JP5733982B2 - サイトカインの産生を抑制する化合物及びその調製方法 - Google Patents

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Publication number

JP5733982B2

JP5733982B2 JP2010532289A JP2010532289A JP5733982B2 JP 5733982 B2 JP5733982 B2 JP 5733982B2 JP 2010532289 A JP2010532289 A JP 2010532289A JP 2010532289 A JP2010532289 A JP 2010532289A JP 5733982 B2 JP5733982 B2 JP 5733982B2

Authority

JP

Japan

Prior art keywords

imidazo

phenyl

pyridazin

oxadiazol

methyl

Prior art date

2007-11-02

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 89
• 238000000034 method Methods 0.000 title claims description 30
• 230000016396 cytokine production Effects 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims description 57
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
• -1 and R 3 is H Chemical group 0.000 claims description 43
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000001188 haloalkyl group Chemical group 0.000 claims description 40
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 24
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 102000004127 Cytokines Human genes 0.000 claims description 20
• 108090000695 Cytokines Proteins 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 16
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 15
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
• 125000003106 haloaryl group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• MYVSUIXAYJQREI-UHFFFAOYSA-N 4-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]morpholine Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CN1CCOCC1 MYVSUIXAYJQREI-UHFFFAOYSA-N 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
• CNXURQCAZYNLDR-UHFFFAOYSA-N n-[3-imidazo[1,2-b]pyridazin-2-yl-5-[5-(piperidin-1-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanesulfonamide Chemical compound C=1C(NS(=O)(=O)C)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C(N=1)=NOC=1CN1CCCCC1 CNXURQCAZYNLDR-UHFFFAOYSA-N 0.000 claims description 6
• 238000012261 overproduction Methods 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 230000001404 mediated effect Effects 0.000 claims description 4
• ZZQLGVCPIFVVSV-UHFFFAOYSA-N n-methyl-2-[3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1N2N=C(NC)C=CC2=NC=1C(C=1)=CC=CC=1C1=NOC(C(F)(F)F)=N1 ZZQLGVCPIFVVSV-UHFFFAOYSA-N 0.000 claims description 4
• XFGCZYZMCZITNG-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NO1 XFGCZYZMCZITNG-UHFFFAOYSA-N 0.000 claims description 3
• CDWWZVZYEBPBMQ-UHFFFAOYSA-N 1-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-n,n-dimethylmethanamine Chemical compound O1C(CN(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 CDWWZVZYEBPBMQ-UHFFFAOYSA-N 0.000 claims description 3
• MUDXEYBTMWKWDH-UHFFFAOYSA-N 2-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-1-morpholin-4-ylethanone Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CC(=O)N1CCOCC1 MUDXEYBTMWKWDH-UHFFFAOYSA-N 0.000 claims description 3
• XHFNBOHOMFRLBA-UHFFFAOYSA-N 2-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]acetic acid Chemical compound O1C(CC(=O)O)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 XHFNBOHOMFRLBA-UHFFFAOYSA-N 0.000 claims description 3
• BNUIDEHBQILQPB-UHFFFAOYSA-N 2-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methylamino]ethanol Chemical compound O1C(CNCCO)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 BNUIDEHBQILQPB-UHFFFAOYSA-N 0.000 claims description 3
• FDIRZNNHMTZYJV-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)N)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 FDIRZNNHMTZYJV-UHFFFAOYSA-N 0.000 claims description 3
• UDDTTWFCVWUKNL-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxylic acid Chemical compound O1C(C(=O)O)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 UDDTTWFCVWUKNL-UHFFFAOYSA-N 0.000 claims description 3
• DMJPSDAEGZSGDL-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-(methoxymethyl)-1,2,4-oxadiazole Chemical compound O1C(COC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 DMJPSDAEGZSGDL-UHFFFAOYSA-N 0.000 claims description 3
• QJQRWLCIESXICZ-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-(methylsulfanylmethyl)-1,2,4-oxadiazole Chemical compound O1C(CSC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 QJQRWLCIESXICZ-UHFFFAOYSA-N 0.000 claims description 3
• XVCAOEBVIBRRMU-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-(methylsulfonylmethyl)-1,2,4-oxadiazole Chemical compound O1C(CS(=O)(=O)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 XVCAOEBVIBRRMU-UHFFFAOYSA-N 0.000 claims description 3
• ZEBVDFOGBZJVKC-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-(piperazin-1-ylmethyl)-1,2,4-oxadiazole Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CN1CCNCC1 ZEBVDFOGBZJVKC-UHFFFAOYSA-N 0.000 claims description 3
• OHFCRYSWZDMFLV-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1C(C(F)(F)F)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 OHFCRYSWZDMFLV-UHFFFAOYSA-N 0.000 claims description 3
• PUEFFLRBJGCSSM-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-propan-2-yl-1,2,4-oxadiazole Chemical compound O1C(C(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 PUEFFLRBJGCSSM-UHFFFAOYSA-N 0.000 claims description 3
• HGVLPPFRIOCNAA-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-n,n-dimethyl-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)N(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 HGVLPPFRIOCNAA-UHFFFAOYSA-N 0.000 claims description 3
• NNBUMNVVNBUAHQ-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-n-(2-morpholin-4-ylethyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1C(=O)NCCN1CCOCC1 NNBUMNVVNBUAHQ-UHFFFAOYSA-N 0.000 claims description 3
• JDQJZWUYXGIHHS-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-n-(thiophen-2-ylmethyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1C(=O)NCC1=CC=CS1 JDQJZWUYXGIHHS-UHFFFAOYSA-N 0.000 claims description 3
• RCGIORZRZAUVAC-UHFFFAOYSA-N 5-(ethoxymethyl)-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole Chemical compound O1C(COCC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 RCGIORZRZAUVAC-UHFFFAOYSA-N 0.000 claims description 3
• XBQAZEXDFFJFNN-UHFFFAOYSA-N 5-(fluoromethyl)-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole Chemical compound O1C(CF)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 XBQAZEXDFFJFNN-UHFFFAOYSA-N 0.000 claims description 3
• JPWLGKSCPIYEIN-UHFFFAOYSA-N 5-[(4-fluorophenoxy)methyl]-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1OCC1=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NO1 JPWLGKSCPIYEIN-UHFFFAOYSA-N 0.000 claims description 3
• PTTOHJPVEZOABW-UHFFFAOYSA-N 5-cyclopropyl-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole Chemical compound C1CC1C1=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NO1 PTTOHJPVEZOABW-UHFFFAOYSA-N 0.000 claims description 3
• DAIHEXRLOPDCQK-UHFFFAOYSA-N 5-ethyl-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 DAIHEXRLOPDCQK-UHFFFAOYSA-N 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010020751 Hypersensitivity Diseases 0.000 claims description 3
• 108010063738 Interleukins Proteins 0.000 claims description 3
• 102000015696 Interleukins Human genes 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010040070 Septic Shock Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• VVYOCCRJBICVAO-UHFFFAOYSA-N [3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-morpholin-4-ylmethanone Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1C(=O)N1CCOCC1 VVYOCCRJBICVAO-UHFFFAOYSA-N 0.000 claims description 3
• IQYHONOVDRUYFW-UHFFFAOYSA-N [3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-pyrrolidin-1-ylmethanone Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1C(=O)N1CCCC1 IQYHONOVDRUYFW-UHFFFAOYSA-N 0.000 claims description 3
• WPEACOCTYYOQIK-UHFFFAOYSA-N [3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methanol Chemical compound O1C(CO)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 WPEACOCTYYOQIK-UHFFFAOYSA-N 0.000 claims description 3
• SFXRLQPKVCNPMK-UHFFFAOYSA-N [3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methanamine Chemical compound COCCOC1=CC(CN)=CC(C=2N=C3C=CC=NN3C=2)=C1 SFXRLQPKVCNPMK-UHFFFAOYSA-N 0.000 claims description 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
• 230000007815 allergy Effects 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• LKXJXDCNHQUSAE-UHFFFAOYSA-N ethyl 2-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methylamino]-2-oxoacetate Chemical compound O1C(CNC(=O)C(=O)OCC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 LKXJXDCNHQUSAE-UHFFFAOYSA-N 0.000 claims description 3
• OQORVHMMUBEIGD-UHFFFAOYSA-N ethyl 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxylate Chemical compound O1C(C(=O)OCC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 OQORVHMMUBEIGD-UHFFFAOYSA-N 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• IOLGFFULGXBKQW-UHFFFAOYSA-N n'-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]ethane-1,2-diamine Chemical compound O1C(CNCCN)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 IOLGFFULGXBKQW-UHFFFAOYSA-N 0.000 claims description 3
• GOOGZBNBHRZBMM-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NCCO)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 GOOGZBNBHRZBMM-UHFFFAOYSA-N 0.000 claims description 3
• HVSFZPSEGPQGPJ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NCCN(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 HVSFZPSEGPQGPJ-UHFFFAOYSA-N 0.000 claims description 3
• VQUCVPMHWBLFCC-UHFFFAOYSA-N n-[3-[5-(aminomethyl)-1,2,4-oxadiazol-3-yl]-5-imidazo[1,2-b]pyridazin-2-ylphenyl]methanesulfonamide Chemical compound C=1C(NS(=O)(=O)C)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(CN)=N1 VQUCVPMHWBLFCC-UHFFFAOYSA-N 0.000 claims description 3
• AEDZVEIUKYDCAB-UHFFFAOYSA-N n-[3-imidazo[1,2-b]pyridazin-2-yl-5-[5-(morpholin-4-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanesulfonamide Chemical compound C=1C(NS(=O)(=O)C)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C(N=1)=NOC=1CN1CCOCC1 AEDZVEIUKYDCAB-UHFFFAOYSA-N 0.000 claims description 3
• WSSKWSWVWTXECN-UHFFFAOYSA-N n-[3-imidazo[1,2-b]pyridazin-2-yl-5-[5-[(2-methoxyethylamino)methyl]-1,2,4-oxadiazol-3-yl]phenyl]methanesulfonamide Chemical compound O1C(CNCCOC)=NC(C=2C=C(C=C(NS(C)(=O)=O)C=2)C=2N=C3C=CC=NN3C=2)=N1 WSSKWSWVWTXECN-UHFFFAOYSA-N 0.000 claims description 3
• RABRMNFHQDDOCZ-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-2-methoxyacetamide Chemical compound O1C(CNC(=O)COC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 RABRMNFHQDDOCZ-UHFFFAOYSA-N 0.000 claims description 3
• PJAUUXPPCYUOSC-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-2-methoxyethanamine Chemical compound O1C(CNCCOC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 PJAUUXPPCYUOSC-UHFFFAOYSA-N 0.000 claims description 3
• OSBITWLZDFBBGY-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-2-methylpropanamide Chemical compound O1C(CNC(=O)C(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 OSBITWLZDFBBGY-UHFFFAOYSA-N 0.000 claims description 3
• WBHHNGKDPXRDJI-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-2-morpholin-4-ylethanamine Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CNCCN1CCOCC1 WBHHNGKDPXRDJI-UHFFFAOYSA-N 0.000 claims description 3
• RTNJZCUIXZSJQF-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound O1C(CNCCN(C)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 RTNJZCUIXZSJQF-UHFFFAOYSA-N 0.000 claims description 3
• UZDIPNKXVTURNC-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]cyclopentanecarboxamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CNC(=O)C1CCCC1 UZDIPNKXVTURNC-UHFFFAOYSA-N 0.000 claims description 3
• VTULISXAZGKXEE-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]cyclopropanecarboxamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CNC(=O)C1CC1 VTULISXAZGKXEE-UHFFFAOYSA-N 0.000 claims description 3
• KRMJCXXFKGPNFP-UHFFFAOYSA-N n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]ethanamine Chemical compound O1C(CNCC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 KRMJCXXFKGPNFP-UHFFFAOYSA-N 0.000 claims description 3
• LVJLBKCRGWMJMW-UHFFFAOYSA-N n-[[3-[3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]-1-(4-methylsulfonylphenyl)methanamine Chemical compound N1=C2SC(C)=CN2C=C1C(C=1)=CC=CC=1C(N=1)=NOC=1CNCC1=CC=C(S(C)(=O)=O)C=C1 LVJLBKCRGWMJMW-UHFFFAOYSA-N 0.000 claims description 3
• LZUJMFQZUMTEOL-UHFFFAOYSA-N n-cyclopentyl-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1C(=O)NC1CCCC1 LZUJMFQZUMTEOL-UHFFFAOYSA-N 0.000 claims description 3
• OEIQJSZSMZBAPR-UHFFFAOYSA-N n-ethyl-3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NCC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 OEIQJSZSMZBAPR-UHFFFAOYSA-N 0.000 claims description 3
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