JP5696052B2 - イミダゾピラジンsyk阻害剤 - Google Patents
イミダゾピラジンsyk阻害剤 Download PDFInfo
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- JP5696052B2 JP5696052B2 JP2011539525A JP2011539525A JP5696052B2 JP 5696052 B2 JP5696052 B2 JP 5696052B2 JP 2011539525 A JP2011539525 A JP 2011539525A JP 2011539525 A JP2011539525 A JP 2011539525A JP 5696052 B2 JP5696052 B2 JP 5696052B2
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyrazin
- indazol
- pyridin
- alkyl
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title description 7
- 102100038183 Tyrosine-protein kinase SYK Human genes 0.000 title description 2
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 title 1
- -1 (2-methyl-2-hydroxypropoxy) pyridin-6-yl Chemical group 0.000 claims description 245
- 150000001875 compounds Chemical class 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- MFSOZUSXQDDCNB-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NN(C(C)C)C=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 MFSOZUSXQDDCNB-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- MFNFCABYKPLVLW-UHFFFAOYSA-N 5-n-[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]-2-n-(2-methoxyethyl)-2-n-methylpyridine-2,5-diamine Chemical compound C1=NC(N(C)CCOC)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 MFNFCABYKPLVLW-UHFFFAOYSA-N 0.000 claims description 4
- BLAURGSMVPJHCW-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 BLAURGSMVPJHCW-UHFFFAOYSA-N 0.000 claims description 4
- JJJFPCRLZYYNSS-UHFFFAOYSA-N 6-(2,3-dimethylindazol-6-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=CC2=C(C)N(C)N=C2C=C1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 JJJFPCRLZYYNSS-UHFFFAOYSA-N 0.000 claims description 4
- WBMQTECYFWQKRK-XMMPIXPASA-N (3r)-1-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-3-methylpiperidin-3-ol Chemical compound C1[C@](C)(O)CCCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 WBMQTECYFWQKRK-XMMPIXPASA-N 0.000 claims description 3
- WBMQTECYFWQKRK-DEOSSOPVSA-N (3s)-1-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-3-methylpiperidin-3-ol Chemical compound C1[C@@](C)(O)CCCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 WBMQTECYFWQKRK-DEOSSOPVSA-N 0.000 claims description 3
- CVWASLZLFGDNNU-UHFFFAOYSA-N 1-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 CVWASLZLFGDNNU-UHFFFAOYSA-N 0.000 claims description 3
- WBMQTECYFWQKRK-UHFFFAOYSA-N 1-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-3-methylpiperidin-3-ol Chemical compound C1C(C)(O)CCCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 WBMQTECYFWQKRK-UHFFFAOYSA-N 0.000 claims description 3
- MUXSPIYQJHBCNC-UHFFFAOYSA-N 1-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]azetidin-3-ol Chemical compound C1C(O)CN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 MUXSPIYQJHBCNC-UHFFFAOYSA-N 0.000 claims description 3
- QLQHBDAWKYKMBQ-UHFFFAOYSA-N 1-[5-[[6-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-3-methylazetidin-3-ol Chemical compound C1C(C)(O)CN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 QLQHBDAWKYKMBQ-UHFFFAOYSA-N 0.000 claims description 3
- GVTLJQGQDUOMGD-UHFFFAOYSA-N 1-[5-[[6-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 GVTLJQGQDUOMGD-UHFFFAOYSA-N 0.000 claims description 3
- AQWARLFPYXVRKX-UHFFFAOYSA-N 1-[5-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 AQWARLFPYXVRKX-UHFFFAOYSA-N 0.000 claims description 3
- SLQZHBCBHXYHRO-UHFFFAOYSA-N 1-[5-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]azetidin-3-ol Chemical compound C1C(O)CN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 SLQZHBCBHXYHRO-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- FDBCUIMAOSMMPA-UHFFFAOYSA-N 2-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 FDBCUIMAOSMMPA-UHFFFAOYSA-N 0.000 claims description 3
- BZNKZCSPQJAFGH-UHFFFAOYSA-N 2-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC(C=2C=C3NCCOC3=CC=2)=CN2C1=NC=C2 BZNKZCSPQJAFGH-UHFFFAOYSA-N 0.000 claims description 3
- SIUAQPJXONHYIN-UHFFFAOYSA-N 2-[4-[[6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC(C=2C=C3OCCNC3=CC=2)=CN2C1=NC=C2 SIUAQPJXONHYIN-UHFFFAOYSA-N 0.000 claims description 3
- SIVKFVXGDZLLQV-UHFFFAOYSA-N 2-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]-2-methylpropan-1-ol Chemical compound C1=NC(C(C)(CO)C)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 SIVKFVXGDZLLQV-UHFFFAOYSA-N 0.000 claims description 3
- KRVYWBSYHNTNST-UHFFFAOYSA-N 2-[5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyridin-2-yl]oxyethanol Chemical compound C1=NC(OCCO)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 KRVYWBSYHNTNST-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- ZZEQEKFGMMZTKM-UHFFFAOYSA-N 3,3-dimethyl-6-[8-[(6-morpholin-4-ylpyridin-3-yl)amino]imidazo[1,2-a]pyrazin-6-yl]-1h-indol-2-one Chemical compound C=1C=C2C(C)(C)C(=O)NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 ZZEQEKFGMMZTKM-UHFFFAOYSA-N 0.000 claims description 3
- RVWUJQUKULSUKG-UHFFFAOYSA-N 3-[4-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyrazol-1-yl]propan-1-ol Chemical compound C1=NN(CCCO)C=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 RVWUJQUKULSUKG-UHFFFAOYSA-N 0.000 claims description 3
- GFFAPGUIXUQLQE-UHFFFAOYSA-N 5-(1h-indol-6-yl)-n-(5-morpholin-4-ylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1COCCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=CC=2)=NC2=CC=NN12 GFFAPGUIXUQLQE-UHFFFAOYSA-N 0.000 claims description 3
- UVNKRRHSMNYXBP-UHFFFAOYSA-N 5-(3-methylbenzimidazol-5-yl)-n-(5-morpholin-4-ylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C2N(C)C=NC2=CC=C1C(=NC1=CC=NN11)C=C1NC(N=C1)=CC=C1N1CCOCC1 UVNKRRHSMNYXBP-UHFFFAOYSA-N 0.000 claims description 3
- AFNKCFWWRHSLFW-UHFFFAOYSA-N 5-(3h-benzimidazol-5-yl)-n-(5-morpholin-4-ylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1COCCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=NC3=CC=2)=NC2=CC=NN12 AFNKCFWWRHSLFW-UHFFFAOYSA-N 0.000 claims description 3
- YYHKIHMXDFCULT-UHFFFAOYSA-N 5-[[6-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]-1h-pyridin-2-one Chemical compound C1=NC(O)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 YYHKIHMXDFCULT-UHFFFAOYSA-N 0.000 claims description 3
- XFCQRUDDAVRMRJ-UHFFFAOYSA-N 6-(1-methylbenzimidazol-5-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C=1C=C2N(C)C=NC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 XFCQRUDDAVRMRJ-UHFFFAOYSA-N 0.000 claims description 3
- OXAWWNWLWPJGSD-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(1h-indol-5-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2C=NNC2=CC(C=2N=C(C3=NC=CN3C=2)NC=2C=C3C=CNC3=CC=2)=C1 OXAWWNWLWPJGSD-UHFFFAOYSA-N 0.000 claims description 3
- REGRKEPTFXYWPD-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(1h-indol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2C=NNC2=CC(C=2N=C(C3=NC=CN3C=2)NC=2C=C3NC=CC3=CC=2)=C1 REGRKEPTFXYWPD-UHFFFAOYSA-N 0.000 claims description 3
- LOZAVAJLPYYTML-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(2-methoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NC(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NN=CC3=CC=2)=C1 LOZAVAJLPYYTML-UHFFFAOYSA-N 0.000 claims description 3
- IOFMPQGEFPONCV-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(2-morpholin-4-ylpyrimidin-5-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(N=C1)=NC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 IOFMPQGEFPONCV-UHFFFAOYSA-N 0.000 claims description 3
- QVALNOBDSBSJDA-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-(3-methylbenzimidazol-5-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2C=NNC2=CC(C=2N=C(C3=NC=CN3C=2)NC2=CC=C3N=CN(C3=C2)C)=C1 QVALNOBDSBSJDA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- ILGMJEFGESPHHU-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-[1-(2-methoxyethyl)pyrazol-4-yl]imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NN(CCOC)C=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 ILGMJEFGESPHHU-UHFFFAOYSA-N 0.000 claims description 3
- YRFVCAQTEKISHD-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-n-[6-(2-methoxyethoxy)pyridin-3-yl]imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NC(OCCOC)=CC=C1NC1=NC(C=2C=C3NN=CC3=CC=2)=CN2C1=NC=C2 YRFVCAQTEKISHD-UHFFFAOYSA-N 0.000 claims description 3
- LKPBCEATGKFYLL-UHFFFAOYSA-N 6-(1h-indol-6-yl)-n-(5-morpholin-4-ylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C1COCCN1C(C=N1)=CC=C1NC1=CC(C=2C=C3NC=CC3=CC=2)=NN2C1=NC=C2 LKPBCEATGKFYLL-UHFFFAOYSA-N 0.000 claims description 3
- ZZTPXLXGKRUVNP-UHFFFAOYSA-N 6-(1h-indol-6-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1COCCN1C(N=C1)=CC=C1NC1=NC(C=2C=C3NC=CC3=CC=2)=CN2C1=NC=C2 ZZTPXLXGKRUVNP-UHFFFAOYSA-N 0.000 claims description 3
- JAIQINBVDXBDCL-UHFFFAOYSA-N 6-(2,3-dihydro-1h-indol-6-yl)-n-(2-methoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=NC(OC)=CC(NC=2C3=NC=CN3C=C(N=2)C=2C=C3NCCC3=CC=2)=C1 JAIQINBVDXBDCL-UHFFFAOYSA-N 0.000 claims description 3
- RJRRMFGLMTXVCJ-UHFFFAOYSA-N 6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2C=NNC2=CC(NC=2C3=NC=CN3C=C(N=2)C2=CC=C3OCCNC3=C2)=C1 RJRRMFGLMTXVCJ-UHFFFAOYSA-N 0.000 claims description 3
- UVVDMEJUOQLGNU-UHFFFAOYSA-N 6-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2NCCOC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 UVVDMEJUOQLGNU-UHFFFAOYSA-N 0.000 claims description 3
- HEDRGLFIFIZNRZ-UHFFFAOYSA-N 6-(3,4-dihydro-2h-1,4-benzoxazin-7-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C=1C=C2NCCOC2=CC=1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 HEDRGLFIFIZNRZ-UHFFFAOYSA-N 0.000 claims description 3
- FJCFYHNLUHAOEQ-UHFFFAOYSA-N 6-(3-amino-1h-indazol-6-yl)-n-(5-morpholin-4-ylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1C=C2C(N)=NNC2=CC=1C(=NN1C=CN=C11)C=C1NC(N=C1)=CC=C1N1CCOCC1 FJCFYHNLUHAOEQ-UHFFFAOYSA-N 0.000 claims description 3
- NVNCYDLJZPDTJU-UHFFFAOYSA-N 6-(3-methylbenzimidazol-5-yl)-n-(6-morpholin-4-ylpyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2N(C)C=NC2=CC=C1C(N=1)=CN2C=CN=C2C=1NC(C=N1)=CC=C1N1CCOCC1 NVNCYDLJZPDTJU-UHFFFAOYSA-N 0.000 claims description 3
- XMIBZUXAYJDEPJ-UHFFFAOYSA-N 6-(3h-benzimidazol-5-yl)-n-(1h-indazol-6-yl)imidazo[1,2-a]pyrazin-8-amine Chemical compound C1=C2N=CNC2=CC(C=2N=C(C3=NC=CN3C=2)NC=2C=C3NN=CC3=CC=2)=C1 XMIBZUXAYJDEPJ-UHFFFAOYSA-N 0.000 claims description 3
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Families Citing this family (73)
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