CA2845169C - Compounds and compositions as c-kit kinase inhibitors - Google Patents

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Publication number

CA2845169C

CA2845169C CA2845169A CA2845169A CA2845169C CA 2845169 C CA2845169 C CA 2845169C CA 2845169 A CA2845169 A CA 2845169A CA 2845169 A CA2845169 A CA 2845169A CA 2845169 C CA2845169 C CA 2845169C

Authority

CA

Canada

Prior art keywords

oxadiazol

pyridine

methyl

carboxamide

imidazo

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 abstract description 360
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 title claims abstract description 141
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 title claims abstract description 140
• 239000000203 mixture Substances 0.000 title description 94
• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 208
• 201000010099 disease Diseases 0.000 claims abstract description 133
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 72
• 208000035475 disorder Diseases 0.000 claims abstract description 67
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 39
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 39
• 101150038994 PDGFRA gene Proteins 0.000 claims abstract description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 320
• 125000005842 heteroatom Chemical group 0.000 claims description 220
• -1 pyrazol-4-yl Chemical group 0.000 claims description 206
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 192
• 235000005152 nicotinamide Nutrition 0.000 claims description 160
• 239000011570 nicotinamide Substances 0.000 claims description 160
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 125
• 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 122
• 150000003839 salts Chemical class 0.000 claims description 116
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 94
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 62
• 208000006673 asthma Diseases 0.000 claims description 61
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 61
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 59
• 125000005843 halogen group Chemical group 0.000 claims description 49
• 239000003814 drug Substances 0.000 claims description 47
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 45
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 43
• 229910052805 deuterium Inorganic materials 0.000 claims description 43
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 42
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 41
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 39
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 22
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 22
• 201000010105 allergic rhinitis Diseases 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 16
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 16
• 208000017520 skin disease Diseases 0.000 claims description 16
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 15
• 206010039710 Scleroderma Diseases 0.000 claims description 15
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 15
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 14
• 208000011580 syndromic disease Diseases 0.000 claims description 14
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 13
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 12
• 201000008937 atopic dermatitis Diseases 0.000 claims description 12
• 230000009787 cardiac fibrosis Effects 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• 208000008585 mastocytosis Diseases 0.000 claims description 12
• 230000001404 mediated effect Effects 0.000 claims description 12
• 201000006417 multiple sclerosis Diseases 0.000 claims description 12
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
• 206010012442 Dermatitis contact Diseases 0.000 claims description 11
• 201000001441 melanoma Diseases 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 201000006512 mast cell neoplasm Diseases 0.000 claims description 10
• 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 description 10
• 208000002029 allergic contact dermatitis Diseases 0.000 claims description 9
• 230000002052 anaphylactic effect Effects 0.000 claims description 9
• 206010048768 Dermatosis Diseases 0.000 claims description 8
• 206010019668 Hepatic fibrosis Diseases 0.000 claims description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 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 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• RWRIWBAIICGTTQ-UHFFFAOYSA-N anhydrous difluoromethane Natural products FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 6
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
• 125000000335 thiazolyl 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
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 4
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 4
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 4
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 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
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 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
• 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 2
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 2
• XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
• LZYCIZOJKFRILT-UHFFFAOYSA-N 2,2-difluoroethyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CN(C(=O)OCC(F)F)C1 LZYCIZOJKFRILT-UHFFFAOYSA-N 0.000 claims 1
• KIWDODIDVNNOFG-UHFFFAOYSA-N 2-hydroxyethyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C1CN(C(=O)OCCO)C1 KIWDODIDVNNOFG-UHFFFAOYSA-N 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• HACVQXVPOCUYAL-IBGZPJMESA-N N12C=C(C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1[C@@H]1CCN1C(=O)OC(C)(C)C Chemical compound N12C=C(C)C=CC2=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(N=1)=NOC=1[C@@H]1CCN1C(=O)OC(C)(C)C HACVQXVPOCUYAL-IBGZPJMESA-N 0.000 claims 1
• IAMRQJMHPHMFSP-UHFFFAOYSA-N [3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]methyl 3-methoxyazetidine-1-carboxylate Chemical compound C1C(OC)CN1C(=O)OCC1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 IAMRQJMHPHMFSP-UHFFFAOYSA-N 0.000 claims 1
• IFQXMPRQZBDRIQ-UHFFFAOYSA-N [3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]methyl n-(1-methylazetidin-3-yl)carbamate Chemical compound C1N(C)CC1NC(=O)OCC1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 IFQXMPRQZBDRIQ-UHFFFAOYSA-N 0.000 claims 1
• VJYCJBUHKBKMIM-UHFFFAOYSA-N methyl 2-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]morpholine-4-carboxylate Chemical compound C1N(C(=O)OC)CCOC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 VJYCJBUHKBKMIM-UHFFFAOYSA-N 0.000 claims 1
• RUJNYZBXKFNCLL-UHFFFAOYSA-N methyl 2-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 RUJNYZBXKFNCLL-UHFFFAOYSA-N 0.000 claims 1
• JTYZDFSHTUFSRA-UHFFFAOYSA-N methyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]-3-methylazetidine-1-carboxylate Chemical compound C1N(C(=O)OC)CC1(C)C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 JTYZDFSHTUFSRA-UHFFFAOYSA-N 0.000 claims 1
• CKWPFDNDCISONF-UHFFFAOYSA-N methyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 CKWPFDNDCISONF-UHFFFAOYSA-N 0.000 claims 1
• BJKZEMLXJNQRRQ-UHFFFAOYSA-N methyl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC)CCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 BJKZEMLXJNQRRQ-UHFFFAOYSA-N 0.000 claims 1
• MKQARELPFVOFQR-UHFFFAOYSA-N methyl 4-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 MKQARELPFVOFQR-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 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
• 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 1
• 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 1
• JBQREQMWTORZSW-UHFFFAOYSA-N n-[5-[5-[(3-cyanoazetidin-1-yl)methyl]-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(CN3CC(C3)C#N)ON=2)C=C1NC(=O)C(N1C=2)=CN=C1C=CC=2C=1C=NN(C)C=1 JBQREQMWTORZSW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• XPOSJLHDINBPBE-UHFFFAOYSA-N propan-2-yl 3-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(C)=CC=2)=NO1 XPOSJLHDINBPBE-UHFFFAOYSA-N 0.000 claims 1
• ODFVWTSHNOMHSJ-SFHVURJKSA-N tert-butyl (2s)-2-[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1[C@@H]1CCN1C(=O)OC(C)(C)C ODFVWTSHNOMHSJ-SFHVURJKSA-N 0.000 claims 1
• FUQTYEZADBXDQC-GOSISDBHSA-N tert-butyl (3r)-3-[[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]methyl]pyrrolidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C[C@H]1CCN(C(=O)OC(C)(C)C)C1 FUQTYEZADBXDQC-GOSISDBHSA-N 0.000 claims 1
• FUQTYEZADBXDQC-SFHVURJKSA-N tert-butyl (3s)-3-[[3-[3-(imidazo[1,2-a]pyridine-3-carbonylamino)-4-methylphenyl]-1,2,4-oxadiazol-5-yl]methyl]pyrrolidine-1-carboxylate Chemical compound C1=C(NC(=O)C=2N3C=CC=CC3=NC=2)C(C)=CC=C1C(N=1)=NOC=1C[C@@H]1CCN(C(=O)OC(C)(C)C)C1 FUQTYEZADBXDQC-SFHVURJKSA-N 0.000 claims 1
• RKHFBEOIKDJWQN-UHFFFAOYSA-N tert-butyl 3-[3-[4-fluoro-3-(imidazo[1,2-a]pyridine-3-carbonylamino)phenyl]-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1C1=NC(C=2C=C(NC(=O)C=3N4C=CC=CC4=NC=3)C(F)=CC=2)=NO1 RKHFBEOIKDJWQN-UHFFFAOYSA-N 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 82
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 abstract description 63
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 abstract description 63
• 238000000034 method Methods 0.000 abstract description 51
• 230000004913 activation Effects 0.000 abstract description 16
• 230000002159 abnormal effect Effects 0.000 abstract description 6
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 abstract description 2
• 239000003909 protein kinase inhibitor Substances 0.000 abstract description 2
• 230000002074 deregulated effect Effects 0.000 abstract 1
• 125000003003 spiro group Chemical group 0.000 description 63
• 210000003630 histaminocyte Anatomy 0.000 description 61
• 239000012453 solvate Substances 0.000 description 61
• 238000011282 treatment Methods 0.000 description 60
• 150000001204 N-oxides Chemical class 0.000 description 52
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 48
• 150000004677 hydrates Chemical class 0.000 description 45
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 41
• 230000005764 inhibitory process Effects 0.000 description 34
• 210000004027 cell Anatomy 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• 229940124597 therapeutic agent Drugs 0.000 description 26
• 238000009472 formulation Methods 0.000 description 20
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 19
• 210000004072 lung Anatomy 0.000 description 19
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 18
• 208000023275 Autoimmune disease Diseases 0.000 description 18
• 208000027866 inflammatory disease Diseases 0.000 description 17
• 239000000843 powder Substances 0.000 description 17
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