JP2021525748A - バイオベース医薬及び患者コンプライアンスを向上させる方法 - Google Patents
バイオベース医薬及び患者コンプライアンスを向上させる方法 Download PDFInfo
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- JP2021525748A JP2021525748A JP2020566784A JP2020566784A JP2021525748A JP 2021525748 A JP2021525748 A JP 2021525748A JP 2020566784 A JP2020566784 A JP 2020566784A JP 2020566784 A JP2020566784 A JP 2020566784A JP 2021525748 A JP2021525748 A JP 2021525748A
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Abstract
Description
本出願は、2018年5月28日に出願された米国仮特許出願第62/677,161号に対する優先権の利益を主張するものである。
芳香族化合物−本明細書中で使用する場合、「芳香族化合物(aromatics)」または「芳香族化合物(aromatic compound)」という用語は、例えば単環式芳香環系(例えば、ベンジル、フェニルなど)及び縮合多環式芳香環系(例えば、ナフチル、1,2,3,4−テトラヒドロナフチルなど)などの1つ以上の芳香族基を含む1つまたは複数の炭化水素化合物を指して使用される。芳香族化合物の例としては、限定されないが、ベンゼン、トルエン、インダン、インデン、2−エチルトルエン、3−エチルトルエン、4−エチルトルエン、トリメチルベンゼン(例えば、1,3,5−トリメチルベンゼン、1,2,4−トリメチルベンゼン、1,2,3−トリメチルベンゼンなど)、エチルベンゼン、スチレン、クメン、メチルベンゼン、プロピルベンゼン、キシレン(例えば、p−キシレン、m−キシレン、o−キシレン)、ナフタレン、メチルナフタレン(例えば、1−メチルナフタレン)、アントラセン、9,10−ジメチルアントラセン、ピレン、フェナントレン、ジメチルナフタレン(例えば、1,5−ジメチルナフタレン、1,6−ジメチルナフタレン、2,5−ジメチルナフタレンなど)、エチルナフタレン、ヒドリンデン、メチルヒドリンデン及びジメチルヒドリンデンが挙げられる。いくつかの実施形態では、単環式の、及び/またはより高度な環式の芳香族化合物も製造され得る。芳香族化合物には、ヘテロ原子置換基を含有する単環式及び多環式化合物、すなわち、フェノール、クレゾール、ベンゾフラン、アニリン、インドールなども含まれる。
セチリジンの上記合成から、いくつかの望ましい実施形態において本発明によって炭素原子の12/20(アリール基中の炭素)または13/20の炭素原子(第三級炭素を含む)がバイオベースとなったセチリジンが提供されることが容易に分かる。より高い割合は、非芳香族のバイオベース化合物の使用によって提供され得る。
スキーム2。セチリジン二塩酸塩(Cetrizine dihydrochloride)を得るための塩化4−クロロベンジルによる手法
スキーム3。セチリジン中間体を得るための経路
Org &Biomolecular Chem,2017,15,4984−91)
ベンゼンからの中間体4−クロロアニリン:
スキーム1。(CN104788326A)
ステップ1:Gerald Booth(2007).“Nitro Compounds,Aromatic”.Ullmann’s Encyclopedia of Industrial Chemistry.Weinheim:Wiley−VCH。
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スキーム1。Kottler et al.米国特許第2,764,590号 Certain 4,4’−disubstituted−diphenylpyridyl methanes and process。
トルエンからの中間体フェノール
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スキーム2。
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中間体:
ベンゼンからの2,6−ジクロロアニリン
スキーム2。
ステップ1:U.Beck,E.Loser,“Chlorinated Benzenes and other Nucleus−Chlorinated Aromatic Hydrocarbons”Ullmann’s Encyclopedia of Industrial Chemistry,2012,Wiley−VCH,Weinheim。
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トルエンからの中間体2−クロロベンゾトリクロリド
スキーム2。
ステップ1:Justus Liebigs Annalen der Chemie,Vol.146,p.322−331
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(Z)−3−アミノ−2−メチル−2−ブテン酸エチルエステル及びメチルマロン酸ジエチルからの4−メトキシ−2,3,5−トリメチルピリジン。
スキーム2。
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スキーム3。
ベンゼンからの5−メトキシ−2−ベンズイミダゾリルスルフィン酸(−)−メンチル
ステップ1:Justus Liebigs Annalen der Chemie,Vol.164,p.162,176。
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スキーム1:Quasdorf,Kyle W.et al.Journal of the American Chemical Society,2009,Vol.131,No.49 p.17748−17749。
ベンゼンからの中間体フェニルボロン酸:
スキーム2。
ステップ1:Justus Liebigs Annalen der Chemie,Vol.164,p.162,176。
ステップ2:Robertson,D.L.(2007−01−03).“Grignard Synthesis:Synthesis of Benzoic Acid and of Triphenylmethanol”
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スキーム2。
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ステップ5:Chemical Communications,Vol.46,No.10,p.1697−
スキーム1。
−ベンゼンから
ステップ1:Justus Liebigs Annalen der Chemie,Vol.164,p.162,176。
ステップ2〜4:Nilesh et al.,World J.Pharm.Sci.2016,4(3),478−481,“An efficient and safe process for synthesis of doxylamine succinate”。−pdf添付あり
スキーム1.Chen,Zhengming et al.Bioorganic and Medicinal Chemistry Letters,Vol.14,No.21 p.5275−5279。
イオペラミドの合成から、いくつかの望ましい実施形態において本発明によって炭素原子の18/29(アリール基由来)が、またはバイオベース試薬を使用することで16/29もしくは(バイオベースの酢酸エチルを含む)22/29もしくはそれより多くがバイオベースとなったイオペラミドが提供されることが分かる。
スキーム2。
ステップ1:Justus Liebigs Annalen der Chemie,Vol.164,p.162,17。
ステップ2:Song,Bingrui et al.Advanced Synthesis and Catalysis,2011,Vol.353,No.10 p.1688−1694
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101名の英国(UK)居住者、106名のドイツ(DE)居住者及び63名のスウェーデン(SE)居住者について調査を実施したが、彼らは全員、セチリジンを使用する。この調査では人々にセチリジンについての一連の質問をした。図1で分かるように、セチリジン中の植物材料の百分率が高ければ高いほど、より多くの人々をバイオベース医薬の購入に導くことになった。また、調査において人々に「あなたは、自分の薬が環境に優しい再生可能な植物原料から製造されたものである場合、その薬を飲み続けることを完遂する可能性が、標準的材料/合成化学薬品から作られた同じ薬に比べてより高いと思いますか。1を可能性がかなり低いとし、5を可能性がかなり高いとして、1〜5の等級で評価して下さい。」という質問もした。非常に驚くべきことに、この質問から、48〜67%の人々において薬の服用を遵守することの可能性がやや高くなり、または可能性がかなり高くなり、バイオベースのセチリジンがコンプライアンス(アドヒアランス)を向上させるであろうことが発見された。これらの結果を図2に示す。
Claims (31)
- 疾患状態を治療する方法であって、
それを必要とする患者に、植物材料に由来し少なくとも50質量%のバイオベース炭素を含むセチリジンを薬学的に有効な量で投与すること
を含む、前記方法。 - セチリジン中の20個の炭素原子のうちの12個または13個がバイオベースである、請求項1に記載の方法。
- 前記セチリジンが、投薬計画において少なくとも5日を掛けて複数回用量で投与され、患者コンプライアンスが少なくとも20%向上する、請求項1または請求項2のいずれかに記載の方法。
- 20個の炭素原子のうちの少なくとも12個がバイオベースであるセチリジンを含む、医薬活性化合物。
- 疾患状態を治療する方法であって、
それを必要とする患者に、植物材料に由来し少なくとも50質量%のバイオベース炭素を含む化合物を薬学的に有効な量で投与すること
を含み、前記化合物が、クロルヘキシジン(クロルヘキサメド フォルテ)、アンブロキソール(ムコソルバン)、ビサコジル(Ducolax)、キシロメタゾリン(Olynth)、ジクロフェナク((フォルテ ボルタレン)、クロトリマゾール(カネステン)、オメプラゾール(omep Hexal)、フルルビプロフェン(Dobendan)、ナプロキセン(Dolormin)、ドキシラミン(Hoggar)、イオペラミド及びイブプロフェンである、前記方法。 - 少なくとも部分的にバイオマスに由来する、医薬活性化合物。
- 請求項6に記載の医薬活性化合物であって、
少なくとも1つの芳香族基を含み、
前記化合物の前記少なくとも1つの芳香族基がバイオマスに由来するものである、
前記医薬活性化合物。 - 前記化合物全体がバイオマスに由来する、請求項7に記載の医薬活性化合物。
- 生物の14C:12C同位体比に類似する14C:12C同位体比を有する医薬活性化合物。
- およそ1パーツ・パー・トリリオンの14C含有量を有する、表1の一覧から選択される医薬活性化合物。
- 前記化合物がランソプラゾールまたはメフェンテルミンである、請求項6に記載の化合物。
- アレルギー症候の治療のための、請求項1〜3のいずれかに記載の方法。
- 請求項6〜10のいずれかに記載の少なくとも1つの化合物を含む医薬組成物。
- 少なくとも1つの薬学的に許容される賦形剤をさらに含む、請求項13に記載の医薬組成物。
- 少なくとも2つの医薬活性化合物を含む、請求項13に記載の医薬組成物。
- 疾患状態を治療する方法であって、それを必要とする患者に請求項13に記載の組成物を投与することを含む、前記方法。
- 疾患状態を治療する方法であって、それを必要とする患者に請求項13に記載の組成物を投与することを含む、前記方法。
- 疾患状態を治療する方法であって、それを必要とする患者に請求項14に記載の組成物を投与することを含む、前記方法。
- 前記少なくとも1つの医薬活性化合物が少なくとも部分的にバイオマスに由来することを前記患者が知っている、請求項1〜3及び請求項16〜18のいずれかに記載の方法。
- 患者コンプライアンスが改善される、請求項19に記載の方法。
- 医薬品投薬計画の患者コンプライアンスを改善する方法であって、
前記投薬計画において少なくとも部分的にバイオマスに由来する医薬活性化合物を投与すること
を含む、前記方法。 - 前記投薬計画が、少なくとも3日を掛けて複数回用量を含む、請求項21に記載の方法。
- 医薬品投薬計画の患者コンプライアンスを改善するのに使用するためのX物質であって、クロルヘキシジン(クロルヘキサメド フォルテ)、アンブロキソール(ムコソルバン)、セチリジン(Hexal)、ビサコジル(Ducolax)、キシロメタゾリン(Olynth)、ジクロフェナク((フォルテ ボルタレン)、クロトリマゾール(カネステン)、オメプラゾール(omep Hexal)、フルルビプロフェン(Dobendan)、ナプロキセン(Dolormin)、ドキシラミン(Hoggar)、イオペラミド及びイブプロフェンのうちの1つであり、X物質が少なくとも10質量%のバイオベース炭素を含むものである、前記X物質。
- 10〜90質量%の炭素原子がバイオベースである、医薬活性化合物。
- 患者母集団における医薬活性化合物の代謝を評価する方法であって、
(i)少なくとも部分的にバイオマスに由来する医薬活性化合物を前記患者母集団中の患者に投与するステップ、及び
(ii)前記医薬活性化合物の少なくとも1つの代謝産物の同位体比を評価するステップ
を含む、前記方法。 - バイオマスベースの医薬活性化合物を作る方法であって、
バイオマスベースの芳香族化合物を他の有機分子と反応させて、少なくとも部分的にバイオマスベースである医薬活性分子を得ること
を含む、前記方法。 - 前記医薬活性化合物が、ランソプラゾール、セチリジンまたはメフェンテルミンである、請求項26に記載の方法。
- 前記化合物が、クロルヘキシジン、アンブロキソール、セチリジン、ビサコジル、キシロメタゾリン、ジクロフェナク、クロトリマゾール、オメプラゾール、フルルビプロフェン、ナプロキセン、ドキシラミン、イオペラミドまたはイブプロフェンである、請求項24に記載の医薬活性化合物。
- 部分的または完全にバイオベースである炭素原子を含有する化合物であって、
感染症を治療するためまたは代謝を追跡するためのクロルヘキシジン、呼吸器疾患を治療するためのアンブロキソール、アレルギー症候を治療するためのセチリジン、便秘を治療するためのビサコジル、鼻詰まりを治療するためのキシロメタゾリン、疼痛及び炎症性疾患を治療するためのジクロフェナク、真菌感染症を治療するためのクロトリマゾール、胃潰瘍及び胃酸の逆流を治療するためのオメプラゾール、疼痛及び関節炎を治療するためのフルルビプロフェン、発熱及び疼痛を治療するためのナプロキセン、アレルギー症候を治療するためのドキシラミン、下痢を治療するためのイオペラミド、ならびに発熱及び疼痛を治療するためのイブプロフェン
を含み、
前記医薬活性化合物が、少なくとも10質量%のバイオベース炭素、好ましくは少なくとも40%または少なくとも50%または少なくとも70%または100%のバイオベース炭素を含むものである、前記化合物。 - 前記化合物が、
22個の炭素のうちの12個がバイオベースであるクロルヘキシジン、
13個の炭素のうちの7個がバイオベースであるアンブロキソール、
22個の炭素のうちの12個もしくは16個がバイオベースであるビサコジル、
14個の炭素のうちの8個もしくは10個がバイオベースであるキシロメタゾリン、
14個の炭素のうちの13個がバイオベースであるジクロフェナク、
20個の炭素のうちの17個がバイオベースであるクロトリマゾール、
17個の炭素のうちの6個がバイオベースであるオメプラゾール、
15個の炭素のうちの6個もしくは12個がバイオベースであるフルルビプロフェン、
14個の炭素のうちの10個もしくは11個がバイオベースであるナプロキセン、
17個の炭素のうちの6個もしくは10個がバイオベースであるドキシラミン、または
29個の炭素のうちの16、18もしくは22個がバイオベースであるイオペラミド
である、請求項6に記載の化合物。 - 疾患状態を治療する方法であって、
それを必要とする患者に、炭素の少なくとも50%が植物に由来するイブプロフェンを薬学的に有効な量で投与すること
を含む、前記方法。
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- 2019-05-28 AU AU2019277154A patent/AU2019277154A1/en not_active Abandoned
- 2019-05-28 US US17/607,352 patent/US20220226310A1/en active Pending
- 2019-05-28 KR KR1020207034546A patent/KR20210015827A/ko unknown
- 2019-05-28 CA CA3099916A patent/CA3099916A1/en active Pending
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EP3801484A1 (en) | 2021-04-14 |
EP3801484A4 (en) | 2022-06-29 |
BR112020024205A2 (pt) | 2021-02-17 |
KR20210015827A (ko) | 2021-02-10 |
CN112384209A (zh) | 2021-02-19 |
WO2019231937A1 (en) | 2019-12-05 |
MX2020012728A (es) | 2021-04-28 |
AU2019277154A1 (en) | 2020-11-26 |
US20220226310A1 (en) | 2022-07-21 |
CA3099916A1 (en) | 2019-12-05 |
JP7480063B2 (ja) | 2024-05-09 |
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