CA2871270A1 - Substituted pyridine compounds as crac modulators - Google Patents

Info

Publication number

CA2871270A1

CA2871270A1 CA2871270A CA2871270A CA2871270A1 CA 2871270 A1 CA2871270 A1 CA 2871270A1 CA 2871270 A CA2871270 A CA 2871270A CA 2871270 A CA2871270 A CA 2871270A CA 2871270 A1 CA2871270 A1 CA 2871270A1

Authority

CA

Canada

Prior art keywords

methyl

substituted

oxadiazol

oxo

dihydro

Prior art date

2012-05-02

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000003222 pyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 205
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 104
• 201000010099 disease Diseases 0.000 claims abstract description 56
• 208000035475 disorder Diseases 0.000 claims abstract description 48
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 239000011575 calcium Substances 0.000 claims abstract description 17
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052791 calcium Inorganic materials 0.000 claims abstract description 16
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 150000001669 calcium Chemical class 0.000 claims abstract description 6
• 238000000034 method Methods 0.000 claims description 99
• -1 nitro, hydroxyl Chemical group 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 125000001188 haloalkyl group Chemical group 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 201000006417 multiple sclerosis Diseases 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 20
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 238000005859 coupling reaction Methods 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 14
• 206010061218 Inflammation Diseases 0.000 claims description 14
• 230000004054 inflammatory process Effects 0.000 claims description 14
• 208000023275 Autoimmune disease Diseases 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 13
• 210000000056 organ Anatomy 0.000 claims description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
• 208000010668 atopic eczema Diseases 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 230000000172 allergic effect Effects 0.000 claims description 9
• 239000003153 chemical reaction reagent Substances 0.000 claims description 9
• 238000010168 coupling process Methods 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 8
• 230000008878 coupling Effects 0.000 claims description 8
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 239000003446 ligand Substances 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 claims description 5
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 229910000080 stannane Inorganic materials 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• MEXWYXRQNRGPHL-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F MEXWYXRQNRGPHL-UHFFFAOYSA-N 0.000 claims description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 9
• PPRZCLXXYKZUSI-UHFFFAOYSA-N 2,6-difluoro-n-[3-methyl-4-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C(=C1)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F PPRZCLXXYKZUSI-UHFFFAOYSA-N 0.000 claims 1
• ZZVSSHQTNNGXAU-UHFFFAOYSA-N 2,6-difluoro-n-[3-methyl-4-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound C=1C=C(C=2C=C(C=NC=2)C=2OC(=O)N(C)N=2)C(C)=CC=1NC(=O)C1=C(F)C=CC=C1F ZZVSSHQTNNGXAU-UHFFFAOYSA-N 0.000 claims 1
• BPYNQBOVOFXWFN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BPYNQBOVOFXWFN-UHFFFAOYSA-N 0.000 claims 1
• QANOPYAOAXAPFN-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methoxy-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound COC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F QANOPYAOAXAPFN-UHFFFAOYSA-N 0.000 claims 1
• YRFOJUUSTKSSDD-UHFFFAOYSA-N 2,6-difluoro-n-[4-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F YRFOJUUSTKSSDD-UHFFFAOYSA-N 0.000 claims 1
• IXHVNPQABNHDJZ-UHFFFAOYSA-N 2,6-difluoro-n-[4-[3-methyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]benzamide Chemical compound CC1=C(C=2OC(=O)N(C)N=2)C=CN=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F IXHVNPQABNHDJZ-UHFFFAOYSA-N 0.000 claims 1
• BXQOUXBFUWOMQH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[4-methyl-6-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CC1=CC(C=2OC(=O)N(C)N=2)=NC=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F BXQOUXBFUWOMQH-UHFFFAOYSA-N 0.000 claims 1
• NJZXRQZXVFOFKH-UHFFFAOYSA-N 2,6-difluoro-n-[4-[6-methyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]phenyl]benzamide Chemical compound N=1C(C)=CC(C=2OC(=O)N(C)N=2)=CC=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F NJZXRQZXVFOFKH-UHFFFAOYSA-N 0.000 claims 1
• ZVZIYLLKDARKMS-UHFFFAOYSA-N 2,6-difluoro-n-[5-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1F ZVZIYLLKDARKMS-UHFFFAOYSA-N 0.000 claims 1
• KYKOOENIONYICB-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyrazin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=NC=2)=C1 KYKOOENIONYICB-UHFFFAOYSA-N 0.000 claims 1
• KKXVOLVZGIWQCP-UHFFFAOYSA-N 2,6-difluoro-n-[5-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyridin-2-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2C=NC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 KKXVOLVZGIWQCP-UHFFFAOYSA-N 0.000 claims 1
• VQWJUCBLOQUNKC-UHFFFAOYSA-N 2,6-difluoro-n-[6-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]pyridin-3-yl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2N=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)=C1 VQWJUCBLOQUNKC-UHFFFAOYSA-N 0.000 claims 1
• QCABWHXPLIOOOC-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[4-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1Cl QCABWHXPLIOOOC-UHFFFAOYSA-N 0.000 claims 1
• QITGKAOYCSIFCM-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[4-[5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)-2-(trifluoromethyl)pyridin-3-yl]phenyl]benzamide Chemical compound O1C(=O)N(C)N=C1C1=CN=C(C(F)(F)F)C(C=2C=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=CC=2)=C1 QITGKAOYCSIFCM-UHFFFAOYSA-N 0.000 claims 1
• QSUHEZAOJVTNKR-UHFFFAOYSA-N 2-chloro-n-[4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]-6-fluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1Cl QSUHEZAOJVTNKR-UHFFFAOYSA-N 0.000 claims 1
• MIADLJOXYXVUOJ-UHFFFAOYSA-N 2-chloro-n-[5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]-6-fluorobenzamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2N=CC(NC(=O)C=3C(=CC=CC=3F)Cl)=NC=2)=CN=C1C1CC1 MIADLJOXYXVUOJ-UHFFFAOYSA-N 0.000 claims 1
• DCZPOJMZCYLMIF-UHFFFAOYSA-N 2-chloro-n-[5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrazin-2-yl]-6-fluorobenzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CN=C1NC(=O)C1=C(F)C=CC=C1Cl DCZPOJMZCYLMIF-UHFFFAOYSA-N 0.000 claims 1
• XEWYMSHQKLWAPB-UHFFFAOYSA-N 2-fluoro-6-methyl-n-[4-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]phenyl]benzamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1NC(=O)C1=C(C)C=CC=C1F XEWYMSHQKLWAPB-UHFFFAOYSA-N 0.000 claims 1
• BLZSFZSANKKGPF-UHFFFAOYSA-N 4-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)benzamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 BLZSFZSANKKGPF-UHFFFAOYSA-N 0.000 claims 1
• QAOPDAXPTZSLLB-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)furan-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2OC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 QAOPDAXPTZSLLB-UHFFFAOYSA-N 0.000 claims 1
• VTNZPMJAXJQINO-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(2,6-difluorophenyl)thiophene-2-carboxamide Chemical compound O1C(=O)N(C)N=C1C(C=C1C=2SC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)=CN=C1C1CC1 VTNZPMJAXJQINO-UHFFFAOYSA-N 0.000 claims 1
• XFRUEBWRBSPKPX-UHFFFAOYSA-N 5-[2-cyclopropyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-n-(3-methylpyridin-4-yl)thiophene-2-carboxamide Chemical compound CC1=CN=CC=C1NC(=O)C1=CC=C(C=2C(=NC=C(C=2)C=2OC(=O)N(C)N=2)C2CC2)S1 XFRUEBWRBSPKPX-UHFFFAOYSA-N 0.000 claims 1
• XNKQRDJADVUOGX-UHFFFAOYSA-N 5-[5-[5-[(2,6-difluorophenyl)methylamino]pyridin-2-yl]-6-ethylpyridin-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N=C1)=CC=C1NCC1=C(F)C=CC=C1F XNKQRDJADVUOGX-UHFFFAOYSA-N 0.000 claims 1
• JGEVQLZYMJHDLP-UHFFFAOYSA-N 5-[5-[6-[(2,6-difluorophenyl)methylamino]pyridin-3-yl]-6-ethylpyridin-3-yl]-3-methyl-1,3,4-oxadiazol-2-one Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=N1)=CC=C1NCC1=C(F)C=CC=C1F JGEVQLZYMJHDLP-UHFFFAOYSA-N 0.000 claims 1
• 208000019693 Lung disease Diseases 0.000 claims 1
• YDIKJVJDOQLUNR-UHFFFAOYSA-N n-(2,6-difluorophenyl)-1-methyl-5-[2-methyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]pyrrole-2-carboxamide Chemical compound CC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N1C)=CC=C1C(=O)NC1=C(F)C=CC=C1F YDIKJVJDOQLUNR-UHFFFAOYSA-N 0.000 claims 1
• UQKOVHQHWZMKST-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]benzamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UQKOVHQHWZMKST-UHFFFAOYSA-N 0.000 claims 1
• UAUJRKSKWQZDFO-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[3-ethyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]benzamide Chemical compound CCC1=C(C=2OC(=O)N(C)N=2)C=CN=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UAUJRKSKWQZDFO-UHFFFAOYSA-N 0.000 claims 1
• LZJUGNCGBRHAGD-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[4-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]benzamide Chemical compound CCC1=C(C=2OC(=O)N(C)N=2)C=NC=C1C(C=C1)=CC=C1C(=O)NC1=C(F)C=CC=C1F LZJUGNCGBRHAGD-UHFFFAOYSA-N 0.000 claims 1
• UUVVTEOEHRECCA-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4-[5-ethyl-4-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-2-yl]benzamide Chemical compound CCC1=CN=C(C=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2F)F)C=C1C1=NN(C)C(=O)O1 UUVVTEOEHRECCA-UHFFFAOYSA-N 0.000 claims 1
• UXPICKRHSZKBNE-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-(methylamino)-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(S1)=CC=C1C(=O)NC1=C(F)C=CC=C1F UXPICKRHSZKBNE-UHFFFAOYSA-N 0.000 claims 1
• UDVOMFANSRHYON-UHFFFAOYSA-N n-(2,6-difluorophenyl)-5-[2-ethyl-5-(4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)pyridin-3-yl]-1-methylpyrrole-2-carboxamide Chemical compound CCC1=NC=C(C=2OC(=O)N(C)N=2)C=C1C(N1C)=CC=C1C(=O)NC1=C(F)C=CC=C1F UDVOMFANSRHYON-UHFFFAOYSA-N 0.000 claims 1
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