DK2049482T3 - Positivt ladede, vandopløselige prodrugs af aryl- og heteroaryleddikesyrer med meget hurtig hudpenetrationshastighed - Google Patents

Positivt ladede, vandopløselige prodrugs af aryl- og heteroaryleddikesyrer med meget hurtig hudpenetrationshastighed Download PDF

Info

Publication number
DK2049482T3
DK2049482T3 DK06795612.8T DK06795612T DK2049482T3 DK 2049482 T3 DK2049482 T3 DK 2049482T3 DK 06795612 T DK06795612 T DK 06795612T DK 2049482 T3 DK2049482 T3 DK 2049482T3
Authority
DK
Denmark
Prior art keywords
diethylaminoethyl
acoh
acetate
compound
chlorobenzoyl
Prior art date
Application number
DK06795612.8T
Other languages
English (en)
Inventor
Chongxi Yu
Lina Xu
Original Assignee
Techfields Biochem Co Ltd
Chongxi Yu
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, Chongxi Yu filed Critical Techfields Biochem Co Ltd
Application granted granted Critical
Publication of DK2049482T3 publication Critical patent/DK2049482T3/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/10—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of a carbon skeleton containing rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A61K38/13—Cyclosporins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Immunology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Claims (14)

1. Forbindelse valgt blandt gruppen bestående af: Diethylaminoethyl 1 -(p-chlorobenzoyl)-5-methoxy-2-methylindol 3-acetat.AcOH, Diethylaminoethyl (Z)-5-fluoro-2-methyl-1 -[(4-methylsulfinyl) phenylmethylen]-1 H-inden-3-acetat.AcOH, Diethylaminoethyl 1 -methyl-5-(4-methylbenzoyl)-1 H-pyrrol-2-acetat.AcOH, Diethylaminoethyl 5-(4-Chlorobenzoyl)-1,4-dimethyl-1 H-pyrrol-2-acetat.AcOH, Diethylaminoethyl 1,8-diethyl-1,3,4,9-tetrahydropyrano-[3 ,4-b]indol-1-acetat.AcOH, Diethylaminoethyl 2-amino-3-benzoylbenzenacetat.AcOH, Diethylaminoethyl 2-amino-3-(4-bromo-benzoyl)benzenacetat.AcOH, Diethylaminoethyl 3-chloro-4-(2-propenyloxy)benzenacetat.AcOH, Diethylaminoethyl 2-(2,4-dichlorophenoxy)benzenacetat.AcOH, Diethylaminoethyl 1 -(4-chlorobenzoyl-5-methoxy-2-methyl-1 H-indol-3-acetoxy acetat. AcO H, Diethylaminoethyl 4-(4-chlorophenyl)-2-phenyl-5-thiazolacetat.AcOH, Diethylaminoethyl 3 -(4-chlorophenyl)-1-phenyl-1 H-pyrazol-4-acetat.AcOH, Diethylaminoethyl [(1-benzyl- 1H-indazol-3-yl)oxy]acetat.AcOH, Diethylaminoethyl 6-methoxyl-2-naphthalen-2-acetat.AcOH, og Diethylaminoethyl p-isobutylphenylacetat.AcOH.
2. Fremgangsmåde til fremstilling af en forbindelse ifølge krav 1, hvor syrehalogenider eller blandede anhydrider af tolmetin, zomepirac, etodolac, amfenac, bromofenac, alclofenac, fenclofenac, acemetacin, fentiazac, indomethacin, sulindac, lonazolac, bendazac, 6MNA eller ibufenac reageres med forbindelser med den almene struktur (3)
Struktur 3 hvor R3 i struktur 3 repræsenterer ethyl; R4 repræsenterer ethyl; X repræsenterer O; og n = 2.
3. Fremgangsmåde til fremstilling af en forbindelse ifølge krav 1, hvor tolmetin, zomepirac, etodolac, amfenac, bromofenac, alclofenac, fenclofenac, acemetacin, fentiazac, indomethacin, sulindac, lonazolac, bendazac, 6MNA eller ibufenac reageres med en forbindelse med den almene struktur (3)
Struktur 3 hvor R3 i struktur 3 repræsenterer ethyl; R4 repræsenterer ethyl; X repræsenterer O; og n = 2, ved at anvende koblingsreagenser.
4. Fremgangsmåde ifølge krav 3, hvor koblingsreagenserne er valgt blandt gruppen bestående af Ν,Ν'-Dicyclohexylcarbodiimid, N, N'-Diisopropyl-carbodiimid, 0-(Benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium tetrafluoroborat, 0-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluroniumhexafluorophosphat og Benzotriazol-1-yl-oxy-tris (dimethylamino)phosphoniumhexafluorophosphat.
5. Fremgangsmåde til fremstilling af en forbindelse ifølge krav 1, hvor metalsalte, organiske basiske salte eller immobiliserede basiske salte af tolmetin, zomepirac, etodolac, amfenac, bromofenac, alclofenac, fenclofenac, acemetacin, fentiazac, indomethacin, sulindac, lonazolac, bendazac, 6MNA, ibufenac og beslægtede forbindelser reageres med forbindelser med den almene struktur 4,
Struktur 4 hvor R2 i struktur 4 repræsenterer H, R3 repræsenterer ethyl; R4 repræsenterer ethyl; Z repræsenterer halogen eller p-toluensulphonyl, A' repræsenterer en hvilken som helst negativ ion og n = 2.
6. Sammensætning indeholdende mindst en forbindelse ifølge krav 1.
7. Forbindelse ifølge krav 1 eller farmaceutisk sammensætning ifølge krav 6 til anvendelse i en fremgangsmåde til behandling af en lidelse, der kan behandles med et ikke-steroidt, antiinflammatorisk middel (NSAIA), valgt blandt gruppen bestående af smerte fra tandpine, hovedpine og arthritis og anden inflammatorisk smerte, feber, cancer, dysmenorré, strålingsinduceret opkastning, diabetisk neuropati og akut migrænehovedpine, hæmofil artropati, knogletab og solskoldning hos mennesker eller dyr.
8. Forbindelse eller sammensætning til anvendelse ifølge krav 7, hvor anvendelserne omfatter indgift af forbindelsen eller sammensætningen transdermalt i en hvilken som helst del af kroppen for at opnå terapeutisk effektive plasmaniveauer af forbindelsen.
9. Forbindelse eller sammensætning til anvendelse ifølge krav 7, hvor lidelsen, der kan behandles med NSAIA, er valgt blandt gruppen bestående af hovedpine, tandpine og muskelsmerte samt arthritis og anden inflammatorisk smerte, og omfattende indgift i det betændte område af en terapeutisk effektiv mængde af forbindelsen eller sammensætningen.
10. Forbindelse eller sammensætning til anvendelse ifølge krav 7, hvor lidelsen, der kan behandles med NSAIA, er valgt blandt gruppen bestående af akne, solskoldning eller andre hudlidelser, hvor forbindelsen eller sammensætningen indgives transdermalt og er i form af en opløsning, spray, lotion, salve, emulsion eller gel.
11. Forbindelse eller sammensætning til anvendelse ifølge krav 7, hvor lidelsen, der kan behandles med NSAIA, er astma, hvor forbindelsen eller sammensætningen indgives ved at spraye gennem munden eller næsen eller andre dele af kroppen.
12. Forbindelse eller sammensætning til anvendelse ifølge krav 7, hvor lidelsen, der kan behandles med NSAIA, er valgt blandt gruppen bestående af øjenbetændelsessygdomme, okulær smerte efter hornhindekirurgi, glaucoma og ørebetændelses- og/eller øresmertelidelser (otitis).
13. Transdermalt terapeutisk indgiftssystem omfattende mindst en forbindelse ifølge krav 1 som en aktiv ingrediens til anvendelse i en fremgangsmåde til behandling af lidelser, der kan behandles med NSAIA, hos mennesker eller dyr.
14. Transdermalt terapeutisk indgiftssystem ifølge krav 13, hvor systemet er en bandage eller et plaster omfattende et matrixlag, der indeholder aktivt stof, og et impermeabelt støttelag, eller hvor systemet er et aktivt stof reservoir, der har en permeabel bund, der vender mod huden.
DK06795612.8T 2006-08-08 2006-08-08 Positivt ladede, vandopløselige prodrugs af aryl- og heteroaryleddikesyrer med meget hurtig hudpenetrationshastighed DK2049482T3 (da)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2006/052732 WO2008017903A1 (en) 2006-08-08 2006-08-08 Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate

Publications (1)

Publication Number Publication Date
DK2049482T3 true DK2049482T3 (da) 2016-02-01

Family

ID=39032656

Family Applications (1)

Application Number Title Priority Date Filing Date
DK06795612.8T DK2049482T3 (da) 2006-08-08 2006-08-08 Positivt ladede, vandopløselige prodrugs af aryl- og heteroaryleddikesyrer med meget hurtig hudpenetrationshastighed

Country Status (8)

Country Link
EP (2) EP2990402A1 (da)
CN (1) CN101506160A (da)
DK (1) DK2049482T3 (da)
ES (1) ES2559781T3 (da)
HU (1) HUE028425T2 (da)
PL (1) PL2049482T3 (da)
PT (1) PT2049482E (da)
WO (1) WO2008017903A1 (da)

Families Citing this family (19)

* 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
EP2781505A1 (en) 2006-10-02 2014-09-24 Techfields Biochem Co. Ltd Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin penetration rates
AU2006350707A1 (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
CN109503446B (zh) 2007-01-15 2021-08-20 于崇曦 维生素a酸类和类维生素a酸化合物的前药
HUE031307T2 (hu) 2007-01-31 2017-07-28 Chongxi Yu 1H-imidazo[4,5-C]kinolin-4-aminok és rokon vegyületek pozitív töltésû vízoldható prodrugjai, amelyek nagyon magas bõr-penetrációs sebességekkel rendelkeznek
WO2008149181A1 (en) * 2007-06-04 2008-12-11 Techfields Inc Pro-drugs of nsaias with very high skin and membranes penetration rates and their new medicinal uses
RU2630577C2 (ru) 2008-12-04 2017-09-11 Чунси ЮЙ Композиции интенсивного проникновения и их применение
PL2427475T3 (pl) 2009-05-08 2021-07-19 Techfields Biochem Co., Ltd. Kompozycje proleku o wysokim przenikaniu peptydów i związków powiązanych z peptydami
US9969751B2 (en) 2009-06-10 2018-05-15 Techfields Pharma Co., Ltd. High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds
CN102557976B (zh) * 2010-12-15 2015-06-10 辽宁盛京制药有限公司 溴芬酸有机盐及其制备方法、其组合物及用途
ES2969344T3 (es) * 2012-01-18 2024-05-17 Techfields Pharma Co Ltd Composiciones de profármaco de alta penetración y composición farmacéutica del mismo para el tratamiento de afecciones pulmonares
BR112015022896B1 (pt) 2013-03-15 2022-08-23 Chongxi Yu Composto de fármacos de alta penetração, composição farmacêutica e seus usos para o tratamento de doenças de parkinson
JP5997658B2 (ja) * 2013-05-08 2016-09-28 テックフィールズ インコーポレイテッド 非常に速い皮膚及び膜浸透速度を有するｎｓａｉａプロドラッグ及びその新規医薬使用
US20160168108A1 (en) 2014-12-16 2016-06-16 Adt Pharmaceuticals, Inc. Method of treating or preventing ras-mediated diseases
US9862698B2 (en) 2014-12-16 2018-01-09 Adt Pharmaceuticals, Inc. Indenyl compounds, pharmaceutical compositions, and medical uses thereof
WO2019067974A1 (en) * 2017-09-28 2019-04-04 Medical Pharmaceuticals, Inc. ANTI-INFLAMMATORY, ANTICANCER AND ANTI-ANGIOGENIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND METHODS OF MAKING AND USING THEM
CN112020354A (zh) 2018-04-26 2020-12-01 Adt制药有限责任公司 抗癌茚类、茚满类、氮杂茚类、氮杂茚满类、药物组合物和用途

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1593024A (da) * 1968-09-18 1970-05-25
IT1090782B (it) * 1977-11-30 1985-06-26 Menarini Sas 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi
US5192753A (en) 1991-04-23 1993-03-09 Mcgeer Patrick L Anti-rheumatoid arthritic drugs in the treatment of dementia
US5654337A (en) 1995-03-24 1997-08-05 II William Scott Snyder Topical formulation for local delivery of a pharmaceutically active agent
AUPN531195A0 (en) 1995-09-11 1995-10-05 J.W. Broadbent Nominees Pty. Ltd. Lipid extract having anti-inflamatory activity
KR100213465B1 (ko) 1996-11-01 1999-08-02 최좌진 케토프로펜 패취 조성물
US5885597A (en) 1997-10-01 1999-03-23 Medical Research Industries,Inc. Topical composition for the relief of pain
PT1094781E (pt) 1998-07-07 2008-10-08 Transdermal Technologies Inc Composições para administração transdérmica rápida e não irritante de agentes farmacologicamente activos e métodos para formulação de tais composições e sua administração
IT1317826B1 (it) * 2000-02-11 2003-07-15 Dompe Spa Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8.
US6416772B1 (en) 2001-01-12 2002-07-09 H. Wayne Van Engelen Topical dermal anaesthetic
US6528040B1 (en) 2001-01-18 2003-03-04 Maurine Pearson EMU oil-based formulations for use as an analgesic, anesthetic and antipruritic
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
US7052715B2 (en) 2003-04-11 2006-05-30 All Natural Fmg, Inc. Alcohol-free transdermal analgesic composition and processes for manufacture and use thereof

Also Published As

Publication number Publication date
EP2049482A4 (en) 2010-05-26
EP2990402A1 (en) 2016-03-02
EP2049482A1 (en) 2009-04-22
WO2008017903A1 (en) 2008-02-14
PT2049482E (pt) 2016-02-24
PL2049482T3 (pl) 2016-04-29
EP2049482B1 (en) 2015-10-21
HUE028425T2 (en) 2016-12-28
ES2559781T3 (es) 2016-02-15
CN101506160A (zh) 2009-08-12

Similar Documents

Publication Publication Date Title
DK2041068T3 (da) Positivt ladede, vandopløselige prodrugs af ibuprofen med meget hurtig hudpenetrationshastighed
AU2006347391B2 (en) Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate
EP2046727B1 (en) Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
EP2049482B1 (en) Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate
EP2623495B1 (en) Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate
AU2017201728A1 (en) Positively charged water-soluble prodrugs of 1H-imidazo[4,5-c]quinolin-4-amines and related compounds with very high skin penetration rates
WO2008012605A1 (en) Positively charged water-soluble prodrugs of ketoprofen and related compounds with very fast skin penetration rate
AU2013206218B2 (en) Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate
CN103772259B (zh) 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药
CN103772258B (zh) 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药
AU2018202140A1 (en) Positively charged water-soluble pro-drugs of ibuprofen
HK1137424A (en) Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate
HK1196823B (en) Positively charged aryl and heteroaryl acetic acid prodrugs with high skin penetration rate
HK1196823A (en) Positively charged aryl and heteroaryl acetic acid prodrugs with high skin penetration rate
HK1196824B (en) Positively charged aryl and heteroaryl acetic acid prodrugs with high skin penetration rate
HK1198001A (en) Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
HK1188210A (en) Positively charged water-soluble prodrugs of n-arylanthranilic acids with very fast skin penetration rate
HK1137425B (en) Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate
HK1196284A (en) Positively-charged water-soluble aryl and heteroaryl propionic acid prodrug with rapid skin penetrating speed