CA2663091A1

CA2663091A1 - Modulators of interleukin-1 receptor-associated kinase

Modulators of interleukin-1 receptor-associated kinase Download PDF

Info

Publication number: CA2663091A1
Authority: CA; Canada
Prior art keywords: imidazo; pyridazin; tetrahydro; pyran; amine
Prior art date: 2006-09-07
Legal status : Abandoned

Application number

CA002663091A

Other languages

English (en)

French (fr)

Inventor

Thomas Durand-Reville

Charles Jewell

Charles Hammond

Donovan Chin

Current Assignee

Biogen MA Inc

Original Assignee

Individual

Priority date

2006-09-07

Filing date

2007-09-07

Publication date

2008-03-13

2007-09-07 Application filed by Individual filed Critical Individual

2008-03-13 Publication of CA2663091A1 publication Critical patent/CA2663091A1/en

Status Abandoned legal-status Critical Current

Links

108010072621 Interleukin-1 Receptor-Associated Kinases Proteins 0.000 title description 29
102000006940 Interleukin-1 Receptor-Associated Kinases Human genes 0.000 title description 29
238000000034 method Methods 0.000 claims abstract description 79
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims abstract description 12
101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims abstract description 11
230000001404 mediated effect Effects 0.000 claims abstract description 11
201000004681 Psoriasis Diseases 0.000 claims abstract description 9
208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 7
206010040047 Sepsis Diseases 0.000 claims abstract description 7
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 7
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 5
208000035690 Familial cold urticaria Diseases 0.000 claims abstract description 5
208000001132 Osteoporosis Diseases 0.000 claims abstract description 5
208000018737 Parkinson disease Diseases 0.000 claims abstract description 5
208000006011 Stroke Diseases 0.000 claims abstract description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 5
230000000747 cardiac effect Effects 0.000 claims abstract description 5
230000009091 contractile dysfunction Effects 0.000 claims abstract description 5
208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims abstract description 5
206010064570 familial cold autoinflammatory syndrome Diseases 0.000 claims abstract description 5
206010028417 myasthenia gravis Diseases 0.000 claims abstract description 5
208000035143 Bacterial infection Diseases 0.000 claims abstract description 4
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 4
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 4
-1 amino, hydroxy Chemical group 0.000 claims description 140
150000001875 compounds Chemical class 0.000 claims description 99
125000001072 heteroaryl group Chemical group 0.000 claims description 83
125000000217 alkyl group Chemical group 0.000 claims description 69
125000001931 aliphatic group Chemical group 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
125000003368 amide group Chemical group 0.000 claims description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
229940124530 sulfonamide Drugs 0.000 claims description 23
150000003456 sulfonamides Chemical group 0.000 claims description 23
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000000304 alkynyl group Chemical group 0.000 claims description 15
125000001188 haloalkyl 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 15
DCLWNTIANRACSB-UHFFFAOYSA-N imidazo[1,2-b]pyridazin-6-amine Chemical compound N1=C(N)C=CC2=NC=CN21 DCLWNTIANRACSB-UHFFFAOYSA-N 0.000 claims description 13
125000003107 substituted aryl group Chemical group 0.000 claims description 13
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
230000004913 activation Effects 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000001041 indolyl group Chemical group 0.000 claims description 5
230000002062 proliferating effect Effects 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
230000003247 decreasing effect Effects 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
230000004968 inflammatory condition Effects 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
DTUZIVBPPQTBFT-UHFFFAOYSA-N 1-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 DTUZIVBPPQTBFT-UHFFFAOYSA-N 0.000 claims description 3
FCPWNKFKADKUNF-UHFFFAOYSA-N 3-(2-methoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FCPWNKFKADKUNF-UHFFFAOYSA-N 0.000 claims description 3
QPAUPGQSDSAKRY-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QPAUPGQSDSAKRY-UHFFFAOYSA-N 0.000 claims description 3
YCUVASRIOGXHJP-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(OC1CCOCC1)C=C2 YCUVASRIOGXHJP-UHFFFAOYSA-N 0.000 claims description 3
QDEOYNAMUXJSHH-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QDEOYNAMUXJSHH-UHFFFAOYSA-N 0.000 claims description 3
SCRDFEJZOXJJSM-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 SCRDFEJZOXJJSM-UHFFFAOYSA-N 0.000 claims description 3
DSJKOTOWSRIEDU-UHFFFAOYSA-N 3-bromo-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazine Chemical compound N=1N2C(Br)=CN=C2C=CC=1OC1CCOCC1 DSJKOTOWSRIEDU-UHFFFAOYSA-N 0.000 claims description 3
DOPWTFXGWBIPOO-UHFFFAOYSA-N 3-bromo-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(Br)=CN=C2C=CC=1NC1CCOCC1 DOPWTFXGWBIPOO-UHFFFAOYSA-N 0.000 claims description 3
XGUDHBANBOEOLA-UHFFFAOYSA-N 4-[2-amino-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound N=1N2C(C=3C=CC(=CC=3)C#N)=C(N)N=C2C=CC=1OC1CCOCC1 XGUDHBANBOEOLA-UHFFFAOYSA-N 0.000 claims description 3
UECXWGDWYUHPFD-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]morpholine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(N1CCOCC1)C=C2 UECXWGDWYUHPFD-UHFFFAOYSA-N 0.000 claims description 3
KGDVXQORBWBIHS-UHFFFAOYSA-N 4-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 KGDVXQORBWBIHS-UHFFFAOYSA-N 0.000 claims description 3
KOXVNSVKNGZIHN-UHFFFAOYSA-N 4-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=C(O)C=C1 KOXVNSVKNGZIHN-UHFFFAOYSA-N 0.000 claims description 3
OPKXXSDVMPBIOF-UHFFFAOYSA-N 4-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 OPKXXSDVMPBIOF-UHFFFAOYSA-N 0.000 claims description 3
PHLHEYALRJOPMB-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 PHLHEYALRJOPMB-UHFFFAOYSA-N 0.000 claims description 3
DFYXVCWJEDZGPJ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DFYXVCWJEDZGPJ-UHFFFAOYSA-N 0.000 claims description 3
BWBYBKHRQMCAAS-VOTSOKGWSA-N n-(oxan-4-yl)-3-[(e)-2-phenylethenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(\C=C\C=3C=CC=CC=3)=CN=C2C=C1 BWBYBKHRQMCAAS-VOTSOKGWSA-N 0.000 claims description 3
WXHHSNLRMCAIPE-UHFFFAOYSA-N n-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 WXHHSNLRMCAIPE-UHFFFAOYSA-N 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
QENZCKMDMMAVLU-VMPITWQZSA-N (e)-3-[3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(\C=C\C(O)=O)=C1 QENZCKMDMMAVLU-VMPITWQZSA-N 0.000 claims description 2
LIWNRPDZCPMYLF-VMPITWQZSA-N (e)-3-[3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(\C=C\C(O)=O)=C1 LIWNRPDZCPMYLF-VMPITWQZSA-N 0.000 claims description 2
SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical group C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims description 2
BVFGOCCZLAFACJ-UHFFFAOYSA-N 1-[3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(C(C)=O)=C1 BVFGOCCZLAFACJ-UHFFFAOYSA-N 0.000 claims description 2
VLONLXDVIRSEGY-UHFFFAOYSA-N 2-[[3-(2-methoxy-5-propan-2-ylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C2N1N=C(NC(CO)C(C)C)C=C2 VLONLXDVIRSEGY-UHFFFAOYSA-N 0.000 claims description 2
DIGMAWDYOFWXAX-UHFFFAOYSA-N 2-methoxy-4-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(O)C(OC)=C1 DIGMAWDYOFWXAX-UHFFFAOYSA-N 0.000 claims description 2
GNSKGHQQFNMVSH-UHFFFAOYSA-N 2-methoxy-4-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(O)C(OC)=C1 GNSKGHQQFNMVSH-UHFFFAOYSA-N 0.000 claims description 2
IWUQKHWRRPDIRW-UHFFFAOYSA-N 2-methoxy-4-[6-[(3,4,5-trimethoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=C(OC)C(OC)=C(OC)C=4)C=CC3=NC=2)=C1 IWUQKHWRRPDIRW-UHFFFAOYSA-N 0.000 claims description 2
XEFUVQWKJMWQCK-UHFFFAOYSA-N 2-methoxy-4-[6-[(4-methoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1CNC1=NN2C(C=3C=C(OC)C(O)=CC=3)=CN=C2C=C1 XEFUVQWKJMWQCK-UHFFFAOYSA-N 0.000 claims description 2
GCUWCTVRJNUNSB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C2OCOC2=CC=C1C(N1N=2)=CN=C1C=CC=2NC1CCOCC1 GCUWCTVRJNUNSB-UHFFFAOYSA-N 0.000 claims description 2
VLXSAZOORSAKQP-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-n-[(3-chlorophenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(CNC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)=C1 VLXSAZOORSAKQP-UHFFFAOYSA-N 0.000 claims description 2
LRMRSZOYWDATQW-UHFFFAOYSA-N 3-(2-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 LRMRSZOYWDATQW-UHFFFAOYSA-N 0.000 claims description 2
FARMWKAMFJACDP-UHFFFAOYSA-N 3-(2-methoxy-5-propan-2-ylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FARMWKAMFJACDP-UHFFFAOYSA-N 0.000 claims description 2
ZJAHXEWFCQDCLN-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(furan-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 ZJAHXEWFCQDCLN-UHFFFAOYSA-N 0.000 claims description 2
YVHJWFQOFXIJQJ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC(OC)=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 YVHJWFQOFXIJQJ-UHFFFAOYSA-N 0.000 claims description 2
NRYQFUGOLUZWBC-UHFFFAOYSA-N 3-(3-aminophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound NC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 NRYQFUGOLUZWBC-UHFFFAOYSA-N 0.000 claims description 2
UUAFYGWPFDIGGG-UHFFFAOYSA-N 3-(3-bromophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound BrC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 UUAFYGWPFDIGGG-UHFFFAOYSA-N 0.000 claims description 2
KDKPZLXEJWBWSB-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 KDKPZLXEJWBWSB-UHFFFAOYSA-N 0.000 claims description 2
OEIWNDGDGDPXIO-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 OEIWNDGDGDPXIO-UHFFFAOYSA-N 0.000 claims description 2
VEEVIGPGXRUMAH-UHFFFAOYSA-N 3-(3-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 VEEVIGPGXRUMAH-UHFFFAOYSA-N 0.000 claims description 2
OKVDAAHGLLLMQQ-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 OKVDAAHGLLLMQQ-UHFFFAOYSA-N 0.000 claims description 2
UVSIZRLYKSOJEB-UHFFFAOYSA-N 3-(4-aminophenyl)-n-[(4-methoxyphenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NN2C(C=3C=CC(N)=CC=3)=CN=C2C=C1 UVSIZRLYKSOJEB-UHFFFAOYSA-N 0.000 claims description 2
PJPADMCOSXJIKA-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(Cl)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 PJPADMCOSXJIKA-UHFFFAOYSA-N 0.000 claims description 2
ABXCRGPSYQVOOK-UHFFFAOYSA-N 3-(4-methylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 ABXCRGPSYQVOOK-UHFFFAOYSA-N 0.000 claims description 2
VOWVFBKLQUGYAM-UHFFFAOYSA-N 3-(furan-3-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C3=COC=C3)=CN=C2C=C1 VOWVFBKLQUGYAM-UHFFFAOYSA-N 0.000 claims description 2
BBUCGVBTCXYNGZ-RMKNXTFCSA-N 3-[3-[(e)-hex-1-enyl]phenyl]-n-(3-methoxypropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CCCC\C=C\C1=CC=CC(C=2N3N=C(NCCCOC)C=CC3=NC=2)=C1 BBUCGVBTCXYNGZ-RMKNXTFCSA-N 0.000 claims description 2
URFUREUXEJUAMW-UHFFFAOYSA-N 3-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 URFUREUXEJUAMW-UHFFFAOYSA-N 0.000 claims description 2
CARBPBGHMOMKDJ-UHFFFAOYSA-N 3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(C=O)=C1 CARBPBGHMOMKDJ-UHFFFAOYSA-N 0.000 claims description 2
FHGILYMGRBCAAZ-UHFFFAOYSA-N 3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 FHGILYMGRBCAAZ-UHFFFAOYSA-N 0.000 claims description 2
KVVCRCBDCMZVOD-UHFFFAOYSA-N 3-[6-[[4-(4-methylpiperazin-1-yl)phenyl]methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CNC1=NN2C(C=3C=C(O)C=CC=3)=CN=C2C=C1 KVVCRCBDCMZVOD-UHFFFAOYSA-N 0.000 claims description 2
GLBSLIRMQICJQL-UHFFFAOYSA-N 3-[[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=C2OCOC2=CC(C2=CN=C3C=CC(=NN32)NCCCO)=C1 GLBSLIRMQICJQL-UHFFFAOYSA-N 0.000 claims description 2
RXPXYZYROMKRFK-UHFFFAOYSA-N 3-[[3-(1-benzylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C(=C1)C=NN1CC1=CC=CC=C1 RXPXYZYROMKRFK-UHFFFAOYSA-N 0.000 claims description 2
ZCSKKCCORPSIBO-UHFFFAOYSA-N 3-[[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NCCCO)C=C2 ZCSKKCCORPSIBO-UHFFFAOYSA-N 0.000 claims description 2
JEWKQEMLDSNXFP-UHFFFAOYSA-N 3-[[3-[3-(dimethylamino)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 JEWKQEMLDSNXFP-UHFFFAOYSA-N 0.000 claims description 2
IEHKSBYALGYZHJ-UHFFFAOYSA-N 3-naphthalen-1-yl-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C4=CC=CC=C4C=CC=3)=CN=C2C=C1 IEHKSBYALGYZHJ-UHFFFAOYSA-N 0.000 claims description 2
ZNIXBGSPJBGFNO-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCCC1=CC=CN=C1 ZNIXBGSPJBGFNO-UHFFFAOYSA-N 0.000 claims description 2
FEJZJBDPYBAZQL-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCC1=CC=NC=C1 FEJZJBDPYBAZQL-UHFFFAOYSA-N 0.000 claims description 2
VKCMABZJYYEOAV-UHFFFAOYSA-N 4-[6-(1,3-benzodioxol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=C5OCOC5=CC=4)C=CC3=NC=2)=C1 VKCMABZJYYEOAV-UHFFFAOYSA-N 0.000 claims description 2
UCMSBUNRQQQJDL-UHFFFAOYSA-N 4-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 UCMSBUNRQQQJDL-UHFFFAOYSA-N 0.000 claims description 2
HZVMMGBOKNTJGO-UHFFFAOYSA-N 4-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NCC=1SC=CC=1)C=C2 HZVMMGBOKNTJGO-UHFFFAOYSA-N 0.000 claims description 2
RHOHRUFMSMBKCM-UHFFFAOYSA-N 4-[6-[(2,4-dimethylphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C(=CC(C)=CC=4)C)C=CC3=NC=2)=C1 RHOHRUFMSMBKCM-UHFFFAOYSA-N 0.000 claims description 2
LIQTYZBALHBKHL-UHFFFAOYSA-N 4-[6-[(3,4-dichlorophenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=C(Cl)C(Cl)=CC=4)C=CC3=NC=2)=C1 LIQTYZBALHBKHL-UHFFFAOYSA-N 0.000 claims description 2
YEVOKDCYAMXGAP-UHFFFAOYSA-N 4-[6-[(3-chlorophenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=C(Cl)C=CC=4)C=CC3=NC=2)=C1 YEVOKDCYAMXGAP-UHFFFAOYSA-N 0.000 claims description 2
SVCACGYSWHZISY-UHFFFAOYSA-N 4-[6-[(3-chlorophenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CN=C2N1N=C(NCC=1C=C(Cl)C=CC=1)C=C2 SVCACGYSWHZISY-UHFFFAOYSA-N 0.000 claims description 2
VGQJYVBYSJWDCF-UHFFFAOYSA-N 4-[6-[(3-chlorophenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NCC=1C=C(Cl)C=CC=1)C=C2 VGQJYVBYSJWDCF-UHFFFAOYSA-N 0.000 claims description 2
FKCNTNLOFNANIQ-UHFFFAOYSA-N 4-[6-[(4-methoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1CNC1=NN2C(C=3C=CC(O)=CC=3)=CN=C2C=C1 FKCNTNLOFNANIQ-UHFFFAOYSA-N 0.000 claims description 2
ZYMOFWHXOIPXLE-ZDUSSCGKSA-N 4-[6-[[(2R)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(N[C@@H](CO)C(C)C)C=CC3=NC=2)=C1 ZYMOFWHXOIPXLE-ZDUSSCGKSA-N 0.000 claims description 2
AABZMMRIPCBZPK-UHFFFAOYSA-N 4-[[[3-(1-benzylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C3=CN(CC=4C=CC=CC=4)N=C3)=CN=C2C=C1 AABZMMRIPCBZPK-UHFFFAOYSA-N 0.000 claims description 2
UPFVAHVWLNBVSG-UHFFFAOYSA-N 4-[[[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(=CC=1)S(N)(=O)=O)C=C2 UPFVAHVWLNBVSG-UHFFFAOYSA-N 0.000 claims description 2
PFZAUIXGTSABGQ-UHFFFAOYSA-N 4-[[[3-(3-formylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=C(C=O)C=CC=3)=CN=C2C=C1 PFZAUIXGTSABGQ-UHFFFAOYSA-N 0.000 claims description 2
LLKMNTREBZDNKG-UHFFFAOYSA-N 4-[[[3-(4-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=CC(O)=CC=3)=CN=C2C=C1 LLKMNTREBZDNKG-UHFFFAOYSA-N 0.000 claims description 2
KNPCDSZXZHMZNO-UHFFFAOYSA-N 4-[[[3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(=CC=1)S(N)(=O)=O)C=C2 KNPCDSZXZHMZNO-UHFFFAOYSA-N 0.000 claims description 2
BPYJCLPGCMOGDV-UHFFFAOYSA-N 4-[[[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=CC(CO)=CC=3)=CN=C2C=C1 BPYJCLPGCMOGDV-UHFFFAOYSA-N 0.000 claims description 2
DPACXQFXKZQREE-UHFFFAOYSA-N [2-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound OCC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DPACXQFXKZQREE-UHFFFAOYSA-N 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
IAFJBBRUTHQHRQ-UHFFFAOYSA-N chembl1952328 Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(F)=CC=1)C=C2 IAFJBBRUTHQHRQ-UHFFFAOYSA-N 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
208000026278 immune system disease Diseases 0.000 claims description 2
IGNHCIWPYDCHMS-UHFFFAOYSA-N methyl 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 IGNHCIWPYDCHMS-UHFFFAOYSA-N 0.000 claims description 2
SCLOVPWSNGCKDT-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CN=CC(C=2N3N=C(NCC=4C=C5OCOC5=CC=4)C=CC3=NC=2)=C1 SCLOVPWSNGCKDT-UHFFFAOYSA-N 0.000 claims description 2
YOJRRLVGMNHOBB-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-3-pyridin-4-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(=NN12)C=CC1=NC=C2C1=CC=NC=C1 YOJRRLVGMNHOBB-UHFFFAOYSA-N 0.000 claims description 2
KCBCUSRFTUZZOQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound OCCNC(=O)C1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 KCBCUSRFTUZZOQ-UHFFFAOYSA-N 0.000 claims description 2
IDJFXVWEUPZZPZ-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(4-morpholin-4-ylphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C(C=C1)=CC=C1N1CCOCC1 IDJFXVWEUPZZPZ-UHFFFAOYSA-N 0.000 claims description 2
DXEOQBVUPWWNMC-UHFFFAOYSA-N n-(2-methoxyethyl)-3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC=CC2=CC(C3=CN=C4C=CC(=NN43)NCCOC)=CC=C21 DXEOQBVUPWWNMC-UHFFFAOYSA-N 0.000 claims description 2
NQTYGUCGIXQGLU-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCCCN1CCOCC1 NQTYGUCGIXQGLU-UHFFFAOYSA-N 0.000 claims description 2
VIVCYKIMBXLUQO-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)C=C1 VIVCYKIMBXLUQO-UHFFFAOYSA-N 0.000 claims description 2
GAVUFIABJUEMTM-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(2-methoxy-5-propan-2-ylphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 GAVUFIABJUEMTM-UHFFFAOYSA-N 0.000 claims description 2
SGTKFSGXLBBJGF-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 SGTKFSGXLBBJGF-UHFFFAOYSA-N 0.000 claims description 2
QHOZELDQVQUFQE-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(4-phenoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=COC=1CNC(=NN12)C=CC1=NC=C2C(C=C1)=CC=C1OC1=CC=CC=C1 QHOZELDQVQUFQE-UHFFFAOYSA-N 0.000 claims description 2
KTNNNXYFQXUWNE-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-[4-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 KTNNNXYFQXUWNE-UHFFFAOYSA-N 0.000 claims description 2
MNAWNZNIDLFICD-UHFFFAOYSA-N n-(oxan-4-yl)-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC(F)(F)OC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 MNAWNZNIDLFICD-UHFFFAOYSA-N 0.000 claims description 2
LAFDCOYNCUJOKA-UHFFFAOYSA-N n-(oxan-4-yl)-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=CC=CC=3)=CN=C2C=C1 LAFDCOYNCUJOKA-UHFFFAOYSA-N 0.000 claims description 2
CFHHVNDJQFVAPI-UHFFFAOYSA-N n-(oxan-4-yl)-3-pyrimidin-5-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=NC=NC=3)=CN=C2C=C1 CFHHVNDJQFVAPI-UHFFFAOYSA-N 0.000 claims description 2
XKJLRESMJACVSY-UHFFFAOYSA-N n-(oxan-4-yl)-3-thiophen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3SC=CC=3)=CN=C2C=C1 XKJLRESMJACVSY-UHFFFAOYSA-N 0.000 claims description 2
ZQFYZJCWLCVGOZ-UHFFFAOYSA-N n-[3-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 ZQFYZJCWLCVGOZ-UHFFFAOYSA-N 0.000 claims description 2
VKMXUJUJBPXGEB-INIZCTEOSA-N n-[3-[6-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide Chemical compound N12N=C(N[C@@H](CO)C(C)C)C=CC2=NC=C1C1=CC=CC(NC(C)=O)=C1 VKMXUJUJBPXGEB-INIZCTEOSA-N 0.000 claims description 2
KNAGKDNDPXPXJV-UHFFFAOYSA-N n-[3-bromo-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-2-yl]-2,2,2-trifluoroacetamide Chemical compound N=1N2C(Br)=C(NC(=O)C(F)(F)F)N=C2C=CC=1OC1CCOCC1 KNAGKDNDPXPXJV-UHFFFAOYSA-N 0.000 claims description 2
KZFDCZRBONTTAL-UHFFFAOYSA-N n-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]-3-[4-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CNC1=NN2C(C=3C=CC(OC(F)(F)F)=CC=3)=CN=C2C=C1 KZFDCZRBONTTAL-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 10
JSBGWDNSENOORN-UHFFFAOYSA-N 2-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 JSBGWDNSENOORN-UHFFFAOYSA-N 0.000 claims 2
SPSXRVIHUDPXQZ-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 SPSXRVIHUDPXQZ-UHFFFAOYSA-N 0.000 claims 2
ZYMOFWHXOIPXLE-CYBMUJFWSA-N 4-[6-[[(2S)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(N[C@H](CO)C(C)C)C=CC3=NC=2)=C1 ZYMOFWHXOIPXLE-CYBMUJFWSA-N 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
CASKVJFIBGKPRI-CQSZACIVSA-N (2s)-2-[[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(F)C=C1 CASKVJFIBGKPRI-CQSZACIVSA-N 0.000 claims 1
DQESXLDSAYDERW-INIZCTEOSA-N (2s)-2-amino-3-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](N)C(O)=O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DQESXLDSAYDERW-INIZCTEOSA-N 0.000 claims 1
URSYIWDQINHOHD-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 URSYIWDQINHOHD-UHFFFAOYSA-N 0.000 claims 1
NDKBCWRJIHKEQO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)C=C1 NDKBCWRJIHKEQO-UHFFFAOYSA-N 0.000 claims 1
VOYNWNNIMHGMDV-SNAWJCMRSA-N (e)-3-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 VOYNWNNIMHGMDV-SNAWJCMRSA-N 0.000 claims 1
FVEFSYLRXMQDTA-QPJJXVBHSA-N (e)-3-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 FVEFSYLRXMQDTA-QPJJXVBHSA-N 0.000 claims 1
NFFHTTGHKAWIHJ-UHFFFAOYSA-N 1-[3-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]-2-hydroxyethanone Chemical compound OCC(=O)C1=CC=CC(C=2N3N=C(NC4CCCCC4)C=CC3=NC=2)=C1 NFFHTTGHKAWIHJ-UHFFFAOYSA-N 0.000 claims 1
YVFKGXUGCTVDRW-UHFFFAOYSA-N 1-[5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 YVFKGXUGCTVDRW-UHFFFAOYSA-N 0.000 claims 1
QQJXVOYLYGFWKD-GFCCVEGCSA-N 1-[5-[6-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]thiophen-2-yl]ethanone Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(C(C)=O)S1 QQJXVOYLYGFWKD-GFCCVEGCSA-N 0.000 claims 1
BUCQEBGZOUHFNE-UHFFFAOYSA-N 2-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BUCQEBGZOUHFNE-UHFFFAOYSA-N 0.000 claims 1
OGCPTBHWWATXSG-UHFFFAOYSA-N 2-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 OGCPTBHWWATXSG-UHFFFAOYSA-N 0.000 claims 1
AMCQSNFXZVJXAV-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound N12N=C(NCCO)C=CC2=NC=C1C1=CC=C(F)C=C1 AMCQSNFXZVJXAV-UHFFFAOYSA-N 0.000 claims 1
ANAWTLNXCZEKNV-UHFFFAOYSA-N 2-fluoro-4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzohydrazide Chemical compound C1=C(F)C(C(=O)NN)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 ANAWTLNXCZEKNV-UHFFFAOYSA-N 0.000 claims 1
SVTUXDXGOZWCSF-UHFFFAOYSA-N 2-fluoro-5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C1=C(C=O)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 SVTUXDXGOZWCSF-UHFFFAOYSA-N 0.000 claims 1
BBMZBUUWXLYGPM-UHFFFAOYSA-N 2-fluoro-5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BBMZBUUWXLYGPM-UHFFFAOYSA-N 0.000 claims 1
UHOCSXUVXQGFLS-UHFFFAOYSA-N 2-hydroxy-1-[3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(C(=O)CO)=C1 UHOCSXUVXQGFLS-UHFFFAOYSA-N 0.000 claims 1
GNKFLYCZFHBCNW-UHFFFAOYSA-N 2-hydroxy-1-[3-[6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound OCC(=O)C1=CC=CC(C=2N3N=C(OC4CCOCC4)C=CC3=NC=2)=C1 GNKFLYCZFHBCNW-UHFFFAOYSA-N 0.000 claims 1
YTUUHCQHXXCOPL-UHFFFAOYSA-N 2-methoxy-4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 YTUUHCQHXXCOPL-UHFFFAOYSA-N 0.000 claims 1
WDROEHWYJIEEFT-UHFFFAOYSA-N 2-methoxy-4-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 WDROEHWYJIEEFT-UHFFFAOYSA-N 0.000 claims 1
OLSQOVJNJXIUSG-UHFFFAOYSA-N 3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound O1CCOC11CC=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)CC1 OLSQOVJNJXIUSG-UHFFFAOYSA-N 0.000 claims 1
NKOBRSDHMMNMFS-UHFFFAOYSA-N 3-(1-benzofuran-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4C=COC4=CC=3)=CN=C2C=C1 NKOBRSDHMMNMFS-UHFFFAOYSA-N 0.000 claims 1
YOHJXUCGTXNCQV-UHFFFAOYSA-N 3-(1H-indol-2-yl)-N-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3NC4=CC=CC=C4C=3)=CN=C2C=C1 YOHJXUCGTXNCQV-UHFFFAOYSA-N 0.000 claims 1
AXOCFNVMBYJDJY-UHFFFAOYSA-N 3-(1h-indazol-6-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4NN=CC4=CC=3)=CN=C2C=C1 AXOCFNVMBYJDJY-UHFFFAOYSA-N 0.000 claims 1
WOMZZJAJCKKGPF-UHFFFAOYSA-N 3-(1h-indol-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4C=CNC4=CC=3)=CN=C2C=C1 WOMZZJAJCKKGPF-UHFFFAOYSA-N 0.000 claims 1
USQPQCUNDZGGKO-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 USQPQCUNDZGGKO-UHFFFAOYSA-N 0.000 claims 1
ILUKHUPYJKDDKX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 ILUKHUPYJKDDKX-UHFFFAOYSA-N 0.000 claims 1
VRWRCLFBELGLGR-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=NC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VRWRCLFBELGLGR-UHFFFAOYSA-N 0.000 claims 1
DUDQKNTVGVLEST-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DUDQKNTVGVLEST-UHFFFAOYSA-N 0.000 claims 1
QYKIWJHPGAYFMP-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(F)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QYKIWJHPGAYFMP-UHFFFAOYSA-N 0.000 claims 1
ATLADHCNBBRFCR-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(N)=CC=C1C1=CN=C2N1N=C(NCC=1SC=CC=1)C=C2 ATLADHCNBBRFCR-UHFFFAOYSA-N 0.000 claims 1
IMSLUXLFYQRYCU-UHFFFAOYSA-N 3-(4-ethenylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C=C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 IMSLUXLFYQRYCU-UHFFFAOYSA-N 0.000 claims 1
AGYNTTUAWTZVCU-UHFFFAOYSA-N 3-(4-ethylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(CC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 AGYNTTUAWTZVCU-UHFFFAOYSA-N 0.000 claims 1
JAMWJGVLGCGLCM-UHFFFAOYSA-N 3-(4-ethynylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C#C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 JAMWJGVLGCGLCM-UHFFFAOYSA-N 0.000 claims 1
DJPZPDRTRHIQTR-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-2-amine Chemical compound N=1N2C(C=3C=CC(F)=CC=3)=C(N)N=C2C=CC=1OC1CCOCC1 DJPZPDRTRHIQTR-UHFFFAOYSA-N 0.000 claims 1
SJBNTZCXPOXRBT-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methylsulfanylimidazo[1,2-b]pyridazine Chemical compound N12N=C(SC)C=CC2=NC=C1C1=CC=C(F)C=C1 SJBNTZCXPOXRBT-UHFFFAOYSA-N 0.000 claims 1
YIYMZATWKMRVKN-UHFFFAOYSA-N 3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(N)C=CC2=NC=C1C1=CC=C(F)C=C1 YIYMZATWKMRVKN-UHFFFAOYSA-N 0.000 claims 1
FFAYOWIBYJUERY-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(SC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FFAYOWIBYJUERY-UHFFFAOYSA-N 0.000 claims 1
BWRZPNZLUQKAFO-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BWRZPNZLUQKAFO-UHFFFAOYSA-N 0.000 claims 1
VZPHCYFAFJIMHB-UHFFFAOYSA-N 3-(4-nitrophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VZPHCYFAFJIMHB-UHFFFAOYSA-N 0.000 claims 1
DBSUBKDZKKKGDZ-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DBSUBKDZKKKGDZ-UHFFFAOYSA-N 0.000 claims 1
UVVDCZSLSPCRJT-UHFFFAOYSA-N 3-(6-fluoropyridin-3-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 UVVDCZSLSPCRJT-UHFFFAOYSA-N 0.000 claims 1
ZDIDYDMLTZTJDX-UHFFFAOYSA-N 3-(furan-2-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3OC=CC=3)=CN=C2C=C1 ZDIDYDMLTZTJDX-UHFFFAOYSA-N 0.000 claims 1
RKNZBCGHDHDITL-UHFFFAOYSA-N 3-(imidazo[1,2-b]pyridazin-6-ylamino)propan-1-ol Chemical compound N1=C(NCCCO)C=CC2=NC=CN21 RKNZBCGHDHDITL-UHFFFAOYSA-N 0.000 claims 1
CAUARNPZYXSRHL-AATRIKPKSA-N 3-[(e)-hex-1-enyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(/C=C/CCCC)=CN=C2C=CC=1NC1CCOCC1 CAUARNPZYXSRHL-AATRIKPKSA-N 0.000 claims 1
URUNYLJXHQLOAC-BQYQJAHWSA-N 3-[(e)-oct-1-enyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(/C=C/CCCCCC)=CN=C2C=CC=1NC1CCOCC1 URUNYLJXHQLOAC-BQYQJAHWSA-N 0.000 claims 1
HPLGZZAOPLTJKS-UHFFFAOYSA-N 3-[3-(dimethylamino)phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 HPLGZZAOPLTJKS-UHFFFAOYSA-N 0.000 claims 1
DJIIEYOEICLZTR-UHFFFAOYSA-N 3-[3-[(2-chlorophenyl)methoxy]phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC=C1COC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 DJIIEYOEICLZTR-UHFFFAOYSA-N 0.000 claims 1
RLVMUFYKXZJKSU-FNORWQNLSA-N 3-[3-[(e)-hex-1-enyl]phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CCCC\C=C\C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 RLVMUFYKXZJKSU-FNORWQNLSA-N 0.000 claims 1
YIHPGALYZBKOLL-UHFFFAOYSA-N 3-[4-(methoxymethoxy)phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OCOC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 YIHPGALYZBKOLL-UHFFFAOYSA-N 0.000 claims 1
MCDJWPIPJJVISB-UHFFFAOYSA-N 3-[4-(morpholin-4-ylmethyl)phenyl]-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)C=CC=1CN1CCOCC1 MCDJWPIPJJVISB-UHFFFAOYSA-N 0.000 claims 1
UTQCNCMUTVIECS-UHFFFAOYSA-N 3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 UTQCNCMUTVIECS-UHFFFAOYSA-N 0.000 claims 1
JUFJEFYLUSCFGR-UHFFFAOYSA-N 3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(C(O)=O)=C1 JUFJEFYLUSCFGR-UHFFFAOYSA-N 0.000 claims 1
DEKWLUYFAFPSDT-UHFFFAOYSA-N 3-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NC4CCCCC4)C=CC3=NC=2)=C1 DEKWLUYFAFPSDT-UHFFFAOYSA-N 0.000 claims 1
CWPJMRQVTMMOPY-UHFFFAOYSA-N 3-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N3N=C(NC4CCCCC4)C=CC3=NC=2)=C1 CWPJMRQVTMMOPY-UHFFFAOYSA-N 0.000 claims 1
MDCLBNCLGKDBCC-UHFFFAOYSA-N 3-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 MDCLBNCLGKDBCC-UHFFFAOYSA-N 0.000 claims 1
GZFJCWPZFJVHJK-UHFFFAOYSA-N 3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 GZFJCWPZFJVHJK-UHFFFAOYSA-N 0.000 claims 1
DPEMYWRZZPNKEA-UHFFFAOYSA-N 3-[6-[(3,4,5-trimethoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound COC1=C(OC)C(OC)=CC(CNC2=NN3C(C=4C=C(O)C=CC=4)=CN=C3C=C2)=C1 DPEMYWRZZPNKEA-UHFFFAOYSA-N 0.000 claims 1
XRYVHEVWBSFEOK-UHFFFAOYSA-N 3-[6-[(4-hydroxycyclohexyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C(C=CC=3)C(O)=O)=CN=C2C=C1 XRYVHEVWBSFEOK-UHFFFAOYSA-N 0.000 claims 1
XSCPUVBIAKROPA-UHFFFAOYSA-N 3-[[3-(3-aminophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound NC1=CC=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 XSCPUVBIAKROPA-UHFFFAOYSA-N 0.000 claims 1
KGTGBNCUBUBSSR-UHFFFAOYSA-N 3-[[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=C(F)C=C1 KGTGBNCUBUBSSR-UHFFFAOYSA-N 0.000 claims 1
WEAOHBLPXKCASE-UHFFFAOYSA-N 3-[[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(CO)=C1 WEAOHBLPXKCASE-UHFFFAOYSA-N 0.000 claims 1
KDRFSAYDNRYPFC-UHFFFAOYSA-N 3-bromo-6-(furan-2-ylmethoxy)imidazo[1,2-b]pyridazine Chemical compound N=1N2C(Br)=CN=C2C=CC=1OCC1=CC=CO1 KDRFSAYDNRYPFC-UHFFFAOYSA-N 0.000 claims 1
GJCULIRZEXXZGM-UHFFFAOYSA-N 3-bromo-n-cyclohexylimidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(Br)=CN=C2C=CC=1NC1CCCCC1 GJCULIRZEXXZGM-UHFFFAOYSA-N 0.000 claims 1
UEJRPOSPXPYOJN-UHFFFAOYSA-N 3-ethenyl-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(C=C)=CN=C2C=CC=1NC1CCOCC1 UEJRPOSPXPYOJN-UHFFFAOYSA-N 0.000 claims 1
DNIKSAPRRKTEJA-UHFFFAOYSA-N 3-thiophen-2-yl-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CSC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CS1 DNIKSAPRRKTEJA-UHFFFAOYSA-N 0.000 claims 1
RNPABIXIOSQLOH-UHFFFAOYSA-N 4-(6-cyclohexyloxyimidazo[1,2-b]pyridazin-3-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(OC1CCCCC1)C=C2 RNPABIXIOSQLOH-UHFFFAOYSA-N 0.000 claims 1
OOJNFYFVTSSVAZ-UHFFFAOYSA-N 4-(6-cyclohexylsulfanylimidazo[1,2-b]pyridazin-3-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(SC1CCCCC1)C=C2 OOJNFYFVTSSVAZ-UHFFFAOYSA-N 0.000 claims 1
YWPRESMDEWBIIR-UHFFFAOYSA-N 4-[(3-bromoimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(Br)=CN=C2C=C1 YWPRESMDEWBIIR-UHFFFAOYSA-N 0.000 claims 1
YPXAUCODCCIHFP-UHFFFAOYSA-N 4-[2-amino-6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N=1N2C(C=3C=CC(O)=CC=3)=C(N)N=C2C=CC=1OC1CCOCC1 YPXAUCODCCIHFP-UHFFFAOYSA-N 0.000 claims 1
BKNNAPVJILMAST-UHFFFAOYSA-N 4-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]anilino]-4-oxobutanoic acid Chemical compound C1=CC(NC(=O)CCC(=O)O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BKNNAPVJILMAST-UHFFFAOYSA-N 0.000 claims 1
DJWHAISGEPYECC-UHFFFAOYSA-N 4-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(NC1CCCCC1)C=C2 DJWHAISGEPYECC-UHFFFAOYSA-N 0.000 claims 1
SDAPIJKUFXEZSO-UHFFFAOYSA-N 4-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NC1CCCCC1)C=C2 SDAPIJKUFXEZSO-UHFFFAOYSA-N 0.000 claims 1
LFOUUZURSDNKED-UHFFFAOYSA-N 4-[6-(furan-2-ylmethoxy)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(OCC=1OC=CC=1)C=C2 LFOUUZURSDNKED-UHFFFAOYSA-N 0.000 claims 1
ADGQMJXQWWJGDU-UHFFFAOYSA-N 4-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 ADGQMJXQWWJGDU-UHFFFAOYSA-N 0.000 claims 1
PTQZPNVPAMVTRJ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)C=CC=1C(=O)NC1=NN=NN1 PTQZPNVPAMVTRJ-UHFFFAOYSA-N 0.000 claims 1
NXPFHUPKORDOHQ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 NXPFHUPKORDOHQ-UHFFFAOYSA-N 0.000 claims 1
DGURBPXHUQDGBB-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DGURBPXHUQDGBB-UHFFFAOYSA-N 0.000 claims 1
PELZLXVMGWCBOW-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 PELZLXVMGWCBOW-UHFFFAOYSA-N 0.000 claims 1
JPNOBIYMAQWEQZ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 JPNOBIYMAQWEQZ-UHFFFAOYSA-N 0.000 claims 1
VSFQOCOYWPORSY-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VSFQOCOYWPORSY-UHFFFAOYSA-N 0.000 claims 1
FKUWIAWRWAQBPS-UHFFFAOYSA-N 4-[6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(OC1CCOCC1)C=C2 FKUWIAWRWAQBPS-UHFFFAOYSA-N 0.000 claims 1
MGOMQBOLVDMTAO-UHFFFAOYSA-N 4-[6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(OC1CCOCC1)C=C2 MGOMQBOLVDMTAO-UHFFFAOYSA-N 0.000 claims 1
IZFLMKAODHSONV-UHFFFAOYSA-N 4-[6-(propan-2-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NC(C)C)C=CC2=NC=C1C1=CC=C(O)C=C1 IZFLMKAODHSONV-UHFFFAOYSA-N 0.000 claims 1
QYJHJLVQFZEZEK-UHFFFAOYSA-N 4-[6-[(4-hydroxycyclohexyl)amino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=CC(O)=CC=3)=CN=C2C=C1 QYJHJLVQFZEZEK-UHFFFAOYSA-N 0.000 claims 1
NUMHLGGSJONXOR-CQSZACIVSA-N 4-[6-[[(2S)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(O)C=C1 NUMHLGGSJONXOR-CQSZACIVSA-N 0.000 claims 1
QMIBWGSSHDKJAL-OAHLLOKOSA-N 4-[6-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(C=O)C=C1 QMIBWGSSHDKJAL-OAHLLOKOSA-N 0.000 claims 1
CQZVJEKKNHOFNB-OAHLLOKOSA-N 4-[6-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(C#N)C=C1 CQZVJEKKNHOFNB-OAHLLOKOSA-N 0.000 claims 1
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