DK3050563T3 - Ester-pro-drugs af [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl] methanol til behandling af hudsygdomme og -tilstande - Google Patents

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

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DK3050563T3
DK3050563T3 DK16161920.0T DK16161920T DK3050563T3 DK 3050563 T3 DK3050563 T3 DK 3050563T3 DK 16161920 T DK16161920 T DK 16161920T DK 3050563 T3 DK3050563 T3 DK 3050563T3
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methyl
ethyl
imidazol
benzyl ester
acid
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DK16161920.0T
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Ken Chow
John E Donello
Michael E Garst
Daniel W Gil
Liming Wang
Mohammed I Dibas
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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
    • 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
    • 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

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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 (2)

1. Sammensætning til anvendelse i behandling af hudsygdomme og hudtilstande hos en menneskelig patient med behov for sådan behandling ved topikal dermatologisk anvendelse af en terapeutisk effektiv mængde af nævnte sammensætning omfattende en forbindelse ifølge formel I, dets individuelle enantiomerer, dets individuelle diastereoisomerer, dets hydrater, dets solvater, dets krystalformer, dets individuelle tautomerer eller et farmaceutisk acceptabelt salt deraf, O R2 R1 R3 Formel I hvor R1 er H eller C1-3 alkyl; R2 er H eller C1-3 alkyl; R3 er H, Ci-10 alkyl, heterocykel eller aryl; og R er Ci-10 alkyl, heterocykel eller aryl, hvor "alkyl" betyder en mættet monovalent alkandel, som har lige eller forgrenede alkandele eller kombinationer deraf, som eventuelt kan substitueres af aminogrupper, arylgrupper, halogener, og et methylen (-CH2-) kan erstattes af carbonyl, -NH-, carboxyl, amid, svovl eller af oxygen, og "heterocykel" betyder en aromatisk eller ikke-aromatisk 5- til 10-leddet monocyklisk eller bicyklisk ring, som indeholder mindst ét heteroatom valgt fra O eller N eller S eller kombinationer deraf, som afbryder den carbocykliske ringstruktur, som eventuelt kan substitueres af C1-6 alkyl,
amino, halogen, -O(Ci-e alkyl), - OC(O)(Ci-e alkyl), -C(O)O(Ci-e alkyl), -NHC(O)(Ci-e alkyl), -C(O)NH(Ci-e alkyl), - S(Ci-e alkyl) grupper, og "aryl" betyder en organisk del afledt fra et aromatisk carbonhydrid bestående afen monocyklisk eller bicyklisk ring, som indeholder 6-10 kulstofatomer ved fjernelse af et hydrogenatom, såsom phenyl eller naphthyl, som eventuelt kan substitueres af, men ikke begrænset til, Ci-6 alkyl, amino, halogen, -O(Ci-e alkyl), - OC(O)(Ci-e alkyl), -C(O)O(Ci-e alkyl), -NHC(O)(Ci-6 alkyl), -C(O)NH(Ci-6 alkyl), og -S(Ci-e alkyl) grupper; og hvor nævnte hudsygdomme og hudtilstande er valgt fra: rosacea, solforbrænding, kronisk solskade, diskret erytem, psoriasis, atopisk dermatitis, menopauseforbunden hedeture, hedeture som følge af orchiektomi-atopisk dermatitis, fotoældning, seborrhoisk dermatitis, akne, allergisk dermatitis, og irriteret dermatitis.
2. Sammensætning til anvendelse ifølge krav 1, hvor forbindelsen er som defineret af formel II, dets individuelle diastereoisomerer, dets hydrater, dets solvater, dets krystalformer, dets individuelle tautomerer eller et farmaceutisk acceptabelt salt deraf, O R2 R1 V Formel II hvor R1, R2, R3 og R er som defineret ovenfor.
3. Sammensætning til anvendelse ifølge krav 1, hvor forbindelsen er som defineret af formel III, dets individuelle diastereoisomerer, dets hydrater, dets solvater, dets krystalformer, dets individuelle tautomerer eller et farmaceutisk acceptabelt salt deraf,
O R2 R1 Nv> XR3 Formel III hvor R1, R2, R3 og R er som defineret ovenfor.
4. Sammensætning til anvendelse ifølge krav 2, hvor R1 er C1-3 alkyl, R2 er C1-3 alkyl, R3 er H og R er C1-10 alkyl.
5. Sammensætning til anvendelse ifølge krav 2, hvor R1 er methyl, R2 er methyl, R3 er H og R er C1-4 alkyl.
6. Sammensætning til anvendelse ifølge krav 2, hvor forbindelsen er valgt fra: 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-methylbenzylester; 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-methylbenzylester; 2-(2-Amino-3-methyl-butyrylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-Amino-acetylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; og
2- Amino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methylbenzylester.
7. Sammensætning til anvendelse ifølge krav 2, hvor forbindelsen er valgt fra: iso-smørsyre 3-[(S)-l-(l-iso-butyryl-lH-imidazol-4-yl)-ethyl]-2-methylbenzylester; 2,2-Dimethyl-propionsyre 3-{(S)-l-[l-(2,2-dimethyl-propionyl)-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-propionyl)-lH-imidazol-4-yl]-ethyl}-benzylester; 2-tert-Butoxycarbonylamino-3-methyl-smørsyre 3-{(S)-l-[l-(2-tert-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 3-{(S)-l-[l-(2-tert-butoxycarbonylamino-3-methyl-butyryl)-lH-imidazol-4-yl]-ethyl}-2-methyl-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)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; og 2-tert-Butoxycarbonylamino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester.
8. Artikel til fremstilling omfattende indpakningsmateriale og et farmaceutisk middel indeholdt i nævnte indpakningsmateriale, hvor det farmaceutiske middel er terapeutisk effektiv til behandling af hudsygdomme og hudtilstande, og hvor indpakningsmaterialet omfatter et mærke, som indikerer, at det farmaceutiske middel kan anvendes til behandling af hudsygdomme og hudtilstande, og hvor nævnte farmaceutiske middel omfatter en effektiv mængde af en forbindelse valgt fra: 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-methylbenzylester; 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-methylbenzylester; 2-(2-Amino-3-methyl-butyrylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-Amino-acetylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; og
2-Amino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methylbenzylester.
9. Artikel til fremstilling omfattende indpakningsmateriale og et farmaceutisk middel indeholdt i nævnte indpakningsmateriale, hvor det farmaceutiske middel er terapeutisk effektiv til behandling af hudsygdomme og hudtilstande, og hvor indpakningsmaterialet omfatter et mærke, som indikerer, at det farmaceutiske middel kan anvendes til behandling af hudsygdomme og hudtilstande, og hvor nævnte farmaceutiske middel omfatter en effektiv mængde af en forbindelse valgt fra: iso-smørsyre 3-[(S)-l-(l-iso-butyryl-lH-imidazol-4-yl)-ethyl]-2-methylbenzylester; 2,2-Dimethyl-propionsyre 3-{(S)-l-[l-(2,2-dimethyl-propionyl)-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-propionyl)-lH-imidazol-4-yl]-ethyl}-benzylester; 2-tert-Butoxycarbonylamino-3-methyl-smørsyre 3-{(S)-l-[l-(2-tert-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 3-{(S)-l-[l-(2-tert-butoxycarbonylamino-3-methyl-butyryl)-lH-imidazol-4-yl]-ethyl}-2-methyl-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)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; og 2-tert-Butoxycarbonylamino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol- 4-yl)-ethyl]-2-methyl-benzylester.
10. Farmaceutisk sammensætning til behandling af hudsygdomme og hudtilstande hos en menneskelig patient omfattende en forbindelse med en struktur O R2 R1 R3 Formel II hvor R1, R2, R3 og R er som defineret ovenfor.
11. Den farmaceutiske sammensætning ifølge krav 10, hvor forbindelsen er valgt fra: 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-methylbenzylester; 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-methylbenzylester; 2-(2-Amino-3-methyl-butyrylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; 2-(2-Amino-acetylamino)-3-methyl-smørsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methyl-benzylester; og
2-Amino-3-phenyl-propionsyre 3-[(S)-l-(lH-imidazol-4-yl)-ethyl]-2-methylbenzylester.
DK16161920.0T 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 DK3050563T3 (da)

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US38337010P 2010-09-16 2010-09-16
EP11760961.0A EP2616067B1 (en) 2010-09-16 2011-09-16 Ester pro-drugs of [3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl]methanol for treating skin diseases and conditions

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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
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
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
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
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
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
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

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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
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
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
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
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

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