HRP20201068T1 - Piridini supstituirani heteroarilom i postupci njihove upotrebe - Google Patents

Piridini supstituirani heteroarilom i postupci njihove upotrebe Download PDF

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HRP20201068T1
HRP20201068T1 HRP20201068TT HRP20201068T HRP20201068T1 HR P20201068 T1 HRP20201068 T1 HR P20201068T1 HR P20201068T T HRP20201068T T HR P20201068TT HR P20201068 T HRP20201068 T HR P20201068T HR P20201068 T1 HRP20201068 T1 HR P20201068T1
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pyridin
sulfonyl
benzene
trifluoromethoxy
independently selected
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Robert J. Altenbach
Andrew Bogdan
Ghjuvanni Petru Diunisu COTI
Marlon D. Cowart
Stephen N GRESZLER
Hans KELGTERMANS
Philip R. Kym
Steven Emiel Van Der Plas
Xueqing Wang
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AbbVie Overseas S.à r.l.
Galapagos Nv
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    • 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
    • C07D413/14—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
    • 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
    • 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
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
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    • 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
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    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • 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

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Claims (19)

1. Spoj Formule I, ili njegova farmaceutski prihvatljiva sol [image] , naznačen time što X1 i X2 su neovisno birani H; halogen; C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih halogena; C1-4 alkoksi, koji može biti supstituiran s jednim ili više neovisno biranih -OH; C1-4 alkoksi; ili -NR8AR8B; -NR9AR9B; ciklopropil, koji može biti supstituiran s jednom ili više neovisno biranih skupina R5; fenoksi, koji može biti supstituiran s jednom ili više neovisno biranih skupina R5; ili fenil, koji može biti supstituiran s jednom ili više neovisno biranih skupina R5; R1 je C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih -OH; C1-4 alkoksi; ili 4-6-eročlanih monocikličkih heterocikla koji sadrže 1 ili 2 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; fenil, koji može biti supstituiran s jednim ili više neovisno biranih R4 skupine; N-vezani 4-6-eročlani monociklički heterocikl koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine N, O i S, gdje heterocikl može biti supstituiran s jednom ili više neovisno biranih skupina R5; N-vezani 4-6-eročlani monociklički heterocikl koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine N, O i S, kondenziran s fenilom, gdje monociklički heterocikl i fenil mogu biti supstituirani s jednom ili više neovisno biranih skupina R5; C3-7 cikloalkil, koji može biti supstituiran s jednom ili više neovisno biranih skupina R5; ili -NR6R7; R2 je 5-6-eročlani monociklički heteroaril koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N, gdje monociklički heteroaril može biti supstituiran s jednom ili više neovisno biranih skupina R3; svakog R3 se neovisno bira iz skupine koju čine: C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih C3-7 cikloalkila; gdje C3-7 cikloalkil može biti supstituiran s jednom ili više neovisno biranih skupina RA; 4-6-eročlanih monocikličkih heterocikla koji sadrže 1 ili 2 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heterocikl može biti supstituiran s jednom ili više neovisno biranih skupina RA; fenila; gdje fenil može biti supstituiran s jednom ili više neovisno biranih skupina RA; C1-4 alkoksi, koji mogu biti supstituirani s jednim ili više neovisno biranih C3-7 cikloalkila, halogena ili -OCH3; -OR11; -OH; halogena; -CN; -OC(O)R10; -OS(O)2OH; -NHC(=S)R11; ili -OP(O)(OH)(OH); -C(O)NH2; fenil; gdje fenil može biti supstituiran s jednom ili više neovisno biranih skupina RA; 5-6-eročlani monociklički heteroaril koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heteroaril može biti supstituiran s jednom ili više neovisno biranih skupina RA; C3-7 cikloalkil; gdje C3-7 cikloalkil može biti supstituiran s jednom ili više neovisno biranih skupina RA; i 4-6-eročlani monociklički heterocikl koji sadrži 1 ili 2 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heterocikl može biti supstituiran s jednom ili više neovisno biranih skupina RA; svakog R4 se neovisno bira iz skupine koju čine: halogen; C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih halogena; i C1-4 alkoksi, koji može biti supstituiran s jednim ili više neovisno biranih halogena; svakog R5 se neovisno bira iz skupine koju čine: -OH; halogen; C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih C1-4 alkoksi, halogena ili -OH; i C1-4 alkoksi, koji može biti supstituiran s jednim ili više neovisno biranih halogena; R6 je H, C1-4 alkil ili C3-7 cikloalkil, gdje C3-7 cikloalkil može biti supstituiran s jednom ili više neovisno biranih skupina R5; R7 je C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih halogena; fenila, koji mogu biti supstituirani s jednim ili više neovisno biranih halogena; C1-4 alkila, koji mogu biti supstituirani s jednim ili više neovisno biranih halogena; ili C1-4 alkoksi, koji mogu biti supstituirani s jednim ili više neovisno biranih halogena; C1-4 alkoksi, koji mogu biti supstituirani s jednim ili više neovisno biranih halogena; ili 4-6-eročlanih monocikličkih heterocikla koji sadrže 1 ili 2 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heterocikl može biti supstituiran s jednom ili više neovisno biranih skupina R5; svakog R8a i R8b se neovisno bira iz skupine koju čine H; i C1-4 alkil; R9a i R9b se neovisno bira iz skupine koju čine H; C1-4 alkil; i C3-7 cikloalkil; i svakog R10 se neovisno bira iz skupine koju čine C1-6 alkil; i fenil; gdje fenil može biti supstituiran s jednom ili više neovisno biranih skupina RA; svakog R11 se neovisno bira iz skupine koju čine 4-6-eročlani monociklički heterocikl koji sadrži 1 ili 2 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heterocikl može biti supstituiran s jednom ili više neovisno biranih skupina RA; 5-6-eročlani monociklički heteroaril koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N; gdje monociklički heteroaril može biti supstituiran s jednom ili više neovisno biranih skupina RA; C3-7 cikloalkil; gdje C3-7 cikloalkil može biti supstituiran s jednom ili više neovisno biranih skupina RA; i fenil; gdje fenil može biti supstituiran s jednom ili više neovisno biranih skupina RA; i svakog RA se neovisno bira iz skupine koju čine -CN, halogen; C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih halogena; i C1-4 alkoksi, koji može biti supstituiran s jednim ili više neovisno biranih halogena.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R1 fenil, koji može biti supstituiran s jednom neovisno biranom skupinom R4.
3. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R1 fenil supstituiran s jednim -OCF3.
4. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je svaki od X1 i X2 H.
5. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R2 5-6-eročlani monociklički heteroaril koji sadrži 1, 2 ili 3 heteroatoma, koje se neovisno bira iz skupine koju čine O, S i N, gdje monociklički heteroaril može biti supstituiran s jednom skupinom R3.
6. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R2 1,3,4-oksadiazolil, 1,2,4-oksadiazolil, 1,3,4-tiadiazolil ili tiazolil, gdje su 1,3,4-oksadiazolil, 1,2,4-oksadiazolil, 1,3,4-tiadiazolil, te tiazolil supstituirani s jednim neovisno biranim R3.
7. Spoj u skladu s patentnim zahtjevom 5, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R3 C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih -OH; halogena; ili -OP(O)(OH)(OH).
8. Spoj u skladu s patentnim zahtjevom 6, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R3 C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih -OH; halogena; ili -OP(O)(OH)(OH).
9. Spoj u skladu s patentnim zahtjevom 1 Formule I-a, ili njegova farmaceutski prihvatljiva sol [image] , naznačen time što n je 0, 1 ili 2; R4A je H, F, -CH3, -CH(CH3)2, t-Bu, CF3, -OCH3, -OCH(CH3)2 ili -OCF3; svaki R4B je neovisno F ili -OCF3; i X1 i R2 su kao što je iznijeto u patentnom zahtjevu 1.
10. Spoj u skladu s patentnim zahtjevom 9, ili njegova farmaceutski prihvatljiva sol, naznačen time što je X1 H.
11. Spoj u skladu s patentnim zahtjevom 9, ili njegova farmaceutski prihvatljiva sol, naznačen time što n je 0; i R4A je -OCF3.
12. Spoj u skladu s patentnim zahtjevom 9, ili njegova farmaceutski prihvatljiva sol, naznačen time što X1 je H; n je 0; R4A je -OCF3; R2 je 1,3,4-oksadiazolil ili tiazolil supstituiran s jednim R3; i R3 je C1-4 alkil, koji može biti supstituiran s jednim ili više neovisno biranih -OH; halogena; ili -OP(O)(OH)(OH).
13. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što se spoj bira iz skupine koju čine: (5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metil-dihidrogenfosfat; 2-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)-1,1,1-trifluorpropan-2-ol; 1-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)-2,2,2-trifluoretan-1-ol; (2-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3-tiazol-5-il)metanol; 2-(1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; (5-{3-amino-5-[4-(trifluormetil)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; 5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-karboksamid; {5-[3-amino-5-(4-fluorbenzen-1-sulfonil)piridin-2-il]-1,3,4-oksadiazol-2-il}metanol; 2-(5-cikloheksil-1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(S)-metoksi(fenil)metil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(ciklopropilmetoksi)metil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(fenoksimetil)-1,3,4-oksadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(ciklopentiloksi)metil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 5-[4-(trifluormetoksi)benzen-1-sulfonil]-2-{5-[(trifluormetoksi)metil]-1,3,4-oksadiazol-2-il}piridin-3-amin; 2-(5-{[(oksolan-3-il)oksi]metil}-1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(2-metoksietoksi)metil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; N-[(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-tiadiazol-2-il)metil]ciklopropankarbotioamid; 2-{5-[(S)-metoksi(fenil)metil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; (2S)-2-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-tiadiazol-2-il)-1,1,1-trifluorpropan-2-ol; 2-{5-[(1R)-1-metoksietil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(1-metoksietil)-1,3,4-tiadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(1S)-1-metoksietil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(ciklopropilmetoksi)metil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(etoksimetil)-1,3,4-tiadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(metoksimetil)-1,3,4-tiadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(piridin-3-il)oksi]metil}-1,3,4-tiadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 5-[4-(trifluormetoksi)benzen-1-sulfonil]-2-{5-[(trifluormetoksi)metil]-1,3,4-tiadiazol-2-il}piridin-3-amin; 2-(5-{[(oksolan-3-il)oksi]metil}-1,3,4-tiadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(difluormetoksi)metil]-1,3,4-tiadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(2S)-oksolan-2-il]metil}-1,3,4-tiadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(2R)-oksolan-2-il]metil}-1,3,4-tiadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(2-metoksietoksi)metil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(1R)-1-metoksietil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(1S)-1-metoksietil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(etoksimetil)-1,3,4-oksadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[5-(metoksimetil)-1,3,4-oksadiazol-2-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(piridin-3-il)oksi]metil}-1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{5-[(difluormetoksi)metil]-1,3,4-oksadiazol-2-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(2S)-oksolan-2-il]metil}-1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(5-{[(2R)-oksolan-2-il]metil}-1,3,4-oksadiazol-2-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 1-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)etan-1-ol; 2-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)propan-2-ol; (1S)-1-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)-2-feniletan-1-ol; (S)-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)(fenil)metanol; 2-[3-(2-metoksipropan-2-il)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(1-metoksietil)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(oksan-4-il)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{3-[(4-fluorfenoksi)metil]-1,2,4-oksadiazol-5-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(ciklopropilmetil)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-{3-[(oksolan-2-il)metil]-1,2,4-oksadiazol-5-il}-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(3-ciklopropil-1,2,4-oksadiazol-5-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(oksolan-3-il)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-(3-tert-butil-1,2,4-oksadiazol-5-il)-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(2-metoksietil)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; 2-[3-(metoksimetil)-1,2,4-oksadiazol-5-il]-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-3-amin; (5-{3-amino-4-klor-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-5-[3-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-5-[2-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; 5-amino-N-benzil-6-[5-(hidroksimetil)-1,3,4-oksadiazol-2-il]-N-metilpiridin-3-sulfonamid; {5-[3-amino-5-(benzensulfonil)piridin-2-il]-1,3,4-oksadiazol-2-il}metanol; (5-{3-amino-5-[4-(trifluormetil)benzen-1-sulfonil]piridin-2-il}-1,3,4-tiadiazol-2-il)metanol; (5-{3-amino-6-brom-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-6-klor-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-5-[2-(propan-2-il)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; (5-{3-amino-4-brom-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol; i 2-(5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,2,4-oksadiazol-3-il)etan-1-ol.
14. Spoj u skladu s patentnim zahtjevom 13, naznačen time što je (5-{3-amino-5-[4-(trifluormetoksi)benzen-1-sulfonil]piridin-2-il}-1,3,4-oksadiazol-2-il)metanol, ili njegova farmaceutski prihvatljiva sol.
15. Farmaceutski pripravak, naznačen time što sadrži terapijski djelotvornu količinu spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegove farmaceutski prihvatljive soli, u kombinaciji s farmaceutski prihvatljivim nosačem.
16. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak u skladu s patentnim zahtjevom 15, naznačeni time što su namijenjeni upotrebi u medicini.
17. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak u skladu s patentnim zahtjevom 15, naznačeni time što su namijenjeni upotrebi u liječenju cistične fibroze.
18. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, ili njegovu farmaceutski prihvatljivu sol, kao i jedan ili više korigensa, ili jedno ili više dodatnih terapijskih sredstava.
19. Farmaceutski pripravak u skladu s patentnim zahtjevom 18, naznačen time što se dodatna terapijska sredstva bira iz skupine koju čine modulatori CFTR i amplifikatori CFTR, po mogućnosti modulatori CFTR.
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