CA2620534C - Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments - Google Patents

Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments Download PDF

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Publication number: CA2620534C
Authority: CA; Canada
Prior art keywords: pyridazin; imidazo; amine; phenyl; pyridin
Prior art date: 2005-09-02
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.): Expired - Fee Related

Application number

CA2620534A

Other languages

English (en)

French (fr)

Other versions

CA2620534A1 (en

Inventor

Olaf Prien

Benjamin Bader

Ulrich Zuegel

Stuart James Ince

Christoph Huwe

Karina Schuck

Knut Eis

Ulrich Luecking

Rolf Jautelat

Judith Guenther

Manfred Husemann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Intellectual Property GmbH

Original Assignee

Bayer Intellectual Property GmbH

Priority date (The priority date 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 date listed.)

2005-09-02

Filing date

2006-09-01

Publication date

2014-05-27

2006-09-01 Application filed by Bayer Intellectual Property GmbH filed Critical Bayer Intellectual Property GmbH

2007-03-08 Publication of CA2620534A1 publication Critical patent/CA2620534A1/en

2014-05-27 Application granted granted Critical

2014-05-27 Publication of CA2620534C publication Critical patent/CA2620534C/en

Status Expired - Fee Related legal-status Critical Current

2026-09-01 Anticipated expiration legal-status Critical

Links

239000003814 drug Substances 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title abstract description 8
229940043355 kinase inhibitor Drugs 0.000 title description 5
239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 23
-1 C6-hydroxyalkyl Chemical group 0.000 claims description 141
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 130
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 114
150000001875 compounds Chemical class 0.000 claims description 108
229910052757 nitrogen Inorganic materials 0.000 claims description 93
125000001072 heteroaryl group Chemical group 0.000 claims description 91
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 87
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 79
125000003118 aryl group Chemical group 0.000 claims description 74
229910052760 oxygen Inorganic materials 0.000 claims description 70
239000001301 oxygen Substances 0.000 claims description 70
125000001424 substituent group Chemical group 0.000 claims description 69
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 65
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 62
125000004434 sulfur atom Chemical group 0.000 claims description 62
125000004093 cyano group Chemical group *C#N 0.000 claims description 61
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 56
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 54
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108091000080 Phosphotransferase Proteins 0.000 claims description 37
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
208000035475 disorder Diseases 0.000 claims description 34
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
125000004104 aryloxy group Chemical group 0.000 claims description 30
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 29
125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 21
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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
150000003254 radicals Chemical class 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 16
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
230000001413 cellular effect Effects 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 12
238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 9
125000002883 imidazolyl group Chemical group 0.000 claims description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229960001867 guaiacol Drugs 0.000 claims description 8
230000028993 immune response Effects 0.000 claims description 8
230000002018 overexpression Effects 0.000 claims description 8
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
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108090000315 Protein Kinase C Proteins 0.000 claims description 6
102000003923 Protein Kinase C Human genes 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
206010012442 Dermatitis contact Diseases 0.000 claims description 5
101100533890 Hypocrea jecorina (strain QM6a) sor3 gene Proteins 0.000 claims description 5
101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 5
102000001892 Protein Kinase C-theta Human genes 0.000 claims description 5
108010015499 Protein Kinase C-theta Proteins 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
208000010247 contact dermatitis Diseases 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
DAXFXNSXMCRQEN-UHFFFAOYSA-N pentane-1,4-diamine Chemical compound [CH2]C(N)CCCN DAXFXNSXMCRQEN-UHFFFAOYSA-N 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 4
206010012438 Dermatitis atopic Diseases 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
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125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 3
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
206010039491 Sarcoma Diseases 0.000 claims description 3
208000008383 Wilms tumor Diseases 0.000 claims description 3
206010064930 age-related macular degeneration Diseases 0.000 claims description 3
210000000481 breast Anatomy 0.000 claims description 3
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210000003734 kidney Anatomy 0.000 claims description 3
208000017169 kidney disease Diseases 0.000 claims description 3
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230000029663 wound healing Effects 0.000 claims description 3
LDISEUGXLXRHDE-UHFFFAOYSA-N 2-[(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)amino]butan-1-ol Chemical compound C1=CC=CC2=CC(C3=CN=C4C=CC(=NN43)NC(CO)CC)=CC=C21 LDISEUGXLXRHDE-UHFFFAOYSA-N 0.000 claims description 2
OJYINLHOEHUFHI-UHFFFAOYSA-N 2-[(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C=1C=CSC=1 OJYINLHOEHUFHI-UHFFFAOYSA-N 0.000 claims description 2
PEAHCNGDKIVIJO-UHFFFAOYSA-N 3-[(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)amino]propan-1-ol Chemical compound C1=CC=CC2=CC(C3=CN=C4C=CC(=NN43)NCCCO)=CC=C21 PEAHCNGDKIVIJO-UHFFFAOYSA-N 0.000 claims description 2
OTIGCPMJPAXXSD-UHFFFAOYSA-N 3-[(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C=1C=CSC=1 OTIGCPMJPAXXSD-UHFFFAOYSA-N 0.000 claims description 2
ZWIXNQYIROSKBL-UHFFFAOYSA-N 3-[[3-(1-benzothiophen-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=CC=C2SC(C3=CN=C4C=CC(=NN43)NCCCO)=CC2=C1 ZWIXNQYIROSKBL-UHFFFAOYSA-N 0.000 claims description 2
ODKLQSWHPYWNIG-UHFFFAOYSA-N 3-[[3-(4-methylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=CC(C)=CC=C1C1=CN=C2N1N=C(NCCCO)C=C2 ODKLQSWHPYWNIG-UHFFFAOYSA-N 0.000 claims description 2
GCISIEMLRABVIE-UHFFFAOYSA-N 4-[(3-naphthalen-1-ylimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C4=CC=CC=C4C=CC=3)=CN=C2C=C1 GCISIEMLRABVIE-UHFFFAOYSA-N 0.000 claims description 2
UNYCHFMACQUVHI-UHFFFAOYSA-N 4-[(3-quinolin-8-ylimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C4=NC=CC=C4C=CC=3)=CN=C2C=C1 UNYCHFMACQUVHI-UHFFFAOYSA-N 0.000 claims description 2
BOIZJFFSGKRTSZ-UHFFFAOYSA-N 4-[(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C3=CSC=C3)=CN=C2C=C1 BOIZJFFSGKRTSZ-UHFFFAOYSA-N 0.000 claims description 2
102100034111 Activin receptor type-1 Human genes 0.000 claims description 2
101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 claims description 2
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 2
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
XJZSCOXWUBDVEC-UHFFFAOYSA-N 1-[2-[(3-phenylimidazo[1,2-b]pyridazin-6-yl)amino]ethyl]imidazolidin-2-one Chemical compound O=C1NCCN1CCNC1=NN2C(C=3C=CC=CC=3)=CN=C2C=C1 XJZSCOXWUBDVEC-UHFFFAOYSA-N 0.000 claims 2
VVWWOFQLYXHYPA-UHFFFAOYSA-N 1-[2-[(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amino]ethyl]imidazolidin-2-one Chemical compound O=C1NCCN1CCNC1=NN2C(C3=CSC=C3)=CN=C2C=C1 VVWWOFQLYXHYPA-UHFFFAOYSA-N 0.000 claims 2
SZVGYUOLZRSNGU-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-n-(pyridin-3-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCC=1C=NC=CC=1)C=C2 SZVGYUOLZRSNGU-UHFFFAOYSA-N 0.000 claims 2
NWGTXUOHXUJHOW-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(3-imidazol-1-ylpropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCCN4C=NC=C4)C=CC3=NC=2)=C1 NWGTXUOHXUJHOW-UHFFFAOYSA-N 0.000 claims 2
NMVTWRRQTMBDMT-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(3-pyrrolidin-1-ylpropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCCN4CCCC4)C=CC3=NC=2)=C1 NMVTWRRQTMBDMT-UHFFFAOYSA-N 0.000 claims 2
XSQOEAIECDRXKS-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(pyridin-3-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCC=4C=NC=CC=4)C=CC3=NC=2)=C1 XSQOEAIECDRXKS-UHFFFAOYSA-N 0.000 claims 2
ALNSUOOJMGMQEK-UHFFFAOYSA-N 3-phenyl-n-(2-pyrrolidin-1-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=CC=CC=3)N2N=C1NCCN1CCCC1 ALNSUOOJMGMQEK-UHFFFAOYSA-N 0.000 claims 2
KMAXLFUVZGTGTH-UHFFFAOYSA-N 3-phenyl-n-(3-pyrrolidin-1-ylpropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1CCCN1CCCNC(=NN12)C=CC1=NC=C2C1=CC=CC=C1 KMAXLFUVZGTGTH-UHFFFAOYSA-N 0.000 claims 2
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BNBOGQXDXDPDFH-UHFFFAOYSA-N n',n'-diethyl-n-(3-phenylimidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine Chemical compound N12N=C(NCCCN(CC)CC)C=CC2=NC=C1C1=CC=CC=C1 BNBOGQXDXDPDFH-UHFFFAOYSA-N 0.000 claims 2
FJBIRNUJLBUXJY-UHFFFAOYSA-N n',n'-diethyl-n-[3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]propane-1,3-diamine Chemical compound N12N=C(NCCCN(CC)CC)C=CC2=NC=C1C=1C=NN(C)C=1 FJBIRNUJLBUXJY-UHFFFAOYSA-N 0.000 claims 2
WKXRMJUJSRZVOH-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C3=CSC=C3)N2N=C1NCCN1CCCC1 WKXRMJUJSRZVOH-UHFFFAOYSA-N 0.000 claims 2
ZVVFBLVNHFIFGA-UHFFFAOYSA-N n-(cyclohexylmethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1CCCCC1CNC(=NN12)C=CC1=NC=C2C=1C=CSC=1 ZVVFBLVNHFIFGA-UHFFFAOYSA-N 0.000 claims 2
BNASCCNUIGKIOT-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC(F)=CC=C1CNC1=NN2C(C3=CSC=C3)=CN=C2C=C1 BNASCCNUIGKIOT-UHFFFAOYSA-N 0.000 claims 2
QVESJNGPQVJSJI-UHFFFAOYSA-N n-[3-(5-methyl-1h-pyrazol-4-yl)propyl]-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound N1N=CC(CCCNC2=NN3C(C=4C=CC=CC=4)=CN=C3C=C2)=C1C QVESJNGPQVJSJI-UHFFFAOYSA-N 0.000 claims 2
UXVJBDDBPLEZAN-UHFFFAOYSA-N n-[3-(5-methyl-1h-pyrazol-4-yl)propyl]-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound N1N=CC(CCCNC2=NN3C(C4=CSC=C4)=CN=C3C=C2)=C1C UXVJBDDBPLEZAN-UHFFFAOYSA-N 0.000 claims 2
201000005112 urinary bladder cancer Diseases 0.000 claims 2
WHPHEEAJXQUJQJ-CYBMUJFWSA-N (2s)-2-[[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C2OCOC2=CC(C2=CN=C3C=CC(=NN32)N[C@H](CO)C(C)C)=C1 WHPHEEAJXQUJQJ-CYBMUJFWSA-N 0.000 claims 1
ILKNTILHNYLPMT-MRXNPFEDSA-N (2s)-2-[[3-(1h-indol-5-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C2NC=CC2=CC(C2=CN=C3C=CC(=NN32)N[C@H](CO)C(C)C)=C1 ILKNTILHNYLPMT-MRXNPFEDSA-N 0.000 claims 1
LEPBLXHGZPIKST-CQSZACIVSA-N (2s)-2-[[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(N[C@H](CO)C(C)C)C=C2 LEPBLXHGZPIKST-CQSZACIVSA-N 0.000 claims 1
GMEBQKBHVZBNJP-CQSZACIVSA-N (2s)-2-[[3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound COC1=CN=CC(C=2N3N=C(N[C@H](CO)C(C)C)C=CC3=NC=2)=C1 GMEBQKBHVZBNJP-CQSZACIVSA-N 0.000 claims 1
HSEIHTLTRSJWMR-MRXNPFEDSA-N (2s)-2-[[3-[3-(dimethylamino)phenyl]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=CC(N(C)C)=C1 HSEIHTLTRSJWMR-MRXNPFEDSA-N 0.000 claims 1
WEPYENACHWSGDO-OAHLLOKOSA-N (2s)-2-[[3-[4-(hydroxymethyl)phenyl]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(CO)C=C1 WEPYENACHWSGDO-OAHLLOKOSA-N 0.000 claims 1
PIBJGSPYDVHBLU-GOSISDBHSA-N (2s)-3-methyl-2-[(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)amino]butan-1-ol Chemical compound C1=CC=CC2=CC(C3=CN=C4C=CC(=NN43)N[C@H](CO)C(C)C)=CC=C21 PIBJGSPYDVHBLU-GOSISDBHSA-N 0.000 claims 1
KFLPIXASJGGHSF-CQSZACIVSA-N (2s)-3-methyl-2-[[3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(N[C@H](CO)C(C)C)C=CC3=NC=2)=C1 KFLPIXASJGGHSF-CQSZACIVSA-N 0.000 claims 1
AMGPRSUHOYAVDF-GFCCVEGCSA-N (2s)-3-methyl-2-[[3-(4-methylthiophen-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC(C)=CS1 AMGPRSUHOYAVDF-GFCCVEGCSA-N 0.000 claims 1
SXGSLJOUFOWILZ-CQSZACIVSA-N (2s)-3-methyl-2-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=CC(C(F)(F)F)=C1 SXGSLJOUFOWILZ-CQSZACIVSA-N 0.000 claims 1
ZCSJNABJGPHVIX-UHFFFAOYSA-N 1-[2-[[3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]ethyl]imidazolidin-2-one Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCN1C(NCC1)=O)C=C2 ZCSJNABJGPHVIX-UHFFFAOYSA-N 0.000 claims 1
KODPVMQTVNKCBF-UHFFFAOYSA-N 1-[2-[[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]ethyl]imidazolidin-2-one Chemical compound ClC1=CC=CC(C=2N3N=C(NCCN4C(NCC4)=O)C=CC3=NC=2)=C1 KODPVMQTVNKCBF-UHFFFAOYSA-N 0.000 claims 1
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 1
KIJCJRUKPXPOFP-UHFFFAOYSA-N 1-[3-[6-(2-pyridin-2-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NCCC=4N=CC=CC=4)C=CC3=NC=2)=C1 KIJCJRUKPXPOFP-UHFFFAOYSA-N 0.000 claims 1
RVQCKTSFUGBBIS-UHFFFAOYSA-N 1-[3-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=CC(C(C)=O)=C1 RVQCKTSFUGBBIS-UHFFFAOYSA-N 0.000 claims 1
BHQICZBYKDYEQZ-UHFFFAOYSA-N 1-[3-[6-(pyridin-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NCC=4C=CN=CC=4)C=CC3=NC=2)=C1 BHQICZBYKDYEQZ-UHFFFAOYSA-N 0.000 claims 1
ZESNUWZRLZNHHI-UHFFFAOYSA-N 2-[[3-(1-benzylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C(=C1)C=NN1CC1=CC=CC=C1 ZESNUWZRLZNHHI-UHFFFAOYSA-N 0.000 claims 1
PPVVQDBJUSBWHW-UHFFFAOYSA-N 2-[[3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C=1C=NN(C)C=1 PPVVQDBJUSBWHW-UHFFFAOYSA-N 0.000 claims 1
XZVUPXWMTANMKN-UHFFFAOYSA-N 2-[[3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC(OC)=C(OC)C(OC)=C1 XZVUPXWMTANMKN-UHFFFAOYSA-N 0.000 claims 1
GOBRDNQNPUHXAB-UHFFFAOYSA-N 2-[[3-(3-bromophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(Br)=C1 GOBRDNQNPUHXAB-UHFFFAOYSA-N 0.000 claims 1
KWWMCDVDRSJVAC-UHFFFAOYSA-N 2-[[3-(3-chloro-4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=C(F)C(Cl)=C1 KWWMCDVDRSJVAC-UHFFFAOYSA-N 0.000 claims 1
KAGWQDFFFLWBFD-UHFFFAOYSA-N 2-[[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(Cl)=C1 KAGWQDFFFLWBFD-UHFFFAOYSA-N 0.000 claims 1
VBYUFDCVIDMQJK-UHFFFAOYSA-N 2-[[3-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(OC)=C1 VBYUFDCVIDMQJK-UHFFFAOYSA-N 0.000 claims 1
NBAZGORSYIBPIX-UHFFFAOYSA-N 2-[[3-(3-methylsulfanylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound CSC1=CC=CC(C=2N3N=C(NCCO)C=CC3=NC=2)=C1 NBAZGORSYIBPIX-UHFFFAOYSA-N 0.000 claims 1
PEXUIXADZOCHRX-UHFFFAOYSA-N 2-[[3-(3-methylsulfonylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound CS(=O)(=O)C1=CC=CC(C=2N3N=C(NCCO)C=CC3=NC=2)=C1 PEXUIXADZOCHRX-UHFFFAOYSA-N 0.000 claims 1
PGLDXRCJCBZYCW-UHFFFAOYSA-N 2-[[3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=C(OC)C=C1 PGLDXRCJCBZYCW-UHFFFAOYSA-N 0.000 claims 1
HOQOVPSUTNTZCX-UHFFFAOYSA-N 2-[[3-(4-methylthiophen-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC(C)=CS1 HOQOVPSUTNTZCX-UHFFFAOYSA-N 0.000 claims 1
BNBONFYJAHHPBZ-UHFFFAOYSA-N 2-[[3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CN=CC(OC)=C1 BNBONFYJAHHPBZ-UHFFFAOYSA-N 0.000 claims 1
WJQSLJMRTYGSDF-UHFFFAOYSA-N 2-[[3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=C(OC)N=C1 WJQSLJMRTYGSDF-UHFFFAOYSA-N 0.000 claims 1
ADJOFGNWPUWCFS-UHFFFAOYSA-N 2-[[3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(OC(F)(F)F)=C1 ADJOFGNWPUWCFS-UHFFFAOYSA-N 0.000 claims 1
AMUFSGPBIFOSNV-UHFFFAOYSA-N 2-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(C(F)(F)F)=C1 AMUFSGPBIFOSNV-UHFFFAOYSA-N 0.000 claims 1
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 1
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 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
RGOFHQCMFAKMMU-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C2OCOC2=CC(C2=CN=C3C=CC(=NN32)NCCOC)=C1 RGOFHQCMFAKMMU-UHFFFAOYSA-N 0.000 claims 1
YGJXIQYNZMFDDT-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4OCOC4=CC=3)N2N=C1NCCC1=CC=CC=N1 YGJXIQYNZMFDDT-UHFFFAOYSA-N 0.000 claims 1
HGGAVKKGUCIKAP-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-(cyclopropylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4OCOC4=CC=3)N2N=C1NCC1CC1 HGGAVKKGUCIKAP-UHFFFAOYSA-N 0.000 claims 1
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 1
MHZZUQMAMZKQNM-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C2OCOC2=CC(C2=CN=C3C=CC(=NN32)NCCC)=C1 MHZZUQMAMZKQNM-UHFFFAOYSA-N 0.000 claims 1
ZSRHNAGHFRMYJX-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCCC1=CC=CC=N1 ZSRHNAGHFRMYJX-UHFFFAOYSA-N 0.000 claims 1
ZJJUJVIRXKYYFR-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC1=CC=CC=N1 ZJJUJVIRXKYYFR-UHFFFAOYSA-N 0.000 claims 1
AJBOLFIHFBPBBR-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC1=CC=NC=C1 AJBOLFIHFBPBBR-UHFFFAOYSA-N 0.000 claims 1
MHOFVKZDDTWKSD-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC=C2SC(C3=CN=C4C=CC(=NN43)NCCOC)=CC2=C1 MHOFVKZDDTWKSD-UHFFFAOYSA-N 0.000 claims 1
PEDRWBHQXJIROG-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3SC4=CC=CC=C4C=3)N2N=C1NCCC1=CC=CC=N1 PEDRWBHQXJIROG-UHFFFAOYSA-N 0.000 claims 1
FHTDHDFIXMDGBB-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3SC4=CC=CC=C4C=3)N2N=C1NCCC1=CC=CN=C1 FHTDHDFIXMDGBB-UHFFFAOYSA-N 0.000 claims 1
VQEGAEFFCWDYOW-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3SC4=CC=CC=C4C=3)=CN=C2C=C1 VQEGAEFFCWDYOW-UHFFFAOYSA-N 0.000 claims 1
PIPFTMPBPPFOFF-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3SC4=CC=CC=C4C=3)N2N=C1NCC1=CC=CC=N1 PIPFTMPBPPFOFF-UHFFFAOYSA-N 0.000 claims 1
RHMOFKCCGYRSLX-UHFFFAOYSA-N 3-(1-benzylpyrazol-4-yl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C(=C1)C=NN1CC1=CC=CC=C1 RHMOFKCCGYRSLX-UHFFFAOYSA-N 0.000 claims 1
ZAZZDQNLTGSQDQ-UHFFFAOYSA-N 3-(1-benzylpyrazol-4-yl)-n-(cyclopropylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1CC1CNC(=NN12)C=CC1=NC=C2C(=C1)C=NN1CC1=CC=CC=C1 ZAZZDQNLTGSQDQ-UHFFFAOYSA-N 0.000 claims 1
BBVHPRKWRQDMPS-UHFFFAOYSA-N 3-(1-benzylpyrazol-4-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)C=NN1CC1=CC=CC=C1 BBVHPRKWRQDMPS-UHFFFAOYSA-N 0.000 claims 1
OXOLKRGVBIPRNX-UHFFFAOYSA-N 3-(1-methylpyrazol-3-yl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CN1C=CC(C=2N3N=C(NCCC=4C=NC=CC=4)C=CC3=NC=2)=N1 OXOLKRGVBIPRNX-UHFFFAOYSA-N 0.000 claims 1
DGYQCUKDGTYYSH-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-n-(2-morpholin-4-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCN1CCOCC1)C=C2 DGYQCUKDGTYYSH-UHFFFAOYSA-N 0.000 claims 1
JBRDQPVTWOLEAE-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-n-(2-pyrrolidin-1-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCN1CCCC1)C=C2 JBRDQPVTWOLEAE-UHFFFAOYSA-N 0.000 claims 1
YZZNGTYCXIPPKV-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 YZZNGTYCXIPPKV-UHFFFAOYSA-N 0.000 claims 1
OYBNXYCCFOLMFL-UHFFFAOYSA-N 3-(1h-indol-5-yl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C2NC=CC2=CC(C2=CN=C3C=CC(=NN32)NCCOC)=C1 OYBNXYCCFOLMFL-UHFFFAOYSA-N 0.000 claims 1
KXJILGQIXOXJBV-UHFFFAOYSA-N 3-(2-methoxypyridin-4-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 KXJILGQIXOXJBV-UHFFFAOYSA-N 0.000 claims 1
PCAIBHSXTSTHGG-UHFFFAOYSA-N 3-(2-methoxypyridin-4-yl)-n-piperidin-4-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC(C=2N3N=C(NC4CCNCC4)C=CC3=NC=2)=C1 PCAIBHSXTSTHGG-UHFFFAOYSA-N 0.000 claims 1
UEIUWWPUONKVPN-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-[2-(3-methylpyridin-2-yl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CC=CN=C1CCNC1=NN2C(C=3C=C(Cl)C(Cl)=CC=3)=CN=C2C=C1 UEIUWWPUONKVPN-UHFFFAOYSA-N 0.000 claims 1
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 1
HLYWEVACLORZTM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NCC=1N=CC=CC=1)C=C2 HLYWEVACLORZTM-UHFFFAOYSA-N 0.000 claims 1
ILZNHZLGQSARHH-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(OC)C(OC)=C1 ILZNHZLGQSARHH-UHFFFAOYSA-N 0.000 claims 1
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 1
YVCCOOZFAONOQR-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(C)C(C)=CC=C1C1=CN=C2N1N=C(NCC=1C=CN=CC=1)C=C2 YVCCOOZFAONOQR-UHFFFAOYSA-N 0.000 claims 1
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 1
IJYZXBUTGFQNRG-UHFFFAOYSA-N 3-(3-aminophenyl)-n-[(3-chlorophenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound NC1=CC=CC(C=2N3N=C(NCC=4C=C(Cl)C=CC=4)C=CC3=NC=2)=C1 IJYZXBUTGFQNRG-UHFFFAOYSA-N 0.000 claims 1
KTNPSSOGKKPORW-UHFFFAOYSA-N 3-(3-bromophenyl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(Br)=C1 KTNPSSOGKKPORW-UHFFFAOYSA-N 0.000 claims 1
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 1
JGAPOYIZWHCISI-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CN=C2N1N=C(NCCC=1N=CC=CC=1)C=C2 JGAPOYIZWHCISI-UHFFFAOYSA-N 0.000 claims 1
GTRJUOWCXBGRTO-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CN=C2N1N=C(NCCC=1C=NC=CC=1)C=C2 GTRJUOWCXBGRTO-UHFFFAOYSA-N 0.000 claims 1
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 1
IJJYDPYUMJHNQI-UHFFFAOYSA-N 3-(3-chloro-4-fluorophenyl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CN=C2N1N=C(NCC=1N=CC=CC=1)C=C2 IJJYDPYUMJHNQI-UHFFFAOYSA-N 0.000 claims 1
GTIXGBRZVFYBMW-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(Cl)=C1 GTIXGBRZVFYBMW-UHFFFAOYSA-N 0.000 claims 1
VWHUGDIGTGOTHL-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCC=4N=CC=CC=4)C=CC3=NC=2)=C1 VWHUGDIGTGOTHL-UHFFFAOYSA-N 0.000 claims 1
RRMJPRQPCHMQHS-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2-pyrrolidin-1-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCN4CCCC4)C=CC3=NC=2)=C1 RRMJPRQPCHMQHS-UHFFFAOYSA-N 0.000 claims 1
IFAGGZOGELYHAV-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(3-morpholin-4-ylpropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCCN4CCOCC4)C=CC3=NC=2)=C1 IFAGGZOGELYHAV-UHFFFAOYSA-N 0.000 claims 1
VAUXLRFEHFFLNT-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(cyclohexylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCC4CCCCC4)C=CC3=NC=2)=C1 VAUXLRFEHFFLNT-UHFFFAOYSA-N 0.000 claims 1
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 1
INJUKBMQIROUKQ-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCC=4C=CN=CC=4)C=CC3=NC=2)=C1 INJUKBMQIROUKQ-UHFFFAOYSA-N 0.000 claims 1
QOPMWHMRAPKTMK-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-[(2,4-difluorophenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC(F)=CC=C1CNC1=NN2C(C=3C=C(Cl)C=CC=3)=CN=C2C=C1 QOPMWHMRAPKTMK-UHFFFAOYSA-N 0.000 claims 1
MYRHQGMEVLMWSK-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-[(4-fluorophenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1CNC1=NN2C(C=3C=C(Cl)C=CC=3)=CN=C2C=C1 MYRHQGMEVLMWSK-UHFFFAOYSA-N 0.000 claims 1
CZXWJTSKSBKDHX-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-[2-(1,2,4-triazol-1-yl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NCCN4N=CN=C4)C=CC3=NC=2)=C1 CZXWJTSKSBKDHX-UHFFFAOYSA-N 0.000 claims 1
YWLPZPZEWICVRP-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-methyl-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C(Cl)C=CC=3)N2N=C1N(C)CCC1=CC=CC=N1 YWLPZPZEWICVRP-UHFFFAOYSA-N 0.000 claims 1
WEGMAHQXRYVBJO-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-methyl-n-(3-morpholin-4-ylpropyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C(Cl)C=CC=3)N2N=C1N(C)CCCN1CCOCC1 WEGMAHQXRYVBJO-UHFFFAOYSA-N 0.000 claims 1
UCHSONQKULUQQT-UHFFFAOYSA-N 3-(3-fluorophenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC=CC(C=2N3N=C(NCCC=4N=CC=CC=4)C=CC3=NC=2)=C1 UCHSONQKULUQQT-UHFFFAOYSA-N 0.000 claims 1
PNKNZWACOGPCLE-UHFFFAOYSA-N 3-(3-fluorophenyl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC=CC(C=2N3N=C(NCCC=4C=NC=CC=4)C=CC3=NC=2)=C1 PNKNZWACOGPCLE-UHFFFAOYSA-N 0.000 claims 1
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 1
CLOLTFYMRMEARL-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC(C=2N3N=C(NCC=4C=CN=CC=4)C=CC3=NC=2)=C1 CLOLTFYMRMEARL-UHFFFAOYSA-N 0.000 claims 1
PQGFGZFXNAGCNA-UHFFFAOYSA-N 3-(3-methoxyphenyl)-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 PQGFGZFXNAGCNA-UHFFFAOYSA-N 0.000 claims 1
AHKGSTMMFORVGS-UHFFFAOYSA-N 3-(3-methylsulfonylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CS(=O)(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 AHKGSTMMFORVGS-UHFFFAOYSA-N 0.000 claims 1
ROVVLXKULKSDLZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(Cl)C=C1 ROVVLXKULKSDLZ-UHFFFAOYSA-N 0.000 claims 1
GWWCGUUZGOWBJV-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(Cl)=CC=C1C1=CN=C2N1N=C(NCCC=1C=NC=CC=1)C=C2 GWWCGUUZGOWBJV-UHFFFAOYSA-N 0.000 claims 1
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 1
QENAYGTVDARWFN-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NCCC=1N=CC=CC=1)C=C2 QENAYGTVDARWFN-UHFFFAOYSA-N 0.000 claims 1
MRLBIJRTSSQYHB-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NCCC=1C=NC=CC=1)C=C2 MRLBIJRTSSQYHB-UHFFFAOYSA-N 0.000 claims 1
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 1
RTWHAACTLSAUCX-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NCC=1N=CC=CC=1)C=C2 RTWHAACTLSAUCX-UHFFFAOYSA-N 0.000 claims 1
LFMZXGPQHJVNGD-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NCC=1SC=CC=1)C=C2 LFMZXGPQHJVNGD-UHFFFAOYSA-N 0.000 claims 1
PILHWEOIGUULBB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCCC=1N=CC=CC=1)C=C2 PILHWEOIGUULBB-UHFFFAOYSA-N 0.000 claims 1
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 1
GUEYNHORWPWYOO-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1N=CC=CC=1)C=C2 GUEYNHORWPWYOO-UHFFFAOYSA-N 0.000 claims 1
HAASWAGWXFKQFA-UHFFFAOYSA-N 3-(4-methylphenyl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C)=CC=C1C1=CN=C2N1N=C(NCCC=1N=CC=CC=1)C=C2 HAASWAGWXFKQFA-UHFFFAOYSA-N 0.000 claims 1
MBLHAYDJWJNPPO-UHFFFAOYSA-N 3-(4-methylthiophen-2-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CSC(C=2N3N=C(NCCC=4N=CC=CC=4)C=CC3=NC=2)=C1 MBLHAYDJWJNPPO-UHFFFAOYSA-N 0.000 claims 1
MEDCZXFWPUANFF-UHFFFAOYSA-N 3-(4-methylthiophen-2-yl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CSC(C=2N3N=C(NCCC=4C=NC=CC=4)C=CC3=NC=2)=C1 MEDCZXFWPUANFF-UHFFFAOYSA-N 0.000 claims 1
KESRTRBMJYFVLA-UHFFFAOYSA-N 3-(4-methylthiophen-2-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CSC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 KESRTRBMJYFVLA-UHFFFAOYSA-N 0.000 claims 1
XRFGMTSHJMMVLF-UHFFFAOYSA-N 3-(4-methylthiophen-2-yl)-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC(C)=CS1 XRFGMTSHJMMVLF-UHFFFAOYSA-N 0.000 claims 1
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 1
URJNOVDYNRYQIZ-UHFFFAOYSA-N 3-(5-methoxypyridin-3-yl)-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CN=CC(OC)=C1 URJNOVDYNRYQIZ-UHFFFAOYSA-N 0.000 claims 1
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 1
HXZYBDPCZKDEGY-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1N=CC=CC=1)C=C2 HXZYBDPCZKDEGY-UHFFFAOYSA-N 0.000 claims 1
WGYUTOMSUZIWBL-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(OC)N=C1 WGYUTOMSUZIWBL-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
INJGDDZOYJMYNC-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylimidazo[1,2-b]pyridazin-6-yl)amino]propan-1-ol Chemical compound C1=CC=C2C(C3=CN=C4C=CC(=NN43)NCCCO)=CC=CC2=C1 INJGDDZOYJMYNC-UHFFFAOYSA-N 0.000 claims 1
USSSXXAZECOQTH-UHFFFAOYSA-N 3-[3-(dimethylamino)phenyl]-n-(furan-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 USSSXXAZECOQTH-UHFFFAOYSA-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
UDBMIMTWVRWJKX-UHFFFAOYSA-N 3-[3-(dimethylamino)phenyl]-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NCC=4N=CC=CC=4)C=CC3=NC=2)=C1 UDBMIMTWVRWJKX-UHFFFAOYSA-N 0.000 claims 1
FEFWNRKGWJUKHK-UHFFFAOYSA-N 3-[3-(dimethylamino)phenyl]-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 FEFWNRKGWJUKHK-UHFFFAOYSA-N 0.000 claims 1
SGYPWTDOQYCQJR-UHFFFAOYSA-N 3-[3-(dimethylamino)phenyl]-n-propylimidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=CC(N(C)C)=C1 SGYPWTDOQYCQJR-UHFFFAOYSA-N 0.000 claims 1
RWMATJHTHLNUAI-UHFFFAOYSA-N 3-[6-(1,3-benzodioxol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NCC=4C=C5OCOC5=CC=4)C=CC3=NC=2)=C1 RWMATJHTHLNUAI-UHFFFAOYSA-N 0.000 claims 1
OLIUBEHOYWHRLM-UHFFFAOYSA-N 3-[6-(1-hydroxybutan-2-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=CC(C(N)=O)=C1 OLIUBEHOYWHRLM-UHFFFAOYSA-N 0.000 claims 1
DQDJLJACNQULFT-UHFFFAOYSA-N 3-[6-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=2N3N=C(NCCO)C=CC3=NC=2)=C1 DQDJLJACNQULFT-UHFFFAOYSA-N 0.000 claims 1
QJVMVZCRCKBBHN-UHFFFAOYSA-N 3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(C(N)=O)=C1 QJVMVZCRCKBBHN-UHFFFAOYSA-N 0.000 claims 1
NVEYYJDYNLCCCL-UHFFFAOYSA-N 3-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 NVEYYJDYNLCCCL-UHFFFAOYSA-N 0.000 claims 1
BCKLDFMBAZKPEC-UHFFFAOYSA-N 3-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 BCKLDFMBAZKPEC-UHFFFAOYSA-N 0.000 claims 1
AQUWOLAKIUTIIO-UHFFFAOYSA-N 3-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 AQUWOLAKIUTIIO-UHFFFAOYSA-N 0.000 claims 1
RQDYLKYUESAGAI-UHFFFAOYSA-N 3-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 RQDYLKYUESAGAI-UHFFFAOYSA-N 0.000 claims 1
DKVFDNOBAMXZNR-UHFFFAOYSA-N 3-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 DKVFDNOBAMXZNR-UHFFFAOYSA-N 0.000 claims 1
QLSAVVVAAAEDQY-UHFFFAOYSA-N 3-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 QLSAVVVAAAEDQY-UHFFFAOYSA-N 0.000 claims 1
ZMQKPAZWKNMDNP-UHFFFAOYSA-N 3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 ZMQKPAZWKNMDNP-UHFFFAOYSA-N 0.000 claims 1
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 1
FRWXPERGVZDGCF-UHFFFAOYSA-N 3-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=CC(C(N)=O)=C1 FRWXPERGVZDGCF-UHFFFAOYSA-N 0.000 claims 1
BBRVCZSXNXYZKS-UHFFFAOYSA-N 3-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=CC(O)=C1 BBRVCZSXNXYZKS-UHFFFAOYSA-N 0.000 claims 1
LQIYZSBJZMPCFW-UHFFFAOYSA-N 3-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 LQIYZSBJZMPCFW-UHFFFAOYSA-N 0.000 claims 1
FEXUSPAGQLLIDN-UHFFFAOYSA-N 3-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 FEXUSPAGQLLIDN-UHFFFAOYSA-N 0.000 claims 1
LJAFXDCCKCIGRQ-UHFFFAOYSA-N 3-[6-[(4-hydroxycyclohexyl)amino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C(O)C=CC=3)=CN=C2C=C1 LJAFXDCCKCIGRQ-UHFFFAOYSA-N 0.000 claims 1
LCYITTQJQHTOMH-CQSZACIVSA-N 3-[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=CC(O)=C1 LCYITTQJQHTOMH-CQSZACIVSA-N 0.000 claims 1
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 1
WZCRKWIMHVDYQH-UHFFFAOYSA-N 3-[[3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCCO)C=C2 WZCRKWIMHVDYQH-UHFFFAOYSA-N 0.000 claims 1
SCAUYBOPACCASA-UHFFFAOYSA-N 3-[[3-(1h-indol-5-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=C2NC=CC2=CC(C2=CN=C3C=CC(=NN32)NCCCO)=C1 SCAUYBOPACCASA-UHFFFAOYSA-N 0.000 claims 1
FYRONOXEHHGABK-UHFFFAOYSA-N 3-[[3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 FYRONOXEHHGABK-UHFFFAOYSA-N 0.000 claims 1
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 1
YVLYSBVZXCFLAR-UHFFFAOYSA-N 3-[[3-(3-bromophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(Br)=C1 YVLYSBVZXCFLAR-UHFFFAOYSA-N 0.000 claims 1
RGWMMLCNJCTVER-UHFFFAOYSA-N 3-[[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(Cl)=C1 RGWMMLCNJCTVER-UHFFFAOYSA-N 0.000 claims 1
OFAIKJYRWAGFLC-UHFFFAOYSA-N 3-[[3-(4-methylthiophen-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound CC1=CSC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 OFAIKJYRWAGFLC-UHFFFAOYSA-N 0.000 claims 1
DXCJIXNRURQXTH-UHFFFAOYSA-N 3-[[3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NCCCO)C=C2 DXCJIXNRURQXTH-UHFFFAOYSA-N 0.000 claims 1
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 1
UINOZYSCUDKCAE-UHFFFAOYSA-N 3-[[3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(OC(F)(F)F)=C1 UINOZYSCUDKCAE-UHFFFAOYSA-N 0.000 claims 1
TWLBYZFKUYIQMB-UHFFFAOYSA-N 3-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(C(F)(F)F)=C1 TWLBYZFKUYIQMB-UHFFFAOYSA-N 0.000 claims 1
FXDDWVBDBDJXCE-UHFFFAOYSA-N 3-naphthalen-1-yl-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C4=CC=CC=C4C=CC=3)N2N=C1NCCC1=CC=CC=N1 FXDDWVBDBDJXCE-UHFFFAOYSA-N 0.000 claims 1
GEYUFUGFHCUZIF-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCCC1=CC=CC=N1 GEYUFUGFHCUZIF-UHFFFAOYSA-N 0.000 claims 1
RVZRVUCTXWIJDC-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4C=CC=CC4=CC=3)=CN=C2C=C1 RVZRVUCTXWIJDC-UHFFFAOYSA-N 0.000 claims 1
WGKVQHJBOMZULC-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(pyridin-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCC1=CC=CC=N1 WGKVQHJBOMZULC-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
YBGIAZIFYKIZCW-UHFFFAOYSA-N 3-phenyl-n-(2-pyridin-2-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=CC=CC=3)N2N=C1NCCC1=CC=CC=N1 YBGIAZIFYKIZCW-UHFFFAOYSA-N 0.000 claims 1
YDNJTIRZLGOMJY-UHFFFAOYSA-N 3-phenyl-n-(pyridin-3-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CN=CC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CC=C1 YDNJTIRZLGOMJY-UHFFFAOYSA-N 0.000 claims 1
ULEDNDFVPJDVMX-UHFFFAOYSA-N 3-pyridin-3-yl-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CSC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CN=C1 ULEDNDFVPJDVMX-UHFFFAOYSA-N 0.000 claims 1
CQUAUNWOFJBUMF-UHFFFAOYSA-N 3-pyridin-4-yl-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CSC=1CNC(=NN12)C=CC1=NC=C2C1=CC=NC=C1 CQUAUNWOFJBUMF-UHFFFAOYSA-N 0.000 claims 1
IBELUIICIYWCAD-UHFFFAOYSA-N 4-(3-phenylimidazo[1,2-b]pyridazin-6-yl)pentane-1,4-diamine Chemical compound C1(=CC=CC=C1)C1=CN=C2N1N=C(C=C2)C(CCCN)(C)N IBELUIICIYWCAD-UHFFFAOYSA-N 0.000 claims 1
JPFAMXFKSLYAKV-UHFFFAOYSA-N 4-[(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C4C=CC=CC4=CC=3)=CN=C2C=C1 JPFAMXFKSLYAKV-UHFFFAOYSA-N 0.000 claims 1
OZJYVCMJMVXQPR-UHFFFAOYSA-N 4-[(3-phenylimidazo[1,2-b]pyridazin-6-yl)amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=CC=CC=3)=CN=C2C=C1 OZJYVCMJMVXQPR-UHFFFAOYSA-N 0.000 claims 1
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 1
IYSQAAZFUGBLSH-UHFFFAOYSA-N 4-[6-(1,3-benzodioxol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C2N1N=C(NCC=1C=C3OCOC3=CC=1)C=C2 IYSQAAZFUGBLSH-UHFFFAOYSA-N 0.000 claims 1
KKZYGUVAFJCULH-UHFFFAOYSA-N 4-[6-(1-hydroxybutan-2-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound N12N=C(NC(CO)CC)C=CC2=NC=C1C1=CC=C(C(O)=O)C=C1 KKZYGUVAFJCULH-UHFFFAOYSA-N 0.000 claims 1
VUNSHOQRVWQMGL-UHFFFAOYSA-N 4-[6-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CN=C2N1N=C(NCCO)C=C2 VUNSHOQRVWQMGL-UHFFFAOYSA-N 0.000 claims 1
PWCRTXJQBMUION-UHFFFAOYSA-N 4-[6-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCO)C=CC2=NC=C1C1=CC=C(O)C=C1 PWCRTXJQBMUION-UHFFFAOYSA-N 0.000 claims 1
XXCVDOXUKCGNMD-UHFFFAOYSA-N 4-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(C(O)=O)C=C1 XXCVDOXUKCGNMD-UHFFFAOYSA-N 0.000 claims 1
OCAGTIBYJKNQMP-UHFFFAOYSA-N 4-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound COCCNc1ccc2ncc(-c3ccc(O)cc3)n2n1 OCAGTIBYJKNQMP-UHFFFAOYSA-N 0.000 claims 1
OXXLRUSEYRXPGX-UHFFFAOYSA-N 4-[6-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N1(CCOCC1)CCNC=1C=CC=2N(N1)C(=CN2)C2=CC=C(C=C2)O OXXLRUSEYRXPGX-UHFFFAOYSA-N 0.000 claims 1
MBOMKQLHYIQZBT-UHFFFAOYSA-N 4-[6-(2-pyridin-2-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(NCCC=1N=CC=CC=1)C=C2 MBOMKQLHYIQZBT-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
BVUMSYXOGPTUHI-UHFFFAOYSA-N 4-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C2N1N=C(NCC1CC1)C=C2 BVUMSYXOGPTUHI-UHFFFAOYSA-N 0.000 claims 1
HUHYJIGIPJASEA-UHFFFAOYSA-N 4-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound Oc1ccc(cc1)-c1cnc2ccc(NCC3CC3)nn12 HUHYJIGIPJASEA-UHFFFAOYSA-N 0.000 claims 1
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 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
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 1
PFZZHTJWZSSQMY-UHFFFAOYSA-N 4-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(C(O)=O)C=C1 PFZZHTJWZSSQMY-UHFFFAOYSA-N 0.000 claims 1
HMTRPWNXLFLPIP-UHFFFAOYSA-N 4-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(O)C=C1 HMTRPWNXLFLPIP-UHFFFAOYSA-N 0.000 claims 1
FNVZQEAJMYRSPE-UHFFFAOYSA-N 4-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C2N1N=C(NCC=1SC=CC=1)C=C2 FNVZQEAJMYRSPE-UHFFFAOYSA-N 0.000 claims 1
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 1
GFVUTMIVWLEFTP-UHFFFAOYSA-N 4-[6-[(3,4-dichlorophenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=C2N1N=C(NCC=1C=C(Cl)C(Cl)=CC=1)C=C2 GFVUTMIVWLEFTP-UHFFFAOYSA-N 0.000 claims 1
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 1
FPOGRJRXTQQVHF-UHFFFAOYSA-N 4-[6-[(4-hydroxycyclohexyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=CC(=CC=3)C(O)=O)=CN=C2C=C1 FPOGRJRXTQQVHF-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
JQKONLSOBDKPGP-UHFFFAOYSA-N 4-[6-[(4-methoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CNC1=NN2C(C=3C=CC(=CC=3)C(O)=O)=CN=C2C=C1 JQKONLSOBDKPGP-UHFFFAOYSA-N 0.000 claims 1
WTYUGJFSRPGXEL-UHFFFAOYSA-N 4-[6-[3-(dimethylamino)propylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound CN(CCCNC=1C=CC=2N(N1)C(=CN2)C2=CC=C(C=C2)O)C WTYUGJFSRPGXEL-UHFFFAOYSA-N 0.000 claims 1
ZSNVKSHSUYNYCY-SNVBAGLBSA-N 4-[6-[[(2R)-1-hydroxypropan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C[C@H](CO)Nc1ccc2ncc(-c3ccc(O)cc3)n2n1 ZSNVKSHSUYNYCY-SNVBAGLBSA-N 0.000 claims 1
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 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
ICHIOWGYGXKRCC-UHFFFAOYSA-N 4-[[(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=C4C=CC=CC4=CC=3)=CN=C2C=C1 ICHIOWGYGXKRCC-UHFFFAOYSA-N 0.000 claims 1
SIEOWXKVDDKGLO-UHFFFAOYSA-N 4-[[3-(1-benzothiophen-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3SC4=CC=CC=C4C=3)=CN=C2C=C1 SIEOWXKVDDKGLO-UHFFFAOYSA-N 0.000 claims 1
AVHLAUNIFVYHQM-UHFFFAOYSA-N 4-[[3-(1h-indol-5-yl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C4C=CNC4=CC=3)=CN=C2C=C1 AVHLAUNIFVYHQM-UHFFFAOYSA-N 0.000 claims 1
HGALRJXIBQUGIP-UHFFFAOYSA-N 4-[[3-(3,4-dimethylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1=C(C)C(C)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 HGALRJXIBQUGIP-UHFFFAOYSA-N 0.000 claims 1
JLLYTMIYHPRZEL-UHFFFAOYSA-N 4-[[3-(3-chloro-4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C(Cl)C(F)=CC=3)=CN=C2C=C1 JLLYTMIYHPRZEL-UHFFFAOYSA-N 0.000 claims 1
ZBYOUQBNXRSXMJ-UHFFFAOYSA-N 4-[[3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C(F)C=CC=3)=CN=C2C=C1 ZBYOUQBNXRSXMJ-UHFFFAOYSA-N 0.000 claims 1
FVVGYANAWWHSJK-UHFFFAOYSA-N 4-[[3-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound COC1=CC=CC(C=2N3N=C(NC4CCC(O)CC4)C=CC3=NC=2)=C1 FVVGYANAWWHSJK-UHFFFAOYSA-N 0.000 claims 1
AXFWKKMVPHEPDF-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=CC(Cl)=CC=3)=CN=C2C=C1 AXFWKKMVPHEPDF-UHFFFAOYSA-N 0.000 claims 1
PVTBSGNDSLSXPG-UHFFFAOYSA-N 4-[[3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 PVTBSGNDSLSXPG-UHFFFAOYSA-N 0.000 claims 1
YLXNIMCOIFUAQG-UHFFFAOYSA-N 4-[[3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound COC1=CN=CC(C=2N3N=C(NC4CCC(O)CC4)C=CC3=NC=2)=C1 YLXNIMCOIFUAQG-UHFFFAOYSA-N 0.000 claims 1
KPKMGTIXQVVBHF-UHFFFAOYSA-N 4-[[3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 KPKMGTIXQVVBHF-UHFFFAOYSA-N 0.000 claims 1
OWLXLLPPASHLGK-UHFFFAOYSA-N 4-[[3-(furan-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3OC=CC=3)=CN=C2C=C1 OWLXLLPPASHLGK-UHFFFAOYSA-N 0.000 claims 1
MLMXWYQAFJDYMC-UHFFFAOYSA-N 4-[[3-[3-(dimethylamino)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound CN(C)C1=CC=CC(C=2N3N=C(NC4CCC(O)CC4)C=CC3=NC=2)=C1 MLMXWYQAFJDYMC-UHFFFAOYSA-N 0.000 claims 1
LOMZUAFMSBAHAU-UHFFFAOYSA-N 4-[[3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=C(OC(F)(F)F)C=CC=3)=CN=C2C=C1 LOMZUAFMSBAHAU-UHFFFAOYSA-N 0.000 claims 1
OWPBSPAYPIDGQI-UHFFFAOYSA-N 4-[[3-[4-(dimethylamino)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 OWPBSPAYPIDGQI-UHFFFAOYSA-N 0.000 claims 1
MQUCZIJQPLOPGF-UHFFFAOYSA-N 4-[[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1=CC(CO)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 MQUCZIJQPLOPGF-UHFFFAOYSA-N 0.000 claims 1
JSKUWAXBPAIBMS-UHFFFAOYSA-N 4-[[3-[4-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC1=NN2C(C=3C=CC(OC(F)(F)F)=CC=3)=CN=C2C=C1 JSKUWAXBPAIBMS-UHFFFAOYSA-N 0.000 claims 1
QCJRQEZFTIMFJU-UHFFFAOYSA-N 4-[[[3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(NCC=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=NC=2)=C1 QCJRQEZFTIMFJU-UHFFFAOYSA-N 0.000 claims 1
WENVVBBFKOYTGT-UHFFFAOYSA-N 4-[[[3-(3,4-dimethylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(=CC=1)S(N)(=O)=O)C=C2 WENVVBBFKOYTGT-UHFFFAOYSA-N 0.000 claims 1
AAKSLBOWUHCVSI-UHFFFAOYSA-N 4-[[[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NCC=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=NC=2)=C1 AAKSLBOWUHCVSI-UHFFFAOYSA-N 0.000 claims 1
VOMYEYGNTKVIMD-UHFFFAOYSA-N 4-[[[3-(3-chloro-4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=C(Cl)C(F)=CC=3)=CN=C2C=C1 VOMYEYGNTKVIMD-UHFFFAOYSA-N 0.000 claims 1
KHWUPSRNHAZAJU-UHFFFAOYSA-N 4-[[[3-(4-cyanophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NN2C(C=3C=CC(=CC=3)C#N)=CN=C2C=C1 KHWUPSRNHAZAJU-UHFFFAOYSA-N 0.000 claims 1
MWSKGNPDOUBIQN-UHFFFAOYSA-N 4-[[[3-(4-hydroxy-3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=CC(=CC=4)S(N)(=O)=O)C=CC3=NC=2)=C1 MWSKGNPDOUBIQN-UHFFFAOYSA-N 0.000 claims 1
LUBDQVOUAWPGLO-UHFFFAOYSA-N 4-[[[3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(=CC=1)S(N)(=O)=O)C=C2 LUBDQVOUAWPGLO-UHFFFAOYSA-N 0.000 claims 1
DURYIAOGVFGWPD-UHFFFAOYSA-N 4-[[[3-(4-methylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CN=C2N1N=C(NCC=1C=CC(=CC=1)S(N)(=O)=O)C=C2 DURYIAOGVFGWPD-UHFFFAOYSA-N 0.000 claims 1
HNXHLRFYQHILAU-UHFFFAOYSA-N 4-[[[3-[3-(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=C(OC(F)(F)F)C=CC=3)=CN=C2C=C1 HNXHLRFYQHILAU-UHFFFAOYSA-N 0.000 claims 1
QCOVNQDWZFLMLX-UHFFFAOYSA-N CN1N=CC(=C1)C1=CN=C2N1N=C(C=C2)NCCN2CCOCC2.CN2N=CC(=C2)C2=CN=C1N2N=C(C=C1)NCCN1C(NCC1)=O Chemical compound CN1N=CC(=C1)C1=CN=C2N1N=C(C=C2)NCCN2CCOCC2.CN2N=CC(=C2)C2=CN=C1N2N=C(C=C1)NCCN1C(NCC1)=O QCOVNQDWZFLMLX-UHFFFAOYSA-N 0.000 claims 1
CRYUASUDDBHUSH-UHFFFAOYSA-N N-(cyclopropylmethyl)-3-(1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1(CC1)CNC=1C=CC=2N(N1)C(=CN2)C=2C=NNC2 CRYUASUDDBHUSH-UHFFFAOYSA-N 0.000 claims 1
DLTJJTZMPVWXGU-UHFFFAOYSA-N [3-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 DLTJJTZMPVWXGU-UHFFFAOYSA-N 0.000 claims 1
XYMMZTREXZBKMN-UHFFFAOYSA-N [3-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 XYMMZTREXZBKMN-UHFFFAOYSA-N 0.000 claims 1
HPZIZILLXXUWES-UHFFFAOYSA-N [3-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=CC(CO)=C1 HPZIZILLXXUWES-UHFFFAOYSA-N 0.000 claims 1
OXJZOUQPQKTUSX-UHFFFAOYSA-N [4-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(CO)C=C1 OXJZOUQPQKTUSX-UHFFFAOYSA-N 0.000 claims 1
FMUOPXYRVXUKFU-UHFFFAOYSA-N [4-[6-(cyclopropylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CN=C2N1N=C(NCC1CC1)C=C2 FMUOPXYRVXUKFU-UHFFFAOYSA-N 0.000 claims 1
FOQYSXJPSKMQHP-UHFFFAOYSA-N [4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FOQYSXJPSKMQHP-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
IVUBNTNWKIPCPS-UHFFFAOYSA-N imidazopyridazin 1 Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 IVUBNTNWKIPCPS-UHFFFAOYSA-N 0.000 claims 1
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 1
FRQAXURJKRKHEM-UHFFFAOYSA-N methyl 4-[6-[(4-hydroxycyclohexyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CN=C2N1N=C(NC1CCC(O)CC1)C=C2 FRQAXURJKRKHEM-UHFFFAOYSA-N 0.000 claims 1
WNXZIVQGEXALDT-UHFFFAOYSA-N n',n'-diethyl-n-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine Chemical compound N12N=C(NCCCN(CC)CC)C=CC2=NC=C1C=1C=CSC=1 WNXZIVQGEXALDT-UHFFFAOYSA-N 0.000 claims 1
ICLURZHVFBQBJA-UHFFFAOYSA-N n',n'-dimethyl-n-(3-naphthalen-2-ylimidazo[1,2-b]pyridazin-6-yl)ethane-1,2-diamine Chemical compound C1=CC=CC2=CC(C3=CN=C4C=CC(=NN43)NCCN(C)C)=CC=C21 ICLURZHVFBQBJA-UHFFFAOYSA-N 0.000 claims 1
ZJGPNMODLAEECK-UHFFFAOYSA-N n',n'-dimethyl-n-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)ethane-1,2-diamine Chemical compound N12N=C(NCCN(C)C)C=CC2=NC=C1C=1C=CSC=1 ZJGPNMODLAEECK-UHFFFAOYSA-N 0.000 claims 1
DHSCFUMIGRYUKD-UHFFFAOYSA-N n',n'-dimethyl-n-[3-(4-methylphenyl)imidazo[1,2-b]pyridazin-6-yl]ethane-1,2-diamine Chemical compound N12N=C(NCCN(C)C)C=CC2=NC=C1C1=CC=C(C)C=C1 DHSCFUMIGRYUKD-UHFFFAOYSA-N 0.000 claims 1
OMHSSEDNCUEJIP-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1C=C3OCOC3=CC=1)C=C2 OMHSSEDNCUEJIP-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
AGYHLHZCVVMTST-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC(OC)=C(OC)C(OC)=C1 AGYHLHZCVVMTST-UHFFFAOYSA-N 0.000 claims 1
DVJFMXWYGFEZJA-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(OC)=C1 DVJFMXWYGFEZJA-UHFFFAOYSA-N 0.000 claims 1
IVPVMUGYIKBXDY-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(OC)C=C1 IVPVMUGYIKBXDY-UHFFFAOYSA-N 0.000 claims 1
BYTURIPCOKRXSG-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(4-methylthiophen-2-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC(C)=CS1 BYTURIPCOKRXSG-UHFFFAOYSA-N 0.000 claims 1
KJXNCFXMXZPPIP-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CN=CC(OC)=C1 KJXNCFXMXZPPIP-UHFFFAOYSA-N 0.000 claims 1
FBHDDSRWXMUBCV-UHFFFAOYSA-N n-(2-methoxyethyl)-3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(OC)N=C1 FBHDDSRWXMUBCV-UHFFFAOYSA-N 0.000 claims 1
MQWBCFWORDZXTO-UHFFFAOYSA-N n-(2-methoxyethyl)-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(OC(F)(F)F)=C1 MQWBCFWORDZXTO-UHFFFAOYSA-N 0.000 claims 1
ICAUNBNBYFIHJY-UHFFFAOYSA-N n-(2-methoxyethyl)-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(C(F)(F)F)=C1 ICAUNBNBYFIHJY-UHFFFAOYSA-N 0.000 claims 1
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 1
NXEMMYKMCWBGBB-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=CC=CC=3)N2N=C1NCCN1CCOCC1 NXEMMYKMCWBGBB-UHFFFAOYSA-N 0.000 claims 1
GNFMXHSIEYENAE-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C3=CSC=C3)N2N=C1NCCN1CCOCC1 GNFMXHSIEYENAE-UHFFFAOYSA-N 0.000 claims 1
KTRCRDCQKSSCTM-UHFFFAOYSA-N n-(2-pyridin-3-ylethyl)-3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(NCCC=4C=NC=CC=4)C=CC3=NC=2)=C1 KTRCRDCQKSSCTM-UHFFFAOYSA-N 0.000 claims 1
PZKOPCXJRUKPSI-UHFFFAOYSA-N n-(2-pyridin-3-ylethyl)-3-thiophen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3SC=CC=3)N2N=C1NCCC1=CC=CN=C1 PZKOPCXJRUKPSI-UHFFFAOYSA-N 0.000 claims 1
KFVXMVURZYLEQD-UHFFFAOYSA-N n-(2-pyridin-3-ylethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C3=CSC=C3)N2N=C1NCCC1=CC=CN=C1 KFVXMVURZYLEQD-UHFFFAOYSA-N 0.000 claims 1
PEQRZSSSWFJLNO-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCCN1C=NC=C1)C=C2 PEQRZSSSWFJLNO-UHFFFAOYSA-N 0.000 claims 1
QZWLJNMHXXOFDA-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CN=CN1CCCNC(=NN12)C=CC1=NC=C2C1=CC=CC=C1 QZWLJNMHXXOFDA-UHFFFAOYSA-N 0.000 claims 1
BZLWVFZGMMPMGB-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCN1CCCNC(=NN12)C=CC1=NC=C2C1=CC=CC=C1 BZLWVFZGMMPMGB-UHFFFAOYSA-N 0.000 claims 1
WKDWVJWSSAEUAZ-UHFFFAOYSA-N n-(cyclohexylmethyl)-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCC1CCCCC1)C=C2 WKDWVJWSSAEUAZ-UHFFFAOYSA-N 0.000 claims 1
KIOXITXQSYCSLU-UHFFFAOYSA-N n-(cyclohexylmethyl)-3-phenylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1CCCCC1CNC(=NN12)C=CC1=NC=C2C1=CC=CC=C1 KIOXITXQSYCSLU-UHFFFAOYSA-N 0.000 claims 1
DQXSYAFIFPXLMN-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCC1CC1)C=C2 DQXSYAFIFPXLMN-UHFFFAOYSA-N 0.000 claims 1
DRHZCZVOIAOGPT-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 DRHZCZVOIAOGPT-UHFFFAOYSA-N 0.000 claims 1
GWNPJAXVLBFJBG-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 GWNPJAXVLBFJBG-UHFFFAOYSA-N 0.000 claims 1
JDWHANQUDXXKBS-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(4-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NCC1CC1)C=C2 JDWHANQUDXXKBS-UHFFFAOYSA-N 0.000 claims 1
XKXNSCCOMZTCJY-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(4-methylthiophen-2-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound CC1=CSC(C=2N3N=C(NCC4CC4)C=CC3=NC=2)=C1 XKXNSCCOMZTCJY-UHFFFAOYSA-N 0.000 claims 1
NMIKYSJRYKGBMG-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NCC1CC1)C=C2 NMIKYSJRYKGBMG-UHFFFAOYSA-N 0.000 claims 1
UEDQYHKFARMWNA-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-pyridin-4-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1CC1CNC(=NN12)C=CC1=NC=C2C1=CC=NC=C1 UEDQYHKFARMWNA-UHFFFAOYSA-N 0.000 claims 1
MNKKMNSSSZDJOR-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-thiophen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1CC1CNC(=NN12)C=CC1=NC=C2C1=CC=CS1 MNKKMNSSSZDJOR-UHFFFAOYSA-N 0.000 claims 1
MEYVRODACBADLB-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1CC1CNC(=NN12)C=CC1=NC=C2C=1C=CSC=1 MEYVRODACBADLB-UHFFFAOYSA-N 0.000 claims 1
XIWRJRUIIWAXEX-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(1h-indol-5-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CNC4=CC=3)N2N=C1NCC1=CC=CO1 XIWRJRUIIWAXEX-UHFFFAOYSA-N 0.000 claims 1
CPIUJWHTMMHESH-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 CPIUJWHTMMHESH-UHFFFAOYSA-N 0.000 claims 1
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 1
WVXLXQXEVWVLLJ-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(5-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CN=CC(C=2N3N=C(NCC=4OC=CC=4)C=CC3=NC=2)=C1 WVXLXQXEVWVLLJ-UHFFFAOYSA-N 0.000 claims 1
LGSOPWHDJZPMGE-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(6-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 LGSOPWHDJZPMGE-UHFFFAOYSA-N 0.000 claims 1
GXTWMEFIMDJLKA-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-pyridin-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=COC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CN=C1 GXTWMEFIMDJLKA-UHFFFAOYSA-N 0.000 claims 1
SSXPZXJQITXPKU-UHFFFAOYSA-N n-(oxan-4-yl)-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 SSXPZXJQITXPKU-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
ZZQCWNDMAVSBQA-UHFFFAOYSA-N n-(oxan-4-yl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C3=CSC=C3)=CN=C2C=C1 ZZQCWNDMAVSBQA-UHFFFAOYSA-N 0.000 claims 1
KJWDCZZIUXEFSU-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-3-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N3N=C(NCC=4N=CC=CC=4)C=CC3=NC=2)=C1 KJWDCZZIUXEFSU-UHFFFAOYSA-N 0.000 claims 1
VBFZJIKOBURLBJ-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC(F)(F)OC1=CC=CC(C=2N3N=C(NCC=4N=CC=CC=4)C=CC3=NC=2)=C1 VBFZJIKOBURLBJ-UHFFFAOYSA-N 0.000 claims 1
WWHWDGUXQOBMNH-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=C(NCC=4N=CC=CC=4)C=CC3=NC=2)=C1 WWHWDGUXQOBMNH-UHFFFAOYSA-N 0.000 claims 1
IEFBOVRKRDKING-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CC=NC=1CNC(=NN12)C=CC1=NC=C2C=1C=CSC=1 IEFBOVRKRDKING-UHFFFAOYSA-N 0.000 claims 1
NREWEMJUCDKJJV-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=CN=CC=1CNC(=NN12)C=CC1=NC=C2C=1C=CSC=1 NREWEMJUCDKJJV-UHFFFAOYSA-N 0.000 claims 1
XONGYXXYJUTKHA-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=C(NCC=4C=CN=CC=4)C=CC3=NC=2)=C1 XONGYXXYJUTKHA-UHFFFAOYSA-N 0.000 claims 1
KEVKOCFNYTWQDZ-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-3-thiophen-2-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=NC=CC=1CNC(=NN12)C=CC1=NC=C2C1=CC=CS1 KEVKOCFNYTWQDZ-UHFFFAOYSA-N 0.000 claims 1
VDVJFRKOCCCXIT-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCC=1C(=CC(F)=CC=1)F)C=C2 VDVJFRKOCCCXIT-UHFFFAOYSA-N 0.000 claims 1
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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CA2620534A 2005-09-02 2006-09-01 Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments Expired - Fee Related CA2620534C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE102005042742A DE102005042742A1 (de)	2005-09-02	2005-09-02	Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel
DE102005042742.1		2005-09-02
PCT/DE2006/001564 WO2007025540A2 (de)	2005-09-02	2006-09-01	Substituierte imidazo[1,2b]pyridazine als kinase-inhibitoren, deren herstellung und verwendung als arzneimittel

Publications (2)

Publication Number	Publication Date
CA2620534A1 CA2620534A1 (en)	2007-03-08
CA2620534C true CA2620534C (en)	2014-05-27

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ID=37709434

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Application Number	Title	Priority Date	Filing Date
CA2620534A Expired - Fee Related CA2620534C (en)	2005-09-02	2006-09-01	Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments

Country Status (5)

Country	Link
EP (1)	EP2176266A2 (de)
JP (1)	JP5680824B2 (de)
CA (1)	CA2620534C (de)
DE (1)	DE102005042742A1 (de)
WO (1)	WO2007025540A2 (de)

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2005
- 2005-09-02 DE DE102005042742A patent/DE102005042742A1/de not_active Withdrawn
2006
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- 2006-09-01 EP EP06775928A patent/EP2176266A2/de not_active Withdrawn
- 2006-09-01 CA CA2620534A patent/CA2620534C/en not_active Expired - Fee Related
- 2006-09-01 WO PCT/DE2006/001564 patent/WO2007025540A2/de not_active Ceased

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Also Published As

Publication number	Publication date
WO2007025540A3 (de)	2007-05-18
WO2007025540A2 (de)	2007-03-08
CA2620534A1 (en)	2007-03-08
JP5680824B2 (ja)	2015-03-04
JP2009506993A (ja)	2009-02-19
DE102005042742A1 (de)	2007-03-08
EP2176266A2 (de)	2010-04-21

Publication	Publication Date	Title
CA2620534C (en)	2014-05-27	Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments
US7750000B2 (en)	2010-07-06	Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments
EP2536722B1 (de)	2014-04-16	Bicyclische verbindungen und ihre verwendung als duale c-src / jak-hemmer
TWI433677B (zh)	2014-04-11	雜環化合物及其用途
KR101959726B1 (ko)	2019-03-19	2-아릴이미다조[1,2-b]피리다진, 2-페닐이미다조[1,2-a]피리딘, 및 2-페닐이미다조[1,2-a]피라진 유도체들
US8637549B2 (en)	2014-01-28	Pyridons as PDK1 inhibitors
CN101952287B (zh)	2013-11-27	蛋白激酶抑制剂及其应用
TW202244049A (zh)	2022-11-16	Shp2磷酸酶抑制劑的製備及其應用
JP5406030B2 (ja)	2014-02-05	複素環化合物およびそれらのグリコーゲンシンターゼキナーゼ３阻害薬としての使用
CA2679489A1 (en)	2008-09-04	Pyrimidine-2,4-diamine derivatives and their use as jak2 kinase inhibitors
EP1471910A2 (de)	2004-11-03	Substituirte chinazolin-4-ylamine analogue als capsaicinreceptoren-modulatoren
JP2011528026A6 (ja)	2012-09-27	新規化学化合物
CN102203098A (zh)	2011-09-28	作为细胞增殖抑制剂的嘧啶并[5，4-d]嘧啶
IL191213A (en)	2012-02-29	Transformed derivatives in the cycles of pyrimidone
CN100439365C (zh)	2008-12-03	用作蛋白激酶抑制剂的化合物和组合物
CN115515589A (zh)	2022-12-23	Ulk1/2抑制剂及其使用方法
JP2009501176A (ja)	2009-01-15	グリコーゲンシンターゼキナーゼ３阻害薬としてのピリダジン化合物
JP5100639B2 (ja)	2012-12-19	キナーゼ阻害剤としての置換７，８−ジヒドロ−１ｈ−ピリミド［４，５−ｂ］［１，４］ジアゼピン−４−アミン
HK1178897B (en)	2014-07-18	Bicyclic compounds and their uses as dual c-src / jak inhibitors
AU2003205217A1 (en)	2003-09-02	Substituted quinazolin-4-ylamine analogues as modulators of capsaicin

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2011-08-16	EEER	Examination request
2016-10-13	MKLA	Lapsed	Effective date: 20160901

CA2620534C - Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments - Google Patents

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