HRP20191754T1 - Spojevi i postupci za antivirusno liječenje - Google Patents
Spojevi i postupci za antivirusno liječenje Download PDFInfo
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- HRP20191754T1 HRP20191754T1 HRP20191754TT HRP20191754T HRP20191754T1 HR P20191754 T1 HRP20191754 T1 HR P20191754T1 HR P20191754T T HRP20191754T T HR P20191754TT HR P20191754 T HRP20191754 T HR P20191754T HR P20191754 T1 HRP20191754 T1 HR P20191754T1
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- Croatia
- Prior art keywords
- alkyl
- nr11c
- nr11r12
- heterocyclyl
- cycloalkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 36
- 230000000840 anti-viral effect Effects 0.000 title 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 132
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 64
- 229910052757 nitrogen Inorganic materials 0.000 claims 37
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 28
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 28
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 24
- 229910017711 NHRa Inorganic materials 0.000 claims 23
- 229910052799 carbon Inorganic materials 0.000 claims 23
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- -1 C2-C20 heterocyclyl Chemical group 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- MTPVBMVUENFFLL-HXUWFJFHSA-N 1-(2-fluorophenyl)-3-[(3s)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)N[C@@H]1C(=O)NC2=CC=CC=C2C(C=2C=CC=CC=2)=N1 MTPVBMVUENFFLL-HXUWFJFHSA-N 0.000 claims 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 108700002314 gontivimab Proteins 0.000 claims 2
- 229960001521 motavizumab Drugs 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229960000402 palivizumab Drugs 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- ANQAHRBJLMNFAK-UHFFFAOYSA-N 1-cyclopropyl-3-[[1-(3-hydroxypropyl)benzimidazol-2-yl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound N=1C2=CC=CC=C2N(CCCO)C=1CN(C1=O)C2=CN=CC=C2N1C1CC1 ANQAHRBJLMNFAK-UHFFFAOYSA-N 0.000 claims 1
- KSHJXDWYTZJUEI-UHFFFAOYSA-N 1-cyclopropyl-3-[[1-(4-hydroxybutyl)benzimidazol-2-yl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound N=1C2=CC=CC=C2N(CCCCO)C=1CN(C1=O)C2=CN=CC=C2N1C1CC1 KSHJXDWYTZJUEI-UHFFFAOYSA-N 0.000 claims 1
- BLUJRJMLDHEMRX-UHFFFAOYSA-N 2-[[2-hydroxy-5-[(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1N=Cc1ccc(O)c(c1)C(c1ccc(O)cc1)c1cc(C=Nn2nnnc2C)ccc1O BLUJRJMLDHEMRX-UHFFFAOYSA-N 0.000 claims 1
- 101150073096 NRAS gene Proteins 0.000 claims 1
- 241000711904 Pneumoviridae Species 0.000 claims 1
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000013160 medical therapy Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000030925 respiratory syncytial virus infectious disease Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Classifications
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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
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- 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
- A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (23)
1. Spoj Formule I:
ili njegova farmaceutski prihvatljiva sol;
pri čemu:
a) Y1 je N, NH ili CH, Y2 je C, Y3 je N ili CR8’, Y4 je N ili C i Y5 je N, NR2’ ili CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’; ili
b) Y1 je N, NH ili CH, Y2 je N ili C, Y3 je N ili CR8’, Y4 je N ili C, i Y5 je N ili NR2’, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’; ili
c) Y1 je N, NH ili CH, Y2 je N ili C, Y3 je CR8’, Y4 je N ili C, i Y5 je N, NR2’ ili CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’;
isprekidane veze ----su izabrane između jednostrukih veza i dvostrukih veza tako da osiguraju aromatični sustav prstena;
A je -(CR4R4’)n-pri čemu bilo koja CR4 R4’ spomenute -(CR4 R4’)n-može opcionalno biti zamijenjena sa -O-, -S-, ili -S(O)p-;
n je 3, 4, 5 ili 6;
svaki p je 1 ili 2;
Ar je C2-C20 heterociklil grupa ili C6-C20 aril grupa, pri čemu C2-C20 heterociklil grupa ili C6-C20 aril grupa je opcionalno supstituirana sa 1 do 5 R6;
X je -C(R13)(R14)-, -N(CH2R14)-ili -NH-, ili X je odsutna;
R1je H, -OR11, -NR11R12, -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11, -S(O)pRa, NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, --S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R2 je H, CN, NO2, halogen ili (C1-C8)alkil;
R2’ je H ili (C1-C8)alkil;
R3 je H, -OR11, -NR11R12 , -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R3’ je H, -OR11, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka R4 je nezavisno
H, -OR11, -NR11R12 -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 , N3, CN, NO2, SR11, -S(O)pRa, NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12,-C(=O)SR11, -S(O)p(OR11), -SO2NR11R12 , NR11S(O)p(OR11), -NR11SOpNR11R12, NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil; i
svaka R4’ je nezavisno H, OR11, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
ili dvije R4 na susjednim ugljikovim atomima, kada se uzmu zajedno, mogu tvoriti dvostruku vezu između dva atoma ugljika za koja su vezane ili mogu tvoriti (C3-C7)cikloalkilni prsten pri čemu jedan ugljikov atom od spomenutog (C3-C7)cikloalkilnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-ili -NRa-;
ili dvije R4 na ugljikovim atomima koji nisu susjedni, kada se uzmu zajedno, mogu tvoriti (C3-C7)cikloalkilni prsten pri čemu jedan atom ugljika spomenutog (C3-C7)cikloalkilnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-ili -NRa-;
ili dvije R4 i dvije R4’ na susjednim ugljikovim atomima, kada se uzmu zajedno, mogu opcionalno tvoriti supstituirani C6 arilni prsten;
ili jedna R4 i jedna R4’ na istom atomu ugljika, kada se uzmu zajedno, mogu tvoriti (C3-C7)cikloalkilni prsten pri čemu jedan atom ugljika spomenutog (C3-C7)cikloalkilnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH- ili NRa-;
svaka R5 je nezavisno H, -OR11, -NR11R12 -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 , N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka R5’ je nezavisno H, -OR11, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka R6 je nezavisno H, okso, -OR11, -NR11R12 -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 , N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
ili dvije R6 na susjednim atomima ugljika, kada se uzmu zajedno, mogu tvoriti (C3-C7)cikloalkilni prsten pri čemu jedan atom ugljika spomenutog (C3-C7)cikloalkilnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-ili -NRa-;
ili bilo koja R6 pored obavezne karbonilne grupe spomenutog Ar, kada se uzme zajedno sa R3, može tvoriti vezu ili -(CR5R5’)m-grupa pri čemu m je 1 ili 2;
ili bilo koja R6 pored obavezne karbonilne grupe spomenutog Ar, kada se uzme zajedno sa R2 ili R2’ može tvoriti vezu;
R7 je H, -OR11, -NR11R12, -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R8 je H, -OR11, -NR11R12 , -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R8’ je H, -OR11, -NR11R12,-NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11,
-S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11),
-SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil,
(C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka Ra je nezavisno (C1-C8)alkil, (C1-C8)haloalkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil,
C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil pri čemu bilo koja (C1-C8)alkil, (C1-C8)haloalkil, (C2-C8)alkenil ili (C2-C8)alkinil od Ra je opcionalno supstituirana s jednom ili više OH, NH2, CO2H, C2-C20 heterociklil, i pri čemu bilo koja aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil od Ra je opcionalno supstituirana s jednom ili više -OH, -NH2, CO2H, C2-C20 heterociklil ili (C1-C8)alkil;
svaka R11 ili R12 je nezavisno H, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20
aril, C2-C20 heterociklil, (C3-C7)cikloalkil, (C3-C7)cikloalkil(C1-C8)alkil, -C(=O)Ra ili -S(O)pRa; ili pri čemu
R11 i R12 su vezane za dušik i mogu opcionalno zajedno s dušikomza koji su obje vezane tvoriti 3- do 7-člani heterociklični prsten pri čemu bilo koji ugljikov atom spomenutog heterocikličnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-, -NRa- ili -C(O)-;
R13 je H ili (C1-C8)alkil;
R14 je H, (C1-C8)alkil, NR11R12, NR11C(O)R11, NR11C(O)OR11, NR11C(O)NR11R12, NR11S(O)pRa,
-NR11S(O)p(OR11) ili NR11SOpNR11R12; i
pri čemu svaka (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil od svake R1, R2, R2’, R3, R3’, R4, R4’, R5, R5’, R6, R7, R8, R8’, R11 ili R12 je nezavisno, opcionalno supstituirana s jednom ili više od okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, -S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, -C(=O)NH2, -NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NRaC(O)Ra, -NHC (O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)NH2, -NHC(O)NH Ra, -NHC(O)N(Ra)2,-NHC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(Ra)2,-NRaS(O)pNH2,-NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, -OC(=O)Ra, -OP(O)(OH)2 ili Ra.
2. Spoj prema zahtjevu 1 pri čemu:
a) Y1 je N, NH ili CH, Y2 je C, Y3 je N ili CR8’, Y4 je N ili C i Y5 je N, NR2’ ili CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’; ili
b) Y1 je N, NH ili CH, Y2 je N ili C, Y3 je N ili CR8’, Y4 je N ili C, i Y5 je N ili NR2’, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’; ili
c) Y1 je N, NH ili CH, Y2 je N ili C, Y3 je CR8’, Y4 je N ili C, i Y5 je N, NR2’ ili CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’;
isprekidane veze ----su izabrane između jednostrukih veza i dvostrukih veza tako da osiguraju aromatični sustav prstena;
A je -(CR4 R4’)n- pri čemu bilo koja CR4 R4’ spomenute -(CR4 R4’)n-može opcionalno biti zamijenjena sa -O-, -S-, ili -S(O)p-;
n je 3, 4, 5 ili 6;
svaki p je 1 ili 2;
Ar je C2-C20 heterociklil grupa ili C6-C20 aril grupa, pri čemu C2-C20 heterociklil grupa ili
C6-C20 aril grupa je opcionalno supstituirana sa 1 do 5 R6;
X je -C(R13)(R14)-, -N(CH2R14)- ili -NH-, ili X je odsutna;
R1 je H, -OR11, -NR11R12 , -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11,
-S(O)pRa, NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, --S(O)p(OR11),
-SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil,
(C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R2 je H, CN, NO2, halogen ili (C1-C8)alkil;
R2’ je H ili (C1-C8)alkil;
R3 je H, -OR11, -NR11R12 , -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12, N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12 halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R3’ je H, -OR11, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka R4 je nezavisno
H, -OR11, -NR11R12 -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 , N3, CN, NO2, SR11, -S(O)pRa, NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, NR11S(O)p(OR11), -NR11SOpNR11R12, NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil; i
svaka R4’ je nezavisno H, OR11, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka R6 je nezavisno H,
okso, -OR11, -NR11R12 -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 , N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R7 je H, -OR11, -NR11R12, -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R8 je H, -OR11, -NR11R12, -NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12 -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
R8’ je H, -OR11, -NR11R12,-NR11C(O)R11, -NR11C(O)OR11, -NR11C(O)NR11R12 N3, CN, NO2, -SR11, -S(O)pRa, -NR11S(O)pRa, -C(=O)R11, -C(=O)OR11, -C(=O)NR11R12, -C(=O)SR11, -S(O)p(OR11), -SO2NR11R12, -NR11S(O)p(OR11), -NR11SOpNR11R12, -NR11C(=NR11)NR11R12, halogen, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil;
svaka Ra je nezavisno (C1-C8)alkil, (C1-C8)haloalkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil pri čemu bilo koja (C1-C8)alkil, (C1-C8)haloalkil, (C2-C8)alkenil ili (C2-C8)alkinil Ra je opcionalno supstituirana sa jednom ili više OH, NH2, CO2H, C2-C20 heterociklil, i pri čemu bilo koja aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil od Ra je opcionalno supstituirana sa jednom ili više -OH, -NH2, CO2H, C2-C20 heterociklil ili (C1-C8)alkil;
svaka R11 ili R12 je nezavisno H, (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, (C3-C7)cikloalkil, (C3-C7)cikloalkil(C1-C8)alkil, -C(=O)Ra ili -S(O)pRa; ili kada
R11 i R12 su vezane za dušik i mogu opcionalno zajedno s dušikom za koji su obje vezane tvoriti 3- do 7-člani heterociklični prsten pri čemu bilo koji atom ugljika spomenutog heterocikličnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-, -NRa- ili -C(O)-;
R13 je H ili (C1-C8)alkil;
R14 je H, (C1-C8)alkil, NR11R12, NR11C(O)R11, NR11C(O)OR11, NR11C(O)NR11R12, NR11S(O)pRa, NR11S(O)p(OR11) ili NR11SOpNR11R12;
i pri čemu svaka (C1-C8)alkil, (C2-C8)alkenil, (C2-C8)alkinil, aril(C1-C8)alkil, C6-C20 aril, C2-C20 heterociklil, C2-C20 heterociklil(C1-C8)alkil, (C3-C7)cikloalkil ili (C3-C7)cikloalkil(C1-C8)alkil od svake R1, R2, R2’, R3, R3’, R4, R4’R6, R7, R8, R8’, R11 ili R12 je nezavisno, opcionalno supstituirana sa jednom ili više okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, -S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, -C(=O)NH2, -NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NR aC(O)Ra, -NHC(O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)N H2, -NHC(O)NHRa, -NHC(O)N(Ra)2,-NHC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(Ra)2,-NRaS(O)pNH2, -NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, -OC(=O)Ra, -OP(O)(OH)2 ili Ra.
3. Spoj prema zahtjevu 1, pri čemu spoj formule I je spoj formule Ic:
ili njegova farmaceutski prihvatljiva sol.
4. Spoj prema bilo kojem od zahtjeva 1-3, pri čemu R3 i R3’ su svaka H.
5. Spoj prema bilo kojem od zahtjeva 1-4, pri čemu n je 3.
6. Spoj prema bilo kojem od zahtjeva 1-5, pri čemu svaka R4 i svaka R4’ je H.
7. Spoj prema bilo kojem od zahtjeva 1-6, pri čemu A je -(CH2)3-.
8. Spoj prema bilo kojem od zahtjeva 1-7, pri čemu
a) Y1 je N, NH ili CH, Y2 je C, Y3 je N, Y4 je N ili C i Y5 je NR2’
ili
CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’;
ili
b) Y1je N,NH ili CH, Y2 je N ili C, Y3je N ili CR8’, Y4je N ili C, i Y5je N, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N ili NH;
ili
c) Y1 je N, NH ili CH, Y2 je N ili C, Y3 je CR8’, Y4 je N ili C, i Y5 je NR2’ ili CR2, pri čemu bar dvije od Y1, Y2, Y3, Y4 i Y5 su nezavisno N, NH ili NR2’;
ili
d) Y1 je N, Y2 je C, Y3 je N, Y4 je N i Y5 je CR2;
ili
e) Y1 je N, Y2 je N, Y3 je CR8’, Y4je C, i Y5 je CR2.
9. Spoj prema bilo kojem od zahtjeva 1-8, pri čemu R2’, R2 i R8’ su svaka H.
10. Spoj prema zahtjevu 1, pri čemu spoj formule I je:
(a) spoj formule Ix4:
pri čemu Z je:
ili njegova sol;
ili pri čemu
(b) spoj formule I je spoj formule Im:
ili njegova sol.
11. Spoj prema zahtjevu 10, prema formuli Im pri čemu R2 je H.
12. Spoj prema bilo kojem od zahtjeva 1-9, ili spoj prema formuli Im u zahtjevu 10, ili spoj prema zahtjevu 11, pri čemu X je -C(R13)(R14)- ili X je odsutna.
13. Spoj prema bilo kojem od zahtjeva 1-9, ili spoj prema formuli Im u zahtjevu 10, ili spoj prema zahtjevu 11, pri čemu R13 je H i R14 je -NHS(O)2(C1-C3)alkil.
14. Spoj prema bilo kojem od zahtjeva 1-9, ili spoj prema formuli Im u zahtjevu 10, ili spoj prema zahtjevu 11, pri čemu X je odsutna.
15. Spoj prema bilo kojem od zahtjeva 1-14, pri čemu R7 je H ili (C1-C8)alkil, pri čemu (C1-C8)alkil je opcionalno supstituirana s jednim ili više okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, -C(=O)NH2, -NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NRaC(O)Ra, -NHC(O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)NH2, -NHC(O)NHRa, -NHC(O)N(Ra)2, -NHC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(Ra)2, -NRaS(O)pNH2, -NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, -OC(=O)Ra, -OP(O)(OH)2 ili Ra, tako da kada R7 je H ili metil.
16. Spoj prema bilo kojem od zahtjeva 1-15, pri čemu R1 je
(a) H, -NR11R12, (C1-C8)alkil ili C2-C20 heterociklil pri čemu (C1-C8)alkil ili C2-C20 heterociklil je opcionalno supstituirana s jednom ili više okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, -S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, -C(=O)NH2, NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NRaC(O)Ra, -NHC(O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)NH2, -NHC(O)NHRa, -NHC(O)N(Ra)2, -NHC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(Ra)2, -NRaS(O)pNH2, -NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, -OC(=O)Ra, -OP(O)(OH)2 ili Ra;
ili pri čemu
(b) R1 je H, (C1-C3)alkil ili -NR11R12, pri čemu svaka R11 ili R12 je nezavisno H ili (C1-C3)alkil; ili R11 i R12 zajedno s dušikom za koji su obje vezane tvoriti 3- do 7-člani heterociklični prsten pri čemu bilo koji atom ugljika spomenutog heterocikličnog prstena može opcionalno biti zamijenjen sa -O-, -S-, -S(O)p-, -NH-, -NRa- ili -C(O)-;
ili pri čemu
(c) R1 je H, metil ili azetidinil.
17. Spoj prema bilo kojem od zahtjeva 1-16 pri čemu
(a) R8 je -NR11R12, (C1-C8)alkil ili C2-C20 heterociklil pri čemu (C1-C8)alkil ili C2-C20 heterociklil je opcionalno supstituirana s jednom ili više okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, -S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, -C(=O)NH2, -NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NRaC(O)Ra, -NHC(O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)NH2, -NHC(O)NHRa, -NHC(O)N(Ra)2, -NHC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(R)2, -NRaS(O)pNH2, -NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, -OC(=O)Ra, -OP(O)(OH)2 ili Ra;
ili pri čemu
(b) R8 je (C1-C8)alkil, azetidinil ili pirolidinil, pri čemu azetidinil ili pirolidinil je opcionalno supstituirana s jednom ili više okso, halogen, hidroksi, -NH2, CN, N3, -N(Ra)2, -NHRa, -SH, -SRa, -S(O)pRa, -ORa, (C1-C8)alkil, (C1-C8)haloalkil, -C(O)Ra, -C(O)H, -C(=O)ORa, -C(=O)OH, -C(=O)N(Ra)2, -C(=O)NHRa, C(=O)NH2, -NHS(O)pRa, -NRaS(O)pRa, -NHC(O)Ra, -NRaC(O)Ra, -NHC(O)ORa, -NRaC(O)ORa, -NRaC(O)NHRa, -NRaC(O)N(Ra)2, -NRaC(O)NH2, -NHC(O)NHRa, -NHC(O)N(Ra)2, -N HC(O)NH2, =NH, =NOH, =NORa, -NRaS(O)pNHRa, -NRaS(O)pN(Ra)2, -NRaS(O)pNH2, -NHS(O)pNHRa, -NHS(O)pN(Ra)2, -NHS(O)pNH2, p-OC(=O)Ra, -OP(O)(OH)2 ili Ra;
ili pri čemu
(c) R8 je metil, azetidinil ili pirolidinil, pri čemu azetidinil ili pirolidinil je opcionalno supstituirana s jednom ili više hidroksi, NH2 ili CN.
18. Spoj prema bilo kojem od zahtjeva 1-17 , pri čemu
(a) Ar je fenil ili 5-6 člani monociklični heteroaril, pri čemu fenil ili 5-6 člani monociklični heteroaril je opcionalno supstituiran sa 1 do 5 R6;
ili pri čemu
(b) Ar je fenil, piridinil ili tienil, pri čemu fenil, piridinil ili tienil je opcionalno supstituiran sa 1 do 5 R6.
19. Spoj prema bilo kojem od zahtjeva 1-18, pri čemu
(a) svaka R6 je -NR11S(O)Ra, halogen, ili (C1-C8)alkil;
ili pri čemu
(b) svaka R6 je -NHS(O)2CH3, kloro, bromo ili metil.
20. Spoj prema zahtjevu 1, izabran između:
i
i njihovih farmaceutski prihvatljivih soli;
ili spoj izabran između:
i
i njihovih farmaceutski prihvatljivih soli.
21. Farmaceutski sastav koji obuhvaća terapeutski djelotvornu količinu spojeva kao što se opisuje u bilo kojem od zahtjeva 1-20 ili njegovu farmaceutski prihvatljivu sol i farmaceutski prihvatljivi nosač, opcionalno pri čemu farmaceutska kompozicija dalje obuhvaća bar jedno terapeutsko sredstvo izabrano između ribavirina, palivizumaba, motavizumaba, RSV-IGIV, MEDI-557, A-60444, MDT-637, BMS-433771, ALN-RSV01 i ALX-0171 i njihovih mješavina.
22. Spoj kao što je opisano u bilo kojem od zahtjeva 1-20, ili njegova farmaceutski prihvatljiva sol, za upotrebu u medicinskoj terapiji, kao što je za upotrebu u terapeutskom ili profilaktičkom liječenju infekcije virusom Pneumovirinae ili infekcije sa respiratornim sincicijalnim virusom.
23. Spoj za upotrebu prema zahtjevu 22, koje dalje obuhvaća primjenu terapeutski djelotvorne količine bar jednog drugog terapeutskog sredstva ili njegove kompozicije koja obuhvaća ribavirin, palivizumab, motavizumab, RSV-IGIV, MEDI-557, A-60444, MDT-63, BMS-433771, ALN-RSV01 i ALX-0171 i njihove mješavine.
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| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| WO2011099832A2 (en) | 2010-02-12 | 2011-08-18 | Crystalgenomics, Inc. | Novel benzimidazole compound, preparation method thereof and pharmaceutical composition comprising the same |
| US8877707B2 (en) * | 2010-05-24 | 2014-11-04 | Presidio Pharmaceuticals, Inc. | Inhibitors of HCV NS5A |
| RS54761B1 (sr) * | 2010-06-24 | 2016-10-31 | Gilead Sciences | Pirazolo[1,5-a]pirimidini i-triazini kao antiviralni agensi |
| ES2524356T3 (es) * | 2010-07-22 | 2014-12-05 | Gilead Sciences, Inc. | Métodos y compuestos para tratar infecciones provocadas por virus Paramyxoviridae |
| WO2013096681A1 (en) | 2011-12-22 | 2013-06-27 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| LT2838900T (lt) | 2012-04-17 | 2019-11-11 | Gilead Sciences Inc | Junginiai ir būdai, skirti priešvirusinei terapijai |
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2013
- 2013-04-17 LT LT13718996T patent/LT2838900T/lt unknown
- 2013-04-17 KR KR1020207010642A patent/KR102181318B1/ko active IP Right Grant
- 2013-04-17 KR KR1020147030957A patent/KR102102283B1/ko active IP Right Grant
- 2013-04-17 WO PCT/US2013/037001 patent/WO2013158776A1/en active Application Filing
- 2013-04-17 PL PL13718996T patent/PL2838900T3/pl unknown
- 2013-04-17 MX MX2014012450A patent/MX355781B/es active IP Right Grant
- 2013-04-17 JP JP2015507151A patent/JP2015516976A/ja active Pending
- 2013-04-17 IN IN9173DEN2014 patent/IN2014DN09173A/en unknown
- 2013-04-17 ES ES13718996T patent/ES2750153T3/es active Active
- 2013-04-17 HU HUE13718996A patent/HUE045727T2/hu unknown
- 2013-04-17 CN CN201380030470.6A patent/CN104583211A/zh active Pending
- 2013-04-17 SI SI201331567T patent/SI2838900T1/sl unknown
- 2013-04-17 US US13/865,069 patent/US8980878B2/en active Active
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- 2013-04-17 EA EA201491889A patent/EA027855B1/ru not_active IP Right Cessation
- 2013-04-17 SG SG11201406736VA patent/SG11201406736VA/en unknown
- 2013-04-17 DK DK13718996.5T patent/DK2838900T3/da active
- 2013-04-17 CN CN201710094970.6A patent/CN106986869A/zh active Pending
- 2013-04-17 SG SG10201610166VA patent/SG10201610166VA/en unknown
- 2013-04-17 PT PT137189965T patent/PT2838900T/pt unknown
- 2013-04-17 EP EP13718996.5A patent/EP2838900B1/en active Active
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2014
- 2014-10-07 IL IL235062A patent/IL235062A0/en unknown
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2015
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2016
- 2016-06-24 US US15/191,974 patent/US20170029427A1/en not_active Abandoned
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2017
- 2017-03-21 JP JP2017054488A patent/JP6291103B2/ja active Active
- 2017-06-09 US US15/618,974 patent/US10174038B2/en active Active
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2018
- 2018-02-08 JP JP2018020909A patent/JP2018095657A/ja not_active Withdrawn
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2019
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