JP2011502996A5 - - Google Patents
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- JP2011502996A5 JP2011502996A5 JP2010532289A JP2010532289A JP2011502996A5 JP 2011502996 A5 JP2011502996 A5 JP 2011502996A5 JP 2010532289 A JP2010532289 A JP 2010532289A JP 2010532289 A JP2010532289 A JP 2010532289A JP 2011502996 A5 JP2011502996 A5 JP 2011502996A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- phenyl
- pyridazin
- oxadiazol
- alkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 19
- 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 2
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- -1 and R 3 is H Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000003106 haloaryl group Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 108090000695 Cytokines Proteins 0.000 claims 4
- 102000004127 Cytokines Human genes 0.000 claims 4
- 108010063738 Interleukins Proteins 0.000 claims 4
- 102000015696 Interleukins Human genes 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 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 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 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 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 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 1
- VOBIYBSROYKPSK-UHFFFAOYSA-N 1-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]-3-(2-methoxyethyl)urea Chemical compound COCCNC(=O)NCC1=CC=CC(C=2N=C3C=CC=NN3C=2)=C1 VOBIYBSROYKPSK-UHFFFAOYSA-N 0.000 claims 1
- RHWJKWDPCFRAQY-UHFFFAOYSA-N 1-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound C=1C=CC(C=2N=C3C=CC=NN3C=2)=CC=1CNC(=O)NCCN1CCOCC1 RHWJKWDPCFRAQY-UHFFFAOYSA-N 0.000 claims 1
- HFPOAOPFFCFTLR-UHFFFAOYSA-N 1-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]-3-(thiophen-2-ylmethyl)urea Chemical compound C=1C=CC(C=2N=C3C=CC=NN3C=2)=CC=1CNC(=O)NCC1=CC=CS1 HFPOAOPFFCFTLR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SXGYCEMPBZRAHN-UHFFFAOYSA-N 2,2,2-trifluoro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]acetamide Chemical compound COCCOC1=CC(CNC(=O)C(F)(F)F)=CC(C=2N=C3C=CC=NN3C=2)=C1 SXGYCEMPBZRAHN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- NNSNDWIWJGASMJ-UHFFFAOYSA-N 2-chloro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]acetamide Chemical compound COCCOC1=CC(CNC(=O)CCl)=CC(C=2N=C3C=CC=NN3C=2)=C1 NNSNDWIWJGASMJ-UHFFFAOYSA-N 0.000 claims 1
- QSWWINLYWVHBSN-UHFFFAOYSA-N 2-fluoro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzenesulfonamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNS(=O)(=O)C1=CC=CC=C1F QSWWINLYWVHBSN-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RYPRUBNQCXNMJF-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-1,2,4-oxadiazole-5-carboxamide Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(C(N)=O)=N1 RYPRUBNQCXNMJF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- SZROAHNZSADXEY-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-5-methyl-1,2,4-oxadiazole Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(C)=N1 SZROAHNZSADXEY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZHDPBEHUMASYKB-UHFFFAOYSA-N 3-[[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methylamino]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CNCC=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=C1 ZHDPBEHUMASYKB-UHFFFAOYSA-N 0.000 claims 1
- NDXIYLGWDGOLAZ-UHFFFAOYSA-N 3-bromo-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNC(=O)C1=CC=CC(Br)=C1 NDXIYLGWDGOLAZ-UHFFFAOYSA-N 0.000 claims 1
- JMXXXKFPHFKOBA-UHFFFAOYSA-N 3-chloro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzenesulfonamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNS(=O)(=O)C1=CC=CC(Cl)=C1 JMXXXKFPHFKOBA-UHFFFAOYSA-N 0.000 claims 1
- GNYBPMZJPCAJEQ-UHFFFAOYSA-N 3-cyano-n-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]benzenesulfonamide Chemical compound C=1C=CC(C=2N=C3C=CC=NN3C=2)=CC=1CNS(=O)(=O)C1=CC=CC(C#N)=C1 GNYBPMZJPCAJEQ-UHFFFAOYSA-N 0.000 claims 1
- BYJYYWFRADTTPM-UHFFFAOYSA-N 4-chloro-n-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=CC(C=2N=C3C=CC=NN3C=2)=C1 BYJYYWFRADTTPM-UHFFFAOYSA-N 0.000 claims 1
- OLQKHGCRUFSLNI-UHFFFAOYSA-N 4-chloro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNC(=O)C1=CC=C(Cl)C=C1 OLQKHGCRUFSLNI-UHFFFAOYSA-N 0.000 claims 1
- YTLCTVVDXMWMOP-UHFFFAOYSA-N 4-cyano-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNC(=O)C1=CC=C(C#N)C=C1 YTLCTVVDXMWMOP-UHFFFAOYSA-N 0.000 claims 1
- OOXDRBHANHMILT-UHFFFAOYSA-N 4-fluoro-n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]benzenesulfonamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNS(=O)(=O)C1=CC=C(F)C=C1 OOXDRBHANHMILT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ZXJRZUTUVXBIRE-UHFFFAOYSA-N 5-(fluoromethyl)-3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-1,2,4-oxadiazole Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(CF)=N1 ZXJRZUTUVXBIRE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- BPZVVLMPFUZHDH-UHFFFAOYSA-N N-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]acetamide Chemical compound C(C)(=O)NC1=NC(=NO1)C1=CC(=CC=C1)C=1N=C2N(N=CC=C2)C=1 BPZVVLMPFUZHDH-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- LUQOFLDYXRZMQC-UHFFFAOYSA-N [2-(3-imidazo[1,2-b]pyridazin-2-ylanilino)pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=CN=C(NC=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)C=1C(=O)N1CCOCC1 LUQOFLDYXRZMQC-UHFFFAOYSA-N 0.000 claims 1
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| 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 |
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| 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 |
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| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018118781A1 (en) * | 2016-12-20 | 2018-06-28 | Fmc Corporation | Fungicidal oxadiazoles |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| LT3558990T (lt) | 2016-12-22 | 2022-12-27 | Incyte Corporation | Tetrahidroimidazo[4,5-c]piridino dariniai kaip pd-l1 internalizavimo induktoriai |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
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| WO2019061324A1 (en) | 2017-09-29 | 2019-04-04 | Curis Inc. | CRYSTALLINE FORMS OF IMMUNOMODULATORS |
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| US20220267270A1 (en) * | 2019-08-30 | 2022-08-25 | University Of South Florida | Sting modulators, compositions, and methods of use |
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| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
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-
2007
- 2007-11-02 US US11/934,154 patent/US7868001B2/en not_active Expired - Fee Related
-
2008
- 2008-07-04 TW TW097125251A patent/TWI419692B/zh not_active IP Right Cessation
- 2008-10-31 RU RU2010122333/04A patent/RU2485113C2/ru not_active IP Right Cessation
- 2008-10-31 MY MYPI20101943 patent/MY153065A/en unknown
- 2008-10-31 WO PCT/US2008/082027 patent/WO2009059162A1/en not_active Ceased
- 2008-10-31 KR KR1020107011579A patent/KR20100101581A/ko not_active Abandoned
- 2008-10-31 EP EP08843535.9A patent/EP2214669B1/en not_active Not-in-force
- 2008-10-31 AU AU2008318491A patent/AU2008318491B2/en not_active Ceased
- 2008-10-31 JP JP2010532289A patent/JP5733982B2/ja not_active Expired - Fee Related
- 2008-10-31 CA CA2704431A patent/CA2704431A1/en not_active Abandoned
- 2008-10-31 MX MX2010004774A patent/MX2010004774A/es active IP Right Grant
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