び前記蓋部において前記注出口と対向する壁面の少なくとも一方がポリブチレンテレフタレートを含む樹脂で構成されている容器に、前記液剤を収容することを特徴とする、
安定化方法。
項11. 前記液剤に、更にタウリンを配合する、項10に記載の安定化方法。
項12. 前記注出部が、前記液剤を液滴状で注出するノズルであり、当該ノズルの内部空間の壁面がポリブチレンテレフタレートを含む樹脂で構成されている、項10又は11に記載の安定化方法。
項13. 前記容器本体部が、ポリエチレンテレフタレートを含む樹脂で構成されている、項10〜12のいずれかに記載の安定化方法。
項14. 前記液剤が、更にホウ酸緩衝剤を含む、項10〜13のいずれかに記載の安定化方法。
項15. 前記(C)成分が、コンドロイチン硫酸エステル、アスパラギン酸、それらの薬学的に許容される塩、及びシアノコバラミンよりなる群から選択される少なくとも1種である、項10〜14のいずれかに記載の安定化方法。
項16. 前記(C)成分として、コンドロイチン硫酸エステル及び/又はその薬学的に許容される塩と、アスパラギン酸及び/又はその薬学的に許容される塩とを含む、項10〜15のいずれかに記載の安定化方法。
項17. 前記液剤において、前記(A)成分が0.00001〜0.005w/v%、前記(B)成分が0.005〜0.5w/v%、及び前記(C)成分が0.0005〜5w/v%含まれる、項10〜16のいずれかに記載の安定化方法。
項18. 前記液剤が点眼剤である、項10〜17のいずれかに記載の安定化方法。
本発明のBHT含有製品は、(A)ジブチルヒドロキシトルエンと、(B)プラノプロフェン及び/又はその薬学的に許容される塩と、(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロール誘導体よりなる群から選択される少なくとも1種を含有する液剤が、注出部の内部空間の壁面及び/又は蓋部において注出部の注出口と対向する壁面がポリブチレンテレフタレートを含む樹脂で構成された容器に収容されていることを特徴とする。以下、本発明のBHT含有製品について、詳述する。
本発明のBHT含有製品において、容器に収容する液剤は、ジブチルヒドロキシトルエン((A)成分と表記することもある)を含有する。ジブチルヒドロキシトルエンは、2,6−ジ−tert−ブチル−4−メチルフェノール、BHT、DBPCとも称され、抗酸化剤として公知の化合物である。当該液剤において、ジブチルヒドロキシトルエンは、プラノプロフェン及び/又はその塩の熱安定性向上を図ると共に、液剤中で酸化防止作用を発揮し、必要に応じて添加される薬理成分や添加剤等の安定性の向上にも寄与する成分である。
コンドロイチン硫酸エステル及び/又はその塩を使用する場合:好ましくは0.005〜5w/v%、更に好ましくは0.01〜1w/v%、特に好ましくは0.05〜0.5w/v%。
アスパラギン酸及び/又はその塩を使用する場合:好ましくは0.01〜5w/v%、更に好ましくは0.05〜2w/v%、特に好ましくは0.1〜1w/v%。
アルギン酸、その誘導体及び/又はそれらの塩を使用する場合:好ましくは0.001〜1w/v%、更に好ましくは0.005〜0.2w/v%、特に好ましくは0.01〜0.1w/v%。
シアノコバラミンを使用する場合:好ましくは0.001〜0.1w/v%、更に好ましくは0.002〜0.05w/v%、特に好ましくは0.004〜0.02w/v%。
パンテノールを使用する場合:好ましくは0.001〜1w/v%、更に好ましくは0.
005〜0.5w/v%、特に好ましくは0.01〜0.1w/v%。
トコフェロール及び/又はその誘導体を使用する場合:好ましくは0.0005〜1w/v%、更に好ましくは0.001〜0.1w/v%、特に好ましくは0.005〜0.05w/v%。
コンドロイチン硫酸エステル及び/又はその塩と、アスパラギン酸及び/又はその塩とを組み合わせて使用する場合:コンドロイチン硫酸エステル及び/又はその塩が好ましくは0.005〜5w/v%、更に好ましくは0.05〜0.5w/v%、且つアスパラギン酸及び/又はその塩が好ましくは0.01〜5w/v%、更に好ましくは0.1〜1w/v%。
本発明のBHT含有製品では、前記液剤を収容するために、容器本体部と注出部と蓋部とを備え、前記注出部の内部空間の壁面及び/又は蓋部において注出部の注出口と対向する壁面がポリブチレンテレフタレートを含む樹脂で構成されている容器が使用される。
前記容器を構成する容器本体部とは、前記液剤を収容する部位である。当該容器本体部の形状、大きさについては、特に制限されず、収容する液剤の種類及び容量に応じて適宜設定される。
前記容器は、前記注出部の内部空間の壁面、及び前記蓋部において前記注出口と対向する壁面の少なくとも一方が、ポリブチレンテレフタレート(PBT)を含む樹脂によって構成される。ここで、「蓋部において前記注出口と対向する壁面」とは、蓋部を容器本体部及び/又は注出部に取りつけた際に注出口を覆う蓋部の内壁部分に該当する。具体的には、図2を例に挙げると、符号5で示した面部分が「注出部の内部空間の壁面」に該当し、符号6で示した面部分が「蓋部において前記注出口と対向する壁面」に相当する。
本発明のジブチルヒドロキシトルエンの安定化方法は、(A)ジブチルヒドロキシトルエンと、(B)プラノプロフェン及び/又はその薬学的に許容される塩を含有する液剤に、(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロールの誘導体よりなる群から選択される少なくとも1種を配合し、且つ当該液剤を、ジブチルヒドロキシトルエンを含有する製剤が、注出部の内部空間の壁面及び/又は蓋部において注出部の注出口と対向する壁面がポリブチレンテレフタレートを含む樹脂で構成された容器に収容することを特徴とする。
表2に示す液剤を調製して各種容器に収容して保存した際のジブチルヒドロキシトルエンの含有量の経時変化を測定した。具体的には、表2に示す液剤を常法に従って調製して、表1に示す各容器に収容し、密閉して40℃、75%RH、遮光条件にて2週間静置することにより保存した。その際、容器2及び3の場合には液剤の収容量は10mLにし、容器1の場合には液剤の収容量は5mLにした。また、容器2及び3の場合には、蓋部分が上面、容器本体部の底部が下面となるように、容器を正立させた状態で静置した。保存開始前、保存開始から1週間後及び2週間後に、容器中の液剤をノズルに接液しないようにサンプリングし、液剤中のジブチルヒドロキシトルエンの含有量をHPLCにて測定することにより、ジブチルヒドロキシトルエンの熱安定性を評価した。ジブチルヒドロキシトルエンの安定性は、具体的には、保存前のジブチルヒドロキシトルエン含有量に対する保存後のジブチルヒドロキシトルエン含有量の割合を残存率(%)として算出した。なお、容器3は従来汎用されている点眼容器の例である。また、ガラスは一般的な薬物が吸着し難いことが知られており、容器1はジブチルヒドロキシトルエンが吸着し難い容器の例である。
表3に示す液剤を常法に従って調製し、前記試験例1と同様の方法で、表1に示す各容器に収容して保存し、液剤中のジブチルヒドロキシトルエンの含有量をHPLCにて測定した。得られた測定値に基づいて、前記試験例1と同様の方法で、ジブチルヒドロキシトルエンの残存率(%)を算出した。
表4に示す液剤を常法に従って調製し、保存時の温度を50℃又は60℃に変更したこと以外は前記試験例1と同様の方法で、表1に示す各容器に収容して保存し、液剤中のジブチルヒドロキシトルエンの含有量をHPLCにて測定した。得られた測定値に基づいて、前記試験例1と同様の方法で、ジブチルヒドロキシトルエンの残存率(%)を算出した。
表5に示す液剤を常法に従って調製し、前記試験例1と同様の方法で、表1に示す各容器に収容して保存し、液剤中のジブチルヒドロキシトルエンの含有量をHPLCにて測定した。得られた測定値に基づいて、前記試験例1と同様の方法で、ジブチルヒドロキシトルエンの残存率(%)を算出した。
表6及び7に示す液剤を常法に従って調製し、前記試験例1と同様の方法で、表1に示す各容器に収容して保存し、液剤中のジブチルヒドロキシトルエンの含有量をHPLCにて測定した。得られた測定値に基づいて、前記試験例1と同様の方法で、ジブチルヒドロキシトルエンの残存率(%)を算出した。
表8に示す組成の点眼剤を常法に従って調製した。各点眼剤を、ポリエチレンテレフタレート製の容器本体部に、ポリブチレンテレフタレート製ノズルを装着した点眼剤容器に収容した。
2 注出部
3 蓋部
4 抽出部の内部空間
5 抽出部の内部空間の壁面
6 蓋部において注出部の注出口と対向する壁面
Claims (16)
- (A)ジブチルヒドロキシトルエンと、
(B)プラノプロフェン及び/又はその薬学的に許容される塩と、
(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロール誘導体よりなる群から選択される少なくとも1種と、
を含有する液剤が、容器に収容されてなるジブチルヒドロキシトルエン含有製品であって、
前記容器が、前記液剤を収容する容器本体部と、前記容器本体部に収容された液剤を注出する注出口を有する注出部と、前記注出口をふさぐ蓋部とを備え、
前記注出部の内部空間の壁面、及び前記蓋部において前記注出口と対向する壁面の少なくとも一方が、ポリブチレンテレフタレートを含む樹脂で構成されていることを特徴とする、
ジブチルヒドロキシトルエン含有製品。 - 前記液剤が、更にタウリンを含有する、請求項1に記載のジブチルヒドロキシトルエン含有製品。
- 前記注出部が、前記液剤を液滴状で注出するノズルであり、当該ノズルの内部空間の壁面がポリブチレンテレフタレートを含む樹脂で構成されている、請求項1又は2に記載のジブチルヒドロキシトルエン含有製品。
- 前記容器本体部が、ポリエチレンテレフタレートを含む樹脂で構成されている、請求項1〜3のいずれかに記載のジブチルヒドロキシトルエン含有製品。
- 前記液剤が、更にホウ酸緩衝剤を含む、請求項1〜4のいずれかに記載のジブチルヒドロキシトルエン含有製品。
- 前記(C)成分として、コンドロイチン硫酸エステル及び/又はその薬学的に許容される塩と、アスパラギン酸及び/又はその薬学的に許容される塩とを含む、請求項1〜5のいずれかに記載のジブチルヒドロキシトルエン含有製品。
- 前記液剤において、前記(A)成分が0.00001〜0.005w/v%、前記(B)成分が0.005〜0.5w/v%、及び前記(C)成分が0.0005〜5w/v%含まれる、請求項1〜6のいずれかに記載のジブチルヒドロキシトルエン含有製品。
- 前記液剤が点眼剤である、請求項1〜7のいずれかに記載のジブチルヒドロキシトルエン含有製品。
- (A)ジブチルヒドロキシトルエンと、
(B)プラノプロフェン及び/又はその薬学的に許容される塩と、
を含有する液剤におけるジブチルヒドロキシトルエンの安定化方法であって、
前記液剤に、(C)コンドロイチン硫酸エステル、アスパラギン酸、アルギン酸、アルギン酸の誘導体、それらの薬学的に許容される塩、シアノコバラミン、パンテノール、トコフェロール、及びトコフェロール誘導体よりなる群から選択される少なくとも1種を配合し、且つ
液剤を収容する容器本体部と、前記容器本体部に収容された液剤を注出する注出口を有する注出部と、前記注出口をふさぐ蓋部とを備え、前記注出部の内部空間の壁面、及び前記蓋部において前記注出口と対向する壁面の少なくとも一方がポリブチレンテレフタレートを含む樹脂で構成されている容器に、前記液剤を収容することを特徴とする、
安定化方法。 - 前記液剤に、更にタウリンを配合する、請求項9に記載の安定化方法。
- 前記注出部が、前記液剤を液滴状で注出するノズルであり、当該ノズルの内部空間の壁面がポリブチレンテレフタレートを含む樹脂で構成されている、請求項9又は10に記載の安定化方法。
- 前記容器本体部が、ポリエチレンテレフタレートを含む樹脂で構成されている、請求項9〜11のいずれかに記載の安定化方法。
- 前記液剤が、更にホウ酸緩衝剤を含む、請求項9〜12のいずれかに記載の安定化方法。
- 前記(C)成分として、コンドロイチン硫酸エステル及び/又はその薬学的に許容される塩と、アスパラギン酸及び/又はその薬学的に許容される塩とを含む、請求項9〜13のいずれかに記載の安定化方法。
- 前記液剤において、前記(A)成分が0.00001〜0.005w/v%、前記(B)成分が0.005〜0.5w/v%、及び前記(C)成分が0.0005〜5w/v%含まれる、請求項9〜14のいずれかに記載の安定化方法。
- 前記液剤が点眼剤である、請求項9〜15のいずれかに記載の安定化方法。
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WO2015190483A1 (ja) * | 2014-06-10 | 2015-12-17 | ロート製薬株式会社 | 眼科用水性組成物 |
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TW201540292A (zh) * | 2014-03-10 | 2015-11-01 | Senju Pharma Co | 二丁基羥基甲苯的穩定化方法(二) |
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RU2016139410A3 (ja) | 2018-09-18 |
WO2015137327A1 (ja) | 2015-09-17 |
RU2712031C2 (ru) | 2020-01-24 |
JP6509812B2 (ja) | 2019-05-08 |
JP2019135245A (ja) | 2019-08-15 |
TW201540292A (zh) | 2015-11-01 |
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