EP2054384A4 - 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

Info

Publication number
EP2054384A4
EP2054384A4 EP06795662A EP06795662A EP2054384A4 EP 2054384 A4 EP2054384 A4 EP 2054384A4 EP 06795662 A EP06795662 A EP 06795662A EP 06795662 A EP06795662 A EP 06795662A EP 2054384 A4 EP2054384 A4 EP 2054384A4
Authority
EP
European Patent Office
Prior art keywords
aryl
positively charged
skin penetration
penetration rate
charged water
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.)
Pending
Application number
EP06795662A
Other languages
German (de)
French (fr)
Other versions
EP2054384A1 (en
Inventor
Chongxi Yu
Lina Xu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
YU, CHONGXI
Techfields Biochem Co Ltd
Original Assignee
Techfields Biochem Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Techfields Biochem Co Ltd filed Critical Techfields Biochem Co Ltd
Publication of EP2054384A1 publication Critical patent/EP2054384A1/en
Publication of EP2054384A4 publication Critical patent/EP2054384A4/en
Pending legal-status Critical Current

Links

Classifications

    • 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
EP06795662A 2006-08-15 2006-08-15 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate Pending EP2054384A4 (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
EP2054384A1 EP2054384A1 (en) 2009-05-06
EP2054384A4 true EP2054384A4 (en) 2010-11-03

Family

ID=39081992

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06795662A Pending EP2054384A4 (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 (en)
JP (1) JP5424880B2 (en)
CN (1) CN101506161B (en)
AU (1) AU2006347391B2 (en)
CA (1) CA2660814C (en)
HK (1) HK1137425A1 (en)
WO (1) WO2008020270A1 (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090238763A1 (en) 2006-07-09 2009-09-24 Chongxi Yu High penetration compositions and uses thereof
US20090221703A1 (en) 2006-07-09 2009-09-03 Chongxi Yu High penetration composition and uses thereof
PL2041068T3 (en) * 2006-07-18 2017-05-31 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of ibuprofen with very fast skin penetration rate
ES2466346T3 (en) 2006-10-02 2014-06-10 Techfields Biochem Co. Ltd Prodrugs of water soluble prostaglandins with positive charge and compounds related to very high skin penetration rates
AU2006350707A1 (en) 2006-11-08 2008-05-15 Chongxi Yu Transdermal delivery systems of peptides and related compounds
ES2633020T3 (en) 2006-12-10 2017-09-18 Yu, Chongxi-Techfields Biochem Systems for transdermal administration of beta-lactam antibiotics
EP3181132A1 (en) 2007-01-15 2017-06-21 Chongxi Yu Positively charged water-soluble prodrugs of retinoids and retinoid-like compounds with very high skin penetration rates
AU2007345952C1 (en) 2007-01-31 2017-06-08 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
RU2509076C2 (en) 2007-06-04 2014-03-10 Текфилдз Инк Prodrugs of nonsteroid anti-inflammatory agents (nsaia) with very high speed of penetration through skin and membranes, and new medical applications of above said prodrugs
BR122021011394B1 (en) * 2008-12-04 2021-09-28 Chongxi Yu HIGH PENETRATION COMPOSITION OF A MAIN DRUG, AND USE OF A HPC
RU2627065C2 (en) 2009-05-08 2017-08-03 Текфилдз Байокем Ко., Лтд. Prodrug compositions with high degree of penetration based on peptides and related compounds
US9969751B2 (en) 2009-06-10 2018-05-15 Techfields Pharma Co., Ltd. High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds
AU2013262320B2 (en) 2012-05-16 2018-02-22 Techfields Pharma Co., Ltd. High penetration prodrug compositions and pharmaceutical composition thereof for treatment of pulmonary conditions
JP2016516018A (en) 2013-03-15 2016-06-02 テックフィールズ ファーマ カンパニー リミテッド Novel high-permeability drug and its composition for treating Parkinson's disease
JP5940036B2 (en) * 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 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin permeability
EA201790806A1 (en) 2014-11-05 2017-11-30 Флексус Байосайенсиз, Инк. IMMUNOREGULATING AGENTS
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 (en) * 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 Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin permeability
US11186596B2 (en) 2018-04-26 2021-11-30 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
CN117916219A (en) * 2021-07-06 2024-04-19 石家庄迪斯凯威医药科技有限公司 Quaternary amine salt compound for resisting bladder cancer and application thereof
WO2023046078A1 (en) * 2021-09-24 2023-03-30 石家庄迪斯凯威医药科技有限公司 Novel pranoprofen derivative, and pharmaceutical composition and use thereof

Citations (4)

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GB1377316A (en) * 1972-06-27 1974-12-11 Syntex Corp Dialkylaminoalkyl esters of arylaliphatic acids and acid addition salts thereof
US3896145A (en) * 1972-07-24 1975-07-22 Hoffmann La Roche Carbazoles
GB1573322A (en) * 1975-12-24 1980-08-20 Hisamitsu Pharmaceutical Co Phenylactic acid ester derivatives
JPS58126846A (en) * 1982-01-22 1983-07-28 Kaken Pharmaceut Co Ltd Propionic acid aminoalkyl ester derivative, its preparation and antiphlogistic and analgesic agent containing said derivative as active component

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JPS6452742A (en) * 1987-04-27 1989-02-28 Syntex Pharma Int Omega-quaternary ammonium alkyl ester and thioester of acidic non-steroidal antiinflammatory
IT1317826B1 (en) * 2000-02-11 2003-07-15 Dompe Spa AMIDES, USEFUL IN THE INHIBITION OF THE CHEMOTAXIS OF NEUTROPHILES INDUCED BY IL-8.
ITMI20010395A1 (en) * 2001-02-27 2002-08-27 Dompe Spa OMEGA-AMINO ALKYLAMIDS OF R-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF CHEMOTAXIS OF POLYMORPHONUCLEATED AND MONONUCLEATE CELLS
ITMI20012025A1 (en) * 2001-09-28 2003-03-28 Dompe Spa QUATERNARY AMMONIUM SALTS OF OMEGA-AMINO ALKYLAMIDS OF R 2-ARY-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1377316A (en) * 1972-06-27 1974-12-11 Syntex Corp Dialkylaminoalkyl esters of arylaliphatic acids and acid addition salts thereof
US3896145A (en) * 1972-07-24 1975-07-22 Hoffmann La Roche Carbazoles
GB1573322A (en) * 1975-12-24 1980-08-20 Hisamitsu Pharmaceutical Co Phenylactic acid ester derivatives
JPS58126846A (en) * 1982-01-22 1983-07-28 Kaken Pharmaceut Co Ltd Propionic acid aminoalkyl ester derivative, its preparation and antiphlogistic and analgesic agent containing said derivative as active component

Non-Patent Citations (5)

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Title
JARKKO RAUTIO ET AL: "Piperazinylalkyl prodrugs of naproxen improve in vitro skin permeation", EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 11, no. 2, 1 August 2000 (2000-08-01), pages 157 - 163, XP055049945, ISSN: 0928-0987, DOI: 10.1016/S0928-0987(00)00090-7 *
KAGAKU: "JPS58126846A -PROPIONIC ACID AMINOALKYL ESTER DERIVATIVE, ITS PREPARATION AND ANTIPHLOGISTIC AND ANALGESIC AGENT CONTAINING SAID DERIVATIVE AS ACTIVE COMPONENT", 28 July 1983 (1983-07-28), XP055442267, Retrieved from the Internet <URL:file:///C:/Users/MH52034/Desktop/JPS58126846%20translation.pdf> [retrieved on 20180118] *
No further relevant documents disclosed *
See also references of WO2008020270A1 *
SHANBHAG V R: "ESTER AND AMIDE PRODRUGS OF IBUPROFEN AND NAPROXEN: SYNTHESIS, ANTI-INFLAMMATORY ACTIVITY, AND GASTROINTESTINAL TOXICITY", JOURNAL OF PHARMACEUTICAL SCIENCES, AMERICAN PHARMACEUTICAL ASSOCIATION, WASHINGTON, US, vol. 81, no. 2, 1 February 1992 (1992-02-01), pages 149 - 154, XP000248778, ISSN: 0022-3549, DOI: 10.1002/JPS.2600810210 *

Also Published As

Publication number Publication date
CN101506161A (en) 2009-08-12
AU2006347391A1 (en) 2008-02-21
AU2006347391B2 (en) 2013-03-07
JP2010500989A (en) 2010-01-14
EP2054384A1 (en) 2009-05-06
CA2660814A1 (en) 2008-02-21
HK1137425A1 (en) 2010-07-30
CA2660814C (en) 2017-07-18
JP5424880B2 (en) 2014-02-26
WO2008020270A1 (en) 2008-02-21
CN101506161B (en) 2013-11-13

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