RU2018104702A - Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ - Google Patents
Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ Download PDFInfo
- Publication number
- RU2018104702A RU2018104702A RU2018104702A RU2018104702A RU2018104702A RU 2018104702 A RU2018104702 A RU 2018104702A RU 2018104702 A RU2018104702 A RU 2018104702A RU 2018104702 A RU2018104702 A RU 2018104702A RU 2018104702 A RU2018104702 A RU 2018104702A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- alkyl
- hydrogen
- amino
- pyrrolo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 35
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 58
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 8
- -1 hydroxy, methoxy Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 230000035755 proliferation Effects 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 4
- 206010013774 Dry eye Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- UOFYSRZSLXWIQB-UHFFFAOYSA-N abivertinib Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2)C2=N1 UOFYSRZSLXWIQB-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000003840 hydrochlorides Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- IQVPLUKZZPRFMX-UHFFFAOYSA-N C(C=C)(=O)NC1=CC(=CC=C1)OC=1C2=C(N=C(N=1)NC1=CC=C(C=C1)N1CCN(CC1)C)NCC2(N1CCCC1)CCO Chemical compound C(C=C)(=O)NC1=CC(=CC=C1)OC=1C2=C(N=C(N=1)NC1=CC=C(C=C1)N1CCN(CC1)C)NCC2(N1CCCC1)CCO IQVPLUKZZPRFMX-UHFFFAOYSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas 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
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- UTDDJJUGDRITRM-UHFFFAOYSA-N n-[3-[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7-(hydroxymethyl)pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2CO)C2=N1 UTDDJJUGDRITRM-UHFFFAOYSA-N 0.000 claims 1
- DCGRPOGHWQLKOZ-UHFFFAOYSA-N n-[3-[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7-methylsulfonylpyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2S(C)(=O)=O)C2=N1 DCGRPOGHWQLKOZ-UHFFFAOYSA-N 0.000 claims 1
- CRQWCDVENQWZCN-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]-7-methylsulfonylpyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2S(C)(=O)=O)C2=N1 CRQWCDVENQWZCN-UHFFFAOYSA-N 0.000 claims 1
- HFYLURUSCWSASY-UHFFFAOYSA-N n-[3-[7-(2-fluoroethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2CCF)C2=N1 HFYLURUSCWSASY-UHFFFAOYSA-N 0.000 claims 1
- ONANSSHSCHBJKW-UHFFFAOYSA-N n-[3-[7-(hydroxymethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2CO)C2=N1 ONANSSHSCHBJKW-UHFFFAOYSA-N 0.000 claims 1
- LZBGRUIJNCMSRE-UHFFFAOYSA-N n-[3-[7-(hydroxymethyl)-2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2CO)C2=N1 LZBGRUIJNCMSRE-UHFFFAOYSA-N 0.000 claims 1
- SKHUJQVFPTVJKH-UHFFFAOYSA-N n-[3-[7-acetyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2C(C)=O)C2=N1 SKHUJQVFPTVJKH-UHFFFAOYSA-N 0.000 claims 1
- NZZVCUOQSPFXRA-UHFFFAOYSA-N n-[3-[7-cyclopropyl-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2C3CC3)C2=N1 NZZVCUOQSPFXRA-UHFFFAOYSA-N 0.000 claims 1
- UAZRAOVSYBDSMH-UHFFFAOYSA-N n-[3-[7-cyclopropyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-4-yl]oxyphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2C3CC3)C2=N1 UAZRAOVSYBDSMH-UHFFFAOYSA-N 0.000 claims 1
- UAXPROIZGYSMOO-UHFFFAOYSA-N n-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-5-(2-hydroxyethyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(CCO)=CN2)C2=N1 UAXPROIZGYSMOO-UHFFFAOYSA-N 0.000 claims 1
- OSKRLMPMNNECGD-UHFFFAOYSA-N n-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-5-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCCCC3)C2=N1 OSKRLMPMNNECGD-UHFFFAOYSA-N 0.000 claims 1
- HXOJLOVOBMQWOX-UHFFFAOYSA-N n-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-5-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCCC3)C2=N1 HXOJLOVOBMQWOX-UHFFFAOYSA-N 0.000 claims 1
- SETKZRJYZNZHMO-UHFFFAOYSA-N n-[3-[[2-[4-(4-methylpiperazin-1-yl)anilino]-5-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCCCC3)C2=N1 SETKZRJYZNZHMO-UHFFFAOYSA-N 0.000 claims 1
- KARQYIZIHFFBDR-UHFFFAOYSA-N n-[3-[[2-[4-(4-methylpiperazin-1-yl)anilino]-5-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCCC3)C2=N1 KARQYIZIHFFBDR-UHFFFAOYSA-N 0.000 claims 1
- HAJRCWPFNCVVCY-UHFFFAOYSA-N n-[3-[[2-[4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2)C2=N1 HAJRCWPFNCVVCY-UHFFFAOYSA-N 0.000 claims 1
- YFIMTIUAPOZBKY-UHFFFAOYSA-N n-[3-[[2-[4-[[1-(2-fluoroethyl)azetidin-3-yl]amino]-2-methoxyanilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenyl]prop-2-enamide Chemical compound C=1C=C(NC=2N=C3NC=CC3=C(NC=3C=C(NC(=O)C=C)C=CC=3)N=2)C(OC)=CC=1NC1CN(CCF)C1 YFIMTIUAPOZBKY-UHFFFAOYSA-N 0.000 claims 1
- QXIPKEVCAWHBBL-UHFFFAOYSA-N n-[3-[[2-[4-[[1-(2-fluoroethyl)azetidin-3-yl]amino]-2-methoxyanilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C=1C=C(NC=2N=C3NC=CC3=C(OC=3C=C(NC(=O)C=C)C=CC=3)N=2)C(OC)=CC=1NC1CN(CCF)C1 QXIPKEVCAWHBBL-UHFFFAOYSA-N 0.000 claims 1
- WGBLPNFSWJRFER-UHFFFAOYSA-N n-[3-[[2-[[1-[2-(dimethylamino)ethyl]indol-5-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C=1C=C2N(CCN(C)C)C=CC2=CC=1NC(N=C1NC=CC1=1)=NC=1OC1=CC=CC(NC(=O)C=C)=C1 WGBLPNFSWJRFER-UHFFFAOYSA-N 0.000 claims 1
- MMYFQTGWGGGYML-UHFFFAOYSA-N n-[3-[[2-[[2-(piperidin-1-ylmethyl)quinolin-6-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC(OC=2C=3C=CNC=3N=C(NC=3C=C4C=CC(CN5CCCCC5)=NC4=CC=3)N=2)=C1 MMYFQTGWGGGYML-UHFFFAOYSA-N 0.000 claims 1
- REVVHHDVZSEMTI-UHFFFAOYSA-N n-[3-[[2-[[2-[(dimethylamino)methyl]quinolin-6-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1=CC2=NC(CN(C)C)=CC=C2C=C1NC(N=C1NC=CC1=1)=NC=1OC1=CC=CC(NC(=O)C=C)=C1 REVVHHDVZSEMTI-UHFFFAOYSA-N 0.000 claims 1
- PEOCEMXAFXTVAE-UHFFFAOYSA-N n-[3-[[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C=CN2)C2=N1 PEOCEMXAFXTVAE-UHFFFAOYSA-N 0.000 claims 1
- PPIDHDMRNYAPQN-UHFFFAOYSA-N n-[3-[[5-(azetidin-1-yl)-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCC3)C2=N1 PPIDHDMRNYAPQN-UHFFFAOYSA-N 0.000 claims 1
- HSSHUAJCPXEROO-UHFFFAOYSA-N n-[3-[[5-(azetidin-1-yl)-2-[4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CCC3)C2=N1 HSSHUAJCPXEROO-UHFFFAOYSA-N 0.000 claims 1
- DERXCLHUGPTWMG-UHFFFAOYSA-N n-[3-[[5-(aziridin-1-yl)-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)N3CC3)C2=N1 DERXCLHUGPTWMG-UHFFFAOYSA-N 0.000 claims 1
- ZJXKBKHHAXBPTH-UHFFFAOYSA-N n-[3-[[5-(dimethylamino)-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound N=1C(OC=2C=C(NC(=O)C=C)C=CC=2)=C2C(N(C)C)=CNC2=NC=1NC(C=C1F)=CC=C1N1CCN(C)CC1 ZJXKBKHHAXBPTH-UHFFFAOYSA-N 0.000 claims 1
- SIGRAWNPFKTSBV-UHFFFAOYSA-N n-[3-[[5-(dimethylamino)-2-[4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound N=1C(OC=2C=C(NC(=O)C=C)C=CC=2)=C2C(N(C)C)=CNC2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 SIGRAWNPFKTSBV-UHFFFAOYSA-N 0.000 claims 1
- MKBDTRHCEROTFU-UHFFFAOYSA-N n-[3-[[5-[(dimethylamino)methyl]-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound N=1C(OC=2C=C(NC(=O)C=C)C=CC=2)=C2C(CN(C)C)=CNC2=NC=1NC(C=C1F)=CC=C1N1CCN(C)CC1 MKBDTRHCEROTFU-UHFFFAOYSA-N 0.000 claims 1
- PHNGGJAITPBPLC-UHFFFAOYSA-N n-[3-[[5-[2-(dimethylamino)ethyl]-2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound N=1C(OC=2C=C(NC(=O)C=C)C=CC=2)=C2C(CCN(C)C)=CNC2=NC=1NC(C=C1F)=CC=C1N1CCN(C)CC1 PHNGGJAITPBPLC-UHFFFAOYSA-N 0.000 claims 1
- LWJSAYXNTLJFNR-UHFFFAOYSA-N n-[3-[[5-[2-(dimethylamino)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound N=1C(OC=2C=C(NC(=O)C=C)C=CC=2)=C2C(CCN(C)C)=CNC2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 LWJSAYXNTLJFNR-UHFFFAOYSA-N 0.000 claims 1
- BCIZOTIPJMSBAY-UHFFFAOYSA-N n-[3-[[5-cyclopropyl-2-[4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)C3CC3)C2=N1 BCIZOTIPJMSBAY-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/04—Artificial tears; Irrigation solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261680231P | 2012-08-06 | 2012-08-06 | |
| US61/680,231 | 2012-08-06 | ||
| US13/843,554 US9034885B2 (en) | 2012-01-13 | 2013-03-15 | EGFR modulators and uses thereof |
| US13/843,554 | 2013-03-15 | ||
| US201361814147P | 2013-04-19 | 2013-04-19 | |
| US61/814,147 | 2013-04-19 | ||
| US13/917,514 US8685988B2 (en) | 2012-08-06 | 2013-06-13 | EGFR modulators and uses thereof |
| US13/917,514 | 2013-06-13 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015107831A Division RU2645672C2 (ru) | 2012-08-06 | 2013-07-11 | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2018104702A true RU2018104702A (ru) | 2019-02-22 |
Family
ID=50068479
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018104702A RU2018104702A (ru) | 2012-08-06 | 2013-07-11 | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ |
| RU2015107831A RU2645672C2 (ru) | 2012-08-06 | 2013-07-11 | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015107831A RU2645672C2 (ru) | 2012-08-06 | 2013-07-11 | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ |
Country Status (22)
| Country | Link |
|---|---|
| EP (2) | EP3170825B1 (enExample) |
| JP (2) | JP6215938B2 (enExample) |
| KR (1) | KR102181365B1 (enExample) |
| CN (2) | CN103748096B (enExample) |
| AU (1) | AU2013300106B2 (enExample) |
| BR (1) | BR112015002709B1 (enExample) |
| CA (1) | CA2881275C (enExample) |
| CY (1) | CY1120844T1 (enExample) |
| DK (1) | DK2880035T3 (enExample) |
| ES (2) | ES2733576T3 (enExample) |
| HR (1) | HRP20170311T1 (enExample) |
| HU (1) | HUE031955T2 (enExample) |
| IN (1) | IN2015DN00914A (enExample) |
| LT (1) | LT2880035T (enExample) |
| MX (1) | MX361992B (enExample) |
| NZ (1) | NZ629807A (enExample) |
| PT (1) | PT2880035T (enExample) |
| RU (2) | RU2018104702A (enExample) |
| SG (1) | SG11201500872SA (enExample) |
| SM (1) | SMT201700136T1 (enExample) |
| WO (1) | WO2014025486A1 (enExample) |
| ZA (2) | ZA201500762B (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6105578B2 (ja) | 2011-07-21 | 2017-03-29 | トレロ ファーマシューティカルズ， インコーポレイテッド | 複素環式プロテインキナーゼ阻害剤 |
| US9034885B2 (en) | 2012-01-13 | 2015-05-19 | Acea Biosciences Inc. | EGFR modulators and uses thereof |
| US9464089B2 (en) | 2012-01-13 | 2016-10-11 | Acea Biosciences Inc. | Heterocyclic compounds and uses thereof |
| HK1203927A1 (en) | 2012-01-13 | 2015-11-06 | Acea Biosciences, Inc. | Heterocyclic compounds and uses as anticancer agents |
| ES2638179T3 (es) * | 2013-01-16 | 2017-10-19 | Signal Pharmaceuticals, Llc | Compuestos de pirrolopirimidina sustituidos, composiciones de los mismos, y métodos de tratamiento con los mismos |
| AU2014236820B2 (en) * | 2013-03-14 | 2018-08-02 | Sumitomo Pharma Oncology, Inc. | JAK2 and ALK2 inhibitors and methods for their use |
| AU2014287016B2 (en) * | 2013-07-11 | 2018-11-01 | Acea Biosciences Inc. | Pyrimidine derivatives as kinase inhibitors |
| WO2015127234A1 (en) * | 2014-02-20 | 2015-08-27 | Board Of Regents, The University Of Texas System | Use of ibrutinib to treat egfr mutant cancer |
| CN106715427A (zh) | 2014-07-14 | 2017-05-24 | 西格诺药品有限公司 | 利用取代的吡咯并嘧啶化合物、其组合物治疗癌症的方法 |
| NZ629796A (en) | 2014-07-14 | 2015-12-24 | Signal Pharm Llc | Amorphous form of 4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-n-methylbenzamide, compositions thereof and methods of their use |
| US10913744B2 (en) | 2015-02-13 | 2021-02-09 | Dana-Farber Cancer Institute, Inc. | LRRK2 inhibitors and methods of making and using the same |
| JP2018104290A (ja) * | 2015-04-28 | 2018-07-05 | アステラス製薬株式会社 | ピラジンカルボキサミド化合物を有効成分とする医薬組成物 |
| EP3312179B1 (en) * | 2015-04-29 | 2019-07-10 | Nanjing Sanhome Pharmaceutical Co., Ltd. | Fused-ring or tricyclic aryl pyrimidine compound used as kinase inhibitor |
| WO2017011720A1 (en) * | 2015-07-16 | 2017-01-19 | Signal Pharmaceuticals, Llc | Solod forms 4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d] oxazol-6-yl)17h-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-n-methylbenzamide, compositions thereof and methods of their use |
| WO2017059702A1 (en) | 2015-10-09 | 2017-04-13 | Acea Biosciences, Inc | Pharmaceutical salts, physical forms, and compositions of pyrrolopyrimidine kinase inhibitors, and methods of making same |
| CN105646496B (zh) * | 2016-01-20 | 2018-07-20 | 华侨大学 | 一种7H-吡咯并[2,3-d]嘧啶衍生物、其合成方法及应用 |
| CN107540661A (zh) * | 2016-06-24 | 2018-01-05 | 正大天晴药业集团股份有限公司 | 作为egfr抑制剂的苯胺嘧啶化合物的结晶 |
| CN107663208B (zh) * | 2016-07-27 | 2021-10-15 | 南京圣和药业股份有限公司 | 一种新型egfr激酶抑制剂的药用盐及其制备方法与用途 |
| CN107663207B (zh) * | 2016-07-27 | 2021-07-30 | 南京圣和药业股份有限公司 | 一种egfr激酶抑制剂的甲磺酸盐结晶及制备方法 |
| CN107955019B (zh) * | 2016-10-17 | 2021-09-14 | 广东众生药业股份有限公司 | 一种egfr抑制剂的盐型、晶型及其制备方法 |
| CN106749266B (zh) * | 2016-11-14 | 2019-01-22 | 山东大学 | 吡咯并[2,3-d]嘧啶类化合物的高效制备方法 |
| CN108299419B (zh) * | 2017-01-11 | 2022-04-26 | 南京圣和药业股份有限公司 | 一种新型egfr激酶抑制剂的几种新晶型及其制备方法 |
| WO2018145525A1 (zh) * | 2017-02-08 | 2018-08-16 | 中国医药研究开发中心有限公司 | 吡咯并芳杂环类化合物及其制备方法和医药用途 |
| JP2020516682A (ja) * | 2017-04-07 | 2020-06-11 | エイシア セラピューティクス， インコーポレイテッド | ピロロピリミジンキナーゼの薬学的な塩、物理的形態および組成物、ならびにその作製方法 |
| CN109422751B (zh) * | 2017-09-03 | 2022-04-22 | 上海美志医药科技有限公司 | 一类具有降解酪氨酸蛋白激酶jak3活性的化合物 |
| US12180581B2 (en) | 2017-09-18 | 2024-12-31 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| US11709156B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved analytical analysis |
| US11709155B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| US12181452B2 (en) | 2017-09-18 | 2024-12-31 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| KR102318929B1 (ko) * | 2017-12-28 | 2021-10-28 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 옥시-플루오로피페리딘 유도체 |
| KR102577241B1 (ko) * | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-플루오로피페리딘 유도체 |
| KR102577242B1 (ko) * | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-메틸피페리딘 유도체 |
| SG11202009443RA (en) | 2018-04-05 | 2020-10-29 | Sumitomo Dainippon Pharma Oncology Inc | Axl kinase inhibitors and use of the same |
| MX2020010556A (es) | 2018-04-13 | 2021-03-02 | Sumitomo Pharma Oncology Inc | Inhibidores de cinasa de insercion proviral en linfomas murinos (pim) para el tratamiento de neoplasias mieloproliferativas y fibrosis asociadas con cancer. |
| CN108530450B (zh) * | 2018-05-03 | 2021-03-30 | 赖建智 | 具有egfr抑制活性的化合物、制备方法及其在疾病治疗中的应用 |
| WO2020023910A1 (en) | 2018-07-26 | 2020-01-30 | Tolero Pharmaceuticals, Inc. | Methods for treating diseases associated with abnormal acvr1 expression and acvr1 inhibitors for use in the same |
| EP3613738A1 (en) * | 2018-08-23 | 2020-02-26 | Lead Discovery Center GmbH | 4-substituted pyrrolo[2,3-b]pyridine as erbb modulators useful for treating cancer |
| US11471456B2 (en) | 2019-02-12 | 2022-10-18 | Sumitomo Pharma Oncology, Inc. | Formulations comprising heterocyclic protein kinase inhibitors |
| CN111747950B (zh) | 2019-03-29 | 2024-01-23 | 深圳福沃药业有限公司 | 用于治疗癌症的嘧啶衍生物 |
| CN110407840A (zh) * | 2019-08-15 | 2019-11-05 | 重庆化工职业学院 | 一种艾维替尼的制备方法 |
| US12378253B2 (en) * | 2019-11-13 | 2025-08-05 | Zhejiang Longcharm Bio-Tech Pharma. Co., Ltd. | Pyrrolopyrimidine compound as BTK inhibitor and use thereof |
| US11918936B2 (en) | 2020-01-17 | 2024-03-05 | Waters Technologies Corporation | Performance and dynamic range for oligonucleotide bioanalysis through reduction of non specific binding |
| WO2021147952A1 (zh) * | 2020-01-21 | 2021-07-29 | 江苏先声药业有限公司 | 嘧啶并吡咯类化合物 |
| CN111848631B (zh) * | 2020-08-28 | 2022-04-19 | 四川大学华西医院 | 一种靶向EGFR突变的吡咯并[2,3-d]嘧啶衍生物及其制备方法和用途 |
| US12352734B2 (en) | 2020-09-24 | 2025-07-08 | Waters Technologies Corporation | Chromatographic hardware improvements for separation of reactive molecules |
| US20240100172A1 (en) | 2020-12-21 | 2024-03-28 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| JP7621624B2 (ja) * | 2021-01-11 | 2025-01-27 | 広州力▲しん▼生物科技有限公司 | ２－アミノピリミジン系化合物、その医薬組成物、及び使用 |
| CN114957248B (zh) * | 2022-05-09 | 2023-12-29 | 南开大学 | 一种吡咯并嘧啶化合物及其制备方法、药物组合物和应用 |
| CN115611989B (zh) * | 2022-10-09 | 2023-08-01 | 武汉理工大学 | 机械活化淀粉衍生物抑制剂的优化制备方法及应用 |
| WO2024092047A1 (en) | 2022-10-26 | 2024-05-02 | Sorrento Therapeutics, Inc. | Administration of pyrrolopyrimidine-based kinase inhibitors for treatment of psoriasis |
| CN120302975A (zh) | 2022-10-31 | 2025-07-11 | 住友制药美国公司 | 治疗骨髓增生性肿瘤的pim1抑制剂 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5563905A (en) | 1992-09-24 | 1996-10-08 | Hughes Aircraft Company | Network communication system having time-sliced protocol |
| US7468255B2 (en) | 2002-12-20 | 2008-12-23 | Acea Biosciences | Method for assaying for natural killer, cytotoxic T-lymphocyte and neutrophil-mediated killing of target cells using real-time microelectronic cell sensing technology |
| US7470533B2 (en) | 2002-12-20 | 2008-12-30 | Acea Biosciences | Impedance based devices and methods for use in assays |
| US7560269B2 (en) | 2002-12-20 | 2009-07-14 | Acea Biosciences, Inc. | Real time electronic cell sensing system and applications for cytotoxicity profiling and compound assays |
| JP2005537498A (ja) | 2002-07-20 | 2005-12-08 | アセア バイオサイエンシーズ，インク． | インピーダンスによる測定装置および方法 |
| US7732127B2 (en) | 2002-12-20 | 2010-06-08 | Acea Biosciences, Inc. | Dynamic monitoring of cell adhesion and spreading using the RT-CES system |
| EP1692258A4 (en) | 2003-11-12 | 2007-03-21 | Xiao Xu | REAL-TIME ELECTRONIC CELL DETECTION SYSTEMS FOR CELL-BASED TESTS |
| ES2381962T3 (es) * | 2005-09-21 | 2012-06-04 | 4Sc Ag | Nuevos sulfonilpirroles como inhibidores de las HDAC |
| US9908884B2 (en) * | 2009-05-05 | 2018-03-06 | Dana-Farber Cancer Institute, Inc. | EGFR inhibitors and methods of treating disorders |
| WO2011079231A1 (en) * | 2009-12-23 | 2011-06-30 | Gatekeeper Pharmaceutical, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
-
2013
- 2013-07-11 BR BR112015002709-1A patent/BR112015002709B1/pt active IP Right Grant
- 2013-07-11 CA CA2881275A patent/CA2881275C/en active Active
- 2013-07-11 JP JP2015526540A patent/JP6215938B2/ja active Active
- 2013-07-11 WO PCT/US2013/050163 patent/WO2014025486A1/en not_active Ceased
- 2013-07-11 AU AU2013300106A patent/AU2013300106B2/en active Active
- 2013-07-11 EP EP16202341.0A patent/EP3170825B1/en active Active
- 2013-07-11 ES ES16202341T patent/ES2733576T3/es active Active
- 2013-07-11 ES ES13745491.4T patent/ES2618007T3/es active Active
- 2013-07-11 RU RU2018104702A patent/RU2018104702A/ru not_active Application Discontinuation
- 2013-07-11 KR KR1020157006007A patent/KR102181365B1/ko active Active
- 2013-07-11 RU RU2015107831A patent/RU2645672C2/ru active
- 2013-07-11 LT LTEP13745491.4T patent/LT2880035T/lt unknown
- 2013-07-11 EP EP13745491.4A patent/EP2880035B9/en active Active
- 2013-07-11 IN IN914DEN2015 patent/IN2015DN00914A/en unknown
- 2013-07-11 CN CN201380001359.4A patent/CN103748096B/zh active Active
- 2013-07-11 CN CN201710229308.7A patent/CN107266453B/zh active Active
- 2013-07-11 HU HUE13745491A patent/HUE031955T2/en unknown
- 2013-07-11 HR HRP20170311TT patent/HRP20170311T1/hr unknown
- 2013-07-11 MX MX2015001715A patent/MX361992B/es active IP Right Grant
- 2013-07-11 NZ NZ629807A patent/NZ629807A/en not_active IP Right Cessation
- 2013-07-11 SG SG11201500872SA patent/SG11201500872SA/en unknown
- 2013-07-11 PT PT137454914T patent/PT2880035T/pt unknown
- 2013-07-11 DK DK13745491.4T patent/DK2880035T3/en active
- 2013-07-11 SM SM20170136T patent/SMT201700136T1/it unknown
-
2015
- 2015-02-02 ZA ZA2015/00762A patent/ZA201500762B/en unknown
-
2016
- 2016-01-29 ZA ZA2016/00648A patent/ZA201600648B/en unknown
-
2017
- 2017-01-17 JP JP2017005935A patent/JP2017061581A/ja not_active Withdrawn
- 2017-03-02 CY CY171100274T patent/CY1120844T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2018104702A (ru) | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ | |
| CN114599361B (zh) | Prmt5抑制剂的药物组合物 | |
| US9840500B2 (en) | Compounds as dual inhibitors of histone methyltransferases and DNA methyltransferases | |
| RU2018110770A (ru) | Ингибиторы mdm2 и их комбинации | |
| JP2019031517A (ja) | 過剰増殖性疾患の治療のためのｍｅｋ阻害剤とｅｒｋ阻害剤の組合せの使用 | |
| JP2014505735A5 (enExample) | ||
| JP2018528206A5 (enExample) | ||
| JP2015529194A5 (enExample) | ||
| WO2014198942A1 (en) | Pyrazolopyridine derivatives for use in the treatment of bladder cancer | |
| RU2015143526A (ru) | Производные 3-(арил или гетероарил)метилениндолин-2-она в качестве ингибиторов киназного пути раковых стволовых клеток для лечения рака | |
| JPWO2019189732A5 (enExample) | ||
| CA2473026A1 (en) | 2-(pyridin-2-ylamino)-pyrido[2,3-d]pyrimidin-7-ones | |
| RU2012148133A (ru) | Комбинация, включающая ингибитор циклинзависимой киназы 4 или циклинзависимой киназы 6 (cdk4/6) и ингибитор mtor, для лечения рака | |
| JP2014139226A5 (enExample) | ||
| JP2004527560A5 (enExample) | ||
| CA2407593A1 (en) | Fused heteroaryl derivatives | |
| RU2015139590A (ru) | ИНГИБИРУЮЩЕЕ Trk СОЕДИНЕНИЕ | |
| JP2014518544A5 (enExample) | ||
| KR20150081344A (ko) | 조합 요법 | |
| KR20140035334A (ko) | 종양 치료제 | |
| RU2012130929A (ru) | Гетероциклические соединения в качестве ингибиторов янус-киназы | |
| JP2018534314A5 (enExample) | ||
| JP2021500332A5 (enExample) | ||
| JPWO2020032105A5 (enExample) | ||
| TW202237119A (zh) | Ａｌｋ﹘５抑制劑和彼之用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20160712 |