HRP20161079T1 - Selektivni inhibitori glikozidaze i njihove uporabe - Google Patents

Selektivni inhibitori glikozidaze i njihove uporabe Download PDF

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HRP20161079T1
HRP20161079T1 HRP20161079TT HRP20161079T HRP20161079T1 HR P20161079 T1 HRP20161079 T1 HR P20161079T1 HR P20161079T T HRP20161079T T HR P20161079TT HR P20161079 T HRP20161079 T HR P20161079T HR P20161079 T1 HRP20161079 T1 HR P20161079T1
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Croatia
Prior art keywords
pyrano
tetrahydro
thiazol
diol
fluoro
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HRP20161079TT
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English (en)
Inventor
Ramesh Kaul
Ernest J. Mceachern
Changwei Mu
Harold G. Selnick
David J. Vocadlo
Yaode Wang
Zhongyong Wei
Yuanxi Zhou
Yongbao Zhu
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Alectos Therapeutics Inc.
Merck Sharp & Dohme Corp.
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Priority claimed from PCT/CN2011/074569 external-priority patent/WO2012159262A1/en
Application filed by Alectos Therapeutics Inc., Merck Sharp & Dohme Corp. filed Critical Alectos Therapeutics Inc.
Publication of HRP20161079T1 publication Critical patent/HRP20161079T1/hr

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Claims (14)

1. Spoj formule (I) ili njegova farmaceutski prihvatljiva sol: [image] u kojem R1 i R2 su H, ili R1 je H i R2 je F, ili R1 je F i R2 je H, ili R1 je OR3 i R2 je H; svaki R3 je nezavisno H ili C1-6acil; R4 je H i R5 je OR3, ili R4 je OR3 i R5 je H; R6 je H, F ili OR3; svaki R7 je nezavisno H ili F; svaki R8 je nezavisno izabran iz grupe koja se sastoji od: H, C1-6 alkil, C3-6 alkenil, C3-6 alkinil i C1-6 alkoksi, gdje su C1-6 alkil, C3-6 alkenil, C3-6 alkinil ili C1-6 alkoksi izborno supstituirani od jednog do maksimalnog broja supstituenata sa jednim ili više od fluoro, OH, ili metil, ili dvije R8 grupe su povezane sa atomom dušika za koji su vezane tako da formiraju prsten, pri čemu je navedeni prsten izborno nezavisno supstituiran od jednog do maksimalnog broja supstituenata sa jedim ili više od fluoro, OH ili metil, uz uvjet da kada R6 je OR3, svaki R7 je H; i uz uvjet da se R1 ili R6 razlikuje od OR3.
2. Spoj prema patentnom zahtjevu 1 u kojem: (i) R1 i R2 su H, ili R1 je H i R2 je F, ili R1 je F i R2 je H, ili R1 je OH i R2 je H; R4 je H; R5 je OH; R6 je H ili OH; i svaki R8 je nezavisno izabran iz grupe koja se sastoji od: H, CH3, CH2CH3, (CH2)2CH3, CH2CH=CH2 i CH2C≡CH ili NR82 je azetidin-1-il, uz uvjet da kada R6 je OH, svaki R7 je H; uz uvjet da se R1 ili R6 razlikuje od OH; ili (ii) najmanje jedan od R1, R2, R6 i R7 je F.
3. Spoj prema patentnom zahtjevu 1 naznačen time što spoj je spoj formule (Ia) ili njegova farmaceutski prihvatljiva sol: [image] gdje R1 i R2 su H i R6 je F; ili R1 je H i R2 je F i R6 je H, F, ili OR3; ili R1 je F i R2 je H i R6 je H, F ili OR3; ili R1 je OR3 i R2 je H i R6 je F; svaki R3 je nezavisno H ili C1-6 acil; svaki R7 je nezavisno H ili F; svaki R8 je nezavisno izabran iz grupe koja se sastoji od: H, C1-6 alkil, C3-6 alkenil, C3-6 alkinil i C1-6 alkoksi, gdje su C1-6 alkil, C3-6 alkenil, C3-6 alkinil ili C1-6 alkoksi izborno supstituirani sa od jednog do maksimalnog broja supstituenata sa jednim ili više od fluoro, OH ili metil, ili dvije R8 grupe su vezane zajedno sa atomom dušika za koji su vezane tako da formiraju prsten, pri čemu je navedeni prsten izborno nezavisno supstituiran sa od jednog do maksimalnog broja supstituenata sa jednim ili više od fluoro, OH ili metil, uz uvjet da kada R6 je OR3, svaki R7 je H.
4. Spoj prema patentnom zahtjevu 1 naznačen time što spoj je: (3aR,5R,6S,7R,7aR)-2-(etilamino)-5-metil-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5R,6S,7aR)-2-(etilamino)-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-2-(dimetilamino)-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-2-amino-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-2-(etilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-2-(dimetilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano [3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-2-(etilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(dimetilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(alilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-amino-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(azetidin-1-il)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(alilamino)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-amino-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(prop-2-yn-1-ilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(azetidin-1-il)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5R,6S,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-7-fluoro-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7S,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-2-(etilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-2-(dimetilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(isobutilamino)-5,6,7,7a-tetrahidro-3aH-pirano [3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-7-fluoro-2-(((E)-3-fluoro-2-metilalil)amino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-((4-hidroksibut-2-yn-1-il)amino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7aR)-2-((2,2-difluoroetoksi)(metil)amino)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7S,7aR)-7-fluoro-2-(3-fluoroazetidin-1-il)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; ili (3aR,5R,6S,7S,7aR)-2-(3,3-difluoroazetidin-1-il)-7-fluoro-5-metil-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol, ili farmaceutski prihvatljiva sol bilo kojeg od gore navedenih spojeva.
5. Spoj prema patentnom zahtjevu 1 naznačen time što spoj je: (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; ili (3aR,5S,6R,7S,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; ili farmaceutski prihvatljiva sol bilo kojeg od gore navedenih spojeva.
6. Farmaceutska kompozicija koja sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 5 ili njegovu farmaceutski prihvatljivu sol u kombinaciji sa farmaceutski prihvatljivim nosačem.
7. Spoj formule (I) ili njegova farmaceutski prihvatljiva sol prema jednom ili više od patentnih zahtjeva 1 do 5 za uporabu u liječenju stanja koje je: inflamatorna bolest, alergija, astma, alergijski rinitis, bolesti hipersenzitivnosti pluća, hipersenzitivan pneumonitis, eozinofilne pneumonije, hipersenzitivnost odgođenog tipa, ateroskleroza, intersticijalna bolest pluća (ILD), idiopatska bolest pluća, ILD povezan sa reumatoidnim artritisom, sustavni lupus eritematodes, ankilozni spondilitis, sustavna skleroza, Sjogrenov sindrom, polimiozitis ili dermatomiozitis, sustavna anafilaksa ili odgovor hipersenzitivnosti, alergije na lijekove, alergija na ubod insekata, autoimuna bolest, reumatoidni artritis, psorijatski artritis, multipla skleroza, Guillain-Barré sindrom, sustavni lupus eritematodes, miastenija gravis, glomerulonefritis, autoimuni tiroiditis, odbacivanje transplanta, odbacivanje alo-transplanta, bolest transplanta protiv domaćina, inflamatorna bolest crijeva, Kronova bolest, ulcerozni kolitis, spondiloartropatija, skleroderma, psorijaza, T-stanično posredovana psorijaza, inflamatorni dermatozis, dermatitis, ekcem, atopijski dermatitis, alergijski kontaktni dermatitis, urtikarija, vaskulitis, nekrotizujući, kutani i hipersenzitivni vaskulitis, eozinofilni miotis, eozinofilni fasciitis, odbacivanje transplanta solidnog organa, odbacivanje transplanta srca, odbacivanje transplanta pluća, odbacivanje transplanta jetre, odbacivanje transplanta bubrega, odbacivanje transplanta pankreasa, alografta bubrega, alografta pluća, epilepsija, bol, fibromialgija, moždani udar ili neuroprotekcija.
8. Spoj formule (I) ili njegova farmaceutski prihvatljiva sol prema jednom ili više patentnih zahtjeva 1 do 5 za uporabu u liječenju stanja koje je izabrano iz grupe koja se sastoji od neurodegenerativne bolesti, tauopatije, kancera i stresa, kod subjekta kod kojeg postoji potreba za istim.
9. Spoj za upotrabu prema patentnom zahtjevu 8 gdje je stanje: (i) Alzheimerova bolest, amiotrofna lateralna skleroza (ALS), amiotrofna lateralna skleroza sa kognitivnim oštećenjem (ALSci), demencija sa argirofilnim zrnima, Bluit-ova bolest, kortikobazalna degeneracija (CBD), Dementia pugilistica, difuzni neurofibrilarni čvorovi sa kalcifikacijom, Daunov sindrom, porodična britanska demencija, porodična danska demencija, frontotemporalna demencija sa parkinsonizmom povezanim za kromosomom 17 (FTDP-17), Gerstmann-Straussler-Scheinker-ova bolest, Guadeloupean-ov parkinsonizam, Hallevorden-Spatz-ova bolest (neurodegeneracija sa akumulacijom željeza u mozgu tipa 1), multipla sustavna atrofija, miotonična distrofija, Niemann-Pick-ova bolest (tip C), Palido-ponto-nigralna degeneracija, Guamov kompleks parkinsonizma-demencije, Pickova bolest (PiD), post-encefalitički parkinsonizam (PEP), Prionske bolesti (uključujući Creutzfeldt-Jakobovu bolest (CJD), varijantnu Creutzfeldt-Jakobovu bolest (vCJD), fatalnu porodičnu insomniju i kuru), progresivna superkortikalna glioza, progresivna supranuklearna paraliza (PSP), Richardson-ov sindrom, subakutni sklerotizujući panencefalitis, „tangle-only“ demencija, Huntington-ova bolest, Parkinson-ova bolest, šizofrenija, blago kognitivno oštećenje (MCI), neuropatija (uključujući perifernu neuropatiju, autonomnu neuropatiju, neuritis i dijabetičku neuropatiju) ili glaukom; (ii) stres, gdje je stres srčani poremećaj; (iii) stres, gdje je stres srčani poremećaj i gdje je srčani poremećaj: ishemija; krvarenje; hipovolemijski šok; infarkt miokarda; intervencijska kardiološka procedura; operacija srčanog bypass-a; fibrinolitička terapija; angioplastika; ili postavljanje stenta.
10. Spoj za uporabu prema patentnom zahtjevu 8 naznačen time što je stanje Alzheimerova bolest (AD).
11. Spoj za uporabu prema patentnom zahtjevu 8 naznačen time što je stanje progresivna supranuklearna paraliza (PSP).
12. Spoj za uporabu prema bilo kojem od patentnih zahtjeva 7 do 11 naznačen time što spoj je: (3aR,5R,6S,7R,7aR)-2-(etilamino)-5-metil-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5R,6S,7aR)-2-(etilamino)-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-2-(dimetilamino)-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-2-amino-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6S,7aR)-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-2-(etilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-2-(dimetilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-2-(etilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(dimetilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(alilamino)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-amino-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(azetidin-1-il)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(alilamino)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-amino-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(prop-2-yn-1-ilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-2-(azetidin-1-il)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5R,6S,7R,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-7-fluoro-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano [3,2-d]tiazol-6-ol; (3aR,5S,6R,7S,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano [3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-2-(etilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-2-(dimetilamino)-7-fluoro-5-(hidroksimetil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(propilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(isobutilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7R,7aR)-5-(difluorometil)-7-fluoro-2-(((E)-3-fluoro-2-metilalil)amino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-((4-hidroksibut-2-yn-1-il)amino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7aR)-2-((2,2-difluoroetoksi)(metil)amino)-5-(difluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6R,7S,7aR)-7-fluoro-2-(3-fluoroazetidin-1-il)-5-(fluorometil)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; ili (3aR,5R,6S,7S,7aR)-2-(3,3-difluoroazetidin-1-il)-7-fluoro-5-metil-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol, ili farmaceutski prihvatljiva sol bilo kojeg od gore navedenih spojeva.
13. Spoj za uporabu prema bilo kojem od patentnih zahtjeva 7 do 11 naznačen time što spoj je: (3aR,5R,6R,7S,7aR)-7-fluoro-5-(hidroksimetil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; (3aR,5S,6S,7R,7aR)-5-(fluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(etilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(dimetilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; (3aR,5S,6S,7R,7aR)-5-(difluorometil)-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6,7-diol; ili (3aR,5S,6R,7S,7aR)-5-(difluorometil)-7-fluoro-2-(metilamino)-5,6,7,7a-tetrahidro-3aH-pirano[3,2-d]tiazol-6-ol; ili farmaceutski prihvatljiva sol bilo kojeg od gore navedenih spojeva.
14. Spoj za uporabu prema bilo kojem od patentnih zahtjeva 7 do 13 naznačen time što subjekt je čovjek.
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CN103339138B (zh) 2016-08-31
CA2822493C (en) 2018-11-20
MX2013007434A (es) 2013-10-03
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US20160096858A1 (en) 2016-04-07
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