CA2660814C - Promedicaments hydrosolubles charges positivement contenant des acides aryl- et heteroarylpropioniques et dotes d'une tres grande vitesse de penetration cutanee - Google Patents

Promedicaments hydrosolubles charges positivement contenant des acides aryl- et heteroarylpropioniques et dotes d'une tres grande vitesse de penetration cutanee Download PDF

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CA2660814C
CA2660814C CA2660814A CA2660814A CA2660814C CA 2660814 C CA2660814 C CA 2660814C CA 2660814 A CA2660814 A CA 2660814A CA 2660814 A CA2660814 A CA 2660814A CA 2660814 C CA2660814 C CA 2660814C
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diethylaminoethyl
compound
acoh
methyl
negative ion
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CA2660814A1 (fr
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Chongxi Yu
Lina Xu
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Techfields Biochem Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • 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
    • 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
    • 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
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Otolaryngology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

De nouveaux promédicaments chargés positivement contenant des acides aryl- et hétéroarylpropioniques représentés par la formule générale (1) "Structure 1" et par la formule générale (2) "Structure 2" ont été mis au point et synthétisés. Les composés représentés par la formule générale (1) "Structure 1" et par la formule générale (2) "Structure 2" indiquées ci-dessus peuvent être préparés à partir de dérivés fonctionnels de naproxène, suprofène, acide .alpha.-méthyl-(p-chlorobenzoyl)-5-méthoxy-2-méthylindole 3-acétique, flurbiprofène, carprofène, pranoprofène, benoxaprofène, alminoprofène, acide tiaprofénique, pirprofène, zaltoprofène, bermoprofène, loxoprofène, indoprofène, fenclorac, oxaprozine, fenbufène, orpanoxine, kétorolac, clidanac et les composés apparentés, (par exemple les halogénures d'acides ou les anhydrides mixtes), par réaction avec des alcools, thiols, ou amines appropriés. Ces promédicaments renferment des groupes amino à charge positive qui non seulement augmentent de façon importante la solubilité de ces médicaments, mais encore se lient à la charge négative sur le groupe de tête phosphate de membrane et poussent le promédicament dans le cytosol. Les résultats suggèrent que les promédicaments se diffusent à travers la peau humaine de 100-130 fois plus vite que leurs médicaments parents. Pris par la voie orale, les naproxène, suprofène, acide .alpha.-méthyl-(p-chlorobenzoyl)-5-méthoxy-2-méthylindole 3-acétique, flurbiprofène, carprofène, pranoprofène, benoxaprofène, alminoprofène, acide tiaprofénique, pirprofène, zaltoprofène, bermoprofène, loxoprofène, indoprofène, fenclorac, oxaprozine, fenbufène, orpanoxine, kétorolac, clidanac, et composés apparentés atteignent le taux de plasma de pic en 2-4 heures. Pris par la voie transdermique, les promédicaments ne prennent qu'environ 40-50 minutes pour atteindre le taux de plasma de pic. Dans le plasma, plus de 90% desdits promédicaments peuvent reprendre leur forme de médicament en quelques minutes. Les promédicaments peuvent être utilisés médicalement pour traiter n'importe quelles conditions répondant à un traitement par analgésiques anti-inflammatoires non stéroïdiens NSAIA chez l'homme ou chez l'animal. Les promédicaments peuvent être administrés par voie orale autant que par voie transdermique dans toute thérapeutique et permettetn d'éviter la plupart des effets secondaires des NSAIA, plus particulièrement les troubles gastro-intestinaux tels que la dyspepsie, les saignements gastro-duodénaux, les ulcères gastriques et la gastrite. Les systèmes d'administration transdermique contrôlée des promédicaments permettent aux naproxène, suprofène, acide .alpha.-méthyl-(p-chlorobenzoyl)-5-méthoxy-2-methylindole 3-acétique, flurbiprofène, carprofène, pranoprofène, benoxaprofène, alminoprofène, acide tiaprofénique, pirprofène, zaltoprofène, bermoprofène, loxoprofène, indoprofène, fenclorac, oxaprozine, fenbufène, orpanoxine, kétorolac, clidanac et composés apparentés d'atteindre des taux thérapeutiques sanguins constants permettant d'optimiser l'efficacité et de réduire les effets secondaires des NSAIA. En outre, l'administration transdermique desdits promédicaments permet d'administrer la médication beaucoup plus facilement, notamment aux enfants.
CA2660814A 2006-08-15 2006-08-15 Promedicaments hydrosolubles charges positivement contenant des acides aryl- et heteroarylpropioniques et dotes d'une tres grande vitesse de penetration cutanee Active CA2660814C (fr)

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Application Number Priority Date Filing Date Title
PCT/IB2006/052815 WO2008020270A1 (fr) 2006-08-15 2006-08-15 Promédicaments hydrosolubles chargés positivement contenant des acides aryl- et hétéroarylpropioniques et dotés d'une très grande vitesse de pénétration cutanée

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CA2660814A1 CA2660814A1 (fr) 2008-02-21
CA2660814C true CA2660814C (fr) 2017-07-18

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EP (1) EP2054384A4 (fr)
JP (1) JP5424880B2 (fr)
CN (1) CN101506161B (fr)
AU (1) AU2006347391B2 (fr)
CA (1) CA2660814C (fr)
HK (1) HK1137425A1 (fr)
WO (1) WO2008020270A1 (fr)

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US20090221703A1 (en) 2006-07-09 2009-09-03 Chongxi Yu High penetration composition and uses thereof
US20090238763A1 (en) 2006-07-09 2009-09-24 Chongxi Yu High penetration compositions and uses thereof
EP3210964A1 (fr) * 2006-07-18 2017-08-30 Techfields Biochem Co. Ltd Pro-médicaments d'ibuprofène hydrosolubles positivement chargés à taux de pénétration cutanée très rapide
EP2084124B9 (fr) 2006-10-02 2015-07-01 Techfields Biochem Co. Ltd Promédicaments hydrosolubles de prostaglandines et composés analogues, positivement chargés, à taux de pénétration cutanée très élevé
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ES2633020T3 (es) 2006-12-10 2017-09-18 Yu, Chongxi-Techfields Biochem Sistemas de administración transdérmica de antibióticos betalactámicos
JP5826459B2 (ja) 2007-01-15 2015-12-02 チョンシー ユー 非常に高い皮膚浸透率を有するレチノイド及びレチノイド様化合物の正に荷電した水溶性プロドラッグ
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KR20180049144A (ko) * 2007-06-04 2018-05-10 테크필즈 인크 매우 높은 피부 및 막 침투율을 가지는 비스테로이드성 소염제(ｎｓａｉａ) 약물전구체 및 이들의 새로운 의약적 용도
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US20160168108A1 (en) 2014-12-16 2016-06-16 Adt Pharmaceuticals, Inc. Method of treating or preventing ras-mediated diseases
JP6290947B2 (ja) * 2016-02-05 2018-03-07 テックフィールズ バイオケム カンパニー リミテッド 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
CA3096700C (fr) 2018-04-26 2023-08-22 Adt Pharmaceuticals, Llc Indenes, indanes, azaindenes, azaindanes anticancereux, compositions pharmaceutiques et utilisations
KR20220035334A (ko) * 2020-09-09 2022-03-22 난징 헤론 파마슈티컬 사이언스 앤 테크놀로지 컴퍼니 리미티드 아릴프로피온산 유도체, 약학적 조성물 및 이의 제조방법과 응용
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AU2006347391A1 (en) 2008-02-21
JP2010500989A (ja) 2010-01-14
CA2660814A1 (fr) 2008-02-21
CN101506161A (zh) 2009-08-12
WO2008020270A1 (fr) 2008-02-21
JP5424880B2 (ja) 2014-02-26
HK1137425A1 (en) 2010-07-30
EP2054384A4 (fr) 2010-11-03
AU2006347391B2 (en) 2013-03-07
EP2054384A1 (fr) 2009-05-06
CN101506161B (zh) 2013-11-13

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