SI2989100T1 - Naftiridinski derivati, uporabni kot antagonisti integrina alfa-v-beta-6 - Google Patents

Naftiridinski derivati, uporabni kot antagonisti integrina alfa-v-beta-6 Download PDF

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SI2989100T1
SI2989100T1 SI201430687T SI201430687T SI2989100T1 SI 2989100 T1 SI2989100 T1 SI 2989100T1 SI 201430687 T SI201430687 T SI 201430687T SI 201430687 T SI201430687 T SI 201430687T SI 2989100 T1 SI2989100 T1 SI 2989100T1
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ethyl
pharmaceutically acceptable
acceptable salt
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Niall Andrew Anderson
Brendan John Fallon
John Martin Pritchard
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Glaxosmithkline Intellectual Property Development Limited
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

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  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Claims (23)

  1. NAFTIRIDINSKI DERIVATI, UPORABNI KOT ANTAGONISTI INTEGRINA ALFA-V-BETA-6 PATENTNI ZAHTEVKI
    1. Spojina s formulo (I)
    kjer Ri predstavlja atom vodika, metilno skupino ali etilno skupino; R2 predstavlja atom vodika ali atom fluora; R3 predstavlja atom vodika, metilno skupino ali etilno skupino; ali farmacevtsko sprejemljiva sol le-te.
  2. 2. Spojina s formulo (I) po zahtevku 1, kjer R1 predstavlja metilno skupino, R2 predstavlja atom vodika in R3 predstavlja metilno skupino; ali farmacevtsko sprejemljiva sol le-te.
  3. 3. Spojina s formulo (I) po zahtevku 1, pri kateri R1 predstavlja etilno skupino, R2 predstavlja atom vodika in R3 predstavlja etilno skupino; ali farmacevtsko sprejemljiva sol le-te.
  4. 4. Spojina s formulo (I) po zahtevku 1, pri kateri Ri predstavlja atom vodika, R2 predstavlja atom vodika in R3 predstavlja metilno skupino; ali farmacevtsko sprejemljiva sol le-te.
  5. 5. Spojina s formulo (I) po zahtevku 1.
  6. 6. Spojina s formulo (I), kot je zahtevano v katerem koli od zahtevkov 1 do 5, s konfiguracijo:
  7. 7. Spojina s formulo (I) po zahtevku 1, ki je izbrana iz naslednjih: 3-(3-(3,5-dimetil-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina; 3-(3-(5-metil-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina; 3-(3-(5-etil-3-metil-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -iljbutanojska kislina; 3-(3-(1 H-pirazol-1-il)fenil)-4-((H)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -iljbutanojska kislina; 3-(3-(3,5-dietil-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina; 3-(3-(4-fluoro-3,5-dimetil-1 H-pirazol-1-il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina; 3-(3-(3-metil-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina; ali farmacevtsko sprejemljiva sol le-te.
  8. 8. Spojina s formulo (I) po zahtevku 1, ki je: 3-(3-(3,5-d imeti 1-1 H-pirazol-1 -il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1 -il)butanojska kislina:
  9. 9. Spojina s formulo (I) po zahtevku 1, ki je (S)-3-(3-(3,5-dimetil-1H-pirazol-1-il)fenil)-4-((/?)-3-(2-(5,6,7I8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1-il)butanojska kislina
  10. 10. Spojina po zahtevku 1, ki je hidrokloridna sol 3-(3-(3,5-dimetil-1H-pirazol-1-il)fenil)-4-((/?)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1-il)butanojske kisline.
  11. 11. Spojina po zahtevku 1, ki je hidrokloridna sol (S)-3-(3-(3,5-dimetil-1/-/-pirazol-1-il)fenil)-4-((R)-3-(2-(5,6,7,8-tetrahidro-1,8-naftiridin-2-il)etil)pirolidin-1-il)butanojske kisline.
  12. 12. Spojina s formulo (I) ali farmacevtsko sprejemljiva sol le-te po katerem koli od zahtevkov 1 do 11, za uporabo pri terapiji.
  13. 13. Spojina s formulo (I) ali farmacevtsko sprejemljiva sol le-te po katerem koli od zahtevkov 1 do 11, za uporabo pri zdravljenju bolezni ali stanja, za katero je indiciran antagonist receptorja ανβ6.
  14. 14. Spojina s formulo (I) ali farmacevtsko sprejemljiva sol le-te po katerem koli od zahtevkov 1 do 11, za uporabo pri zdravljenju fibrotične bolezni.
  15. 15. Spojina s formulo (I) ali farmacevtsko sprejemljiva sol le-te, za uporabo po zahtevku 14, kjer je fibrotična bolezen pljučna fibroza.
  16. 16. Spojina s formulo (I) ali farmacevtsko sprejemljiva sol le-te po katerem koli od zahtevkov 1 do 11, za uporabo pri zdravljenju idiopatične pljučne fibroze.
  17. 17. Farmacevtski sestavek, ki obsega spojino s formulo (I) ali farmacevtsko sprejemljivo sol le-te po katerem koli od zahtevkov 1 do 11 in enega ali več farmacevtsko sprejemljivih nosilcev, razredčil ali ekscipientov.
  18. 18. Kombinacija, ki obsega spojino s formulo (I) ali farmacevtsko sprejemljivo sol lete po katerem koli od zahtevkov 1 do 11 in vsaj eno drugo farmacevtsko aktivno sredstvo.
  19. 19. Kombinacija, kot je zahtevano v zahtevku 18, za uporabo pri terapiji.
  20. 20. Kombinacija, kot je zahtevano v zahtevku 18, ali kombinacija za uporabo, kot je zahtevano v zahtevku 19, kjer je inhibitor sinteze TGFp, na primer pirfenidon, drugo farmacevtsko aktivno sredstvo.
  21. 21. Kombinacija, kot je zahtevano v zahtevku 18, ali kombinacija za uporabo, kot je zahtevano v zahtevku 19, kjer je drugo farmacevtsko aktivno sredstvo nintedanib (BIBF-1120).
  22. 22. Kombinacija, kot je zahtevano v zahtevku 18, ali kombinacija za uporabo, kot je zahtevano v zahtevku 19, kjer je drugo farmacevtsko aktivno sredstvo protitelo anti avp6-
  23. 23. Spojina s formulo (II)
    kjer Ri predstavlja atom vodika, metilno skupino ali etilno skupino; R2 predstavlja atom vodika ali atom fluora; R3 predstavlja atom vodika, metilno skupino ali etilno skupino; in R4 je C1 do Ce alkilna skupina; ali sol le-te.
SI201430687T 2013-03-28 2014-03-26 Naftiridinski derivati, uporabni kot antagonisti integrina alfa-v-beta-6 SI2989100T1 (sl)

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GBGB1305668.4A GB201305668D0 (en) 2013-03-28 2013-03-28 Avs6 Integrin Antagonists
EP14712666.8A EP2989100B1 (en) 2013-03-28 2014-03-26 Naphthyridine derivatives useful as alpha-v-beta-6 integrin antagonists
PCT/EP2014/056013 WO2014154725A1 (en) 2013-03-28 2014-03-26 Naphthyridine derivatives useful as alpha-v-beta-6 integrin antagonists

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