HRP20191140T1 - Spojevi i pripravci kao inhibitori c-kit kinaze - Google Patents
Spojevi i pripravci kao inhibitori c-kit kinaze Download PDFInfo
- Publication number
- HRP20191140T1 HRP20191140T1 HRP20191140TT HRP20191140T HRP20191140T1 HR P20191140 T1 HRP20191140 T1 HR P20191140T1 HR P20191140T T HRP20191140T T HR P20191140TT HR P20191140 T HRP20191140 T HR P20191140T HR P20191140 T1 HRP20191140 T1 HR P20191140T1
- Authority
- HR
- Croatia
- Prior art keywords
- oxadiazol
- imidazo
- carboxamide
- pyridine
- methylphenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 38
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 title claims 4
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 title claims 4
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 125000005842 heteroatom Chemical group 0.000 claims 41
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 26
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims 26
- 229910052760 oxygen Inorganic materials 0.000 claims 24
- 229910052717 sulfur Inorganic materials 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 20
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 17
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 14
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000003003 spiro group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 10
- 235000005152 nicotinamide Nutrition 0.000 claims 9
- 239000011570 nicotinamide Substances 0.000 claims 9
- -1 -OR4 Chemical group 0.000 claims 8
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 8
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 5
- 229910052805 deuterium Inorganic materials 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 4
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims 4
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- VBSCTWFMHAWPSW-UHFFFAOYSA-N n-[5-[5-(3-hydroxy-3-methylcyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(C)(O)C1 VBSCTWFMHAWPSW-UHFFFAOYSA-N 0.000 claims 4
- 201000008312 primary pulmonary hypertension Diseases 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- RHNJOZCVGSBEAG-KBPBESRZSA-N n-[5-[5-[(1r,2s)-2-fluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@H]1C[C@@H]1F RHNJOZCVGSBEAG-KBPBESRZSA-N 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 2
- HVLLSFSZBNWGEY-UHFFFAOYSA-N 7-cyano-n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC(=CC3=NC=2)C#N)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 HVLLSFSZBNWGEY-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000016097 disease of metabolism Diseases 0.000 claims 2
- 230000003176 fibrotic effect Effects 0.000 claims 2
- ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- RHJXTZUDRRZZBR-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(=O)C1 RHJXTZUDRRZZBR-UHFFFAOYSA-N 0.000 claims 2
- XCRIYMJWHVQZPI-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]-6-(5-methyl-1h-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1C(C)=NN=C1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)F)=CN=C2C=C1 XCRIYMJWHVQZPI-UHFFFAOYSA-N 0.000 claims 2
- JHFRDCLISNAGNN-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2-fluoroethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCCF)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 JHFRDCLISNAGNN-UHFFFAOYSA-N 0.000 claims 2
- FJXNYFVDBNXCRS-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2-methoxyethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(COCCOC)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 FJXNYFVDBNXCRS-UHFFFAOYSA-N 0.000 claims 2
- PZQWOZMFFXZLHP-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 PZQWOZMFFXZLHP-UHFFFAOYSA-N 0.000 claims 2
- YYJQXSJQDPOQPK-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 YYJQXSJQDPOQPK-UHFFFAOYSA-N 0.000 claims 2
- DQBZLRRBDNJYLN-UHFFFAOYSA-N n-[5-[5-(3-aminocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(N)C1 DQBZLRRBDNJYLN-UHFFFAOYSA-N 0.000 claims 2
- HAJVNPLYVSZWRG-CYBMUJFWSA-N n-[5-[5-[(1r)-2,2-difluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@H]1CC1(F)F HAJVNPLYVSZWRG-CYBMUJFWSA-N 0.000 claims 2
- HAJVNPLYVSZWRG-ZDUSSCGKSA-N n-[5-[5-[(1s)-2,2-difluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@@H]1CC1(F)F HAJVNPLYVSZWRG-ZDUSSCGKSA-N 0.000 claims 2
- RHNJOZCVGSBEAG-ZIAGYGMSSA-N n-[5-[5-[(1s,2r)-2-fluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@@H]1C[C@H]1F RHNJOZCVGSBEAG-ZIAGYGMSSA-N 0.000 claims 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- SVDQVKHOQYZWAL-UHFFFAOYSA-N (1-methylcyclopropyl) n-[2-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]ethyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CCNC(=O)OC1(C)CC1 SVDQVKHOQYZWAL-UHFFFAOYSA-N 0.000 claims 1
- UUHURBSCNYMVOQ-UHFFFAOYSA-N (1-methylcyclopropyl) n-[[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]methyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CNC(=O)OC1(C)CC1 UUHURBSCNYMVOQ-UHFFFAOYSA-N 0.000 claims 1
- NXELOAFEBVHTSP-UHFFFAOYSA-N (1-methylcyclopropyl) n-[[3-[4-methyl-3-[[7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbonyl]amino]phenyl]-1,2,4-oxadiazol-5-yl]methyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC(=CC3=NC=2)C(F)(F)F)C(C)=CC=C1C(N=1)=NOC=1CNC(=O)OC1(C)CC1 NXELOAFEBVHTSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims 1
- WMOGDCLNSOMBFC-UHFFFAOYSA-N 2-[4-[3-[[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]carbamoyl]imidazo[1,2-a]pyridin-6-yl]pyrazol-1-yl]acetic acid Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=NN(CC(O)=O)C=1 WMOGDCLNSOMBFC-UHFFFAOYSA-N 0.000 claims 1
- PYJGRPRPIMKYEB-UHFFFAOYSA-N 3-n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3,6-dicarboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(C=CC3=NC=2)C(N)=O)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 PYJGRPRPIMKYEB-UHFFFAOYSA-N 0.000 claims 1
- YYJQXSJQDPOQPK-CLQKNIGZSA-N 5,6,7,8-tetradeuterio-n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C([2H])=C([2H])C([2H])=C([2H])N2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 YYJQXSJQDPOQPK-CLQKNIGZSA-N 0.000 claims 1
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- 239000003112 inhibitor Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 1
- 201000006512 mast cell neoplasm Diseases 0.000 claims 1
- 208000008585 mastocytosis Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
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- JQAOVLHZPSXMAK-UHFFFAOYSA-N methyl n-[1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(NC(=O)OC)CCC1 JQAOVLHZPSXMAK-UHFFFAOYSA-N 0.000 claims 1
- KBQARZYCSSUVFQ-UHFFFAOYSA-N methyl n-[1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclopropyl]-n-methoxycarbonylcarbamate Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(N(C(=O)OC)C(=O)OC)CC1 KBQARZYCSSUVFQ-UHFFFAOYSA-N 0.000 claims 1
- PEZHCCGPKBWAHP-UHFFFAOYSA-N methyl n-[1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclopropyl]carbamate Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(NC(=O)OC)CC1 PEZHCCGPKBWAHP-UHFFFAOYSA-N 0.000 claims 1
- QRRXDPDVPOSIFC-UHFFFAOYSA-N methyl n-[3,3-difluoro-1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(NC(=O)OC)CC(F)(F)C1 QRRXDPDVPOSIFC-UHFFFAOYSA-N 0.000 claims 1
- VMPUVVKGRPJUIX-UHFFFAOYSA-N methyl n-[3,3-difluoro-1-[3-[4-methyl-3-[(7-methylimidazo[1,2-a]pyridine-3-carbonyl)amino]phenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC(C)=CC4=NC=3)C(C)=CC=2)=NOC=1C1(NC(=O)OC)CC(F)(F)C1 VMPUVVKGRPJUIX-UHFFFAOYSA-N 0.000 claims 1
- CFAUIHXPMUVAFG-UHFFFAOYSA-N methyl n-[3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound C1C(NC(=O)OC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 CFAUIHXPMUVAFG-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- STTCYAFMCPPVTG-UHFFFAOYSA-N n-[2-fluoro-5-[5-(3-methylidenecyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(F)=CC=C1C(N=1)=NOC=1C1CC(=C)C1 STTCYAFMCPPVTG-UHFFFAOYSA-N 0.000 claims 1
- XHGVWDXFZUEHRV-UHFFFAOYSA-N n-[2-methyl-5-[5-(2-oxospiro[3.3]heptan-6-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC21CC(=O)C2 XHGVWDXFZUEHRV-UHFFFAOYSA-N 0.000 claims 1
- VCGZRAXATKIMPO-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-methylidenecyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(=C)C1 VCGZRAXATKIMPO-UHFFFAOYSA-N 0.000 claims 1
- GYZVPSXFDGNLTL-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-morpholin-4-ylcyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1N1CCOCC1 GYZVPSXFDGNLTL-UHFFFAOYSA-N 0.000 claims 1
- CMKHFELGXWLQSX-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-oxocyclopentyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CCC(=O)C1 CMKHFELGXWLQSX-UHFFFAOYSA-N 0.000 claims 1
- OCHXFTLSZGBYGB-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-piperidin-1-ylcyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1N1CCCCC1 OCHXFTLSZGBYGB-UHFFFAOYSA-N 0.000 claims 1
- YPJQEOYEDWLTPQ-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-propan-2-yloxyiminocyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(=NOC(C)C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 YPJQEOYEDWLTPQ-UHFFFAOYSA-N 0.000 claims 1
- SRAWMPUQNJCKKF-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-pyrazol-1-ylcyclobutyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1N1C=CC=N1 SRAWMPUQNJCKKF-UHFFFAOYSA-N 0.000 claims 1
- TUZSVQWAIOHMAN-UHFFFAOYSA-N n-[2-methyl-5-[5-(5-oxaspiro[3.4]octan-2-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC21CCCO2 TUZSVQWAIOHMAN-UHFFFAOYSA-N 0.000 claims 1
- AJALWDBRAVSTFX-UHFFFAOYSA-N n-[2-methyl-5-[5-[(2,2,3,3-tetrafluorocyclobutyl)oxymethyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1COC1CC(F)(F)C1(F)F AJALWDBRAVSTFX-UHFFFAOYSA-N 0.000 claims 1
- BFENDVJZXZZBMZ-HAQQTFLXSA-N n-[2-methyl-5-[5-[(7r)-7-methyl-5,8-dioxaspiro[3.4]octan-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound O1[C@H](C)COC11CC(C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)C1 BFENDVJZXZZBMZ-HAQQTFLXSA-N 0.000 claims 1
- BFENDVJZXZZBMZ-LCVZGFTISA-N n-[2-methyl-5-[5-[(7s)-7-methyl-5,8-dioxaspiro[3.4]octan-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound O1[C@@H](C)COC11CC(C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)C1 BFENDVJZXZZBMZ-LCVZGFTISA-N 0.000 claims 1
- ZTSBMHAPDJMGKM-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(trifluoromethyl)cyclopropyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(C(F)(F)F)CC1 ZTSBMHAPDJMGKM-UHFFFAOYSA-N 0.000 claims 1
- MVWCFRFJCKNFKP-UHFFFAOYSA-N n-[2-methyl-5-[5-[3-(1,2,4-triazol-1-yl)cyclobutyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1N1C=NC=N1 MVWCFRFJCKNFKP-UHFFFAOYSA-N 0.000 claims 1
- BHYADCWMERYDNF-UHFFFAOYSA-N n-[2-methyl-5-[5-[3-(2-morpholin-4-ylethoxyimino)cyclobutyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1=NOCCN1CCOCC1 BHYADCWMERYDNF-UHFFFAOYSA-N 0.000 claims 1
- AXOIMIICKSYXMT-UHFFFAOYSA-N n-[2-methyl-5-[5-[3-(4-methylpiperazin-1-yl)cyclobutyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1CC(C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)C1 AXOIMIICKSYXMT-UHFFFAOYSA-N 0.000 claims 1
- LEKPOEMXPKTFIQ-UHFFFAOYSA-N n-[3-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2,6-dimethylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 LEKPOEMXPKTFIQ-UHFFFAOYSA-N 0.000 claims 1
- TVLMBEXTOHTRNS-UHFFFAOYSA-N n-[5-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(ON=1)=NC=1C1CC1 TVLMBEXTOHTRNS-UHFFFAOYSA-N 0.000 claims 1
- XBZQIWZQXUSRKJ-UHFFFAOYSA-N n-[5-(5-cyclobutyl-1,2,4-oxadiazol-3-yl)-2-fluorophenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(F)=CC=C1C(N=1)=NOC=1C1CCC1 XBZQIWZQXUSRKJ-UHFFFAOYSA-N 0.000 claims 1
- MUNJUJLGPXZJIQ-UHFFFAOYSA-N n-[5-(5-cyclobutyl-1,2,4-oxadiazol-3-yl)-2-methylphenyl]-6-(2,2,2-trifluoroethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCC(F)(F)F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CCC1 MUNJUJLGPXZJIQ-UHFFFAOYSA-N 0.000 claims 1
- LAAFMNKBPFCIJU-UHFFFAOYSA-N n-[5-(5-cyclobutyl-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CCC1 LAAFMNKBPFCIJU-UHFFFAOYSA-N 0.000 claims 1
- ZGOBVKLRYAOXSK-UHFFFAOYSA-N n-[5-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CCCC1 ZGOBVKLRYAOXSK-UHFFFAOYSA-N 0.000 claims 1
- IACBZSGWVMFOJV-UHFFFAOYSA-N n-[5-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC1 IACBZSGWVMFOJV-UHFFFAOYSA-N 0.000 claims 1
- CITATNXHTLRWAC-UHFFFAOYSA-N n-[5-[(3,3-difluorocyclobutyl)carbamoyl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(=O)NC1CC(F)(F)C1 CITATNXHTLRWAC-UHFFFAOYSA-N 0.000 claims 1
- UMMDASRURJTCCN-UHFFFAOYSA-N n-[5-[3-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-5-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(ON=1)=NC=1C1CC(F)(F)C1 UMMDASRURJTCCN-UHFFFAOYSA-N 0.000 claims 1
- KZDMOSVLZIBBNH-UHFFFAOYSA-N n-[5-[5-(1-aminocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(N)CCC1 KZDMOSVLZIBBNH-UHFFFAOYSA-N 0.000 claims 1
- WLBKDTIWZLBQKG-UHFFFAOYSA-N n-[5-[5-(1-aminocyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(N)CC1 WLBKDTIWZLBQKG-UHFFFAOYSA-N 0.000 claims 1
- GANVJQGJEYQSGI-UHFFFAOYSA-N n-[5-[5-(1-carbamoylcyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(C(N)=O)CC1 GANVJQGJEYQSGI-UHFFFAOYSA-N 0.000 claims 1
- AHFSNECLZXPMJX-UHFFFAOYSA-N n-[5-[5-(1-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(F)CCC1 AHFSNECLZXPMJX-UHFFFAOYSA-N 0.000 claims 1
- IMVBDLPHXQZTOB-UHFFFAOYSA-N n-[5-[5-(1-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(O)CCC1 IMVBDLPHXQZTOB-UHFFFAOYSA-N 0.000 claims 1
- URUHFYRBCQRUIC-UHFFFAOYSA-N n-[5-[5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(O)CC1 URUHFYRBCQRUIC-UHFFFAOYSA-N 0.000 claims 1
- KCAZMKTVLQMKCC-UHFFFAOYSA-N n-[5-[5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2,2,2-trifluoroethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCC(F)(F)F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC1(F)F KCAZMKTVLQMKCC-UHFFFAOYSA-N 0.000 claims 1
- HAJVNPLYVSZWRG-UHFFFAOYSA-N n-[5-[5-(2,2-difluorocyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC1(F)F HAJVNPLYVSZWRG-UHFFFAOYSA-N 0.000 claims 1
- VVYKXEVSEJUERS-UHFFFAOYSA-N n-[5-[5-(2-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC1O VVYKXEVSEJUERS-UHFFFAOYSA-N 0.000 claims 1
- CXAIUYZBLYTVTR-UHFFFAOYSA-N n-[5-[5-(2-hydroxyspiro[3.3]heptan-6-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC21CC(O)C2 CXAIUYZBLYTVTR-UHFFFAOYSA-N 0.000 claims 1
- QVVZVIMTCBNZEO-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2,4-dimethylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC(C)=C1C(N=1)=NOC=1C1CC(F)(F)C1 QVVZVIMTCBNZEO-UHFFFAOYSA-N 0.000 claims 1
- SGTKWTOWPIPHNT-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]-6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=NN(C)C=C1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)F)=CN=C2C=C1 SGTKWTOWPIPHNT-UHFFFAOYSA-N 0.000 claims 1
- ZUCAJOGACPVRKK-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]-6-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)F)=CN=C2C=C1 ZUCAJOGACPVRKK-UHFFFAOYSA-N 0.000 claims 1
- VWLGANZUNCNMJP-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]-6-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C(=C1)C=NN1CCN1CCOCC1 VWLGANZUNCNMJP-UHFFFAOYSA-N 0.000 claims 1
- XCXUYGGKVTVWJA-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(F)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 XCXUYGGKVTVWJA-UHFFFAOYSA-N 0.000 claims 1
- FZYVKXRUCUFWPT-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(1,3-thiazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C1=CSC=N1 FZYVKXRUCUFWPT-UHFFFAOYSA-N 0.000 claims 1
- UYLMYXBJJAZNJX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(1-hydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(C(O)C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 UYLMYXBJJAZNJX-UHFFFAOYSA-N 0.000 claims 1
- CAMGFDRRBKFXEX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(1-methylpyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=CN(C)N=1 CAMGFDRRBKFXEX-UHFFFAOYSA-N 0.000 claims 1
- NBSLKFJOTXPKOX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=NN(C)C=1 NBSLKFJOTXPKOX-UHFFFAOYSA-N 0.000 claims 1
- KEYOYTQRXGQPGL-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2,2,2-trifluoroethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCC(F)(F)F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 KEYOYTQRXGQPGL-UHFFFAOYSA-N 0.000 claims 1
- UVTVIZDRFNGZGM-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2,2-difluoroethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCC(F)F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 UVTVIZDRFNGZGM-UHFFFAOYSA-N 0.000 claims 1
- AQVGDQCIIGGJPL-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2-hydroxyethoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(COCCO)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 AQVGDQCIIGGJPL-UHFFFAOYSA-N 0.000 claims 1
- RWFRRCZOXFUFBX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2-morpholin-4-ylethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2CCN1CCOCC1 RWFRRCZOXFUFBX-UHFFFAOYSA-N 0.000 claims 1
- CCLJVGUJPXWOOW-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(CCC(=O)C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 CCLJVGUJPXWOOW-UHFFFAOYSA-N 0.000 claims 1
- NRUQPKZIUNPPNZ-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(4-methylimidazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=NC(C)=CN1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 NRUQPKZIUNPPNZ-UHFFFAOYSA-N 0.000 claims 1
- TYEOCDLQDPFRIX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(5-methyl-1h-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1C(C)=NC(C2=CN3C(C(=O)NC=4C(=CC=C(C=4)C=4N=C(ON=4)C4CC(F)(F)C4)C)=CN=C3C=C2)=N1 TYEOCDLQDPFRIX-UHFFFAOYSA-N 0.000 claims 1
- FADGXYVECDRQNC-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(5-methylimidazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CN=CN1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 FADGXYVECDRQNC-UHFFFAOYSA-N 0.000 claims 1
- XCYDGRAVLMZAMV-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(CO)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 XCYDGRAVLMZAMV-UHFFFAOYSA-N 0.000 claims 1
- SRDBLOPEORGLEG-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(methoxymethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(COC)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 SRDBLOPEORGLEG-UHFFFAOYSA-N 0.000 claims 1
- ZHTTUPZLXLKBER-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[(2-oxo-1,3-oxazolidin-3-yl)methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2CN1CCOC1=O ZHTTUPZLXLKBER-UHFFFAOYSA-N 0.000 claims 1
- WLWRVOASHCUSOL-CALCHBBNSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 WLWRVOASHCUSOL-CALCHBBNSA-N 0.000 claims 1
- KMBADQVFWVIROD-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[(4-methylpiperazin-1-yl)methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CC1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 KMBADQVFWVIROD-UHFFFAOYSA-N 0.000 claims 1
- LSWXHHBJJIGZTD-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=NN(CC(C)(C)O)C=1 LSWXHHBJJIGZTD-UHFFFAOYSA-N 0.000 claims 1
- STZWVRVZGPYDKL-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[1-(2-hydroxyethyl)pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=NN(CCO)C=1 STZWVRVZGPYDKL-UHFFFAOYSA-N 0.000 claims 1
- DKWKCRFGHXIPLX-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[1-(2-methoxyethyl)-5-methyl-1,2,4-triazol-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1=C(C)N(CCOC)N=C1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 DKWKCRFGHXIPLX-UHFFFAOYSA-N 0.000 claims 1
- FGAQHQPHMGQONA-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C(=C1)C=NN1CCN1CCOCC1 FGAQHQPHMGQONA-UHFFFAOYSA-N 0.000 claims 1
- ILMLCTYDPFLFJW-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[2-(4-methylpiperazin-1-yl)ethyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCC1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(ON=3)C3CC(F)(F)C3)C)=CN=C2C=C1 ILMLCTYDPFLFJW-UHFFFAOYSA-N 0.000 claims 1
- LRHHTPFGYJWATC-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[5-(methoxymethyl)-1h-1,2,4-triazol-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound COCC1=NNC(C2=CN3C(C(=O)NC=4C(=CC=C(C=4)C=4N=C(ON=4)C4CC(F)(F)C4)C)=CN=C3C=C2)=N1 LRHHTPFGYJWATC-UHFFFAOYSA-N 0.000 claims 1
- FLGYJSZOORSFEH-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2CN1CCN(CCO)CC1 FLGYJSZOORSFEH-UHFFFAOYSA-N 0.000 claims 1
- XHQBPWQRZZIMAA-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=C(F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 XHQBPWQRZZIMAA-UHFFFAOYSA-N 0.000 claims 1
- CYHBIKSLEMCECT-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)(F)C1 CYHBIKSLEMCECT-UHFFFAOYSA-N 0.000 claims 1
- VMMAYWQRBBMUSN-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-morpholin-4-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2N1CCOCC1 VMMAYWQRBBMUSN-UHFFFAOYSA-N 0.000 claims 1
- FDAOKJLCACKIFM-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-(difluoromethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC(OC(F)F)=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 FDAOKJLCACKIFM-UHFFFAOYSA-N 0.000 claims 1
- YIDCEVNXBMMFHY-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-[1-(2-hydroxyethyl)triazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=C2)=CN=C1C=C2C1=CN(CCO)N=N1 YIDCEVNXBMMFHY-UHFFFAOYSA-N 0.000 claims 1
- WZGYVSALYZWXML-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC(F)=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 WZGYVSALYZWXML-UHFFFAOYSA-N 0.000 claims 1
- QDBQXAHDNLLVQI-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-morpholin-4-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=C2)=CN=C1C=C2N1CCOCC1 QDBQXAHDNLLVQI-UHFFFAOYSA-N 0.000 claims 1
- SMXOEIFIDKLKCI-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-piperidin-4-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=C(C=2N=C(ON=2)C2CC(F)(F)C2)C=C1NC(=O)C(N1C=C2)=CN=C1C=C2C1CCNCC1 SMXOEIFIDKLKCI-UHFFFAOYSA-N 0.000 claims 1
- QMMUKLCBLNXISU-UHFFFAOYSA-N n-[5-[5-(3,3-difluorocyclobutyl)-1,3,4-oxadiazol-2-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(O1)=NN=C1C1CC(F)(F)C1 QMMUKLCBLNXISU-UHFFFAOYSA-N 0.000 claims 1
- HHUBMCNSFFNTCO-UHFFFAOYSA-N n-[5-[5-(3,3-dimethylcyclobutyl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(C)(C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 HHUBMCNSFFNTCO-UHFFFAOYSA-N 0.000 claims 1
- CYRMRQSGQSZIHP-UHFFFAOYSA-N n-[5-[5-(3,3-dimethylcyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(C)(C)C1 CYRMRQSGQSZIHP-UHFFFAOYSA-N 0.000 claims 1
- GBSLZTPHUKSUFS-UHFFFAOYSA-N n-[5-[5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1(O)C1CC1 GBSLZTPHUKSUFS-UHFFFAOYSA-N 0.000 claims 1
- ALCOLPSSMDCYTE-UHFFFAOYSA-N n-[5-[5-(3-ethoxyiminocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(=NOCC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 ALCOLPSSMDCYTE-UHFFFAOYSA-N 0.000 claims 1
- YGXKCHDRBDRTQD-UHFFFAOYSA-N n-[5-[5-(3-ethylcyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(CC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 YGXKCHDRBDRTQD-UHFFFAOYSA-N 0.000 claims 1
- NCSAWLWVPXOKBG-UHFFFAOYSA-N n-[5-[5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)C1 NCSAWLWVPXOKBG-UHFFFAOYSA-N 0.000 claims 1
- MADGFKMGRAUDJD-UHFFFAOYSA-N n-[5-[5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(F)C1 MADGFKMGRAUDJD-UHFFFAOYSA-N 0.000 claims 1
- LAMGHCHOPKUMQQ-UHFFFAOYSA-N n-[5-[5-(3-fluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)C1 LAMGHCHOPKUMQQ-UHFFFAOYSA-N 0.000 claims 1
- OOIDLNOVKHBOSA-UHFFFAOYSA-N n-[5-[5-(3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(O)C1 OOIDLNOVKHBOSA-UHFFFAOYSA-N 0.000 claims 1
- GQSZYLIKPYJHSF-UHFFFAOYSA-N n-[5-[5-(3-hydroxyiminocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(=NO)C1 GQSZYLIKPYJHSF-UHFFFAOYSA-N 0.000 claims 1
- MKRHTMICEQFIHC-UHFFFAOYSA-N n-[5-[5-(3-methoxycyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 MKRHTMICEQFIHC-UHFFFAOYSA-N 0.000 claims 1
- NQBZUPQOCMPGNT-UHFFFAOYSA-N n-[5-[5-(3-methoxyiminocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(=NOC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 NQBZUPQOCMPGNT-UHFFFAOYSA-N 0.000 claims 1
- BMCCLRYHDMTXEF-UHFFFAOYSA-N n-[5-[5-(4,4-difluorocyclohexyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CCC(F)(F)CC1 BMCCLRYHDMTXEF-UHFFFAOYSA-N 0.000 claims 1
- JUFRLPQXDIXLQH-UHFFFAOYSA-N n-[5-[5-(5,8-dioxaspiro[3.4]octan-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC21OCCO2 JUFRLPQXDIXLQH-UHFFFAOYSA-N 0.000 claims 1
- KXHHTSTVKBSBSY-UHFFFAOYSA-N n-[5-[5-(5,9-dioxaspiro[3.5]nonan-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC21OCCCO2 KXHHTSTVKBSBSY-UHFFFAOYSA-N 0.000 claims 1
- WMOJCMVDOZBWHB-UHFFFAOYSA-N n-[5-[5-(cyclopropylmethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CC1CC1 WMOJCMVDOZBWHB-UHFFFAOYSA-N 0.000 claims 1
- GZVKBICARWJUII-CQSZACIVSA-N n-[5-[5-[(1r)-2,2-difluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2,4-dimethylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC(C)=C1C(N=1)=NOC=1[C@H]1CC1(F)F GZVKBICARWJUII-CQSZACIVSA-N 0.000 claims 1
- KIRYEJRGNGQAGY-GJZGRUSLSA-N n-[5-[5-[(1r,2s)-2-fluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1[C@H]1C[C@@H]1F KIRYEJRGNGQAGY-GJZGRUSLSA-N 0.000 claims 1
- GZVKBICARWJUII-AWEZNQCLSA-N n-[5-[5-[(1s)-2,2-difluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2,4-dimethylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC(C)=C1C(N=1)=NOC=1[C@@H]1CC1(F)F GZVKBICARWJUII-AWEZNQCLSA-N 0.000 claims 1
- XSHQNNBDPNOIQS-AWEZNQCLSA-N n-[5-[5-[(1s)-2,2-difluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1[C@@H]1CC1(F)F XSHQNNBDPNOIQS-AWEZNQCLSA-N 0.000 claims 1
- KIRYEJRGNGQAGY-HUUCEWRRSA-N n-[5-[5-[(1s,2r)-2-fluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1[C@@H]1C[C@H]1F KIRYEJRGNGQAGY-HUUCEWRRSA-N 0.000 claims 1
- RHNJOZCVGSBEAG-KGLIPLIRSA-N n-[5-[5-[(1s,2s)-2-fluorocyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@@H]1C[C@@H]1F RHNJOZCVGSBEAG-KGLIPLIRSA-N 0.000 claims 1
- QNHNEQWNQVGZLK-QQXSKIMKSA-N n-[5-[5-[(3z)-3-hydroxyiminocyclopentyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC\C(=N\O)C1 QNHNEQWNQVGZLK-QQXSKIMKSA-N 0.000 claims 1
- KULAGCRXZBSVQY-PKAZHMFMSA-N n-[5-[5-[(3z)-3-methoxyiminocyclopentyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(=N/OC)\CCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 KULAGCRXZBSVQY-PKAZHMFMSA-N 0.000 claims 1
- TTXRVIZQMULATC-UHFFFAOYSA-N n-[5-[5-[1-(dimethylamino)cyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(N(C)C)CC1 TTXRVIZQMULATC-UHFFFAOYSA-N 0.000 claims 1
- FFZMQGTUGMGYIF-UHFFFAOYSA-N n-[5-[5-[1-(hydroxymethyl)cyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(CO)CC1 FFZMQGTUGMGYIF-UHFFFAOYSA-N 0.000 claims 1
- AUBYKKLQGKVMBE-UHFFFAOYSA-N n-[5-[5-[1-(methanesulfonamido)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(NS(C)(=O)=O)CCC1 AUBYKKLQGKVMBE-UHFFFAOYSA-N 0.000 claims 1
- LSYNSQSFZORUPT-UHFFFAOYSA-N n-[5-[5-[1-(methanesulfonamido)cyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(NS(C)(=O)=O)CC1 LSYNSQSFZORUPT-UHFFFAOYSA-N 0.000 claims 1
- PHEBMAJCJCVNAX-UHFFFAOYSA-N n-[5-[5-[1-(methoxymethyl)cyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(COC)CC1 PHEBMAJCJCVNAX-UHFFFAOYSA-N 0.000 claims 1
- CYBYWHSMZVHBDF-UHFFFAOYSA-N n-[5-[5-[1-[(2-methoxyacetyl)amino]cyclopropyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NOC=1C1(NC(=O)COC)CC1 CYBYWHSMZVHBDF-UHFFFAOYSA-N 0.000 claims 1
- KKVSEJYYZYNJTP-UHFFFAOYSA-N n-[5-[5-[2-(1-hydroxycyclopropyl)ethyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CCC1(O)CC1 KKVSEJYYZYNJTP-UHFFFAOYSA-N 0.000 claims 1
- WKGLUTLJDPODRX-UHFFFAOYSA-N n-[5-[5-[3-(2-methoxyethoxy)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OCCOC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 WKGLUTLJDPODRX-UHFFFAOYSA-N 0.000 claims 1
- UXHAQTBGPZMRBR-UHFFFAOYSA-N n-[5-[5-[3-(2-methoxyethylamino)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(NCCOC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 UXHAQTBGPZMRBR-UHFFFAOYSA-N 0.000 claims 1
- BWCMRRLLHHZFMK-UHFFFAOYSA-N n-[5-[5-[3-(3-hydroxypropylidene)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(=CCCO)C1 BWCMRRLLHHZFMK-UHFFFAOYSA-N 0.000 claims 1
- SJOBZOWGSQODEZ-UHFFFAOYSA-N n-[5-[5-[3-(cyclopropylmethoxyimino)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C(C1)CC1=NOCC1CC1 SJOBZOWGSQODEZ-UHFFFAOYSA-N 0.000 claims 1
- ILXSEWXTVYSAIV-UHFFFAOYSA-N n-[5-[5-[3-(methanesulfonamido)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(NS(C)(=O)=O)C1 ILXSEWXTVYSAIV-UHFFFAOYSA-N 0.000 claims 1
- NOMMXAAIKCBMRF-UHFFFAOYSA-N n-[5-[5-[3-hydroxy-3-(trifluoromethyl)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C)C=CN2C=1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1C1CC(O)(C(F)(F)F)C1 NOMMXAAIKCBMRF-UHFFFAOYSA-N 0.000 claims 1
- GSZAAFHRPAZVGN-UHFFFAOYSA-N n-[5-[5-[3-hydroxy-3-(trifluoromethyl)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(O)(C(F)(F)F)C1 GSZAAFHRPAZVGN-UHFFFAOYSA-N 0.000 claims 1
- VLIRSVBOVAFGHU-UHFFFAOYSA-N n-[5-[5-[3-methoxy-3-(trifluoromethyl)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-n-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OC)(C(F)(F)F)CC1C1=NC(C=2C=C(C(C)=CC=2)N(C)C(=O)C=2N3C=CC=CC3=NC=2)=NO1 VLIRSVBOVAFGHU-UHFFFAOYSA-N 0.000 claims 1
- PTEZEOLABNJMAJ-UHFFFAOYSA-N n-[5-[5-[3-methoxy-3-(trifluoromethyl)cyclobutyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OC)(C(F)(F)F)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 PTEZEOLABNJMAJ-UHFFFAOYSA-N 0.000 claims 1
- ILZBWSFFVJCHLO-UHFFFAOYSA-N n-[5-[5-[[(2,2-difluorocyclopropanecarbonyl)amino]methyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CNC(=O)C1CC1(F)F ILZBWSFFVJCHLO-UHFFFAOYSA-N 0.000 claims 1
- VWCUNZJDOSTKOT-UHFFFAOYSA-N n-[5-[5-[[(3,3-difluorocyclobutyl)amino]methyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1CNC1CC(F)(F)C1 VWCUNZJDOSTKOT-UHFFFAOYSA-N 0.000 claims 1
- 229960000470 omalizumab Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- QJSFAFPSJKXOAK-UHFFFAOYSA-N tert-butyl 3-[3-[[5-[5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]carbamoyl]imidazo[1,2-a]pyridin-6-yl]propanoate Chemical compound C1=C(NC(=O)C=2N3C=C(CCC(=O)OC(C)(C)C)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(F)(F)C1 QJSFAFPSJKXOAK-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- NJBRFGPVHWQELP-UHFFFAOYSA-N tert-butyl n-[1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(NC(=O)OC(C)(C)C)CCC1 NJBRFGPVHWQELP-UHFFFAOYSA-N 0.000 claims 1
- NSRLVENBQNMIER-UHFFFAOYSA-N tert-butyl n-[1-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclopropyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(NC(=O)OC(C)(C)C)CC1 NSRLVENBQNMIER-UHFFFAOYSA-N 0.000 claims 1
- FOMSBAZRUZJZMW-UHFFFAOYSA-N tert-butyl n-[3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]cyclobutyl]carbamate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CC(NC(=O)OC(C)(C)C)C1 FOMSBAZRUZJZMW-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
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- 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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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- Enzymes And Modification Thereof (AREA)
Claims (34)
1. Spoj, naznačen time, što je predstavljen s Formulom (I) ili Formulom (II), ili njegova farmaceutski prihvatljiva sol:
pri čemu:
m je 1 i R20 je odabran iz niza koji čine H, halo, C1-C6alkil, C1-C6haloalkil, C1-C6haloalkoksi, deuterij, deuterirani C1-C6alkil, -CN, -(CR92)nOR4, -C(O)R4, R10, -(CR92)nR10, -((CR92)nO)tR4, -(CR92)nO(CR92)nR7, -(CR92)nC(=O)R4, -C(=O)N(R4)2, -OR4 i -(CR92)nCN;
ili m je 4 i R20 je deuterij;
R1 je odabran iz niza koji čine C1-C6alkil i halo;
svaki R11 je neovisno odabran iz niza koji čine H, halo, i C1-C6alkil;
L1 je veza, -NH- ili -C(=O)NH-;
L2 je -(CR92)n-, -CHR6-, -(CR92)nO-, -NH-, -(CR92)nC(=O)-, -C(=O)O(CR92)n-, -(CR92)nOC(=O)NR4-, -(CR92)nNR4C(=O)(CR92)n-, -(CR92)nNR4C(=O)- ili -(CR92)nNR4C(=O)O-;
R2 je R3 ili L2R3;
R3 je odabran iz niza koji čine nesupstituirani C3-C8cikloalkil, ciklobutanon, ciklopentanon i supstituirani C3-C8cikloalkil,
pri čemu je supstituirani C3-C8cikloalkil od R3 supstituiran s 1-4 supstituenta koji su neovisno odabrani iz niza koji čine C1-C6alkil, halo, C1-C6haloalkil, -OR4, -CN, -C(=O)OR4, -C(=O)R4, -C(=O)R7, -C(=O)OR5, -(CR92)nOR4, -C(=O)O(CR92)nOR4, -N(R4)2, =N-OR4, =N-O-(CR92)nR5, -C(=O)NR42, -NR4C(=O)OR4, -NR4C(=O)(CR92)nOR4, -NR4(CR92)nOR4, -NR4S(=O)2R4, -N(C(=O)OR4)2, =CH2, =CH(CR92)nOR4, R8, -(CR92)nR8, deuterirani C1-C6alkoksi, -S(=O)2R4, -S(=O)2R7, -S(=O)2R8, -S(=O)2N(R4)2, -S(=O)2NHC(=O)OR4, -S(=O)2(CR92)nC(=O)OR4, -S(=O)2(CR92)nOR4, spiro priključen dioksolan, spiro priključen dioksolan koji je supstituiran s C1-C6alkilom, spiro priključen dioksan, spiro priključen tetrahidrofuranil, spiro priključen oksetan, spiro priključen ciklobutanon, spiro priključen ciklobutanol, C1 alkilni most, nesupstituirani 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O i S, 5-6-eročlanog heterocikloalkila s 1-2 heteroatoma koji su neovisno odabrani od N, O i S supstituirani s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila, halo, C1-C6haloalkila, C1-C6haloalkoksi, -OR4 i R8;
svaki R4 je neovisno odabran iz niza koji čine H i C1-C6alkil;
R5 je nesupstituirani C3-C8cikloalkil, nesupstituirani 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N ili O ili C3-C8cikloalkil supstituiran s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila;
svaki R6 je neovisno odabran iz niza koji čine -NHC(O)OR4, -OR4 i -(CR92)nOR4;
svaki R7 je neovisno odabran od C1-C6haloalkila;
R8 je odabran iz niza koji čine nesupstituirani fenil, nesupstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, nesupstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani C3-C8cikloalkil, supstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani fenil, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani C3-C8cikloalkil, oksazolidin-2-on, pirolidinon i pirolidin-2-on, pri čemu su supstituirani fenil, supstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani C3-C8cikloalkil i supstituirani 4-6-eročlani heterocikloalkil od R8, supstituirani s 1-3 supstituenta koji su neovisno odabrani od sljedećih: C1-C6alkil, -(C(R9)2)nOR4, -(C(R9)2)nR5, -(C(R9)2)nC(O)OR4, -C(O)OR4 i -S(O)2R4;
svaki R9 je neovisno odabran iz niza koji čine H i C1-C6alkil;
R10 je odabran iz niza koji čine nesupstituirani fenil, nesupstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani 5-eročlani heteroaril s 1-3 heteroatoma koji su odabrani od N, nesupstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani C3-C8cikloalkil, supstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani fenil, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani C3-C8cikloalkil, oksazolidin-2-on, pirolidinon i pirolidin-2-on, pri čemu su supstituirani fenil, supstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani C3-C8cikloalkil i supstituirani 4-6-eročlani heterocikloalkil od R10, supstituirani s 1-3 supstituenta koji su neovisno odabrani od sljedećih: C1-C6alkil, -(C(R9)2)nOR4, -(C(R9)2)nR5, -(C(R9)2)nC(O)OR4 i-S(O)2R4;
t je 1, 2 ili 3, i
svaki n je neovisno odabran iz niza koji čine 1, 2, 3 i 4.
2. Spoj prema zahtjevu 1, naznačen time, što spoj je spoj s Formulom (Ia), Formulom (IIa), Formulom (Ib) ili Formulom (IIb):
pri čemu:
m je 1 i R20 je odabran iz niza koji čine H, halo, C1-C6alkil, C1-C6haloalkil, C1-C6haloalkoksi, deuterij, deuterirani C1-C6alkil, -CN, -(CR92)nOR4, -C(O)R4, R10, -(CR92)nR10, -((CR92)nO)tR4, -(CR92)nO(CR92)nR7, -(CR92)nC(=O)R4, -C(=O)N(R4)2, -OR4 i -(CR92)nCN;
ili m je 4 i R20 je deuterij;
R1 je odabran iz niza koji čine C1-C6alkil i halo;
svaki R11 je neovisno odabran iz niza koji čine H, halo, i C1-C6alkil;
L2 je -(CR92)n-, -CHR6-, -(CR92)nO-, -NH-, -(CR92)nC(=O)-, -C(=O)O(CR92)n-, -(CR92)nOC(=O)NR4-, -(CR92)nNR4C(=O)(CR92)n-, -(CR92)nNR4C(=O)- ili -(CR92)nNR4C(=O)O-;
R2 je R3 ili L2R3;
R3 je odabran iz niza koji čine nesupstituirani C3-C8cikloalkil, ciklobutanon, ciklopentanon i supstituirani C3-C8cikloalkil,
pri čemu supstituirani C3-C8cikloalkil od R3 je supstituiran s 1-4 supstituenta koji su neovisno odabrani iz niza koji čine C1-C6alkil, halo, C1-C6haloalkil, -OR4, -CN, -C(=O)OR4, -C(=O)R4, -C(=O)R7, -C(=O)OR5, -(CR92)nOR4, -C(=O)O(CR92)nOR4, -N(R4)2, =N-OR4, =N-O-(CR92)nR5, -C(=O)NR42, -NR4C(=O)OR4, -NR4C(=O)(CR92)nOR4, -NR4(CR92)nOR4, -NR4S(=O)2R4, -N(C(=O)OR4)2, =CH2, =CH(CR92)nOR4, R8, -(CR92)nR8, deuterirani C1-C6alkoksi, -S(=O)2R4, -S(=O)2R7, -S(=O)2R8, -S(=O)2N(R4)2, -S(=O)2NHC(=O)OR4, -S(=O)2(CR92)nC(=O)OR4, -S(=O)2(CR92)nOR4, spiro priključen dioksolan, spiro priključen dioksolan koji je supstituiran s C1-C6alkilom, spiro priključen dioksan, spiro priključen tetrahidrofuranil, spiro priključen oksetan, spiro priključen ciklobutanon, spiro priključen ciklobutanol, C1 alkilni most, nesupstituirani 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O i S, 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O i S supstituiran s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila, halo, C1-C6haloalkila, C1-C6haloalkoksi, -OR4 i R8;
svaki R4 je neovisno odabran iz niza koji čine H i C1-C6alkil;
R5 je nesupstituirani C3-C8cikloalkil, nesupstituirani 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N ili O ili C3-C8cikloalkil supstituiran s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila;
svaki R6 je neovisno odabran iz niza koji čine -NHC(O)OR4, -OR4 i -(CR92)nOR4;
svaki R7 je neovisno odabranod C1-C6haloalkila;
R8 je odabran iz niza koji čine nesupstituirani fenil, nesupstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, nesupstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani C3-C8cikloalkil, supstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani fenil, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani C3-C8cikloalkil, oksazolidin-2-on, pirolidinon i pirolidin-2-on, pri čemu su supstituirani fenil, supstituirani 5-6-eročlani heteroaril s 1-3 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani C3-C8cikloalkil i supstituirani 4-6-eročlani heterocikloalkil od R8, supstituirani s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila, -(C(R9)2)nOR4, -(C(R9)2)nR5, -(C(R9)2)nC(O)OR4, -C(O)OR4 i-S(O)2R4;
svaki R9 je neovisno odabran iz niza koji čine H i C1-C6alkil;
R10 je odabran iz niza koji čine nesupstituirani fenil, nesupstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani 5-eročlani heteroaril s 1-3 heteroatoma koji su odabrani od N, nesupstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, nesupstituirani C3-C8cikloalkil, supstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani fenil, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani 4-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani C3-C8cikloalkil, oksazolidin-2-on, pirolidinon i pirolidin-2-on, pri čemu su supstituirani fenil, supstituirani 5-6-eročlani heteroaril s 1-2 heteroatoma koji su neovisno odabrani od N, O ili S, supstituirani 5-eročlani heteroaril s 1-4 heteroatoma koji su odabrani od N, supstituirani C3-C8cikloalkil i supstituirani 4-6-eročlani heterocikloalkil od R10, supstituirani s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila, -(C(R9)2)nOR4, -(C(R9)2)nR5, -(C(R9)2)nC(O)OR4 i-S(O)2R4;
t je 1, 2 ili 3, i
svaki n je neovisno odabran iz niza koji čine 1, 2, 3 i 4.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time, što je R1 odabran iz niza koji čine -CH3 i F.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, što R1 je -CH3.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, što je svaki R11 neovisno odabran iz niza koji čine H, F i -CH3.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time, što svaki R11 je H.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, što je R3 odabran iz niza koji čine nesupstituirani C3-C8cikloalkil, ciklobutanon, ciklopentanon i supstituirani C3-C8cikloalkil,
pri čemu je supstituirani C3-C8cikloalkil od R3, supstituiran s 1-4 supstituenta koji su neovisno odabrani iz niza koji sadrži C1-C6alkil, halo, C1-C6haloalkil, -OR4, -(CR92)nOR4, -N(R4)2, =N-OR4, =N-O-(CR92)nR5, -NR4C(=O)OR4, -NR4C(=O)(CR92)nOR4, -NR4(CR92)nOR4, -NR4S(=O)2R4, -N(C(=O)OR4)2, =CH2, =CH(CR92)nOR4, R8, deuterirani C1-C6alkoksi, spiro priključen dioksolan, spiro priključen dioksolan koji je supstituiran s C1-C6alkil, spiro priključen dioksan, spiro priključen tetrahidrofuranil, spiro priključen ciklobutanon, spiro priključenciklobutanol, nesupstituirani 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N i O i 5-6-eročlani heterocikloalkil s 1-2 heteroatoma koji su neovisno odabrani od N i O supstituiran s 1-3 supstituenta koji su neovisno odabrani od C1-C6alkila.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, što je svaki R4 neovisno odabran iz niza koji čine H, metil, etil, propil, butil, i-propil i t-butil.
9. Spoj prema bilo kojem od zahtjeva 1 do 8, naznačen time, što R5 je neovisno odabran iz niza koji čine ciklopropil ili morfolinil.
10. Spoj prema bilo kojem od zahtjeva 1 do 9, naznačen time, što je svaki R7 neovisno odabran iz niza koji čine CH2F, -CHF2, -CH2CHF2, -CH2CF3 i -CF3.
11. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, što je svaki R9 neovisno odabran iz niza koji čine H, metil i etil.
12. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time, što R8 je odabran iz niza koji čine nesupstituirani C3-C8cikloalkil i nesupstituirani 5-teročlani heteroaril s 1-4 heteroatoma koji su odabrani od N.
13. Spoj prema bilo kojem od zahtjeva 1 do 12, naznačen time, što
R3 je odabran iz niza koji čine ciklopropil, ciklobutil, ciklopentil i cikloheksil, od kojih je svaki nesupstituiran ili od kojih je svaki supstituiran s 1-4 supstituenta koji su neovisno odabrani od -F, -CH3, -CH2CH3, -CF3, -OH, -OCH3, -CH2OCH3, -NH2, -N(CH3)2, =N-OCH3, =N-OCH2CH3, =N-OCH(CH3)2, =N-OH, =N-O-CH2R5, =N-O-CH2CH2R5, -NHC(=O)OC(CH3)3, -NHC(=O)OCH3, -NHC(=O)CH2OCH3, -NHCH2CH2OCH3, -NHCH2CH2OH, -NHS(=O)2CH3, -N(C(=O)OCH3)2, =CH2, =CHCH2CH2OH, -OCD3, ciklopropil, triazolil, pirazolil, spiro priključen dioksolan, spiro priključen dioksolan koji je supstituiran s -CH3, spiro priključen dioksan, spiro priključen tetrahidrofuranil, spiro priključen ciklobutanon, spiro vezan ciklobutanol, piperidinil i piperazinil supstituiran s -CH3,
ili R3 je ciklobutanon ili ciklopentanon.
14. Spoj prema bilo kojem od zahtjeva 1 do 13, naznačen time, što:
R3 je ciklopropil supstituiran s 1 ili 2 F,
ili
R3 je ciklobutil supstituiran s 2 F.
15. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, što m je 1 i R20 je odabran iz niza koji čine H, halo, C1-C6alkil, C1-C6haloalkil, C1-C6haloalkoksi, deuterirani C1-C6alkil, -CN, -(CR92)nOR4, R10, -(CR92)nR10, -((CR92)nO)tR4, -(CR92)nO(CR92)nR7, -(CR92)nC(=O)R4, i -C(=O)N(R4)2.
16. Spoj prema bilo kojem od zahtjeva 1 do 15, naznačen time, što m je 1 i R20 je odabran iz niza koji čine H, -F, -CH3, -CF3, -CD3, -CN, -OCHF2, -C(CH3)OH, -CH2OCH2CH2OH, -CH2OCH2CF3, -C(=O)NH2, -CH2CH2C(CH3)2OH, -CH2OCH2CH2OCH3, -CH2OCH2CH2F, -CH2CH2C(=O)CH3, -CH2OH i -CH2OCH3.
17. Spoj prema bilo kojem od zahtjeva 1 do 16, naznačen time, što m je 1 i R20 je -CH3.
18. Spoj prema bilo kojem od zahtjeva 1 do 16, naznačen time, što m je 1 i R20 je H.
19. Spoj prema bilo kojem od zahtjeva 1 do 18, naznačen time, što:
R10 je odabran iz niza koji čine morfolinil, piperidinil, piperidin-1-il, piperidin-2-il, piperidin-3-il, piperidin-4-il, piperazinil, piperazin-1-il, pirazolil, pirazol-1-il, pirazol-3-il, pirazol-4-il, triazolil, 1H-1,2,3-triazol-4-il, 4H-1,2,4-triazol-3-il, 1H-1,2,4-triazol-5-il, tiazolil, tiazol-4-il, tiazol-5-il, imidazolil, imidazol-1-il, imidazol-2-il, od kojih je svaki nesupstituiran ili od kojih je svaki supstituiran s 1-3 supstituenta koji su neovisno odabrani iz niza koji čine C1-C6alkil, -(CR92)nOR4, -(C(R9)2)nC(O)OR4, -(C(R9)2)nR5 i -S(=O)2R4,
ili R10 je odabran iz niza koji čine oksazolidin-2-on i pirolidin-2-on.
20. Spoj prema bilo kojem od zahtjeva 1 do 19, naznačen time, što:
R10 je odabran iz niza koji čine morfolinil, piperidinil, piperidin-1-il, piperidin-2-il, piperidin-3-il, piperidin-4-il, piperazinil, piperazin-1-il, pirazolil, pirazol-1-il, pirazol-3-il, pirazol-4-il, triazolil, 1H-1,2,3-triazol-4-il, 4H-1,2,4-triazol-3-il, 1H-1,2,4-triazol-5-il, tiazolil, tiazol-4-il, tiazol-5-il, imidazolil, imidazol-1-il, imidazol-2-il, od kojih je svaki nesupstituiran ili od kojih je svaki supstituiran s 1-3 supstituenta koji su neovisno odabrani iz niza koji čine -CH3, -CH2CH2OH, -CH2C(O)OH, -CH2CH2OH, -CH2C(CH3)2OH, -S(O)2CH3 i -CH2CH2-R5.
21. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, što m je 4 i R20 je deuterij.
22. Spoj prema zahtjevu 1, naznačen time, što je odabran iz niza koji sadrži:
N-{5-[3-(3,3-difluorociklobutil)-1,2,4-oksadiazol-5-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{2-metil-5-[5-(3-oksociklopentil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-hidroksi-3-metilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-(hidroksiimino)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(4,4-difluorocikloheksil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-hidroksi-3-metilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-(metoksiimino)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{5,8-dioksaspiro[3.4]oktan-2-il}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[(6R)-6-metil-5,8-dioksaspiro[3.4]oktan-2-il]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{5,9-dioksaspiro[3.5]nonan-2-il}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{2-metil-5-[5-(3-oksociklobutil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[(6S)-6-metil-5,8-dioksaspiro[3.4]oktan-2-il]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-(etoksiimino)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{3-[(ciklopropilmetoksi)imino]ciklobutil}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-[2-metil-5-(5-{3-[(propan-2-iloksi)imino]ciklobutil}-1,2,4-oksadiazol-3-il)fenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-aminociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-metoksiciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[1-(metoksimetil)ciklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
tert-butil N-{1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklopropil}karbamat;
N-{5-[5-(1-metansulfonamidociklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
metil N-{1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklopropil}-N-(metoksikarbonil)karbamat;
metil N-{1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklopropil}karbamat;
N-(5-{5-[3-hidroksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
1-metilciklopropil N-{[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]metil}karbamat;
metil N-{1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
N-{5-[5-(1-metansulfonamidociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[1-(dimetilamino)ciklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{2-metil-5-[5-(3-metilidenciklobutil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-ciklopropil-3-hidroksiciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-(3-hidroksipropiliden)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[2-metil-5-(5-{5-oksaspiro[3.4]oktan-2-il}-1,2,4-oksadiazol-3-il)fenil]imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{[(3,3-difluorociklobutil)amino]metil}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[(2,2,3,3-tetrafluorociklobutoksi)metil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-fluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(hidroksimetil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-hidroksietoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(metoksimetil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1H-pirazol-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[1-(2-hidroksietil)-1H-pirazol-4-il]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1-metil-1H-pirazol-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1-metil-1H-pirazol-3-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[1-(2-hidroksi-2-metilpropil)-1H-pirazol-4-il]imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[3-(1H-pirazol-1-il)ciklobutil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1,3-tiazol-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}-6-(1-metil-1H-pirazol-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}-6-[1-(2-hidroksi-2-metilpropil)-1H-pirazol-4-il]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(1-metansulfonilpiperidin-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-{1-[2-(morfolin-4-il)etil]-1H-pirazol-4-il}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}-6-{1-[2-(morfolin-4-il)etil]-1H-pirazol-4-il}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2,2,2-trifluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(3-oksobutil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(3-hidroksi-3-metilbutil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[2-(1-hidroksiciklopropil)etil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[2-(morfolin-4-il)etil]imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-ciklobutil-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-dimetilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(morfolin-4-il)imidazo[1,2-a]piridin-3-karboksamid;
6-cijano-N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}-6-(5-metil-4H-1,2,4-triazol-3-il)imidazo[1,2-a]piridin-3-karboksamid;
3-N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3,6-dikarboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[2-(4-metilpiperazin-1-il)etil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(2,2-difluorociklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(1H-1,2,3-triazol-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-[1-(2-hidroksietil)-1H-1,2,3-triazol-4-il]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2,4-dimetilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(2-okso-1,3-oksazolidin-3-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-metilimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-fluoroimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-fluoroimidazo[1,2-a]piridin-3-karboksamid;
7-cijano-N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-ciklopentil-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-[2-metil-5-(5-{6-oksospiro[3.3]heptan-2-il}-1,2,4-oksadiazol-3-il)fenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(2-oksopirolidin-1-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2,2-difluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-etilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(5-metil-4H-1,2,4-triazol-3-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(morfolin-4-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1H-imidazol-1-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-fluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[3-(metoksimetil)-1H-1,2,4-triazol-5-il]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(2,2-difluorociklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2,2,2-trifluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-ciklobutil-1,2,4-oksadiazol-3-il)-2-metilfenil]-6-[(2,2,2-trifluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-hidroksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)-7-metilimidazo[1,2-a]piridin-3-karboksamid;
6-fluoro-N-(5-{5-[3-hidroksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R,2S)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-5,6,7,8-tetradeuteroimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[(3,3-difluorociklobutil)karbamoil]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
7-fluoro-N-(5-{5-[3-hidroksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(4-metil-1H-imidazol-1-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2R,6S)-2,6-dimetilmorfolin-4-il]imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-metoksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
6-fluoro-N-(5-{5-[1-(metoksimetil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[1-(2-metoksietil)-5-metil-1H-1,2,4-triazol-3-il]imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{6-hidroksispiro[3.3]heptan-2-il}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S,2S)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
7-metil-N-(2-metil-5-{5-[(2,2,3,3-tetrafluorociklobutoksi)metil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
6-metil-N-(2-metil-5-{5-[(2,2,3,3-tetrafluorociklobutoksi)metil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-ciklopropil-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(ciklopropilmetil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R,2S)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S,2R)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2,4-dimetilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2,4-dimetilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R,2S)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-fluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-fluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-metilimidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S,2R)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
metil N-{3,3-difluoro-1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
metil N-{3,3-difluoro-1-[3-(4-metil-3-{7-metilimidazo[1,2-a]piridin-3-amido}fenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-fluoroetoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(3-ciklopropil-1,2,4-oksadiazol-5-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,3,4-oksadiazol-2-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-hidroksi-3-metilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(3Z)-3-(metoksiimino)ciklopentil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(3Z)-3-(hidroksiimino)ciklopentil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[1-(trifluorometil)ciklopropil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-hidroksi-3-metilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{2-metil-5-[5-(3-oksociklobutil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-hidroksiciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[3-(piperidin-1-il)ciklobutil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[3-(morfolin-4-il)ciklobutil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[3-(4-metilpiperazin-1-il)ciklobutil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
N-{2-metil-5-[5-(3-{[2-(morfolin-4-il)etoksi]imino}ciklobutil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
tert-butil N-{3-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
N-{5-[5-(3-aminociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3-metansulfonamidociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
1-metilciklopropil N-{2-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]etil}karbamat;
N-{5-[5-(1-aminociklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[1-(2-metoksiacetamido)ciklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{3-[(2-metoksietil)amino]ciklobutil}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[3-metoksi-3-(trifluorometil)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)-N-metilimidazo[1,2-a]piridin-3-karboksamid;
tert-butil N-{1-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
N-{5-[5-(1-aminociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{2-fluoro-5-[5-(3-metilidenciklobutil)-1,2,4-oksadiazol-3-il]fenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[1-(hidroksimetil)ciklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-{[(2,2-difluorociklopropil)formamido]metil}-1,2,4-oksadiazol-3-il)-2-metilfenil]imidazo[1,2-a]piridin-3-karboksamid;
1-metilciklopropil N-[(3-{4-metil-3-[7-(trifluorometil)imidazo[1,2-a]piridin-3-amido]fenil}-1,2,4-oksadiazol-5-il)metil]karbamat;
metil N-{3-[3-(3-{imidazo[1,2-a]piridin-3-amido}-4-metilfenil)-1,2,4-oksadiazol-5-il]ciklobutil}karbamat;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(4-metilpiperazin-1-il)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-{[4-(2-hidroksietil)piperazin-1-il]metil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-metoksietoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
2-{4-[3-({5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}karbamoil)imidazo[1,2-a]piridin-6-il]-1H-pirazol-1-il}octena kiselina;
N-{5-[5-(1-hidroksiciklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(difluorometoksi)imidazo[1,2-a]piridin-3-karboksamid;
N-(2-metil-5-{5-[3-(1H-1,2,4-triazol-1-il)ciklobutil]-1,2,4-oksadiazol-3-il}fenil)imidazo[1,2-a]piridin-3-karboksamid;
6-fluoro-N-{5-[5-(3-hidroksiciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-[5-(5-ciklobutil-1,2,4-oksadiazol-3-il)-2-fluorofenil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(2-hidroksi-2-metilpropil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-okso-1,3-oksazolidin-3-il)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(2-hidroksi-2-metilpropil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-dimetilciklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-fluorofenil}-6-(5-metil-4H-1,2,4-triazol-3-il)imidazo[1,2-a]piridin-3-karboksamid;
6-fluoro-N-{5-[5-(3-hidroksi-3-metilciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(2-hidroksiciklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{3-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2,6-dimetilfenil}imidazo[1,2-a]piridin-3-karboksamid;
7-cijano-N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(1-hidroksietil)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-(5-metil-1H-imidazol-1-il)imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-[(2-metoksietoksi)metil]imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)-7-metilimidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(1-fluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(1-hidroksiciklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-{5-[5-(1-karbamoilciklopropil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-6-fluoroimidazo[1,2-a]piridin-3-karboksamid i
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}-7-(piperidin-4-il)imidazo[1,2-a]piridin-3-karboksamid.
23. Spoj prema zahtjevu 1, naznačen time, što je odabran iz niza koji čine:
N-{5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1R)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S)-2,2-difluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid;
N-(5-{5-[(1S,2R)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid, i
N-(5-{5-[(1R,2S)-2-fluorociklopropil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid.
24. Spoj, naznačen time, što je odabran iz niza koji čine:
N-(5-{5-[3-(2-metoksietoksi)ciklobutil]-1,2,4-oksadiazol-3-il}-2-metilfenil)imidazo[1,2-a]piridin-3-karboksamid, i
tert-butil 3-[3-({5-[5-(3,3-difluorociklobutil)-1,2,4-oksadiazol-3-il]-2-metilfenil}karbamoil)imidazo[1,2-a]piridin-6-il]propanoat.
25. Farmaceutski pripravak, naznačen time, što sadrži terapeutski učinkovitu količinu spoja prema bilo kojem od zahtjeva 1 do 24 i farmaceutski prihvatljiv nosač.
26. Spoj prema bilo kojem od zahtjeva 1 do 24, naznačen time, što je za uporabu u terapiji.
27. Spoj prema bilo kojem od zahtjeva 1 do 24, naznačen time, što je za uporabu u liječenju bolesti posredovane s kinazom koja je odabrana od c-kit, PDGFRα, i PDGFRβ, pri čemu bolest je respiratorna bolest, upalni poremećaj, sindrom iritabilnog crijeva (IBS), upalna bolest crijeva (IBD), autoimuni poremećaj, metabolička bolest, fibrozna bolest, dermatološka bolest, plućna arterijska hipertenzija (PAH) ili primarna plućna hipertenzija (PPH).
28. Spoj za uporabu prema zahtjevu 27, naznačen time, što bolest je astma, alergijski rinitis, plućna arterijska hipertenzija (PAH), plućna fibroza, fibroza jetre, kardijalna fibroza, sklerodermija, sindrom iritabilnog crijeva (IBS), upalna bolest crijeva (IBD), urtikarija, atopijski dermatitis, alergijski kontaktni dermatitis, reumatoidni artritis, multipla skleroza, melanom, gastrointestinalni stromalni tumor, tumor mastocita, mastocitoza, anafilaktički sindrom, dermatoza, Crohnova bolest, dijabetes tipa I ili dijabetes tipa II.
29. Spoj koji ima Formulu (I) ili Formulu (II) prema bilo kojem od zahtjeva 1 do 24, ili njegova farmaceutski prihvatljiva sol, naznačen time, što je za uporabu u kombinaciji s terapeutski učinkovitom količinom drugog sredstva, za uporabu u liječenju bolesti ili stanja koje je modulirano s aktivnošću kinaze, naročito c-kit, ili c-kit i PDGFR (α i β), pri čemu bolest je bolest povezana s mastocitima, respiratorna bolest, upalni poremećaj, sindrom iritabilnog crijeva (IBS), upalna bolest crijeva (IBD), autoimuni poremećaj, metabolička bolest, fibrozna bolest, dermatološka bolest, plućna arterijska hipertenzija (PAH) ili primarna plućna hipertenzija (PPH).
30. Najmanje jedan spoj s Formulom (I) ili Formulom (II) prema bilo kojem od zahtjeva 1 do 24, ili njegova farmaceutski prihvatljiva sol, naznačen time, što je za uporabu u kombinaciji s drugim terapeutskim sredstvom koje obuhvaća antiemetike, protuupalna sredstva, imunomodulacijska sredstva, citokine, antidepresive, hormone, alkilirajuća sredstva, antimetabolite, antitumorske antibiotike, antimitotička sredstva, inhibitore topoizomeraze, citostatička sredstva, anti-invazivna sredstva, antiangiogena sredstva, inhibitore funkcije čimbenika rasta, antikancerogena sredstva i modulatore toll-u sličnih receptora.
31. Spoj s Formulom (I) ili Formulom (II) prema bilo kojem od zahtjeva 1 do 24, ili njegova farmaceutski prihvatljiva sol, naznačen time, što je za uporabu u kombinaciji s drugim terapeutskim sredstvom, za uporabu u liječenju astme, pri čemu drugo terapeutsko sredstvo je bronhodilatator, protuupalno sredstvo, antagonist leukotriena, ili blokator IgE.
32. Kombinacija, naznačena time, što je od spoja s Formulom (I) ili Formulom (II), prema bilo kojem od zahtjeva 1 do 24, ili njegove farmaceutski prihvatljive soli, s imunoglobulinom (Ig), gama globulinom, Ig pripravkom ili antagonistom ili protutijelom koje modulira Ig funkciju odabranom od anti-IgE, naročito s omalizumabom.
33. Spoj s Formulom (I) ili Formulom (II) prema bilo kojem od zahtjeva 1 do 24, ili njegova farmaceutski prihvatljiva sol, naznačen time, što je za uporabu u kombinaciji s drugim terapeutskim sredstvom za liječenje astme.
34. Spoj s Formulom (I) ili Formulom (II) za uporabu u kombinaciji za uporabu prema zahtjevu 29, 31 ili 33, spoj s Formulom (I) ili Formulom (II) za uporabu u kombinaciji s dodatnim terapeutskim sredstvom prema zahtjevu 30, ili kombinacija prema zahtjevu 32, naznačeni time, što je kombinacija ne-fiksna kombinacija.
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