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
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- RU
- Russia
- Prior art keywords
- phenyl
- alkyl
- hydrogen
- amino
- pyrrolo
- Prior art date
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- 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
-
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| WO2015127234A1 (en) * | 2014-02-20 | 2015-08-27 | Board Of Regents, The University Of Texas System | Use of ibrutinib to treat egfr mutant cancer |
| EA201790189A1 (ru) | 2014-07-14 | 2017-11-30 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Способы лечения злокачественного новообразования с использованием замещенных пирролопиримидиновых соединений, композиции на их основе |
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| 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 |
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| 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 |
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| US5563905A (en) | 1992-09-24 | 1996-10-08 | Hughes Aircraft Company | Network communication system having time-sliced protocol |
| 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 |
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| 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 |
| WO2004010102A2 (en) | 2002-07-20 | 2004-01-29 | Acea Biosciences, Inc. | Impedance based apparatuses and methods for analyzing cells and particles |
| US7732127B2 (en) | 2002-12-20 | 2010-06-08 | Acea Biosciences, Inc. | Dynamic monitoring of cell adhesion and spreading using the RT-CES system |
| US7470533B2 (en) | 2002-12-20 | 2008-12-30 | Acea Biosciences | Impedance based devices and methods for use in assays |
| BRPI0617167B8 (pt) * | 2005-09-21 | 2021-05-25 | Nycomed Gmbh | sulfonilpirróis como inibidores de hdac's, seu uso, composição farmacêutica e combinação |
| KR101705158B1 (ko) * | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| US20110207736A1 (en) * | 2009-12-23 | 2011-08-25 | Gatekeeper Pharmaceuticals, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
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