JP2012510998A5 - - Google Patents
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- JP2012510998A5 JP2012510998A5 JP2011539525A JP2011539525A JP2012510998A5 JP 2012510998 A5 JP2012510998 A5 JP 2012510998A5 JP 2011539525 A JP2011539525 A JP 2011539525A JP 2011539525 A JP2011539525 A JP 2011539525A JP 2012510998 A5 JP2012510998 A5 JP 2012510998A5
- 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.)
- Granted
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- -1 2-methoxy-pyridin-5-yl Chemical group 0.000 claims description 136
- 150000005829 chemical entities Chemical class 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- LDLAEUFQUOXALI-UHFFFAOYSA-N 3-methylazetidin-3-ol Chemical compound CC1(O)CNC1 LDLAEUFQUOXALI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 4
- 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
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 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
- 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
- ORNSLMJWQDGQFF-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=CC=C2NC(=O)COC2=N1 ORNSLMJWQDGQFF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- IRXYTEKDDIDLNG-UHFFFAOYSA-N 2-[4-[[6-(1h-pyrrolo[3,2-b]pyridin-6-yl)imidazo[1,2-a]pyrazin-8-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC(C=2C=C3NC=CC3=NC=2)=CN2C1=NC=C2 IRXYTEKDDIDLNG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 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
- 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 2
- 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 2
- LLDKGUNKYFJNPV-UHFFFAOYSA-N 3-methylpiperidin-3-ol Chemical compound CC1(O)CCCNC1 LLDKGUNKYFJNPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- CXBLQEIODBBSQD-UHFFFAOYSA-N 4-methylpiperidin-4-ol Chemical compound CC1(O)CCNCC1 CXBLQEIODBBSQD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- CGUPZIZXXGKGNQ-UHFFFAOYSA-N 5-(3,4-dihydro-2h-1,4-benzoxazin-6-yl)-n-(5-morpholin-4-ylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=C2NCCOC2=CC=C1C(=NC1=CC=NN11)C=C1NC(N=C1)=CC=C1N1CCOCC1 CGUPZIZXXGKGNQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
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| WO (1) | WO2010068258A1 (https=) |
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-
2009
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- 2009-12-07 JP JP2011539525A patent/JP5696052B2/ja not_active Expired - Fee Related
- 2009-12-07 ES ES09832229T patent/ES2744541T3/es active Active
- 2009-12-07 BR BRPI0922226A patent/BRPI0922226A2/pt not_active IP Right Cessation
- 2009-12-07 EP EP09832229.0A patent/EP2373318B1/en active Active
- 2009-12-07 SG SG2011041266A patent/SG171993A1/en unknown
- 2009-12-07 CN CN200980156329.4A patent/CN102307581B/zh not_active Expired - Fee Related
- 2009-12-07 SG SG10201707798SA patent/SG10201707798SA/en unknown
- 2009-12-07 EP EP19177110.4A patent/EP3552607A3/en not_active Withdrawn
- 2009-12-07 MX MX2011006094A patent/MX2011006094A/es active IP Right Grant
- 2009-12-07 KR KR1020117015710A patent/KR101743784B1/ko not_active Expired - Fee Related
- 2009-12-07 NZ NZ593460A patent/NZ593460A/xx not_active IP Right Cessation
- 2009-12-07 AU AU2009325133A patent/AU2009325133B2/en not_active Ceased
- 2009-12-07 CN CN201410228824.4A patent/CN104059073B/zh not_active Expired - Fee Related
- 2009-12-07 EA EA201190043A patent/EA021293B1/ru not_active IP Right Cessation
- 2009-12-07 WO PCT/US2009/006446 patent/WO2010068258A1/en not_active Ceased
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- 2009-12-07 US US12/632,151 patent/US8440667B2/en not_active Expired - Fee Related
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- 2011-06-06 IL IL213405A patent/IL213405A0/en not_active IP Right Cessation
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- 2014-05-22 JP JP2014105805A patent/JP2014148546A/ja not_active Withdrawn
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