DK2616069T3 - Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol - Google Patents

Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol Download PDF

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Publication number
DK2616069T3
DK2616069T3 DK11760963.6T DK11760963T DK2616069T3 DK 2616069 T3 DK2616069 T3 DK 2616069T3 DK 11760963 T DK11760963 T DK 11760963T DK 2616069 T3 DK2616069 T3 DK 2616069T3
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Prior art keywords
methyl
ethyl
imidazol
benzyl ester
acid
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DK11760963.6T
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English (en)
Inventor
Ken Chow
Mohammed I Dibas
John E Donello
Michael E Garst
Daniel W Gil
Liming Wang
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Allergan Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (6)

1. Forbindelse udvalgt fra følgende forbindelser eller farmaceutisk acceptabelt salt deraf: iso-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2.2- dimethyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; eddikesyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; benzoesyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-amino-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-amino-3-methyl-butyrylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4yl)-ethyl]-2-methyl-benzylester; 2-(2-amino-acetylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2methyl-benzylester og 2- amino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester.
2. Forbindelse udvalgt fra følgende forbindelser eller farmaceutisk acceptabelt salt deraf: iso-smørsyre 3-[(S)-l-(l-iso-butyryl-lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2.2- dimethyl-propionsyre 3-{(S)-l-[l-(2,2-dimethyl-propiony)-lH-imidazol-4-yl]ethyl>-2-methyl-benzylester; eddikesyre 3-[(S)-l-(l-acetyl-lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; benzoesyre 3-[(S)-l-(l-benzoyl-lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 3- methyl-smørsyre 2-methyl-3-{(S)-l-[l-(3-methyl-butyryl)-lH-imidazol-4-yl]-ethyl}-benzylester; phenyl-propionsyre 2-methyl-3-{(S)-l-[l-(3-phenyl-propiony)-l/-/-imidazol-4-yl]ethyl}-benzylester; 2-tert-butoxycarbonylamino-3-methyl-smørsyre 3-{(S)-l-[l-(2-teri--butoxy carbonylamino-3-methyl-butyryl)-lH-imidazol-4-yl]-ethyl}-2-methyl- benzylester; 2-tert-butoxycarbonylamino-3-methyl-smørsyre 3-((S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-methyl- smørsyre {(S)-l-[l-(2-terf--butoxycarbonylamino-3-methyl-butyryl)-lAV- imidazol-4-yl]-ethyl}-2methyl-benzylester; 2-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-methyl-smørsyre 3[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-tert-butoxycarbonylamino-acetylamino)-3-methyl-smørsyre 3-[(S)- 1- (lHimidazol-4-yl)-ethyl]-2-methyl-benzylester og 2- tert-butoxycarbonylamino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester.
3. Farmaceutisk sammensætning omfattende en forbindelse eller farmaceutisk acceptabelt salt deraf som defineret i krav 1.
4. Forbindelse eller farmaceutisk acceptabelt salt deraf som defineret i krav 1 til anvendelse i en fremgangsmåde til behandling eller forebyggelse af en tilstand eller en sygdom, der Undres af alpha 2A-, 2B-, 2C-aktivering, hvilken tilstand eller sygdom er udvalgt fra glaukom, forhøjet intraokulært tryk, iskæmisk neuropati, optisk neuropati, smerte, en retinal degenerativ tilstand, såsom diabetisk retinopati, apopleksi, en kognitiv svækkelse, en neuropsykiatrisk tilstand, lægemiddelafhængighed og -misbrug, abstinenssymptomer, obsessiv-kompulsiv tilstand, fedme, insulinresistens, en stress-relateret tilstand, diarre, diurese, nasal kongestion, spasticitet, ADHD, psykoser, angst, depression, autoimmun sygdom, Crohns sygdom, gastritis, en neurodegenerativ sygdom, såsom Alzheimers sygdom, Parkinsons sygdom og ALS, akne, aldersrelateret makuladedegeneration, våd makuladedegeneration, tør makuladedegeneration, geografisk atrofi, diabetisk makulaødem, en tumor, et sår, inflammation og retinal veneokklusion, synstab, såsom grundet glaukom, retinitis pigmentosa eller neuritis sekundær til multipel sklerose, rosacea (udvidelse af blodkar lige under huden), solforbrænding, kronisk solskade, diskret erytem, psoriasis, menopause-forbunden hedeture, hedeture som følge af orchiektomi-atopisk dermatitis, fotoældning, seborrhoisk dermatitis, allergisk dermatitis, huderytem (rødmen), telangiektasi (udvidelser af tidligere eksisterende små blodkar) i ansigtet, rhinophyma (hypertrofi af næsen med follikeludvidelse), rød bulbøs næse, akne-lignende hududbrud, brændende eller svidende fornemmelse i ansigtet, irriterede og blodskudte og løbende øjne, kutan hyperaktivitet med udvidelse af blodkar i huden, Lyells syndrom, Stevens-Johnson-syndrom, erythema multiforme minor og erythema multiforme major.
5. Farmaceutisk sammensætning ifølge krav 3 til anvendelse i en fremgangsmåde til behandling eller forebyggelse afen tilstand eller sygdom, der er udvalgt fra de tilstande eller sygdomme, der er defineret i krav 4.
6. Sammensætning eller salt deraf til anvendelse ifølge krav 4 eller farmaceutisk sammensætning til anvendelse ifølge krav 5, hvor smerten er udvalgt fra visceral smerte, hornhindesmerte, hovedpinesmerte, migrænesmerte, cancersmerte, rygsmerte, smerte ved irritabel tarmsyndrom, muskelsmerte og smerte forbundet med diabetisk neuropati.
DK11760963.6T 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol DK2616069T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38337010P 2010-09-16 2010-09-16
PCT/US2011/052004 WO2012037499A1 (en) 2010-09-16 2011-09-16 Ester pro-drugs of [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol

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DK2616069T3 true DK2616069T3 (da) 2016-12-19

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DK16161921.8T DK3078376T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af nethindesygdomme
DK19194325.7T DK3636263T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl]-methanol
DK16161922.6T DK3053576T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk
DK11760962.8T DK2616068T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk
DK11760963.6T DK2616069T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol
DK16161923T DK3050564T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl]-methanol
DK18160174.1T DK3348264T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk
DK18157147.2T DK3338777T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af nethindesygdomme
DK16161920.0T DK3050563T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af hudsygdomme og -tilstande

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DK16161921.8T DK3078376T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af nethindesygdomme
DK19194325.7T DK3636263T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl]-methanol
DK16161922.6T DK3053576T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk
DK11760962.8T DK2616068T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk

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DK16161923T DK3050564T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl]-methanol
DK18160174.1T DK3348264T3 (da) 2010-09-16 2011-09-16 Ester pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til sænkning af intraokulært tryk
DK18157147.2T DK3338777T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af nethindesygdomme
DK16161920.0T DK3050563T3 (da) 2010-09-16 2011-09-16 Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af hudsygdomme og -tilstande

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EP (13) EP3050564B1 (da)
JP (4) JP2013541527A (da)
KR (7) KR101952457B1 (da)
CN (5) CN105412092B (da)
AR (4) AR083019A1 (da)
AU (4) AU2011301856C1 (da)
BR (4) BR112013006320B1 (da)
CA (8) CA2811559A1 (da)
CL (4) CL2013000733A1 (da)
CY (3) CY1121024T1 (da)
DK (9) DK3078376T3 (da)
ES (10) ES2760920T3 (da)
HK (5) HK1185540A1 (da)
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IL (4) IL225280A0 (da)
MX (4) MX2013003002A (da)
MY (4) MY173846A (da)
NZ (1) NZ608751A (da)
PL (7) PL2616069T3 (da)
PT (7) PT3050563T (da)
RU (4) RU2013116403A (da)
SG (4) SG188571A1 (da)
SI (5) SI3348264T1 (da)
TR (1) TR201909249T4 (da)
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UA (1) UA112973C2 (da)
WO (4) WO2012037453A1 (da)
ZA (4) ZA201302193B (da)

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US8501796B2 (en) 2013-08-06
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EP3348264B1 (en) 2020-01-01
UA112973C2 (uk) 2016-11-25
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EP2616066A1 (en) 2013-07-24
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EP3636263B1 (en) 2021-11-03
KR20140003407A (ko) 2014-01-09
CA2812195A1 (en) 2012-03-22
PT2616068T (pt) 2016-09-13
US20130289088A1 (en) 2013-10-31
US20160354346A1 (en) 2016-12-08
EP3698789A1 (en) 2020-08-26
KR102354097B1 (ko) 2022-01-20
HUE039090T2 (hu) 2018-12-28
ES2613509T3 (es) 2017-05-24
EP2616067B1 (en) 2016-05-18
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RU2013116763A (ru) 2014-10-27
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AU2011301901B2 (en) 2016-02-11
US20120136036A1 (en) 2012-05-31
IL225281A0 (en) 2013-06-27
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WO2012037453A1 (en) 2012-03-22
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