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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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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| PL2516434T3 (pl) | 2009-12-23 | 2015-11-30 | Takeda Pharmaceuticals Co | Skondensowane heteroaromatyczne pirolidynony jako inhibitory SYK |
| 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 |
| EP3677582B1 (en) * | 2014-12-18 | 2023-01-25 | Calithera Biosciences Inc. | Solid state forms of fused heteroaromatic pyrrolidinones |
| WO2019062329A1 (zh) * | 2017-09-28 | 2019-04-04 | 上海海雁医药科技有限公司 | 4,6,7-三取代1,2-二氢吡咯并[3,4-c]吡啶/嘧啶-3-酮衍生物及用途 |
| KR20200073216A (ko) | 2017-10-19 | 2020-06-23 | 바이엘 애니멀 헬스 게엠베하 | 동물에서의 질환의 치료 및 방지를 위한 융합된 헤테로방향족 피롤리돈의 용도 |
| HUE071406T2 (hu) | 2018-05-10 | 2025-08-28 | Zoetis Services Llc | Endoparazitikus depszipeptidek |
| 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 |
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-
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 EP EP12738263.8A patent/EP2723739B1/en active Active
- 2012-06-20 JP JP2014517111A patent/JP6026525B2/ja not_active Expired - Fee Related
-
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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