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HRP20221112T1 - Derivati benzodiazepina kao inhibitori rsv - Google Patents

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Publication number
HRP20221112T1
HRP20221112T1 HRP20221112TT HRP20221112T HRP20221112T1 HR P20221112 T1 HRP20221112 T1 HR P20221112T1 HR P20221112T T HRP20221112T T HR P20221112TT HR P20221112 T HRP20221112 T HR P20221112T HR P20221112 T1 HRP20221112 T1 HR P20221112T1
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optionally substituted
compound according
alkyl
pharmaceutically acceptable
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HRP20221112TT
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Brian C. Shook
In Jong Kim
Thomas P. Blaisdell
Jianming Yu
Joseph PANARESE
Yat Sun Or
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Enanta Pharmaceuticals, Inc.
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Publication of HRP20221112T1 publication Critical patent/HRP20221112T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
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    • 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
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • 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
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Claims (23)

1. Spoj predstavljen formulom (I): [image] ili njegova farmaceutski prihvatljiva sol, pri čemu: R1 je odabran iz skupine koju čine: 1) vodik; 2) halogen; 3) CN; 4) izborno supstituirani -C1-C8 alkil; i 5) izborno supstituirani -C1-C8 alkil -O-R11; R2 i R5 su svaki neovisno odabrani iz skupine koju čine: 1) vodik; i 2) izborno supstituirani - C1-C8 alkil; A se bira iz grupe koju čine: 1) izborno supstituirani heteroaril 2) izborno supstituirani -C3-C12 cikloalkil; 3) izborno supstituirani -C3-C12 cikloalkenil; 4) izborno supstituirani aril; R3 je vodik ili R11; R4 je odabran iz skupine koju čine: 1) izborno supstituirani -C3-C12 cikloalkil; 2) izborno supstituirani -C3-C12 cikloalkenil; 3) izborno supstituirani 3- do 12-eročlani heterociklil; 4) izborno supstituirani aril; 5) izborno supstituirani heteroaril; 6) Izborno supstituirani aril-O-; 7) izborno supstituirani heteroaril-O; 8) izborno supstituirani aril-C1-C4-alkil; i 9) izborno supstituirani heteroaril-C1-C4-alkil; svaki R6 je isti ili različit i neovisno odabran između vodika, halogena, hidroksila, zaštićenog hidroksila, cijano, amino, zaštićenog amino, nitro, izborno supstituiranog - C1-C8 alkila, izborno supstituiranog -C1-C8 alkoksi, izborno supstituiranog -NHC1-C8 alkil, izborno supstituirani -S-(-C1-C8 alkil), izborno supstituirani -SO2-(-C1-C8 alkil), - izborno supstituirani -SO2-NH-(-C1-C8 alkil), izborno supstituirani -NH- SO2-(-C1-C8 alkil), -CO2R12-NR13R14 i -CO-NR13R14; R11 i R12 su svaki neovisno odabrani iz skupine koju čine: 1) izborno supstituirani -C1-C8 alkil; 2) izborno supstituirani -C2-C8 alkenil; 3) izborno supstituirani -C2-C8 alkinil; 4) izborno supstituirani -C3-C8 cikloalkil; 5) izborno supstituirani -C3-C8 cikloalkenil; 6) izborno supstituirani 3- do 8-člani heterocikloalkil; 7) izborno supstituirani aril; i 8) izborno supstituirani heteroaril; R13 i R14 su svaki neovisno odabrani između vodika, izborno supstituiranog C1-C8-alkila, izborno supstituiranog -C2-C8-alkenila, izborno supstituiranog -C2-C8-alkinila; izborno supstituirani -C3-C8-cikloalkil, -C(O)R12, -S(O)2R12, i -S(O)2NHR12, i izborno supstituiran - C1-C8-alkoksi; alternativno, R13 i R14 su uzeti zajedno s dušikom koji su vezali da tvore heterociklički prsten; i n je 0, 1, 2, 3 ili 4.
2. Spoj prema zahtjevu 1, predstavljen formulom (Ib), [image] ili njegova farmaceutski prihvatljiva sol.
3. Spoj prema zahtjevu 1, naznačen time što je A odabran između jednog od sljedećeg uklanjanjem dva atoma vodika: [image] [image] [image] [image] pri čemu je svaki od gore prikazanih izborno zamijenjen kada je to moguće.
4. Spoj prema zahtjevu 1, naznačen time što je R4 odabran između jednog od sljedećeg uklanjanjem jednog atoma vodika: [image] [image] [image] [image] [image] pri čemu je svaki od gore prikazanih izborno zamijenjen kada je to moguće.
5. Spoj prema zahtjevu 1, naznačen time što je R4 izborno supstituiran s jednim, dva ili tri od sljedećih supstituenata: halo, -CH3, -CF3, -OCF3, -CN, -NH2, -OH, -CH2N(CH3)2, -C(O)CH3, izborno supstituirani -NH-(C1-C6)alkil, izborno supstituirani -NH -(C1-C6)alkil-(C1-C6)alkoksi, izborno supstituiran -SO2-(C1-C6)alkil, izborno supstituiran -SO2-NH-(C1-C6)alkil, izborno supstituiran -NH-SO2-(C1-C6)alkil, izborno supstituirani 3- do 12-člani heterocikloalkil, izborno supstituirani aril, izborno supstituirani heteroaril, izborno supstituiran - C1-C8-alkil, izborno supstituiran - C1-C8-alkenil, izborno supstituiran - C3-C8-cikloalkil, izborno supstituiran - C3-C8-cikloalkenil, i izborno supstituiran - C1-C8-alkoksi.
6. Spoj prema zahtjevu 1 naznačen time što je R4 izborno supstituiran s jednim ili dva ili tri od sljedećih supstituenata: CH3, CN, fluoro, kloro, CH3O-, CH3C(O)-, CH3OCH2-, CH3OCH2CH2O-, -CF3, CF3O-, [image] [image] [image] [image] [image]
7. Spoj prema zahtjevu 1, predstavljen formulom (IIa-1), (IIa-2), (IIb-1) ili (IIb-2), ili njegova farmaceutski prihvatljiva sol, [image] [image] pri čemu su R2, R3, R4, R5, R6, n i A kako je definirano u zahtjevu 1.
8. Spoj prema zahtjevu 1, predstavljen formulom (IV-1), (IV-2), (IV-3), ili (IV-4), ili njegova farmaceutski prihvatljiva sol, [image] [image] pri čemu su R1, R2, R3, R4, R5, R6, i n definirani kao u zahtjevu 1.
9. Spoj prema zahtjevu 1, predstavljen formulom (V-1), (V-2), (V-3) ili (V-4), [image] [image] ili njegova farmaceutski prihvatljiva sol, pri čemu su R1, R2, R3, R4, R5, R6, i n definirani kao u zahtjevu 1.
10. Spoj prema zahtjevu 1, predstavljen jednom od formula (VIa-1) do (VIb-8), [image] [image] [image] [image] [image] [image] [image] [image] ili njegova farmaceutski prihvatljiva sol, pri čemu R4 i R6 su kao što je definirano u zahtjevu 1.
11. Spoj prema zahtjevu 10 naznačen time što je R4 odabran iz skupina navedenih u donjoj tablici, od kojih je svaka izborno supstituirana: [image] [image] [image] [image] [image] [image]
12. Spoj odabran od dolje navedenih spojeva ili njegova farmaceutski prihvatljiva sol: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image]
13. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
14. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
15. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
16. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
17. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
18. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
19. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
20. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
21. Spoj prema zahtjevu 12 ima strukturu [image] ili njegova farmaceutski prihvatljiva sol.
22. Farmaceutski pripravak, sadrži spoj prema bilo kojem od zahtjeva 1 do 21, ili njegovu farmaceutski prihvatljivu sol, u kombinaciji s farmaceutski prihvatljivim nosačem, razrjeđivačem ili ekscipijensom.
23. Spoj prema bilo kojem od zahtjeva 1 do 21 za uporabu u liječenju ili prevenciji infekcije respiratornim sincicijskim virusom.
HRP20221112TT 2015-07-22 2016-07-21 Derivati benzodiazepina kao inhibitori rsv HRP20221112T1 (hr)

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US201562195648P 2015-07-22 2015-07-22
US201662335227P 2016-05-12 2016-05-12
EP16828528.6A EP3324977B1 (en) 2015-07-22 2016-07-21 Benzodiazepine derivatives as rsv inhibitors
PCT/US2016/043320 WO2017015449A1 (en) 2015-07-22 2016-07-21 Benzodiazepine derivatives as rsv inhibitors

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