JP2011507854A5 - - Google Patents
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- Publication number
- JP2011507854A5 JP2011507854A5 JP2010539504A JP2010539504A JP2011507854A5 JP 2011507854 A5 JP2011507854 A5 JP 2011507854A5 JP 2010539504 A JP2010539504 A JP 2010539504A JP 2010539504 A JP2010539504 A JP 2010539504A JP 2011507854 A5 JP2011507854 A5 JP 2011507854A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyridin
- pyridazin
- acetamide
- substituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 37
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- -1 compound salt Chemical class 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 24
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- YMDAQEULQVMMAG-UHFFFAOYSA-N n-[6-[6-chloro-5-[[4-[1-(methylamino)ethyl]phenyl]sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC(C(C)NC)=CC=C1S(=O)(=O)NC1=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=CN=C1Cl YMDAQEULQVMMAG-UHFFFAOYSA-N 0.000 claims 3
- 229940034982 antineoplastic agent Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 1
- KAGJYOMRCXMENF-UHFFFAOYSA-N 1-[6-(6-cyano-5-propan-2-yloxypyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]-3-(2-piperidin-1-ylethyl)urea Chemical compound N1=C(C#N)C(OC(C)C)=CC(C2=NN3C=C(NC(=O)NCCN4CCCCC4)N=C3C=C2)=C1 KAGJYOMRCXMENF-UHFFFAOYSA-N 0.000 claims 1
- BHHWPAVCSWIDJO-UHFFFAOYSA-N 1-[6-[6-chloro-5-(dimethylamino)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]-3-(2-piperidin-1-ylethyl)urea Chemical compound N1=C(Cl)C(N(C)C)=CC(C2=NN3C=C(NC(=O)NCCN4CCCCC4)N=C3C=C2)=C1 BHHWPAVCSWIDJO-UHFFFAOYSA-N 0.000 claims 1
- JZPZVXLZIFSSDS-UHFFFAOYSA-N 5-[2-amino-6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]imidazo[1,2-b]pyridazin-3-yl]-2-fluorobenzoic acid Chemical compound N1=C(Cl)C(NS(=O)(=O)C)=CC(C2=NN3C(C=4C=C(C(F)=CC=4)C(O)=O)=C(N)N=C3C=C2)=C1 JZPZVXLZIFSSDS-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 239000012830 cancer therapeutic Substances 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 229940125697 hormonal agent Drugs 0.000 claims 1
- 239000000677 immunologic agent Substances 0.000 claims 1
- 229940124541 immunological agent Drugs 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- ZYLGQXHDBGCALW-UHFFFAOYSA-N n-[5-(2-amino-3-pyridin-2-ylbenzimidazol-5-yl)-2-chloropyridin-3-yl]-4-fluorobenzenesulfonamide Chemical compound NC1=NC2=CC=C(C=3C=C(NS(=O)(=O)C=4C=CC(F)=CC=4)C(Cl)=NC=3)C=C2N1C1=CC=CC=N1 ZYLGQXHDBGCALW-UHFFFAOYSA-N 0.000 claims 1
- LENBBFNKOZJFQK-UHFFFAOYSA-N n-[5-(2-amino-3-pyridin-4-ylimidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl]methanesulfonamide Chemical compound N1=C(Cl)C(NS(=O)(=O)C)=CC(C2=NN3C(C=4C=CN=CC=4)=C(N)N=C3C=C2)=C1 LENBBFNKOZJFQK-UHFFFAOYSA-N 0.000 claims 1
- ABCZKUIDXGHMIH-UHFFFAOYSA-N n-[5-(2-aminoimidazo[1,2-a]pyridin-6-yl)-2-chloropyridin-3-yl]-4-fluorobenzenesulfonamide Chemical compound C1=CC2=NC(N)=CN2C=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 ABCZKUIDXGHMIH-UHFFFAOYSA-N 0.000 claims 1
- FPJNXVCSICMXRJ-UHFFFAOYSA-N n-[5-(2-aminoimidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl]-4-fluorobenzenesulfonamide Chemical compound C1=CC2=NC(N)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 FPJNXVCSICMXRJ-UHFFFAOYSA-N 0.000 claims 1
- CTRIVXOXDTZPIE-UHFFFAOYSA-N n-[5-(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=1)=CN=CC=1C(N1N=2)=NN=C1C=CC=2C1=CC=CC=C1 CTRIVXOXDTZPIE-UHFFFAOYSA-N 0.000 claims 1
- GOCCRGWDVWVMNU-UHFFFAOYSA-N n-[5-[2-amino-3-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazin-6-yl]-2-chloropyridin-3-yl]-3-(difluoromethoxy)benzenesulfonamide Chemical compound C1=NC(C)=CC(C=2N3N=C(C=CC3=NC=2N)C=2C=C(NS(=O)(=O)C=3C=C(OC(F)F)C=CC=3)C(Cl)=NC=2)=C1 GOCCRGWDVWVMNU-UHFFFAOYSA-N 0.000 claims 1
- UEFWWWBAPHUGMF-UHFFFAOYSA-N n-[5-[2-amino-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]-2-chloropyridin-3-yl]methanesulfonamide Chemical compound N1=C(Cl)C(NS(=O)(=O)C)=CC(C2=NN3C(C=4C=C(F)C=CC=4)=C(N)N=C3C=C2)=C1 UEFWWWBAPHUGMF-UHFFFAOYSA-N 0.000 claims 1
- VTQHLGNTFCRBJH-UHFFFAOYSA-N n-[6-(2-fluoropyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C1=CC=NC(F)=C1 VTQHLGNTFCRBJH-UHFFFAOYSA-N 0.000 claims 1
- GVQACZSEGZYBKO-UHFFFAOYSA-N n-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN2C=C(NC(C)=O)N=C2C=C1 GVQACZSEGZYBKO-UHFFFAOYSA-N 0.000 claims 1
- LEXVFSSQSRHCDF-UHFFFAOYSA-N n-[6-(3-methylsulfanylphenyl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CSC1=CC=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=C1 LEXVFSSQSRHCDF-UHFFFAOYSA-N 0.000 claims 1
- XWJGCEJHQFOLQE-UHFFFAOYSA-N n-[6-(5,6-dimethoxypyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound N1=C(OC)C(OC)=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=C1 XWJGCEJHQFOLQE-UHFFFAOYSA-N 0.000 claims 1
- WPDUKUOHEYEXSQ-UHFFFAOYSA-N n-[6-(5-methylsulfanylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CSC1=CN=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=C1 WPDUKUOHEYEXSQ-UHFFFAOYSA-N 0.000 claims 1
- QJCLRSIPLYBASE-UHFFFAOYSA-N n-[6-(5-methylsulfonylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C1=CN=CC(S(C)(=O)=O)=C1 QJCLRSIPLYBASE-UHFFFAOYSA-N 0.000 claims 1
- MVJUDIWGLAFUEU-UHFFFAOYSA-N n-[6-[2-(2-fluorophenyl)sulfanylpyridin-4-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CC=NC=1SC1=CC=CC=C1F MVJUDIWGLAFUEU-UHFFFAOYSA-N 0.000 claims 1
- TXKYOSTZYAABSD-UHFFFAOYSA-N n-[6-[3-(isoquinolin-5-ylsulfonylamino)phenyl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound N1=CC=C2C(S(=O)(=O)NC=3C=CC=C(C=3)C3=NN4C=C(N=C4C=C3)NC(=O)C)=CC=CC2=C1 TXKYOSTZYAABSD-UHFFFAOYSA-N 0.000 claims 1
- VDCDQHDSIGFSEK-UHFFFAOYSA-N n-[6-[3-(naphthalen-1-ylsulfonylamino)phenyl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC=C2C(S(=O)(=O)NC=3C=CC=C(C=3)C3=NN4C=C(N=C4C=C3)NC(=O)C)=CC=CC2=C1 VDCDQHDSIGFSEK-UHFFFAOYSA-N 0.000 claims 1
- WQJAPCZXLCHGEO-UHFFFAOYSA-N n-[6-[3-[(4-methylphenyl)sulfonylamino]phenyl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 WQJAPCZXLCHGEO-UHFFFAOYSA-N 0.000 claims 1
- QZXWQIUHLLWMMU-UHFFFAOYSA-N n-[6-[3-[methyl-(4-methylphenyl)sulfonylamino]phenyl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C=1C=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=CC=1N(C)S(=O)(=O)C1=CC=C(C)C=C1 QZXWQIUHLLWMMU-UHFFFAOYSA-N 0.000 claims 1
- OBOFGDDXBXEDIK-UHFFFAOYSA-N n-[6-[5-(dimethylamino)-6-(2-morpholin-4-ylethoxy)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CN(C)C1=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=CN=C1OCCN1CCOCC1 OBOFGDDXBXEDIK-UHFFFAOYSA-N 0.000 claims 1
- CWCUFSAPQCMYEG-UHFFFAOYSA-N n-[6-[5-(dimethylamino)-6-(2-morpholin-4-ylethylamino)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CN(C)C1=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=CN=C1NCCN1CCOCC1 CWCUFSAPQCMYEG-UHFFFAOYSA-N 0.000 claims 1
- JDLFNYFQVDBZGX-UHFFFAOYSA-N n-[6-[5-(propan-2-ylamino)-6-(trifluoromethyl)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound N1=C(C(F)(F)F)C(NC(C)C)=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=C1 JDLFNYFQVDBZGX-UHFFFAOYSA-N 0.000 claims 1
- PMLPEKOZYDGQFG-UHFFFAOYSA-N n-[6-[5-[(4-methylphenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-a]pyrazin-2-yl]acetamide Chemical compound N1=CC2=NC(NC(=O)C)=CN2C=C1C(C=1)=CN=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 PMLPEKOZYDGQFG-UHFFFAOYSA-N 0.000 claims 1
- GBQNMMOBKMRTOR-UHFFFAOYSA-N n-[6-[5-[(4-tert-butylphenyl)sulfonylamino]-6-chloropyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GBQNMMOBKMRTOR-UHFFFAOYSA-N 0.000 claims 1
- BLJRCNSXJLQTSS-UHFFFAOYSA-N n-[6-[5-[(4-tert-butylphenyl)sulfonylamino]-6-cyanopyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(C#N)C=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 BLJRCNSXJLQTSS-UHFFFAOYSA-N 0.000 claims 1
- KBFJYZWCROOHAH-UHFFFAOYSA-N n-[6-[5-[(4-tert-butylphenyl)sulfonylamino]-6-ethynylpyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(C#C)C=1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 KBFJYZWCROOHAH-UHFFFAOYSA-N 0.000 claims 1
- QDHDUMVPCAHHSF-UHFFFAOYSA-N n-[6-[6-(2-morpholin-4-ylethylamino)-5-(propan-2-ylamino)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(C)NC1=CC(C2=NN3C=C(NC(C)=O)N=C3C=C2)=CN=C1NCCN1CCOCC1 QDHDUMVPCAHHSF-UHFFFAOYSA-N 0.000 claims 1
- UHQWQCNMMZGHRC-UHFFFAOYSA-N n-[6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(C)(=O)=O)C(Cl)=NC=3)=NN2C=1C1=CC=CC(F)=C1 UHQWQCNMMZGHRC-UHFFFAOYSA-N 0.000 claims 1
- KMGQPMVTRBAPMV-UHFFFAOYSA-N n-[6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-3-[4-fluoro-3-(morpholine-4-carbonyl)phenyl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(C)(=O)=O)C(Cl)=NC=3)=NN2C=1C(C=1)=CC=C(F)C=1C(=O)N1CCOCC1 KMGQPMVTRBAPMV-UHFFFAOYSA-N 0.000 claims 1
- ZHWOTURMYYTCTB-UHFFFAOYSA-N n-[6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-3-iodoimidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound N=1N2C(I)=C(NC(=O)C)N=C2C=CC=1C1=CN=C(Cl)C(NS(C)(=O)=O)=C1 ZHWOTURMYYTCTB-UHFFFAOYSA-N 0.000 claims 1
- MQVPAFLDNHSDEI-UHFFFAOYSA-N n-[6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-3-pyridin-4-ylimidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(C)(=O)=O)C(Cl)=NC=3)=NN2C=1C1=CC=NC=C1 MQVPAFLDNHSDEI-UHFFFAOYSA-N 0.000 claims 1
- XJUQIECUCFGNSA-UHFFFAOYSA-N n-[6-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C1=CN=C(Cl)C(NS(C)(=O)=O)=C1 XJUQIECUCFGNSA-UHFFFAOYSA-N 0.000 claims 1
- UCXPQJNZIRTUGH-UHFFFAOYSA-N n-[6-[6-chloro-5-(morpholin-4-ylsulfonylamino)pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)N1CCOCC1 UCXPQJNZIRTUGH-UHFFFAOYSA-N 0.000 claims 1
- HQMYZUNEFNTEQE-UHFFFAOYSA-N n-[6-[6-chloro-5-[(2-chloro-4-fluorophenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1Cl HQMYZUNEFNTEQE-UHFFFAOYSA-N 0.000 claims 1
- XUVGYKGUURQNNP-UHFFFAOYSA-N n-[6-[6-chloro-5-[(2-chloro-6-methylphenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=C(C)C=CC=C1Cl XUVGYKGUURQNNP-UHFFFAOYSA-N 0.000 claims 1
- SASGTCBMHBJCIK-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridazin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(N=NC=1Cl)=CC=1NS(=O)(=O)C1=CC=C(F)C=C1 SASGTCBMHBJCIK-UHFFFAOYSA-N 0.000 claims 1
- IDAXZUXBOFQTMN-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1-pyridin-2-ylbenzimidazol-2-yl]acetamide Chemical compound CC(=O)NC1=NC2=CC=C(C=3C=C(NS(=O)(=O)C=4C=CC(F)=CC=4)C(Cl)=NC=3)C=C2N1C1=CC=CC=N1 IDAXZUXBOFQTMN-UHFFFAOYSA-N 0.000 claims 1
- VMOWYZQEUZXDFM-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1h-benzimidazol-2-yl]acetamide Chemical compound C=1C=C2NC(NC(=O)C)=NC2=CC=1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 VMOWYZQEUZXDFM-UHFFFAOYSA-N 0.000 claims 1
- WHKSVDCLCLYVSX-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-3-pyridin-4-ylimidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(=O)(=O)C=4C=CC(F)=CC=4)C(Cl)=NC=3)=NN2C=1C1=CC=NC=C1 WHKSVDCLCLYVSX-UHFFFAOYSA-N 0.000 claims 1
- XNIJHVMYDIVRJQ-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-a]pyridin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2C=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 XNIJHVMYDIVRJQ-UHFFFAOYSA-N 0.000 claims 1
- FHOXICOTPQTJOQ-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 FHOXICOTPQTJOQ-UHFFFAOYSA-N 0.000 claims 1
- HYAVDBLWDKUYEK-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-methylphenyl)sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(C)C=C1 HYAVDBLWDKUYEK-UHFFFAOYSA-N 0.000 claims 1
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- HNFKWAKUAQTMRW-UHFFFAOYSA-N n-[6-[6-chloro-5-[[3-(difluoromethoxy)phenyl]sulfonylamino]pyridin-3-yl]-3-pyridin-3-ylimidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(=O)(=O)C=4C=C(OC(F)F)C=CC=4)C(Cl)=NC=3)=NN2C=1C1=CC=CN=C1 HNFKWAKUAQTMRW-UHFFFAOYSA-N 0.000 claims 1
- GTMAIZIZTDUMKQ-UHFFFAOYSA-N n-[6-[6-chloro-5-[[3-(difluoromethoxy)phenyl]sulfonylamino]pyridin-3-yl]-3-pyridin-4-ylimidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound CC(=O)NC=1N=C2C=CC(C=3C=C(NS(=O)(=O)C=4C=C(OC(F)F)C=CC=4)C(Cl)=NC=3)=NN2C=1C1=CC=NC=C1 GTMAIZIZTDUMKQ-UHFFFAOYSA-N 0.000 claims 1
- YHCSXAXEVJMGJD-UHFFFAOYSA-N n-[6-[6-chloro-5-[[3-(difluoromethoxy)phenyl]sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=CC(OC(F)F)=C1 YHCSXAXEVJMGJD-UHFFFAOYSA-N 0.000 claims 1
- MUWXXVHFJQHSBQ-UHFFFAOYSA-N n-[6-[6-chloro-5-[[4-(2-hydroxypropan-2-yl)phenyl]sulfonylamino]pyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl]acetamide Chemical compound C1=CC2=NC(NC(=O)C)=CN2N=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(C(C)(C)O)C=C1 MUWXXVHFJQHSBQ-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (107)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2555263A1 (en) * | 2004-02-12 | 2005-09-01 | Neurogen Corporation | Imidazo-pyridazines, triazolo-pyridazines and related benzodiazepine receptor ligands |
| WO2009018657A1 (en) | 2007-08-03 | 2009-02-12 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US8431608B2 (en) | 2007-08-17 | 2013-04-30 | Icagen Inc. | Heterocycles as potassium channel modulators |
| CA2696631A1 (en) * | 2007-08-17 | 2009-02-26 | Icagen, Inc. | Heterocycles as potassium channel modulators |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| US20110105457A1 (en) * | 2008-04-18 | 2011-05-05 | Shionogi & Co., Ltd. | Heterocyclic compound having inhibitory activity on pi3k |
| WO2009133127A1 (en) * | 2008-04-30 | 2009-11-05 | Merck Serono S.A. | Fused bicyclic compounds and use thereof as pi3k inhibitors |
| JP5599783B2 (ja) * | 2008-05-30 | 2014-10-01 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| WO2010007099A1 (en) * | 2008-07-15 | 2010-01-21 | Cellzome Limited | 2-aminoimidazo[1,2-b]pyridazine derivatives as pi3k inhibitors |
| TWI378933B (en) | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| CA2755285C (en) | 2009-03-20 | 2014-02-11 | Yunxin Y. Bo | Inhibitors of pi3 kinase |
| CA2760778A1 (en) * | 2009-05-13 | 2010-11-18 | Amgen Inc. | Heteroaryl compounds as pikk inhibitors |
| ES2459468T3 (es) | 2009-05-15 | 2014-05-09 | Novartis Ag | Arilpiridinas como inhibidores de aldosterona sintasa |
| EP2448938B9 (en) | 2009-06-29 | 2015-06-10 | Incyte Corporation | Pyrimidinones as pi3k inhibitors |
| WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| US20130131057A1 (en) | 2010-05-13 | 2013-05-23 | Centro Nacional De Investigaciones Oncologicas (Cnio | New bicyclic compounds as pi3-k and mtor inhibitors |
| JO2998B1 (ar) | 2010-06-04 | 2016-09-05 | Amgen Inc | مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان |
| US8440662B2 (en) | 2010-10-31 | 2013-05-14 | Endo Pharmaceuticals, Inc. | Substituted quinazoline and pyrido-pyrimidine derivatives |
| JP5961187B2 (ja) | 2010-12-20 | 2016-08-02 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉ３ｋ阻害剤としてのｎ−（１−（置換フェニル）エチル）−９ｈ−プリン−６−アミン |
| CN103501610A (zh) * | 2011-03-09 | 2014-01-08 | 西建阿维拉米斯研究公司 | Pi3激酶抑制剂和其用途 |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| WO2012174312A2 (en) * | 2011-06-15 | 2012-12-20 | Glaxosmithkline Llc | Benzimidazole derivatives as antiviral agents |
| MX389479B (es) | 2011-09-02 | 2025-03-20 | Incyte Holdings Corp | Heterociclilaminas como inhibidores de fosfoinositida 3-cinasas (pi3k) |
| MX352672B (es) | 2011-09-27 | 2017-12-04 | Amgen Inc | Compuestos heterocíclicos como inhibidores de mdm2 para el tratamiento del cáncer. |
| US10292390B2 (en) | 2011-11-04 | 2019-05-21 | Wisconsin Alumni Research Foundation | Inhibition and dispersion of bacterial biofilms with 2-aminobenzimidazole derivatives |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| TWI574962B (zh) * | 2012-11-14 | 2017-03-21 | 加拓科學公司 | 作爲ｐｉ３激酶調節劑的芳雜環化合物及其使用方法和用途 |
| EP2935272B1 (en) | 2012-12-21 | 2017-02-22 | Bristol-Myers Squibb Company | Pyrazole substituted imidazopyrazines as casein kinase 1 d/e inhibitors |
| JP6267231B2 (ja) | 2012-12-21 | 2018-01-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | カゼインキナーゼ１δ／ε阻害剤としての新規な置換イミダゾール |
| CN103965199B (zh) * | 2013-02-02 | 2017-07-07 | 广东东阳光药业有限公司 | 一种芳杂环化合物、包含它的药物组合物及其用途 |
| US20160002185A1 (en) | 2013-02-19 | 2016-01-07 | Amgen Inc. | Cis-morpholinone and other compounds as mdm2 inhibitors for the treatment of cancer |
| KR102148681B1 (ko) * | 2013-02-21 | 2020-08-27 | 칼리토르 사이언시즈, 엘엘씨 | Pi3 키나제 모듈레이터로서의 헤테로방향족 화합물 |
| WO2014151863A1 (en) | 2013-03-14 | 2014-09-25 | Amgen Inc. | Heteroaryl acid morpholinone compounds as mdm2 inhibitors for the treatment of cancer |
| WO2014145852A2 (en) | 2013-03-15 | 2014-09-18 | Knopp Biosciences Llc | Imidazo(4,5-b) pyridin-2-yl amides as kv7 channel activators |
| MA53572A1 (fr) | 2013-06-10 | 2021-10-29 | Amgen Inc | Procédés de production et formes cristallines d'un inhibiteur mdm2 |
| MY192088A (en) | 2013-11-11 | 2022-07-26 | Amgen Inc | Combinantion therapy including an mdm2 inhibitor and one or more additional pharmaceutically active agents for the treatment of cancers |
| GB201321734D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| WO2015108881A1 (en) | 2014-01-14 | 2015-07-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| TN2016000270A1 (en) | 2014-01-14 | 2017-10-06 | Millennium Pharm Inc | Heteroaryls and uses thereof. |
| LT3105218T (lt) | 2014-02-13 | 2019-12-10 | Incyte Corp | Ciklopropilaminai kaip lsd1 inhibitoriai |
| EP3392244A1 (en) | 2014-02-13 | 2018-10-24 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| WO2015123424A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| WO2015134854A2 (en) * | 2014-03-06 | 2015-09-11 | Oyagen, Inc. | Small molecule vif dimerization antagonists as anti-hiv agents and for use as hiv/aids therapeutics |
| US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007736A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyrazines as lsd1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| ES2749103T3 (es) | 2014-09-12 | 2020-03-19 | Knopp Biosciences Llc | Benzoimidazol-1,2-ilamidas como activadores del canal Kv7 |
| CN105503877A (zh) | 2014-09-24 | 2016-04-20 | 和记黄埔医药（上海）有限公司 | 咪唑并哒嗪类化合物及其用途 |
| CN104447756A (zh) * | 2014-11-10 | 2015-03-25 | 常州大学 | 一种五氟磺草胺中间体的制备方法 |
| CN104402890A (zh) * | 2014-11-10 | 2015-03-11 | 常州大学 | 一种制备五氟磺草胺的方法 |
| EP3259264B1 (en) | 2015-02-20 | 2022-07-27 | Rigel Pharmaceuticals, Inc. | Gdf-8 inhibitors |
| SG10201912302VA (en) | 2015-02-27 | 2020-02-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| EA201792205A1 (ru) | 2015-04-03 | 2018-02-28 | Инсайт Корпорейшн | Гетероциклические соединения как ингибиторы lsd1 |
| WO2016183060A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| MA42145B1 (fr) | 2015-05-20 | 2020-05-29 | Amgen Inc | Triazoles agonistes du récepteur apj |
| DK3334709T3 (da) | 2015-08-12 | 2025-02-03 | Incyte Holdings Corp | Salte af en lsd1-hæmmer |
| AU2016315881B2 (en) * | 2015-09-03 | 2019-09-19 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK1A and uses thereof |
| CA3021678A1 (en) | 2016-04-22 | 2017-10-26 | Incyte Corporation | Formulations of an lsd1 inhibitor |
| EP3452466B1 (en) | 2016-05-03 | 2020-08-12 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| EP3541802B1 (en) | 2016-11-16 | 2025-01-01 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| UA127968C2 (uk) | 2017-05-22 | 2024-02-28 | Емджен Інк. | Інгібітори g12c kras і способи їх застосування |
| WO2019018562A1 (en) | 2017-07-19 | 2019-01-24 | Ideaya Biosciences, Inc. | AMIDO COMPOUND AS MODULATORS OF AHR |
| US10640504B2 (en) | 2017-09-08 | 2020-05-05 | Amgen Inc. | Inhibitors of KRAS G12C and methods of using the same |
| CN111566103B (zh) * | 2017-10-30 | 2023-06-23 | 百时美施贵宝公司 | 作为激酶抑制剂的氨基咪唑并吡嗪 |
| WO2019089335A1 (en) | 2017-11-03 | 2019-05-09 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| AU2019227607C1 (en) | 2018-02-27 | 2023-07-20 | Incyte Corporation | Imidazopyrimidines and triazolopyrimidines as A2A / A2B inhibitors |
| CN119118926A (zh) | 2018-03-19 | 2024-12-13 | 诺普生物科学有限责任公司 | Kv7通道激活剂组合物和使用方法 |
| EP3788037A1 (en) | 2018-05-01 | 2021-03-10 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| MX2020010836A (es) | 2018-05-04 | 2021-01-08 | Amgen Inc | Inhibidores de kras g12c y métodos para su uso. |
| EP3810610A1 (en) | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| IL278889B2 (en) | 2018-06-01 | 2025-11-01 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
| AU2019284472B2 (en) | 2018-06-11 | 2024-05-30 | Amgen Inc. | KRAS G12C inhibitors for treating cancer |
| JP7369719B2 (ja) | 2018-06-12 | 2023-10-26 | アムジエン・インコーポレーテツド | ＫＲａｓ Ｇ１２Ｃ阻害剤及びそれを使用する方法 |
| CN117304191A (zh) | 2018-07-05 | 2023-12-29 | 因赛特公司 | 作为a2a/a2b抑制剂的稠合吡嗪衍生物 |
| CA3110525A1 (en) | 2018-08-31 | 2020-03-05 | Amgen, Inc. | Processes for preparing a mdm2 inhibitor |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| JP2022521537A (ja) * | 2019-02-22 | 2022-04-08 | ファースト・バイオセラピューティクス・インコーポレイテッド | イミダゾピリジニル化合物及び増殖性障害の処置のためのその使用 |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| US11919904B2 (en) | 2019-03-29 | 2024-03-05 | Incyte Corporation | Sulfonylamide compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| EP3972973A1 (en) | 2019-05-21 | 2022-03-30 | Amgen Inc. | Solid state forms |
| WO2021030537A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| CR20220170A (es) | 2019-10-11 | 2022-10-10 | Incyte Corp | Aminas bicíclicas como inhibidoras de la cdk2 |
| US20240139193A1 (en) | 2019-10-15 | 2024-05-02 | Amgen Inc. | Combination therapy of kras inhibitor and shp2 inhibitor for treatment of cancers |
| US20230028414A1 (en) | 2019-12-16 | 2023-01-26 | Amgen Inc. | Dosing regimen of kras g12c inhibitor |
| CN112047950B (zh) * | 2020-09-14 | 2023-07-25 | 华东师范大学 | 咪唑并吡嗪类衍生物及其合成方法和应用 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN120887867B (zh) * | 2025-07-10 | 2026-05-15 | 浙江中医药大学 | 一类喹啉联芳杂环pi3k/hdac双靶点小分子抑制剂及其应用 |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH505543A (de) * | 1968-11-01 | 1971-04-15 | Ciba Geigy Ag | Schädlingsbekämpfungsmittel |
| AUPP873799A0 (en) * | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| PL357099A1 (en) * | 2000-02-07 | 2004-07-12 | Abbott Gmbh & Co.Kg | 2-benzothiazolyl urea derivatives and their use as protein kinase inhibitors |
| AU5261001A (en) * | 2000-04-27 | 2001-11-12 | Imperial Cancer Research Technology Ltd | Condensed heteroaryl derivatives |
| US7449488B2 (en) * | 2002-06-04 | 2008-11-11 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| MXPA05000453A (es) | 2002-07-10 | 2005-03-23 | Applied Research Systems | Derivados de benceno fusionados a azolidinona-vinilo. |
| GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| AR042956A1 (es) * | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| WO2004098494A2 (en) | 2003-04-30 | 2004-11-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| GB0315203D0 (en) | 2003-06-28 | 2003-08-06 | Celltech R&D Ltd | Chemical compounds |
| US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| US7470712B2 (en) | 2004-01-21 | 2008-12-30 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors |
| US7863310B2 (en) * | 2004-02-03 | 2011-01-04 | Eli Lilly And Company | Kinase inhibitors |
| WO2005076854A2 (en) * | 2004-02-04 | 2005-08-25 | Smithkline Beecham Corporation | Pyrimidinone compounds useful as kinase inhibitors |
| US20070054916A1 (en) | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| MX2007004302A (es) | 2004-10-12 | 2007-06-07 | Applied Research Systems | Inhibidores de pi3 cinasa gamma para el tratamiento de anemia. |
| HN2005000795A (es) | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| DE602005023763D1 (de) * | 2004-11-04 | 2010-11-04 | Vertex Pharma | Als inhibitoren von proteinkinasen geeignete pyrazoloä1,5-aüpyrimidine |
| SE0402735D0 (sv) | 2004-11-09 | 2004-11-09 | Astrazeneca Ab | Novel compounds |
| US7473784B2 (en) | 2005-08-01 | 2009-01-06 | Bristol-Myers Squibb Company | Benzothiazole and azabenzothiazole compounds useful as kinase inhibitors |
| ES2274712B1 (es) * | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| US7989461B2 (en) | 2005-12-23 | 2011-08-02 | Amgen Inc. | Substituted quinazolinamine compounds for the treatment of cancer |
| PE20070978A1 (es) * | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| JP2009535386A (ja) | 2006-05-03 | 2009-10-01 | アストラゼネカ アクチボラグ | チアゾール誘導体および抗腫瘍剤としてのその使用 |
| US20090118336A1 (en) | 2006-05-03 | 2009-05-07 | Laurent David | Pyrazole derivatives and their use as pi3k inhibitors |
| GB0608820D0 (en) | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| WO2007135398A1 (en) | 2006-05-22 | 2007-11-29 | Astrazeneca Ab | Indole derivatives |
| GB0610242D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| FR2903107B1 (fr) * | 2006-07-03 | 2008-08-22 | Sanofi Aventis Sa | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| PT2049502E (pt) | 2006-07-28 | 2012-04-02 | Novartis Ag | Quinazolinas 2,4-substituídas como inibidores da lípido cinase |
| EP2058309A4 (en) * | 2006-08-04 | 2010-12-22 | Takeda Pharmaceutical | CONDENSED HETEROCYCLIC COMPOUND |
| JP5336375B2 (ja) * | 2006-08-30 | 2013-11-06 | セルゾーム リミテッド | キナーゼ阻害剤としてのトリアゾール誘導体 |
| JP2010504933A (ja) | 2006-09-29 | 2010-02-18 | ノバルティス アーゲー | Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン |
| US20090318410A1 (en) | 2006-10-30 | 2009-12-24 | Novartis Ag | Imidazopyridazines as lipid kinase inhibitors |
| PE20081679A1 (es) | 2006-12-07 | 2008-12-18 | Hoffmann La Roche | Compuestos del inhibidor de fosfoinositida 3-cinasa y metodos de uso |
| CA2671845C (en) | 2006-12-07 | 2015-03-24 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| ZA200904857B (en) | 2007-02-22 | 2010-09-29 | Merck Serono Sa | Quinoxaline compounds and use thereof |
| US20080233127A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| US20080234262A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| WO2008133192A1 (ja) | 2007-04-19 | 2008-11-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| EP2155753A1 (en) | 2007-05-09 | 2010-02-24 | Novartis Ag | Substituted imidazopyridazines as pi3k lipid kinase inhibitors |
| TW200902008A (en) | 2007-05-10 | 2009-01-16 | Smithkline Beecham Corp | Quinoxaline derivatives as PI3 kinase inhibitors |
| AR067326A1 (es) | 2007-05-11 | 2009-10-07 | Novartis Ag | Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| US8131310B2 (en) | 2007-05-18 | 2012-03-06 | Research In Motion Limited | Method and system for discontinuous reception de-synchronization detection |
| EP2154965A4 (en) | 2007-05-29 | 2011-08-17 | Glaxosmithkline Llc | NAPHTHYRIDINE DERIVATIVES AS P13 KINASE INHIBITORS |
| WO2008152394A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Pharmaceutical compounds |
| WO2008152387A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Quinazoline derivatives as pi3 kinase inhibitors |
| ATE510841T1 (de) | 2007-06-12 | 2011-06-15 | Hoffmann La Roche | Thiazoliopyrimidine und ihre verwendung als hemmer der phosphatidylinositol-3 kinase |
| UY31137A1 (es) | 2007-06-14 | 2009-01-05 | Smithkline Beecham Corp | Derivados de quinazolina como inhibidores de la pi3 quinasa |
| JP5588339B2 (ja) | 2007-06-25 | 2014-09-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規化学化合物 |
| US20100226881A1 (en) | 2007-07-11 | 2010-09-09 | Auckland Uniservices Limited | PYRAZOLO[1,5-a]PYRIDINES AND THEIR USE IN CANCER THERAPY |
| CN101801966A (zh) | 2007-07-18 | 2010-08-11 | 诺瓦提斯公司 | 双环杂芳基化合物和它们作为激酶抑制剂的用途 |
| US7928140B2 (en) | 2007-08-02 | 2011-04-19 | Amgen Inc. | Benzothiazole PI3 kinase modulators for cancer treatment |
| US8129371B2 (en) | 2007-10-16 | 2012-03-06 | Wyeth Llc | Thienopyrimidine and pyrazolopyrimidine compounds and their use as mTOR kinase and PI3 kinase inhibitors |
| JP2011500823A (ja) | 2007-10-22 | 2011-01-06 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害物質としてのピリドスルホンアミド誘導体 |
| GB0721095D0 (en) | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| JP5638955B2 (ja) | 2007-10-26 | 2014-12-10 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｐｉ３キナーゼ阻害剤として有用なプリン誘導体 |
| UA102828C2 (en) | 2007-11-27 | 2013-08-27 | Целльзом Лимитед | Amino triazoles as p13k inhibitors |
| US20090149458A1 (en) | 2007-11-27 | 2009-06-11 | Wyeth | PYRROLO[3,2-d]PYRIMIDINE COMPOUNDS AND THEIR USE AS PI3 KINASE AND mTOR KINASE INHIBITORS |
| WO2009081105A2 (en) | 2007-12-21 | 2009-07-02 | Ucb Pharma S.A. | Quinoxaline and quinoline derivatives as kinase inhibitors |
| MX2010007746A (es) | 2008-01-15 | 2010-08-18 | Wyeth Llc | Compuestos de 3h-[1,2,3]triazolo[4,5-d]pirimidina, su uso como inhibidores de diana de rapamicina de mamifero quinasa y fosfatidilinositol quinasa y su sintesis. |
| JP5608099B2 (ja) | 2008-01-30 | 2014-10-15 | ジェネンテック， インコーポレイテッド | ピラゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 |
| US20090192176A1 (en) | 2008-01-30 | 2009-07-30 | Wyeth | 1H-PYRAZOLO[3,4-D]PYRIMIDINE, PURINE, 7H-PURIN-8(9H)-ONE, 3H-[1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE, AND THIENO[3,2-D]PYRIMIDINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES |
-
2008
- 2008-12-18 US US12/317,166 patent/US7820665B2/en active Active
- 2008-12-18 WO PCT/US2008/013940 patent/WO2009085230A1/en not_active Ceased
- 2008-12-18 PE PE2008002118A patent/PE20091268A1/es not_active Application Discontinuation
- 2008-12-18 JP JP2010539504A patent/JP5520831B2/ja not_active Expired - Fee Related
- 2008-12-18 EP EP08867948A patent/EP2231661A1/en not_active Withdrawn
- 2008-12-18 CA CA2710194A patent/CA2710194C/en not_active Expired - Fee Related
- 2008-12-18 AU AU2008343813A patent/AU2008343813B2/en not_active Ceased
- 2008-12-18 CL CL2008003798A patent/CL2008003798A1/es unknown
- 2008-12-19 AR ARP080105607A patent/AR069862A1/es not_active Application Discontinuation
- 2008-12-19 TW TW097149904A patent/TW200940544A/zh unknown
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