AU2008318491B2 - Cytokine inhibitors - Google Patents
Cytokine inhibitors Download PDFInfo
- Publication number
- AU2008318491B2 AU2008318491B2 AU2008318491A AU2008318491A AU2008318491B2 AU 2008318491 B2 AU2008318491 B2 AU 2008318491B2 AU 2008318491 A AU2008318491 A AU 2008318491A AU 2008318491 A AU2008318491 A AU 2008318491A AU 2008318491 B2 AU2008318491 B2 AU 2008318491B2
- Authority
- AU
- Australia
- Prior art keywords
- imidazo
- phenyl
- pyridazin
- oxadiazol
- compound
- Prior art date
- 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.)
- Ceased
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- 102000004127 Cytokines Human genes 0.000 title claims abstract description 25
- 108090000695 Cytokines Proteins 0.000 title claims abstract description 25
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 238000000034 method Methods 0.000 claims abstract description 31
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 8
- 238000012261 overproduction Methods 0.000 claims abstract description 7
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 62
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 35
- -1 C 1 I 10 haloalkyl Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 15
- 125000003106 haloaryl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 101100240985 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nrc-2 gene Proteins 0.000 claims description 10
- OXSABAZYSCHBEW-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=C=CC=C2N=C[CH]N21 OXSABAZYSCHBEW-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 108010002352 Interleukin-1 Proteins 0.000 claims description 4
- 102000000589 Interleukin-1 Human genes 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 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 3
- 101100150274 Caenorhabditis elegans srb-2 gene Proteins 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
- 108010002350 Interleukin-2 Proteins 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
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 3
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 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
- 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 3
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- RCOJRSOHHFTHDJ-UHFFFAOYSA-N 1,2,4-oxadiazole-5-carboxamide Chemical compound NC(=O)C1=NC=NO1 RCOJRSOHHFTHDJ-UHFFFAOYSA-N 0.000 claims description 2
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PWDBBZCSOVRMQM-UHFFFAOYSA-N 2-methoxy-n-[[3-[3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]ethanamine Chemical compound O1C(CNCCOC)=NC(C=2C=C(C=CC=2)C=2N=C3SC(C)=CN3C=2)=N1 PWDBBZCSOVRMQM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- JXFACLVJTUIGDP-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 JXFACLVJTUIGDP-UHFFFAOYSA-N 0.000 claims description 2
- NDEZROCTPTYFCC-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-n-(2-methoxyethyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NCCOC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 NDEZROCTPTYFCC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- AXXQLSWJYXVVCM-UHFFFAOYSA-N 3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-n-methyl-1,2,4-oxadiazole-5-carboxamide Chemical compound O1C(C(=O)NC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 AXXQLSWJYXVVCM-UHFFFAOYSA-N 0.000 claims description 2
- YYUWLYIBMVXGOY-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylic acid Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(C(O)=O)=N1 YYUWLYIBMVXGOY-UHFFFAOYSA-N 0.000 claims description 2
- MUCPHMGJNFHLTC-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-5-(methoxymethyl)-1,2,4-oxadiazole Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(COC)=N1 MUCPHMGJNFHLTC-UHFFFAOYSA-N 0.000 claims description 2
- XHNHQZXUVYGKNU-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(C(F)(F)F)=N1 XHNHQZXUVYGKNU-UHFFFAOYSA-N 0.000 claims description 2
- AKNJHOUGTCCDSA-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-n-(2,2,2-trifluoroethyl)-1,2,4-oxadiazole-5-carboxamide Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(C(=O)NCC(F)(F)F)=N1 AKNJHOUGTCCDSA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- CUNUPDZFTBJWHW-UHFFFAOYSA-N 5-(ethoxymethyl)-3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-1,2,4-oxadiazole Chemical compound O1C(COCC)=NC(C=2C=C(C=C(OCCOC)C=2)C=2N=C3C=CC=NN3C=2)=N1 CUNUPDZFTBJWHW-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 108090001005 Interleukin-6 Proteins 0.000 claims description 2
- 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 2
- MCIAGYYQYMUMPU-UHFFFAOYSA-N [3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl acetate Chemical compound O1C(COC(=O)C)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 MCIAGYYQYMUMPU-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 2
- 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 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- JWHCQCCUBQIHRR-UHFFFAOYSA-N n-[3-imidazo[1,2-b]pyridazin-2-yl-5-[5-(piperazin-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=1CN1CCNCC1 JWHCQCCUBQIHRR-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- VQXNZTAAWFLMBP-UHFFFAOYSA-N 2,2,2-trifluoro-n-[[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C(F)(F)F)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 VQXNZTAAWFLMBP-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/934,154 US7868001B2 (en) | 2007-11-02 | 2007-11-02 | Cytokine inhibitors |
| US11/934,154 | 2007-11-02 | ||
| PCT/US2008/082027 WO2009059162A1 (en) | 2007-11-02 | 2008-10-31 | Cytokine inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2008318491A1 AU2008318491A1 (en) | 2009-05-07 |
| AU2008318491B2 true AU2008318491B2 (en) | 2013-09-19 |
Family
ID=40588767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008318491A Ceased AU2008318491B2 (en) | 2007-11-02 | 2008-10-31 | Cytokine inhibitors |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7868001B2 (https=) |
| EP (1) | EP2214669B1 (https=) |
| JP (1) | JP5733982B2 (https=) |
| KR (1) | KR20100101581A (https=) |
| AU (1) | AU2008318491B2 (https=) |
| CA (1) | CA2704431A1 (https=) |
| MX (1) | MX2010004774A (https=) |
| MY (1) | MY153065A (https=) |
| RU (1) | RU2485113C2 (https=) |
| TW (1) | TWI419692B (https=) |
| WO (1) | WO2009059162A1 (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066861Y2 (ja) | 1991-02-19 | 1994-02-23 | 太陽電子株式会社 | パチンコ式組合せゲーム機 |
| IL266563B (en) | 2009-10-06 | 2022-09-01 | Millennium Pharm Inc | Heterocyclic compounds useful as pdk1 inhibitors |
| WO2011137587A1 (en) * | 2010-05-06 | 2011-11-10 | Hutchison Medipharma Limited | Cytokine inhibitors |
| FR2962649B1 (fr) | 2010-07-19 | 2025-10-24 | Conservatoire Nat Arts Et Metiers | Traitement d'une pathologie liee a un effet excessif du tnf par un compose de benzene sulfonamide |
| HUE038169T2 (hu) | 2013-09-06 | 2018-09-28 | Aurigene Discovery Tech Ltd | 1,2,4-Oxadiazol származékok mint immunomodulátorok |
| EA201650031A1 (ru) | 2014-05-15 | 2017-06-30 | Итеос Терапьютик | Производные пирролидин-2,5-диона, фармацевтические композиции и способы применения в качестве ингибиторов ido1 |
| KR102302109B1 (ko) * | 2014-07-24 | 2021-09-14 | 삼성디스플레이 주식회사 | 유기 화합물 및 이를 포함하는 유기 발광 장치 |
| KR102894264B1 (ko) | 2015-03-10 | 2025-12-02 | 오리진 온콜로지 리미티드 | 면역조절제로서의 1,2,4-옥사다이아졸 및 티아다이아졸 화합물 |
| MX2017011951A (es) | 2015-03-17 | 2018-06-15 | Pfizer | Derivados sustituidos de indol 3 novedosos, composiciones farmaceuticas y metodos para uso. |
| EP3334733A1 (en) | 2015-08-10 | 2018-06-20 | Pfizer Inc | 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA44075A (fr) | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2214669B1 (en) | 2015-04-01 |
| TWI419692B (zh) | 2013-12-21 |
| AU2008318491A1 (en) | 2009-05-07 |
| RU2485113C2 (ru) | 2013-06-20 |
| MX2010004774A (es) | 2010-07-02 |
| RU2010122333A (ru) | 2011-12-10 |
| TW201002327A (en) | 2010-01-16 |
| US7868001B2 (en) | 2011-01-11 |
| MY153065A (en) | 2014-12-31 |
| WO2009059162A1 (en) | 2009-05-07 |
| US20090118292A1 (en) | 2009-05-07 |
| JP5733982B2 (ja) | 2015-06-10 |
| EP2214669A4 (en) | 2011-11-09 |
| KR20100101581A (ko) | 2010-09-17 |
| CA2704431A1 (en) | 2009-05-07 |
| EP2214669A1 (en) | 2010-08-11 |
| JP2011502996A (ja) | 2011-01-27 |
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