JP2012519678A5 - - Google Patents
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- JP2012519678A5 JP2012519678A5 JP2011552507A JP2011552507A JP2012519678A5 JP 2012519678 A5 JP2012519678 A5 JP 2012519678A5 JP 2011552507 A JP2011552507 A JP 2011552507A JP 2011552507 A JP2011552507 A JP 2011552507A JP 2012519678 A5 JP2012519678 A5 JP 2012519678A5
- Authority
- JP
- Japan
- Prior art keywords
- propyl
- pyrrolo
- pyrimidin
- amide
- alkyl
- 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.)
- Withdrawn
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- -1 cyano, hydroxyl Chemical group 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 206010030348 Open-Angle Glaucoma Diseases 0.000 claims 4
- 108091000080 Phosphotransferase Proteins 0.000 claims 4
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 102000020233 phosphotransferase Human genes 0.000 claims 4
- 201000006366 primary open angle glaucoma Diseases 0.000 claims 4
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims 3
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims 3
- 101001059429 Homo sapiens MAP/microtubule affinity-regulating kinase 3 Proteins 0.000 claims 3
- 101000976899 Homo sapiens Mitogen-activated protein kinase 15 Proteins 0.000 claims 3
- 101000665442 Homo sapiens Serine/threonine-protein kinase TBK1 Proteins 0.000 claims 3
- 101000820294 Homo sapiens Tyrosine-protein kinase Yes Proteins 0.000 claims 3
- 108060006678 I-kappa-B kinase Proteins 0.000 claims 3
- 102000001284 I-kappa-B kinase Human genes 0.000 claims 3
- 102100028920 MAP/microtubule affinity-regulating kinase 3 Human genes 0.000 claims 3
- 102100023483 Mitogen-activated protein kinase 15 Human genes 0.000 claims 3
- 102100038192 Serine/threonine-protein kinase TBK1 Human genes 0.000 claims 3
- 102100021788 Tyrosine-protein kinase Yes Human genes 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- JVTMFKNWOUPAJH-UHFFFAOYSA-N 2-cyclopentyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]acetamide Chemical compound C1=CC2=CN=C(NC=3C=NC(=CC=3)N3CCOCC3)N=C2N1CCCNC(=O)CC1CCCC1 JVTMFKNWOUPAJH-UHFFFAOYSA-N 0.000 claims 2
- IGXIMFJXKCORFY-UHFFFAOYSA-N 2-methyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]propanamide Chemical compound N1=C2N(CCCNC(=O)C(C)C)C=CC2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 IGXIMFJXKCORFY-UHFFFAOYSA-N 0.000 claims 2
- JBDXZYCZTGLKSE-UHFFFAOYSA-N 3-methyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]butanamide Chemical compound N1=C2N(CCCNC(=O)CC(C)C)C=CC2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 JBDXZYCZTGLKSE-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 230000006020 chronic inflammation Effects 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- ZDZQARUBFUYJJG-UHFFFAOYSA-N n-[3-[2-(1h-indazol-5-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC=3C=C4C=NNC4=CC=3)N=C2N1CCCNC(=O)C1CCC1 ZDZQARUBFUYJJG-UHFFFAOYSA-N 0.000 claims 2
- WIAYAESMRWUSID-UHFFFAOYSA-N n-[3-[2-(3-acetamidoanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclopentanecarboxamide Chemical compound CC(=O)NC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCCC4)C=CC3=CN=2)=C1 WIAYAESMRWUSID-UHFFFAOYSA-N 0.000 claims 2
- GBMZUVCNKNAKAG-UHFFFAOYSA-N n-[3-[2-(3-cyanoanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CC(C#N)=C1 GBMZUVCNKNAKAG-UHFFFAOYSA-N 0.000 claims 2
- LJNCBWDMHFJNTM-UHFFFAOYSA-N n-[3-[2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=CC3=CN=2)=C1 LJNCBWDMHFJNTM-UHFFFAOYSA-N 0.000 claims 2
- SQZZHXLACIZYDV-UHFFFAOYSA-N n-[3-[2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclopentanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCCC4)C=CC3=CN=2)=C1 SQZZHXLACIZYDV-UHFFFAOYSA-N 0.000 claims 2
- GUTMFMYTVXOHLR-UHFFFAOYSA-N n-[3-[2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C=4SC=CC=4)C=CC3=CN=2)=C1 GUTMFMYTVXOHLR-UHFFFAOYSA-N 0.000 claims 2
- NPGQUQIVGQHEAE-UHFFFAOYSA-N n-[3-[2-(3-morpholin-4-ylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1N1CCOCC1 NPGQUQIVGQHEAE-UHFFFAOYSA-N 0.000 claims 2
- VNYOEBQUJAUUFG-UHFFFAOYSA-N n-[3-[2-(4-morpholin-4-ylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 VNYOEBQUJAUUFG-UHFFFAOYSA-N 0.000 claims 2
- MJOYLEXXZJPKQY-UHFFFAOYSA-N n-[3-[2-(imidazo[1,2-a]pyridin-6-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC3=CN4C=CN=C4C=C3)N=C2N1CCCNC(=O)C1CCC1 MJOYLEXXZJPKQY-UHFFFAOYSA-N 0.000 claims 2
- FGYCJULFFFTMCW-UHFFFAOYSA-N n-[3-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CN=C1 FGYCJULFFFTMCW-UHFFFAOYSA-N 0.000 claims 2
- IVOCKDRLDRCJKO-UHFFFAOYSA-N n-[3-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CN=C1 IVOCKDRLDRCJKO-UHFFFAOYSA-N 0.000 claims 2
- SASKQCOPYLRNPM-UHFFFAOYSA-N n-[3-[2-(quinolin-6-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC=3C=C4C=CC=NC4=CC=3)N=C2N1CCCNC(=O)C1CCC1 SASKQCOPYLRNPM-UHFFFAOYSA-N 0.000 claims 2
- YMSKBSJRJRNOIR-UHFFFAOYSA-N n-[3-[2-(quinoxalin-6-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC=3C=C4N=CC=NC4=CC=3)N=C2N1CCCNC(=O)C1CCC1 YMSKBSJRJRNOIR-UHFFFAOYSA-N 0.000 claims 2
- DJFDJUNGHWFJBM-UHFFFAOYSA-N n-[3-[2-[(1-ethylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=NN(CC)C=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 DJFDJUNGHWFJBM-UHFFFAOYSA-N 0.000 claims 2
- CAMSUDMBGHNVCS-UHFFFAOYSA-N n-[3-[2-[(1-methylindazol-5-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 CAMSUDMBGHNVCS-UHFFFAOYSA-N 0.000 claims 2
- SOCMOEBIHDQWNA-UHFFFAOYSA-N n-[3-[2-[(1-methylindazol-6-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 SOCMOEBIHDQWNA-UHFFFAOYSA-N 0.000 claims 2
- UXBFGLMTWRQROK-UHFFFAOYSA-N n-[3-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 UXBFGLMTWRQROK-UHFFFAOYSA-N 0.000 claims 2
- HYZFDZRTUAUVNS-UHFFFAOYSA-N n-[3-[2-[(1-methylpyrazolo[3,4-b]pyridin-5-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C=1N=C2N(C)N=CC2=CC=1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 HYZFDZRTUAUVNS-UHFFFAOYSA-N 0.000 claims 2
- CQTLXLLUCCXTAH-UHFFFAOYSA-N n-[3-[2-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 CQTLXLLUCCXTAH-UHFFFAOYSA-N 0.000 claims 2
- SVMVLQNRBXGIIV-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 SVMVLQNRBXGIIV-UHFFFAOYSA-N 0.000 claims 2
- OYOLWPLUUKRJQM-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]butanamide Chemical compound N1=C2N(CCCNC(=O)CCC)C=CC2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 OYOLWPLUUKRJQM-UHFFFAOYSA-N 0.000 claims 2
- HHIWINYKIMADIE-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 HHIWINYKIMADIE-UHFFFAOYSA-N 0.000 claims 2
- BKRCADGEPNHIPK-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 BKRCADGEPNHIPK-UHFFFAOYSA-N 0.000 claims 2
- RWTHBCUIXAFSTO-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclopentanecarboxamide Chemical compound C1CCCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 RWTHBCUIXAFSTO-UHFFFAOYSA-N 0.000 claims 2
- GKHIWUWTZSCKON-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 GKHIWUWTZSCKON-UHFFFAOYSA-N 0.000 claims 2
- GUXLOIRKBQPSNB-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 GUXLOIRKBQPSNB-UHFFFAOYSA-N 0.000 claims 2
- FWWONYJHCFHGNU-UHFFFAOYSA-N n-[3-[2-[3-(1,2,4-triazol-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1N1C=NC=N1 FWWONYJHCFHGNU-UHFFFAOYSA-N 0.000 claims 2
- HXVAENCJCDIHDG-UHFFFAOYSA-N n-[3-[2-[3-(1,3-oxazol-5-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1C1=CN=CO1 HXVAENCJCDIHDG-UHFFFAOYSA-N 0.000 claims 2
- JNFZXIAPZXXSKI-UHFFFAOYSA-N n-[3-[2-[3-(2-oxopyrrolidin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1N1CCCC1=O JNFZXIAPZXXSKI-UHFFFAOYSA-N 0.000 claims 2
- TWPYVVZZLDOPKE-UHFFFAOYSA-N n-[3-[2-[3-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1CN1CCOCC1 TWPYVVZZLDOPKE-UHFFFAOYSA-N 0.000 claims 2
- HRCBKEBBMXSASN-UHFFFAOYSA-N n-[3-[2-[3-(piperidin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1CN1CCCCC1 HRCBKEBBMXSASN-UHFFFAOYSA-N 0.000 claims 2
- QQPOCQHJIBTSKM-UHFFFAOYSA-N n-[3-[2-[3-(pyrrolidin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1CN1CCCC1 QQPOCQHJIBTSKM-UHFFFAOYSA-N 0.000 claims 2
- FFSBKFBLCYIJHD-UHFFFAOYSA-N n-[3-[2-[3-(trifluoromethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C3N(CCCNC(=O)C=4SC=CC=4)C=CC3=CN=2)=C1 FFSBKFBLCYIJHD-UHFFFAOYSA-N 0.000 claims 2
- UFHRYOOCKSRQMN-UHFFFAOYSA-N n-[3-[2-[4-(1,2,4-triazol-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1N1C=NC=N1 UFHRYOOCKSRQMN-UHFFFAOYSA-N 0.000 claims 2
- XLGHMHOCMLFSOF-UHFFFAOYSA-N n-[3-[2-[4-(1,3-oxazol-5-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1C1=CN=CO1 XLGHMHOCMLFSOF-UHFFFAOYSA-N 0.000 claims 2
- HPCJOYKWJJEYJN-UHFFFAOYSA-N n-[3-[2-[4-(1-methylpiperidin-4-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCC1C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 HPCJOYKWJJEYJN-UHFFFAOYSA-N 0.000 claims 2
- RKNAYFKFLXRTJT-UHFFFAOYSA-N n-[3-[2-[4-(2-oxopyrrolidin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1N1CCCC1=O RKNAYFKFLXRTJT-UHFFFAOYSA-N 0.000 claims 2
- ANVBEYUNPJFCQV-UHFFFAOYSA-N n-[3-[2-[4-(4-cyano-1-methylpiperidin-4-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCC1(C#N)C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 ANVBEYUNPJFCQV-UHFFFAOYSA-N 0.000 claims 2
- IAQZCAABGCPKQD-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 IAQZCAABGCPKQD-UHFFFAOYSA-N 0.000 claims 2
- GPQFNIZBUXAFRW-UHFFFAOYSA-N n-[3-[2-[4-(morpholine-4-carbonyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1C(=O)N1CCOCC1 GPQFNIZBUXAFRW-UHFFFAOYSA-N 0.000 claims 2
- VPPQZQLLVNZCJA-UHFFFAOYSA-N n-[3-[2-[4-[(dimethylamino)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC(CN(C)C)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 VPPQZQLLVNZCJA-UHFFFAOYSA-N 0.000 claims 2
- CHXSKWJFRCPDDE-UHFFFAOYSA-N n-[3-[2-[4-[1-(2-fluoroethyl)piperidin-4-yl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(CCF)CCC1C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 CHXSKWJFRCPDDE-UHFFFAOYSA-N 0.000 claims 2
- LRUOLZVEZLNTGN-UHFFFAOYSA-N n-[3-[2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(=C1)C=NN1CCN1CCOCC1 LRUOLZVEZLNTGN-UHFFFAOYSA-N 0.000 claims 2
- DXCQLKJTTKRJSX-UHFFFAOYSA-N n-[3-[2-[[6-(4-methyl-1,4-diazepan-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 DXCQLKJTTKRJSX-UHFFFAOYSA-N 0.000 claims 2
- KRAPPMJTUWYDCP-UHFFFAOYSA-N n-[3-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 KRAPPMJTUWYDCP-UHFFFAOYSA-N 0.000 claims 2
- CTUNVQYSBNVSSI-UHFFFAOYSA-N n-[3-[5-bromo-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=C(Br)C3=CN=2)=C1 CTUNVQYSBNVSSI-UHFFFAOYSA-N 0.000 claims 2
- IGUYDWCLVZNKCN-UHFFFAOYSA-N n-[3-[5-chloro-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=C(Cl)C3=CN=2)=C1 IGUYDWCLVZNKCN-UHFFFAOYSA-N 0.000 claims 2
- JZGLWQPJZUIYAR-UHFFFAOYSA-N n-[3-[5-chloro-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C=4SC=CC=4)C=C(Cl)C3=CN=2)=C1 JZGLWQPJZUIYAR-UHFFFAOYSA-N 0.000 claims 2
- CFYXSQVZWRIGKJ-UHFFFAOYSA-N n-[3-[5-cyano-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=C(C3=CN=2)C#N)=C1 CFYXSQVZWRIGKJ-UHFFFAOYSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 claims 1
- UNWGHJICAJXZAG-UHFFFAOYSA-N 2-cyclopropyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]acetamide Chemical compound C1=CC2=CN=C(NC=3C=NC(=CC=3)N3CCOCC3)N=C2N1CCCNC(=O)CC1CC1 UNWGHJICAJXZAG-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- SIKXIUWKPGWBBF-UHFFFAOYSA-N 5-bromo-2,4-dichloropyrimidine Chemical compound ClC1=NC=C(Br)C(Cl)=N1 SIKXIUWKPGWBBF-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000025298 Alzheimer disease 15 Diseases 0.000 claims 1
- 208000012920 Alzheimer disease without neurofibrillary tangles Diseases 0.000 claims 1
- 208000032170 Congenital Abnormalities Diseases 0.000 claims 1
- 206010061619 Deformity Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VXJJQHRIKKTXEP-UHFFFAOYSA-N [(e)-2-ethoxyethenyl]tin Chemical compound CCO\C=C\[Sn] VXJJQHRIKKTXEP-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000003556 assay Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- IIHXGROJAPUAGM-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]oxolane-3-carboxamide Chemical compound C1COCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 IIHXGROJAPUAGM-UHFFFAOYSA-N 0.000 claims 1
- UIVUUYYWFTWMHH-UHFFFAOYSA-N n-[3-[5-chloro-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C12=NC(NC=3C=NC(=CC=3)N3CCOCC3)=NC=C2C(Cl)=CN1CCCNC(=O)C1CCC1 UIVUUYYWFTWMHH-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
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- 230000000069 prophylactic effect Effects 0.000 claims 1
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- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
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- 230000001225 therapeutic effect Effects 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| GB0903759.9 | 2009-03-04 | ||
| US16203209P | 2009-03-20 | 2009-03-20 | |
| US61/162,032 | 2009-03-20 | ||
| PCT/GB2010/000394 WO2010100431A1 (en) | 2009-03-04 | 2010-03-04 | Pyrrolopyrimidines used as kinase inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012143320A1 (en) | 2011-04-18 | 2012-10-26 | Cellzome Limited | (7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors |
| PL2714677T3 (pl) | 2011-05-23 | 2019-02-28 | Merck Patent Gmbh | Pochodne pirydynowe i pirazynowe |
| CN103596938B (zh) | 2011-05-23 | 2016-12-28 | 默克专利有限公司 | 噻唑衍生物 |
| GB201114051D0 (en) | 2011-08-15 | 2011-09-28 | Domainex Ltd | Compounds and their uses |
| DE102011112978A1 (de) | 2011-09-09 | 2013-03-14 | Merck Patent Gmbh | Benzonitrilderivate |
| WO2013041605A1 (en) | 2011-09-20 | 2013-03-28 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as kinase inhibitors |
| DE102011119127A1 (de) | 2011-11-22 | 2013-05-23 | Merck Patent Gmbh | 3-Cyanaryl-1H-pyrrolo[2.3-b]pyridin-Derivate |
| CN104093722B (zh) | 2012-02-09 | 2016-07-27 | 默克专利股份公司 | 作为TBK1和IKK抑制剂的呋喃并[3,2-b]-和噻吩并[3,2-b]吡啶衍生物 |
| US20170137426A1 (en) * | 2014-03-28 | 2017-05-18 | Changzhou Jiekai Pharmatech Co., Ltd. | Heterocyclic compounds as axl inhibitors |
| TW201613916A (en) | 2014-06-03 | 2016-04-16 | Gilead Sciences Inc | TANK-binding kinase inhibitor compounds |
| CN106715419A (zh) | 2014-09-26 | 2017-05-24 | 吉利德科学公司 | 用作tank‑结合激酶抑制剂化合物的氨基三嗪衍生物 |
| US10913744B2 (en) | 2015-02-13 | 2021-02-09 | Dana-Farber Cancer Institute, Inc. | LRRK2 inhibitors and methods of making and using the same |
| KR101663277B1 (ko) | 2015-03-30 | 2016-10-06 | 주식회사 녹십자 | TNIK, IKKε 및 TBK1 억제제로서의 피라졸계 유도체 및 이를 포함하는 약학적 조성물 |
| KR101660863B1 (ko) | 2015-04-03 | 2016-09-28 | 주식회사 녹십자 | IKKε 및 TBK1 억제제로서의 7-아자인돌 또는 4,7-다이아자인돌 유도체 및 이를 포함하는 약학적 조성물 |
| KR101846475B1 (ko) | 2015-04-27 | 2018-04-09 | 주식회사 녹십자 | TNIK, IKKε 및 TBK1 억제제로서의 화합물 및 이를 포함하는 약학적 조성물 |
| AU2016370916A1 (en) | 2015-12-17 | 2018-06-07 | Gilead Sciences, Inc. | Tank-binding kinase inhibitor compounds |
| DE102016113714A1 (de) | 2016-07-26 | 2018-02-01 | Rosa Karl | Transfektionsverfahren mit nicht-viralen Genliefersystemen |
| WO2019156438A1 (en) | 2018-02-07 | 2019-08-15 | Korea Research Institute Of Chemical Technology | Hetero ring-fused phenyl compounds for inhibiting tnik and medical uses thereof |
| CA3090233A1 (en) | 2018-02-07 | 2019-08-15 | Korea Research Institute Of Chemical Technology | Compounds for inhibiting tnik and medical uses thereof |
| CN112225742B (zh) * | 2020-12-11 | 2021-03-09 | 北京华氏开元医药科技有限公司 | 一种抑制vegfr活性的化合物、制备方法及应用 |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ207394A (en) | 1983-03-08 | 1987-03-06 | Commw Serum Lab Commission | Detecting or determining sequence of amino acids |
| GB9604361D0 (en) * | 1996-02-29 | 1996-05-01 | Pharmacia Spa | 4-Substituted pyrrolopyrimidine compounds as tyrosine kinase inhibitors |
| PL1713806T3 (pl) * | 2004-02-14 | 2013-09-30 | Irm Llc | Związki i kompozycje jako inhibitory kinaz białkowych |
| WO2005107760A1 (en) * | 2004-04-30 | 2005-11-17 | Irm Llc | Compounds and compositions as inducers of keratinocyte differentiation |
| JP2009506036A (ja) | 2005-08-24 | 2009-02-12 | レキシコン・ファーマシューティカルズ・インコーポレーテッド | ピロロピリジン、ピロロピリミジンおよびピラゾロピリジン化合物、それらを含む組成物、ならびにそれらの使用方法 |
| JO3235B1 (ar) * | 2006-05-26 | 2018-03-08 | Astex Therapeutics Ltd | مركبات بيررولوبيريميدين و استعمالاتها |
-
2009
- 2009-03-04 GB GBGB0903759.9A patent/GB0903759D0/en not_active Ceased
-
2010
- 2010-03-04 AU AU2010219466A patent/AU2010219466A1/en not_active Abandoned
- 2010-03-04 WO PCT/GB2010/000394 patent/WO2010100431A1/en not_active Ceased
- 2010-03-04 CA CA2753236A patent/CA2753236A1/en not_active Abandoned
- 2010-03-04 EP EP10707338.9A patent/EP2403853B1/en not_active Not-in-force
- 2010-03-04 US US13/254,355 patent/US20120088753A1/en not_active Abandoned
- 2010-03-04 CN CN2010800108001A patent/CN102341400A/zh active Pending
- 2010-03-04 JP JP2011552507A patent/JP2012519678A/ja not_active Withdrawn
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