JP6026525B2 - 置換６−アザ−イソインドリン−１−オン誘導体 - Google Patents

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Publication number

JP6026525B2

JP6026525B2 JP2014517111A JP2014517111A JP6026525B2 JP 6026525 B2 JP6026525 B2 JP 6026525B2 JP 2014517111 A JP2014517111 A JP 2014517111A JP 2014517111 A JP2014517111 A JP 2014517111A JP 6026525 B2 JP6026525 B2 JP 6026525B2

Authority

JP

Japan

Prior art keywords

pyrrolo

fluoro

pyridin

amino

pyran

Prior art date

2011-06-22

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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• ROSODFDWJFAKQI-UHFFFAOYSA-N 1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical class C1=NC=C2C(=O)NCC2=C1 ROSODFDWJFAKQI-UHFFFAOYSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 339
• -1 independently Chemical group 0.000 claims description 209
• 150000003839 salts Chemical class 0.000 claims description 61
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 238000011282 treatment Methods 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 25
• 206010028980 Neoplasm Diseases 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000006413 ring segment Chemical group 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000005549 heteroarylene group Chemical group 0.000 claims description 15
• GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
• 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 description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 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 description 6
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 5
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 5
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 5
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 206010042971 T-cell lymphoma Diseases 0.000 claims description 4
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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