HRP20170532T4 - Derivati kromanila za liječenje mitohondrijske bolesti - Google Patents

Derivati kromanila za liječenje mitohondrijske bolesti Download PDF

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HRP20170532T4
HRP20170532T4 HRP20170532TT HRP20170532T HRP20170532T4 HR P20170532 T4 HRP20170532 T4 HR P20170532T4 HR P20170532T T HRP20170532T T HR P20170532TT HR P20170532 T HRP20170532 T HR P20170532T HR P20170532 T4 HRP20170532 T4 HR P20170532T4
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cancer
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HRP20170532TT
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Richard Hendrik Blaauw
Ruben Gerardus George Leenders
Jan Geert Sterk
Pedro Harold Han Hermkens
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Khondrion Ip B.V.
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Publication of HRP20170532T1 publication Critical patent/HRP20170532T1/hr
Publication of HRP20170532T4 publication Critical patent/HRP20170532T4/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/66—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients

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  • Health & Medical Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Engineering & Computer Science (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (20)

1. Spoj opće formule (I): gdje - L je poveznica (linker) koja obuhvaća 1 do 10 po izboru supstituiranih atoma glavnog lanca odabranih između ugljika, dušika i kisika, pri čemu je L odabran između -CH2-CH2-NH-C(O)-CH2-(L2), ili i - R1 i R2 su svaki nezavisno odabrani između vodika i C1 - C6 alkil, ili R1 i R2 su spojeni zajedno da formiraju drugi linker između dušikovog atoma u amidu i kationskog dušikovog atoma, ili R1 je spojen R1' u 4-10 članu cikličnu strukturu i/ili R2 je spojen s R2' u 4-10 članu cikličnu strukturu; i - R3 se odabire između vodika i C1 - C6 alkil, gdje alkilna skupina može biti supstituirana s jednim ili više atoma halogena ili (halo)alkoksi skupinama, ili R3 nije prisutan kada je kationski dušikov atom dio iminske skupine; i - R4 se odabire između vodika i C1 - C6 alkil, gdje alkilni dio može biti supstituiran s jednim ili više atoma halogena ili (halo)alkoksi skupinama; - R5 je spojen s R5' u 4-10 članu cikličnu strukturu i - X- je farmaceutski prikladan anion, gdje spoj nije: (i) spoj formule (I), gdje L = -(CH2)3-(L3), R1 = H, R2 = H, R3 = H, R4 = H i X = Cl; (ii) spoj formule (I), gdje L = -(CH2)3-(L3), R1 = H, R2 = H, R3 = H, R4 = H; X = TFA, koji je S-konfiguracije na položaju 2;
2. Spoj prema zahtjevu 1, gdje X = Cl, I, TFA ili format.
3. Spoj prema bilo kojem od zahtjeva 1-2, gdje - L = -(CH2)2NHC(O)CH2-(L2), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -(CH2)2NHC(NH2)= (L4), R1 = H, R2 = H, R3 = nema, R4 = H; X = TFA; ili - L = -(CH2)2NHC(O)CH2NHC(NH2)= (L5), R1 = H, R2 = H, R3 = nema, R4 = H; X = TFA; ili - L = -(CH2)3NHC(NH2)= (L6), R1 = H, R2 = H, R3 = nema, R4 = H; X = TFA; ili - L = -(CH2)3- (L3), R1 = H, R2 = Me, R3 = Me, R4 = Me; X = I; ili - L = -(CH2)2NHC(Me)= (L7), R1 = H, R2 = H, R3 = nema, R4 = H; X = Cl; ili - L = -(CH2)2NHC(O)CH2NHC(Me)= (L8), R1 = H, R2 = H, R3 = nema, R4 = H; X = Cl; ili - L = -(CH2)3NHC(Me)= (L9), R1 = H, R2 = H, R3 = nema, R4 = H; X = Cl; ili - L = -(CH2)2NR1’C(NH2)= (L10), R1-R1’ = -(CH2)2- (L1), R2 = H, R3 = nema, R4 = H; X = TFA; ili - L = -C(CO2H)(CH2)3- (L11), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -C(CO2H)(CH2)3NHC(NH2)=(L12), R1 = H, R2 = H, R3 = nema, R4 = H; X = Cl; ili - L = -C(CO2H)CH2- (L13), R1 = H,R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -C(CO2H)(CH2)2- (L14), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -C(CO2H)(CH2)3- (L15), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -C(CO2H)(CH2)3- (L11), R1 = H, R2 = Me, R3 = Me, R4 = H; X = Cl; ili - L = -(CH2)4- (L16), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -(CH2)5- (L17), R1 = H, R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -(CH2)4- (L16), R1 = H, R2 = Me, R3 = Me, R4 = H; X = Cl; ili - L = -CHR2’C(O)- (L18), R1 = H, R2-R2’ = -(CH2)3- (L3), R3 = H, R4 = H; X = Cl; ili - L = -CHR2’CH2- (L19), R1 = H, R2-R2’ = -(CH2)3- (L3), R3 = H, R4 = H; X = Cl; ili - L = -CHR5CH2NR5’C(Me)= (L20), R1 = H, R2 = H, R5-R5’ = -(CH2)3- (L3), R3 = nema, R4 = H; X = Cl; ili - L = -CHR2’(CH2)2- (L21), R1 = H, R2-R2’ = -(CH2)2- (L1), R3 = H, R4 = H; X = Cl; ili - L = -(CH2)2CHR1’- (L22), R1-R1’ = -(CH2)2- (L1), R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -(CH2)2CHR1’NHC(O)C(Me)- (L23), R1-R1’ = -(CH2)2- (L1), R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -CH2CHR1’- (L24), R1-R1’ = -(CH2)3- (L3), R2 = H, R3 = H, R4 = H; X = Cl; ili - L = -CH2’CHR1’NHC(Me)= (L25), R1-R1’ = -(CH2)3- (L3), R2’ = H, R3 = nema, R4 = H; X = Cl; ili - L = -CHR5(CH2)2CHR5’- (L26), R1 = H, R2 = H, R5-R5’ = -(CH2)2- (L1), R3 = H, R4 = H; X = Cl; ili - L = -CHR2’CH2- (L19), R1 = H, R2-R2’ = -(CH2)3- (L3), R3 = Me, R4 = H; X = Cl; ili - L = -CHR2’CH2- (L19), R1 = H, R2-R2’ = -(CH2)2- (L1), R3 = H, R4 = H; X = Cl; ili - L = -CHR2’(CH2)2- (L21), R1= H, R2-R2’ = -(CH2)2- (L1), R3 = Me, R4 = H; X = Cl.
4. Spoj prema zahtjevu 3, gdje
5. Spoj prema zahtjevu 3, gdje - L = -(CH2)3-(L3), R1 = H, R2 = Me, R3 = Me, R4 = Me; X = I.
6. Spoj opće formule (I): pri čemu je ili
7. Farmaceutski ili kozmetički pripravak koji sadrži spoj prema bilo kojem od zahtjeva 1 - 6 i fiziološki prikladan nosač.
8. Spoj prema bilo kojem od zahtjeva 1 - 6, za uporabu kao lijek.
9. Spoj prema bilo kojem od zahtjeva 1 - 6, za uporabu u modulaciji barem jednog između morfologije mitohondrija i ekspresije OXPHOS enzima.
10. Spoj za uporabu u liječenju, prevenciji ili suprimiranju simptoma povezanih s mitohondrijskim poremećajem, gdje spoj jest spoj opće formule (I): gdje - L je poveznica (linker) koja obuhvaća 1 do 10 po izboru supstituiranih atoma glavnog lanca odabranih između ugljika, dušika i kisika; pri čemu je L odabran između
ili i - R1 i R2 su svaki nezavisno odabrani između vodika i C1 - C6 alkil, ili R1 i R2 su spojeni zajedno da formiraju drugi linker između dušikovog atoma u amidu i kationskog dušikovog atoma, ili R1 je spojen s R1' u 4-10 članu cikličnu strukturu i/ili R2 je spojen R2' u 4-10 članu cikličnu strukturu; i - R3 se odabire između vodika i C1 - C6 alkil, gdje alkilna skupina može biti supstituirana s jednim ili više atoma halogena ili (halo)alkoksi skupinama, ili R3 nije prisutan kada je kationski dušikov atom dio iminske skupine; i - R4 se odabire između vodika i C1 - C6 alkil, gdje alkilna skupina može biti supstituirana s jednim ili više atoma halogena ili (halo)alkoksi skupinama; i - R5 je spojen s R5' u 4-10 članu cikličnu strukturu - X- je farmaceutski prikladan anion.
11. Spoj za uporabu prema zahtjevu 10, gdje
12. Spoj za uporabu prema zahtjevu 10 ili 11, gdje mitohondrijski poremećaj jest poremećaj odabran iz grupe koju čine: mioklonična epilepsija; mioklonična epilepsija s nepravilnim crvenim vlaknima (MERRF); Leberova nasljedna optička neuropatija (LHON); neuropatska ataksija i retinitis pigmentosa (NARP); mitohondrijska miopatija, encefalomiopatija, laktacidoza i napadi nalik na moždani udar (MELAS); Leigh sindrom; Leigh-sličan sindrom; dominantna optička atrofija (DOA); Kearns-Sayre sindrom (KSS); po majci naslijeđeni dijabetes i gluhoća (MIDD); Alpers-Huttenlocher sindrom; spektar ataksija neuropatija; kronična progresivna eksterna oftalmoplegija (CPEO); Pearson sindrom; mitohondrijska Neuro-Gastro-Intestinalna encefalopatija (MNGIE); Sengers sindrom; 3-metilglutakonatna acidurija, senzorineuralna gluhoća, encefalopatija i neuroradiološki nalazi Leigh-sličnog sindroma (MEGDEL); miopatija; mitohondrijska miopatija; kardiomiopatija; i encefalomiopatija, SURFS1 (COX deficijentan Leigh sindrom zbog deficijencije zasićenog proteina kompleksa IV) i izolirane ili kombinirane OXPHOS deficijencije sa do sada neriješenim genetičkim defektom uključujući poremećenu oksidaciju piruvata i ATP plus PCr brzine proizvodnje.
13. Spoj prema bilo kojem od zahtjeva 3 - 6, za uporabu u liječenju, prevenciji ili suprimiranju simptoma povezanih sa stanjem povezanim s disfunkcijom mitohondrija, gdje, poželjno spoj jest spoj prema zahtjevu 5.
14. Spoj za uporabu prema zahtjevu 13, gdje je stanje povezano s disfunkcijom mitohondrija stanje odabrano iz grupe koju čine: Friedreichova ataksija (FRDA); renalna tubularna acidoza; Parkinsonova bolest; Alzheimerova bolest; amiotrofična lateralna skleroza (ALS); Huntingtonova bolest; razvojni pervazivni poremećaji; gubitak sluha; gluhoća; dijabetes; starenje; i nuspojave lijekova koje utječu na funkciju mitohondrija.
15. Spoj za uporabu prema bilo kojem od zahtjeva 10 - 14, gdje se koristi mjerljivi klinički marker za procjenu učinkovitosti liječenja spojem prema pronalasku.
16. Spoj za uporabu prema zahtjevu 15, gdje klinički marker jest jedan ili više markera odabranih iz grupe koju čine razine mliječne kiseline (laktat), bilo iz pune krvi, plazme, cerebrospinalne tekućine, ili cerebralne ventrikularne tekućine; razine piruvatne kiseline (piruvat), bilo iz pune krvi, plazme, cerebrospinalne tekućine, ili cerebralne ventrikularne tekućine; omjeri laktata/piruvata, bilo iz pune krvi, plazme, cerebrospinalne tekućine, ili cerebralne ventrikularne tekućine; aminokiseline, posebno alanin, citrulin i prolin u punoj krvi, plazmi ili cerebrospinalnoj tekućini, organske kiseline u tjelesnim tekućinama; FGF21 u serumu i mišićima skeleta; razine fosfokreatina, razine NADH (NADH + H+) ili NADPH (NADPH + H+); razine NAD ili NADP; razine ATP; anaerobna granica; smanjene razine koenzima Q (CoQred); razine oksidiranog koenzima Q (CoQox; ukupne razine koenzima Q (CoQtot); razine oksidiranog citokroma C; smanjene razine citokroma C; omjer oksidiranog citokroma C/reduciranog citokroma C; razine acetoacetata, razine beta-hidroksi butirata, omjer acetoacetat/betahidroksi butirat, razine 8-hidroksi-2’-deoksigvanozina (8-OHdG); razine reaktivnih kisikovih skupina; i razine potrošnje kisika (VO2), razine proizvodnje ugljikovog dioksida (VCO2), i respiratorni kvocijent (VCO2/VO2).
17. Spoj za uporabu u liječenju, prevenciji ili suprimiranju simptoma povezanih s neoplastičnom bolesti, gdje spoj jest spoj opće formule (I): gdje - L = -(CH2)3-(L3), R1 = H, R2 = Me, R3 = Me, R4 = Me; X = I; ili - L = -(CH2)2- (L1), R1 = H, R2 = Me, R3 = Me, R4 = Me; X = I.
18. Spoj za uporabu prema zahtjevu 17, gdje je neoplastična bolest rak, poželjno rak odabran iz grupe koju čini karcinom bazalnih stanica, rak kostiju, rak crijeva, rak mozga, rak dojke, rak cerviksa, leukemija, rak jetre, rak pluća, limfom, melanom, rak jajnika, rak gušterače, rak prostate ili rak štitnjače.
19. Kozmetički postupak za liječenje ili odgađanje daljnjeg starenja kože u subjekta, postupak obuhvaća korak primjene učinkovite količine pripravka koji sadrži spoj opće formule (I) na kožu subjekta: gdje - L je poveznica (linker) koja obuhvaća 1 do 10 po izboru supstituiranih atoma glavnog lanca odabranih između ugljika, dušika i kisika; i - R1 i R2 su svaki nezavisno odabrani između vodika i C1 - C6 alkil, ili R1 i R2 su spojeni zajedno da formiraju drugi linker između dušikovog atoma u amidu i kationskog dušikovog atoma, ili R1 je spojen s atomom glavnog lanca linkera L u cikličku strukturu i/ili R2 je spojen s atomom glavnog lanca linkera L u cikličku strukturu; i - R3 se odabire između vodika i C1 - C6 alkil, gdje alkilna skupina može biti supstituirana s jednim ili više atoma halogena ili (halo)alkoksi skupinama, ili R3 nije prisutan kada je kationski dušikov atom dio iminske skupine; i - R4 se odabire između vodika i C1 - C6 alkil, gdje alkilna skupina može biti supstituirana s jednim ili više atoma halogena ili (halo)alkoksi skupinama; i - X- je farmaceutski prikladan anion.
20. Postupak prema zahtjevu 19, gdje
HRP20170532TT 2012-07-12 2017-04-03 Derivati kromanila za liječenje mitohondrijske bolesti HRP20170532T4 (hr)

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US201261670644P 2012-07-12 2012-07-12
EP12176128 2012-07-12
EP13759838.9A EP2872497B2 (en) 2012-07-12 2013-07-12 Chromanyl derivatives for treating mitochondrial disease
PCT/NL2013/050528 WO2014011047A1 (en) 2012-07-12 2013-07-12 Chromanyl derivatives for treating mitochondrial disease

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MX2020005238A (es) * 2017-11-22 2020-08-24 Khondrion Ip B V Compuestos novedosos como inhibidores mpges-1.
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CA3127590A1 (en) 2019-01-28 2020-08-06 Mitochondria Emotion, Inc. Mitofusin activators and methods of use thereof
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