AU2007292924A1

AU2007292924A1 - IRAK modulators for treating an inflammatory condition, cell proliferative disorder, immune disorder

IRAK modulators for treating an inflammatory condition, cell proliferative disorder, immune disorder Download PDF

Info

Publication number: AU2007292924A1
Authority: AU; Australia
Prior art keywords: imidazo; pyridazin; tetrahydro; pyran; amine
Prior art date: 2006-09-07
Legal status : Abandoned

Application number

AU2007292924A

Other languages

English (en)

Inventor

Donovan Chin

Thomas Durand-Reville

Charles Hammond

Charles Jewell

Current Assignee

Biogen MA Inc

Original Assignee

Biogen Idec Inc

Biogen Idec MA Inc

Priority date

2006-09-07

Filing date

2007-09-07

Publication date

2008-03-13

2007-09-07 Application filed by Biogen Idec Inc, Biogen Idec MA Inc filed Critical Biogen Idec Inc

2008-03-13 Publication of AU2007292924A1 publication Critical patent/AU2007292924A1/en

Status Abandoned legal-status Critical Current

Links

208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 26
208000035475 disorder Diseases 0.000 title claims description 11
230000002062 proliferating effect Effects 0.000 title claims description 6
230000004968 inflammatory condition Effects 0.000 title claims description 5
208000026278 immune system disease Diseases 0.000 title claims description 3
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150000001875 compounds Chemical class 0.000 claims description 99
125000001072 heteroaryl group Chemical group 0.000 claims description 84
238000000034 method Methods 0.000 claims description 78
125000001931 aliphatic group Chemical group 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 67
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 54
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 51
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 45
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 40
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 31
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
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125000001041 indolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
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208000024827 Alzheimer disease Diseases 0.000 claims description 4
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125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
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METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
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125000003226 pyrazolyl group Chemical group 0.000 claims description 4
LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 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
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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 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
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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
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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
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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
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
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 2
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 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
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
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
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
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
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
VANWJDXKGJURKG-UHFFFAOYSA-N 4-[[[3-[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=3)=CN=C2C=C1 VANWJDXKGJURKG-UHFFFAOYSA-N 0.000 claims description 2
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
229910052794 bromium Inorganic materials 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
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
CDCIEMRATQLIJD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-3-pyridin-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CN=C1 CDCIEMRATQLIJD-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
KPIGCYDKXHVDAY-UHFFFAOYSA-N n-(2-methoxyethyl)-3-quinolin-8-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CN=C2C(C3=CN=C4C=CC(=NN43)NCCOC)=CC=CC2=C1 KPIGCYDKXHVDAY-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
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
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
RZNLIJIWSORCTH-UHFFFAOYSA-N n-(oxan-4-yl)-3-(2-phenoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C(=CC=CC=3)OC=3C=CC=CC=3)=CN=C2C=C1 RZNLIJIWSORCTH-UHFFFAOYSA-N 0.000 claims description 2
CBTKYOQQQRPKHO-UHFFFAOYSA-N n-(oxan-4-yl)-3-pyridin-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=NC=CC=3)=CN=C2C=C1 CBTKYOQQQRPKHO-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
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 2
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
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
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
125000001475 halogen functional group Chemical group 0.000 claims 10
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 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
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
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
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
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
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 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
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 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
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
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
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
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
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
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
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 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
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
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
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