JP2013522238A5 - - Google Patents
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- JP2013522238A5 JP2013522238A5 JP2012557294A JP2012557294A JP2013522238A5 JP 2013522238 A5 JP2013522238 A5 JP 2013522238A5 JP 2012557294 A JP2012557294 A JP 2012557294A JP 2012557294 A JP2012557294 A JP 2012557294A JP 2013522238 A5 JP2013522238 A5 JP 2013522238A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- imidazo
- alkyl
- amine
- indazol
- Prior art date
- 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.)
- Granted
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- -1 3- (4- (tert-butyl) benzamido) -2-methylphenyl Chemical group 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 150000005829 chemical entities Chemical class 0.000 claims description 39
- 230000000694 effects Effects 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
- 125000000335 thiazolyl group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 18
- 230000005764 inhibitory process Effects 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- CJWSQMSEHQXXCY-UHFFFAOYSA-N 1-[2-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-5-yl]ethanone Chemical compound N1=C2C=CNC2=CC(C=2C=C(C3=NC=CN3C=2)NC2=NN3CCN(CC3=C2)C(=O)C)=C1 CJWSQMSEHQXXCY-UHFFFAOYSA-N 0.000 claims description 2
- AAHVXELFAIWJBK-UHFFFAOYSA-N 1-[4-[6-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 AAHVXELFAIWJBK-UHFFFAOYSA-N 0.000 claims description 2
- HHZJQTQNJPCNPC-UHFFFAOYSA-N 1-[4-[6-[[6-[3-(2-hydroxyethyl)-1h-indol-6-yl]imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=C(CCO)C3=CC=2)=CN2C1=NC=C2 HHZJQTQNJPCNPC-UHFFFAOYSA-N 0.000 claims description 2
- AMKMRSDGPQZQLS-UHFFFAOYSA-N 1-[6-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 AMKMRSDGPQZQLS-UHFFFAOYSA-N 0.000 claims description 2
- UYCXAUWDQCPVMY-UHFFFAOYSA-N 1-[6-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 UYCXAUWDQCPVMY-UHFFFAOYSA-N 0.000 claims description 2
- MODZHSLQBONCHV-UHFFFAOYSA-N 1-[6-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]azetidin-3-ol Chemical compound C1C(O)CN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 MODZHSLQBONCHV-UHFFFAOYSA-N 0.000 claims description 2
- IVHDGESMIPKUEO-UHFFFAOYSA-N 1-methyl-6-[5-methyl-8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridin-6-yl]-3h-indol-2-one Chemical compound C1=C2N(C)C(=O)CC2=CC=C1C(=C(N1C=CN=C11)C)C=C1NC(N=C1)=CC=C1N1CCOCC1 IVHDGESMIPKUEO-UHFFFAOYSA-N 0.000 claims description 2
- VYICWLIDANWXNE-UHFFFAOYSA-N 2-[1-methyl-6-[5-methyl-8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridin-6-yl]indol-3-yl]ethanol Chemical compound C12=NC=CN2C(C)=C(C=2C=C3N(C)C=C(CCO)C3=CC=2)C=C1NC(N=C1)=CC=C1N1CCOCC1 VYICWLIDANWXNE-UHFFFAOYSA-N 0.000 claims description 2
- COXUVLHFSMGTNO-UHFFFAOYSA-N 2-[4-[[6-[3-(2-hydroxyethyl)-1h-indol-6-yl]imidazo[1,2-a]pyridin-8-yl]amino]phenyl]-2-methylpropan-1-ol Chemical compound C1=CC(C(C)(CO)C)=CC=C1NC1=CC(C=2C=C3NC=C(CCO)C3=CC=2)=CN2C1=NC=C2 COXUVLHFSMGTNO-UHFFFAOYSA-N 0.000 claims description 2
- QWHKXQBDXJJCHD-UHFFFAOYSA-N 2-[5-methyl-3-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyrazol-1-yl]ethanol Chemical compound OCCN1C(C)=CC(NC=2C3=NC=CN3C=C(C=2)C=2C=C3NC=CC3=NC=2)=N1 QWHKXQBDXJJCHD-UHFFFAOYSA-N 0.000 claims description 2
- LUWFEEPUDGWECA-UHFFFAOYSA-N 2-[6-[5-chloro-8-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-1-methylindol-3-yl]ethanol Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3N(C)C=C(CCO)C3=CC=2)=C(Cl)N2C1=NC=C2 LUWFEEPUDGWECA-UHFFFAOYSA-N 0.000 claims description 2
- WCSIPHYOIZRNNZ-UHFFFAOYSA-N 2-[6-[5-chloro-8-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=C(CCO)C3=CC=2)=C(Cl)N2C1=NC=C2 WCSIPHYOIZRNNZ-UHFFFAOYSA-N 0.000 claims description 2
- CPYZUOJAUGIHIA-UHFFFAOYSA-N 2-[6-[5-chloro-8-[[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-1-methylindol-3-yl]ethanol Chemical compound C1CN(C(C)C)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3N(C)C=C(CCO)C3=CC=2)=C(Cl)N2C1=NC=C2 CPYZUOJAUGIHIA-UHFFFAOYSA-N 0.000 claims description 2
- OEZWQIKWWVKAJI-UHFFFAOYSA-N 2-[6-[5-chloro-8-[[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C1CN(C(C)C)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=C(CCO)C3=CC=2)=C(Cl)N2C1=NC=C2 OEZWQIKWWVKAJI-UHFFFAOYSA-N 0.000 claims description 2
- UJLCAUDXTUPBJP-UHFFFAOYSA-N 2-[6-[8-(6,7-dihydro-4h-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)imidazo[1,2-a]pyridin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C1=C2COCCN2N=C1NC1=CC(C=2C=C3NC=C(C3=CC=2)CCO)=CN2C=CN=C21 UJLCAUDXTUPBJP-UHFFFAOYSA-N 0.000 claims description 2
- XMRNHTWGJJNSMS-UHFFFAOYSA-N 2-[6-[8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C=1C=C2C(CCO)=CNC2=CC=1C(=CN1C=CN=C11)C=C1NC(N=C1)=CC=C1N1CCOCC1 XMRNHTWGJJNSMS-UHFFFAOYSA-N 0.000 claims description 2
- QSKNZFLYYGWRJV-UHFFFAOYSA-N 2-[6-[8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridin-6-yl]-2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-3-yl]ethanol Chemical compound C1CC2C(CCO)NNC2CC1C(=CN1C=CN=C11)C=C1NC(N=C1)=CC=C1N1CCOCC1 QSKNZFLYYGWRJV-UHFFFAOYSA-N 0.000 claims description 2
- VMJQTHKIUMLGNI-UHFFFAOYSA-N 2-[6-[8-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]-5-methylimidazo[1,2-a]pyridin-6-yl]-1h-indol-3-yl]ethanol Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=C(CCO)C3=CC=2)=C(C)N2C1=NC=C2 VMJQTHKIUMLGNI-UHFFFAOYSA-N 0.000 claims description 2
- OHRHYLMKOWOKNP-UHFFFAOYSA-N 2-[6-[8-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-3-yl]ethanol Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C2CC3NNC(CCO)C3CC2)=CN2C1=NC=C2 OHRHYLMKOWOKNP-UHFFFAOYSA-N 0.000 claims description 2
- XIQBMHMYQXKVNB-UHFFFAOYSA-N 2-[ethyl-[6-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]amino]ethanol Chemical compound N1=CC(N(CCO)CC)=CC=C1NC1=CC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 XIQBMHMYQXKVNB-UHFFFAOYSA-N 0.000 claims description 2
- XLWBHWLYRXBZRX-UHFFFAOYSA-N 2-hydroxy-1-[4-[6-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]amino]pyridin-3-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 XLWBHWLYRXBZRX-UHFFFAOYSA-N 0.000 claims description 2
- GVZHUWSLJZJBOW-UHFFFAOYSA-N 2-n-[6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-yl]-5-n-(2-methoxyethyl)-5-n-methylpyridine-2,5-diamine Chemical compound N1=CC(N(C)CCOC)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 GVZHUWSLJZJBOW-UHFFFAOYSA-N 0.000 claims description 2
- KEZHRKOVLKUYCQ-UHFFFAOYSA-N 3,3-dimethyl-1h-indol-2-one Chemical compound C1=CC=C2C(C)(C)C(=O)NC2=C1 KEZHRKOVLKUYCQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- ARLTZSGJPGABLS-UHFFFAOYSA-N 3-(2-hydroxyethyl)-6-[8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridin-6-yl]-1h-benzimidazol-2-one Chemical compound C1=C2NC(=O)N(CCO)C2=CC=C1C(=CN1C=CN=C11)C=C1NC(N=C1)=CC=C1N1CCOCC1 ARLTZSGJPGABLS-UHFFFAOYSA-N 0.000 claims description 2
- TTXXVRQVMWILOX-UHFFFAOYSA-N 5-chloro-n-[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]-6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=C(Cl)N2C1=NC=C2 TTXXVRQVMWILOX-UHFFFAOYSA-N 0.000 claims description 2
- JCGQOBWKAYVSHM-UHFFFAOYSA-N 5-chloro-n-[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]-6-(1h-indol-6-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=CC=2)=C(Cl)N2C1=NC=C2 JCGQOBWKAYVSHM-UHFFFAOYSA-N 0.000 claims description 2
- NGNYRZRWQFOUFK-UHFFFAOYSA-N 5-ethyl-n-[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]-6-(1h-indazol-6-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=C(CC)N2C1=NC=C2 NGNYRZRWQFOUFK-UHFFFAOYSA-N 0.000 claims description 2
- HYULMKQXSAMIIE-UHFFFAOYSA-N 5-ethyl-n-[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]-6-(1h-indol-6-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=CC=2)=C(CC)N2C1=NC=C2 HYULMKQXSAMIIE-UHFFFAOYSA-N 0.000 claims description 2
- SMDZKFNTPDKVCD-UHFFFAOYSA-N 5-methyl-n-(5-morpholin-4-ylpyridin-2-yl)-6-(1h-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC=CN2C(C)=C(C=2C=C3C=CNC3=NC=2)C=C1NC(N=C1)=CC=C1N1CCOCC1 SMDZKFNTPDKVCD-UHFFFAOYSA-N 0.000 claims description 2
- VVVAHIMKXLXSAZ-UHFFFAOYSA-N 5-methyl-n-[6-(1h-pyrazolo[4,3-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-2-amine Chemical compound N1=C2C=NNC2=CC(C=2C=C(C3=NC=CN3C=2)NC2=NN3CCN(CC3=C2)C)=C1 VVVAHIMKXLXSAZ-UHFFFAOYSA-N 0.000 claims description 2
- XGIBBFYEAXESGG-UHFFFAOYSA-N 5-methylsulfonyl-n-[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyridin-8-yl]-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-2-amine Chemical compound N1=C2C=CNC2=CC(C=2C=C(C3=NC=CN3C=2)NC2=NN3CCN(CC3=C2)S(=O)(=O)C)=C1 XGIBBFYEAXESGG-UHFFFAOYSA-N 0.000 claims description 2
- HFLJFLGBUYZUQI-UHFFFAOYSA-N 6-(1,3-benzothiazol-5-yl)-n-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C(OC)C(OC)=CC=C1NC1=CC(C=2C=C3N=CSC3=CC=2)=CN2C1=NC=C2 HFLJFLGBUYZUQI-UHFFFAOYSA-N 0.000 claims description 2
- VNVXBPDUZLOFDL-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridine-5-carboxylic acid Chemical compound C12=NC=CN2C(C(=O)O)=C(C=2C=C3NN=CC3=CC=2)C=C1NC(N=C1)=CC=C1N1CCOCC1 VNVXBPDUZLOFDL-UHFFFAOYSA-N 0.000 claims description 2
- MMVVVHCESUZDJQ-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(1-methylpyrazol-3-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound CN1C=CC(NC=2C3=NC=CN3C=C(C=2)C=2C=C3NN=CC3=CC=2)=N1 MMVVVHCESUZDJQ-UHFFFAOYSA-N 0.000 claims description 2
- RXLYIOCBKNBFKY-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(2-methoxypyrimidin-4-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound COC1=NC=CC(NC=2C3=NC=CN3C=C(C=2)C=2C=C3NN=CC3=CC=2)=N1 RXLYIOCBKNBFKY-UHFFFAOYSA-N 0.000 claims description 2
- ASOHWEMFUOHJIO-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(5-morpholin-4-ylpyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1COCCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ASOHWEMFUOHJIO-UHFFFAOYSA-N 0.000 claims description 2
- SMDZVMZCRFMZLC-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(6-morpholin-4-ylpyridazin-3-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1COCCN1C(N=N1)=CC=C1NC1=CC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 SMDZVMZCRFMZLC-UHFFFAOYSA-N 0.000 claims description 2
- ZWZYOUWAHJEIEO-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-pyrimidin-4-ylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C(C=2C=C3NN=CC3=CC=2)=CN2C=CN=C2C=1NC1=CC=NC=N1 ZWZYOUWAHJEIEO-UHFFFAOYSA-N 0.000 claims description 2
- OPBMELYINMFWHW-UHFFFAOYSA-N 6-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-6-yl)-5-chloro-N-[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound CC(C)N1CCN(CC1)C2=CN=C(C=C2)NC3=CC(=C(N4C3=NC=C4)Cl)C5CCC6CNNC6C5 OPBMELYINMFWHW-UHFFFAOYSA-N 0.000 claims description 2
- AVVSZNQPPXNDTD-UHFFFAOYSA-N 6-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-6-yl)-5-fluoro-N-[5-(4-propan-2-ylpiperazin-1-yl)pyridin-2-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound CC(C)N1CCN(CC1)C2=CN=C(C=C2)NC3=CC(=C(N4C3=NC=C4)F)C5CCC6CNNC6C5 AVVSZNQPPXNDTD-UHFFFAOYSA-N 0.000 claims description 2
- ZUALLIRHZKQFCS-UHFFFAOYSA-N 6-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-6-yl)-5-methyl-N-(5-morpholin-4-ylpyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound CC1=C(C=C(C2=NC=CN12)NC3=NC=C(C=C3)N4CCOCC4)C5CCC6CNNC6C5 ZUALLIRHZKQFCS-UHFFFAOYSA-N 0.000 claims description 2
- POQYKNCZHZAFJV-UHFFFAOYSA-N 6-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-6-yl)-8-[(5-morpholin-4-ylpyridin-2-yl)amino]imidazo[1,2-a]pyridine-5-carboxamide Chemical compound C1CC2CNNC2CC1C3=C(N4C=CN=C4C(=C3)NC5=NC=C(C=C5)N6CCOCC6)C(=O)N POQYKNCZHZAFJV-UHFFFAOYSA-N 0.000 claims description 2
- WKMHWRRKVGSIQB-UHFFFAOYSA-N 6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(1,5-dimethylpyrazol-3-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound CN1C(C)=CC(NC=2C3=NC=CN3C=C(C=2)C=2C=C3NCCOC3=CC=2)=N1 WKMHWRRKVGSIQB-UHFFFAOYSA-N 0.000 claims description 2
- TVEGHVLNCAEJCT-UHFFFAOYSA-N 6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C(OC)C(OC)=CC=C1NC1=CC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 TVEGHVLNCAEJCT-UHFFFAOYSA-N 0.000 claims description 2
- GVROMDVQUCKWGE-UHFFFAOYSA-N 6-[5-chloro-8-[[5-(4-ethylpiperazin-1-yl)pyridin-2-yl]amino]imidazo[1,2-a]pyridin-6-yl]-1,3-dihydroindol-2-one Chemical compound C1CN(CC)CCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC(=O)CC3=CC=2)=C(Cl)N2C1=NC=C2 GVROMDVQUCKWGE-UHFFFAOYSA-N 0.000 claims description 2
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2011
- 2011-03-11 CN CN201180023252.0A patent/CN103168039B/zh not_active Expired - Fee Related
- 2011-03-11 AU AU2011226689A patent/AU2011226689B2/en active Active
- 2011-03-11 WO PCT/US2011/028194 patent/WO2011112995A1/en not_active Ceased
- 2011-03-11 JP JP2012557294A patent/JP5938352B2/ja active Active
- 2011-03-11 BR BR112012022943A patent/BR112012022943A2/pt not_active Application Discontinuation
- 2011-03-11 NZ NZ602362A patent/NZ602362A/en not_active IP Right Cessation
- 2011-03-11 CA CA2792769A patent/CA2792769C/en active Active
- 2011-03-11 PT PT117096008T patent/PT2545052E/pt unknown
- 2011-03-11 ES ES11709600T patent/ES2530449T3/es active Active
- 2011-03-11 EP EP11709600.8A patent/EP2545052B1/en active Active
- 2011-03-11 KR KR1020127026472A patent/KR101717809B1/ko not_active Expired - Fee Related
- 2011-03-11 MX MX2012010418A patent/MX350010B/es active IP Right Grant
- 2011-03-11 US US13/806,094 patent/US9562056B2/en not_active Expired - Fee Related
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2015
- 2015-05-05 JP JP2015094508A patent/JP6177828B2/ja not_active Expired - Fee Related
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2016
- 2016-08-23 AU AU2016219585A patent/AU2016219585B2/en active Active
- 2016-12-21 US US15/387,557 patent/US10092583B2/en active Active
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2017
- 2017-07-13 JP JP2017136797A patent/JP2017222685A/ja not_active Withdrawn
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- 2018-09-06 US US16/124,113 patent/US10842803B2/en not_active Expired - Fee Related
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