ME02186B - Fuzionisani heteroaromatski pirolidinoni kao syk inhibitori - Google Patents
Fuzionisani heteroaromatski pirolidinoni kao syk inhibitoriInfo
- Publication number
- ME02186B ME02186B MEP-2015-125A MEP12515A ME02186B ME 02186 B ME02186 B ME 02186B ME P12515 A MEP12515 A ME P12515A ME 02186 B ME02186 B ME 02186B
- Authority
- ME
- Montenegro
- Prior art keywords
- pyrrolo
- pyridin
- fluoro
- ylamino
- aminocyclohexylamino
- Prior art date
Links
- -1 heteroaromatic pyrrolidinones Chemical class 0.000 title claims 9
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- NTLKAXQBFYZMAH-UHFFFAOYSA-N 2-methylpentanamide Chemical compound CCCC(C)C(N)=O NTLKAXQBFYZMAH-UHFFFAOYSA-N 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 201000009030 Carcinoma Diseases 0.000 claims 3
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- ACMPWZQOUILVFB-UHFFFAOYSA-N 4-methylpentanamide Chemical compound CC(C)CCC(N)=O ACMPWZQOUILVFB-UHFFFAOYSA-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
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 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 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- KDUTVDRIWILGKD-CYBMUJFWSA-N (2r)-2-[[4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C(=C1)C=NN1C1CC1 KDUTVDRIWILGKD-CYBMUJFWSA-N 0.000 claims 1
- XRGNIAJRYCAFFV-SNVBAGLBSA-N (2r)-2-[[4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=NN(C(F)F)C=1 XRGNIAJRYCAFFV-SNVBAGLBSA-N 0.000 claims 1
- OVAPNXCAPWCXDI-SECBINFHSA-N (2r)-2-[[7-fluoro-3-oxo-4-(1,2-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=NS1 OVAPNXCAPWCXDI-SECBINFHSA-N 0.000 claims 1
- BAWQWVQBXIDYII-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(1-methylpyrazol-4-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=NN(C)C=1 BAWQWVQBXIDYII-LLVKDONJSA-N 0.000 claims 1
- ORFPWEPWRPUBLL-GFCCVEGCSA-N (2r)-2-[[7-fluoro-4-(1-methylpyrazol-4-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-n,4-dimethylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(=O)NC)=NC=1C=1C=NN(C)C=1 ORFPWEPWRPUBLL-GFCCVEGCSA-N 0.000 claims 1
- KUOCWDDVPWWSKP-SNVBAGLBSA-N (2r)-2-[[7-fluoro-4-(2-methyl-1,3-thiazol-5-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CN=C(C)S1 KUOCWDDVPWWSKP-SNVBAGLBSA-N 0.000 claims 1
- UZPROEIMLUTQLE-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(4-methylthiophen-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC(C)=CS1 UZPROEIMLUTQLE-LLVKDONJSA-N 0.000 claims 1
- NHPYANOEODOMDL-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(5-methylthiophen-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=C(C)S1 NHPYANOEODOMDL-LLVKDONJSA-N 0.000 claims 1
- WCEHKVNTHSOADA-GFCCVEGCSA-N (2r)-4-methyl-2-[[4-(1-methylpyrazol-4-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]pentanamide Chemical compound N=1C(N[C@H](CC(C)C)C(N)=O)=CC=2CNC(=O)C=2C=1C=1C=NN(C)C=1 WCEHKVNTHSOADA-GFCCVEGCSA-N 0.000 claims 1
- WWSSJPHZGVTEBD-OAHLLOKOSA-N (2r)-4-methyl-2-[[4-(3-methylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]pentanamide Chemical compound N=1C(N[C@H](CC(C)C)C(N)=O)=CC=2CNC(=O)C=2C=1NC1=CC=CC(C)=C1 WWSSJPHZGVTEBD-OAHLLOKOSA-N 0.000 claims 1
- IZLQWNFMZKOICR-OAHLLOKOSA-N (2r)-4-methyl-2-[[4-(3-methylsulfonylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]pentanamide Chemical compound N=1C(N[C@H](CC(C)C)C(N)=O)=CC=2CNC(=O)C=2C=1NC1=CC=CC(S(C)(=O)=O)=C1 IZLQWNFMZKOICR-OAHLLOKOSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- UXHMPPWAKKPFSX-UHFFFAOYSA-N 6-[(2-amino-3,3,3-trifluoropropyl)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(NCC(N)C(F)(F)F)N=2)=C1 UXHMPPWAKKPFSX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LOFXHRXBASKCPJ-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1h-indazol-6-ylamino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1NC=2C=C3NN=CC3=CC=2)=CC2=C1C(=O)NC2 LOFXHRXBASKCPJ-LSDHHAIUSA-N 0.000 claims 1
- UOBUBZWFFCOCAE-DLBZAZTESA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridine-7-carbonitrile Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(C#N)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 UOBUBZWFFCOCAE-DLBZAZTESA-N 0.000 claims 1
- JCKXIUBFRBOHRV-DLBZAZTESA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-7-prop-2-enoyl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(C(=O)C=C)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 JCKXIUBFRBOHRV-DLBZAZTESA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- QGIZHMIRSUGPQA-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-chloro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(Cl)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 QGIZHMIRSUGPQA-LSDHHAIUSA-N 0.000 claims 1
- 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 1
- 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 1
- QSLDDROANYSPRV-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(F)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 QSLDDROANYSPRV-LSDHHAIUSA-N 0.000 claims 1
- 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 1
- 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 1
- ZVLVGTYXHIBEQV-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-thiophen-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CSC=C2)=C(C(=O)NC2)C2=C1F ZVLVGTYXHIBEQV-NWDGAFQWSA-N 0.000 claims 1
- URAIYDRYCJOIAK-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-iodo-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(I)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 URAIYDRYCJOIAK-LSDHHAIUSA-N 0.000 claims 1
- 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 1
- MJHOMTRKVMKCNE-NEPJUHHUSA-N 6-[[(1s,2r)-2-aminocyclohexyl]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](CCCC2)N)=C(F)C2=C1C(=O)NC2 MJHOMTRKVMKCNE-NEPJUHHUSA-N 0.000 claims 1
- CNLZGMLAACBFPD-CQSZACIVSA-N 6-[[(2r)-2-amino-3-ethoxypropyl]amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N=1C(NC[C@@H](N)COCC)=CC=2CNC(=O)C=2C=1NC1=CC=CC(C)=C1 CNLZGMLAACBFPD-CQSZACIVSA-N 0.000 claims 1
- VFYIMFKQSSVIKO-GFCCVEGCSA-N 6-[[(2r)-2-amino-3-ethoxypropyl]amino]-7-fluoro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C=12C(=O)NCC2=C(F)C(NC[C@@H](N)COCC)=NC=1NC1=CC=CC(C)=C1 VFYIMFKQSSVIKO-GFCCVEGCSA-N 0.000 claims 1
- PTVFGLINHKTHNO-LLVKDONJSA-N 6-[[(2r)-2-amino-3-methoxypropyl]amino]-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N=1C(NC[C@@H](N)COC)=CC=2CNC(=O)C=2C=1C=1C=NN(C)C=1 PTVFGLINHKTHNO-LLVKDONJSA-N 0.000 claims 1
- MQRNMOQGZFFVSQ-CYBMUJFWSA-N 6-[[(2r)-2-amino-3-methoxypropyl]amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N=1C(NC[C@@H](N)COC)=CC=2CNC(=O)C=2C=1NC1=CC=CC(C)=C1 MQRNMOQGZFFVSQ-CYBMUJFWSA-N 0.000 claims 1
- NGAWMQNSOMDIGI-GFCCVEGCSA-N 6-[[(2r)-2-amino-3-methoxypropyl]amino]-4-(3-methylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridine-7-carbonitrile Chemical compound C=12C(=O)NCC2=C(C#N)C(NC[C@@H](N)COC)=NC=1NC1=CC=CC(C)=C1 NGAWMQNSOMDIGI-GFCCVEGCSA-N 0.000 claims 1
- DZSPBFLSHHMSRH-LLVKDONJSA-N 6-[[(2r)-2-amino-3-methoxypropyl]amino]-7-fluoro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C=12C(=O)NCC2=C(F)C(NC[C@@H](N)COC)=NC=1NC1=CC=CC(C)=C1 DZSPBFLSHHMSRH-LLVKDONJSA-N 0.000 claims 1
- FHNGEYIDIQGNFF-QWHCGFSZSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN(N=C2)C2CC2)=C(C(=O)NC2)C2=C1F FHNGEYIDIQGNFF-QWHCGFSZSA-N 0.000 claims 1
- QJXYPBJTYPNXKY-NWDGAFQWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]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](COCC2)N)=CC2=C1C(=O)NC2 QJXYPBJTYPNXKY-NWDGAFQWSA-N 0.000 claims 1
- QJZVPOAVHOGBBL-LSDHHAIUSA-N 6-[[(3r,4r)-3-aminooxan-4-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](COCC3)N)N=2)=C1 QJZVPOAVHOGBBL-LSDHHAIUSA-N 0.000 claims 1
- BLKFBGHXROJYIY-DTWKUNHWSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-(5-chlorothiophen-2-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C=2SC(Cl)=CC=2)=C(C(=O)NC2)C2=C1F BLKFBGHXROJYIY-DTWKUNHWSA-N 0.000 claims 1
- RYADIWBTHCLJOG-VHSXEESVSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]amino]-4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1COCC[C@H]1NC1=NC(C2=CN(N=C2)C(F)F)=C(C(=O)NC2)C2=C1F RYADIWBTHCLJOG-VHSXEESVSA-N 0.000 claims 1
- SVZXXGPSWXRXKK-VHSXEESVSA-N 6-[[(3r,4r)-3-aminooxan-4-yl]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](COCC2)N)=C(F)C2=C1C(=O)NC2 SVZXXGPSWXRXKK-VHSXEESVSA-N 0.000 claims 1
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Applications Claiming Priority (4)
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| US28996909P | 2009-12-23 | 2009-12-23 | |
| US38696410P | 2010-09-27 | 2010-09-27 | |
| EP10800835.0A EP2516434B1 (en) | 2009-12-23 | 2010-12-17 | Fused heteroaromatic pyrrolidinones as syk inhibitors |
| PCT/US2010/061146 WO2011079051A1 (en) | 2009-12-23 | 2010-12-17 | Fused heteroaromatic pyrrolidinones as syk inhibitors |
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| ME02186B true ME02186B (me) | 2016-02-20 |
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| MEP-2015-125A ME02186B (me) | 2009-12-23 | 2010-12-17 | Fuzionisani heteroaromatski pirolidinoni kao syk inhibitori |
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| WO2015164330A1 (en) | 2014-04-21 | 2015-10-29 | Millennium Pharmaceuticals, Inc. | Anti-psyk antibody molecules and use of same for syk-targeted therapy |
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