JP2010502716A - インターロイキン１受容体関連キナーゼの調節物質 - Google Patents

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Publication number

JP2010502716A

JP2010502716A JP2009527436A JP2009527436A JP2010502716A JP 2010502716 A JP2010502716 A JP 2010502716A JP 2009527436 A JP2009527436 A JP 2009527436A JP 2009527436 A JP2009527436 A JP 2009527436A JP 2010502716 A JP2010502716 A JP 2010502716A

Authority

JP

Japan

Prior art keywords

imidazo

pyridazin

pyran

tetrahydro

amine

Prior art date

2006-09-07

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.)

Pending

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• 108091000080 Phosphotransferase Proteins 0.000 title description 4
• 102000020233 phosphotransferase Human genes 0.000 title description 4
• 102000045959 Interleukin-1 Receptor-Like 1 Human genes 0.000 title 1
• 108700003107 Interleukin-1 Receptor-Like 1 Proteins 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 73
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
• 230000001404 mediated effect Effects 0.000 claims abstract description 11
• -1 amino, hydroxy Chemical group 0.000 claims description 123
• 150000001875 compounds Chemical class 0.000 claims description 92
• 125000001072 heteroaryl group Chemical group 0.000 claims description 87
• 125000001931 aliphatic group Chemical group 0.000 claims description 81
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 64
• 125000002723 alicyclic group Chemical group 0.000 claims description 62
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 125000004043 oxo group Chemical group O=* 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
• 150000001408 amides Chemical group 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 229940124530 sulfonamide Drugs 0.000 claims description 17
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 16
• 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
• 150000003456 sulfonamides Chemical class 0.000 claims description 15
• 125000002252 acyl group Chemical group 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000003107 substituted aryl group Chemical group 0.000 claims description 13
• 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 208000024891 symptom Diseases 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 7
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
• 206010040047 Sepsis Diseases 0.000 claims description 6
• 201000006417 multiple sclerosis Diseases 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 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 description 5
• 230000004913 activation Effects 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
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• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
• 230000001363 autoimmune Effects 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 206010028417 myasthenia gravis Diseases 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
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 208000001072 type 2 diabetes mellitus Diseases 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
• KVOCFEBFKVEVIQ-UHFFFAOYSA-N 3-(5-methoxypyridin-3-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CN=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 KVOCFEBFKVEVIQ-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
• 208000035143 Bacterial infection Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
• 230000000747 cardiac effect Effects 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 230000004968 inflammatory condition Effects 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 125000001624 naphthyl group Chemical group 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
• 125000000565 sulfonamide 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 compound 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
• 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 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
• SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-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
• 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 description 2
• 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 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
• VINQLCSFJYLNIB-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(C)C(C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VINQLCSFJYLNIB-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
• 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 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
• 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 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
• HOAAOCCLQHXZSY-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 HOAAOCCLQHXZSY-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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 description 2
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• 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
• KEZSAXBIZKJRJK-UHFFFAOYSA-N [4-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 KEZSAXBIZKJRJK-UHFFFAOYSA-N 0.000 claims description 2
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• 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
• HTSFBSDPNXQWJT-UHFFFAOYSA-N n-(pyridin-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=1N=CC=CC=1)C=C2 HTSFBSDPNXQWJT-UHFFFAOYSA-N 0.000 claims description 2
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• HTOYDHMBIHXFGV-UHFFFAOYSA-N n-[3-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 HTOYDHMBIHXFGV-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
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• 150000003839 salts Chemical class 0.000 claims description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 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 3
• 150000002431 hydrogen Chemical class 0.000 claims 3
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