TW201313717A - 作為ｃ－Ｋｉｔ激酶抑制劑之化合物及組合物 - Google Patents

Info

Publication number

TW201313717A

TW201313717A TW101131942A TW101131942A TW201313717A TW 201313717 A TW201313717 A TW 201313717A TW 101131942 A TW101131942 A TW 101131942A TW 101131942 A TW101131942 A TW 101131942A TW 201313717 A TW201313717 A TW 201313717A

Authority

TW

Taiwan

Prior art keywords

oxadiazol

imidazo

substituted

formula

methyl

Prior art date

2011-09-01

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 345
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 title claims abstract description 132
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 title claims abstract description 131
• 239000000203 mixture Substances 0.000 title description 99
• 229940043355 kinase inhibitor Drugs 0.000 title description 7
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 153
• 201000010099 disease Diseases 0.000 claims abstract description 144
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 70
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 43
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 43
• 102000001393 Platelet-Derived Growth Factor alpha Receptor Human genes 0.000 claims abstract description 7
• 108010068588 Platelet-Derived Growth Factor alpha Receptor Proteins 0.000 claims abstract description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 250
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 203
• 229910052760 oxygen Inorganic materials 0.000 claims description 150
• 229910052717 sulfur Inorganic materials 0.000 claims description 145
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 133
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
• 150000003839 salts Chemical class 0.000 claims description 104
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 98
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 79
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 65
• 210000003630 histaminocyte Anatomy 0.000 claims description 64
• 208000006673 asthma Diseases 0.000 claims description 59
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 57
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 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 46
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 45
• 239000003814 drug Substances 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 35
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 35
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 33
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000003003 spiro group Chemical group 0.000 claims description 23
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 22
• 208000017520 skin disease Diseases 0.000 claims description 21
• 208000023275 Autoimmune disease Diseases 0.000 claims description 20
• 208000023504 respiratory system disease Diseases 0.000 claims description 20
• 125000000753 cycloalkyl 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
• 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 claims description 18
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 201000008312 primary pulmonary hypertension Diseases 0.000 claims description 18
• 208000024780 Urticaria Diseases 0.000 claims description 17
• 201000010105 allergic rhinitis Diseases 0.000 claims description 17
• 208000002815 pulmonary hypertension 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 16
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 15
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 15
• 206010039710 Scleroderma Diseases 0.000 claims description 15
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 15
• 208000030159 metabolic disease Diseases 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
• 230000003176 fibrotic effect Effects 0.000 claims description 13
• 208000027866 inflammatory disease Diseases 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 12
• 230000001404 mediated effect Effects 0.000 claims description 12
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 12
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 12
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
• 230000009787 cardiac fibrosis Effects 0.000 claims description 11
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 11
• 229910052805 deuterium Inorganic materials 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 235000005152 nicotinamide Nutrition 0.000 claims description 8
• 239000011570 nicotinamide Substances 0.000 claims description 8
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 7
• 208000016097 disease of metabolism Diseases 0.000 claims description 7
• 230000004968 inflammatory condition Effects 0.000 claims description 7
• 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
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 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 5
• RWRIWBAIICGTTQ-UHFFFAOYSA-N anhydrous difluoromethane Natural products FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 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
• 150000002576 ketones Chemical class 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 5
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
• HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 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
• 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 4
• 125000002924 primary amino group Chemical group [H]N([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
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000004495 thiazol-4-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
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
• 150000001555 benzenes Chemical class 0.000 claims description 3
• 230000033228 biological regulation Effects 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 230000007794 irritation Effects 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 3
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 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
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 2
• GEHZTZHYYZQLDX-UHFFFAOYSA-N 7-methyl-n-[2-methyl-5-(5-morpholin-4-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=1N1CCOCC1 GEHZTZHYYZQLDX-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 2
• 150000002460 imidazoles Chemical class 0.000 claims description 2
• CBTGNLZUIZHUHY-UHFFFAOYSA-N methyl cyclobutanecarboxylate Chemical compound COC(=O)C1CCC1 CBTGNLZUIZHUHY-UHFFFAOYSA-N 0.000 claims description 2
• 150000004702 methyl esters Chemical class 0.000 claims description 2
• 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 description 2
• 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 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
• 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
• 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
• 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
• 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 description 2
• 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 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
• QQSFMUMRSLYSNY-UHFFFAOYSA-N n-[5-[3-(4-fluoropiperidin-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)CC1 QQSFMUMRSLYSNY-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
• 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 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
• 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 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
• 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
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