JP6134319B2 - ｃ−ｋｉｔキナーゼインヒビターとしての化合物及び組成物 - Google Patents

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Publication number

JP6134319B2

JP6134319B2 JP2014528537A JP2014528537A JP6134319B2 JP 6134319 B2 JP6134319 B2 JP 6134319B2 JP 2014528537 A JP2014528537 A JP 2014528537A JP 2014528537 A JP2014528537 A JP 2014528537A JP 6134319 B2 JP6134319 B2 JP 6134319B2

Authority

JP

Japan

Prior art keywords

imidazo

oxadiazol

pyridine

methyl

methylphenyl

Prior art date

2011-09-01

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims description 325
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 title claims description 138
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 title claims description 137
• 239000000203 mixture Substances 0.000 title description 95
• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 289
• 125000005842 heteroatom Chemical group 0.000 claims description 276
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 190
• 229910052760 oxygen Inorganic materials 0.000 claims description 160
• 229910052717 sulfur Inorganic materials 0.000 claims description 148
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 128
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 126
• 201000010099 disease Diseases 0.000 claims description 118
• 150000003839 salts Chemical class 0.000 claims description 100
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 92
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 89
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 78
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 78
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 76
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 72
• 239000008194 pharmaceutical composition Substances 0.000 claims description 70
• 125000003003 spiro group Chemical group 0.000 claims description 65
• 208000035475 disorder Diseases 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 210000003630 histaminocyte Anatomy 0.000 claims description 59
• 208000006673 asthma Diseases 0.000 claims description 56
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 50
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 47
• KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 46
• 229910052805 deuterium Inorganic materials 0.000 claims description 43
• 239000003814 drug Substances 0.000 claims description 43
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 41
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 38
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 37
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 37
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 36
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 34
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• 108091000080 Phosphotransferase Proteins 0.000 claims description 29
• 102000020233 phosphotransferase Human genes 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 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 description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
• 208000017520 skin disease Diseases 0.000 claims description 23
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 22
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 210000004072 lung Anatomy 0.000 claims description 21
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 208000027866 inflammatory disease Diseases 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 19
• 206010016654 Fibrosis Diseases 0.000 claims description 18
• 208000023504 respiratory system disease Diseases 0.000 claims description 18
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 18
• 208000023275 Autoimmune disease Diseases 0.000 claims description 17
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 17
• 230000004761 fibrosis Effects 0.000 claims description 17
• 201000010105 allergic rhinitis Diseases 0.000 claims description 15
• 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims description 14
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 14
• 208000024780 Urticaria Diseases 0.000 claims description 14
• 201000008312 primary pulmonary hypertension Diseases 0.000 claims description 14
• 206010039710 Scleroderma Diseases 0.000 claims description 13
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 13
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 12
• 208000030159 metabolic disease Diseases 0.000 claims description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
• 241001377010 Pila Species 0.000 claims description 11
• SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims description 11
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 11
• 208000011580 syndromic disease Diseases 0.000 claims description 11
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
• 150000003857 carboxamides Chemical class 0.000 claims description 10
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 10
• RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 230000002685 pulmonary effect Effects 0.000 claims description 10
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 10
• WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 10
• 201000008937 atopic dermatitis Diseases 0.000 claims description 9
• 230000009787 cardiac fibrosis Effects 0.000 claims description 9
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 208000008585 mastocytosis Diseases 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 201000006417 multiple sclerosis Diseases 0.000 claims description 9
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 8
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 8
• 208000010668 atopic eczema Diseases 0.000 claims description 8
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 8
• 201000006512 mast cell neoplasm Diseases 0.000 claims description 8
• 208000006971 mastocytoma Diseases 0.000 claims description 8
• 201000001441 melanoma Diseases 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
• 235000005152 nicotinamide Nutrition 0.000 claims description 7
• 239000011570 nicotinamide Substances 0.000 claims description 7
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 7
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 7
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 6
• 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 description 6
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 206010002198 Anaphylactic reaction Diseases 0.000 claims description 5
• 230000036783 anaphylactic response Effects 0.000 claims description 5
• 208000003455 anaphylaxis Diseases 0.000 claims description 5
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 4
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
• BVOKCPFFOMTVIU-HOTGVXAUSA-N n-[2-methyl-5-[3-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1,2,4-oxadiazol-5-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)NC=3C(C)=CC=C(C=3)C=3ON=C(N=3)N3C[C@]4(OC[C@]3([H])C4)[H])=CN=C21 BVOKCPFFOMTVIU-HOTGVXAUSA-N 0.000 claims description 4
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 3
• MWXZOMGJPNSSFF-UHFFFAOYSA-N n-[5-[5-(azetidin-1-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=1N1CCC1 MWXZOMGJPNSSFF-UHFFFAOYSA-N 0.000 claims description 3
• GCOVDDPKAASSGO-UHFFFAOYSA-N n-[5-[5-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]-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=1N1CC(O)(C(F)(F)F)C1 GCOVDDPKAASSGO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• 125000003566 oxetanyl group Chemical group 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• SWKVQJQPSGTEBD-UHFFFAOYSA-N 1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyrazin-3-one Chemical compound C1NCCN2C(=O)OCC21 SWKVQJQPSGTEBD-UHFFFAOYSA-N 0.000 claims description 2
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
• AOHALMNASANBSM-UHFFFAOYSA-N 7-fluoro-n-[2-methyl-5-[5-(oxan-4-ylamino)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[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=1NC1CCOCC1 AOHALMNASANBSM-UHFFFAOYSA-N 0.000 claims description 2
• 206010020772 Hypertension Diseases 0.000 claims description 2
• XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 2
• 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• NHRVCOZRKRYCOO-UHFFFAOYSA-N n-[2-fluoro-5-[5-(1-methylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 NHRVCOZRKRYCOO-UHFFFAOYSA-N 0.000 claims description 2
• UBSQBYGTFVGXKA-UHFFFAOYSA-N n-[2-fluoro-5-[5-(morpholin-4-ylmethyl)-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=1CN1CCOCC1 UBSQBYGTFVGXKA-UHFFFAOYSA-N 0.000 claims description 2
• RMUUCNOTIRFOEI-UHFFFAOYSA-N n-[2-fluoro-5-[5-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)C1 RMUUCNOTIRFOEI-UHFFFAOYSA-N 0.000 claims description 2
• OYXCJSPRMZJDFF-UHFFFAOYSA-N n-[2-methyl-5-(5-piperidin-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=1C1CCCCN1 OYXCJSPRMZJDFF-UHFFFAOYSA-N 0.000 claims description 2
• LQOTVAKVQIEKQI-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-methylsulfonylazetidin-3-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=1C1CN(S(C)(=O)=O)C1 LQOTVAKVQIEKQI-UHFFFAOYSA-N 0.000 claims description 2
• PBHHQRZQACROTO-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-methylsulfonylpiperidin-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=1C1CCCCN1S(C)(=O)=O PBHHQRZQACROTO-UHFFFAOYSA-N 0.000 claims description 2
• NZAIURJHLBSEAO-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-methylsulfonylpiperidin-4-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=1C1CCN(S(C)(=O)=O)CC1 NZAIURJHLBSEAO-UHFFFAOYSA-N 0.000 claims description 2
• CTXVOEZUXMLNEE-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-methylsulfonylpyrrolidin-3-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=1C1CCN(S(C)(=O)=O)C1 CTXVOEZUXMLNEE-UHFFFAOYSA-N 0.000 claims description 2
• LQDSGDMSYGDLMS-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-propylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CCC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 LQDSGDMSYGDLMS-UHFFFAOYSA-N 0.000 claims description 2
• FXFFTFWUFQDIOW-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-pyridin-3-ylsulfonylazetidin-3-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)CN1S(=O)(=O)C1=CC=CN=C1 FXFFTFWUFQDIOW-UHFFFAOYSA-N 0.000 claims description 2
• ZUXSOTOVKZQNSA-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-sulfamoylazetidin-3-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=1C1CN(S(N)(=O)=O)C1 ZUXSOTOVKZQNSA-UHFFFAOYSA-N 0.000 claims description 2
• SYTQGVZRXBTUHK-UHFFFAOYSA-N n-[2-methyl-5-[5-(2-morpholin-4-ylethyl)-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=1CCN1CCOCC1 SYTQGVZRXBTUHK-UHFFFAOYSA-N 0.000 claims description 2
• WYCBIKKSHFRJFM-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-methyl-1-methylsulfonylazetidin-3-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=1C1(C)CN(S(C)(=O)=O)C1 WYCBIKKSHFRJFM-UHFFFAOYSA-N 0.000 claims description 2
• LMWMYUZLVKZUOK-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-morpholin-4-yl-3-oxopropyl)-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=1CCC(=O)N1CCOCC1 LMWMYUZLVKZUOK-UHFFFAOYSA-N 0.000 claims description 2
• UDTPTAWMXPFZGM-UHFFFAOYSA-N n-[2-methyl-5-[5-(3-morpholin-4-ylpropyl)-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=1CCCN1CCOCC1 UDTPTAWMXPFZGM-UHFFFAOYSA-N 0.000 claims description 2
• IRRMDYCTKFSGNA-UHFFFAOYSA-N n-[2-methyl-5-[5-(4-methylsulfonylmorpholin-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=1C1CN(S(C)(=O)=O)CCO1 IRRMDYCTKFSGNA-UHFFFAOYSA-N 0.000 claims description 2
• NHDBVPQWNCRZMB-UHFFFAOYSA-N n-[2-methyl-5-[5-(morpholin-4-ylmethyl)-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=1CN1CCOCC1 NHDBVPQWNCRZMB-UHFFFAOYSA-N 0.000 claims description 2
• SOLZCXWFZYEDAD-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxan-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=1C1CCCCO1 SOLZCXWFZYEDAD-UHFFFAOYSA-N 0.000 claims description 2
• YVGRSBSCXXFGMP-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxan-2-ylmethyl)-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=1CC1CCCCO1 YVGRSBSCXXFGMP-UHFFFAOYSA-N 0.000 claims description 2
• YSMYHDUJDCKWBT-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxan-3-ylmethyl)-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=1CC1CCCOC1 YSMYHDUJDCKWBT-UHFFFAOYSA-N 0.000 claims description 2
• JJOZJKAFBKLUDL-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxan-4-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=1C1CCOCC1 JJOZJKAFBKLUDL-UHFFFAOYSA-N 0.000 claims description 2
• RBWGPMRNOCCZDH-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxan-4-ylmethyl)-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=1CC1CCOCC1 RBWGPMRNOCCZDH-UHFFFAOYSA-N 0.000 claims description 2
• WBNUZMPOZAJJFD-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxetan-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=1C1CCO1 WBNUZMPOZAJJFD-UHFFFAOYSA-N 0.000 claims description 2
• ODXXVTLZSZNREG-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxolan-2-ylmethyl)-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=1CC1CCCO1 ODXXVTLZSZNREG-UHFFFAOYSA-N 0.000 claims description 2
• SWBOLIZZEUFHRY-UHFFFAOYSA-N n-[2-methyl-5-[5-(oxolan-3-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=1C1CCOC1 SWBOLIZZEUFHRY-UHFFFAOYSA-N 0.000 claims description 2
• KILCHSWKNZRWBE-UHFFFAOYSA-N n-[2-methyl-5-[5-[(1-methylsulfonylpiperidin-4-yl)methyl]-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=1CC1CCN(S(C)(=O)=O)CC1 KILCHSWKNZRWBE-UHFFFAOYSA-N 0.000 claims description 2
• ZXHUCPBRCQZNOE-UHFFFAOYSA-N n-[2-methyl-5-[5-[(2-oxo-1,3-oxazolidin-3-yl)methyl]-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=1CN1CCOC1=O ZXHUCPBRCQZNOE-UHFFFAOYSA-N 0.000 claims description 2
• XZLAVGOISNKMMO-UHFFFAOYSA-N n-[2-methyl-5-[5-[(2-oxopyrrolidin-1-yl)methyl]-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=1CN1CCCC1=O XZLAVGOISNKMMO-UHFFFAOYSA-N 0.000 claims description 2
• IRRMDYCTKFSGNA-GOSISDBHSA-N n-[2-methyl-5-[5-[(2r)-4-methylsulfonylmorpholin-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=1[C@H]1CN(S(C)(=O)=O)CCO1 IRRMDYCTKFSGNA-GOSISDBHSA-N 0.000 claims description 2
• SZXYJRPLLZABPD-QGZVFWFLSA-N n-[2-methyl-5-[5-[(2r)-morpholin-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=1[C@H]1CNCCO1 SZXYJRPLLZABPD-QGZVFWFLSA-N 0.000 claims description 2
• YWHLLRGLXXEQIQ-QGZVFWFLSA-N n-[2-methyl-5-[5-[(2r)-oxolan-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=1[C@H]1CCCO1 YWHLLRGLXXEQIQ-QGZVFWFLSA-N 0.000 claims description 2
• PZWJYLDALLNXEI-OAHLLOKOSA-N n-[2-methyl-5-[5-[(2r)-pyrrolidin-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=1[C@H]1CCCN1 PZWJYLDALLNXEI-OAHLLOKOSA-N 0.000 claims description 2
• BNPWLSHNXHUMGD-INIZCTEOSA-N n-[2-methyl-5-[5-[(2s)-1-methylsulfonylazetidin-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=1[C@@H]1CCN1S(C)(=O)=O BNPWLSHNXHUMGD-INIZCTEOSA-N 0.000 claims description 2
• VECHSHUXUUIYOA-KRWDZBQOSA-N n-[2-methyl-5-[5-[(2s)-1-methylsulfonylpyrrolidin-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=1[C@@H]1CCCN1S(C)(=O)=O VECHSHUXUUIYOA-KRWDZBQOSA-N 0.000 claims description 2
• HNTSGWHWHOTTOK-SFHVURJKSA-N n-[2-methyl-5-[5-[(2s)-1-propan-2-ylsulfonylazetidin-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(C)S(=O)(=O)N1CC[C@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 HNTSGWHWHOTTOK-SFHVURJKSA-N 0.000 claims description 2
• SACHTTWQMHHXAO-AWEZNQCLSA-N n-[2-methyl-5-[5-[(2s)-5-oxopyrrolidin-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=1[C@@H]1CCC(=O)N1 SACHTTWQMHHXAO-AWEZNQCLSA-N 0.000 claims description 2
• SZXYJRPLLZABPD-KRWDZBQOSA-N n-[2-methyl-5-[5-[(2s)-morpholin-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=1[C@@H]1CNCCO1 SZXYJRPLLZABPD-KRWDZBQOSA-N 0.000 claims description 2
• YWHLLRGLXXEQIQ-KRWDZBQOSA-N n-[2-methyl-5-[5-[(2s)-oxolan-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=1[C@@H]1CCCO1 YWHLLRGLXXEQIQ-KRWDZBQOSA-N 0.000 claims description 2
• PZWJYLDALLNXEI-HNNXBMFYSA-N n-[2-methyl-5-[5-[(2s)-pyrrolidin-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=1[C@@H]1CCCN1 PZWJYLDALLNXEI-HNNXBMFYSA-N 0.000 claims description 2
• DZVXDGODJSUYLO-UHFFFAOYSA-N n-[2-methyl-5-[5-[(3,3,4,4-tetrafluoropyrrolidin-1-yl)methyl]-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=1CN1CC(F)(F)C(F)(F)C1 DZVXDGODJSUYLO-UHFFFAOYSA-N 0.000 claims description 2
• BSADYGURRHSOMR-MRXNPFEDSA-N n-[2-methyl-5-[5-[(3r)-morpholin-3-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=1[C@H]1COCCN1 BSADYGURRHSOMR-MRXNPFEDSA-N 0.000 claims description 2
• OFQYNVLASYEPAD-MRXNPFEDSA-N n-[2-methyl-5-[5-[(3r)-piperidin-3-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=1[C@@H]1CCCNC1 OFQYNVLASYEPAD-MRXNPFEDSA-N 0.000 claims description 2
• FWTYRZYDKAVEFO-KRWDZBQOSA-N n-[2-methyl-5-[5-[(3s)-1-methylsulfonylpiperidin-3-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=1[C@H]1CCCN(S(C)(=O)=O)C1 FWTYRZYDKAVEFO-KRWDZBQOSA-N 0.000 claims description 2
• XVOUBHQMUZXTEL-SFHVURJKSA-N n-[2-methyl-5-[5-[(3s)-4-methylsulfonylmorpholin-3-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=1[C@@H]1COCCN1S(C)(=O)=O XVOUBHQMUZXTEL-SFHVURJKSA-N 0.000 claims description 2
• GKWIRIRAAALIKI-UHFFFAOYSA-N n-[2-methyl-5-[5-[(oxane-4-carbonylamino)methyl]-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=1CNC(=O)C1CCOCC1 GKWIRIRAAALIKI-UHFFFAOYSA-N 0.000 claims description 2
• RFFOMLVHKGEXEN-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(1-methylpyrazol-3-yl)sulfonylazetidin-3-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)CN1S(=O)(=O)C=1C=CN(C)N=1 RFFOMLVHKGEXEN-UHFFFAOYSA-N 0.000 claims description 2
• SWJBFJUEVQWUBQ-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(1h-pyrazol-4-ylsulfonyl)azetidin-3-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)CN1S(=O)(=O)C=1C=NNC=1 SWJBFJUEVQWUBQ-UHFFFAOYSA-N 0.000 claims description 2
• WUKPYSKTJMRZEV-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(5-methyl-1,2,4-oxadiazol-3-yl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound O1C(C)=NC(N2CC(C2)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=N1 WUKPYSKTJMRZEV-UHFFFAOYSA-N 0.000 claims description 2
• RUPCJWYSEIJHIA-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(oxolan-3-ylsulfonyl)azetidin-3-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)CN1S(=O)(=O)C1CCOC1 RUPCJWYSEIJHIA-UHFFFAOYSA-N 0.000 claims description 2
• MFRQRHQIEUGXMO-INIZCTEOSA-N n-[2-methyl-5-[5-[[(2s)-pyrrolidin-2-yl]methyl]-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[C@@H]1CCCN1 MFRQRHQIEUGXMO-INIZCTEOSA-N 0.000 claims description 2
• LFIODDCESZFGJY-MRXNPFEDSA-N n-[2-methyl-5-[5-[[(3r)-1-methylsulfonylpyrrolidin-3-yl]methyl]-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[C@H]1CCN(S(C)(=O)=O)C1 LFIODDCESZFGJY-MRXNPFEDSA-N 0.000 claims description 2
• WIBRGMOONPFSOW-GOSISDBHSA-N n-[2-methyl-5-[5-[[[(2r)-oxolane-2-carbonyl]amino]methyl]-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=1CNC(=O)[C@H]1CCCO1 WIBRGMOONPFSOW-GOSISDBHSA-N 0.000 claims description 2
• WIBRGMOONPFSOW-SFHVURJKSA-N n-[2-methyl-5-[5-[[[(2s)-oxolane-2-carbonyl]amino]methyl]-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=1CNC(=O)[C@@H]1CCCO1 WIBRGMOONPFSOW-SFHVURJKSA-N 0.000 claims description 2
• FHKRZVGIZZNWBL-UHFFFAOYSA-N n-[2-methyl-5-[5-[[[2-(oxolan-2-yl)acetyl]amino]methyl]-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=1CNC(=O)CC1CCCO1 FHKRZVGIZZNWBL-UHFFFAOYSA-N 0.000 claims description 2
• DZKBTPRJGXYIEZ-KRWDZBQOSA-N n-[2-methyl-5-[[5-[(2s)-oxolan-2-yl]-1,2,4-oxadiazol-3-yl]amino]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1NC(N=1)=NOC=1[C@@H]1CCCO1 DZKBTPRJGXYIEZ-KRWDZBQOSA-N 0.000 claims description 2
• PIRSXLQAQZSJHR-UHFFFAOYSA-N n-[4-fluoro-2-methyl-5-[5-(1-methylsulfonylazetidin-3-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(F)=C1C(N=1)=NOC=1C1CN(S(C)(=O)=O)C1 PIRSXLQAQZSJHR-UHFFFAOYSA-N 0.000 claims description 2
• HCYBKOZPAFPKKG-UHFFFAOYSA-N n-[5-[3-(3,3-difluoroazetidin-1-yl)-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=1N1CC(F)(F)C1 HCYBKOZPAFPKKG-UHFFFAOYSA-N 0.000 claims description 2
• OKNRJZGEGCYRAE-UHFFFAOYSA-N n-[5-[3-(azetidin-1-yl)-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=1N1CCC1 OKNRJZGEGCYRAE-UHFFFAOYSA-N 0.000 claims description 2
• YNADHXLVXNHSIH-UHFFFAOYSA-N n-[5-[3-[2-(1-benzylpiperidin-4-yl)oxyethyl]-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=1CCOC(CC1)CCN1CC1=CC=CC=C1 YNADHXLVXNHSIH-UHFFFAOYSA-N 0.000 claims description 2
• SCRBYAVXPIPFMD-UHFFFAOYSA-N n-[5-[5-(1-butylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CCCC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 SCRBYAVXPIPFMD-UHFFFAOYSA-N 0.000 claims description 2
• OLPIUTSQDHZMMK-UHFFFAOYSA-N n-[5-[5-(1-butylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CCCC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 OLPIUTSQDHZMMK-UHFFFAOYSA-N 0.000 claims description 2
• HPGVLZCUPLNOIS-UHFFFAOYSA-N n-[5-[5-(3,3-difluoroazetidin-1-yl)-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=1N1CC(F)(F)C1 HPGVLZCUPLNOIS-UHFFFAOYSA-N 0.000 claims description 2
• JFSUWYAXNNVQQW-UHFFFAOYSA-N n-[5-[5-(3,3-difluoroazetidin-1-yl)-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=1N1CC(F)(F)C1 JFSUWYAXNNVQQW-UHFFFAOYSA-N 0.000 claims description 2
• GNBAQNYRZMVIMH-UHFFFAOYSA-N n-[5-[5-(3-hydroxy-3-methylazetidin-1-yl)-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=1N1CC(C)(O)C1 GNBAQNYRZMVIMH-UHFFFAOYSA-N 0.000 claims description 2
• ZIUWPDPWVKTVDM-UHFFFAOYSA-N n-[5-[5-(3-methoxyazetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-7-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OC)CN1C1=NC(C=2C=C(NC(=O)C=3N4C=CC(C)=CC4=NC=3)C(C)=CC=2)=NO1 ZIUWPDPWVKTVDM-UHFFFAOYSA-N 0.000 claims description 2
• BVTXBKGUIFYDBZ-UHFFFAOYSA-N n-[5-[5-(4,4-difluoropiperidin-1-yl)-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=1N1CCC(F)(F)CC1 BVTXBKGUIFYDBZ-UHFFFAOYSA-N 0.000 claims description 2
• IVOJCSDFMRAJQY-UHFFFAOYSA-N n-[5-[5-(4-fluoropiperidin-1-yl)-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=1N1CCC(F)CC1 IVOJCSDFMRAJQY-UHFFFAOYSA-N 0.000 claims description 2
• LUPOWYKEKFHRPH-UHFFFAOYSA-N n-[5-[5-(5,5-difluorooxan-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=1C1CCC(F)(F)CO1 LUPOWYKEKFHRPH-UHFFFAOYSA-N 0.000 claims description 2
• IXIMUZLKBLEPRY-UHFFFAOYSA-N n-[5-[5-(5-hydroxyoxan-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=1C1CCC(O)CO1 IXIMUZLKBLEPRY-UHFFFAOYSA-N 0.000 claims description 2
• MRWXWPAZLMGVLJ-AWEZNQCLSA-N n-[5-[5-[(1s)-1-(3,3-difluoroazetidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1([C@@H](C)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)CC(F)(F)C1 MRWXWPAZLMGVLJ-AWEZNQCLSA-N 0.000 claims description 2
• YXJRRQISXJLTQC-HNNXBMFYSA-N n-[5-[5-[(1s)-1-(3,3-difluoropyrrolidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1([C@@H](C)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)CCC(F)(F)C1 YXJRRQISXJLTQC-HNNXBMFYSA-N 0.000 claims description 2
• UVDZZRSEZOPVBA-GOSISDBHSA-N n-[5-[5-[(2r)-1-acetylpyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(=O)N1CCC[C@@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 UVDZZRSEZOPVBA-GOSISDBHSA-N 0.000 claims description 2
• YLXYXMYLTVGCTP-LJQANCHMSA-N n-[5-[5-[(2r)-4-acetylmorpholin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(C(=O)C)CCO[C@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 YLXYXMYLTVGCTP-LJQANCHMSA-N 0.000 claims description 2
• LUPOWYKEKFHRPH-QGZVFWFLSA-N n-[5-[5-[(2r)-5,5-difluorooxan-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=1[C@H]1CCC(F)(F)CO1 LUPOWYKEKFHRPH-QGZVFWFLSA-N 0.000 claims description 2
• AECSKORUNRFPCG-KRWDZBQOSA-N n-[5-[5-[(2s)-1-acetylazetidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(=O)N1CC[C@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 AECSKORUNRFPCG-KRWDZBQOSA-N 0.000 claims description 2
• CCAVAGMJWZFCHK-INIZCTEOSA-N n-[5-[5-[(2s)-4,4-difluoro-1-methylsulfonylpyrrolidin-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=1[C@@H]1CC(F)(F)CN1S(C)(=O)=O CCAVAGMJWZFCHK-INIZCTEOSA-N 0.000 claims description 2
• ZKYBYYQESORSKZ-HNNXBMFYSA-N n-[5-[5-[(2s)-4,4-difluoropyrrolidin-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=1[C@@H]1CC(F)(F)CN1 ZKYBYYQESORSKZ-HNNXBMFYSA-N 0.000 claims description 2
• LUPOWYKEKFHRPH-KRWDZBQOSA-N n-[5-[5-[(2s)-5,5-difluorooxan-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=1[C@@H]1CCC(F)(F)CO1 LUPOWYKEKFHRPH-KRWDZBQOSA-N 0.000 claims description 2
• KQCIWSKKQUINLJ-AWEZNQCLSA-N n-[5-[5-[(2s)-azetidin-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=1[C@@H]1CCN1 KQCIWSKKQUINLJ-AWEZNQCLSA-N 0.000 claims description 2
• KCKJXDFJABSMKM-UHFFFAOYSA-N n-[5-[5-[(3,3-difluoroazetidin-1-yl)methyl]-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=1CN1CC(F)(F)C1 KCKJXDFJABSMKM-UHFFFAOYSA-N 0.000 claims description 2
• GSKMLWXVRGSGAI-UHFFFAOYSA-N n-[5-[5-[(3,3-difluoroazetidin-1-yl)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=1CN1CC(F)(F)C1 GSKMLWXVRGSGAI-UHFFFAOYSA-N 0.000 claims description 2
• PKNNTLTZPITKMH-UHFFFAOYSA-N n-[5-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-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=1CN1CCC(F)(F)C1 PKNNTLTZPITKMH-UHFFFAOYSA-N 0.000 claims description 2
• DOIQUBRITPIOSG-UHFFFAOYSA-N n-[5-[5-[(3,3-difluoropyrrolidin-1-yl)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=1CN1CCC(F)(F)C1 DOIQUBRITPIOSG-UHFFFAOYSA-N 0.000 claims description 2
• IJJSWTYVGQUACT-UHFFFAOYSA-N n-[5-[5-[(3-cyanoazetidin-1-yl)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=1CN1CC(C#N)C1 IJJSWTYVGQUACT-UHFFFAOYSA-N 0.000 claims description 2
• JSSXCNHPUGPDSU-UHFFFAOYSA-N n-[5-[5-[(3-methoxyazetidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(OC)CN1CC1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 JSSXCNHPUGPDSU-UHFFFAOYSA-N 0.000 claims description 2
• HETJPCJUMZOSEH-LJQANCHMSA-N n-[5-[5-[(3r)-4-acetylmorpholin-3-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(=O)N1CCOC[C@@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 HETJPCJUMZOSEH-LJQANCHMSA-N 0.000 claims description 2
• QCPVMUPDFQSCIJ-UHFFFAOYSA-N n-[5-[5-[(4,4-difluoropiperidin-1-yl)methyl]-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=1CN1CCC(F)(F)CC1 QCPVMUPDFQSCIJ-UHFFFAOYSA-N 0.000 claims description 2
• IXIMUZLKBLEPRY-BUSXIPJBSA-N n-[5-[5-[(5s)-5-hydroxyoxan-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=1C1CC[C@H](O)CO1 IXIMUZLKBLEPRY-BUSXIPJBSA-N 0.000 claims description 2
• ZVGUFKGSWKNETL-UHFFFAOYSA-N n-[5-[5-[1-(3,3-difluoropyrrolidin-1-yl)-2-methoxyethyl]-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=1C(COC)N1CCC(F)(F)C1 ZVGUFKGSWKNETL-UHFFFAOYSA-N 0.000 claims description 2
• NOZLYVJQVPIIOE-UHFFFAOYSA-N n-[5-[5-[1-(3-methoxypropyl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(CCCOC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 NOZLYVJQVPIIOE-UHFFFAOYSA-N 0.000 claims description 2
• FAZYNADUZBPIIM-UHFFFAOYSA-N n-[5-[5-[2-(3,3-difluoroazetidin-1-yl)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=1CCN1CC(F)(F)C1 FAZYNADUZBPIIM-UHFFFAOYSA-N 0.000 claims description 2
• NYWNLYOOXPDSSY-UHFFFAOYSA-N n-[5-[5-[3-(3,3-difluoropyrrolidin-1-yl)-3-oxopropyl]-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=1CCC(=O)N1CCC(F)(F)C1 NYWNLYOOXPDSSY-UHFFFAOYSA-N 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 2
• 210000001147 pulmonary artery Anatomy 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• RFTBIFSCGVOVPP-UHFFFAOYSA-N tert-butyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]-3-methylazetidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1(C)CN(C(=O)OC(C)(C)C)C1 RFTBIFSCGVOVPP-UHFFFAOYSA-N 0.000 claims description 2
• STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 4
• KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims 2
• 125000002883 imidazolyl group Chemical group 0.000 claims 2
• RLBJYLHAGGXZSH-UHFFFAOYSA-N n-[5-[5-(1-ethylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-fluorophenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 RLBJYLHAGGXZSH-UHFFFAOYSA-N 0.000 claims 2
• NTTRDHNNVNRODN-ZBFHGGJFSA-N 6-fluoro-N-[5-[5-[(2S,4R)-4-hydroxypyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=CC=2N(C=1)C(=CN=2)C(=O)NC1=C(C=CC(=C1)C1=NOC(=N1)[C@H]1NC[C@@H](C1)O)C NTTRDHNNVNRODN-ZBFHGGJFSA-N 0.000 claims 1
• NTTRDHNNVNRODN-HOCLYGCPSA-N 6-fluoro-N-[5-[5-[(2S,4S)-4-hydroxypyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=CC=2N(C=1)C(=CN=2)C(=O)NC1=C(C=CC(=C1)C1=NOC(=N1)[C@H]1NC[C@H](C1)O)C NTTRDHNNVNRODN-HOCLYGCPSA-N 0.000 claims 1
• NTTRDHNNVNRODN-GDBMZVCRSA-N 6-fluoro-n-[5-[5-[(2r,4r)-4-hydroxypyrrolidin-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=C(F)C=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@H]1C[C@@H](O)CN1 NTTRDHNNVNRODN-GDBMZVCRSA-N 0.000 claims 1
• GJTDXXNSCUGKJH-UHFFFAOYSA-N 7-methyl-n-[2-methyl-5-[5-(3-methylsulfonylazetidin-1-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[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=1N1CC(S(C)(=O)=O)C1 GJTDXXNSCUGKJH-UHFFFAOYSA-N 0.000 claims 1
• VJYHOVCZZCKOGN-UHFFFAOYSA-N 7-methyl-n-[2-methyl-5-[5-[3-(trifluoromethyl)piperidin-1-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[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=1N1CCCC(C(F)(F)F)C1 VJYHOVCZZCKOGN-UHFFFAOYSA-N 0.000 claims 1
• 206010012434 Dermatitis allergic Diseases 0.000 claims 1
• DIAVKIUSABSDDL-KRWDZBQOSA-N N-[2-methyl-5-[5-[(2S)-oxolan-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=C(C=C(C=C1)C=1OC(=NN=1)[C@H]1OCCC1)NC(=O)C1=CN=C2N1C=CC=C2 DIAVKIUSABSDDL-KRWDZBQOSA-N 0.000 claims 1
• OFQYNVLASYEPAD-INIZCTEOSA-N N-[2-methyl-5-[5-[(3S)-piperidin-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)NC1=C(C=CC(=C1)C1=NOC(=N1)[C@@H]1CNCCC1)C OFQYNVLASYEPAD-INIZCTEOSA-N 0.000 claims 1
• GRNDYFUYEHCQNP-HNNXBMFYSA-N N-[2-methyl-5-[5-[[(3S)-pyrrolidin-3-yl]methyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)NC=1C=C(C=CC=1C)C1=NOC(=N1)C[C@H]1CNCC1 GRNDYFUYEHCQNP-HNNXBMFYSA-N 0.000 claims 1
• DYWKKDSCDLIYDJ-HNNXBMFYSA-N N-[5-[5-[(2S)-azetidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1[C@@H](CC1)C1=NC(=NO1)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N1C=C(C=C2)C)C DYWKKDSCDLIYDJ-HNNXBMFYSA-N 0.000 claims 1
• HETJPCJUMZOSEH-IBGZPJMESA-N N-[5-[5-[(3S)-4-acetylmorpholin-3-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)NC1=C(C=CC(=C1)C1=NOC(=N1)[C@H]1N(CCOC1)C(C)=O)C HETJPCJUMZOSEH-IBGZPJMESA-N 0.000 claims 1
• LSXLOWRPSFGJNQ-UHFFFAOYSA-N N1(CCC1)C(=O)OC1=CC=CN1 Chemical compound N1(CCC1)C(=O)OC1=CC=CN1 LSXLOWRPSFGJNQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
• OQSZKVOEXGDPGH-UHFFFAOYSA-N n-[2-fluoro-5-[5-(1-propylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CCC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 OQSZKVOEXGDPGH-UHFFFAOYSA-N 0.000 claims 1
• HTWIXHVSDGTAHM-UHFFFAOYSA-N n-[2-fluoro-5-[5-(1-pyridin-3-ylsulfonylazetidin-3-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(F)=CC=C1C(N=1)=NOC=1C(C1)CN1S(=O)(=O)C1=CC=CN=C1 HTWIXHVSDGTAHM-UHFFFAOYSA-N 0.000 claims 1
• WFBGMADGXUUEMI-UHFFFAOYSA-N n-[2-fluoro-5-[5-[1-(1-methylpyrazol-3-yl)sulfonylazetidin-3-yl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CN1C=CC(S(=O)(=O)N2CC(C2)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=N1 WFBGMADGXUUEMI-UHFFFAOYSA-N 0.000 claims 1
• NAVFFQNJMSIIAY-UHFFFAOYSA-N n-[2-methyl-5-(3-morpholin-4-yl-1,2,4-oxadiazol-5-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(ON=1)=NC=1N1CCOCC1 NAVFFQNJMSIIAY-UHFFFAOYSA-N 0.000 claims 1
• SZXYJRPLLZABPD-UHFFFAOYSA-N n-[2-methyl-5-(5-morpholin-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=1C1CNCCO1 SZXYJRPLLZABPD-UHFFFAOYSA-N 0.000 claims 1
• OFQYNVLASYEPAD-UHFFFAOYSA-N n-[2-methyl-5-(5-piperidin-3-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=1C1CCCNC1 OFQYNVLASYEPAD-UHFFFAOYSA-N 0.000 claims 1
• NRRFWITUTKKQLY-UHFFFAOYSA-N n-[2-methyl-5-(5-piperidin-4-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=1C1CCNCC1 NRRFWITUTKKQLY-UHFFFAOYSA-N 0.000 claims 1
• OFXZHEHVBNTWSA-UHFFFAOYSA-N n-[2-methyl-5-[3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)-1,2,4-oxadiazol-5-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(ON=1)=NC=1N(C1)CC21COC2 OFXZHEHVBNTWSA-UHFFFAOYSA-N 0.000 claims 1
• PMGDZIOQZILYIH-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-methylpiperidin-2-yl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CN1CCCCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 PMGDZIOQZILYIH-UHFFFAOYSA-N 0.000 claims 1
• RUBYTXLURVXRFY-UHFFFAOYSA-N n-[2-methyl-5-[5-(1-pyrazin-2-ylazetidin-3-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)CN1C1=CN=CC=N1 RUBYTXLURVXRFY-UHFFFAOYSA-N 0.000 claims 1
• XWULAJDNKIYOLR-UHFFFAOYSA-N n-[2-methyl-5-[5-(piperidin-4-ylmethyl)-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=1CC1CCNCC1 XWULAJDNKIYOLR-UHFFFAOYSA-N 0.000 claims 1
• BIUPZJHNSARCDG-UHFFFAOYSA-N n-[2-methyl-5-[5-[(1-methylsulfonylazetidin-3-yl)methyl]-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=1CC1CN(S(C)(=O)=O)C1 BIUPZJHNSARCDG-UHFFFAOYSA-N 0.000 claims 1
• VECHSHUXUUIYOA-QGZVFWFLSA-N n-[2-methyl-5-[5-[(2r)-1-methylsulfonylpyrrolidin-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=1[C@H]1CCCN1S(C)(=O)=O VECHSHUXUUIYOA-QGZVFWFLSA-N 0.000 claims 1
• IMROZJSTMVFRFD-HNNXBMFYSA-N n-[2-methyl-5-[5-[(2s)-6-oxopiperidin-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=1[C@@H]1CCCC(=O)N1 IMROZJSTMVFRFD-HNNXBMFYSA-N 0.000 claims 1
• QKJWTIWNTYNGLY-UHFFFAOYSA-N n-[2-methyl-5-[5-[(3-methylsulfonylazetidin-1-yl)methyl]-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=1CN1CC(S(C)(=O)=O)C1 QKJWTIWNTYNGLY-UHFFFAOYSA-N 0.000 claims 1
• FWTYRZYDKAVEFO-QGZVFWFLSA-N n-[2-methyl-5-[5-[(3r)-1-methylsulfonylpiperidin-3-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=1[C@@H]1CCCN(S(C)(=O)=O)C1 FWTYRZYDKAVEFO-QGZVFWFLSA-N 0.000 claims 1
• XVOUBHQMUZXTEL-GOSISDBHSA-N n-[2-methyl-5-[5-[(3r)-4-methylsulfonylmorpholin-3-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=1[C@H]1COCCN1S(C)(=O)=O XVOUBHQMUZXTEL-GOSISDBHSA-N 0.000 claims 1
• BSADYGURRHSOMR-INIZCTEOSA-N n-[2-methyl-5-[5-[(3s)-morpholin-3-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=1[C@@H]1COCCN1 BSADYGURRHSOMR-INIZCTEOSA-N 0.000 claims 1
• NSUHWACMKLYMPX-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-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)CN1S(=O)(=O)C1=CN(C)C=N1 NSUHWACMKLYMPX-UHFFFAOYSA-N 0.000 claims 1
• WGBHNGBPMUETIL-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-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)CN1S(=O)(=O)C=1C=NN(C)C=1 WGBHNGBPMUETIL-UHFFFAOYSA-N 0.000 claims 1
• KPPJLSSCUODPBJ-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(2,2,2-trifluoroacetyl)azetidin-3-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=1C1CN(C(=O)C(F)(F)F)C1 KPPJLSSCUODPBJ-UHFFFAOYSA-N 0.000 claims 1
• RBMMWQBMHPODKQ-UHFFFAOYSA-N n-[2-methyl-5-[5-[1-(oxan-4-ylsulfonyl)azetidin-3-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)CN1S(=O)(=O)C1CCOCC1 RBMMWQBMHPODKQ-UHFFFAOYSA-N 0.000 claims 1
• AUUUTUYFGNSIAJ-UHFFFAOYSA-N n-[2-methyl-5-[5-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)CCC1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 AUUUTUYFGNSIAJ-UHFFFAOYSA-N 0.000 claims 1
• DQRWPHUOALLCBU-UHFFFAOYSA-N n-[2-methyl-5-[5-[[(2-morpholin-4-ylacetyl)amino]methyl]-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=1CNC(=O)CN1CCOCC1 DQRWPHUOALLCBU-UHFFFAOYSA-N 0.000 claims 1
• XQEBZZONPGKMBE-KRWDZBQOSA-N n-[2-methyl-5-[5-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methyl]-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[C@@H]1CCCN1S(C)(=O)=O XQEBZZONPGKMBE-KRWDZBQOSA-N 0.000 claims 1
• OQHCYUYWKWXXNI-UHFFFAOYSA-N n-[2-methyl-5-[5-[[(3-methyloxetane-3-carbonyl)amino]methyl]-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=1CNC(=O)C1(C)COC1 OQHCYUYWKWXXNI-UHFFFAOYSA-N 0.000 claims 1
• GRNDYFUYEHCQNP-OAHLLOKOSA-N n-[2-methyl-5-[5-[[(3r)-pyrrolidin-3-yl]methyl]-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[C@H]1CCNC1 GRNDYFUYEHCQNP-OAHLLOKOSA-N 0.000 claims 1
• LFIODDCESZFGJY-INIZCTEOSA-N n-[2-methyl-5-[5-[[(3s)-1-methylsulfonylpyrrolidin-3-yl]methyl]-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[C@@H]1CCN(S(C)(=O)=O)C1 LFIODDCESZFGJY-INIZCTEOSA-N 0.000 claims 1
• JOSSAMPVZQIJHC-UHFFFAOYSA-N n-[2-methyl-5-[5-[[[2-(oxan-4-yl)acetyl]amino]methyl]-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=1CNC(=O)CC1CCOCC1 JOSSAMPVZQIJHC-UHFFFAOYSA-N 0.000 claims 1
• DZKBTPRJGXYIEZ-QGZVFWFLSA-N n-[2-methyl-5-[[5-[(2r)-oxolan-2-yl]-1,2,4-oxadiazol-3-yl]amino]phenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1NC(N=1)=NOC=1[C@H]1CCCO1 DZKBTPRJGXYIEZ-QGZVFWFLSA-N 0.000 claims 1
• VUFNSASDEFATIM-UHFFFAOYSA-N n-[5-[3-(3-hydroxy-3-methylazetidin-1-yl)-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=1N1CC(C)(O)C1 VUFNSASDEFATIM-UHFFFAOYSA-N 0.000 claims 1
• HMHRKXIDLGOOOL-UHFFFAOYSA-N n-[5-[3-(4,4-difluoropiperidin-1-yl)-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=1N1CCC(F)(F)CC1 HMHRKXIDLGOOOL-UHFFFAOYSA-N 0.000 claims 1
• LFZHQLJKEQTGGB-UHFFFAOYSA-N n-[5-[5-(1-acetylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(C(=O)C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 LFZHQLJKEQTGGB-UHFFFAOYSA-N 0.000 claims 1
• GBQPRTVFRBHZMG-UHFFFAOYSA-N n-[5-[5-(1-acetylpiperidin-4-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 GBQPRTVFRBHZMG-UHFFFAOYSA-N 0.000 claims 1
• BDSGXEMYMDTGPY-UHFFFAOYSA-N n-[5-[5-(1-ethylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(CC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 BDSGXEMYMDTGPY-UHFFFAOYSA-N 0.000 claims 1
• MJYRDCNKNMEZSB-UHFFFAOYSA-N n-[5-[5-(1-ethylsulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1N(S(=O)(=O)CC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 MJYRDCNKNMEZSB-UHFFFAOYSA-N 0.000 claims 1
• DHCVRZJISMQDTH-UHFFFAOYSA-N n-[5-[5-(3,3-difluoroazetidin-1-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=1N1CC(F)(F)C1 DHCVRZJISMQDTH-UHFFFAOYSA-N 0.000 claims 1
• NXHNYXPDLZAQKT-UHFFFAOYSA-N n-[5-[5-(3,3-difluoropyrrolidin-1-yl)-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=1N1CCC(F)(F)C1 NXHNYXPDLZAQKT-UHFFFAOYSA-N 0.000 claims 1
• RGZVFNJQTQXPPZ-UHFFFAOYSA-N n-[5-[5-(azetidin-3-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=1C1CNC1 RGZVFNJQTQXPPZ-UHFFFAOYSA-N 0.000 claims 1
• UYGMFUQHWXEGNA-UHFFFAOYSA-N n-[5-[5-(azetidin-3-ylmethyl)-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=1CC1CNC1 UYGMFUQHWXEGNA-UHFFFAOYSA-N 0.000 claims 1
• QESCCMLRTLGBMQ-UHFFFAOYSA-N n-[5-[5-(azetidin-3-yloxymethyl)-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=1COC1CNC1 QESCCMLRTLGBMQ-UHFFFAOYSA-N 0.000 claims 1
• MRWXWPAZLMGVLJ-CQSZACIVSA-N n-[5-[5-[(1r)-1-(3,3-difluoroazetidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1([C@H](C)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)CC(F)(F)C1 MRWXWPAZLMGVLJ-CQSZACIVSA-N 0.000 claims 1
• YXJRRQISXJLTQC-OAHLLOKOSA-N n-[5-[5-[(1r)-1-(3,3-difluoropyrrolidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N1([C@H](C)C=2ON=C(N=2)C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)CCC(F)(F)C1 YXJRRQISXJLTQC-OAHLLOKOSA-N 0.000 claims 1
• IOJHWFKWDYIHNX-KRWDZBQOSA-N n-[5-[5-[(2s)-1-acetyl-4,4-difluoropyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(=O)N1CC(F)(F)C[C@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 IOJHWFKWDYIHNX-KRWDZBQOSA-N 0.000 claims 1
• UVDZZRSEZOPVBA-SFHVURJKSA-N n-[5-[5-[(2s)-1-acetylpyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(=O)N1CCC[C@H]1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 UVDZZRSEZOPVBA-SFHVURJKSA-N 0.000 claims 1
• XKKRKCASQZDTNW-UHFFFAOYSA-N n-[5-[5-[(3-cyanoazetidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-(2,4-dimethyl-1,3-thiazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound S1C(C)=NC(C)=C1C1=CN2C(C(=O)NC=3C(=CC=C(C=3)C=3N=C(CN4CC(C4)C#N)ON=3)C)=CN=C2C=C1 XKKRKCASQZDTNW-UHFFFAOYSA-N 0.000 claims 1
• SQDFNKGJNPVNCZ-UHFFFAOYSA-N n-[5-[5-[(3-fluoroazetidin-1-yl)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=1CN1CC(F)C1 SQDFNKGJNPVNCZ-UHFFFAOYSA-N 0.000 claims 1
• SXWNRRQBCBMTMR-UHFFFAOYSA-N n-[5-[5-[(3-hydroxyazetidin-1-yl)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=1CN1CC(O)C1 SXWNRRQBCBMTMR-UHFFFAOYSA-N 0.000 claims 1
• RSUNUJZKQIRGJP-UHFFFAOYSA-N n-[5-[5-[(4,4-difluoropiperidin-1-yl)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=1CN1CCC(F)(F)CC1 RSUNUJZKQIRGJP-UHFFFAOYSA-N 0.000 claims 1
• JHIHHMHLBVXIFM-UHFFFAOYSA-N n-[5-[5-[1-(1h-imidazol-5-ylsulfonyl)azetidin-3-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)CN1S(=O)(=O)C1=CN=CN1 JHIHHMHLBVXIFM-UHFFFAOYSA-N 0.000 claims 1
• OHUXHNBILPJFQM-UHFFFAOYSA-N n-[5-[5-[3-[(2-methoxyacetyl)amino]oxetan-3-yl]-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)COC1 OHUXHNBILPJFQM-UHFFFAOYSA-N 0.000 claims 1
• WDXROJJHCLNJKC-UHFFFAOYSA-N n-[5-[5-[[3-(hydroxymethyl)azetidin-1-yl]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=1CN1CC(CO)C1 WDXROJJHCLNJKC-UHFFFAOYSA-N 0.000 claims 1
• AURREUFUGZUHCE-UHFFFAOYSA-N n-[5-[5-[[3-(methoxymethyl)azetidin-1-yl]methyl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(COC)CN1CC1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 AURREUFUGZUHCE-UHFFFAOYSA-N 0.000 claims 1
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• 239000012453 solvate Substances 0.000 description 58
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• 230000005764 inhibitory process Effects 0.000 description 31
• QHGPYOBKIQWLLL-UHFFFAOYSA-N 3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1NC(=O)C1=CN=C2N1C=CC=C2 QHGPYOBKIQWLLL-UHFFFAOYSA-N 0.000 description 29
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• 229940124597 therapeutic agent Drugs 0.000 description 26
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