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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ587039A (en) | 2008-02-13 | 2013-01-25 | Gilead Connecticut Inc | 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof |
| CN104744476B (zh) | 2008-12-08 | 2017-04-12 | 吉利德康涅狄格公司 | 咪唑并吡嗪syk抑制剂 |
| SG171993A1 (en) | 2008-12-08 | 2011-07-28 | Gilead Connecticut Inc | Imidazopyrazine syk inhibitors |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| US9951008B2 (en) * | 2009-11-03 | 2018-04-24 | University Of Notre Dame Du Lac | Ionic liquids comprising heteraromatic anions |
| US8440689B2 (en) | 2009-12-23 | 2013-05-14 | Takeda Pharmaceutical Company Limited | Fused heteroaromatic pyrrolidinones |
| WO2011100341A1 (en) * | 2010-02-09 | 2011-08-18 | Drexel University | New signaling molecule involved in ultraviolet damage to skin |
| NZ602362A (en) | 2010-03-11 | 2014-11-28 | Gilead Connecticut Inc | Imidazopyridines syk inhibitors |
| AU2012244550C1 (en) | 2011-04-21 | 2017-06-22 | Origenis Gmbh | Pyrazolo [4, 3-d] pyrimidines useful as kinase inhibitors |
| JP2014513687A (ja) | 2011-05-10 | 2014-06-05 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｓｙｋ阻害薬としてのピリジルアミノピリジン |
| EP2706852B1 (en) | 2011-05-10 | 2018-08-22 | Merck Sharp & Dohme Corp. | Bipyridylaminopyridines as syk inhibitors |
| EP2723739B1 (en) | 2011-06-22 | 2016-08-24 | Takeda Pharmaceutical Company Limited | Substituted 6-aza-isoindolin-1-one derivatives |
| EP2763976B1 (en) | 2011-10-05 | 2016-05-18 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| WO2013052393A1 (en) | 2011-10-05 | 2013-04-11 | Merck Sharp & Dohme Corp. | 3-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| EP2763974B1 (en) | 2011-10-05 | 2016-09-14 | Merck Sharp & Dohme Corp. | Phenyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| RU2662443C2 (ru) * | 2011-11-01 | 2018-07-26 | Ф. Хоффманн-Ля Рош Аг | Имидазопиридазины |
| MX351958B (es) | 2011-12-09 | 2017-11-06 | Chiesi Farm Spa | Inhibidores de cinasa. |
| WO2013083604A1 (en) | 2011-12-09 | 2013-06-13 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
| CN104159891B (zh) | 2012-01-10 | 2016-09-07 | 霍夫曼-拉罗奇有限公司 | 哒嗪酰胺化合物和它们作为syk 抑制剂的用途 |
| US20130338142A1 (en) * | 2012-06-14 | 2013-12-19 | Gilead Connecticut, Inc. | Imidazopyrazine syk inhibitors |
| WO2013192128A1 (en) | 2012-06-20 | 2013-12-27 | Merck Sharp & Dohme Corp. | Imidazolyl analogs as syk inhibitors |
| WO2013192125A1 (en) | 2012-06-20 | 2013-12-27 | Merck Sharp & Dohme Corp. | Pyrazolyl derivatives as syk inhibitors |
| US9416111B2 (en) | 2012-06-22 | 2016-08-16 | Merck Sharp & Dohme Corp. | Substituted diazine and triazine spleen tyrosine kinease (Syk) inhibitors |
| EP2863916B1 (en) | 2012-06-22 | 2018-07-18 | Merck Sharp & Dohme Corp. | Substituted pyridine spleen tyrosine kinase (syk) inhibitors |
| WO2014031438A2 (en) | 2012-08-20 | 2014-02-27 | Merck Sharp & Dohme Corp. | SUBSTITUTED PHENYL SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| HK1213181A1 (zh) | 2012-09-27 | 2016-06-30 | Portola Pharmaceuticals, Inc. | 雙環氧雜內酰胺激酶抑制劑 |
| EP2900665B1 (en) | 2012-09-28 | 2018-01-03 | Merck Sharp & Dohme Corp. | Triazolyl derivatives as syk inhibitors |
| US9637491B2 (en) | 2012-10-19 | 2017-05-02 | Origenis Gmbh | Pyrazolo[4,3-D]pyrimidines as kinase inhibitors |
| CA2890105C (en) | 2012-11-01 | 2023-03-21 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| WO2014093191A1 (en) | 2012-12-12 | 2014-06-19 | Merck Sharp & Dohme Corp. | AMINO-PYRIMIDINE-CONTAINING SPLEEN TYROSINE KINASE (Syk) INHIBITORS |
| EP2934525B1 (en) | 2012-12-21 | 2019-05-08 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyridines as spleen tyrosine kinase inhibitors |
| WO2014151386A1 (en) | 2013-03-15 | 2014-09-25 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| WO2014176210A1 (en) | 2013-04-26 | 2014-10-30 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| EP2988749B1 (en) | 2013-04-26 | 2019-08-14 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminopyrimidines as spleen tyrosine kinase inhibitors |
| BR112015029969A2 (pt) | 2013-05-30 | 2017-07-25 | Infinity Pharmaceuticals Inc | tratamento de câncer usando moduladores de isoformas quinase pi3 |
| AR096532A1 (es) | 2013-06-06 | 2016-01-13 | Chiesi Farm Spa | Inhibidores de quinasa |
| EP3027171B1 (en) | 2013-07-30 | 2020-03-25 | Gilead Connecticut, Inc. | Formulation of syk inhibitors |
| EA201791873A1 (ru) | 2013-07-30 | 2018-09-28 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| JP6159028B2 (ja) | 2013-07-31 | 2017-07-05 | ギリアード サイエンシーズ， インコーポレイテッド | Ｓｙｋ阻害剤 |
| WO2015048765A1 (en) | 2013-09-30 | 2015-04-02 | University Of Notre Dame Du Lac | Compounds, complexes, compositions, methods and systems for heating and cooling |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG10201902074UA (en) | 2013-10-04 | 2019-04-29 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| WO2015061204A1 (en) | 2013-10-21 | 2015-04-30 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US10086331B2 (en) | 2013-11-05 | 2018-10-02 | University Of Notre Dame Du Lac | Carbon dioxide capture using phase change ionic liquids |
| KR20180002888A (ko) * | 2013-12-04 | 2018-01-08 | 길리애드 사이언시즈, 인코포레이티드 | 암을 치료하는 방법 |
| EP3083559B1 (en) | 2013-12-20 | 2021-03-10 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| EP3083560B1 (en) | 2013-12-20 | 2021-10-27 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| US9783531B2 (en) | 2013-12-20 | 2017-10-10 | Merck Sharp & Dohme Corp. | Thiazole-substituted aminoheteroaryls as spleen tyrosine kinase inhibitors |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| UY35898A (es) | 2013-12-23 | 2015-07-31 | Gilead Sciences Inc | ?compuestos inhibidores de syk y composiciones que los comprenden?. |
| EP3116506B1 (en) | 2014-03-13 | 2019-04-17 | Merck Sharp & Dohme Corp. | 2-pyrazine carboxamides as spleen tyrosine kinase inhibitors |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| WO2015160986A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2015157955A1 (en) | 2014-04-17 | 2015-10-22 | Abbvie Inc. | Heterocyclic btk inhibit ors |
| CN106687139A (zh) | 2014-07-14 | 2017-05-17 | 吉利德科学公司 | 用于治疗癌症的组合 |
| TW201617074A (zh) * | 2014-07-14 | 2016-05-16 | 吉李德科學股份有限公司 | Ｓｙｋ（脾酪胺酸激酶）抑制劑 |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2016197987A1 (zh) * | 2015-06-12 | 2016-12-15 | 杭州英创医药科技有限公司 | 作为Syk抑制剂和/或Syk-HDAC双重抑制剂的杂环化合物 |
| EA033978B1 (ru) * | 2015-09-11 | 2019-12-16 | Бёрингер Ингельхайм Интернациональ Гмбх | Пиразолилзамещенные гетероарилы и их применение в качестве лекарственных средств |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2017223422A1 (en) | 2016-06-24 | 2017-12-28 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| TW201822764A (zh) | 2016-09-14 | 2018-07-01 | 美商基利科學股份有限公司 | Syk抑制劑 |
| CA3036384A1 (en) | 2016-09-14 | 2018-03-22 | Gilead Sciences, Inc. | Syk inhibitors |
| EP3553065A4 (en) * | 2016-12-12 | 2020-07-01 | Hangzhou Innogate Pharma Co., Ltd. | HETEROCYCLIC COMPOUND AS SYK INHIBITOR AND / OR DUAL SYK-HDAC INHIBITOR |
| WO2018195471A1 (en) | 2017-04-21 | 2018-10-25 | Gilead Sciences, Inc. | Syk inhibitors in combination with hypomethylating agents |
| CN111051311A (zh) | 2017-08-25 | 2020-04-21 | 吉利德科学公司 | Syk抑制剂的多晶型物 |
| CN112165944B (zh) * | 2018-03-29 | 2024-04-09 | 德州大学系统董事会 | 转录激活蛋白的咪唑并哌嗪抑制剂 |
| KR20210131372A (ko) | 2019-02-22 | 2021-11-02 | 크로노스 바이오, 인코포레이티드 | Syk 억제제로서의 축합된 피라진의 고체 형태 |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| JP2023500906A (ja) | 2019-11-08 | 2023-01-11 | インサーム（インスティテュ ナシオナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシェ メディカル） | キナーゼ阻害剤に対する獲得抵抗性を有するがんの処置方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN120239624A (zh) | 2022-11-23 | 2025-07-01 | 皇家飞利浦有限公司 | 控制触觉呼吸引导设备 |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337609A (en) | 1980-09-17 | 1982-07-06 | Pitney Bowes Inc. | Envelope stuffing apparatus |
| FR2607813B1 (fr) | 1986-12-05 | 1989-03-31 | Montpellier I Universite | Alkylamino-8 imidazo (1,2-a) pyrazines et derives, leur preparation et leur application en therapeutique |
| US5137876A (en) | 1990-10-12 | 1992-08-11 | Merck & Co., Inc. | Nucleoside antiviral and anti-inflammatory compounds and compositions and methods for using same |
| DE4327027A1 (de) | 1993-02-15 | 1994-08-18 | Bayer Ag | Imidazoazine |
| DE4337609A1 (de) | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4337611A1 (de) | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Benzoylguanidine, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4337656C2 (de) | 1993-11-04 | 1996-01-18 | Audi Ag | Insassenschutzvorrichtung für Kraftfahrzeuge |
| FR2711993B1 (fr) | 1993-11-05 | 1995-12-01 | Rhone Poulenc Rorer Sa | Médicaments contenant des dérivés de 7H-imidazol[1,2-a]pyrazine-8-one, les nouveaux composés et leur préparation. |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| WO1995026325A2 (en) | 1994-03-25 | 1995-10-05 | Isotechnika Inc. | Enhancement of the efficacy of drugs by deuteration |
| FR2723373B1 (fr) | 1994-08-02 | 1996-09-13 | Rhone Poulenc Rorer Sa | Forme purifiee de streptogramines, sa preparation et les compositions pharmaceutiques qui la contiennent |
| JPH11505524A (ja) | 1995-05-01 | 1999-05-21 | 藤沢薬品工業株式会社 | イミダゾ１，２−ａピリジンおよびイミダゾ１，２−ａピリデジン誘導体、および骨吸収阻害剤としてのその用途 |
| US5593997A (en) | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| US6249495B1 (en) | 1997-02-27 | 2001-06-19 | Matsushita Electric Industrial Co., Ltd. | Stepping motor control method and disk drive apparatus |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| DE19948434A1 (de) | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| JP2001302667A (ja) | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| AU2001275076A1 (en) | 2000-06-19 | 2002-01-02 | Armin S. Tay | Axial position changing transmission mechanism |
| GB0018473D0 (en) | 2000-07-27 | 2000-09-13 | Merck Sharp & Dohme | Therapeutic agents |
| DE10050663A1 (de) | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| US20030089434A1 (en) | 2000-11-20 | 2003-05-15 | Flynn Thomas M. | Method and apparatus for the preparation and usage of a cryogenic propellant or explosive system |
| DK174233B1 (da) | 2000-12-27 | 2002-10-07 | Dss Danish Separation Systems | Sanitært spiralfilteranlæg |
| US20040102455A1 (en) | 2001-01-30 | 2004-05-27 | Burns Christopher John | Method of inhibiting kinases |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| WO2002076985A1 (en) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| US7230941B2 (en) | 2001-04-26 | 2007-06-12 | Qualcomm Incorporated | Preamble channel decoding |
| FR2824092B1 (fr) | 2001-04-30 | 2004-04-09 | Camille Jim Riviere | Ensemble d'elements de construction |
| US7003125B2 (en) | 2001-09-12 | 2006-02-21 | Seung-Hwan Yi | Micromachined piezoelectric microspeaker and fabricating method thereof |
| EP1308716A1 (en) * | 2001-10-03 | 2003-05-07 | Avantium International B.V. | Method for performing a transmission diffraction analysis |
| AU2003219690A1 (en) | 2002-02-19 | 2003-09-09 | Pharmacia And Upjohn Company | Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease |
| IL164703A0 (en) | 2002-04-19 | 2005-12-18 | Cellular Genomics Inc | ImidazoÄ1,2-AÜpyrazin-8-ylamines method of making and method of use thereof |
| KR20040012451A (ko) | 2002-05-14 | 2004-02-11 | 어플라이드 머티어리얼스, 인코포레이티드 | 포토리소그래픽 레티클을 에칭하는 방법 |
| JP2004053714A (ja) | 2002-07-17 | 2004-02-19 | Fuji Xerox Co Ltd | 画像定着装置及び画像定着方法 |
| US6761361B2 (en) | 2002-08-09 | 2004-07-13 | Credo Technology Corporation | Drill and drive apparatus with improved tool holder |
| US20040026867A1 (en) | 2002-08-09 | 2004-02-12 | Adams David J. | Bearing seal |
| AU2003270489A1 (en) | 2002-09-09 | 2004-03-29 | Cellular Genomics, Inc. | 6-ARYL-IMIDAZO(1,2-a)PYRAZIN-8-YLAMINES, METHOD OF MAKING, AND METHOD OF USE THEREOF |
| EP1539756B1 (en) | 2002-09-19 | 2007-11-14 | Schering Corporation | Imidazopyridines as cyclin dependent kinase inhibitors |
| WO2004026310A1 (en) | 2002-09-23 | 2004-04-01 | Schering Corporation | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
| TW200413378A (en) | 2002-09-23 | 2004-08-01 | Schering Corp | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
| JP4056346B2 (ja) | 2002-09-30 | 2008-03-05 | 三洋電機株式会社 | 非水電解質二次電池 |
| JP5118302B2 (ja) | 2002-10-29 | 2013-01-16 | トランセイブ， インク． | 抗感染剤の徐放 |
| WO2004072080A1 (en) | 2003-02-10 | 2004-08-26 | Cellular Genomics, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of hsp90 complex activity |
| AR043002A1 (es) | 2003-02-18 | 2005-07-13 | Altana Pharma Ag | Imidazopirazinas 6-substituidos |
| US7157460B2 (en) | 2003-02-20 | 2007-01-02 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7186832B2 (en) | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| US7456393B2 (en) | 2003-04-10 | 2008-11-25 | Ge Homeland Protection, Inc. | Device for testing surfaces of articles for traces of explosives and/or drugs |
| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| US20060183746A1 (en) * | 2003-06-04 | 2006-08-17 | Currie Kevin S | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| WO2005005429A1 (en) * | 2003-06-30 | 2005-01-20 | Cellular Genomics, Inc. | Certain heterocyclic substituted imidazo[1,2-a]pyrazin-8-ylamines and methods of inhibition of bruton’s tyrosine kinase by such compounds |
| US20050009632A1 (en) * | 2003-07-08 | 2005-01-13 | Karsten Manufacturing Corporation | Iron type golf club head with low profile tuning port |
| WO2005019220A2 (en) | 2003-08-11 | 2005-03-03 | Cellular Genomics Inc. | Substituted imidazo[1,2-a]pyrazines as modulators of kinase activity |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7236749B2 (en) | 2003-10-15 | 2007-06-26 | Honeywell International Inc. | Stuck microphone deselection system and method |
| US20050288295A1 (en) | 2003-11-11 | 2005-12-29 | Currie Kevin S | Certain imidazo[1,2-a]pyrazin-8-ylamines, method of making, and method of use thereof |
| WO2005085252A1 (en) | 2004-03-04 | 2005-09-15 | Biofocus Discovery Limited | Imidazo ‘1,2-a’ pyrazine compounds which interact with protein kinases |
| JP2006099930A (ja) | 2004-09-01 | 2006-04-13 | Tdk Corp | 情報記録媒体、記録再生装置およびスタンパー |
| US8145601B2 (en) | 2004-09-09 | 2012-03-27 | Microsoft Corporation | Method, system, and apparatus for providing resilient data transfer in a data protection system |
| US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| NZ555681A (en) | 2004-11-10 | 2009-08-28 | Cgi Pharmaceuticals Inc | Imidazo[1, 2-a] pyrazin-8-ylamines useful as modulators of kinase activity |
| CN101124227A (zh) | 2004-11-10 | 2008-02-13 | Cgi制药有限公司 | 可用作激酶活性调节剂的咪唑并[1,2-a]吡嗪-8-基胺 |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| JP4883959B2 (ja) | 2005-08-17 | 2012-02-22 | Ｎｔｎ株式会社 | 回転検出装置および回転検出装置付き軸受 |
| GB0520838D0 (en) * | 2005-10-13 | 2005-11-23 | Glaxo Group Ltd | Novel compounds |
| EP1945216A1 (en) | 2005-11-10 | 2008-07-23 | Schering Corporation | Methods for inhibiting protein kinases |
| WO2007058942A2 (en) * | 2005-11-10 | 2007-05-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| JP4837378B2 (ja) | 2006-01-04 | 2011-12-14 | 株式会社日立製作所 | データの改竄を防止する記憶装置 |
| US7446352B2 (en) | 2006-03-09 | 2008-11-04 | Tela Innovations, Inc. | Dynamic array architecture |
| DE102006032495A1 (de) | 2006-07-13 | 2008-02-07 | Nokia Siemens Networks Gmbh & Co.Kg | Verfahren und Vorrichtung zur Vermeidung von Interferenzen in einem zellulären Funkkommunikationssystem |
| US20080025821A1 (en) | 2006-07-25 | 2008-01-31 | Applied Materials, Inc. | Octagon transfer chamber |
| WO2008025821A1 (en) | 2006-08-30 | 2008-03-06 | Cellzome Limited | Triazole derivatives as kinase inhibitors |
| ES2307402B1 (es) | 2006-10-30 | 2009-09-30 | Archivel Farma, S.L. | Vacuna profilactica contra la tuberculosis. |
| US7951818B2 (en) | 2006-12-01 | 2011-05-31 | Galapagos Nv | Imidazolopyridine compounds useful for the treatment of degenerative and inflammatory diseases |
| US7657023B2 (en) | 2007-06-08 | 2010-02-02 | At&T Intellectual Property I, L.P. | Splitter wall plates for digital subscriber line (DSL) communication systems and methods to use the same |
| EP2229390B1 (en) | 2007-12-14 | 2014-04-09 | F. Hoffmann-La Roche AG | Novel imidazoý1,2-a¨pyridine and imidazoý1,2-b¨pyridazine derivatives |
| NZ587039A (en) | 2008-02-13 | 2013-01-25 | Gilead Connecticut Inc | 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof |
| US8338604B2 (en) | 2008-06-20 | 2012-12-25 | Bristol-Myers Squibb Company | Imidazopyridine and imidazopyrazine compounds useful as kinase inhibitors |
| CA2726460C (en) | 2008-07-15 | 2017-02-21 | F. Hoffmann-La Roche Ag | Novel phenyl-imidazopyridines and pyridazines |
| CA2725512C (en) * | 2008-07-18 | 2016-06-28 | F. Hoffmann-La Roche Ag | Novel phenylimidazopyrazines |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| CN104744476B (zh) | 2008-12-08 | 2017-04-12 | 吉利德康涅狄格公司 | 咪唑并吡嗪syk抑制剂 |
| SG171993A1 (en) | 2008-12-08 | 2011-07-28 | Gilead Connecticut Inc | Imidazopyrazine syk inhibitors |
| US20110099133A1 (en) | 2009-10-28 | 2011-04-28 | Industrial Technology Research Institute | Systems and methods for capturing and managing collective social intelligence information |
| NZ602362A (en) | 2010-03-11 | 2014-11-28 | Gilead Connecticut Inc | Imidazopyridines syk inhibitors |
| US20140148430A1 (en) | 2012-11-26 | 2014-05-29 | Gilead Connecticut, Inc. | Imidazopyridines syk inhibitors |
| EP3027171B1 (en) | 2013-07-30 | 2020-03-25 | Gilead Connecticut, Inc. | Formulation of syk inhibitors |
| EA201791873A1 (ru) | 2013-07-30 | 2018-09-28 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| JP6159028B2 (ja) | 2013-07-31 | 2017-07-05 | ギリアード サイエンシーズ， インコーポレイテッド | Ｓｙｋ阻害剤 |
| KR20180002888A (ko) | 2013-12-04 | 2018-01-08 | 길리애드 사이언시즈, 인코포레이티드 | 암을 치료하는 방법 |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| UY35898A (es) | 2013-12-23 | 2015-07-31 | Gilead Sciences Inc | ?compuestos inhibidores de syk y composiciones que los comprenden?. |
| CN106687139A (zh) | 2014-07-14 | 2017-05-17 | 吉利德科学公司 | 用于治疗癌症的组合 |
| TW201617074A (zh) | 2014-07-14 | 2016-05-16 | 吉李德科學股份有限公司 | Ｓｙｋ（脾酪胺酸激酶）抑制劑 |
| TW201639573A (zh) | 2015-02-03 | 2016-11-16 | 吉李德科學股份有限公司 | 有關治療癌症之合併治療 |
| AU2016252387A1 (en) | 2015-04-21 | 2017-10-19 | Gilead Sciences, Inc. | Treatment of chronic graft versus host disease with Syk inhibitors |
| HUE039356T2 (hu) | 2015-07-07 | 2018-12-28 | Swiss Coffee Innovation Ag | Italport tartalmazó kapszula, különösen forrázott kávé készítéséhez |
| TW201822764A (zh) | 2016-09-14 | 2018-07-01 | 美商基利科學股份有限公司 | Syk抑制劑 |
| CA3036384A1 (en) | 2016-09-14 | 2018-03-22 | Gilead Sciences, Inc. | Syk inhibitors |
-
2009
- 2009-12-07 SG SG2011041266A patent/SG171993A1/en unknown
- 2009-12-07 EP EP09832229.0A patent/EP2373318B1/en active Active
- 2009-12-07 EA EA201190043A patent/EA021293B1/ru not_active IP Right Cessation
- 2009-12-07 MX MX2011006094A patent/MX2011006094A/es active IP Right Grant
- 2009-12-07 CN CN201410228824.4A patent/CN104059073B/zh not_active Expired - Fee Related
- 2009-12-07 JP JP2011539525A patent/JP5696052B2/ja not_active Expired - Fee Related
- 2009-12-07 CN CN200980156329.4A patent/CN102307581B/zh not_active Expired - Fee Related
- 2009-12-07 KR KR1020117015710A patent/KR101743784B1/ko not_active Expired - Fee Related
- 2009-12-07 PE PE2011001185A patent/PE20120121A1/es not_active Application Discontinuation
- 2009-12-07 SG SG10201707798SA patent/SG10201707798SA/en unknown
- 2009-12-07 CA CA2745871A patent/CA2745871C/en not_active Expired - Fee Related
- 2009-12-07 US US12/632,151 patent/US8440667B2/en not_active Expired - Fee Related
- 2009-12-07 ES ES09832229T patent/ES2744541T3/es active Active
- 2009-12-07 AU AU2009325133A patent/AU2009325133B2/en not_active Ceased
- 2009-12-07 EP EP19177110.4A patent/EP3552607A3/en not_active Withdrawn
- 2009-12-07 BR BRPI0922226A patent/BRPI0922226A2/pt not_active IP Right Cessation
- 2009-12-07 NZ NZ593460A patent/NZ593460A/xx not_active IP Right Cessation
- 2009-12-07 WO PCT/US2009/006446 patent/WO2010068258A1/en not_active Ceased
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2011
- 2011-06-06 IL IL213405A patent/IL213405A0/en not_active IP Right Cessation
- 2011-06-07 CL CL2011001361A patent/CL2011001361A1/es unknown
- 2011-06-21 CO CO11077859A patent/CO6390109A2/es active IP Right Grant
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2013
- 2013-04-12 US US13/862,147 patent/US8796270B2/en active Active
- 2013-04-12 US US13/862,194 patent/US8962835B2/en active Active
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2014
- 2014-05-22 JP JP2014105805A patent/JP2014148546A/ja not_active Withdrawn
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2015
- 2015-02-23 US US14/629,390 patent/US9567348B2/en not_active Expired - Fee Related
- 2015-12-06 IL IL242955A patent/IL242955A/en not_active IP Right Cessation
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2016
- 2016-05-02 AU AU2016202807A patent/AU2016202807B2/en not_active Ceased
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2017
- 2017-01-11 US US15/404,120 patent/US10093684B2/en active Active
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