SG181857A1 - Fused heteroaromatic pyrrolidinones as syk inhibitors - Google Patents

Info

Publication number

SG181857A1

SG181857A1 SG2012045936A SG2012045936A SG181857A1 SG 181857 A1 SG181857 A1 SG 181857A1 SG 2012045936 A SG2012045936 A SG 2012045936A SG 2012045936 A SG2012045936 A SG 2012045936A SG 181857 A1 SG181857 A1 SG 181857A1

Authority

SG

Singapore

Prior art keywords

pyrrolo

pyridin

fluoro

dihydro

aminocyclohexylamino

Prior art date

2009-12-23

Links

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• -1 heteroaromatic pyrrolidinones Chemical class 0.000 title claims description 233
• 239000003112 inhibitor Substances 0.000 title claims description 13
• 150000001875 compounds Chemical class 0.000 claims abstract description 421
• 150000003839 salts Chemical class 0.000 claims abstract description 87
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 238000000034 method Methods 0.000 claims abstract description 46
• 201000010099 disease Diseases 0.000 claims abstract description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 201000009030 Carcinoma Diseases 0.000 claims abstract description 12
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 12
• 208000002250 Hematologic Neoplasms Diseases 0.000 claims abstract description 9
• 125000005843 halogen group Chemical group 0.000 claims description 99
• 125000001424 substituent group Chemical group 0.000 claims description 85
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
• 229910052739 hydrogen Inorganic materials 0.000 claims description 73
• 229920006395 saturated elastomer Polymers 0.000 claims description 72
• 239000001257 hydrogen Substances 0.000 claims description 66
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 54
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 26
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 125000002950 monocyclic group Chemical group 0.000 claims description 22
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 125000000335 thiazolyl group Chemical group 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• 125000006413 ring segment Chemical group 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 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 10
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• MJHOMTRKVMKCNE-NWDGAFQWSA-N mivavotinib Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 MJHOMTRKVMKCNE-NWDGAFQWSA-N 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• VPNLOOYVNORYBV-UONOGXRCSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3N=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 VPNLOOYVNORYBV-UONOGXRCSA-N 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 5
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 5
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 229960000485 methotrexate Drugs 0.000 claims description 5
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
• NANBZQDYUFCFNV-LSDHHAIUSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)spiro[6h-pyrrolo[3,4-d]pyrimidine-7,1'-cyclopropane]-5-one Chemical compound CC1=CC=CC(NC=2C3=C(C4(CC4)NC3=O)N=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 NANBZQDYUFCFNV-LSDHHAIUSA-N 0.000 claims description 4
• IBRCKLBEVCEQHD-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-benzofuran-3-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2C3=CC=CC=C3OC=2)=C(C(=O)NC2)C2=C1F IBRCKLBEVCEQHD-LSDHHAIUSA-N 0.000 claims description 4
• JHMLNISRSWFRDP-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylsulfonylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CS(=O)(=O)C1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 JHMLNISRSWFRDP-JKSUJKDBSA-N 0.000 claims description 4
• IYJQOJUTDKHGSO-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-chloro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(Cl)C2=C1C(=O)NC2 IYJQOJUTDKHGSO-NWDGAFQWSA-N 0.000 claims description 4
• BRUXXXWLFWMGMH-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-pyrazolo[1,5-a]pyridin-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=C3C=CC=CN3N=C2)=C(C(=O)NC2)C2=C1F BRUXXXWLFWMGMH-UONOGXRCSA-N 0.000 claims description 4
• ZBJMLPUPNJBUBV-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclopentyl]amino]-4-(3-methylsulfonylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CS(=O)(=O)C1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCC3)N)N=2)=C1 ZBJMLPUPNJBUBV-LSDHHAIUSA-N 0.000 claims description 4
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 4
• 201000009961 allergic asthma Diseases 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 208000029742 colonic 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
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• JRTCSSCKQPIELQ-UHFFFAOYSA-N 2-(cyclohexylamino)-4-(3-methylanilino)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3N=C(NC3CCCCC3)N=2)=C1 JRTCSSCKQPIELQ-UHFFFAOYSA-N 0.000 claims description 3
• NLHMXERGXZJVSA-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-benzothiophen-3-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2C3=CC=CC=C3SC=2)=C(C(=O)NC2)C2=C1F NLHMXERGXZJVSA-LSDHHAIUSA-N 0.000 claims description 3
• BIRMRVDNUGHXQF-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=CC2=C1C(=O)NC2 BIRMRVDNUGHXQF-QWHCGFSZSA-N 0.000 claims description 3
• VHBREDNCCOLHGT-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(4-fluoro-3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C(F)C(C)=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 VHBREDNCCOLHGT-JKSUJKDBSA-N 0.000 claims description 3
• YUGJNJDUJMQFPH-UONOGXRCSA-N 6-[[(3s,4r)-4-aminooxolan-3-yl]amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](COC3)N)N=2)=C1 YUGJNJDUJMQFPH-UONOGXRCSA-N 0.000 claims description 3
• 206010066476 Haematological malignancy Diseases 0.000 claims description 3
• 101000604583 Homo sapiens Tyrosine-protein kinase SYK Proteins 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 206010042971 T-cell lymphoma Diseases 0.000 claims description 3
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 3
• 208000007536 Thrombosis Diseases 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• ROSODFDWJFAKQI-UHFFFAOYSA-N 1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NC=C2C(=O)NCC2=C1 ROSODFDWJFAKQI-UHFFFAOYSA-N 0.000 claims description 2
• UCFAUSQCVJRLNA-LSDHHAIUSA-N 2-[[(1r,2s)-2-(methylamino)cyclohexyl]amino]-4-(3-methylanilino)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound CN[C@H]1CCCC[C@H]1NC(N=C1NC=2C=C(C)C=CC=2)=NC2=C1C(=O)NC2 UCFAUSQCVJRLNA-LSDHHAIUSA-N 0.000 claims description 2
• RVAKPWBSEAKFQD-GXTWGEPZSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1h-indol-2-yl)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1C=2NC3=CC=CC=C3C=2)=NC2=C1C(=O)NC2 RVAKPWBSEAKFQD-GXTWGEPZSA-N 0.000 claims description 2
• PIMALXKGEPZTHN-DTWKUNHWSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1h-pyrazol-5-yl)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1C=2NN=CC=2)=NC2=C1C(=O)NC2 PIMALXKGEPZTHN-DTWKUNHWSA-N 0.000 claims description 2
• RZJUCOGLHVRVMU-QWHCGFSZSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-chloroanilino)-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1NC=2C=C(Cl)C=CC=2)=NC2=C1C(=O)NC2 RZJUCOGLHVRVMU-QWHCGFSZSA-N 0.000 claims description 2
• FHXRJVORQQEROL-QWHCGFSZSA-N 2-[[(1r,2s)-2-aminocyclohexyl]amino]-4-[1-(2-methoxyethyl)pyrazol-4-yl]-6,7-dihydropyrrolo[3,4-d]pyrimidin-5-one Chemical compound C1=NN(CCOC)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=NC2=C1C(=O)NC2 FHXRJVORQQEROL-QWHCGFSZSA-N 0.000 claims description 2
• PNRLUYPLNOPXDL-MLGOLLRUSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NC(C2=CN(N=C2)C2CC2)=C(C(=O)NC2)C2=C1F PNRLUYPLNOPXDL-MLGOLLRUSA-N 0.000 claims description 2
• HYXZKQNQMCBUBO-NOZJJQNGSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NC(C2=CN(N=C2)C(F)F)=C(C(=O)NC2)C2=C1F HYXZKQNQMCBUBO-NOZJJQNGSA-N 0.000 claims description 2
• XOTZDLZZONOQJK-QMTHXVAHSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-7-fluoro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=C(F)C2=C1C(=O)NC2 XOTZDLZZONOQJK-QMTHXVAHSA-N 0.000 claims description 2
• MVSNAIBOHYBGEN-VHSXEESVSA-N 6-[[(1r,2s)-2-amino-4,4-difluorocyclopentyl]amino]-7-fluoro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CC(F)(F)C2)N)=C(F)C2=C1C(=O)NC2 MVSNAIBOHYBGEN-VHSXEESVSA-N 0.000 claims description 2
• RBAFUBZTBXELTG-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-cyclopropylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1C2=CN(N=C2)C2CC2)=CC2=C1C(=O)NC2 RBAFUBZTBXELTG-LSDHHAIUSA-N 0.000 claims description 2
• UHMBAIDDVAGJCG-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN(N=C2)C2CC2)=C(C(=O)NC2)C2=C1F UHMBAIDDVAGJCG-UONOGXRCSA-N 0.000 claims description 2
• FFDWUYASOWCJJD-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-ethylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(CC)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=CC2=C1C(=O)NC2 FFDWUYASOWCJJD-UONOGXRCSA-N 0.000 claims description 2
• NQOCNKBQTUREJV-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]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](CCCC2)N)=C(F)C2=C1C(=O)NC2 NQOCNKBQTUREJV-QWHCGFSZSA-N 0.000 claims description 2
• BCQZEYKBUNMINW-DTWKUNHWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(2-amino-1,3-thiazol-5-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2SC(N)=NC=2)=C(C(=O)NC2)C2=C1F BCQZEYKBUNMINW-DTWKUNHWSA-N 0.000 claims description 2
• YJDDNHXATJAJQT-ZWKOTPCHSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-7-(1h-pyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(C3=CNN=C3)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 YJDDNHXATJAJQT-ZWKOTPCHSA-N 0.000 claims description 2
• ZHCYNQAPDHKDTK-ZWKOTPCHSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-7-(2-methylpyrazol-3-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(=C(N[C@H]3[C@H](CCCC3)N)N=2)C=2N(N=CC=2)C)=C1 ZHCYNQAPDHKDTK-ZWKOTPCHSA-N 0.000 claims description 2
• WELNIAICBOVSLC-WDEREUQCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN(N=C2)C(F)F)=C(C(=O)NC2)C2=C1F WELNIAICBOVSLC-WDEREUQCSA-N 0.000 claims description 2
• XXHYTGBBQIPUKC-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-bromo-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(Br)C2=C1C(=O)NC2 XXHYTGBBQIPUKC-NWDGAFQWSA-N 0.000 claims description 2
• XLLZLRGOFITEPW-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-1,1-dimethyl-4-(1-methylpyrazol-4-yl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2(C)C XLLZLRGOFITEPW-NWDGAFQWSA-N 0.000 claims description 2
• DDFCHGYRRJNLDH-CLGJWYQZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-1-methyl-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1NC(=O)C(C(=N2)C3=CN(C)N=C3)=C1C(F)=C2N[C@@H]1CCCC[C@@H]1N DDFCHGYRRJNLDH-CLGJWYQZSA-N 0.000 claims description 2
• XYDQHRTVTJCMOX-WDEREUQCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(2-methyl-1,3-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1C(C)=NC=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 XYDQHRTVTJCMOX-WDEREUQCSA-N 0.000 claims description 2
• WLWYGQASHVGFFB-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(4-methylimidazol-1-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NC(C)=CN1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 WLWYGQASHVGFFB-NWDGAFQWSA-N 0.000 claims description 2
• HPFJFZGOUINWHT-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(4-methylthiophen-2-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CSC(C=2C=3C(=O)NCC=3C(F)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 HPFJFZGOUINWHT-NWDGAFQWSA-N 0.000 claims description 2
• JVWJCIFIORGGQG-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(5-methylthiophen-2-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1C(C)=CC=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 JVWJCIFIORGGQG-NWDGAFQWSA-N 0.000 claims description 2
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