JP2011502996A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- NNHNTWIYBDZKND-UHFFFAOYSA-N [2-(3-imidazo[1,2-b]pyridazin-2-ylanilino)pyridin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=CN=C(NC=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)C=1C(=O)N1CCCC1 NNHNTWIYBDZKND-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- HEGUKUBMSVANSO-UHFFFAOYSA-N [3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-1,2,4-oxadiazol-5-yl]methanol Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C1=NOC(CO)=N1 HEGUKUBMSVANSO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LJSGLEVVMDHAGH-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 LJSGLEVVMDHAGH-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 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 1
- 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 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 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 1
- 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 1
- DCIDXXSRVSHTLE-UHFFFAOYSA-N n-[(3-imidazo[1,2-b]pyridazin-2-ylphenyl)methyl]-2-methoxyacetamide Chemical compound COCC(=O)NCC1=CC=CC(C=2N=C3C=CC=NN3C=2)=C1 DCIDXXSRVSHTLE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- NROHKVPZUQWXLM-UHFFFAOYSA-N n-[3-[5-[[2-(dimethylamino)ethylamino]methyl]-1,2,4-oxadiazol-3-yl]-5-imidazo[1,2-b]pyridazin-2-ylphenyl]methanesulfonamide Chemical compound O1C(CNCCN(C)C)=NC(C=2C=C(C=C(NS(C)(=O)=O)C=2)C=2N=C3C=CC=NN3C=2)=N1 NROHKVPZUQWXLM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- CVDXTQXKCWDJCS-UHFFFAOYSA-N n-[[3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]methyl]butanamide Chemical compound CCCC(=O)NCC1=CC=CC(C=2N=C3SC(C)=CN3C=2)=C1 CVDXTQXKCWDJCS-UHFFFAOYSA-N 0.000 claims 1
- LRAKTJWTFRAYJH-UHFFFAOYSA-N n-[[3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]methyl]cyclopropanecarboxamide Chemical compound N1=C2SC(C)=CN2C=C1C(C=1)=CC=CC=1CNC(=O)C1CC1 LRAKTJWTFRAYJH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- JLJDYVUUOWTDJJ-UHFFFAOYSA-N n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]-3-nitrobenzenesulfonamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 JLJDYVUUOWTDJJ-UHFFFAOYSA-N 0.000 claims 1
- AGKPRBBPMRZAHX-UHFFFAOYSA-N n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]-4-methylbenzenesulfonamide Chemical compound C=1C(C=2N=C3C=CC=NN3C=2)=CC(OCCOC)=CC=1CNS(=O)(=O)C1=CC=C(C)C=C1 AGKPRBBPMRZAHX-UHFFFAOYSA-N 0.000 claims 1
- MFXYJRWGJADPTB-UHFFFAOYSA-N n-[[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]methyl]acetamide Chemical compound COCCOC1=CC(CNC(C)=O)=CC(C=2N=C3C=CC=NN3C=2)=C1 MFXYJRWGJADPTB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 238000012261 overproduction Methods 0.000 claims 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/934,154 | 2007-11-02 | ||
| US11/934,154 US7868001B2 (en) | 2007-11-02 | 2007-11-02 | Cytokine inhibitors |
| PCT/US2008/082027 WO2009059162A1 (en) | 2007-11-02 | 2008-10-31 | Cytokine inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011502996A JP2011502996A (ja) | 2011-01-27 |
| JP2011502996A5 true JP2011502996A5 (enExample) | 2011-12-08 |
| JP5733982B2 JP5733982B2 (ja) | 2015-06-10 |
Family
ID=40588767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010532289A Expired - Fee Related JP5733982B2 (ja) | 2007-11-02 | 2008-10-31 | 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 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7868001B2 (enExample) |
| EP (1) | EP2214669B1 (enExample) |
| JP (1) | JP5733982B2 (enExample) |
| KR (1) | KR20100101581A (enExample) |
| AU (1) | AU2008318491B2 (enExample) |
| CA (1) | CA2704431A1 (enExample) |
| MX (1) | MX2010004774A (enExample) |
| MY (1) | MY153065A (enExample) |
| RU (1) | RU2485113C2 (enExample) |
| TW (1) | TWI419692B (enExample) |
| WO (1) | WO2009059162A1 (enExample) |
Families Citing this family (40)
| 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 |
| PL2485731T4 (pl) * | 2009-10-06 | 2017-07-31 | Millennium Pharmaceuticals, Inc. | Związki heterocykliczne użyteczne jako inhibitory PDK1 |
| 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 |
| RS57508B1 (sr) | 2013-09-06 | 2018-10-31 | Aurigene Discovery Tech Ltd | 1,2,4-derivati oksadiazola kao imunomodulatori |
| 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 |
| BR112017019699A2 (pt) | 2015-03-17 | 2018-09-04 | Pfizer Inc. | derivados substituídos por 3-indol, composições farmacêuticas e métodos para uso |
| US10544095B2 (en) | 2015-08-10 | 2020-01-28 | Pfizer Inc. | 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MD3377488T2 (ro) | 2015-11-19 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| CA3009474A1 (en) | 2015-12-22 | 2017-06-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2906460T3 (es) | 2016-05-06 | 2022-04-18 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA45669A (fr) | 2016-07-14 | 2019-05-22 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018118781A1 (en) * | 2016-12-20 | 2018-06-28 | Fmc Corporation | Fungicidal oxadiazoles |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP4223369A1 (en) | 2016-12-22 | 2023-08-09 | Incyte Corporation | Immunomodulator compounds and methods of use |
| US10308644B2 (en) | 2016-12-22 | 2019-06-04 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| WO2019061324A1 (en) | 2017-09-29 | 2019-04-04 | Curis Inc. | CRYSTALLINE FORMS OF IMMUNOMODULATORS |
| AU2018348350B2 (en) | 2017-10-11 | 2024-05-02 | Aurigene Oncology Limited | Crystalline forms of 3-substituted 1,2,4-oxadiazole |
| MX2020004531A (es) | 2017-11-03 | 2020-08-03 | Aurigene Discovery Tech Ltd | Inhibidores dobles de tim-3 y las vias de pd-1. |
| EP3706798A1 (en) | 2017-11-06 | 2020-09-16 | Aurigene Discovery Technologies Limited | Conjoint therapies for immunomodulation |
| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| CN112752756B (zh) | 2018-05-11 | 2024-06-25 | 因赛特公司 | 作为PD-L1免疫调节剂的四氢-咪唑并[4,5-c]吡啶衍生物 |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| US20220267270A1 (en) * | 2019-08-30 | 2022-08-25 | University Of South Florida | Sting modulators, compositions, and methods of use |
| JP7559059B2 (ja) | 2019-09-30 | 2024-10-01 | インサイト・コーポレイション | 免疫調節剤としてのピリド［３，２－ｄ］ピリミジン化合物 |
| EP4058461A1 (en) | 2019-11-11 | 2022-09-21 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| IL297963A (en) | 2020-05-07 | 2023-01-01 | Adorx Therapeutics Ltd | Antagonists of the adenosine a2a receptor |
| IL302590A (en) | 2020-11-06 | 2023-07-01 | Incyte Corp | Process for preparing PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| GB202019622D0 (en) * | 2020-12-11 | 2021-01-27 | Adorx Therapeutics Ltd | Antagonist compounds |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5745237B2 (enExample) * | 1974-03-27 | 1982-09-27 | ||
| GB1442707A (en) * | 1973-07-07 | 1976-07-14 | Yoshitomi Pharmaceutical | Substituted phenylalkanoic acids and their derivatives and pharma ceutical compositions thereof |
| DE3446812A1 (de) | 1984-12-21 | 1986-06-26 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| DE3446778A1 (de) | 1984-12-21 | 1986-07-03 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| IL86462A (en) * | 1987-05-29 | 1992-12-01 | Fujisawa Pharmaceutical Co | Alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical compositions comprising the same |
| WO1989001478A1 (en) * | 1987-08-07 | 1989-02-23 | The Australian National University | ARYLOXY- AND ARALKYLTHIO-IMIDAZO[1,2-b]PYRIDAZINES |
| DE4405378A1 (de) * | 1994-02-19 | 1995-08-24 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| JPH07291976A (ja) * | 1994-04-27 | 1995-11-07 | Otsuka Pharmaceut Factory Inc | イミダゾ〔２，１−ｂ〕チアゾール誘導体 |
| JP3477238B2 (ja) * | 1994-04-27 | 2003-12-10 | 株式会社大塚製薬工場 | イミダゾ〔１，２−ａ〕ピリジン誘導体 |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| DE60010448T2 (de) * | 1999-03-17 | 2005-04-07 | Astrazeneca Ab | Amid-derivate |
| US6403567B1 (en) | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| CA2397661C (en) * | 2000-03-01 | 2012-01-03 | Janssen Pharmaceutica N.V. | 2,4-disubstituted thiazolyl derivatives |
| WO2002049632A1 (en) * | 2000-12-18 | 2002-06-27 | Institute Of Medicinal Molecular Design. Inc. | Inhibitors against the production and release of inflammatory cytokines |
| US6596731B2 (en) * | 2001-03-27 | 2003-07-22 | Hoffmann-La Roche Inc. | Substituted imidazo[1,2-A] pyridine derivatives |
| CA2450555A1 (en) * | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| EP1426050A4 (en) * | 2001-08-23 | 2005-05-25 | Takeda Pharmaceutical | JNK INHIBITORS |
| ATE511858T1 (de) * | 2002-02-05 | 2011-06-15 | Astellas Pharma Inc | 2,4,6-triamino-1,3,5-triazin-derivat |
| US7105533B2 (en) * | 2002-09-13 | 2006-09-12 | Merck & Co., Inc. | Fused heterobicyclo substituted phenyl metabotropic glutamate-5 modulators |
| JP2006516250A (ja) | 2002-12-18 | 2006-06-29 | サイトビア インコーポレイティッド | カスパーゼ活性化剤およびアポトーシス誘導物質としての３，５−二置換−［１，２，４］−オキサジアゾールおよびそれらの誘導体ならびにそれらの使用 |
| RU2006100301A (ru) | 2003-06-11 | 2006-07-10 | Санкио Компани Лимитед (JP) | Соединение циклического третичного амина |
| CA2551867C (en) | 2003-12-31 | 2010-08-17 | Schering-Plough Ltd. | Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives |
| JP2008504294A (ja) * | 2004-06-25 | 2008-02-14 | アムジエン・インコーポレーテツド | サイトカイン介在疾患および他の疾患の治療において有用な縮合トリアゾールおよびインダゾール |
| US20060064650A1 (en) * | 2004-09-20 | 2006-03-23 | International Business Machines Corporation | Method, system, and computer program product for type-based table navigation |
| KR20070057965A (ko) * | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| JPWO2006070943A1 (ja) * | 2004-12-28 | 2008-06-12 | 武田薬品工業株式会社 | 縮合イミダゾール化合物およびその用途 |
| US20090163476A1 (en) * | 2005-03-03 | 2009-06-25 | Sirtris Pharmaceuticals, Inc. | N-Phenyl Benzamide Derivatives as Sirtuin Modulators |
| US7345178B2 (en) * | 2005-08-04 | 2008-03-18 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| DE102005042742A1 (de) * | 2005-09-02 | 2007-03-08 | Schering Ag | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| WO2007034278A2 (en) | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Fused imidazole derivatives as c3a receptor antagonists |
| AU2006311786A1 (en) * | 2005-11-04 | 2007-05-18 | Merck Sharp & Dohme Corp. | Diphenylmethane derivatives as inhibitors of leukotriene biosynthesis |
| DE102006011574A1 (de) * | 2006-03-10 | 2007-10-31 | Grünenthal GmbH | Substituierte Imidazo[2,1-b]thiazol-Verbindungen und ihre Verwendung zur Herstellung von Arzneimitteln |
| EP1845098A1 (en) * | 2006-03-29 | 2007-10-17 | Ferrer Internacional, S.A. | Imidazo[1,2-b]pyridazines, their processes of preparation and their use as GABA receptor ligands |
| WO2007123892A2 (en) * | 2006-04-17 | 2007-11-01 | Arqule Inc. | Raf inhibitors and their uses |
| US20080015193A1 (en) | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| EP1964841A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]azine and their use as pharmaceuticals |
| CA2707360A1 (en) * | 2007-06-20 | 2008-12-24 | Merck Sharp & Dohme Corp. | Diphenyl substituted alkanes |
| FR2918061B1 (fr) * | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| FR2918986B1 (fr) * | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| CA2695251C (en) * | 2007-08-14 | 2016-06-21 | Bayer Schering Pharma Aktiengesellschaft | Fused imidazoles for cancer treatment |
| EP2083009A1 (de) * | 2008-01-22 | 2009-07-29 | Grünenthal GmbH | Substituierte Tethrahydroimidazopyridin-Verbindungen und deren Verwendung in Arzneimitteln |
| CA2722418C (en) | 2008-05-13 | 2013-09-17 | Irm Llc | Fused nitrogen containing heterocycles and compositions thereof as kinase inhibitors |
| PA8854101A1 (es) * | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
-
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 AU AU2008318491A patent/AU2008318491B2/en not_active Ceased
- 2008-10-31 WO PCT/US2008/082027 patent/WO2009059162A1/en not_active Ceased
- 2008-10-31 MY MYPI20101943 patent/MY153065A/en unknown
- 2008-10-31 KR KR1020107011579A patent/KR20100101581A/ko not_active Abandoned
- 2008-10-31 RU RU2010122333/04A patent/RU2485113C2/ru not_active IP Right Cessation
- 2008-10-31 MX MX2010004774A patent/MX2010004774A/es active IP Right Grant
- 2008-10-31 EP EP08843535.9A patent/EP2214669B1/en not_active Not-in-force
- 2008-10-31 JP JP2010532289A patent/JP5733982B2/ja not_active Expired - Fee Related
- 2008-10-31 CA CA2704431A patent/CA2704431A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2010122333A (ru) | Ингибиторы цитокинов | |
| JP5091944B2 (ja) | イミダゾ［１，２−ｂ］ピリダジン、その調製方法及びＧＡＢＡ受容体リガンドとしてのその使用 | |
| JP4572832B2 (ja) | キナゾリンジオン骨格を有するフェニルアラニン誘導体の製造方法及び製造中間体 | |
| JP5582634B2 (ja) | ４−置換フェノキシフェニル酢酸誘導体 | |
| US7365211B2 (en) | Heterocyclic GABAA subtype selective receptor modulators | |
| WO2005042537A1 (en) | Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors | |
| JP2006525359A5 (enExample) | ||
| HRP20100670T1 (hr) | Aril-supstituirani pirazol-amid spojevi korisni kao inhibitori kinaze | |
| JP2012521406A5 (enExample) | ||
| KR20110031318A (ko) | Ｉａ 심부전 및 암 치료에 유용한 단백질 키나제 ｄ 억제제로서의 2,4'-비피리디닐 화합물 | |
| JPWO2000004014A1 (ja) | 抗腫瘍活性を有するピリミジン誘導体 | |
| JP2019523772A (ja) | キラルピロロピリミジン化合物の製造方法 | |
| CA2585315A1 (en) | Imidazo[1,2-a]pyridine compounds, compositions, uses and methods related thereto | |
| CN1458933A (zh) | 噻吩并嘧啶化合物及其盐以及其制备方法 | |
| JP2006524687A (ja) | バニロイド受容体で阻害活性を示す新規複素環アミド | |
| JP2012527487A5 (enExample) | ||
| JP6864124B2 (ja) | キナーゼ阻害剤としてのピロロトリアジン誘導体 | |
| JP2007506744A5 (enExample) | ||
| CN102617578A (zh) | 一种咪唑衍生物及其医药用途 | |
| JP2011509288A5 (enExample) | ||
| RU2364595C2 (ru) | Производные пиридоиндолона, замещенные в положении 6, их получение и применение в терапии | |
| CN103288761B (zh) | 一种合成1，2，3，4‑喹唑啉‑2，4‑二酮衍生物的新方法 | |
| JP2025533275A (ja) | Ｙａｐ－ｔｅａｄ相互作用を阻害するための新規なヘテロ二環式化合物及びそれを含む薬学的組成物 | |
| TH65856A (th) | สารประกอบเคมี |