JP6189948B2 - ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン - Google Patents
ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン Download PDFInfo
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- JP6189948B2 JP6189948B2 JP2015519416A JP2015519416A JP6189948B2 JP 6189948 B2 JP6189948 B2 JP 6189948B2 JP 2015519416 A JP2015519416 A JP 2015519416A JP 2015519416 A JP2015519416 A JP 2015519416A JP 6189948 B2 JP6189948 B2 JP 6189948B2
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- JP
- Japan
- Prior art keywords
- pyrrolo
- morpholin
- pyrimidine
- pyrimidin
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- -1 4- (substituted amino) -7H-pyrrolo [2,3-d] pyrimidines Chemical class 0.000 title claims description 114
- 229940124786 LRRK2 inhibitor Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 215
- 150000003839 salts Chemical class 0.000 claims description 68
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 208000018737 Parkinson disease Diseases 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 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 description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 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 description 10
- 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 description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 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 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 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 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 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 description 3
- 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 description 3
- 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 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 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 description 2
- 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 description 2
- 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 description 2
- PFFIEMXZEROLOA-GFCCVEGCSA-N 3-[4-[(2r)-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-GFCCVEGCSA-N 0.000 claims description 2
- XRIIKVLOTOSHOP-LBPRGKRZSA-N 3-[4-[(3s)-3-methylmorpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C[C@H]1COCCN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 XRIIKVLOTOSHOP-LBPRGKRZSA-N 0.000 claims description 2
- 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 description 2
- QGBBQZOBGGTKLP-UHFFFAOYSA-N 3-chloro-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QGBBQZOBGGTKLP-UHFFFAOYSA-N 0.000 claims description 2
- GAMPREVSPQKZEE-UHFFFAOYSA-N 3-methoxy-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 GAMPREVSPQKZEE-UHFFFAOYSA-N 0.000 claims description 2
- FAMMXMXUDBKFET-UHFFFAOYSA-N 3-methyl-5-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound CC1=CC(C#N)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 FAMMXMXUDBKFET-UHFFFAOYSA-N 0.000 claims description 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 description 2
- OCXIEZDHSFMBOX-UHFFFAOYSA-N 4-(5-isoquinolin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C3=CC=CC=C3C=NC=1)=CN2 OCXIEZDHSFMBOX-UHFFFAOYSA-N 0.000 claims description 2
- MUOUHNBOXJIELS-UHFFFAOYSA-N 4-(5-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C=CC=CC=1)=CN2 MUOUHNBOXJIELS-UHFFFAOYSA-N 0.000 claims description 2
- UZSUNCZXHIZLKQ-UHFFFAOYSA-N 4-(5-pyridin-3-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)morpholine Chemical compound C1COCCN1C1=NC=NC2=C1C(C=1C=NC=CC=1)=CN2 UZSUNCZXHIZLKQ-UHFFFAOYSA-N 0.000 claims description 2
- RGWYNOKIZOFIMS-UHFFFAOYSA-N 4-[5-(1,3-dimethylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NN(C)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 RGWYNOKIZOFIMS-UHFFFAOYSA-N 0.000 claims description 2
- ICEVOSIVNSAQIF-UHFFFAOYSA-N 4-[5-(1-ethylpyrazol-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NN(CC)C=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ICEVOSIVNSAQIF-UHFFFAOYSA-N 0.000 claims description 2
- CZDNODODMNYBAC-UHFFFAOYSA-N 4-[5-(1-methylpyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CN1C=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=N1 CZDNODODMNYBAC-UHFFFAOYSA-N 0.000 claims description 2
- WCIXCVUKGLJANE-UHFFFAOYSA-N 4-[5-(2,4-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC(F)=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 WCIXCVUKGLJANE-UHFFFAOYSA-N 0.000 claims description 2
- PXYVAWXCGMFHEJ-UHFFFAOYSA-N 4-[5-(2,5-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=C(F)C(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 PXYVAWXCGMFHEJ-UHFFFAOYSA-N 0.000 claims description 2
- ZQFMADILMOIBBC-UHFFFAOYSA-N 4-[5-(2,6-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC=CC(F)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 ZQFMADILMOIBBC-UHFFFAOYSA-N 0.000 claims description 2
- WOWULVZMWDEPKC-UHFFFAOYSA-N 4-[5-(2-chloro-3-fluoro-6-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=C(F)C(Cl)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 WOWULVZMWDEPKC-UHFFFAOYSA-N 0.000 claims description 2
- QSEOKDHHFXGCDV-UHFFFAOYSA-N 4-[5-(2-chloro-5-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=C(Cl)C(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QSEOKDHHFXGCDV-UHFFFAOYSA-N 0.000 claims description 2
- VAMWIRPKQLTAMA-UHFFFAOYSA-N 4-[5-(2-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound ClC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 VAMWIRPKQLTAMA-UHFFFAOYSA-N 0.000 claims description 2
- UGVUXLJRIDUDEE-UHFFFAOYSA-N 4-[5-(2-fluoro-6-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC(F)=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 UGVUXLJRIDUDEE-UHFFFAOYSA-N 0.000 claims description 2
- OICKVPGRZUWXPB-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 OICKVPGRZUWXPB-UHFFFAOYSA-N 0.000 claims description 2
- KIEKMNYAWLEJNU-UHFFFAOYSA-N 4-[5-(3,5-difluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound FC1=CC(F)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 KIEKMNYAWLEJNU-UHFFFAOYSA-N 0.000 claims description 2
- LZEFYMNXDMEWJB-UHFFFAOYSA-N 4-[5-(3-fluoro-5-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC(F)=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 LZEFYMNXDMEWJB-UHFFFAOYSA-N 0.000 claims description 2
- FGDZZZPJSRHPSU-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholine Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C=C(F)C=CC=4)=CNC=3N=CN=2)=N1 FGDZZZPJSRHPSU-UHFFFAOYSA-N 0.000 claims description 2
- QZZMUIJVVAGHJA-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 QZZMUIJVVAGHJA-UHFFFAOYSA-N 0.000 claims description 2
- JMAPTHRNJHOVDP-UHFFFAOYSA-N 4-[5-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 JMAPTHRNJHOVDP-UHFFFAOYSA-N 0.000 claims description 2
- YSHZFIKJKZMGKM-UHFFFAOYSA-N 4-[5-(3-methylsulfanylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CSC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 YSHZFIKJKZMGKM-UHFFFAOYSA-N 0.000 claims description 2
- TZWUTAYHWCWNFP-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC(F)=CC=C1C1=CNC2=NC=NC(N3CCOCC3)=C12 TZWUTAYHWCWNFP-UHFFFAOYSA-N 0.000 claims description 2
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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- Health & Medical Sciences (AREA)
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| ES2617339T3 (es) | 2010-12-16 | 2017-06-16 | Calchan Limited | Derivados de pirrolopirimidina inhibidores de ASK1 |
| CA2868302A1 (en) | 2012-03-23 | 2013-09-26 | Dennis M. Brown | Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo |
| US8963597B1 (en) * | 2013-10-02 | 2015-02-24 | Nanya Technology Corporation | Cross-domain enablement method and electronic apparatus |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | 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 |
| RU2016134751A (ru) | 2014-01-29 | 2018-03-02 | Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Соединения |
| MA39219B1 (fr) * | 2014-01-29 | 2018-11-30 | Glaxosmithkline Ip Dev Ltd | Nouveaux composés inhibiteurs de la kinase lrrk2 utilisés pour le traitement du parkinson, de l’alzheimer et de la sclérose latérale amyotrophique |
| 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 |
| KR102562866B1 (ko) | 2014-11-14 | 2023-08-04 | 네르비아노 메디칼 사이언시스 에스.알.엘. | 단백질 키나아제 억제제로서의 6-아미노-7-바이사이클로-7-데아자-퓨린 유도체 |
| 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 |
| RU2761626C2 (ru) * | 2017-02-03 | 2021-12-13 | Лео Фарма А/С | ПРОИЗВОДНЫЕ 5-(7Н-ПИРРОЛО[2,3-d]ПИРИМИДИН-4-ИЛ)-5-АЗАСПИРО[2.5]ОКТАН-8-КАРБОНОВОЙ КИСЛОТЫ В КАЧЕСТВЕ НОВЫХ ИНГИБИТОРОВ JAK-КИНАЗЫ |
| 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 |
| KR101923852B1 (ko) | 2017-02-24 | 2018-11-29 | 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 |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | 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 |
| SG11202108519TA (en) | 2019-02-13 | 2021-09-29 | Ptc Therapeutics Inc | Thioeno[3,2-b] pyridin-7-amine compounds for treating familial dysautonomia |
| WO2020167624A1 (en) | 2019-02-13 | 2020-08-20 | Ptc Therapeutics, Inc. | Pyrrolo[2,3-d]pyrimidine compounds for treating familial dysautonomia |
| CA3139277A1 (en) | 2019-05-08 | 2020-11-12 | Vimalan Biosciences, Inc. | Jak inhibitors |
| MX2022001702A (es) | 2019-08-08 | 2022-04-20 | Vimalan Biosciences Inc | Inhibidores de jak. |
| US20230024521A1 (en) * | 2019-09-25 | 2023-01-26 | Vimalan Biosciences, Inc. | Jak inhibitors |
| BR112022007680A2 (pt) | 2019-10-25 | 2022-08-09 | Merck Sharp & Dohme | Derivados de n-(heteroaril)quinazolin-2-amina como inibidores de lrrk2, composições farmacêuticas, e usos dos mesmos |
| KR20230012464A (ko) * | 2020-02-25 | 2023-01-26 | 브이아이비 브이지더블유 | 류신-풍부 반복 키나제 2 알로스테릭 조절제 |
| 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 |
| WO2022084210A1 (en) * | 2020-10-20 | 2022-04-28 | F. Hoffmann-La Roche Ag | Combination therapy of pd-1 axis binding antagonists and lrrk2 inhitibors |
| 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 |
| CA3217559A1 (en) * | 2021-05-05 | 2022-11-10 | Kamaluddin Abdur-Rashid | Catalytic tryptamine processes and precursors |
| CN118251225A (zh) * | 2021-09-07 | 2024-06-25 | Ptc医疗公司 | 治疗神经退行性疾病的方法 |
| US20250051337A1 (en) * | 2021-09-28 | 2025-02-13 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of serine/threonine protein kinase stk3 or stk4 and uses thereof |
| JP2024541934A (ja) | 2021-10-27 | 2024-11-13 | ハー・ルンドベック・アクチエゼルスカベット | Ｌｒｒｋ２阻害剤 |
| 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 |
| US5864033A (en) | 1989-09-15 | 1999-01-26 | Metabasis Therapeutics, Inc. | Adenosine kinase inhibitors |
| US5721356A (en) * | 1989-09-15 | 1998-02-24 | Gensia, Inc. | Orally active adenosine kinase inhibitors |
| US5763597A (en) | 1989-09-15 | 1998-06-09 | Metabasis Therapeutics, Inc. | Orally active adenosine kinase inhibitors |
| US5674998A (en) | 1989-09-15 | 1997-10-07 | Gensia Inc. | C-4' modified adenosine kinase inhibitors |
| US5646128A (en) | 1989-09-15 | 1997-07-08 | Gensia, Inc. | Methods for treating adenosine kinase related conditions |
| US5795977A (en) | 1989-09-15 | 1998-08-18 | Metabasis Therapeutics, Inc. | Water soluble adenosine kinase inhibitors |
| US5763596A (en) | 1989-09-15 | 1998-06-09 | Metabasis Therapeutics, Inc. | C-4' modified adenosine kinase inhibitors |
| US5726302A (en) | 1989-09-15 | 1998-03-10 | Gensia Inc. | Water soluble 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 |
| ES2150941T3 (es) | 1992-04-03 | 2000-12-16 | Upjohn Co | Aminas biciclicas-heterociclicas eficaces farmaceuticamente. |
| 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 |
| WO1995011898A1 (en) | 1992-05-12 | 1995-05-04 | Nissan Chemical Industries Ltd. | Condensed pyridine type mevalonolactone intermediate and process for its production |
| 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 |
| WO1994008975A1 (fr) | 1992-10-16 | 1994-04-28 | Nippon Soda Co., Ltd. | Derive de pyrimidine |
| ATE239797T1 (de) | 1993-01-25 | 2003-05-15 | Takeda Chemical Industries Ltd | Antikörper gegen beta-amyloid oder derivative davon und seine verwendung |
| 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 |
| DE59500788D1 (de) | 1994-05-03 | 1997-11-20 | 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 |
| WO1997034895A1 (de) * | 1996-03-15 | 1997-09-25 | Novartis Ag | NEUE N-7 HETEROCYCLYL-PYRROLO[2,3-d]PYRIMIDINE UND IHRE VERWENDUNG |
| 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 |
| WO1998023613A1 (en) * | 1996-11-27 | 1998-06-04 | Pfizer Inc. | Fused bicyclic pyrimidine derivatives |
| 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 |
| NZ337765A (en) | 1997-04-09 | 2001-09-28 | Mindset Biopharmaceuticals Usa | Recombinant antibodies having specificity for beta-amyloid N-terminus and C-terminus and use in treating Alzheimer's Disease |
| US8173127B2 (en) | 1997-04-09 | 2012-05-08 | Intellect Neurosciences, Inc. | Specific antibodies to amyloid beta peptide, pharmaceutical compositions 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 |
| SK286640B6 (sk) * | 1998-06-19 | 2009-03-05 | Pfizer Products Inc. | Pyrol [2,3-d] pyrimidínová zlúčenina, jej použitie na výrobu liečiva, farmaceutická kompozícia s jej obsahom, použitie jej kombinácie s ďalšími činidlami a súpravy s jej obsahom na výrobu liečiva |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| 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 |
| DE1257584T1 (de) | 2000-02-24 | 2003-05-28 | Lilly Co Eli | Humanisierte antikörper, die amyloid beta peptid demarkieren |
| 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 |
| WO2002051837A2 (en) | 2000-12-22 | 2002-07-04 | Wyeth | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| GB0111186D0 (en) | 2001-05-08 | 2001-06-27 | Smithkline Beecham Plc | Novel compounds |
| WO2003000187A2 (en) * | 2001-06-21 | 2003-01-03 | Ariad Pharmaceuticals, Inc. | Novel pyrazolo-and pyrrolo-pyrimidines and uses thereof |
| CA2451998A1 (en) | 2001-08-17 | 2003-02-27 | Eli Lilly And Company | Anti-a.beta. antibodies |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| WO2003076658A2 (en) | 2002-03-08 | 2003-09-18 | Decode Genetics Ehf. | A susceptibility gene for late-onset idiopathic parkinson's disease |
| EP1545515A1 (en) | 2002-08-12 | 2005-06-29 | 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 |
| US20040146512A1 (en) | 2002-10-09 | 2004-07-29 | Arnon Rosenthal | Methods of treating Alzheimer's disease using antibodies directed against amyloid beta peptide and compositions thereof |
| 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 |
| BRPI0410630A (pt) | 2003-06-19 | 2006-06-13 | Pfizer Prod Inc | antagonista de nk1 |
| 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 |
| EP1666061A1 (en) | 2003-09-09 | 2006-06-07 | 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 |
| US20050239806A1 (en) * | 2004-01-13 | 2005-10-27 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| EP1720847A1 (en) | 2004-02-02 | 2006-11-15 | Pfizer Products Incorporated | Histamine-3 receptor modulators |
| BRPI0509298A (pt) | 2004-04-01 | 2007-09-18 | Lilly Co Eli | composto, composição farmacêutica, métodos de inibir receptor h3 de histamina em um mamìfero, para tratar ou prevenir um distúrbio do sistema nervoso, obesidade, e um distúrbio ou doença, e, uso de um composto |
| AR049333A1 (es) | 2004-04-02 | 2006-07-19 | Vertex Pharma | Azaindoles inhibidores de proteinquinasas rock y otras proteinas quinasas. composiciones farmaceuticas. |
| 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 |
| AP2006003768A0 (en) | 2004-05-25 | 2006-10-31 | Pfizer Prod Inc | TetraazabenzoÄeÜazulene derivatives and analogs tehereof |
| US8197819B2 (en) | 2004-06-08 | 2012-06-12 | Novartis Vaccines And Diagnostics, Inc. | Env polypeptide complexes and methods of use |
| MXPA06015237A (es) | 2004-06-29 | 2007-12-10 | Amgen Inc | Pirrolo[2-3-d]pirimidinas que modulan la actividad de ack1 y lck. |
| MX2007000998A (es) | 2004-07-30 | 2007-07-11 | Rinat Neuroscience Corp | Anticuerpos dirigidos peptido beta-amiloide y procedimientos que usan los mismos. |
| WO2006042102A2 (en) | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| US8029986B2 (en) | 2004-10-21 | 2011-10-04 | Helmholtz Zentrum Muenchen Deutsches Forschungszentrum fuer Gesundheit und Umwelt(GmbH) | KASPP (LRRK2) gene, its production and use for the detection and treatment of neurodegenerative disorders |
| EP1812450A2 (en) | 2004-11-10 | 2007-08-01 | Eli Lilly And Company | Tgf-beta inhibitors |
| DE102004054634A1 (de) | 2004-11-12 | 2006-05-18 | Schwarz Pharma Ag | Azaindolcarboxamide |
| US20090074775A1 (en) | 2004-12-22 | 2009-03-19 | David Michael Holtzman | Use Of Anti-AB Antibody To Treat Traumatic Brain Injury |
| 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. |
| DE602006018301D1 (de) | 2005-06-22 | 2010-12-30 | Pfizer Prod Inc | Histamin-3-rezeptorantagonisten |
| US8158673B2 (en) | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| CA2624625A1 (en) | 2005-11-04 | 2007-05-10 | 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 |
| WO2007076423A2 (en) | 2005-12-22 | 2007-07-05 | Smithkline Beecham Corporation | INHIBITORS OF Akt ACTIVITY |
| EA200870117A1 (ru) | 2005-12-23 | 2008-12-30 | Смитклайн Бичам Корпорейшн | Азаиндоловые ингибиторы аурора-киназ |
| WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
| WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists 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 |
| CA2643055A1 (en) | 2006-03-13 | 2007-09-20 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| DK1866433T3 (da) | 2006-03-14 | 2009-08-17 | Cellzome Ag | Fremgangsmåde til identifikation af LRRK-2interagerende molekyler og til rensning af LRRK2 |
| 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 |
| WO2007149798A2 (en) | 2006-06-20 | 2007-12-27 | Novartis Ag | Biomarkers for the progression of alzheimer's disease |
| US8466163B2 (en) | 2006-12-11 | 2013-06-18 | Bionomics Limited | Furo[2,3-d]pyrimidines and related compounds and methods for treating disease states by inhibiting tubulin polymerization |
| WO2008075007A1 (en) * | 2006-12-21 | 2008-06-26 | Cancer Research Technology Limited | Morpholino-substituted bicycloheteroaryl compounds and their use as anti cancer agents |
| JP4585610B2 (ja) | 2007-01-22 | 2010-11-24 | ファイザー・プロダクツ・インク | 治療用化合物のトシル酸塩およびその医薬組成物 |
| 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 |
| 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 |
| EP2139869A2 (en) * | 2007-04-13 | 2010-01-06 | SuperGen, Inc. | Axl kinase inhibitors useful for the treatment of cancer or hyperproliferative disorders |
| RS52166B (sr) | 2007-05-11 | 2012-08-31 | Pfizer Inc. | Amino-heterociklična jedinjenja |
| 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 |
| US20100186098A1 (en) | 2007-06-27 | 2010-07-22 | 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 |
| CA2698818A1 (en) | 2007-09-14 | 2009-03-19 | Sanofi-Aventis | 3-methyl-2- ( (2s) -2- (4- (3-methyl-1, 2, 4-oxadiazol-5-yl) phenyl) morpholino) -6- (pyrimidin-4-yl) pyrimidin-4 (3h) -one as tau protein kinase inhibitor |
| US20090118276A1 (en) | 2007-11-02 | 2009-05-07 | Wyeth | Thienopyrimidines, thienopyridines, and pyrrolopyrimidines as b-raf inhibitors |
| AU2008333215B2 (en) | 2007-12-05 | 2013-06-13 | Johannes Gutenberg-Universitat 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 |
| AU2009238590A1 (en) | 2008-04-22 | 2009-10-29 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| CN102014627B (zh) | 2008-04-30 | 2014-10-29 | 国家卫生研究院 | 作为极光激酶抑制剂的稠合双环嘧啶化合物 |
| 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 |
| DE102008031517A1 (de) | 2008-07-03 | 2010-01-07 | Merck Patent Gmbh | Pyrrolopyridinyl-pyrimidin-2-yl-amin-derivate |
| US20110201599A1 (en) | 2008-07-03 | 2011-08-18 | Exelixis, Inc. | CDK Modulators |
| 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 |
| EP3828185B1 (en) | 2009-01-06 | 2024-11-20 | 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 |
| KR20100092909A (ko) | 2009-02-13 | 2010-08-23 | 주식회사 엘지생명과학 | 잔틴 옥시다제 저해제로서 효과적인 신규 화합물, 그 제조방법 및 그를 함유하는 약제학적 조성물 |
| EP2408772B1 (en) * | 2009-03-19 | 2015-07-01 | Medical Research Council Technology | Compounds |
| 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 |
| US9908884B2 (en) | 2009-05-05 | 2018-03-06 | Dana-Farber Cancer Institute, Inc. | EGFR inhibitors and methods of treating disorders |
| DE102009019962A1 (de) | 2009-05-05 | 2010-11-11 | Merck Patent Gmbh | 3-([1,2,3]Triazol-4-yl)-pyrrolo[2,3-b]pyridinderivate |
| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| JP5752691B2 (ja) | 2009-09-29 | 2015-07-22 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | 新規化合物 |
| FR2951172B1 (fr) | 2009-10-13 | 2014-09-26 | Pf Medicament | Derives pyrazolopyridines en tant qu'agent anticancereux |
| MX2012004846A (es) | 2009-10-29 | 2012-10-05 | 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 |
| EA024729B1 (ru) | 2009-11-13 | 2016-10-31 | Джиноско | Киназные ингибиторы |
| 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 |
| LT3001903T (lt) | 2009-12-21 | 2018-01-10 | Samumed, Llc | 1h-pirazolo[3,4-b]piridinai ir jų terapinis panaudojimas |
| 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 |
| WO2011144622A1 (en) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | 1h - imidazo [4, 5 - c] quinolines |
| WO2011149827A1 (en) | 2010-05-24 | 2011-12-01 | Glaxosmithkline Llc | Compounds and methods |
| US9303322B2 (en) | 2010-05-24 | 2016-04-05 | Integran Technologies Inc. | Metallic articles with hydrophobic surfaces |
| ES2577829T3 (es) | 2010-06-04 | 2016-07-19 | F. Hoffmann-La Roche Ag | Derivados de aminopirimidina como moduladores de la LRRK2 |
| KR101208198B1 (ko) | 2010-08-27 | 2012-12-04 | 인제대학교 산학협력단 | Ｌｒｒｋ２ 인산화효소 억제 활성을 갖는 화합물을 유효성분으로 함유하는 파킨슨병 치료 또는 예방용 약학조성물 |
| WO2012028629A1 (en) | 2010-09-02 | 2012-03-08 | Glaxo Group Limited | 2 - (benzyloxy) benzamides as lrrk2 kinase inhibitors |
| NZ607527A (en) | 2010-09-16 | 2015-04-24 | Hutchison Medipharma Ltd | 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 |
| US9233977B2 (en) | 2010-10-29 | 2016-01-12 | Merck Sharp & Dohme Corp. | Leucine-rich repeat kinase enzyme activity |
| NO2638031T3 (https=) | 2010-11-10 | 2018-03-10 | ||
| RU2013129818A (ru) | 2010-11-30 | 2015-01-10 | Дженентек, Инк. | Способы анализа и биомаркеры для гена lrrk2 |
| 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 |
| AP2013007253A0 (en) | 2011-04-21 | 2013-11-30 | Origenis Gmbh | Pyrazolo [4,3-D] pyrimidines useful as kinase inhibitors |
| AU2012244549B2 (en) | 2011-04-21 | 2017-04-20 | Origenis Gmbh | Heterocyclic compounds as kinase inhibitors |
| 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 |
| US20140205537A1 (en) | 2011-06-24 | 2014-07-24 | 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 |
| HUE029728T2 (en) | 2011-09-30 | 2017-03-28 | Ipsen Pharma Sas | Macrocyclic LRRK2 kinase inhibitors |
| 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 |
| EP2844652B1 (en) | 2012-05-03 | 2019-03-13 | Genentech, Inc. | Pyrazole aminopyrimidine derivatives as lrrk2 modulators |
| EP2867236B1 (en) * | 2012-06-29 | 2017-06-14 | Pfizer Inc | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| WO2014060113A1 (en) | 2012-10-19 | 2014-04-24 | Origenis Gmbh | Novel 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 |
| CN103518398B (zh) | 2013-03-21 | 2017-07-07 | 华为终端有限公司 | 数据传输方法、基站及用户设备 |
| WO2015022664A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | 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 |
| EP3119347B1 (en) | 2014-03-21 | 2023-06-07 | Align Technology, Inc. | Segmented orthodontic appliance with elastics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017226684A (ja) * | 2012-06-29 | 2017-12-28 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン |
| JP2019073522A (ja) * | 2012-06-29 | 2019-05-16 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン |
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