JP2015522002A5 - - Google Patents
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- Publication number
- JP2015522002A5 JP2015522002A5 JP2015519416A JP2015519416A JP2015522002A5 JP 2015522002 A5 JP2015522002 A5 JP 2015522002A5 JP 2015519416 A JP2015519416 A JP 2015519416A JP 2015519416 A JP2015519416 A JP 2015519416A JP 2015522002 A5 JP2015522002 A5 JP 2015522002A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyrimidin
- morpholin
- benzonitrile
- pyrimidine
- 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
Links
- -1 5-methyl-1,2,4-oxadiazol-3-yl Chemical group 0.000 claims 29
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- YIDVVQGSCVWPGO-UHFFFAOYSA-N 2-fluoro-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 YIDVVQGSCVWPGO-UHFFFAOYSA-N 0.000 claims 3
- BHTWDJBVZQBRKP-UHFFFAOYSA-N 3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 BHTWDJBVZQBRKP-UHFFFAOYSA-N 0.000 claims 3
- JZYGFRYCZUEFLK-UHFFFAOYSA-N 3-(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCCCC4)N=CN=C3NC=2)=C1 JZYGFRYCZUEFLK-UHFFFAOYSA-N 0.000 claims 3
- PFFIEMXZEROLOA-LBPRGKRZSA-N 3-[4-[(2s)-2-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 PFFIEMXZEROLOA-LBPRGKRZSA-N 0.000 claims 3
- VNWKCLDQBNSJJO-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 VNWKCLDQBNSJJO-UHFFFAOYSA-N 0.000 claims 3
- BDANSBILGUASKD-UHFFFAOYSA-N 4-[5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 BDANSBILGUASKD-UHFFFAOYSA-N 0.000 claims 3
- YISDXRANPXBQIV-UHFFFAOYSA-N 6-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 YISDXRANPXBQIV-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- XTVZGNYXKQQSKT-UHFFFAOYSA-N 1-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound C1=NN(C)C=C1C1=CNC2=NC=NC(N3CC(O)CCC3)=C12 XTVZGNYXKQQSKT-UHFFFAOYSA-N 0.000 claims 2
- IYQTYHISVSPMSU-UHFFFAOYSA-N 1-methyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyrrole-2-carbonitrile Chemical compound C1=C(C#N)N(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 IYQTYHISVSPMSU-UHFFFAOYSA-N 0.000 claims 2
- WXQULZKGDNSDIT-UHFFFAOYSA-N 2-fluoro-3-[4-(3-hydroxypiperidin-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1C(O)CCCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 WXQULZKGDNSDIT-UHFFFAOYSA-N 0.000 claims 2
- WTEXXJFJXIFNLJ-NSHDSACASA-N 2-fluoro-3-[4-[(2s)-2-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 WTEXXJFJXIFNLJ-NSHDSACASA-N 0.000 claims 2
- TYXCXAZJXKGUQS-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 TYXCXAZJXKGUQS-UHFFFAOYSA-N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- WRCUUITXMHZHGJ-UHFFFAOYSA-N 3-(4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCCC4)N=CN=C3NC=2)=C1 WRCUUITXMHZHGJ-UHFFFAOYSA-N 0.000 claims 2
- ZAYWYRLGHFAOON-UHFFFAOYSA-N 3-(6-methyl-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C=12C(C=3C=C(C=CC=3)C#N)=C(C)NC2=NC=NC=1N1CCOCC1 ZAYWYRLGHFAOON-UHFFFAOYSA-N 0.000 claims 2
- JQMHPASIGUDQDB-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-2-fluorobenzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1F JQMHPASIGUDQDB-UHFFFAOYSA-N 0.000 claims 2
- JLOZHIGASXYVKY-UHFFFAOYSA-N 3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(C#N)=C1 JLOZHIGASXYVKY-UHFFFAOYSA-N 0.000 claims 2
- QYEXQVOFWXSVBI-UHFFFAOYSA-N 3-[4-[2-(1h-pyrazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CC(OCC4)C4=NNC=C4)N=CN=C3NC=2)=C1 QYEXQVOFWXSVBI-UHFFFAOYSA-N 0.000 claims 2
- SAOVTENLRUIQAM-UHFFFAOYSA-N 3-[4-[2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=N1 SAOVTENLRUIQAM-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- BISAHRSNHGARQL-UHFFFAOYSA-N 4-(5-imidazo[1,2-b]pyridazin-3-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1N3N=CC=CC3=NC=1)=CN2 BISAHRSNHGARQL-UHFFFAOYSA-N 0.000 claims 2
- XJYBPVJUBUUJKF-UHFFFAOYSA-N 4-[5-(1h-pyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C1=CNN=C1)=CN2 XJYBPVJUBUUJKF-UHFFFAOYSA-N 0.000 claims 2
- IGWCOHZVLMWAFD-UHFFFAOYSA-N 4-[5-(2,3-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1F IGWCOHZVLMWAFD-UHFFFAOYSA-N 0.000 claims 2
- ZWDUUSQSMVRZHV-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ZWDUUSQSMVRZHV-UHFFFAOYSA-N 0.000 claims 2
- ONFLVQULIQDDSN-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound ClC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 ONFLVQULIQDDSN-UHFFFAOYSA-N 0.000 claims 2
- AXVWXYOCYXZGCZ-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 AXVWXYOCYXZGCZ-UHFFFAOYSA-N 0.000 claims 2
- KISKHUBNHHURGR-UHFFFAOYSA-N 4-[5-(3-methyl-1,2-thiazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound S1N=C(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 KISKHUBNHHURGR-UHFFFAOYSA-N 0.000 claims 2
- WLBWMAISCIFWAN-UHFFFAOYSA-N 4-[5-(5-bromopyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound BrC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 WLBWMAISCIFWAN-UHFFFAOYSA-N 0.000 claims 2
- JWNOQCCPFZXUTN-UHFFFAOYSA-N 4-[5-(5-chloro-2-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=C(Cl)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 JWNOQCCPFZXUTN-UHFFFAOYSA-N 0.000 claims 2
- QPWYSUWXPGZSOH-UHFFFAOYSA-N 4-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CN=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QPWYSUWXPGZSOH-UHFFFAOYSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- CZUHAOMXATZIIC-SNVBAGLBSA-N (2r)-2-methyl-4-[5-(1-methylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CO[C@H](C)CN1C1=NC=NC2=C1C(C1=CN(C)N=C1)=CN2 CZUHAOMXATZIIC-SNVBAGLBSA-N 0.000 claims 1
- FXWRFSPVQWGHIR-LBPRGKRZSA-N (2s)-2-methyl-4-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(C)C=NC=1)=CN2 FXWRFSPVQWGHIR-LBPRGKRZSA-N 0.000 claims 1
- VGTLBPASJCZAFD-LBPRGKRZSA-N (2s)-4-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3C[C@H](C)OCC3)=C12 VGTLBPASJCZAFD-LBPRGKRZSA-N 0.000 claims 1
- WZOCVLIZBXKCIZ-NSHDSACASA-N (2s)-4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound C1CO[C@@H](C)CN1C1=NC=NC2=C1C(C=1C=C(F)C=CC=1)=CN2 WZOCVLIZBXKCIZ-NSHDSACASA-N 0.000 claims 1
- ZFXOQGPDYHYOLS-NSHDSACASA-N (2s)-4-[5-(5-fluoro-2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylmorpholine Chemical compound COC1=CC=C(F)C=C1C1=CNC2=NC=NC(N3C[C@H](C)OCC3)=C12 ZFXOQGPDYHYOLS-NSHDSACASA-N 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- XUDFUERXQXOOMM-UHFFFAOYSA-N 1,5-dimethyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)pyrrole-2-carbonitrile Chemical compound C1=C(C#N)N(C)C(C)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 XUDFUERXQXOOMM-UHFFFAOYSA-N 0.000 claims 1
- SWBMTULEVBPEDZ-UHFFFAOYSA-N 1-(5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 SWBMTULEVBPEDZ-UHFFFAOYSA-N 0.000 claims 1
- PLQIAEXRNLFVCU-UHFFFAOYSA-N 1-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CC(O)CCC3)=C12 PLQIAEXRNLFVCU-UHFFFAOYSA-N 0.000 claims 1
- KJJOMGASMNZRSR-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound C1C(C#N)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 KJJOMGASMNZRSR-UHFFFAOYSA-N 0.000 claims 1
- FFFVFLJBIVJUEA-UHFFFAOYSA-N 1-[5-(3-cyanophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 FFFVFLJBIVJUEA-UHFFFAOYSA-N 0.000 claims 1
- MRABRFBCPPKJLC-UHFFFAOYSA-N 1-[5-(3-fluoro-5-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound COC1=CC(F)=CC(C=2C3=C(N4CC(O)CCC4)N=CN=C3NC=2)=C1 MRABRFBCPPKJLC-UHFFFAOYSA-N 0.000 claims 1
- BEHWSSWEKOLCEQ-UHFFFAOYSA-N 1-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=NC=NC2=C1C(C=1C=C(F)C=CC=1)=CN2 BEHWSSWEKOLCEQ-UHFFFAOYSA-N 0.000 claims 1
- PQXAADSTABWHNC-UHFFFAOYSA-N 1-[5-(5-methylpyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-3-ol Chemical compound CC1=CN=CC(C=2C3=C(N4CC(O)CCC4)N=CN=C3NC=2)=C1 PQXAADSTABWHNC-UHFFFAOYSA-N 0.000 claims 1
- OAGXISWXYQYLEZ-UHFFFAOYSA-N 1-[5-[3-(hydroxymethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound OCC1=CC=CC(C=2C3=C(N4CC(CCC4)C#N)N=CN=C3NC=2)=C1 OAGXISWXYQYLEZ-UHFFFAOYSA-N 0.000 claims 1
- OZNNCYFDQWZWPW-UHFFFAOYSA-N 1-methyl-4-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)imidazole-2-carbonitrile Chemical compound N1=C(C#N)N(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 OZNNCYFDQWZWPW-UHFFFAOYSA-N 0.000 claims 1
- LXODCZJCWAAMGA-UHFFFAOYSA-N 2-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 LXODCZJCWAAMGA-UHFFFAOYSA-N 0.000 claims 1
- AFVZXTFKZIXUDK-UHFFFAOYSA-N 2-fluoro-3-(2-methyl-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C=12C(C=3C(=C(C#N)C=CC=3)F)=CNC2=NC(C)=NC=1N1CCOCC1 AFVZXTFKZIXUDK-UHFFFAOYSA-N 0.000 claims 1
- QYKISUPBXOHKOJ-UHFFFAOYSA-N 2-fluoro-3-(4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCCC3)=C12 QYKISUPBXOHKOJ-UHFFFAOYSA-N 0.000 claims 1
- GTPYPGWTKZAMCX-OAHLLOKOSA-N 2-fluoro-3-[4-[(2r)-2-(3-methyl-1,2,4-oxadiazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound CC1=NOC([C@@H]2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-OAHLLOKOSA-N 0.000 claims 1
- GTPYPGWTKZAMCX-HNNXBMFYSA-N 2-fluoro-3-[4-[(2s)-2-(3-methyl-1,2,4-oxadiazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound CC1=NOC([C@H]2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-HNNXBMFYSA-N 0.000 claims 1
- ZRJIYGGDPFWFFW-NSHDSACASA-N 2-fluoro-3-[4-[(3s)-3-fluoropyrrolidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](F)CCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 ZRJIYGGDPFWFFW-NSHDSACASA-N 0.000 claims 1
- IGANZPRDUTWWRQ-LBPRGKRZSA-N 2-fluoro-3-[4-[(3s)-3-methylpiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1[C@@H](C)CCCN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 IGANZPRDUTWWRQ-LBPRGKRZSA-N 0.000 claims 1
- GTPYPGWTKZAMCX-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound CC1=NOC(C2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-UHFFFAOYSA-N 0.000 claims 1
- ZKHFKYILMCNJCH-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(methoxymethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(COC)CN1C1=NC=NC2=C1C(C=1C(=C(C#N)C=CC=1)F)=CN2 ZKHFKYILMCNJCH-UHFFFAOYSA-N 0.000 claims 1
- PPBWDPPUKPVDQL-UHFFFAOYSA-N 2-methyl-3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound CC1=C(C#N)C=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 PPBWDPPUKPVDQL-UHFFFAOYSA-N 0.000 claims 1
- LAEVHNHECWJRFL-UHFFFAOYSA-N 2-methyl-5-(4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)pyrazole-3-carbonitrile Chemical compound C1=C(C#N)N(C)N=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 LAEVHNHECWJRFL-UHFFFAOYSA-N 0.000 claims 1
- XTIGQBGLUHGYQF-UHFFFAOYSA-N 3-(2-methyl-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound C=12C(C=3C=C(C=CC=3)C#N)=CNC2=NC(C)=NC=1N1CCOCC1 XTIGQBGLUHGYQF-UHFFFAOYSA-N 0.000 claims 1
- IXICFQPOLVNLBK-UHFFFAOYSA-N 3-[4-(1h-pyrazol-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(NC4=CNN=C4)N=CN=C3NC=2)=C1 IXICFQPOLVNLBK-UHFFFAOYSA-N 0.000 claims 1
- RFDOWEJYIPXXRM-UHFFFAOYSA-N 3-[4-(2,2-dimethylmorpholin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(C)(C)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 RFDOWEJYIPXXRM-UHFFFAOYSA-N 0.000 claims 1
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- QYMXFRIVGZZMAD-UHFFFAOYSA-N 3-[4-[2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(CC2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=N1 QYMXFRIVGZZMAD-UHFFFAOYSA-N 0.000 claims 1
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| EP2827869A4 (en) | 2012-03-23 | 2015-09-23 | Dennis Brown | COMPOSITIONS AND METHODS FOR IMPROVING THE THERAPEUTIC BENEFIT OF INDIRUBIN AND ANALOGUE THEREOF, WITH MEISOINDIGO |
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| US8963597B1 (en) * | 2013-10-02 | 2015-02-24 | Nanya Technology Corporation | Cross-domain enablement method and electronic apparatus |
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| US9815841B2 (en) | 2014-01-29 | 2017-11-14 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
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| US10058559B2 (en) | 2014-05-15 | 2018-08-28 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Treatment or prevention of an intestinal disease or disorder |
| CN104086553B (zh) * | 2014-06-13 | 2016-04-27 | 南京药石科技股份有限公司 | 一种制备7-溴咪唑并[2,1-f][1,2,4]三嗪-4-胺的方法 |
| US10004751B2 (en) | 2014-07-10 | 2018-06-26 | The J. David Gladstone Institutes | Compositions and methods for treating Dengue virus infection |
| PL3218378T3 (pl) | 2014-11-14 | 2020-10-19 | Nerviano Medical Sciences S.R.L. | Pochodne 6-amino-7-bicyklo-7-deazapuryny jako inhibitory kinaz białkowych |
| RU2722149C1 (ru) | 2015-09-14 | 2020-05-27 | Пфайзер Инк. | Новые производные имидазо[4,5-c] хинолинов и имидазо[4,5-c][1,5] нафтиридинов в качестве ингибиторов LRRK2 |
| FR3041640B1 (fr) * | 2015-09-30 | 2019-05-17 | Les Laboratoires Servier | NOUVEAUX DERIVES DE PYRROLO[2,3-d]PYRIMIDINE, LEUR PROCEDE DE PREPRATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
| AR107032A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores bicíclicos de pad4 |
| JP2019534266A (ja) | 2016-10-14 | 2019-11-28 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ５員ヘテロアリール環の架橋した環誘導体、その製造方法およびその医学的使用 |
| JP7101176B2 (ja) * | 2017-02-03 | 2022-07-14 | レオ ファーマ アクティーゼルスカブ | 新規ＪＡＫキナーゼ阻害剤としての５－（７Ｈ－ピロロ［２，３－ｄ］ピリミジン－４－イル）－５－アザスピロ［２．５］オクタン－８－カルボン酸誘導体 |
| CN106831790B (zh) * | 2017-02-17 | 2019-07-26 | 四川大学华西医院 | 7H-吡咯并[2,3-d]嘧啶衍生物 |
| WO2018155947A1 (ko) | 2017-02-24 | 2018-08-30 | 재단법인 대구경북첨단의료산업진흥재단 | 혈액 뇌관문을 통과할 수 있는 화합물을 유효성분으로 함유하는 뇌암의 예방 또는 치료용 약학적 조성물 |
| KR20190131981A (ko) * | 2018-05-18 | 2019-11-27 | 재단법인 대구경북첨단의료산업진흥재단 | 외상성 뇌손상 또는 뇌졸중의 예방 또는 치료용 약학적 조성물 |
| KR101990739B1 (ko) * | 2018-07-24 | 2019-06-19 | 재단법인 대구경북첨단의료산업진흥재단 | 혈액 뇌관문을 통과할 수 있는 화합물을 유효성분으로 함유하는 뇌암의 예방 또는 치료용 약학적 조성물 |
| WO2020040591A1 (ko) * | 2018-08-23 | 2020-02-27 | 재단법인 대구경북첨단의료산업진흥재단 | Lrrk 키나아제 저해제를 유효성분으로 함유하는 피리미딘 유도체의 신규용도 |
| KR101992059B1 (ko) * | 2018-08-23 | 2019-06-21 | 재단법인 대구경북첨단의료산업진흥재단 | 혈액 뇌관문을 통과할 수 있는 화합물을 유효성분으로 함유하는 뇌암의 예방 또는 치료용 약학적 조성물 |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| US12398140B2 (en) | 2019-02-13 | 2025-08-26 | Ptc Therapeutics, Inc. | Substituted pyrrolo [2,3-d]pyrimidines for treating familial dysautonomia |
| MX2021009667A (es) | 2019-02-13 | 2021-12-10 | Ptc Therapeutics Inc | Compuestos de tioeno[3,2-b] piridin-7-amina para tratar la disautonomía familiar. |
| CN114269734A (zh) | 2019-05-08 | 2022-04-01 | 维玛兰生物科学公司 | Jak抑制剂 |
| TW202122400A (zh) | 2019-08-08 | 2021-06-16 | 美商維瑪蘭生物科學公司 | Jak抑制劑 |
| CN115003300A (zh) * | 2019-09-25 | 2022-09-02 | 维玛兰生物科学公司 | Jak抑制剂 |
| WO2021170540A1 (en) * | 2020-02-25 | 2021-09-02 | Vib Vzw | Leucine-rich repeat kinase 2 allosteric modulators |
| CN111671757A (zh) * | 2020-07-16 | 2020-09-18 | 福建医科大学附属协和医院 | 3-[4-（4-吗啉基）-7h-吡咯并[2,3-d]嘧啶-5-基]苯甲腈制药用途 |
| CA3190782A1 (en) * | 2020-10-20 | 2022-04-28 | F. Hoffmann-La Roche Ag | Combination therapy of pd-1 axis binding antagonists and lrrk2 inhibitors |
| JP2023549294A (ja) * | 2020-10-26 | 2023-11-22 | ニューロン２３， インコーポレイテッド | 野生型ｌｒｒｋ２に関連するパーキンソン病の処置および診断方法 |
| IL308184A (en) * | 2021-05-05 | 2024-01-01 | Kare Chemical Tech Inc | Processes for the preparation of catalytic tryptamines and starting materials |
| US20240382491A1 (en) * | 2021-09-07 | 2024-11-21 | Ptc Therapeutics, Inc. | Methods for treating neurogenerative diseases |
| WO2023055731A1 (en) * | 2021-09-28 | 2023-04-06 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of serine/threonine protein kinase stk3 or stk4 and uses thereof |
| WO2023073013A1 (en) | 2021-10-27 | 2023-05-04 | H. Lundbeck A/S | Lrrk2 inhibitors |
| WO2023076404A1 (en) | 2021-10-27 | 2023-05-04 | Aria Pharmaceuticals, Inc. | Methods for treating systemic lupus erythematosus |
| TW202412777A (zh) | 2022-09-15 | 2024-04-01 | 丹麥商Ｈ 朗德貝克公司 | 富白胺酸重複激酶2（lrrk2）抑制劑 |
| WO2025019585A1 (en) * | 2023-07-17 | 2025-01-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Kinase inhibitors |
| KR102847381B1 (ko) * | 2024-02-07 | 2025-08-19 | 노보렉스 주식회사 | Lrrk2 단백질 키나제 도메인 억제제로서 신규한 화합물 |
| WO2025170397A1 (ko) * | 2024-02-07 | 2025-08-14 | 노보렉스 주식회사 | Lrrk2 단백질 키나제 도메인 억제제로서 신규한 화합물 |
Family Cites Families (184)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| JP2890448B2 (ja) | 1988-04-26 | 1999-05-17 | 日産化学工業株式会社 | ピラゾロピリジン系メバロノラクトン類 |
| US5658889A (en) | 1989-01-24 | 1997-08-19 | Gensia Pharmaceuticals, Inc. | Method and compounds for aica riboside delivery and for lowering blood glucose |
| CA2011504C (en) | 1989-03-07 | 1998-06-02 | Kenji Ohmori | Imidazoquinolone derivatives |
| US5795977A (en) | 1989-09-15 | 1998-08-18 | Metabasis Therapeutics, Inc. | Water soluble adenosine kinase inhibitors |
| US5864033A (en) | 1989-09-15 | 1999-01-26 | Metabasis Therapeutics, Inc. | Adenosine kinase inhibitors |
| US5763597A (en) | 1989-09-15 | 1998-06-09 | Metabasis Therapeutics, Inc. | Orally active adenosine kinase inhibitors |
| US5646128A (en) | 1989-09-15 | 1997-07-08 | Gensia, Inc. | Methods for treating adenosine kinase related conditions |
| US5726302A (en) | 1989-09-15 | 1998-03-10 | Gensia Inc. | Water soluble adenosine kinase inhibitors |
| US5674998A (en) | 1989-09-15 | 1997-10-07 | Gensia Inc. | C-4' modified adenosine kinase inhibitors |
| US5721356A (en) * | 1989-09-15 | 1998-02-24 | Gensia, Inc. | Orally active adenosine kinase inhibitors |
| US5763596A (en) | 1989-09-15 | 1998-06-09 | Metabasis Therapeutics, Inc. | C-4' modified adenosine kinase inhibitors |
| JPH03271289A (ja) | 1990-03-16 | 1991-12-03 | Nissan Chem Ind Ltd | ピラゾロピリジン誘導体の製造法及びジヒドロピラゾロピリジン誘導体 |
| US5389640A (en) | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| JP3130342B2 (ja) | 1991-10-04 | 2001-01-31 | 日産化学工業株式会社 | 動脈硬化性血管内膜肥厚抑制薬 |
| JP3271289B2 (ja) | 1992-02-28 | 2002-04-02 | スズキ株式会社 | ４サイクルエンジンのバルブ駆動装置 |
| US5502187A (en) | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| AU675932B2 (en) | 1992-04-03 | 1997-02-27 | Pharmacia & Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| WO1995011898A1 (en) | 1992-05-12 | 1995-05-04 | Nissan Chemical Industries Ltd. | Condensed pyridine type mevalonolactone intermediate and process for its production |
| JPH05310700A (ja) | 1992-05-12 | 1993-11-22 | Sagami Chem Res Center | 縮合ピリジン系メバロノラクトン中間体及びその製法 |
| JPH0641114A (ja) | 1992-05-25 | 1994-02-15 | Nissan Chem Ind Ltd | 新規メバロノラクトン類とその製法 |
| JPH06116239A (ja) | 1992-10-05 | 1994-04-26 | Nissan Chem Ind Ltd | ７−置換−３，５−ジヒドロキシヘプタ−６−イン酸類 |
| BR9307264A (pt) | 1992-10-16 | 1999-05-11 | Nippon Soda Co | Derivados de pirimidina herbicida e fungicida |
| US5750349A (en) | 1993-01-25 | 1998-05-12 | Takeda Chemical Industries Ltd. | Antibodies to β-amyloids or their derivatives and use thereof |
| WO1994018215A1 (en) | 1993-02-03 | 1994-08-18 | Gensia, Inc. | Adenosine kinase inhibitors comprising lyxofuranosyl derivatives |
| DE4304455A1 (de) | 1993-02-15 | 1994-08-18 | Bayer Ag | Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate |
| JP3119758B2 (ja) | 1993-02-24 | 2000-12-25 | 日清製粉株式会社 | ７−アザインドール誘導体及びこれを有効成分とする抗潰瘍薬 |
| JP3350739B2 (ja) | 1993-06-10 | 2002-11-25 | コニカ株式会社 | 黒白ハロゲン化銀写真感光材料の現像処理方法 |
| CN1102644A (zh) | 1993-11-11 | 1995-05-17 | 财团法人相模中央化学研究所 | 缩合吡啶型甲羟戊酸内酯中间体及其制备方法 |
| JPH07281365A (ja) | 1994-04-07 | 1995-10-27 | Konica Corp | 写真感光材料の処理方法 |
| ATE159257T1 (de) | 1994-05-03 | 1997-11-15 | Ciba Geigy Ag | Pyrrolopyrimidinderivate mit antiproliferativer wirkung |
| JP3448724B2 (ja) | 1995-11-29 | 2003-09-22 | コニカ株式会社 | ハロゲン化銀写真感光材料用現像剤及びその処理方法 |
| GB9604361D0 (en) | 1996-02-29 | 1996-05-01 | Pharmacia Spa | 4-Substituted pyrrolopyrimidine compounds as tyrosine kinase inhibitors |
| BR9709443B1 (pt) * | 1996-03-15 | 2009-05-05 | n-7-heterociclil-pirrol[2,3-d]pirimidinas, bem como composições farmacêuticas compreendendo as mesmas. | |
| JPH10213887A (ja) | 1996-11-26 | 1998-08-11 | Konica Corp | 黒白ハロゲン化銀写真感光材料の処理方法 |
| KR20000057228A (ko) * | 1996-11-27 | 2000-09-15 | 디. 제이. 우드, 스피겔 알렌 제이 | 축합된 비사이클릭 피리미딘 유도체 |
| EP0846981A1 (en) | 1996-12-03 | 1998-06-10 | Konica Corporation | Method for processing black-and-white silver halide photographic light-sensitive material |
| JP3543249B2 (ja) | 1996-12-18 | 2004-07-14 | コニカミノルタホールディングス株式会社 | 黒白ハロゲン化銀写真感光材料の処理方法 |
| US8173127B2 (en) | 1997-04-09 | 2012-05-08 | Intellect Neurosciences, Inc. | Specific antibodies to amyloid beta peptide, pharmaceutical compositions and methods of use thereof |
| AU743827B2 (en) | 1997-04-09 | 2002-02-07 | Intellect Neurosciences, Inc. | Recombinant antibodies specific for beta-amyloid ends, DNA encoding and methods of use thereof |
| US6905686B1 (en) | 1997-12-02 | 2005-06-14 | Neuralab Limited | Active immunization for treatment of alzheimer's disease |
| TWI239847B (en) | 1997-12-02 | 2005-09-21 | Elan Pharm Inc | N-terminal fragment of Abeta peptide and an adjuvant for preventing and treating amyloidogenic disease |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| CZ20004727A3 (cs) | 1998-06-19 | 2002-03-13 | Pfizer Products Inc. | Deriváty pyrrolo[2,3-d] pyrimidinu |
| YU25500A (sh) | 1999-05-11 | 2003-08-29 | Pfizer Products Inc. | Postupak za sintezu analoga nukleozida |
| US6309811B2 (en) | 1999-07-21 | 2001-10-30 | Eastman Kodak Company | Color photographic element containing nitrogen heterocycle derivative and inhibitor releasing coupler |
| SK288711B6 (sk) | 2000-02-24 | 2019-11-05 | Univ Washington | Humanizovaná protilátka, jej fragment a ich použitie, polynukleová kyselina, expresný vektor, bunka a farmaceutický prostriedok |
| JP2001302515A (ja) | 2000-04-18 | 2001-10-31 | Sumitomo Pharmaceut Co Ltd | ポリ（ａｄｐ−リボース）ポリメラーゼ阻害剤 |
| WO2001098301A1 (en) | 2000-06-20 | 2001-12-27 | Japan Tobacco Inc. | Pyrazolopyridine compounds and use thereof as drugs |
| CA2427661C (en) | 2000-11-03 | 2013-05-28 | Proteotech, Inc. | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
| DK1355904T3 (da) | 2000-12-22 | 2007-10-15 | Wyeth Corp | Heterocyclindazol- og -azaindazolforbindelser som 5-hydroxytryptamin-6-ligander |
| GB0111186D0 (en) | 2001-05-08 | 2001-06-27 | Smithkline Beecham Plc | Novel compounds |
| US20030114467A1 (en) * | 2001-06-21 | 2003-06-19 | Shakespeare William C. | Novel pyrazolo- and pyrrolo-pyrimidines and uses thereof |
| EP1432444A4 (en) | 2001-08-17 | 2005-11-02 | Lilly Co Eli | ANTI-BETA ANTIBODIES |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| AU2002339230A1 (en) | 2002-03-08 | 2003-09-22 | Decode Genetics Ehf. | A susceptibility gene for late-onset idiopathic parkinson's disease |
| WO2004014368A1 (en) | 2002-08-12 | 2004-02-19 | Sugen, Inc. | 3-pyrrolyl-pyridopyrazoles and 3-pyrrolyl-indazoles as novel kinase inhibitors |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| JP2006519762A (ja) | 2002-10-09 | 2006-08-31 | ライナット ニューロサイエンス コーポレイション | アミロイドβペプチド及びその組成物に対する抗体を使用して、アルツハイマー病を治療する方法 |
| DE10259382A1 (de) | 2002-12-18 | 2004-07-01 | Abbott Gmbh & Co. Kg | 3-Substituierte 3,4-Dihydro-thieno[2,3-d]pyrimidin-4-on-Derivate, ihre Herstellung und Verwendung |
| US20040220186A1 (en) | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| MXPA05013770A (es) | 2003-06-19 | 2006-03-08 | Pfizer Prod Inc | Antagonista de neuroquinina 1. |
| WO2005044181A2 (en) | 2003-09-09 | 2005-05-19 | Temple University-Of The Commonwealth System Of Higher Education | Protection of tissues and cells from cytotoxic effects of ionizing radiation by abl inhibitors |
| US20070031416A1 (en) | 2003-09-09 | 2007-02-08 | Takeda Pharmaceutical Company Limited | Use of antibody |
| CN1925855B (zh) | 2003-12-19 | 2010-06-16 | 普莱希科公司 | 开发Ret调节剂的化合物和方法 |
| US20050165029A1 (en) * | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| WO2005080361A1 (en) | 2004-02-02 | 2005-09-01 | Pfizer Products Inc. | Histamine-3 receptor modulators |
| CA2561628C (en) | 2004-04-01 | 2012-05-08 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| EP1756108A2 (en) | 2004-04-02 | 2007-02-28 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of rock and other protein kinases |
| US7456164B2 (en) | 2004-05-07 | 2008-11-25 | Pfizer, Inc | 3- or 4-monosubtituted phenol and thiophenol derivatives useful as H3 ligands |
| EP1595881A1 (en) | 2004-05-12 | 2005-11-16 | Pfizer Limited | Tetrahydronaphthyridine derivates useful as histamine H3 receptor ligands |
| BRPI0510273A (pt) | 2004-05-25 | 2007-10-30 | Pfizer Prod Inc | derivados de tetraazabenzo[e]azuleno e análogos destes |
| WO2005121175A2 (en) | 2004-06-08 | 2005-12-22 | Novartis Vaccines And Diagnostics Inc. | Env polypeptide complexes and methods of use |
| CA2572314A1 (en) | 2004-06-29 | 2006-01-12 | Christopher N. Farthing | Pyrrolo[2,3-d]pyrimidines that modulate ack1 and lck activity |
| BRPI0513959A (pt) | 2004-07-30 | 2008-05-20 | Rinat Neuroscience Corp | anticorpos dirigidos contra o peptìdeo beta-amilóide, suas composições farmacêuticas, kit e métodos de fabricação dos mesmos |
| WO2006042102A2 (en) | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| WO2006045392A2 (en) | 2004-10-21 | 2006-05-04 | GSF-Forschungszentrum für Umwelt und Gesundheit GmbH | Kaspp (lrrke) gene, its production and use for the detection and treatment of neurodegenerative disorders |
| WO2006052568A2 (en) | 2004-11-10 | 2006-05-18 | Eli Lilly And Company | Tgf-beta inhibitors |
| DE102004054634A1 (de) | 2004-11-12 | 2006-05-18 | Schwarz Pharma Ag | Azaindolcarboxamide |
| EP1827493A4 (en) | 2004-12-22 | 2009-09-30 | Univ St Louis | USE OF ANTI-ABETA ANTIBODIES FOR THE TREATMENT OF BRAIN TRAUMA |
| EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| UY29504A1 (es) | 2005-04-29 | 2006-10-31 | Rinat Neuroscience Corp | Anticuerpos dirigidos contra el péptido amiloide beta y métodos que utilizan los mismos. |
| ES2354569T3 (es) | 2005-06-22 | 2011-03-16 | Pfizer Products Inc. | Antagonistas del receptor de histamina-3. |
| US8158673B2 (en) | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| EP1945639A1 (en) | 2005-11-04 | 2008-07-23 | Pfizer Limited | Tetrahydronaphthyridine derivative |
| WO2007063385A2 (en) | 2005-12-01 | 2007-06-07 | Pfizer Products Inc. | Spirocyclic amine histamine-3 receptor antagonists |
| WO2007069053A1 (en) | 2005-12-14 | 2007-06-21 | Pfizer Products Inc. | Benzimidazole antagonists of the h-3 receptor |
| EP1968568A4 (en) | 2005-12-22 | 2011-04-13 | Glaxosmithkline Llc | HEMMER OF NUTS ACTIVITY |
| KR20080083680A (ko) | 2005-12-23 | 2008-09-18 | 스미스클라인 비참 코포레이션 | 오로라 키나제의 아자인돌 억제제 |
| WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
| WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| US20090163482A1 (en) | 2006-03-13 | 2009-06-25 | Mchardy Stanton Furst | Tetralines antagonists of the h-3 receptor |
| JP2009529860A (ja) | 2006-03-14 | 2009-08-27 | セルゾーム・アクチェンゲゼルシャフト | Ｌｒｒｋ２が相互作用する分子の同定およびｌｒｒｋ２の精製のための方法 |
| WO2007124096A2 (en) | 2006-04-21 | 2007-11-01 | The Trustees Of Columbia University In The City Of New York | Lrrk2 regulaton of neuronal process morphology |
| GB0610317D0 (en) | 2006-05-24 | 2006-07-05 | Medical Res Council | Antiparasitic compounds and compositions |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| BRPI0713738A2 (pt) * | 2006-06-20 | 2014-06-24 | Novartis Ag | Biomarcadores para a progressão de doença alzheimer |
| AU2007332143B2 (en) | 2006-12-11 | 2012-11-08 | Bionomics Limited | Chemical compounds and processes |
| WO2008075007A1 (en) * | 2006-12-21 | 2008-06-26 | Cancer Research Technology Limited | Morpholino-substituted bicycloheteroaryl compounds and their use as anti cancer agents |
| WO2008091799A2 (en) | 2007-01-22 | 2008-07-31 | The Trustees Of Columbia University In The City Of New York | Cell-based methods for identifying inhibitors of parkinson's disease-associated lrrk2 mutants |
| KR101108109B1 (ko) | 2007-01-22 | 2012-02-06 | 화이자 프로덕츠 인코포레이티드 | 치료 화합물의 토실레이트 염 및 이의 약학 조성물 |
| FR2912744B1 (fr) | 2007-02-16 | 2012-09-07 | Centre Nat Rech Scient | Composes pyrrolo°2,3-b!pyridine,composes azaindoles utiles dans la synthese de ces composes pyrrolo°2,3-b!pyridine, leurs procedes de fabrication et leurs utilisations. |
| GB0706709D0 (en) | 2007-04-05 | 2007-05-16 | Medical Res Council | Methods |
| US7998966B2 (en) | 2007-04-13 | 2011-08-16 | Supergen, Inc. | Axl kinase inhibitors |
| AU2008249750B2 (en) | 2007-05-11 | 2011-07-14 | Pfizer Inc. | Amino-heterocyclic compounds |
| CL2008001540A1 (es) | 2007-05-29 | 2009-05-22 | Sgx Pharmaceuticals Inc | Compuestos derivados de pirrolopiridinas y pirazolopiridinas; composicion farmaceutica; y uso en el tratamiento del cancer. |
| DE102007028515A1 (de) | 2007-06-21 | 2008-12-24 | Merck Patent Gmbh | 6-(Pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate |
| WO2009000319A1 (de) | 2007-06-22 | 2008-12-31 | Schulz Hans M | Handeingabegerät |
| WO2009005730A1 (en) | 2007-06-27 | 2009-01-08 | Cornell University | Transgenic animal models of parkinson's disease |
| WO2009030270A1 (en) | 2007-09-03 | 2009-03-12 | Novartis Ag | Dihydroindole derivatives useful in parkinson's disease |
| AR068438A1 (es) | 2007-09-14 | 2009-11-18 | Mitsubishi Tanabe Pharma Corp | Derivado de 6-pirimidinil-pirimid-2-ona |
| US20090118276A1 (en) | 2007-11-02 | 2009-05-07 | Wyeth | Thienopyrimidines, thienopyridines, and pyrrolopyrimidines as b-raf inhibitors |
| WO2009071620A1 (en) | 2007-12-05 | 2009-06-11 | Johannes Gutenberg-Universität Mainz | Use of 3-(indolyl)- or 3-(azaindolyl)-4-arylmaleimide derivatives in leukemia management |
| WO2009127642A2 (en) | 2008-04-15 | 2009-10-22 | Cellzome Limited | Use of lrrk2 inhibitors for neurodegenerative diseases |
| WO2009131687A2 (en) | 2008-04-22 | 2009-10-29 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| CA2722220C (en) | 2008-04-30 | 2016-06-07 | National Health Research Institutes | Fused bicyclic pyrimidine compounds as aurora kinase inhibitors |
| DE102008025751A1 (de) | 2008-05-29 | 2009-12-03 | Merck Patent Gmbh | 4-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-pyridin-2-ylamin-derivate |
| AR072008A1 (es) | 2008-06-13 | 2010-07-28 | Merck & Co Inc | Compuestos heterobiciclicos como agentes de inhibicion de quinasa p38 |
| JP2011526931A (ja) * | 2008-07-03 | 2011-10-20 | エグゼリクシス， インコーポレイテッド | Ｃｄｋモジュレーター |
| DE102008031517A1 (de) | 2008-07-03 | 2010-01-07 | Merck Patent Gmbh | Pyrrolopyridinyl-pyrimidin-2-yl-amin-derivate |
| DE102008038221A1 (de) | 2008-08-18 | 2010-02-25 | Merck Patent Gmbh | 7-Azaindolderivate |
| FR2935712A1 (fr) | 2008-09-05 | 2010-03-12 | Ct Hospitalier Regional Univer | Methode de detection de l'expression differentielle d'un ensemble de marqueurs moleculaires associee a la maladie de parkinson |
| GB2463656B (en) | 2008-09-18 | 2010-10-13 | Medical Res Council | Substrate of LRRK2 and methods of assessing LRRK2 activity |
| CA2738429C (en) | 2008-09-26 | 2016-10-25 | Intellikine, Inc. | Heterocyclic kinase inhibitors |
| US20100175140A1 (en) | 2008-12-19 | 2010-07-08 | The Johns Hopkins University | Leucine-rich repeat kinase (LRRK2) drosophila model for parkinson's disease: wildtype1 (WT1) and G2019S mutant flies |
| EP2379559B1 (en) | 2009-01-06 | 2017-10-25 | Dana-Farber Cancer Institute, Inc. | Pyrimido-diazepinone kinase scaffold compounds and methods of treating disorders |
| EP2210887A1 (en) | 2009-01-14 | 2010-07-28 | Isdin, S.A. | Bis resorcinyl triazine derivatives as protecting agents against UV radiation |
| WO2010085799A2 (en) | 2009-01-26 | 2010-07-29 | Tautatis, Inc. | Compositions and method for the treatment of parkinson's disease |
| WO2010093191A2 (en) | 2009-02-13 | 2010-08-19 | Lg Life Sciences Ltd. | Novel compounds effective as xanthine oxidase inhibitors, method for preparing the same, and pharmaceutical composition containing the same |
| KR101700229B1 (ko) * | 2009-03-19 | 2017-01-26 | 메디칼 리서치 카운실 테크놀로지 | 화합물들 |
| TW201040191A (en) | 2009-03-27 | 2010-11-16 | Abbott Gmbh & Co Kg | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| KR20100116765A (ko) | 2009-04-23 | 2010-11-02 | 인제대학교 산학협력단 | 파킨슨병 치료제 스크리닝 방법 |
| DE102009019962A1 (de) | 2009-05-05 | 2010-11-11 | Merck Patent Gmbh | 3-([1,2,3]Triazol-4-yl)-pyrrolo[2,3-b]pyridinderivate |
| US9908884B2 (en) | 2009-05-05 | 2018-03-06 | Dana-Farber Cancer Institute, Inc. | EGFR inhibitors and methods of treating disorders |
| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| BR112012006859A2 (pt) | 2009-09-29 | 2019-09-24 | Glaxo Group Ltd | compostos |
| FR2951172B1 (fr) | 2009-10-13 | 2014-09-26 | Pf Medicament | Derives pyrazolopyridines en tant qu'agent anticancereux |
| ES2658290T3 (es) | 2009-10-29 | 2018-03-09 | Genosco | Inhibidores de cinasa |
| KR20110049217A (ko) | 2009-11-04 | 2011-05-12 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
| WO2011057204A2 (en) * | 2009-11-06 | 2011-05-12 | The Johns Hopkins University | Lrrk2-mediated neuronal toxicity |
| EP2498607B1 (en) | 2009-11-13 | 2016-02-17 | Genosco | Kinase inhibitors |
| EP2338486A1 (en) | 2009-12-18 | 2011-06-29 | Johannes Gutenberg-Universität Mainz | 3-(indolyl)- or 3-(azaindolyl)-4-arylmaleimide derivatives for use in the treatment of colon and gastric adenocarcinoma |
| CN102821607B (zh) | 2009-12-21 | 2014-12-17 | 萨穆梅德有限公司 | 1H-吡唑并[3，4-b]吡啶及其治疗应用 |
| WO2011106168A1 (en) | 2010-02-24 | 2011-09-01 | Dcam Pharma Inc | Purine compounds for treating autoimmune and demyelinating diseases |
| US8367349B2 (en) | 2010-04-19 | 2013-02-05 | Medical Research Council | Methods for identifying modulators of LRRK2 |
| WO2011137022A1 (en) | 2010-04-27 | 2011-11-03 | Merck Sharp & Dohme Corp. | Azaindoles as janus kinase inhibitors |
| GB201008134D0 (en) | 2010-05-14 | 2010-06-30 | Medical Res Council Technology | Compounds |
| JP5863058B2 (ja) | 2010-05-17 | 2016-02-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １Ｈ−イミダゾ［４，５−ｃ］キノリン |
| US9303322B2 (en) | 2010-05-24 | 2016-04-05 | Integran Technologies Inc. | Metallic articles with hydrophobic surfaces |
| WO2011149827A1 (en) | 2010-05-24 | 2011-12-01 | Glaxosmithkline Llc | Compounds and methods |
| MX2012014158A (es) | 2010-06-04 | 2013-02-07 | Hoffmann La Roche | Derivados de aminopirimidina como moduladores de proteina cinasa rica repeticiones leucina 2 (lrrk2). |
| KR101208198B1 (ko) | 2010-08-27 | 2012-12-04 | 인제대학교 산학협력단 | Ｌｒｒｋ２ 인산화효소 억제 활성을 갖는 화합물을 유효성분으로 함유하는 파킨슨병 치료 또는 예방용 약학조성물 |
| JP5781611B2 (ja) | 2010-09-02 | 2015-09-24 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｌｒｒｋ２キナーゼ阻害剤としての２−（ベンジルオキシ）ベンズアミド類 |
| WO2012034526A1 (en) | 2010-09-16 | 2012-03-22 | Hutchison Medipharma Limited | Fused heteroaryls and their uses |
| GB201015949D0 (en) | 2010-09-22 | 2010-11-03 | Medical Res Council Technology | Compounds |
| JP5310700B2 (ja) | 2010-10-27 | 2013-10-09 | パナソニック株式会社 | Ｌｅｄパッケージ製造システムおよびｌｅｄパッケージ製造システムにおける樹脂塗布方法 |
| WO2012058193A1 (en) | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | Leucine-rich repeat kinase enzyme activity |
| PH12013500880A1 (en) | 2010-11-10 | 2013-07-01 | Hoffmann La Roche | Pyrazole aminopyrimidine derivatives as lrrk2 modulators |
| CN103348243A (zh) | 2010-11-30 | 2013-10-09 | 基因泰克公司 | Lrrk2的分析方法和生物标记物 |
| US20130338106A1 (en) | 2011-02-28 | 2013-12-19 | John A. McCauley | Compounds inhibiting leucine-rich repeat kinase enzyme activity |
| US9493452B2 (en) | 2011-03-24 | 2016-11-15 | Southern Methodist University | Compounds and derivatives of 2H-pyrido (3,2-b)(1, 4) oxazin 3)4H)-ones as raf kinase and LRRK2 inhibitors |
| GB201105137D0 (en) | 2011-03-28 | 2011-05-11 | Isis Innovation | Therapeutic molecules for use in the suppression of Parkinson's disease |
| US8791112B2 (en) | 2011-03-30 | 2014-07-29 | Arrien Pharmaceuticals Llc | Substituted 5-(pyrazin-2-yl)-1H-pyrazolo [3, 4-B] pyridine and pyrazolo [3, 4-B] pyridine derivatives as protein kinase inhibitors |
| CA2831634C (en) | 2011-04-21 | 2019-11-12 | Origenis Gmbh | Pyrazolo [4,3-d] pyrimidines useful as kinase inhibitors |
| MX365784B (es) | 2011-04-21 | 2019-05-28 | Origenis Gmbh | Compuestos heterociclicos como inhibidores de cinasas. |
| WO2012159079A1 (en) | 2011-05-18 | 2012-11-22 | The Parkinson's Institute | Assay to determine lrrk2 activity in parkinson's disease |
| RU2637936C2 (ru) | 2011-05-23 | 2017-12-08 | Элан Фармасьютикалз, Инк. | Ингибиторы активности киназы lrrk2 |
| WO2012178015A2 (en) | 2011-06-24 | 2012-12-27 | Zenobia Therapeutics, Inc. | Lrrk2 inhibitors |
| WO2013007768A1 (en) | 2011-07-13 | 2013-01-17 | F. Hoffmann-La Roche Ag | Tricyclic heterocyclic compounds, compositions and methods of use thereof as jak inhibitors |
| ES2583477T3 (es) | 2011-09-30 | 2016-09-21 | Ipsen Pharma S.A.S. | Inhibidores macrocíclicos de cinasa de LRRK2 |
| GB201204985D0 (en) | 2012-03-21 | 2012-05-02 | Genentech Inc | Compounds |
| WO2013166276A1 (en) | 2012-05-02 | 2013-11-07 | Southern Research Institute | Triazolopyridazine compounds, use as inhibitors of the kinase lrrk2, and methods for preparation thereof |
| JP6218808B2 (ja) | 2012-05-03 | 2017-10-25 | ジェネンテック， インコーポレイテッド | Ｌｒｒｋ２モジュレ−タ−としてのピラゾ−ルアミノピリミジン誘導体 |
| MD20140130A2 (ro) * | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| US10000482B2 (en) | 2012-10-19 | 2018-06-19 | Origenis Gmbh | Kinase inhibitors |
| US9260426B2 (en) | 2012-12-14 | 2016-02-16 | Arrien Pharmaceuticals Llc | Substituted 1H-pyrrolo [2, 3-b] pyridine and 1H-pyrazolo [3, 4-b] pyridine derivatives as salt inducible kinase 2 (SIK2) inhibitors |
| JP6116239B2 (ja) | 2012-12-28 | 2017-04-19 | キヤノン株式会社 | 被検体情報取得装置および被検体情報取得方法 |
| EP2816840B1 (en) | 2013-03-21 | 2017-01-04 | Huawei Device Co., Ltd. | Adaptive transmission scheme with two modes of operation |
| WO2015022664A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| WO2015140614A1 (en) | 2014-03-21 | 2015-09-24 | Align Technology, Inc. | Segmented orthodontic appliance with elastics |
-
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- 2013-06-19 MD MD20140130A patent/MD20140130A2/ro not_active Application Discontinuation
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