CA2660814C - Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate - Google Patents

Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate Download PDF

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Publication number
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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CA
Canada
Prior art keywords
diethylaminoethyl
compound
acoh
methyl
negative ion
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CA2660814A
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English (en)
French (fr)
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CA2660814A1 (en
Inventor
Chongxi Yu
Lina Xu
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Techfields Biochem Co Ltd
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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)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pulmonology (AREA)
  • Hospice & Palliative Care (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Immunology (AREA)
  • Otolaryngology (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrrole Compounds (AREA)
CA2660814A 2006-08-15 2006-08-15 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate Active CA2660814C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2006/052815 WO2008020270A1 (en) 2006-08-15 2006-08-15 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate

Publications (2)

Publication Number Publication Date
CA2660814A1 CA2660814A1 (en) 2008-02-21
CA2660814C true CA2660814C (en) 2017-07-18

Family

ID=39081992

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2660814A Active CA2660814C (en) 2006-08-15 2006-08-15 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate

Country Status (7)

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

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CA2657636C (en) * 2006-07-18 2021-11-09 Techfields Biochem Co. Ltd Positively charged water soluble prodrugs of ibuprofen with very fast skin penetration rate
EP2084124B9 (en) 2006-10-02 2015-07-01 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin penetration rates
WO2008056207A1 (en) 2006-11-08 2008-05-15 Chongxi Yu Transdermal delivery systems of peptides and related compounds
ES2633020T3 (es) 2006-12-10 2017-09-18 Yu, Chongxi-Techfields Biochem Sistemas de administración transdérmica de antibióticos betalactámicos
CN107652212B (zh) 2007-01-15 2019-11-15 于崇曦 维生素a酸类和类维生素a酸化合物的前药
EP2115140B8 (en) 2007-01-31 2017-01-25 Chongxi Yu Positively charged water-soluble prodrugs of 1H-imidazo[4,5-c]quinolin-4-amines and related compounds with very high skin penetration rates
KR101853971B1 (ko) 2007-06-04 2018-05-02 테크필즈 인크 매우 높은 피부 및 막 침투율을 가지는 비스테로이드성 소염제(ｎｓａｉａ) 약물전구체 및 이들의 새로운 의약적 용도
CA2745206C (en) * 2008-12-04 2018-09-18 Chongxi Yu High penetration compositions and their applications
KR20180110187A (ko) 2009-05-08 2018-10-08 테크필즈 바이오켐 코., 엘티디. 펩티드 및 펩티드­관련 화합물의 고침투성 전구약물 조성물
US9969751B2 (en) 2009-06-10 2018-05-15 Techfields Pharma Co., Ltd. High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds
IN2014KN02583A (zh) 2012-05-16 2015-05-08 Techfields Pharma Co Ltd
WO2014139161A1 (en) 2013-03-15 2014-09-18 Techfields Pharma Co., Ltd. Novel high penetration drugs and their compositions thereof for treatment of parkinson diseases
JP5940036B2 (ja) * 2013-10-08 2016-06-29 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
JP2017538678A (ja) 2014-11-05 2017-12-28 フレクサス・バイオサイエンシーズ・インコーポレイテッドＦｌｅｘｕｓ Ｂｉｏｓｃｉｅｎｃｅｓ， Ｉｎｃ． 免疫調節剤
US9862698B2 (en) 2014-12-16 2018-01-09 Adt Pharmaceuticals, Inc. Indenyl compounds, pharmaceutical compositions, and medical uses thereof
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
WO2019210223A1 (en) 2018-04-26 2019-10-31 Adt Pharmaceuticals, Llc Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses
US20220274911A1 (en) * 2020-09-09 2022-09-01 Nanjing Heron Pharmaceutical Science And Technology Co., Ltd. Arylpropionic acid derivative, pharmaceutical composition and preparation method and application thereof
WO2023279995A1 (zh) * 2021-07-06 2023-01-12 石家庄迪斯凯威医药科技有限公司 一类抗膀胱癌的季胺盐化合物及其应用
WO2023046078A1 (zh) * 2021-09-24 2023-03-30 石家庄迪斯凯威医药科技有限公司 一种新型普拉洛芬衍生物及其药物组合物和用途

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CA1012159A (en) * 1972-06-27 1977-06-14 Michael Marx Dialkylaminoalkyl esters of 2-(6-methoxy-2-naphthyl) propionic acid and the pharmaceutically acceptable salts thereof
US3896145A (en) * 1972-07-24 1975-07-22 Hoffmann La Roche Carbazoles
ZA738203B (en) * 1972-10-24 1975-05-28 Janssen Pharmaceutica Nv Aroyl-substituted phenylacetic acid derivatives
JPS5826744B2 (ja) * 1975-12-24 1983-06-04 ヒサミツセイヤク カブシキガイシヤ シンキナプロピオンサン エステルユウドウタイノセイゾウホウ
IT1090782B (it) * 1977-11-30 1985-06-26 Menarini Sas 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi
JPS58126846A (ja) * 1982-01-22 1983-07-28 Kaken Pharmaceut Co Ltd プロピオン酸アミノアルキルエステル誘導体、その製法およびそれを有効成分とする消炎、鎮痛剤
ZA882957B (en) * 1987-04-27 1989-12-27 Syntex Pharma Int Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs
IT1317826B1 (it) * 2000-02-11 2003-07-15 Dompe Spa Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8.
ITMI20010395A1 (it) * 2001-02-27 2002-08-27 Dompe Spa Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate
ITMI20012025A1 (it) * 2001-09-28 2003-03-28 Dompe Spa Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono

Also Published As

Publication number Publication date
EP2054384A1 (en) 2009-05-06
CN101506161A (zh) 2009-08-12
WO2008020270A1 (en) 2008-02-21
CA2660814A1 (en) 2008-02-21
EP2054384A4 (en) 2010-11-03
JP5424880B2 (ja) 2014-02-26
HK1137425A1 (zh) 2010-07-30
AU2006347391B2 (en) 2013-03-07
CN101506161B (zh) 2013-11-13
AU2006347391A1 (en) 2008-02-21
JP2010500989A (ja) 2010-01-14

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