JP5466006B2 - 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ - Google Patents
非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ Download PDFInfo
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- 0 CCC(C)(C(*c1ccc(*C(N)=O)cc1)=O)N*(C)C Chemical compound CCC(C)(C(*c1ccc(*C(N)=O)cc1)=O)N*(C)C 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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Description
残念ながら、多くの副作用はアセトアミノフェン及び関連化合物の使用と関連し、人及び実験動物において、最も著しくは肝毒性であり、まれな場合では腎毒性である。アセトアミノフェンの急性過剰摂取は、結果的に、まれな場合での腎尿細管壊死及び低血糖同様、用量依存性で死に至る可能性がある肝臓壊死をもたらす。
表1.アセトアミノフェン及びアセトアミノサロールのプロドラッグによるライジング抑制率
本結果は、プロドラッグは優れた鎮痛活性を表すということを示す。式(1)で表される他の化合物は類似した鎮痛活性を示す。
表2.アセトアミノフェン及びアセトアミノサロールのプロドラッグの解熱活性
本結果から、プロドラッグは100mg/kg用量において強い解熱活性を示したということが分かる。式(1)表される他の化合物は類似した解熱活性を示す。
N−アセチル−4−アミノフェニル ジメチルアミノブチラート塩酸塩の調製
アセトアミノフェン15.1g(0.1mol)をアセトン200ml及び10%NaHCO3200ml中に溶解した。ジメチルアミノブチリルクロリド塩酸塩18.6g(0.1mol)を混合物に加え、室温で3時間撹拌した。溶液を蒸発させた。酢酸エチル500mlを反応混合物に加え、混合物を5%NaHCO3(1×200ml)及び水(3×100ml)で洗浄した。得られた有機溶液を無水硫酸ナトリウム上で乾燥させた。硫酸ナトリウムを濾過により除去した。HClガスを溶液中にバブルする。固形生成物を濾過により集めた。乾燥後、目的生成物26g(86.4%)を得た。吸湿性生成物、水中での溶解性:400mg/ml、元素分析:C14H21ClN2O3、分子量:300.78、計算% C:55.90; H: 7.04; Cl: 11.79; N: 9.31; O: 15.96、実測% C: 55.96; H: 7.06; Cl: 11.76; N: 9.29; O: 15.93、1H-NMR(400MHz,D2O):δ: 1.98 (s, 3H), 2.01 (m, 2H), 2.21 (m, 2H), 2.90 (s, 6H), 3.24 (m, 2H), 7.05 (m, 2H), 7.60 (m, 2H), 7.80 (b, 1H)。
N−アセチル−4−アミノフェニル ジエチルアミノブチラート塩酸塩の調製
アセトアミノフェン15.1g(0.1mol)及びジエチルアミノ酪酸16g(0.1mol)をジクロロメチレン300mlに溶解した。混合物を氷浴で0℃に冷却する。N,N’−ジシクロヘキシルカルボジイミド20.6g(0.1mol)を反応混合物に添加した。混合物を0℃で1時間、及び室温で2時間撹拌した。固形物を濾過により除去する。ジクロロメチレン溶液を5%NaHCO3(2×100ml)及び水(3×100ml)で洗浄した。得られた有機溶液を無水硫酸ナトリウム上で乾燥させた。硫酸ナトリウムを濾過により除去した。酢酸6gを撹拌しながら反応混合物に加えた。固形生成物を濾過により集めた。乾燥後、目的生成物27g(82.1%)を得た。吸湿性生成物、水中での溶解性:400mg/ml、元素分析:C16H25ClN2O3、分子量:328.83、計算% C:58.44; H: 7.66; Cl: 10.78; N: 8.52; O: 14.60、実測% C: 58.40; H: 7.68; Cl: 10.76; N: 8.55; O: 14.61、1H-NMR(400MHz,D2O)δ: 1.50 (t, 6H), 2.00 (m, 2H), 2.02 (s, 3H), 2.21 (m, 2H), 3.24 (m, 2H), 3.27 (m, 4H), 7.05 (m, 2H), 7.60 (m, 2H), 7.80 (b, 1H)。
アセトアミノサロール27.1g(0.1mol)をアセトン200ml及び10%NaHCO3200ml中に溶解した。ジメチルアミノブチリルクロリド塩酸塩18.6g(0.1mol)を混合物に加え、室温で3時間撹拌した。溶液を蒸発させた。酢酸エチル500mlを反応混合物に加え、混合物を5%NaHCO3(1×200ml)及び水(3×100ml)で洗浄した。得られた有機溶液を無水硫酸ナトリウム上で乾燥させた。硫酸ナトリウムを濾過により除去した。HClガスを溶液中にバブルする。固形生成物を濾過により集めた。乾燥後、目的生成物36g(85.5%)を得た。吸湿性生成物、水中での溶解性:400mg/ml、元素分析:C21H25ClN2O5、分子量:420.89、計算% C: 59.93; H: 5.99; Cl: 8.42; N: 6.66; O: 19.01、実測% C: 59.96; H: 6.02; Cl: 8.40; N: 6.64; O: 18.98、1H-NMR(400MHz,D2O):δ: 1.99 (s, 3H), 2.01 (m, 2H), 2.21 (m, 2H), 2.90 (s, 6H), 3.24 (m, 2H), 7.13 (m, 2H), 7.22 (m, 2H), 7.47 (m, 1H), 7.60 (m, 2H), 7.80 (b, 1H), 8.10 (m, 1H)。
アセトアミノサロール27.1g(0.1mol)及びジエチルアミノ酪酸16g(0.1mol)をジクロロメチレン300mlに溶解した。混合物を氷浴で0℃に冷却する。N,N’−ジシクロヘキシルカルボジイミド20.6g(0.1mol)を反応混合物に添加した。混合物を0℃で1時間、及び室温で2時間撹拌した。固形物を濾過により除去する。ジクロロメチレン溶液を5%NaHCO3(2×100ml)及び水(3×100ml)で洗浄した。得られた有機溶液を無水硫酸ナトリウム上で乾燥させた。硫酸ナトリウムを濾過により除去した。酢酸6gを撹拌しながら反応混合物に加えた。固形生成物を濾過により集めた。乾燥後、目的生成物39g(86.9%)を得た。吸湿性生成物、水中での溶解性:400mg/ml、元素分析:C23H29ClN2O5、分子量:448.94、計算% C: 61.53; H: 6.51; Cl: 7.90; N: 6.24; O: 17.82、実測% C: 61.50; H: 6.56; Cl: 7.85; N: 6.22; O: 17.87、1H-NMR(400MHz,D2O)δ: 1.50 (t, 6H), 2.00 (m, 2H), 2.02 (s, 3H), 2.21 (m, 2H), 3.24 (m, 2H), 3.27 (m, 4H), 7.11 (m, 2H), 7.21 (m, 2H), 7.47 (m, 1H), 7.65 (m, 2H), 7.80 (b, 1H), 8.10 (m, 1H)。
Claims (12)
- 前記非ステロイド性抗炎症薬治療可能な状態が、歯痛、頭痛、炎症性疼痛、熱、月経困難症、糖尿病性神経障害、急性片頭痛、血友病性関節症、骨喪失、並びに日焼けからなる群から選択される、請求項1に記載の医薬組成物。
- 身体の一部に溶液、スプレー、ローション、軟膏、エマルジョン又はゲルの形態で経皮投与される、請求項1又は2に記載の医薬組成物。
- 前記疼痛が、頭痛、歯痛、筋肉痛、又は炎症性疼痛である、請求項4に記載の医薬組成物。
- 溶液、スプレー、ローション、軟膏、エマルジョン又はゲルの形態で経皮投与される、請求項6に記載の医薬組成物。
- 前記耳の炎症性及び/又は有痛性状態が、耳炎である、請求項8に記載の医薬組成物。
- 包帯又はパッチである、請求項10に記載の経皮治療製剤。
- 活性物質貯蔵庫であり、皮膚に面する透過性底面を有する、請求項10に記載の経皮治療製剤。
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JP2016006124A (ja) * | 2015-10-01 | 2016-01-14 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ |
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2006
- 2006-09-03 JP JP2009526183A patent/JP5466006B2/ja not_active Expired - Fee Related
- 2006-09-03 WO PCT/IB2006/053091 patent/WO2008029200A1/en active Application Filing
- 2006-09-03 EP EP06795894.2A patent/EP2061749B1/en not_active Not-in-force
- 2006-09-03 CN CN2006800557470A patent/CN101506143B/zh active Active
- 2006-09-03 ES ES06795894.2T patent/ES2670407T3/es active Active
- 2006-09-03 EP EP14153622.7A patent/EP2746251A3/en active Pending
- 2006-09-03 EP EP18157598.6A patent/EP3388417A1/en active Pending
- 2006-09-03 CA CA2661649A patent/CA2661649C/en active Active
- 2006-09-03 PL PL06795894T patent/PL2061749T3/pl unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013173777A (ja) * | 2013-04-30 | 2013-09-05 | Techfields Biochem Co Ltd | 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ |
JP2016006124A (ja) * | 2015-10-01 | 2016-01-14 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ |
Also Published As
Publication number | Publication date |
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CA2661649C (en) | 2014-12-30 |
EP2746251A2 (en) | 2014-06-25 |
EP2061749A4 (en) | 2010-12-29 |
EP2746251A3 (en) | 2014-07-02 |
JP2010502583A (ja) | 2010-01-28 |
EP2061749B1 (en) | 2018-02-21 |
CA2661649A1 (en) | 2008-03-13 |
CN101506143B (zh) | 2013-06-05 |
WO2008029200A1 (en) | 2008-03-13 |
ES2670407T3 (es) | 2018-05-30 |
EP3388417A1 (en) | 2018-10-17 |
CN101506143A (zh) | 2009-08-12 |
PL2061749T3 (pl) | 2018-11-30 |
EP2061749A1 (en) | 2009-05-27 |
AU2006347925A1 (en) | 2008-03-13 |
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