JP2014520153A5 - - Google Patents
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- Publication number
- JP2014520153A5 JP2014520153A5 JP2014517111A JP2014517111A JP2014520153A5 JP 2014520153 A5 JP2014520153 A5 JP 2014520153A5 JP 2014517111 A JP2014517111 A JP 2014517111A JP 2014517111 A JP2014517111 A JP 2014517111A JP 2014520153 A5 JP2014520153 A5 JP 2014520153A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- fluoro
- pyridin
- amino
- pyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- -1 independently Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 2
- MWUUTAHCGPVMGD-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(2-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(CCC=2C=CC=CC=2)=C(C(=O)NC2)C2=C1F MWUUTAHCGPVMGD-JKSUJKDBSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- AALZKTBJAHBKIM-DLBZAZTESA-N 2-[6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-4-yl]indolizine-7-carbonitrile Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3C=CC(=CC3=C2)C#N)=C(C(=O)NC2)C2=C1F AALZKTBJAHBKIM-DLBZAZTESA-N 0.000 claims 1
- MSIZNRKVWRIDQG-JKSUJKDBSA-N 2-[6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-4-yl]indolizine-7-carbonitrile Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN3C=CC(=CC3=C2)C#N)=C(C(=O)NC2)C2=C1F MSIZNRKVWRIDQG-JKSUJKDBSA-N 0.000 claims 1
- BYYUBVVRSVRORA-LSDHHAIUSA-N 2-[6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-4-yl]indolizine-7-carboxylic acid Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN3C=CC(=CC3=C2)C(O)=O)=C(C(=O)NC2)C2=C1F BYYUBVVRSVRORA-LSDHHAIUSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- GTOSCSXFGOTWAI-JKSUJKDBSA-N 6-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[2-(4-chlorophenyl)ethenyl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=CC=2C=CC(Cl)=CC=2)=C(C(=O)NC2)C2=C1F GTOSCSXFGOTWAI-JKSUJKDBSA-N 0.000 claims 1
- ILYPOBPXMJWJFJ-JKSUJKDBSA-N 6-[[(1R,2S)-2-aminocyclohexyl]amino]-7-fluoro-4-[2-(4-fluorophenyl)ethenyl]-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=CC=2C=CC(F)=CC=2)=C(C(=O)NC2)C2=C1F ILYPOBPXMJWJFJ-JKSUJKDBSA-N 0.000 claims 1
- WCQFYGIKQVUAJL-DLBZAZTESA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(2-ethyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2CN(CC)CCN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N WCQFYGIKQVUAJL-DLBZAZTESA-N 0.000 claims 1
- ICJSIOUKJLKMOP-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3,3-dimethyl-1,4-dihydropyrrolo[2,1-c][1,4]oxazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C)(C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N ICJSIOUKJLKMOP-JKSUJKDBSA-N 0.000 claims 1
- XPEHSUNGNRAAOP-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3CCOCC3=C2)=C(C(=O)NC2)C2=C1F XPEHSUNGNRAAOP-LSDHHAIUSA-N 0.000 claims 1
- KSIXMJYOYSSTSY-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-ethyl-1,2-thiazol-5-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1N=C(CC)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 KSIXMJYOYSSTSY-NWDGAFQWSA-N 0.000 claims 1
- FMLPQWTWEPFPEK-MWSTZMHHSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-ethyl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(CC)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N FMLPQWTWEPFPEK-MWSTZMHHSA-N 0.000 claims 1
- CDOCWXKICXPYQF-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3CCNCC3=C2)=C(C(=O)NC2)C2=C1F CDOCWXKICXPYQF-LSDHHAIUSA-N 0.000 claims 1
- ABOYRNQDMXFSQI-VHSXEESVSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(1,2-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2SN=CC=2)=C(C(=O)NC2)C2=C1F ABOYRNQDMXFSQI-VHSXEESVSA-N 0.000 claims 1
- BOHREQSTYGQSDK-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(1-methylpyrrolo[1,2-a]imidazol-6-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2N(C)C=CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N BOHREQSTYGQSDK-UONOGXRCSA-N 0.000 claims 1
- KBEHGNZKNGYPJO-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(1-methylpyrrolo[1,2-b]pyrazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C=1N2N(C)C=CC2=CC=1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N KBEHGNZKNGYPJO-LSDHHAIUSA-N 0.000 claims 1
- RJDDTLCPSXBIPF-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(1-oxo-3,4-dihydro-2h-pyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3CCNC(=O)C3=C2)=C(C(=O)NC2)C2=C1F RJDDTLCPSXBIPF-QWHCGFSZSA-N 0.000 claims 1
- FCZPYUBJLQGDBQ-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(2-methyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2CN(C)CCN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N FCZPYUBJLQGDBQ-JKSUJKDBSA-N 0.000 claims 1
- JASYGAUBDPBJIS-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(2-phenylethynyl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C#CC=2C=CC=CC=2)=C(C(=O)NC2)C2=C1F JASYGAUBDPBJIS-JKSUJKDBSA-N 0.000 claims 1
- CKWYNQDPEPTZGN-WDEREUQCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-methyl-1,2-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1N=C(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 CKWYNQDPEPTZGN-WDEREUQCSA-N 0.000 claims 1
- KYYKDKCQGXGNPY-JNMIHDSVSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-methyl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N KYYKDKCQGXGNPY-JNMIHDSVSA-N 0.000 claims 1
- IXAXSFRVCJFSNB-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-oxo-2,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3CC(=O)NCC3=C2)=C(C(=O)NC2)C2=C1F IXAXSFRVCJFSNB-UONOGXRCSA-N 0.000 claims 1
- NLXKVRVSKWUORS-MYFVLZFPSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-propan-2-yl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C(C)C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCCC[C@@H]1N NLXKVRVSKWUORS-MYFVLZFPSA-N 0.000 claims 1
- MTJISHIDJWPBKM-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(8-oxo-6,7-dihydro-5h-indolizin-2-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3CCCC(=O)C3=C2)=C(C(=O)NC2)C2=C1F MTJISHIDJWPBKM-UONOGXRCSA-N 0.000 claims 1
- DRGYJTNEQXREEM-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-indolizin-2-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3C=CC=CC3=C2)=C(C(=O)NC2)C2=C1F DRGYJTNEQXREEM-JKSUJKDBSA-N 0.000 claims 1
- ZFESFTMIZCANII-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-pyrrolo[2,1-b][1,3]oxazol-6-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN3C=COC3=C2)=C(C(=O)NC2)C2=C1F ZFESFTMIZCANII-QWHCGFSZSA-N 0.000 claims 1
- JAYZLGRFYYIRSS-NWDGAFQWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(1-ethylpyrazol-4-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(CC)C=C1C1=NC(N[C@H]2[C@H](COCC2)N)=C(F)C2=C1C(=O)NC2 JAYZLGRFYYIRSS-NWDGAFQWSA-N 0.000 claims 1
- ARXVOEHXCVGYCU-JKSUJKDBSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(2-ethyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2CN(CC)CCN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N ARXVOEHXCVGYCU-JKSUJKDBSA-N 0.000 claims 1
- UYIJXAXKBPGFDT-LSDHHAIUSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(3,3-dimethyl-1,4-dihydropyrrolo[2,1-c][1,4]oxazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C)(C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N UYIJXAXKBPGFDT-LSDHHAIUSA-N 0.000 claims 1
- RFDIBDBQIIFGQL-WDEREUQCSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(3-cyclopropyl-1,2-thiazol-5-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C=2SN=C(C=2)C2CC2)=C(C(=O)NC2)C2=C1F RFDIBDBQIIFGQL-WDEREUQCSA-N 0.000 claims 1
- VPRIDPPDHLQLHU-WDEREUQCSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(3-ethyl-1,2-thiazol-5-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1N=C(CC)C=C1C1=NC(N[C@H]2[C@H](COCC2)N)=C(F)C2=C1C(=O)NC2 VPRIDPPDHLQLHU-WDEREUQCSA-N 0.000 claims 1
- NOGPEZQTDOCICR-PXWJKWRZSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(3-ethyl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(CC)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N NOGPEZQTDOCICR-PXWJKWRZSA-N 0.000 claims 1
- RIXBRCYGAUHAGL-UONOGXRCSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN3CCNCC3=C2)=C(C(=O)NC2)C2=C1F RIXBRCYGAUHAGL-UONOGXRCSA-N 0.000 claims 1
- NWOWSJVGVQVYPU-DTWKUNHWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(1,2-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C=2SN=CC=2)=C(C(=O)NC2)C2=C1F NWOWSJVGVQVYPU-DTWKUNHWSA-N 0.000 claims 1
- NRBCTWAJWQKNRG-QWHCGFSZSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(1-methylpyrrolo[1,2-a]imidazol-6-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2N(C)C=CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N NRBCTWAJWQKNRG-QWHCGFSZSA-N 0.000 claims 1
- RURDXIRQZMQXHT-UONOGXRCSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(1-methylpyrrolo[1,2-b]pyrazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C=1N2N(C)C=CC2=CC=1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N RURDXIRQZMQXHT-UONOGXRCSA-N 0.000 claims 1
- QLNFBIHVDVNNIR-NWDGAFQWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(1-oxo-3,4-dihydro-2h-pyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN3CCNC(=O)C3=C2)=C(C(=O)NC2)C2=C1F QLNFBIHVDVNNIR-NWDGAFQWSA-N 0.000 claims 1
- HXTRBMANMHUSGW-LSDHHAIUSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(2-methyl-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2CN(C)CCN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N HXTRBMANMHUSGW-LSDHHAIUSA-N 0.000 claims 1
- QSKBUQYHZOBTBZ-LSDHHAIUSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(2-phenylethynyl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C#CC=2C=CC=CC=2)=C(C(=O)NC2)C2=C1F QSKBUQYHZOBTBZ-LSDHHAIUSA-N 0.000 claims 1
- ANSDCVVNQPGCKK-XVDHHWJWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(3-methyl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N ANSDCVVNQPGCKK-XVDHHWJWSA-N 0.000 claims 1
- DNPNFFXIVFRBIX-RTKIROINSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-(3-propan-2-yl-3,4-dihydro-1h-pyrrolo[2,1-c][1,4]oxazin-7-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C2COC(C(C)C)CN2C=C1C(C=1C(=O)NCC=1C=1F)=NC=1N[C@@H]1CCOC[C@@H]1N DNPNFFXIVFRBIX-RTKIROINSA-N 0.000 claims 1
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- KYCRLVJBFHIGBI-NWDGAFQWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-7-fluoro-4-pyrrolo[2,1-b][1,3]oxazol-6-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN3C=COC3=C2)=C(C(=O)NC2)C2=C1F KYCRLVJBFHIGBI-NWDGAFQWSA-N 0.000 claims 1
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG181857A1 (en) | 2009-12-23 | 2012-07-30 | Takeda Pharmaceutical | Fused heteroaromatic pyrrolidinones as syk inhibitors |
| CN103833665B (zh) * | 2014-02-24 | 2015-09-23 | 杰达维（上海）医药科技发展有限公司 | 一种新的合成异噻唑的方法 |
| PL3233857T3 (pl) * | 2014-12-18 | 2020-07-27 | Takeda Pharmaceutical Company Limited | Stałe postacie skondensowanych heteroaromatycznych pirolidynonów |
| US11174254B2 (en) | 2017-09-28 | 2021-11-16 | Yangtze River Pharmaceutical Group Co., Ltd. | Aniline-substituted 1,2-dihydropyrrol[3,4-C]pyridin/pyrimidin-3-one derivative and use thereof |
| SG11202002475TA (en) * | 2017-10-19 | 2020-04-29 | Bayer Animal Health Gmbh | Use of fused heteroaromatic pyrrolidones for treatment and prevention of diseases in animals |
| ES3030701T3 (en) | 2018-05-10 | 2025-07-01 | Zoetis Services Llc | Endoparasitic depsipeptides |
| CN111004211B (zh) * | 2019-12-29 | 2021-04-02 | 苏州诚和医药化学有限公司 | 一种依匹哌唑中间体4-溴苯并［b］噻吩的合成方法 |
| CN111393349A (zh) * | 2020-05-15 | 2020-07-10 | 上海毕得医药科技有限公司 | 一种4-碘-1h-吡咯-2-甲醛的合成方法 |
| CN117510431A (zh) * | 2023-11-08 | 2024-02-06 | 浙江雅辰药物科技股份有限公司 | 一种异噻唑-3-酮及其衍生物、合成方法 |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63107966A (ja) | 1986-05-22 | 1988-05-12 | Fujisawa Pharmaceut Co Ltd | ピリミジン誘導体 |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US5272158A (en) | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5238950A (en) | 1991-12-17 | 1993-08-24 | Schering Corporation | Inhibitors of platelet-derived growth factor |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| EP1054004B1 (en) | 1997-12-15 | 2008-07-16 | Astellas Pharma Inc. | Novel pyrimidine-5-carboxamide derivatives |
| WO1999032479A1 (en) | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Phthalimide-piperidine, -pyrrolidine and -azepine derivatives, their preparation and their use as muscarinic receptor (ant-)agonists |
| EP1184376B1 (en) | 1999-06-09 | 2005-02-02 | Yamanouchi Pharmaceutical Co. Ltd. | Novel heterocyclic carboxamide derivatives |
| GB9918035D0 (en) | 1999-07-30 | 1999-09-29 | Novartis Ag | Organic compounds |
| EP1250128A2 (en) | 1999-12-16 | 2002-10-23 | Alcon, Inc. | Inhibitors of adenosine kinase for the treatment of optic nerve and retinal damage |
| EP1244668B1 (en) | 2000-01-07 | 2006-04-05 | Universitaire Instelling Antwerpen | Purine derivatives, process for their preparation and use thereof |
| AU2001232271A1 (en) | 2000-02-14 | 2001-08-20 | Japan Tobacco Inc. | Preventives/remedies for postoperative stress |
| JP2001302667A (ja) | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| US7105667B2 (en) | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| PE20030008A1 (es) | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| WO2003009852A1 (en) | 2001-07-24 | 2003-02-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US20030158195A1 (en) | 2001-12-21 | 2003-08-21 | Cywin Charles L. | 1,6 naphthyridines useful as inhibitors of SYK kinase |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| MXPA05001804A (es) | 2002-08-14 | 2005-05-27 | Vertex Pharma | Inhibidores de proteinas cinasas y usos de los mismos. |
| AU2003286711A1 (en) | 2002-10-25 | 2004-05-13 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| AU2003286895A1 (en) | 2002-11-05 | 2004-06-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of jak and other protein kinases |
| EP1610793A2 (en) | 2003-03-25 | 2006-01-04 | Vertex Pharmaceuticals Incorporated | Thiazoles useful as inhibitors of protein kinases |
| CA2523126A1 (en) | 2003-03-25 | 2004-10-14 | Vertex Pharmaceuticals Incorporated | Thiazoles useful as inhibitors of protein kinases |
| KR20050122220A (ko) | 2003-03-25 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 디펩티딜 펩티다제 억제제 |
| US8178671B2 (en) | 2003-07-30 | 2012-05-15 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2, 4-pyrimidinediamine compounds |
| US7320992B2 (en) | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
| US20050182061A1 (en) | 2003-10-02 | 2005-08-18 | Jeremy Green | Phthalimide compounds useful as protein kinase inhibitors |
| WO2005056524A2 (en) | 2003-12-09 | 2005-06-23 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| US8057815B2 (en) | 2004-04-19 | 2011-11-15 | Portola Pharmaceuticals, Inc. | Methods of treatment with Syk inhibitors |
| JP2008511659A (ja) | 2004-09-01 | 2008-04-17 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物の合成 |
| EP1814878B1 (en) | 2004-11-24 | 2012-01-04 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
| US20060128710A1 (en) | 2004-12-09 | 2006-06-15 | Chih-Hung Lee | Antagonists to the vanilloid receptor subtype 1 (VR1) and uses thereof |
| KR100926399B1 (ko) | 2005-04-06 | 2009-11-12 | 아이알엠 엘엘씨 | 디아릴아민―함유 화합물 및 조성물, 및 스테로이드 호르몬핵 수용체의 조절제로서의 그들의 용도 |
| US7745641B2 (en) | 2005-04-19 | 2010-06-29 | Kyowa Hakko Kirin Co., Ltd. | Nitrogen-containing heterocyclic compound |
| WO2006129100A1 (en) | 2005-06-03 | 2006-12-07 | Glaxo Group Limited | Novel compounds |
| CA2608476A1 (en) | 2005-06-28 | 2007-01-04 | Bausch & Lomb Incorporated | Preparations comprising arylazine substituted with a carbonylic moiety to increase the activity of gelatinase a in ocular cells |
| AR056191A1 (es) | 2005-08-23 | 2007-09-26 | Idenix Phatmaceuticals Inc | Anillo de nucleosidos de siete miembros como inhibidores de la replica viral, metodos para su sintesis, composiciones farmaceuticas que los contienen y su uso en el tratamiento de infecciones con virus de la familia flaviviridae |
| WO2007023382A2 (en) | 2005-08-25 | 2007-03-01 | Pfizer Inc. | Pyrimidine amino pyrazole compounds, potent kinase inhibitors |
| US20070117775A1 (en) | 2005-10-31 | 2007-05-24 | Rigel Pharmaceuticals, Inc. | Compositions and Methods For Treating Inflammatory Disorders |
| WO2007070872A1 (en) | 2005-12-15 | 2007-06-21 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
| EP2537849A3 (en) | 2006-01-17 | 2013-04-03 | Vertex Pharmaceuticals, Inc. | Azaindoles useful as inhibitors of janus kinases |
| CL2007002617A1 (es) | 2006-09-11 | 2008-05-16 | Sanofi Aventis | Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto. |
| EP2108642A1 (en) | 2006-10-17 | 2009-10-14 | Kyowa Hakko Kirin Co., Ltd. | Jak inhibitor |
| MX2009004077A (es) | 2006-10-19 | 2009-05-05 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| WO2008057402A2 (en) | 2006-11-02 | 2008-05-15 | Cytovia, Inc. | N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| JP5264759B2 (ja) | 2006-11-21 | 2013-08-14 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物のプロドラッグ塩およびそれらの使用 |
| JPWO2008081928A1 (ja) | 2006-12-28 | 2010-04-30 | 大正製薬株式会社 | ピラゾロピリミジン化合物 |
| JP2010522174A (ja) | 2007-03-23 | 2010-07-01 | シェーリング コーポレイション | Ｈｃｖｎｓ３−プロテアーゼ阻害剤としてのヒドラジド−ペプチド |
| EP2162136A4 (en) | 2007-06-03 | 2012-02-15 | Univ Vanderbilt | GLUTAMATE METABOTROPIC POSITIVE RECEPTOR-BASED ALLOSTERIC-MODULATOR BENZAMIDE DERIVATIVES (MGLUR5) AND METHODS OF MAKING AND USING THEM |
| WO2009026107A1 (en) | 2007-08-17 | 2009-02-26 | Portola Pharmaceuticals, Inc. | Protein kinase inhibitors |
| JP2009067729A (ja) | 2007-09-14 | 2009-04-02 | Kyowa Hakko Kirin Co Ltd | Ｈｓｐ９０ファミリー蛋白質阻害剤 |
| CA2705303A1 (en) | 2007-11-07 | 2009-05-14 | Foldrx Pharmaceuticals, Inc. | Modulation of protein trafficking |
| WO2009080638A2 (en) | 2007-12-20 | 2009-07-02 | Cellzome Limited | Sulfamides as zap-70 inhibitors |
| JP5496915B2 (ja) | 2008-02-13 | 2014-05-21 | シージーアイ ファーマシューティカルズ，インコーポレーテッド | ６−アリール−イミダゾ［１，２−ａ］ピラジン誘導体、その製造方法、及びその使用方法 |
| AU2009215430B2 (en) | 2008-02-22 | 2015-02-12 | Rigel Pharmaceuticals, Inc. | Use of 2,4-pyrimidinediamines for the treatment of atherosclerosis |
| US8436005B2 (en) | 2008-04-03 | 2013-05-07 | Abbott Laboratories | Macrocyclic pyrimidine derivatives |
| WO2009145856A1 (en) | 2008-04-16 | 2009-12-03 | Portola Pharmaceuticals, Inc. | 2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or jak kinases inhibitors |
| KR101773313B1 (ko) | 2008-04-16 | 2017-08-31 | 포톨라 파마슈티컬스, 인코포레이티드 | ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드 |
| EP2310381A1 (en) | 2008-06-13 | 2011-04-20 | Novartis AG | 2,4'-bipyridinyl compounds as protein kinase d inhibitors useful for the treatment of ia heart failure and cancer |
| WO2010015518A2 (de) | 2008-08-05 | 2010-02-11 | Boehringer Ingelheim Interntional Gmbh | 4-dimethylamino-phenyl-substituierte naphthyridine und ihre verwendung als arzneimittel |
| WO2010015520A1 (de) | 2008-08-05 | 2010-02-11 | Boehringer Ingelheim International Gmbh | Substituierte naphthyridine und ihre verwendung als arzneimittel |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| EP3552607A3 (en) | 2008-12-08 | 2020-01-15 | Gilead Connecticut, Inc. | Imidazopyrazine syk inhibitors |
| EP2443106A1 (en) | 2009-06-18 | 2012-04-25 | Cellzome Limited | Heterocyclylaminopyrimidines as kinase inhibitors |
| MX2012007154A (es) | 2009-12-17 | 2012-08-01 | Merck Sharp & Dohme | Aminopirimidinas como inhibidores de syk. |
| EP2512246B1 (en) | 2009-12-17 | 2015-09-30 | Merck Sharp & Dohme Corp. | Aminopyrimidines as syk inhibitors |
| SG181857A1 (en) | 2009-12-23 | 2012-07-30 | Takeda Pharmaceutical | Fused heteroaromatic pyrrolidinones as syk inhibitors |
| GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
-
2012
- 2012-06-20 US US14/128,576 patent/US9056873B2/en not_active Expired - Fee Related
- 2012-06-20 WO PCT/US2012/043276 patent/WO2012177714A1/en not_active Ceased
- 2012-06-20 JP JP2014517111A patent/JP6026525B2/ja not_active Expired - Fee Related
- 2012-06-20 EP EP12738263.8A patent/EP2723739B1/en active Active
-
2015
- 2015-05-07 US US14/706,876 patent/US9663514B2/en not_active Expired - Fee Related
-
2017
- 2017-05-18 US US15/599,337 patent/US20170327497A1/en not_active Abandoned
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