CA2704431A1 - Cytokine inhibitors - Google Patents

Info

Publication number

CA2704431A1

CA2704431A1 CA2704431A CA2704431A CA2704431A1 CA 2704431 A1 CA2704431 A1 CA 2704431A1 CA 2704431 A CA2704431 A CA 2704431A CA 2704431 A CA2704431 A CA 2704431A CA 2704431 A1 CA2704431 A1 CA 2704431A1

Authority

CA

Canada

Prior art keywords

imidazo

alkyl

phenyl

pyridazin

haloalkyl

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000004127 Cytokines Human genes 0.000 title claims abstract description 26
• 108090000695 Cytokines Proteins 0.000 title claims abstract description 26
• 239000003112 inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 112
• 238000000034 method Methods 0.000 claims abstract description 42
• 108010002352 Interleukin-1 Proteins 0.000 claims abstract description 12
• 238000012261 overproduction Methods 0.000 claims abstract description 7
• 230000001404 mediated effect Effects 0.000 claims abstract description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 110
• 125000003118 aryl group Chemical group 0.000 claims description 106
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 83
• 125000001188 haloalkyl group Chemical group 0.000 claims description 78
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 69
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 60
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 38
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 37
• -1 C1-haloalkyl Chemical group 0.000 claims description 27
• 125000003106 haloaryl group Chemical group 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 15
• 102000000589 Interleukin-1 Human genes 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 230000008878 coupling Effects 0.000 claims description 7
• 238000010168 coupling process Methods 0.000 claims description 7
• 238000005859 coupling reaction Methods 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
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 102000015696 Interleukins Human genes 0.000 claims description 5
• 108010063738 Interleukins Proteins 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 108010002350 Interleukin-2 Proteins 0.000 claims description 4
• 108090001005 Interleukin-6 Proteins 0.000 claims description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 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 description 3
• OMFIDPBDDJTFRG-UHFFFAOYSA-N 2-(3-imidazo[1,2-b]pyridazin-2-ylanilino)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1NC1=CC=CC(C=2N=C3C=CC=NN3C=2)=C1 OMFIDPBDDJTFRG-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• 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
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-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
• 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
• 230000036303 septic shock Effects 0.000 claims description 3
• 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 2
• 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 description 2
• 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 description 2
• 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 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 description 2
• 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 description 2
• 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 2
• UNXOFHHFHHJPAW-UHFFFAOYSA-N 2-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-n-(2-methoxyethyl)acetamide Chemical compound O1C(CC(=O)NCCOC)=NC(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=N1 UNXOFHHFHHJPAW-UHFFFAOYSA-N 0.000 claims description 2
• QVEDPFCEAYTMBQ-INIZCTEOSA-N 2-[3-(3-imidazo[1,2-b]pyridazin-2-ylphenyl)-1,2,4-oxadiazol-5-yl]-n-[[(2s)-oxolan-2-yl]methyl]acetamide Chemical compound N=1C(C=2C=C(C=CC=2)C=2N=C3C=CC=NN3C=2)=NOC=1CC(=O)NC[C@@H]1CCCO1 QVEDPFCEAYTMBQ-INIZCTEOSA-N 0.000 claims description 2
• 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 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
• 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 description 2
• 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 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
• 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 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
• 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 2
• 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 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
• 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 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
• 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 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
• 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 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
• ZSWASTFTCOIAQY-UHFFFAOYSA-N 3-[3-imidazo[1,2-b]pyridazin-2-yl-5-(2-methoxyethoxy)phenyl]-n-pyridin-2-yl-1,2,4-oxadiazole-5-carboxamide Chemical compound C=1C(OCCOC)=CC(C=2N=C3C=CC=NN3C=2)=CC=1C(N=1)=NOC=1C(=O)NC1=CC=CC=N1 ZSWASTFTCOIAQY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• YPVUOXZTKUDGOJ-UHFFFAOYSA-N 3-bromo-n-[[3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]methyl]benzamide Chemical compound N1=C2SC(C)=CN2C=C1C(C=1)=CC=CC=1CNC(=O)C1=CC=CC(Br)=C1 YPVUOXZTKUDGOJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 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
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